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Revision as of 18:09, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 445470826 of page Sudan_IV for the Chem/Drugbox validation project (updated: 'KEGG', 'CASNo').		Latest revision as of 13:47, 9 April 2024 edit Skoot13 (talk | contribs)Extended confirmed users1,873 edits ce
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	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 434006584
			| Watchedfields = changed
		⚫	| verifiedrevid = 470472512
	| Name = Sudan IV		| Name = Sudan IV
	| ImageFile = Sudan IV.svg		| ImageFile = Sudan IV.svg
	| ImageSize = 250		| ImageSize = 250
			| PIN = 1-phenyl}diazenyl]naphthalen-2-ol
	| IUPACName =
		⚫	| OtherNames = 1-<nowiki/>{2-Methyl-4-phenyl}azonaphthalen-2-ol<br />Sudan R, C.I. Solvent Red 24, C.I. 26105, Lipid Crimson, Oil Red, Oil Red BB, Fat Red B, Oil Red IV, Scarlet Red, Scarlet Red N.F, Scarlet Red Scharlach, Scarlet R
	| SystematicName =
		⚫	|Section1={{Chembox Identifiers
⚫	| OtherNames = Sudan R, C.I. Solvent Red 24, C.I. 26105, Lipid Crimson, Oil Red, Oil Red BB, Fat Red B, Oil Red IV, Scarlet Red, Scarlet Red N.F, Scarlet Red Scharlach, Scarlet R
			| CASNo_Ref = {{cascite|changed|??}}
⚫	| Section1 = {{Chembox Identifiers
			| CASNo = 85-83-6
	| Abbreviations =		| Abbreviations =
		⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| ChEBI = 88014
			| ChEMBL = 1707454
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 11252033		| ChemSpiderID = 11252033
		⚫	| EINECS = 201-635-8
		⚫	| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = C19520
		⚫	| PubChem = 62330
		⚫	| RTECS =
		⚫	| MeSHName =
			| UNII = I35E9QU96C
	| InChI = 1S/C24H20N4O/c1-16-7-3-6-10-21(16)26-25-19-12-13-22(17(2)15-19)27-28-24-20-9-5-4-8-18(20)11-14-23(24)29/h3-15,29H,1-2H3/b26-25+,28-27+		| InChI = 1S/C24H20N4O/c1-16-7-3-6-10-21(16)26-25-19-12-13-22(17(2)15-19)27-28-24-20-9-5-4-8-18(20)11-14-23(24)29/h3-15,29H,1-2H3/b26-25+,28-27+
	| InChIKey = RCTGMCJBQGBLKT-PAMTUDGEBE		| InChIKey = RCTGMCJBQGBLKT-PAMTUDGEBE
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	| StdInChIKey = RCTGMCJBQGBLKT-PAMTUDGESA-N		| StdInChIKey = RCTGMCJBQGBLKT-PAMTUDGESA-N
	| InChIKey1 = RCTGMCJBQGBLKT-PAMTUDGESA-N		| InChIKey1 = RCTGMCJBQGBLKT-PAMTUDGESA-N
	| CASNo = <!-- blanked - oldvalue: 85-83-6 -->
⚫	| EINECS =
	| EINECSCASNO =
⚫	| PubChem =
	| SMILES = Cc4ccccc4/N=N/c3ccc(/N=N/c1c2ccccc2ccc1O)c(C)c3		| SMILES = Cc4ccccc4/N=N/c3ccc(/N=N/c1c2ccccc2ccc1O)c(C)c3
			}}
	| InChI =
		⚫	|Section2={{Chembox Properties
⚫	| RTECS =
⚫	| MeSHName =
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
⚫	| ChEBI =
⚫	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = <!-- blanked - oldvalue: C19520 -->
	| ATCCode_prefix =
	| ATCCode_suffix =
	| ATC_Supplemental =}}
⚫	| Section2 = {{Chembox Properties
	| Formula = C<sub>24</sub>H<sub>20</sub>N<sub>4</sub>O		| Formula = C<sub>24</sub>H<sub>20</sub>N<sub>4</sub>O
	| MolarMass =		| MolarMass =
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	| Density =		| Density =
	| MeltingPt =		| MeltingPt =
	| Melting_notes =		| MeltingPt_notes =
	| BoilingPt =		| BoilingPt =
	| Boiling_notes =		| BoilingPt_notes =
	| Solubility =		| Solubility =
	| SolubleOther =		| SolubleOther =
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	| pKa =		| pKa =
	| pKb = }}		| pKb = }}
	| Section3 = {{Chembox Structure		|Section3={{Chembox Structure
	| CrystalStruct =		| CrystalStruct =
	| Coordination =		| Coordination =
	| MolShape = }}		| MolShape = }}
	| Section4 = {{Chembox Thermochemistry		|Section4={{Chembox Thermochemistry
