Sudan III
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 470483022
| Name = Sudan III
| ImageFile1 =AW Sudan III.jpg
| ImageName1 = A sample of dye Sudan III
| ImageFile2 = Solvent Red 23.svg
| ImageSize2 = 200px
| ImageName2 = Sudan III
| PIN = 1-
| OtherNames = 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
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 16736189
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 82535
| ChEMBL = 2001927
| PubChem = 62331
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = ND733RX3JN
| 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+
| InChIKey = FHNINJWBTRXEBC-HXEHWPEMBU
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FHNINJWBTRXEBC-HXEHWPEMSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 85-86-9
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C19527
| SMILES = Oc4ccc1ccccc1c4/N=N/c3ccc(\N=N/c2ccccc2)cc3
}}
|Section2={{Chembox Properties
| C=22|H=16|N=4|O=1
| Density =
| MeltingPtC = 199
| BoilingPt =
}}
| Section7 = {{Chembox Hazards
| ExternalSDS = [https://archive.org/details/print-msdsaction-1 Sigma-Aldrich Sudan III]
| PPhrases = {{P-phrases|101|102|103|270|261|264|271|273|280|302+352|304+340|305+351+338|310|312|321|332+313|337+313|362|403+233|405|501}}
| GHSPictograms = {{GHS05}}{{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|318|319|335|413}}
}}
}}
Sudan III is a lysochrome (fat-soluble dye) diazo dye. It is structurally related to azobenzene.{{Ullmann|first1 = Klaus|last1 = Hunger|first2 = Peter|last2 = Mischke|first3 = Wolfgang|last3 = Rieper|first4 = Roderich|last4 = Raue|first5 = Klaus|last5 = Kunde|first6 = Aloys|last6 = Engel|display-authors=3|title = Azo Dyes|year = 2005|doi = 10.1002/14356007.a03_245}}
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 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.{{cite web |url=http://www.chevron.com/products/prodserv/fuels/bulletin/diesel/L2_3_9_rf.htm |title=L2_3_9_rf |access-date=2006-02-02 |url-status=dead |archive-url=https://web.archive.org/web/20050510225159/http://www.chevron.com/products/prodserv/fuels/bulletin/diesel/L2_3_9_rf.htm |archive-date=2005-05-10 }} The IRS requires "a concentration spectrally equivalent to at least 3.9 pounds of... Solvent Red 26 per thousand barrels of fuel" ({{convert|0.0039|lb/oilbbl|mg/L|1|disp=out}});{{cite web |url=https://www.irs.gov/pub/irs-pdf/p510.pdf |title=Publication 510: Excise Taxes (Including Fuel Tax Credits and Refunds) |date=February 2020 |work=IRS.gov |accessdate=February 10, 2021 |page=9}} the concentrations required by EPA are roughly 5 times lower. It should be stored at room temperature.{{cite web |title=Sudan III |url=https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/product/documents/225/689/s4131pis.pdf |website=Sigma Aldrich |access-date=15 February 2023}}
=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.R. D. Lillie. Conn's Biological Stains. Williams & Wilkins, Baltimore, MD., U.S.A. 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.
Safety
Sudan I, Sudan III, and Sudan IV have been classified as category 3 carcinogens by the International Agency for Research on Cancer.{{cite journal |vauthors=Refat NA, Ibrahim ZS, Moustafa GG, Sakamoto KQ, Ishizuka M, Fujita S |display-authors=3|title=The induction of cytochrome P450 1A1 by Sudan dyes |journal=J. Biochem. Mol. Toxicol. |volume=22 |issue=2 |pages=77–84 |year=2008 |pmid=18418879 |doi=10.1002/jbt.20220 |s2cid=206010951 }}
References
{{Reflist}}
- 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
- [http://stainsfile.info/StainsFile/dyes/26100.htm Stains File] entry
{{Stains}}