ChemWiki - User contributions [en]

It:Carmoisine

2006-12-04T10:48:31Z

Jrf05: /* ''Spectra of Carmoisine'' */

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|-
| colspan="1" |[[Density]]
|colspan="2"| 0.80gcm-1
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine5

{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|-
|[[Image:Proton_spectra_of_carmoisine.gif|thumb]]
|[[Image:Nmr_diagram_of_carmoisine.GIF|thumb|Individual proton environments]]
|}

[[Image:IR of carmoisine.gif]]

The IR spectrum can be assigned as follows:
{| border="1" cellpadding="2"
|-
|width="100pt"|'''Group'''
|width="100pt"|'''Wavenumber/cm-1'''
|-
|O-H ||3411
|-
|C-H ||2954
|-
|N=N ||1500-1400
|-
|S=O ||1100
|}

The aromatic stretches/bends of napthalene are present in the 800-500cm-1 range. This is deep inside the fingerprint region, so-called as it provides a unique 'fingerprint' for each molecule. Thus by analysis of the fingerprint region, the compound in question can be determined by comparing it to a known source from a already existing database.

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4
Carmoisine is prohibited in Japan, Norway, Sweden and the US.

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

5. http://www.aist.go.jp

It:Carmoisine

2006-12-04T10:46:51Z

Jrf05: IR analysis added

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|-
| colspan="1" |[[Density]]
|colspan="2"| 0.80gcm-1
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine5

{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|-
|[[Image:Proton_spectra_of_carmoisine.gif|thumb]]
|[[Image:Nmr_diagram_of_carmoisine.GIF|thumb|Individual proton environments]]
|}

[[Image:IR of carmoisine.gif]]

The IR spectrum can be assigned as follows:
{| border="1" cellpadding="2"
|-
|width="100pt"|'''Group'''
|width="100pt"|'''Wavenumber-1'''
|-
|O-H ||3411
|-
|C-H ||2954
|-
|N=N ||1500-1400
|-
|S=O ||1100
|}

The aromatic stretches/bends of napthalene are present in the 800-500cm-1 range. This is deep inside the fingerprint region, so-called as it provides a unique 'fingerprint' for each molecule. Thus by analysis of the fingerprint region, the compound in question can be determined by comparing it to a known source from a already existing database.

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4
Carmoisine is prohibited in Japan, Norway, Sweden and the US.

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

5. http://www.aist.go.jp

It:Carmoisine

2006-11-30T16:29:33Z

Jrf05: /* ''Spectra of Carmoisine'' */

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|-
| colspan="1" |[[Density]]
|colspan="2"| 0.80gcm-1
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine5

{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|-
|[[Image:Proton_spectra_of_carmoisine.gif|thumb]]
|[[Image:Nmr_diagram_of_carmoisine.GIF|thumb|Individual proton environments]]
|}

[[Image:IR of carmoisine.gif]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4
Carmoisine is prohibited in Japan, Norway, Sweden and the US.

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

5. http://www.aist.go.jp

It:Carmoisine

2006-11-30T16:25:17Z

Jrf05: /* ''Adverse Effects'' */

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|-
| colspan="1" |[[Density]]
|colspan="2"| 0.80gcm-1
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine5

{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|-
|[[Image:Proton_spectra_of_carmoisine.gif|thumb]]
|[[Image:Nmr_diagram_of_carmoisine.GIF|thumb|Individual proton environments]]
|}

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4
Carmoisine is prohibited in Japan, Norway, Sweden and the US.

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

5. http://www.aist.go.jp

It:Carmoisine

2006-11-30T16:23:52Z

Jrf05: added a little more data

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|-
| colspan="1" |[[Density]]
|colspan="2"| 0.80gcm-1
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine5

{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|-
|[[Image:Proton_spectra_of_carmoisine.gif|thumb]]
|[[Image:Nmr_diagram_of_carmoisine.GIF|thumb|Individual proton environments]]
|}

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

5. http://www.aist.go.jp

It:Carmoisine

2006-11-30T16:21:42Z

Jrf05: /* ''Spectra of Carmoisine'' */

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine5

{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|-
|[[Image:Proton_spectra_of_carmoisine.gif|thumb]]
|[[Image:Nmr_diagram_of_carmoisine.GIF|thumb|Individual proton environments]]
|}

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

5. http://www.aist.go.jp

It:Carmoisine

2006-11-30T16:20:24Z

Jrf05: /* ''References'' */

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine

{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|-
|[[Image:Proton_spectra_of_carmoisine.gif|thumb]]
|[[Image:Nmr_diagram_of_carmoisine.GIF|thumb|Individual proton environments]]
|}

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

5. http://www.aist.go.jp

It:Carmoisine

2006-11-30T16:17:16Z

Jrf05: images put into nmr table

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine

{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|-
|[[Image:Proton_spectra_of_carmoisine.gif|thumb]]
|[[Image:Nmr_diagram_of_carmoisine.GIF|thumb|Individual proton environments]]
|}

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

It:Carmoisine

2006-11-30T16:12:29Z

Jrf05: added nmr diagram of carmoisine

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine

{| border="1" cellpadding="2"
|-
|width="50pt"|'''Proton'''
|width="50pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|}

{|
|[[Image:Proton_spectra_of_carmoisine.gif|thumb]]
|[[Image:Nmr_diagram_of_carmoisine.GIF|thumb|Individual proton environments]]
|}

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

It:Carmoisine

2006-11-30T15:44:36Z

Jrf05: /* ''Spectra of Carmoisine'' */

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine

{| border="1" cellpadding="2"
|-
|width="50pt"|'''Proton'''
|width="50pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|}

[[Image:Proton_spectra_of_carmoisine.gif]]

IR spectrum of Carmoisine

[[Image:IR_of_carmoisine.gif]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

File:Nmr diagram of carmoisine.GIF

2006-11-30T15:32:21Z

Jrf05:

It:Carmoisine

2006-11-30T15:21:55Z

Jrf05: /* ''Introduction'' */

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-]) (=O)=O)=C2/N=N/C3=CC=C(S([O-]) (=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine
{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|}

[[Image:Proton_spectra_of_carmoisine.gif]]

IR spectrum of Carmoisine

[[Image:IR_of_carmoisine.gif]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

