Sudan I
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| Names | |
|---|---|
| IUPAC name
1-phenylazo-2-naphthol
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| Identifiers | |
3D model (JSmol)
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| ECHA InfoCard | 100.011.517 |
CompTox Dashboard (EPA)
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| Properties | |
| C16H12N2O | |
| Molar mass | 248.28 g/mol |
| Melting point | 131 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sudan I (also commonly known as CI Solvent Yellow 14 and Solvent Orange R), is a lysochrome, an diazo-conjugate dye with a chemical formula of 1-phenylazo-2-naphthol. Sudan I is a powdered substance with an orange-red appearance. The additive is mainly used to colour waxes, oils, petrol, solvents and polishes. Sudan I has also been adopted for colouring various foodstuffs, including particular brands of curry powder and chili powder, although the use of Sudan I in foods is now banned in many countries because Sudan I, Sudan III, and Sudan IV have been classified as category 3 carcinogens (Not classifiable as to its carcinogenicity to humans[1]) by the International Agency for Research on Cancer.[2]
Sudan I is still used in some orange coloured smoke formulations and as a colouring for cotton refuse used in chemistry experiments.
Toxicology
Sudan I is a rodent carcinogen[citation needed] — laboratory tests on rats showed growth of cancerous tumours in the liver and bladder. These tests have led to the additive being banned from use in foods throughout the EU, as it may pose an increased risk of cancer.
Comparisons between experimental animals and human Cytochrome P450 (CYP) strongly suggest that animal carcinogenicity data can be extrapolated to humans.[3]
Sudan I is also present as an impurity in Sunset Yellow, which is its disulfonated water-soluble version.
Food scare
In February 2005, Sudan I became a prominent news topic, particularly in the United Kingdom. A Worcestershire sauce produced by Premier Foods was found to be contaminated by the carcinogenic dye. The origin was traced to adulterated chili powder. The sauce was used in hundreds of supermarket products such as pizzas and ready-made meals, and the contamination led to over 400 products being taken off the shelves. In South Africa, Sudan I traces were found in several spices (Robertson's Peri-Peri Sauce and two Taj Mahal spice products) in 2005 and 2007.
Due to the scare, the government of Sudan requested that the name of the dye be changed.[4] The name was probably originally given due to the association of the dye's red color with an (at that time) exotic country.
Synonyms and brand names
- Atul Orange R
- Benzene-1-azo-2-naphthol
- Brasilazina oil Orange
- Brilliant oil Orange R
- Calcogas M
- Calcogas Orange NC
- Calco oil Orange 7078
- Campbelline oil Orange
- Carminaph
- Ceres Orange R
- CerotinOrange G
- CI Solvent Yellow 14
- C.I. Solvent Yellow 14
- Dispersol Yellow PP
- Dunkelgelb
- Enial Orange I
- Fast oil Orange
- Fast oil Orange I
- Fast Orange
- Fat Orange I
- Fett Orange 4A
- Grasal Orange
- Grasan Orange R
- Hidaco oil Orange
- Lacquer Orange VG
- MotiOrange R
- Oil Orange
- Oleal Orange R
- Orange à l'huile
- Orange insoluble OLG
- Orange 3RA soluble in grease
- Orange resenole No. 3
- Orange R fat soluble
- Organol Orange
- Orient oil Orange PS
- Petrol Orange Y
- 1-(Phenylazo)-2-naphthol
- Plastoresin Orange F4A
- PyronalOrange
- Resinol Orange R
- Resoform Orange G
- Sansei Orange G
- Scharlach B
- Silotras Orange TR
- Solvent Yellow 14
- Somalia Orange I
- Sudan I
- SpiritOrange
- Spirit Orange
- Spirit Yellow I
- Stearix Orange
- Sudan J
- Sudan Orange R
- Sudan Orange RA
- Sudan Orange RA new
- Tertrogras Orange SV
- Toyo Oil Orange
- Waxakol Orange GL
- Waxoline Yellow I
- Waxoline Yellow IM
- Waxoline Yellow IP
- Waxoline Yellow IS
See also
References
- ^ http://monographs.iarc.fr/ENG/Classification/crthgr03.php
- ^ Refat NA, Ibrahim ZS, Moustafa GG, Sakamoto KQ, Ishizuka M, Fujita S (2008). "The induction of cytochrome P450 1A1 by sudan dyes". J. Biochem. Mol. Toxicol. 22 (2): 77–84. doi:10.1002/jbt.20220. PMID 18418879.
{{cite journal}}: CS1 maint: multiple names: authors list (link) - ^ Stiborová M, Martínek V, Rýdlová H, Hodek P, Frei E (2002). "Sudan I is a potential carcinogen for humans: evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes". Cancer Res. 62 (20): 5678–84. PMID 12384524.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ "Sudan outraged at namesake dye". BBC. Retrieved 2008-09-08.