Sudan I

Sudan I
Names
	IUPAC name 1-(Phenyldiazenyl)naphthalen-2-ol
	Other names Solvent Yellow 14; C.I. Solvent Yellow 14; Solvent Orange R; 1-Phenylazo-2-naphthol;
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
Density	1.2g/cm3
Melting point	131 °C (268 °F; 404 K)
Boiling point	443.7 °C (830.7 °F; 716.8 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
Flash point	290.2 °C
	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 orange-red solid, used to color waxes, oils, petrol, solvents, and polishes. Historically, Sudan I used to serve as a food coloring agent, notably for curry powder and chili powder. However, along with its derivatives Sudan III and Sudan IV, the compound has been banned in many countries (including the United States and the European Union)^[3]^[4]^[5] due to its classification as a category 3 carcinogenic hazard by the International Agency for Research on Cancer (not classifiable due to its carcinogenicity to humans).^[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.
^ 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.
^ "List of Classifications - IARC Monographs". monographs.iarc.who.int. Retrieved 11 July 2024.

[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.

[pmid18418879-3] 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.

[4] 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.

[5] 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.

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

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[3]

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[6]

Names


IUPAC name 1-(Phenyldiazenyl)naphthalen-2-ol
Other names Solvent Yellow 14 C.I. Solvent Yellow 14 Solvent Orange R 1-Phenylazo-2-naphthol
Identifiers
CAS Number	842-07-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30958^Y
ChEMBL	ChEMBL1397023
ChemSpider	10296256^Y
ECHA InfoCard	100.011.517
EC Number	212-668-2
KEGG	C19525^N
PubChem CID	13297
UNII	48I7IBB68J^Y
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+^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
SMILES Oc3ccc1ccccc1c3/N=N/c2ccccc2
Properties
Chemical formula	C₁₆H₁₂N₂O
Molar mass	248.28 g/mol
Density	1.2g/cm³
Melting point	131 °C (268 °F; 404 K)
Boiling point	443.7 °C (830.7 °F; 716.8 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
Flash point	290.2 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

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Sudan I

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