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Red 2G

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(Redirected from Azophloxin)
Red 2G
Skeletal formula of Red 2G as a sodium salt
Space-filling model of the Red 2G molecule as a sodium salt
Names
Other names
  • Acid Red 1
  • Food Red 10
  • Amidonaphthol red G
  • azogeranine
  • azophloxine
  • azofloxin
  • C.I. 18050
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.999 Edit this at Wikidata
E number E128 (colours)
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H15N3O8S2/c1-10(22)19-14-9-13(30(24,25)26)7-11-8-15(31(27,28)29)17(18(23)16(11)14)21-20-12-5-3-2-4-6-12/h2-9,23H,1H3,(H,19,22)(H,24,25,26)(H,27,28,29)/p-2/b21-20+Key: RSNSKUBBVCGSND-QZQOTICOSA-L
  • InChI=1/C18H15N3O8S2/c1-10(22)19-14-9-13(30(24,25)26)7-11-8-15(31(27,28)29)17(18(23)16(11)14)21-20-12-5-3-2-4-6-12/h2-9,23H,1H3,(H,19,22)(H,24,25,26)(H,27,28,29)/p-2/b21-20+Key: RSNSKUBBVCGSND-OLKPTRFBBB
SMILES
  • CC(=O)Nc2cc(cc3cc(c(/N=N/c1ccccc1)c(O)c23)S()(=O)=O)S()(=O)=O
Properties
Chemical formula C18H13N3O8S2
Molar mass 463.44 g·mol
Solubility in water 18 g/100 mL (20 °C)
Solubility 1 g/ 100 mL glycerol
Negligible in ethanol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Red 2G is a synthetic red azo dye. It is soluble in water and slightly soluble in glycerol. It usually comes as a disodium salt of 8-acetamido-1-hydroxy-2-phenylazonaphthalene-3,6 disulfonate.

Preparation

Red 2G is produced by azo coupling of Acetyl-H acid and diazonium derivative of Aniline under basic conditions:

Synthesis of Red 2G

Uses

Food dye

In the European Union, Red 2G was used as a food dye (E number E128). However, it was only permitted for use in breakfast sausages with a minimum cereal content of 6% and burger meat with a minimum vegetable and/or cereal content of 4%.

Following safety concerns raised by EFSA in its opinion of 5 July 2007, the European Commission has prepared a draft Regulation to suspend use of E128 as a food colouring. This proposed course of action was unanimously approved by European Union Member States at a meeting of the Standing Committee of the Food Chain and Animal Health (Section Toxicological Safety of the Food Chain) on 20 July 2007. and Commission Regulation (EC) No 884/2007 on emergency measures suspending the use of E 128 Red 2G as food colour was published in the Official Journal of the European Union on 27 July 2007.

Red 2G is also banned in Australia, Canada, Japan, Norway, and Malaysia. It was banned in Israel in July 2007 .

It is relatively insensitive to the bleaching effect of sulfur dioxide (E220) and sodium metabisulfite (E223). In the intestines, Red 2G can be converted to the toxic compound aniline, so there are concerns Red 2G may ultimately interfere with blood haemoglobin, as well as cause cancer.

Inks

It is also used as a dye for coatings, inks, paper, crepe paper, and fine tissue.

Histology

Red 2G can be also used for staining in histology, though rarely, e.g. as a component of Masson's trichrome.

Potential health risks

In July 2007, the EFSA established that E128 is potentially carcinogenic because it forms aniline in the body when consumed. The pressure group, The Food Commission, said there had been concerns about Red 2G going back decades and it was suspected of being a carcinogen in the 1980s.

References

  1. H.E. Fierz-David, L. Blangey (1949), Fundamental Processes of Dye Chemistry, Translation of the 5. Austrian Edition by P.W. Vittum, Interscience Publishers, Inc., New York, pp. 263–264
  2. "European Parliament and council directive 94/36/EC of june 1994 on colours for use in foodstuffs" (PDF). Archived from the original (PDF) on 2009-02-06. Retrieved 2007-07-10.
  3. "EFSA re-evaluates safety of food colours and adopts first opinion: Food colour Red 2G raises potential safety concerns". 9 July 2007.
  4. "Novel Food and Toxicological Safety - Food Safety - European Commission" (PDF). Food Safety.
  5. "Official Journal of the European Union". eur-lex.europa.eu. 27 July 2007. Retrieved 12 June 2023.
  6. "Mattilsynet". Archived from the original on 2012-08-04. Retrieved 2007-12-11.
  7. "Dye used in burgers and sausages banned". Retrieved 12 June 2023.
  8. Hickman, Martin (10 July 2007). "Additive used in sausages and burgers may cause cancer". The Independent. London. Archived from the original on 2008-05-22. Retrieved 22 May 2010.
  9. "Sausage additive linked to cancer". 10 July 2007 – via news.bbc.co.uk.
  10. Hickman, Martin (10 July 2007). "Additive used in sausages and burgers may cause cancer". The Independent. London. Archived from the original on July 12, 2007. Retrieved 2007-07-10.
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