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Sudan I

Sudan I
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.011.517 Edit this at Wikidata
EC Number
  • 212-668-2
KEGG
UNII
  • 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+ checkY
    Key: MRQIXHXHHPWVIL-ISLYRVAYSA-N checkY
  • 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
  • Oc3ccc1ccccc1c3/N=N/c2ccccc2
Properties
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)
−1.376×10−4 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazard
Warning
H317, H341, H351, H413
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).
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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 for use in food in many countries (including the United States and the European Union)[3][4][5] due to its classification as a category 3 carcinogen by the International Agency for Research on Cancer (not classifiable as to its carcinogenicity in 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.

  1. ^ "Substance Name: C.I. Solvent Yellow 14". ChemIDplus, Toxnet Database. Retrieved 15 March 2022.
  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 978-3-527-30673-2.
  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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