It:Carmoisine

2006-11-30T15:19:47Z

Jrf05: added nmr table of chemical shifts

==''Introduction''==
{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse;"
! {{chembox header}} colspan="3" | Carmoisine
|-
| align="center" colspan="3" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]]
|-
!{{chembox header}} colspan="3" |'''Rotatable structure of Carmoisine (excluding Na+ cations)'''
|-
| align="center" colspan="3" bgcolor="#ffffff" |<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
|-
! {{chembox header}} colspan="3" | General Chemical Data
|-
| colspan="1" |[[Systematic name]]
| colspan="2"| 2-(4-sulfo-1-Napthylazo) -1-Naphthol-4-sulfonic acid
|-
| colspan="1" | [[Chemical formula|Molecular formula]]
| colspan="2"| C20H12N2Na2O7S2
|-
| colspan="1" |[[Simplified molecular input line entry specification|SMILES]]
| colspan="2"| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/ N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| colspan="1" |[[Molecular weight]]
| colspan="2"| 502.42gmol-1
|-
| colspan="1" |[[Appearance]]
| colspan="2"|Red powder
|-
| colspan="1" |[[CAS registry number|CAS number]]
| colspan="2"|[3567-69-9]
|-
| colspan="1" |[[HS code]]
| colspan="2"|[3204.12]
|-
| colspan="1" |[[Einecs number]]
| colspan="2"|[222-657-4]
|-
| colspan="1" |[[Solubility (in water)]]
| colspan="2"|soluble
|-
| colspan="1" |[[Stability]]
| colspan="2"|Stable in ordinary conditions2
|-
| colspan="1" |[[Melting Point (degrees celsius)]]
| colspan="2"|>300
|-
| colspan="1" |[[pH]]
| colspan="2"|6-8
|-
| colspan="1" |[[Synonyms]]
|colspan="2"| CI Food Red 3
|}

Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine
{| border="1" cellpadding="2"
|-
|width="100pt"|'''Proton'''
|width="100pt"|'''Chemical Shift'''
|-
|Ha ||9.02
|-
|Hb ||8.71
|-
|Hc ||8.50
|-
|Hd ||8.48
|-
|He ||8.15
|-
|Hf ||8.07
|-
|Hg ||7.82
|-
|Hh ||7.78
|-
|Hi ||7.20
|-
|Hj ||7.63
|}

[[Image:Proton_spectra_of_carmoisine.gif]]

IR spectrum of Carmoisine

[[Image:IR_of_carmoisine.gif]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

It:Carmoisine

2006-11-30T14:40:20Z

Jrf05: /* ''Introduction'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine

[[Image:Proton_spectra_of_carmoisine.gif]]

IR spectrum of Carmoisine

[[Image:IR_of_carmoisine.gif]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-30T14:39:37Z

Jrf05: /* ''Introduction'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine

[[Image:Proton_spectra_of_carmoisine.gif]]

IR spectrum of Carmoisine

[[Image:IR_of_carmoisine.gif]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-30T14:36:48Z

Jrf05: /* ''Spectra of Carmoisine'' */

It:Carmoisine

2006-11-30T14:35:37Z

Jrf05: IR spectra added

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==
1H nmr spectrum of Carmoisine
[[Image:Proton_spectra_of_carmoisine.gif]]

IR spectrum of Carmoisine

[[Image:IR_of_carmoisine.gif]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

File:IR of carmoisine.gif

2006-11-30T14:34:07Z

Jrf05:

It:Carmoisine

2006-11-30T14:31:20Z

Jrf05: nmr of carmoisine added

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==

[[Image:Proton_spectra_of_carmoisine.gif]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

File:Proton spectra of carmoisine.gif

2006-11-30T14:30:04Z

Jrf05:

It:Carmoisine

2006-11-30T14:27:18Z

Jrf05: /* ''General properties of Azo dyes'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Spectra of Carmoisine''==

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-29T15:31:30Z

Jrf05: /* ''References'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T14:53:38Z

Jrf05: /* ''Adverse Effects'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

==''References''==
1. http://www.ukfoodguide.net/e122.htm

2. http://www.chemicalland21.com

3. 'Organic Chemistry' by Clayden, Greeves, Warren and Wothers page 572

4. http://www.chm.bris.ac.uk

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T14:26:20Z

Jrf05: Added structure description

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==
As the N=N bond is planar in carmoisine, (as it is in all azo dyes) to geometric isomers are possible, notably cis and trans isomers. The trans isomer is energetically more stable than the cis isomer as clearly there would be a preferance to having the bulky naphthalene groups on opposite sides on the molecule instead of next to each other.

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T14:21:30Z

Jrf05: /* ''Synthesis of Carmoisine'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Structure''==

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T14:21:02Z

Jrf05: /* ''General properties of Azo dyes'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''General properties of Azo dyes''==
The biggest advantage of azo dyes over other types of dyes is that they are cheap and cost-effective. Since only two organic compounds are required to make an azo dye, there is a lot of flexibility in what dyes are made as these two organic compounds can be altered straightforwardly. They are also environmentally sound as their synthesis occurs in water and hence easily disposed of. Lastly, it is easy to scale the relative proportions of each reactant up or down as desired due to the simplicity of the chemistry involved i the dye production.

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T14:15:42Z

Jrf05: /* ''Synthesis of Carmoisine'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''General properties of Azo dyes''==

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T14:14:01Z

Jrf05: /* ''Synthesis of Carmoisine'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine2.GIF]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

File:Synthesis of carmoisine2.GIF

2006-11-28T14:13:14Z

Jrf05:

It:Carmoisine

2006-11-28T14:10:21Z

Jrf05: /* ''Synthesis of Carmoisine'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis of carmoisine.GIF]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T14:05:41Z

Jrf05: Reaction for synthesis of carmoisine added

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye (a dye derived from an amino compound) that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==
The first step involves using an alkylated aromatic ring, which is firstly nitrated using concentrated HNO3 and concentrated H2SO4 and then reduced using Sn/HCl to a diazo component. That is to say, a primary aromatic amine. Using acidic conditions (HCl) and NaNO2 an unstable diazonium salt is produced. This is a good electrophile for activated aromatic rings. The process of making this diazonium salt is known as Diazotisation. Then, a coupling component is introduced with which to react this diazonium salt. This forms a the stable azo dye.3

Therefore in the case of Carmoisine, the following would occur:

