Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Sudan III: Difference between pages

| 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-<nowiki/>{[4-(Phenyldiazenyl)phenyl]diazenyl}naphthalen-2-ol

| 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}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 82535

| ChEMBL = 2001927

| PubChem = 62331

| 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

| Hazards_ref=<ref>{{cite web |title=Safety Data Sheet Sudan III |url=https://www.fishersci.com/store/msds?partNumber=S25593&productDescription=SUDAN+III+10G&vendorId=VN00115888&countryCode=US&language=en |website=fishersci.com |access-date=24 August 2020}}</ref>

| 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]].<ref name="Ullmann">{{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}}</ref>

==Uses==

It is used to color nonpolar substances such as [[oil]]s, [[fat]]s, [[wax]]es, [[Grease (lubricant)|grease]]s, various [[hydrocarbon]] products, and [[Acrylyl group|acrylic]] [[emulsion]]s. 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.<ref>{{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 }}</ref> The IRS requires "a concentration spectrally equivalent to at least 3.9&nbsp;pounds of... Solvent Red 26 per thousand barrels of fuel" ({{convert|0.0039|lb/oilbbl|mg/L|1|disp=out}});<ref>{{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}}</ref> the concentrations required by EPA are roughly 5 times lower. It should be stored at room temperature.<ref name="sas">{{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}}</ref>

===Biological staining===

Sudan III is a dye used for [[Sudan stain]]ing. Similar dyes include [[Oil Red O]], [[Sudan IV]], and [[Sudan Black B]]. They are used for [[Staining (biology)|staining]] of [[triglycerides]] in frozen sections, and some protein bound [[lipids]] and [[lipoproteins]] on [[Paraffin wax|paraffin]] sections. It has the appearance of reddish brown crystals and a maximum absorption at 507(304) nm.<ref>R. D. Lillie. Conn's Biological Stains. Williams & Wilkins, Baltimore, MD., U.S.A.</ref> 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.<ref name=sas/>

==Safety==

[[Sudan I]], Sudan III, and [[Sudan IV]] have been classified as category 3 [[carcinogen]]s by the [[International Agency for Research on Cancer]].<ref name="pmid18418879">{{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 }}</ref>

==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}}

[[Category:Azo dyes]]

[[Category:Staining dyes]]

[[Category:Sudan dyes]]

[[Category:IARC Group 3 carcinogens]]

[[Category:2-Naphthols]]

[[Category:Fuel dyes]]