Sudan I

Sudan I
Names
	IUPAC name 1-(Phenyldiazenyl)naphthalen-2-ol
Identifiers
CAS Number	842-07-9 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30958 ;
ChEMBL	ChEMBL1397023;
ChemSpider	10296256 ;
ECHA InfoCard	100.011.517
EC Number	212-668-2;
KEGG	C19525 ;
PubChem CID	13297;
UNII	48I7IBB68J ;
CompTox Dashboard (EPA)	DTXSID90873447 DTXSID4021135, DTXSID90873447 ;
	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+ Key: MRQIXHXHHPWVIL-ISLYRVAYSA-N ; 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;
	SMILES Oc3ccc1ccccc1c3/N=N/c2ccccc2;
Properties
Chemical formula	C16H12N2O
Molar mass	248.28 g/mol
Melting point	131 °C (268 °F; 404 K)
Magnetic susceptibility (χ)	−1.376×10−4 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H317, H341, H351, H413
Precautionary statements	P201, P202, P261, P272, P273, P280, P281, P302+P352, P308+P313, P321, P333+P313, P363, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Sudan I (also known as CI Solvent Yellow 14 or Solvent Orange R)^[1] is an organic compound, typically classified as an azo dye.^[2] It is an intensely orange-red solid that is added to colorize waxes, oils, petrol, solvents, and polishes. Historically, Sudan I has also acted as a food coloring agent, especially for curry powder and chili powder. Owing to its classification as a category 3 carcinogenic hazard by the International Agency for Research on Cancer (not classifiable as to its carcinogenicity to humans),^[3] Sudan I (as well as its derivatives Sudan III and Sudan IV) has been banned in many countries including the United States and European Union.^[4]^[5]^[6] Nevertheless, Sudan I remains valuable as a coloring reagent for non-food-related uses, such as in the formulation of orange-colored smoke.

^ "Substance Name: C.I. Solvent Yellow 14". ChemIDplus, Toxnet Database. Retrieved 15 March 2022.
^ Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; et al. (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245. ISBN 978-3527306732.
^ "List of Classifications - IARC Monographs". monographs.iarc.who.int. Retrieved 11 July 2024.
^ Refat NA, Ibrahim ZS, Moustafa GG, et al. (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. S2CID 206010951.
^ Pan, Hongmiao; Feng, Jinhui; He, Gui-Xin; Cerniglia, Carl E.; Chen, Huizhong (May 2012). "Evaluation of impact of exposure of Sudan azo dyes and their metabolites on human intestinal bacteria". Anaerobe. 18 (4): 445–453. doi:10.1016/j.anaerobe.2012.05.002. ISSN 1075-9964. PMC 5870115. PMID 22634331.
^ Genualdi, Susie; MacMahon, Shaun; Robbins, Katherine; Farris, Samantha; Shyong, Nicole; DeJager, Lowri (April 2016). "Method development and survey of Sudan I–IV in palm oil and chilli spices in the Washington, DC, area". Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 33 (4): 583–591. doi:10.1080/19440049.2016.1147986. ISSN 1944-0049. PMC 4888373. PMID 26824489.

[1] "Substance Name: C.I. Solvent Yellow 14". ChemIDplus, Toxnet Database. Retrieved 15 March 2022.

[Ullmann-2] Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; et al. (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245. ISBN 978-3527306732.

[3] "List of Classifications - IARC Monographs". monographs.iarc.who.int. Retrieved 11 July 2024.

[pmid18418879-4] Refat NA, Ibrahim ZS, Moustafa GG, et al. (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. S2CID 206010951.

[5] Pan, Hongmiao; Feng, Jinhui; He, Gui-Xin; Cerniglia, Carl E.; Chen, Huizhong (May 2012). "Evaluation of impact of exposure of Sudan azo dyes and their metabolites on human intestinal bacteria". Anaerobe. 18 (4): 445–453. doi:10.1016/j.anaerobe.2012.05.002. ISSN 1075-9964. PMC 5870115. PMID 22634331.

[6] Genualdi, Susie; MacMahon, Shaun; Robbins, Katherine; Farris, Samantha; Shyong, Nicole; DeJager, Lowri (April 2016). "Method development and survey of Sudan I–IV in palm oil and chilli spices in the Washington, DC, area". Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment. 33 (4): 583–591. doi:10.1080/19440049.2016.1147986. ISSN 1944-0049. PMC 4888373. PMID 26824489.

[1]

[2]

[3]

[4]

[5]

[6]