	| DeltaHf =		| DeltaHf =
	| DeltaHc =		| DeltaHc =
	| Entropy =		| Entropy =
	| HeatCapacity = }}		| HeatCapacity = }}
	| Section5 = {{Chembox Pharmacology		|Section7={{Chembox Hazards
			| GHSPictograms = {{GHS07}}
	| AdminRoutes =
			| GHSSignalWord = Warning
	| Bioavail =
			| HPhrases = {{H-phrases|315|319}}
	| Metabolism =
			| PPhrases = {{P-phrases|264|280|302+352|305+351+338|321|332+313|337+313|362}}
	| HalfLife =
	| ProteinBound =		| ExternalSDS =
	| Excretion =
	| Legal_status =
	| Legal_US =
	| Legal_UK =
	| Legal_AU =
	| Legal_CA =
	| PregCat =
	| PregCat_AU =
	| PregCat_US = }}
	| Section6 = {{Chembox Explosive
	| ShockSens =
	| FrictionSens =
	| ExplosiveV =
	| REFactor = }}
	| Section7 = {{Chembox Hazards
	| ExternalMSDS =
	| EUClass =
	| EUIndex =
	| MainHazards =		| MainHazards =
	| NFPA-H =		| NFPA-H =
	| NFPA-F =		| NFPA-F =
	| NFPA-R =		| NFPA-R =
	| NFPA-O =		| NFPA-S =
	| RPhrases =
	| SPhrases =
	| RSPhrases =
	| FlashPt =		| FlashPt =
	| Autoignition =		| AutoignitionPt =
	| ExploLimits =		| ExploLimits =
	| LD50 =		| LD50 =
	| PEL = }}		| PEL = }}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| OtherAnions =		| OtherAnions =
	| OtherCations =		| OtherCations =
	| OtherFunctn =		| OtherFunction =
	| Function =		| OtherFunction_label =
	| OtherCpds = }}		| OtherCompounds =
			}}
	}}		}}
			'''Sudan IV''' (C<sub>24</sub>H<sub>20</sub>N<sub>4</sub>O) is a ] (fat-soluble dye) ] used for the ] of ], ] and ] on frozen ] sections. It has the appearance of reddish brown crystals with melting point 199&nbsp;°C and maximum absorption at 520(357) nm.
			Sudan IV is one of the dyes used for ]ing. Similar dyes include ], ], and ]. Staining is an important biochemical technique, offering the ability to visually qualify the presence of the fatty compound of interest without isolating it. For staining purposes, Sudan IV can be made up in ].<ref>{{cite web|url=http://www.ihcworld.com/_protocols/special_stains/oil_red_o.htm|title=Oil Red O Staining Protocol|website=IHC World|accessdate=2021-03-17}}</ref> Alternatively, authors have reported using the dye saturated in ], 95% ], or 0.05% by weight in acetone:ethanol:water (50:35:15).{{Citation needed|date=August 2007}} The idea is to use a moderately apolar solvent to solubilize the dye allowing it to partition into the highly apolar fat without the solvent solubilizing the fat to be stained.
			], ], and Sudan IV have been classified as category 3 ] by the ].<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>
			In its purified form it is called '''Biebrich scarlet R''', which should not be confused with the water-soluble ].
			In industry, it is used to color nonpolar substances like ]s, ]s, ]es, ]s, various ] products, and ] ]s. Sudan IV is also used in ] as a ] to dye lower-taxed ]; because of that it is also known as '''Oil Tax Red'''. As a ], Sudan IV is considered an illegal dye, mainly because of its harmful effect over a long period of time, as it is a ]. It was ruled unsafe in the 1995 food safety regulations report.
			While the dye does stain triglycerides with an intense red color, it does not stain lipid droplets or phospholipids. Sudan IV can be used to stain the aorta by staining lipid-rich plaques. The dye can also be used to stain lipids in atherosclerotic lesions in mice.<ref>{{cite web |title=Sudan IV |url=https://www.sigmaaldrich.com/US/en/product/aldrich/198102 |website=MilliporeSigma |access-date=15 February 2023}}</ref>
			==References==
			{{reflist}}
			==External links==
			* entry
			{{Stains}}
			]
			]
			]
			]
			]
			]