Sudan III
A sample of dye Sudan III
Sudan III
Names
Preferred IUPAC name
1-{[4-(Phenyldiazenyl)phenyl]diazenyl}naphthalen-2-ol
Other names
Sudan Red BK, Fat Ponceau G, Cerasin Red, C.I. 26100, Solvent Red 23, Solvent Red 164, Sudan Red, Sudan Red III, Sudan V, Sudan Red B, Sudan G, Scarlet B, and Tony Red
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.490
KEGG
UNII
  • InChI=1S/C22H16N4O/c27-21-15-10-16-6-4-5-9-20(16)22(21)26-25-19-13-11-18(12-14-19)24-23-17-7-2-1-3-8-17/h1-15,27H/b24-23-,26-25+ checkY
    Key: FHNINJWBTRXEBC-HXEHWPEMSA-N checkY
  • InChI=1/C22H16N4O/c27-21-15-10-16-6-4-5-9-20(16)22(21)26-25-19-13-11-18(12-14-19)24-23-17-7-2-1-3-8-17/h1-15,27H/b24-23-,26-25+
    Key: FHNINJWBTRXEBC-HXEHWPEMBU
  • Oc4ccc1ccccc1c4/N=N/c3ccc(\N=N/c2ccccc2)cc3
Properties
C22H16N4O
Molar mass 352.397 g·mol−1
Melting point 199 °C (390 °F; 472 K)
Hazards[1]
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation mark
Warning
H315, H318, H319, H335, H413
P101, P102, P103, P261, P264, P270, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Safety data sheet (SDS) Sigma-Aldrich Sudan III
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sudan III is a lysochrome (fat-soluble dye) diazo dye. It is structurally related to azobenzene.[2]

Uses

It is used to color nonpolar substances such as oils, fats, waxes, greases, various hydrocarbon products, and acrylic emulsions. Its main use is as a fuel dye in the United States of America mandated by the Internal Revenue Service (IRS) to distinguish low-taxed heating oil from automotive diesel fuel, and by the United States Environmental Protection Agency (EPA) to mark fuels with higher sulfur content; it is a replacement for Solvent Red 26 with better solubility in hydrocarbons.[3] The IRS requires "a concentration spectrally equivalent to at least 3.9 pounds of... Solvent Red 26 per thousand barrels of fuel" (11.1 mg/L);[4] the concentrations required by EPA are roughly 5 times lower. It should be stored at room temperature.[5]

Biological staining

Sudan III is a dye used for Sudan staining. Similar dyes include Oil Red O, Sudan IV, and Sudan Black B. They are used for staining of triglycerides in frozen sections, and some protein bound lipids and lipoproteins on paraffin sections. It has the appearance of reddish brown crystals and a maximum absorption at 507(304) nm.[6] It has a more orange shade than Oil Red O, lending to its less popular status. In botany, it is used with Light Green SF Yellowish to differentiate between suberized and cutinized plant tissue.[5]

Safety

Sudan I, Sudan III, and Sudan IV have been classified as category 3 carcinogens by the International Agency for Research on Cancer.[7]

References

  1. ↑ "Safety Data Sheet Sudan III". fishersci.com. Retrieved 24 August 2020.
  2. ↑ Hunger, Klaus; Mischke, Peter; Rieper, Wolfgang; Raue, Roderich; Kunde, Klaus; Engel, Aloys (2005). "Azo Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_245. ISBN 978-3527306732.
  3. ↑ "L2_3_9_rf". Archived from the original on 2005-05-10. Retrieved 2006-02-02.
  4. ↑ "Publication 510: Excise Taxes (Including Fuel Tax Credits and Refunds)" (PDF). IRS.gov. February 2020. p. 9. Retrieved February 10, 2021.
  5. 1 2 "Sudan III" (PDF). Sigma Aldrich. Retrieved 15 February 2023.
  6. ↑ R. D. Lillie. Conn's Biological Stains. Williams & Wilkins, Baltimore, MD., U.S.A.
  7. ↑ 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. S2CID 206010951.
  • Susan Budavari, Editor, (1996). The Merck Index, Ed. 12. Merck & Co., Inc., Whitehouse Station, NJ, USA
  • Edward Gurr, (1971). Synthetic Dyes in Biology, Medicine and Chemistry. Academic Press, London, England.
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