Azorubine

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
  • E122
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+;; X markN
    Key: YSVBPNGJESBVRM-ZPZFBZIMSA-L X markN
  • 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, also known as carmoisine, is an azo dye consisting of two naphthalene subunits. It is a red solid. It is mainly used in foods that are heat-treated after fermentation. It has E number E122.

Uses

In the US, this color was listed in 1939 as Ext. D&C Red No. 10 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.

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, and is permitted for use as an excipient in medications.: 4 : 16 

There are no provisions for azorubine in the Codex Alimentarius.

Safety

The Joint FAO/WHO Expert Committee on Food Additives (JECFA) established an acceptable daily intake (ADI) for azorubine of 0–4 mg/kg of body weight per day in 1983. In 2009, the European Food Safety Authority (EFSA) re-evaluated azorubine and retained the 4 mg/kg ADI, concluding that the available data showed no concern regarding genotoxicity and that evidence was insufficient to establish that azorubine directly induces sensitivity reactions.

Azorubine is one of the "Southampton Six", a group of six synthetic food colors that also includes tartrazine (E102), quinoline yellow (E104), sunset yellow (E110), Ponceau 4R (E124), and Allura red (E129). In a 2007 study by researchers at the University of Southampton, the colors were tested across two distinct mixtures containing sodium benzoate; azorubine was one of two colors included in both trial mixtures. EFSA reviewed the trial in 2008 and concluded that it provided limited evidence of a small effect of the tested mixtures on activity and attention in some children, but that the trial design could not identify which individual additives were responsible.

Under Article 24 and Annex V of Regulation (EC) No 1333/2008, foods sold in the European Union containing azorubine must carry the color's name or E number accompanied by the warning statement that it "may have an adverse effect on activity and attention in children".

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 978-3-527-30673-2.
  2. ↑ Pubchem entry
  3. ↑ Regulatory Status of Color Additives: Ext. D&C Red No. 10
  4. ↑ 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[dead link] 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. ↑ "Azorubine". JECFA database. World Health Organization. Retrieved 17 September 2026.
  11. ↑ EFSA Panel on Food Additives and Nutrient Sources Added to Food (2009). "Scientific Opinion on the re-evaluation of Azorubine/Carmoisine (E 122) as a food additive". EFSA Journal. 7 (11): 1332. doi:10.2903/j.efsa.2009.1332.
  12. ↑ "Evaluation of the progress made by Scottish SMEs with the voluntary withdrawal of the 'Southampton Six' Colours from food products". Food Standards Scotland. 1 September 2010. Retrieved 17 September 2026.
  13. ↑ McCann, Donna; Barrett, Angelina; Cooper, Alison; et al. (2007). "Food additives and hyperactive behaviour in 3-year-old and 8/9-year-old children in the community: a randomised, double-blinded, placebo-controlled trial". The Lancet. 370 (9598): 1560–1567. doi:10.1016/S0140-6736(07)61306-3. PMID 17825405.
  14. ↑ European Food Safety Authority (2008). "Assessment of the results of the study by McCann et al. (2007) on the effect of some colours and sodium benzoate on children's behaviour". EFSA Journal. 6 (3): 660. doi:10.2903/j.efsa.2008.660.
  15. ↑ "Regulation (EC) No 1333/2008 of the European Parliament and of the Council of 16 December 2008 on food additives". EUR-Lex. European Union. Article 24 and Annex V. Retrieved 17 September 2026.