[[Image:Synthesis_of_carmoisine.GIF]]

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 4

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

File:Synthesis of carmoisine.GIF

2006-11-28T14:04:36Z

Jrf05:

It:Carmoisine

2006-11-28T13:42:12Z

Jrf05: /* ''Synthesis of Carmoisine'' */

It:Carmoisine

2006-11-28T13:41:36Z

Jrf05: /* ''Adverse Effects'' */

It:Carmoisine

2006-11-28T13:41:07Z

Jrf05: Desciption of synthesis of azo dyes

It:Carmoisine

2006-11-28T13:25:24Z

Jrf05: /* ''Introduction'' */

It:Carmoisine

2006-11-28T13:16:09Z

Jrf05: /* ''Introduction'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. It has the E number E122. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 3

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T13:15:44Z

Jrf05: /* ''Adverse Effects'' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children, with the hyperactive children's support group (HCSG) recommending that it is banned from a child's diet. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 3

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T12:36:51Z

Jrf05: Added information on adverse effects

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==

==''Adverse Effects''==
Carmoisine is believed to be linked with hyperactivity in children. Also causes reactions in sensitive people with for example an aspirin allergy or asthma. Skin rashes such as urticaria or swelling e.g. odeme are some of these reactions. 3

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T12:31:06Z

Jrf05: /* '''Introduction''' */

==''Introduction''==
Carmoisine also commonly known as Azorubine and is a red azo dye that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

==''Synthesis of Carmoisine''==

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T12:28:16Z

Jrf05: /* '''Introduction''' */

=='''Introduction'''==
Carmoisine also commonly known as Azorubine and is a red azo dye that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1

<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T12:28:03Z

Jrf05: Added 3-D structure of Carmoisine

=='''Introduction'''==
Carmoisine also commonly known as Azorubine and is a red azo dye that is used in sweets, for example jellies, as well as marzipan, packet cheesecake, packet soup mix and prepackaged sponge puddings or swiss rolls. On a more scientific note, it is used in the photometric determination of Mg, Pd, Cu, Sn and Cr.1
<jmol>
<jmolApplet>
<size>200</size>
<color>white</color>
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
HEADER NONAME 28-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 28-Nov-06 0 NONE 4
ATOM 1 O 0 -1.415 2.753 0.006 0.00 0.00 O+0
ATOM 2 C 0 -2.457 1.882 0.003 0.00 0.00 C+0
ATOM 3 C 0 -3.733 2.358 0.002 0.00 0.00 C+0
ATOM 4 C 0 -4.818 1.463 -0.001 0.00 0.00 C+0
ATOM 5 C 0 -6.142 1.932 -0.003 0.00 0.00 C+0
ATOM 6 C 0 -7.173 1.043 -0.007 0.00 0.00 C+0
ATOM 7 C 0 -6.937 -0.330 -0.008 0.00 0.00 C+0
ATOM 8 C 0 -5.668 -0.823 -0.006 0.00 0.00 C+0
ATOM 9 C 0 -4.577 0.065 -0.003 0.00 0.00 C+0
ATOM 10 C 0 -3.258 -0.412 0.000 0.00 0.00 C+0
ATOM 11 S 0 -2.940 -2.145 -0.001 0.00 0.00 S+0
ATOM 12 O 0 -3.027 -2.578 -1.387 0.00 0.00 O-1
ATOM 13 O 0 -1.606 -2.319 0.551 0.00 0.00 O+0
ATOM 14 O 0 -3.967 -2.752 0.833 0.00 0.00 O+0
ATOM 15 C 0 -2.205 0.491 -0.004 0.00 0.00 C+0
ATOM 16 N 0 -0.920 0.035 -0.001 0.00 0.00 N+0
ATOM 17 N 0 0.062 0.871 -0.005 0.00 0.00 N+0
ATOM 18 C 0 1.345 0.415 -0.002 0.00 0.00 C+0
ATOM 19 C 0 1.614 -0.949 0.004 0.00 0.00 C+0
ATOM 20 C 0 2.923 -1.410 0.006 0.00 0.00 C+0
ATOM 21 C 0 3.985 -0.558 0.002 0.00 0.00 C+0
ATOM 22 S 0 5.623 -1.207 0.005 0.00 0.00 S+0
ATOM 23 O 0 6.069 -1.203 -1.380 0.00 0.00 O-1
ATOM 24 O 0 6.414 -0.321 0.844 0.00 0.00 O+0
ATOM 25 O 0 5.531 -2.552 0.552 0.00 0.00 O+0
ATOM 26 C 0 3.788 0.833 -0.005 0.00 0.00 C+0
ATOM 27 C 0 2.470 1.350 -0.012 0.00 0.00 C+0
ATOM 28 C 0 2.270 2.735 -0.020 0.00 0.00 C+0
ATOM 29 C 0 3.346 3.572 -0.020 0.00 0.00 C+0
ATOM 30 C 0 4.644 3.067 -0.013 0.00 0.00 C+0
ATOM 31 C 0 4.875 1.725 -0.010 0.00 0.00 C+0
ATOM 32 H 0 -1.202 2.931 0.932 0.00 0.00 H+0
ATOM 33 H 0 -3.912 3.423 0.003 0.00 0.00 H+0
ATOM 34 H 0 -6.341 2.994 -0.002 0.00 0.00 H+0
ATOM 35 H 0 -8.190 1.408 -0.008 0.00 0.00 H+0
ATOM 36 H 0 -7.774 -1.013 -0.011 0.00 0.00 H+0
ATOM 37 H 0 -5.501 -1.889 -0.007 0.00 0.00 H+0
ATOM 38 H 0 0.797 -1.656 0.007 0.00 0.00 H+0
ATOM 39 H 0 3.104 -2.475 0.011 0.00 0.00 H+0
ATOM 40 H 0 1.268 3.139 -0.026 0.00 0.00 H+0
ATOM 41 H 0 3.191 4.640 -0.027 0.00 0.00 H+0
ATOM 42 H 0 5.481 3.750 -0.014 0.00 0.00 H+0
ATOM 43 H 0 5.887 1.347 -0.004 0.00 0.00 H+0
CONECT 1 2 32 0 0 NONE 48
CONECT 2 1 15 3 0 NONE 49
CONECT 3 2 4 33 0 NONE 50
CONECT 4 3 9 5 0 NONE 51
CONECT 5 4 6 34 0 NONE 52
CONECT 6 5 7 35 0 NONE 53
CONECT 7 6 8 36 0 NONE 54
CONECT 8 7 9 37 0 NONE 55
CONECT 9 8 4 10 0 NONE 56
CONECT 10 9 11 15 0 NONE 57
CONECT 11 10 12 13 14 NONE 58
CONECT 12 11 0 0 0 NONE 59
CONECT 13 11 0 0 0 NONE 60
CONECT 14 11 0 0 0 NONE 61
CONECT 15 10 2 16 0 NONE 62
CONECT 16 15 17 0 0 NONE 63
CONECT 17 16 18 0 0 NONE 64
CONECT 18 17 27 19 0 NONE 65
CONECT 19 18 20 38 0 NONE 66
CONECT 20 19 21 39 0 NONE 67
CONECT 21 20 22 26 0 NONE 68
CONECT 22 21 23 24 25 NONE 69
CONECT 23 22 0 0 0 NONE 70
CONECT 24 22 0 0 0 NONE 71
CONECT 25 22 0 0 0 NONE 72
CONECT 26 21 31 27 0 NONE 73
CONECT 27 26 18 28 0 NONE 74
CONECT 28 27 29 40 0 NONE 75
CONECT 29 28 30 41 0 NONE 76
CONECT 30 29 31 42 0 NONE 77
CONECT 31 30 26 43 0 NONE 78
END NONE 79
M END</inlineContents>
</jmolApplet>
</jmol>
'''Rotatable structure of Carmoisine (excluding Na+ cations)'''

