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Wikipedia

Sudan III

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

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
  • 85-86-9 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:82535 Y
ChEMBL
  • ChEMBL2001927
ChemSpider
  • 16736189 Y
ECHA InfoCard 100.001.490
KEGG
  • C19527 Y
  • 62331
UNII
  • ND733RX3JN Y
  • DTXSID3041742
  • 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+ Y
    Key: FHNINJWBTRXEBC-HXEHWPEMSA-N Y
  • 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:
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).
N verify (what is YN ?)

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.

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.[5]

Safety

Sudan I, Sudan III, and Sudan IV have been classified as category 3 carcinogens by the International Agency for Research on Cancer.[6]

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.
  3. ^ . 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. ^ R. D. Lillie. Conn's Biological Stains. Williams & Wilkins, Baltimore, MD., U.S.A.
  6. ^ 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.

External links

  • Stains File entry

sudan, lysochrome, soluble, diazo, structurally, related, azobenzene, namespreferred, iupac, name, phenyldiazenyl, phenyl, diazenyl, naphthalen, olother, names, sudan, ponceau, cerasin, 26100, solvent, solvent, sudan, sudan, sudan, sudan, sudan, scarlet, tony,. Sudan III is a lysochrome fat soluble dye diazo dye It is structurally related to azobenzene 2 Sudan III NamesPreferred IUPAC name 1 4 Phenyldiazenyl phenyl diazenyl naphthalen 2 olOther 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 RedIdentifiersCAS Number 85 86 9 Y3D model JSmol Interactive imageChEBI CHEBI 82535 YChEMBL ChEMBL2001927ChemSpider 16736189 YECHA InfoCard 100 001 490KEGG C19527 YPubChem CID 62331UNII ND733RX3JN YCompTox Dashboard EPA DTXSID3041742InChI 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 YKey FHNINJWBTRXEBC HXEHWPEMSA N YInChI 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 HXEHWPEMBUSMILES Oc4ccc1ccccc1c4 N N c3ccc N N c2ccccc2 cc3PropertiesChemical formula C 22H 16N 4OMolar mass 352 397 g mol 1Melting point 199 C 390 F 472 K Hazards 1 GHS labelling PictogramsSignal word WarningHazard statements H315 H318 H319 H335 H413Precautionary statements 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 P501Safety data sheet SDS Sigma Aldrich Sudan IIIExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Uses 1 1 Biological staining 2 Safety 3 References 4 External linksUses EditIt 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 Biological staining Edit 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 5 Safety EditSudan I Sudan III and Sudan IV have been classified as category 3 carcinogens by the International Agency for Research on Cancer 6 References Edit Safety Data Sheet Sudan III fishersci com Retrieved 24 August 2020 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 L2 3 9 rf Archived from the original on 2005 05 10 Retrieved 2006 02 02 Publication 510 Excise Taxes Including Fuel Tax Credits and Refunds PDF IRS gov February 2020 p 9 Retrieved February 10 2021 R D Lillie Conn s Biological Stains Williams amp Wilkins Baltimore MD U S A 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 amp Co Inc Whitehouse Station NJ USA Edward Gurr 1971 Synthetic Dyes in Biology Medicine and Chemistry Academic Press London England External links EditStains File entry Retrieved from https en wikipedia org w index php title Sudan III amp oldid 1111488275, wikipedia, wiki, book, books, library,

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