Sudan I

Sudan I
IUPAC name 1-phenylazonaphth-2-ol
Identifiers
CAS number	842-07-9
ChemSpider	10296256 Y
KEGG	C19525 Y
ChEBI	CHEBI:30958
Jmol-3D images	Image 1
SMILES Oc3ccc1ccccc1c3/N=N/c2ccccc2
InChI InChI=1S/C16H12N2O/c19-15-11-10-12-6-4-5-9-14(12)16(15)18-17-13-7-2-1-3-8-13/h1-11,19H/b18-17+ Y Key: MRQIXHXHHPWVIL-ISLYRVAYSA-N Y InChI=1/C16H12N2O/c19-15-11-10-12-6-4-5-9-14(12)16(15)18-17-13-7-2-1-3-8-13/h1-11,19H/b18-17+ Key: MRQIXHXHHPWVIL-ISLYRVAYBO
Properties
Molecular formula	C16H12N2O
Molar mass	248.28 g/mol
Melting point	131 °C
Y I (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Sudan I (also commonly known as CI Solvent Yellow 14 and Solvent Orange R), is a lysochrome, a diazo-conjugate dye with the 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 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.

Solvent yellow 14

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 the name of the dye be changed.^[4]

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

• Para Red
• Tartrazine

References

1. ^ http://monographs.iarc.fr/ENG/Classification/crthgr03.php
2. ^ 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. 
3. ^ Stiborová M, Martínek V, Rýdlová H, Hodek P, Frei E (October 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. http://cancerres.aacrjournals.org/cgi/pmidlookup?view=long&pmid=12384524. 
4. ^ "Sudan outraged at namesake dye". BBC. 2005-03-04. http://news.bbc.co.uk/1/hi/world/africa/4318419.stm. Retrieved 2008-09-08. 

External links

• BBC NEWS | Health | Food alert on cancer-causing dye
• Food Standards Agency - Sudan dyes