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Carmoisine.GIF|{{PAGENAME}}]] 

|-
| [[Systematic name]]
| 2-(4-sulfo-1-Napthylazo)-1-Naphthol-4-sulfonic acid
|-
| [[Chemical formula|Molecular formula]]
| C20H12N2Na2O7S2
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| OC2=CC1=CC=CC=C1C(S([O-])(=O)=O)=C2/N=N/C3=CC=C(S([O-])(=O)=O)C(C)=C3/C=C.[Na+].[Na+]
|-
| [[Molecular weight]]
| 502.42gmol-1
|-
| [[Appearance]]
| Red powder
|-
| [[CAS registry number|CAS number]]
| [3567-69-9]
|-
| [[HS code]]
| [3204.12]
|-
| [[Einecs number]]
| [222-657-4]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
| [[Melting Point (degrees celsius)]]
| >300
|-
| [[pH]]
| 6-8
|-
| [[Synonyms]]
| CI Food Red 3
|-}

It:Carmoisine

2006-11-28T12:27:13Z

Jrf05: /* '''Introduction''' */

It:Carmoisine

2006-11-28T12:19:31Z

Jrf05: Added structure of carmoisine

File:Carmoisine.GIF

2006-11-28T12:18:34Z

Jrf05:

It:Carmoisine

2006-11-28T12:15:35Z

Jrf05: /* '''Introduction''' */

It:Carmoisine

2006-11-28T12:14:47Z

Jrf05: Added chemical properties table

It:Carmoisine

2006-11-28T11:52:56Z

Jrf05: Introduction added

It:projects

2006-11-28T11:45:13Z

Jrf05: /* Supplemental Project Page */

__FORCETOC__

'''''You MUST use the Edit buttons on the right to edit this content. Do NOT use the Edit button on the top of this page.'''''
== Sandbox (Play-Pen) ==

This is an area where you can play without worrying what you do. Enter it by pressing the [Edit] button '''on the right''' and '''not''' at the top. Go here for a [http://en.wikipedia.org/wiki/Wikipedia:Cheatsheet ''cheat sheet''] summary of how to create a Wiki page. It's a free-for-all in here! Learn how to use a Wiki by coming here! PS This is how to do Greek: Α, α, β Δ, δ
Try copying/pasting some of the [http://www.ch.ic.ac.uk/local/it/lab1.html examples in the course work] into this page. See the effect by selecting '''Show Preview'''. No not use '''Save Page''' so as to leave this area uncluttered for others.
----

