Azorubine

Chemical compound From Wikipedia, the free encyclopedia

Azorubine, also known as carmoisine, is an azo dye consisting of two naphthalene subunits.[1] It is a red solid. It is mainly used in foods that are heat-treated after fermentation. It has E number E122.[2]

Quick facts Names, Identifiers ...
Azorubine
Names
IUPAC name
disodium 4-hydroxy-3-[(E)-(4-sulfonato-1-naphthyl)diazenyl]naphthalene-1-sulfonate
Other names
  • carmoisine
  • Food Red 3
  • Azorubin S
  • Brillantcarmoisin O
  • Acid Red 14
  • C.I. 14720
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.020.598 Edit this at Wikidata
EC Number
  • 217-699-5
E number E122 (colours)
KEGG
UNII
  • InChI=1S/C20H14N2O7S2.2Na/c23-20-15-8-4-3-7-14(15)19(31(27,28)29)11-17(20)22-21-16-9-10-18(30(24,25)26)13-6-2-1-5-12(13)16;;/h1-11,23H,(H,24,25,26)(H,27,28,29);;/q;2*+1/p-2/b22-21+;; ☒N
    Key: YSVBPNGJESBVRM-ZPZFBZIMSA-L ☒N
  • InChI=1/C20H14N2O7S2.2Na/c23-20-15-8-4-3-7-14(15)19(31(27,28)29)11-17(20)22-21-16-9-10-18(30(24,25)26)13-6-2-1-5-12(13)16;;/h1-11,23H,(H,24,25,26)(H,27,28,29);;/q;2*+1/p-2/b22-21+;;
    Key: YSVBPNGJESBVRM-DGPRXMBVBS
  • c1ccc2c(c1)c(ccc2S(=O)(=O)[O-])/N=N/c3cc(c4ccccc4c3O)S(=O)(=O)[O-].[Na+].[Na+]
Properties
C20H12N2Na2O7S2
Molar mass 502.44
Appearance red powder
Melting point >300 °C (572 °F)
Soluble (120g/L)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Uses

In the US, this color was listed in 1939 as Ext. D&C Red No. 10[3] for use in externally applied drugs and cosmetics. It was delisted in 1963 because no party was interested in supporting the studies needed to establish safety. It was not used in food in the US.[4][5]

In the EU, azorubine is known as E number E122, and is authorized for use in certain foods and beverages, such as cheeses, dried fruit, and some alcoholic beverages,[6] and is permitted for use as an excipient in medications.[7]: 4 [8]: 16 

There are no provisions for azorubine in the Codex Alimentarius.[9]

Safety

Azorubine has shown no evidence of mutagenic or carcinogenic properties and an acceptable daily intake (ADI) of 0–4 mg/kg was established in 1983 by the WHO.[10]: 19  In rare instances, it may cause skin and respiratory allergic reactions even to FDA approved dosages.

No evidence supports broad claims that food coloring causes food intolerance and ADHD-like behavior in children.[11]: 452  It is possible that certain food coloring may act as a trigger in those who are genetically predisposed, but the evidence is weak.[4][12]

References

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