Azorubine

"E122" redirects here. For the chemical element, see unbibium.

Azorubine
Names
IUPAC name
disodium 4-hydroxy-2-[(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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Azorubine 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]

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.[1]

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

  1. ^ Klaus Hunger; Peter Mischke; Wolfgang Rieper; et al. (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245. ISBN 978-3527306732.
  2. ^ Pubchem entry
  3. ^ Regulatory Status of Color Additives: Ext. D&C Red No. 10
  4. ^ a b FDA. Background Document for the Food Advisory Committee: Certified Color Additives in Food and Possible Association with Attention Deficit Hyperactivity Disorder in Children: March 30-31, 2011
  5. ^ FDA. 9 November 2008. Food and Drug Administration, Compliance Program Guidance Manual, Chapter 03 - Foodborne Biological Hazards p37
  6. ^ Azorubine entry in EU Food Additive Database Archived 11 December 2014 at the Wayback Machine Accessed 6 December 2014
  7. ^ EU. 19 June 2007 Guideline on Excipients in the Dossier for Application for Marketing Authorisation of a Medicinal Product
  8. ^ Directive 94/36/EC - European Commission
  9. ^ Azorubine (Carmoisine) (122) in the GSFA Online Database Accessed 6 December 2014
  10. ^ WHO, 1983. Evaluation of certain food additives and contaminants. Linked from WHO listing here
  11. ^ Tomaska LD and Brooke-Taylor, S. Food Additives - General pp 449-454 in Encyclopedia of Food Safety, Vol 2: Hazards and Diseases. Eds, Motarjemi Y et al. Academic Press, 2013. ISBN 9780123786135
  12. ^ Millichap JG; Yee MM (February 2012). "The diet factor in attention-deficit/hyperactivity disorder". Pediatrics. 129 (2): 330–337. doi:10.1542/peds.2011-2199. PMID 22232312. S2CID 14925322.