== Main Project Page ==
'''Please do not edit this page itself'''. Click on one of the titles to start editing.
{| summary="CIT Project Titles" border="1"
! bgcolor="cyan" |Project Number
! bgcolor="cyan" |General Keywords
|-
| bgcolor="#CCFF00" |01
| bgcolor="#CCFF00" | [[it:Lignocaine|Lignocaine (used in dentistry as a "local")]]
|-
| bgcolor="#CCFF00" |02
| bgcolor="#66FF99" | [[it:Piperine|Piperine (active ingredient of both black and white pepper)]]
|-
| bgcolor="#CCFF00" |03
| bgcolor="#CCFF00" | [[it:Rapamycin|Rapamycin (prevents transplant rejection)]]
|-
| bgcolor="#CCFF00" |04
| bgcolor="#66FF99" | [[it:Gossypol|Gossypol (male birth control)]]
|-
| bgcolor="#CCFF00" |05
| bgcolor="#CCFF00" | [[it:Gentamycin|Gentamicin A (aminoglycoside antibiotic)]]
|-
| bgcolor="#CCFF00" |06
| bgcolor="#66FF99" | [[it:Herceptin|Herceptin (topical anticancer drug)]]
|-
| bgcolor="#CCFF00" |07
| bgcolor="#CCFF00" | [[it:Gingerone|Zingerone (the characteristic smell of ginger)]]
|-
| bgcolor="#CCFF00" |08
| bgcolor="#66FF99" | [[it:Sucralose|Sucralose (non-metabolizable sweetening agent)]]
|-
| bgcolor="#CCFF00" |09
| bgcolor="#CCFF00" | [[it:Bufotoxin|Bufotoxin (active component of the toad ''Bufo vulgaris'')]]
|-
| bgcolor="#CCFF00" |10
| bgcolor="#66FF99" | [[it:Roaccutane|Roaccutane (treatment for severe acne)]]
|-
| bgcolor="#CCFF00" |11
| bgcolor="#CCFF00" | [[it:Sibutramine|Sibutramine (appetite suppresor)]]
|-
| bgcolor="#CCFF00" |12
| bgcolor="#66FF99" | [[it:Anandamide|Anandamide (the "feel-good" factor in chocolate)]]
|-
| bgcolor="#CCFF00" |13
| bgcolor="#CCFF00" | [[it:h3nbh3|Ammonia-borane: H3N-BH3 (Hydrogen storage molecule?)]]
|-
| bgcolor="#CCFF00" |14
| bgcolor="#66FF99" | [[it:Methoxsalen|Methoxsalen (Treatment of psoriasis)]]
|-
| bgcolor="#CCFF00" |15
| bgcolor="#CCFF00" | [[it:Hycocine|Hyoscine (From Mandrake and Witches Henbane, pre-med before surgery)]]
|-
| bgcolor="#CCFF00" |16
| bgcolor="#66FF99" | [[it:Capreomycin|Capreomycin (Drug-resistant TB)]]
|-
| bgcolor="#CCFF00" |17
| bgcolor="#CCFF00" | [[it:wilkinson|Wilkinson's catalyst]]
|-
| bgcolor="#CCFF00" |18
| bgcolor="#66FF99" | [[it:Jacobsen|Jacobsen's epoxidation catalyst]]
|-
| bgcolor="#CCFF00" |19
| bgcolor="#CCFF00" | [[it:Methylaluminoxane|Methylaluminoxane: MAO - hugely important ethylene polymerisation cocatalyst]]
|-
| bgcolor="#CCFF00" |20
| bgcolor="#66FF99" | [[it:Schwartz|Schwartz reagent for the hydrozirconation of alkenes and alkynes]]
|-
| bgcolor="#CCFF00" |21
| bgcolor="#CCFF00" | [[it:Schrock|Schrock metathesis catalyst]]
|-
| bgcolor="#CCFF00" |22
| bgcolor="#66FF99" | [[it:knots|Molecular-scale knots (nanoscale devices)]]
|-
|bgcolor="#CCFF00" |23
| bgcolor="#CCFF00" | [[it:Vioxx|Vioxx (treatment of osteoarthritis symptoms and pain)]]
|-
| bgcolor="#CCFF00" |24
| bgcolor="#66FF99" | [[it:Sertraline|Sertraline HCl (anti-depression)]]
|-
| bgcolor="#CCFF00" |25
| bgcolor="#CCFF00" | [[it:Ceftriaxone|Ceftriaxone (Gonorrhoea)]]
|-
| bgcolor="#CCFF00" |26
| bgcolor="#66FF99" | [[it:Zithromycin|Zithromycin (anti-infective)]]
|-
| bgcolor="#CCFF00" |27
| bgcolor="#CCFF00" | [[it:Lipitor|Lipitor (Cholesterol reducing agent)]]
|-
| bgcolor="#CCFF00" |28
| bgcolor="#66FF99" | [[it:Cyameluric Acid|Cyameluric acid (Linus Pauling's last idea!)]]
|}

== Supplemental Project Page ==

This area is for people who wish to create their own projects if none of the above appeal to them. Click on the '''Edit''' button to the right to open up an editable page,
then add an entry below as follows

*<nowiki> [[it:name_of_project|Descriptive name of intended project]]</nowiki>
*This will produce the effect: [[it:name_of_project|Descriptive name of intended project]]
----
*[[it:sitagliptin_page|Sitagliptin]]
*[[it:Retinal|Retinal, molecule of sight]]
*[[it:Tamoxifen|Tamoxifen, breast cancer treatment]]
*[[it:Morphine|Morphine, painkiller]]
*[[it:Pelargonidin|Pelargonidin, colouring in nature]]
*[[it:Propanil|Propanil, weedkiller]]
*[[it:Ranitidine|Ranitidine, antiulcerative]]
*[[it:chlorphentermine|chlorphentermine, anorectic]]
*[[it:Serotonin|Serotonin, The 'HAPPY' Drug]]
*[[it:Amphidinolide T1|Amphidinolide T1]]
*[[it:Rosiglitazone|Rosiglitazone, drug that is currently used to treat diabetes.]]
*[[it:Furosemide|Furosemide]]
*[[it:Tryptophan|Tryptophan]]
*[[it:methylpentynol|methylpentynol, tranquilliser.]]
*[[it:Ferrocene|Ferrocene]]
*[[it:Scopolamine|Scopolamine, the (Former) Truth Drug]]
*[[it:Camptothecin|Camptothecin,Anti-cancer agent ]]
*[[it:Salmeterol|Salmeterol, an agonist used to treat asthma]]
*[[it:Psilocin|Psilocin]]
*[[it:Epibatidine|Epibatidine]]
*[[it:Beta Carotene|Beta Carotene]]
*[[it:Thyroxine|Thyroxine, the Thyroid Hormone]]
*[[it:Tetrahydrocannabinol|Tetrahydrocannabinol]]
*[[it:Linalool|Linalool(A component of essential oil)]]
*[[it:Dihydroartemisinin| Dihydroartemisinin, An Active Anti-Malarial]]
*[[it:Acrolein|Acrolein]]
*[[it:Cinnamaldehyde|Cinnamaldehyde: The smell and taste in the spice cinnamon]]
*[[it:Melatonin|Melatonin: The All-Natural Nightcap]]
*[[it:Benzylpiperazine|Benzylpiperazine (BZP): Party Pills]]
*[[it:Vanillin|Vanillin, flavouring used in food]]
*[[it:Gingerol|Gingerol, precursor of Zingerone]]
*[[it:MSG|MSG; because everyone loves the flavour]]
*[[it:DDT|DDT, Pesticide]]
*[[it:Oseltamivir|Oseltamivir, neuraminidase inhibitor]]
*[[it:Caffeine|Caffeine]]
*[[it:Fullerene]]
*[[it:Histrionicotoxin]]
*[[it:limonene]]
*[[it:Capsanthin]]
*[[it:Safrole|Safrole: A formerly popular food and drinks additive]]
*[[it:Adenosine_Triphosphate|Adenosine Triphosphate (ATP), Energy source in muscles]]
*[[it:Aspartame|Aspartame: Artificial sweetener]]
*[[it:Astemizole|Astemizole:non-sedating anti-histamine]]
*[[it:Flucloxacillin|Flucloxacillin:antibiotic]]
*[[it:Quinine|Quinine: The Perfect Tonic for Any Fever]]
*[[it:Caramel|Caramel]]
*[[it:Azithromycin|Azythromycin]]
*[[it:Artemisinin|Artemisinin: An antimalarial drug]]
*[[it:Bradykinin|Bradykinin]]
*[[it:Carminic_acid|Carminic acid, Red colouring agent]]
*[[it:Oxytocin|Oxytocin: The Hormone of Love]]
*[[it:Carmoisine|Carmoisine]]

== [[Special:Export|Export Pages]] ==

This takes you to an '''Export''' page. A backup of the Projects area can be made (in XML) if you want to keep your own ''snapshot'' of the project pages at any instant. After you Export the page you want (ie '''It:projects''' or '''It:Lignocaine''' for example) the XML encoding of it will appear in your browser Window. You should '''view source''' for this material, copy it to a text editor, and thence save it to disk.

== Overlaps ==

If someone else starts editing a page at the same time as you, the system will detect this and offer alternatives for you to deal with. For example, it may suggest you copy the contents of the page you have been editing and merge it into the other person's page,
so that both the sets of edits are preserved. Read the on-screen instructions carefully!

Another precaution you could take is to keep a copy of the contents of the page you are editing in eg Wordpad (or Word),
make the changes there, and then copy the entire lot to the Wiki page to preview and then save. That way, if your contribution
is overlapped by someone else, you will still have a copy, and you can then resubmit it.
----
--[[User:Rzepa|Rzepa]] 12:25, 19 October 2006 (BST)--[[User:Rzepa|Rzepa]] 08:31, 5 November 2006 (UTC)

== Wiki Utillities ==
Utilities have been written to help the conversion of material from HTML.

# [http://diberri.dyndns.org/wikipedia/html2wiki/ A HTML2Wiki Converter]

No wiki2html converter suitable for use has yet been identified.
=== Wiki Templates ===

[[Template:DOI]] and [[Template:Doi-inline]] are providea as (protected) templates for your use. Many other templates exist, often to be found on e.g. Wikipedia pages. You may decide one of these is of particular use, or of interest. If so, you can install it on the wiki here for you and others to use. Add below a line that looks like {{template-name|parameter}}, save, and click on the red text to create the new template. If you prefer the task of adding useful templates to that of adding information about molecules, then you will be given full credit for performing this valuable service for others!
--[[User:Rzepa|Rzepa]] 14:41, 20 October 2006 (BST)

----
[[Template:Chem-Data]]

[[Template:Chembox supplement]] - to be linked to from the supplementary section of the table in the template above, for usage see [[Template_talk:chembox_supplement|here]]

[[Template:NFPA_704]] - for notes on how to use, see [[Template_talk:NFPA_704|here]]

[[R & S Phrases]]

It:Capsanthin

2006-11-23T16:23:58Z

Jrf05: /* ''Synthesis of Capsanthin'' */

=='''Capsanthin'''==
=''Introduction''=
Capsanthin is used as a flavour enhancer in foods and is of the same overall classification as beta-carotene. That is to say, it is a carotenoid, a naturally occuring organic pigment found in plants. The carotenoids are separated into two separate groups, the Xanthophyll's and the carotenes. Capsanthin makes up 30-60% of the carotenoids, and is a Xanthphyll - responsible for the red colour in peppers and paprika.1 Lastly, Capsanthin may also be used to enhance the colour of egg yolks by adding it to poultry feed.

<jmol>
<jmolApplet>
<size>250</size>
<color>white</color>
<script>zoom 80; bns on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>water.mol
title1
title2
HEADER NONAME 21-Nov-06 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 21-Nov-06 0 NONE 4
ATOM 1 O 0 10.993 -1.738 -0.041 0.00 0.00 O+0
ATOM 2 C 0 10.960 -0.557 -0.332 0.00 0.00 C+0
ATOM 3 C 0 12.244 0.211 -0.513 0.00 0.00 C+0
ATOM 4 C 0 12.246 0.914 -1.872 0.00 0.00 C+0
ATOM 5 C 0 12.404 1.244 0.616 0.00 0.00 C+0
ATOM 6 C 0 12.517 2.651 0.026 0.00 0.00 C+0
ATOM 7 C 0 11.210 1.169 1.568 0.00 0.00 C+0
ATOM 8 C 0 13.703 0.880 1.365 0.00 0.00 C+0
ATOM 9 C 0 13.904 -0.626 1.066 0.00 0.00 C+0
ATOM 10 H 0 13.275 -1.237 1.714 0.00 0.00 H+0
ATOM 11 O 0 15.279 -0.991 1.208 0.00 0.00 O+0
ATOM 12 C 0 13.450 -0.746 -0.411 0.00 0.00 C+0
ATOM 13 C 0 9.734 0.085 -0.502 0.00 0.00 C+0
ATOM 14 C 0 8.555 -0.606 -0.285 0.00 0.00 C+0
ATOM 15 C 0 7.329 0.035 -0.455 0.00 0.00 C+0
ATOM 16 C 0 7.288 1.482 -0.876 0.00 0.00 C+0
ATOM 17 C 0 6.151 -0.655 -0.238 0.00 0.00 C+0
ATOM 18 C 0 4.925 -0.040 -0.490 0.00 0.00 C+0
ATOM 19 C 0 3.746 -0.693 -0.178 0.00 0.00 C+0
ATOM 20 C 0 2.520 -0.077 -0.430 0.00 0.00 C+0
ATOM 21 C 0 2.480 1.299 -1.042 0.00 0.00 C+0
ATOM 22 C 0 1.342 -0.729 -0.118 0.00 0.00 C+0
ATOM 23 C 0 0.116 -0.167 -0.478 0.00 0.00 C+0
ATOM 24 C 0 -1.063 -0.764 -0.075 0.00 0.00 C+0
ATOM 25 C 0 -2.289 -0.201 -0.435 0.00 0.00 C+0
ATOM 26 C 0 -3.467 -0.798 -0.032 0.00 0.00 C+0
ATOM 27 C 0 -3.430 -2.056 0.796 0.00 0.00 C+0
ATOM 28 C 0 -4.695 -0.235 -0.393 0.00 0.00 C+0
ATOM 29 C 0 -5.868 -0.763 0.102 0.00 0.00 C+0
ATOM 30 C 0 -7.091 -0.143 -0.182 0.00 0.00 C+0
ATOM 31 C 0 -8.253 -0.666 0.309 0.00 0.00 C+0
ATOM 32 C 0 -8.219 -1.912 1.156 0.00 0.00 C+0
ATOM 33 C 0 -9.480 -0.044 0.024 0.00 0.00 C+0
ATOM 34 C 0 -10.645 -0.625 0.415 0.00 0.00 C+0
ATOM 35 C 0 -11.873 0.059 0.238 0.00 0.00 C+0
ATOM 36 C 0 -12.004 1.258 0.782 0.00 0.00 C+0
ATOM 37 C 0 -10.842 1.815 1.563 0.00 0.00 C+0
ATOM 38 C 0 -13.245 2.094 0.665 0.00 0.00 C+0
ATOM 39 C 0 -14.426 1.225 0.228 0.00 0.00 C+0
ATOM 40 H 0 -14.706 0.553 1.039 0.00 0.00 H+0
ATOM 41 O 0 -15.537 2.059 -0.109 0.00 0.00 O+0
ATOM 42 C 0 -14.002 0.405 -0.997 0.00 0.00 C+0
ATOM 43 C 0 -12.950 -0.615 -0.562 0.00 0.00 C+0
ATOM 44 C 0 -12.336 -1.270 -1.801 0.00 0.00 C+0
ATOM 45 C 0 -13.612 -1.689 0.304 0.00 0.00 C+0
ATOM 46 H 0 11.412 1.614 -1.920 0.00 0.00 H+0
ATOM 47 H 0 13.183 1.456 -1.999 0.00 0.00 H+0
ATOM 48 H 0 12.144 0.173 -2.665 0.00 0.00 H+0
ATOM 49 H 0 11.616 2.880 -0.544 0.00 0.00 H+0
ATOM 50 H 0 12.630 3.375 0.833 0.00 0.00 H+0
ATOM 51 H 0 13.385 2.701 -0.632 0.00 0.00 H+0
ATOM 52 H 0 11.069 0.139 1.895 0.00 0.00 H+0
ATOM 53 H 0 11.396 1.803 2.435 0.00 0.00 H+0
ATOM 54 H 0 10.312 1.513 1.053 0.00 0.00 H+0
ATOM 55 H 0 14.541 1.461 0.981 0.00 0.00 H+0
ATOM 56 H 0 13.583 1.043 2.436 0.00 0.00 H+0
ATOM 57 H 0 15.339 -1.936 1.010 0.00 0.00 H+0
ATOM 58 H 0 13.147 -1.768 -0.636 0.00 0.00 H+0
ATOM 59 H 0 14.248 -0.427 -1.082 0.00 0.00 H+0
ATOM 60 H 0 9.705 1.121 -0.804 0.00 0.00 H+0
ATOM 61 H 0 8.585 -1.643 0.017 0.00 0.00 H+0
ATOM 62 H 0 8.198 1.727 -1.423 0.00 0.00 H+0
ATOM 63 H 0 6.423 1.649 -1.518 0.00 0.00 H+0
ATOM 64 H 0 7.213 2.116 0.007 0.00 0.00 H+0
ATOM 65 H 0 6.180 -1.672 0.126 0.00 0.00 H+0
ATOM 66 H 0 4.896 0.946 -0.929 0.00 0.00 H+0
ATOM 67 H 0 3.775 -1.679 0.261 0.00 0.00 H+0
ATOM 68 H 0 2.397 1.213 -2.126 0.00 0.00 H+0
ATOM 69 H 0 1.619 1.845 -0.655 0.00 0.00 H+0
ATOM 70 H 0 3.394 1.837 -0.790 0.00 0.00 H+0
ATOM 71 H 0 1.370 -1.674 0.405 0.00 0.00 H+0
ATOM 72 H 0 0.090 0.735 -1.071 0.00 0.00 H+0
ATOM 73 H 0 -1.036 -1.666 0.519 0.00 0.00 H+0
ATOM 74 H 0 -2.316 0.701 -1.029 0.00 0.00 H+0
ATOM 75 H 0 -4.444 -2.429 0.937 0.00 0.00 H+0
ATOM 76 H 0 -2.833 -2.811 0.283 0.00 0.00 H+0
ATOM 77 H 0 -2.985 -1.839 1.767 0.00 0.00 H+0
ATOM 78 H 0 -4.724 0.614 -1.060 0.00 0.00 H+0
ATOM 79 H 0 -5.844 -1.656 0.710 0.00 0.00 H+0
ATOM 80 H 0 -7.115 0.750 -0.789 0.00 0.00 H+0
ATOM 81 H 0 -9.239 -2.220 1.390 0.00 0.00 H+0
ATOM 82 H 0 -7.715 -2.710 0.610 0.00 0.00 H+0
ATOM 83 H 0 -7.680 -1.708 2.081 0.00 0.00 H+0
ATOM 84 H 0 -9.497 0.897 -0.506 0.00 0.00 H+0
ATOM 85 H 0 -10.634 -1.609 0.861 0.00 0.00 H+0
ATOM 86 H 0 -10.200 2.391 0.898 0.00 0.00 H+0
ATOM 87 H 0 -11.215 2.461 2.358 0.00 0.00 H+0
ATOM 88 H 0 -10.271 0.995 1.999 0.00 0.00 H+0
ATOM 89 H 0 -13.468 2.547 1.631 0.00 0.00 H+0
ATOM 90 H 0 -13.083 2.880 -0.072 0.00 0.00 H+0
ATOM 91 H 0 -15.759 2.564 0.685 0.00 0.00 H+0
ATOM 92 H 0 -14.868 -0.113 -1.409 0.00 0.00 H+0
ATOM 93 H 0 -13.575 1.067 -1.750 0.00 0.00 H+0
ATOM 94 H 0 -11.788 -0.521 -2.373 0.00 0.00 H+0
ATOM 95 H 0 -11.654 -2.062 -1.493 0.00 0.00 H+0
ATOM 96 H 0 -13.128 -1.692 -2.419 0.00 0.00 H+0
ATOM 97 H 0 -14.390 -2.190 -0.272 0.00 0.00 H+0
ATOM 98 H 0 -12.864 -2.417 0.615 0.00 0.00 H+0
ATOM 99 H 0 -14.055 -1.223 1.185 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 104
CONECT 2 1 3 13 0 NONE 105
CONECT 3 2 12 4 5 NONE 106
CONECT 4 3 46 47 48 NONE 107
CONECT 5 3 6 7 8 NONE 108
CONECT 6 5 49 50 51 NONE 109
CONECT 7 5 52 53 54 NONE 110
CONECT 8 5 9 55 56 NONE 111
CONECT 9 8 10 11 12 NONE 112
CONECT 11 9 57 0 0 NONE 113
CONECT 12 9 3 58 59 NONE 114
CONECT 13 2 14 60 0 NONE 115
CONECT 14 13 15 61 0 NONE 116
CONECT 15 14 16 17 0 NONE 117
CONECT 16 15 62 63 64 NONE 118
CONECT 17 15 18 65 0 NONE 119
CONECT 18 17 19 66 0 NONE 120
CONECT 19 18 20 67 0 NONE 121
CONECT 20 19 21 22 0 NONE 122
CONECT 21 20 68 69 70 NONE 123
CONECT 22 20 23 71 0 NONE 124
CONECT 23 22 24 72 0 NONE 125
CONECT 24 23 25 73 0 NONE 126
CONECT 25 24 26 74 0 NONE 127
CONECT 26 25 27 28 0 NONE 128
CONECT 27 26 75 76 77 NONE 129
CONECT 28 26 29 78 0 NONE 130
CONECT 29 28 30 79 0 NONE 131
CONECT 30 29 31 80 0 NONE 132
CONECT 31 30 32 33 0 NONE 133
CONECT 32 31 81 82 83 NONE 134
CONECT 33 31 34 84 0 NONE 135
CONECT 34 33 35 85 0 NONE 136
CONECT 35 34 43 36 0 NONE 137
CONECT 36 35 37 38 0 NONE 138
CONECT 37 36 86 87 88 NONE 139
CONECT 38 36 39 89 90 NONE 140
CONECT 39 38 40 41 42 NONE 141
CONECT 41 39 91 0 0 NONE 142
CONECT 42 39 43 92 93 NONE 143
CONECT 43 42 44 35 45 NONE 144
CONECT 44 43 94 95 96 NONE 145
CONECT 45 43 97 98 99 NONE 146
END NONE 147
M END</inlineContents>
</jmolApplet>
</jmol>
'''Capsanthin rotatable structure'''

</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"
! {{general chemical data}} | {{PAGENAME}} 
|-
| align="center" colspan="2" bgcolor="#ffffff" | [[Image:Capsanthin_structure.GIF|{{PAGENAME}}]] 

|-
| [[IUPAC nomenclature|Systematic name]]
| (3R,3'S,S'R)-3,3'-dihydroxy-beta,kappa-caroten-6-one
|-
| [[Chemical formula|Molecular formula]]
| C40H56O3
|-
| [[Simplified molecular input line entry specification|SMILES]] 
| O=C([C@@]2(C)C(C)(C)C[C@H](O)C2)/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=[C@@](C)C[C@@H](O)CC(C)1C
|-
| [[Molecular weight]]
| 584.9gmol-1
|-
| [[Appearance]]
| Red oil (Dark)
|-
| [[CAS registry number|CAS number]]
| [465-42-9]
|-
| [[Merck Index]]
| ['''13''':1775]
|-
| [[Einecs number]]
| [207-364-1]
|-
| [[Solubility (in water)]]
| soluble
|-
| [[Stability]]
| Stable in ordinary conditions2
|-
|}

==''Antioxidant Power''==
- Definition: The ability to limit the damage caused by free radicals (damage due to oxygen)
Simply put, oxygen radicals are soluble in the body, and in particular like to attack DNA. Therefore using something like vitamen C, or in this case Capsanthin, these radicals can be 'scavanged'. The radical scavanging ability of Capsanthin is particularly good, and noted to be better than beta carotene and lutein. The number of conjugated double bonds, functional groups and chain structure are what control the antioxidant effects. It is believed that the antioxidant power of Capsanthin is enhanced by the conjugated keto groups present in its structure. Capsanthin was found to decompose more slowly than other carotenoids, indicating that its antioxidant effects may last longer than other carotenoids, and hence it is better than beta-carotene and lutein. That is to say it has a more effective radical scavanging ability. In addition, it was found that esterified Capsanthin was also a good antioxidant based on analysis of this radical scavanging ability3

==''Synthesis of Capsanthin''==
The synthesis of Capsanthin has been studied by Yamano and Ito from Kobe pharmaceutical University. Their method involves the Regio and stereoselective rearrangement of an epoxide that is tetrasubstituted by utilising a lewis acid. For the full journal concerning this synthesis, the following link can be pursued: http://www.jstage.jst.go.jp/article/cpb/49/12/1662/_pdf

Also, a particular xanthophyll found in green unripe peppers and many vegetables is violaxanthin. This contains an epoxide ring, and the properties associated with the epoxide allow contraction of the six-membered ring on violaxanthin to form the ring (5-membered) found in Capsanthin. Thus violaxanthin is a natural precursor of capsanthin.1 This type of reaction occurs during the ripening process of green peppers.

[[Image:Violaxanthin.GIF]]

'''Structure of violaxanthin'''

==''Analysis of Capsanthin''==
==''IR spectrum''==

[[Image:IR_of_Capsanthin2.GIF|{{PAGENAME}}]] 4

In the IR spectra above, only the end group that differentiates Capsanthin from other carotenoids is analysed. Quite clearly, the O-H is shown by the broad stretch at approximately 3300cm-1. The other characteristic peaks, notably C=O and C=C are shown on the spetra.

==''Nmr spectrum''==

Barber, Jackman, Warren and Weddon note that the nmr of Capsanthin contains methyl bands at 9.02, 8.95, 8.77, 8.65, 8.3 and 8.02ppm in the ratios of 1:2:1:1:1:4. It was deduced that the methyl groups present on the cyclohexane ring give rise to the bands at 8.95 and 8.3 as they are also observed in zeaxanthin, which also contains the cyclohexane ring. 8.02ppm refers to the four methyl groups present in the Capsanthin chain. The remaining bands at 9.02, 8.77 and 8.65 show evidence for non-allylic methyl groups on the cyclopentane ring. This spectrum is noted to be very similar to capsanthone and capsorubin with respect to the cyclopentane ring hydrogens.

==''References''==
1. http://www.herbalchem.net

2. http://www.chemexper.com

3. http://pubs.acs.org/cgi-bin/abstract.cgi/jafcau/1998/46/i09/abs/jf980200i.html

4. http://www3.interscience.wiley.com/cgi-bin/fulltext/95015751/PDFSTART