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Revision as of 02:49, 11 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chemicals|error← Previous edit Latest revision as of 18:04, 17 August 2023 edit undo39.41.165.13 (talk) External links 
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{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 401252700
| Watchedfields = changed
|ImageFile=Oil_Red_O.svg
| verifiedrevid = 449660882
|ImageSize=250px
| ImageFile = Oil_Red_O.svg
|IUPACName=
| ImageSize = 250px
|OtherNames=
| ImageFile2 = Differentiated 3T3-L1 Cell line stained with Oil O Red.jpg
| ImageSize2 = 250px
| ImageCaption2 = Differentiated ] in a ] cell line stained with Oil Red O
| IUPACName = 1-(2,5-dimethyl-4-(2,5-dimethylphenyl) phenyldiazenyl) azonapthalen-2-ol
| OtherNames =
|Section1={{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14217961 | ChemSpiderID = 14217961
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 88213
| InChI = 1/C26H24N4O/c1-16-9-10-17(2)22(13-16)27-28-23-14-19(4)24(15-18(23)3)29-30-26-21-8-6-5-7-20(21)11-12-25(26)31/h5-15,31H,1-4H3/b28-27+,30-29+ | InChI = 1/C26H24N4O/c1-16-9-10-17(2)22(13-16)27-28-23-14-19(4)24(15-18(23)3)29-30-26-21-8-6-5-7-20(21)11-12-25(26)31/h5-15,31H,1-4H3/b28-27+,30-29+
| InChIKey = NPGIHFRTRXVWOY-XOXGWFOHBH | InChIKey = NPGIHFRTRXVWOY-XOXGWFOHBH
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = NPGIHFRTRXVWOY-XOXGWFOHSA-N | StdInChIKey = NPGIHFRTRXVWOY-XOXGWFOHSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=1320-06-5 | CASNo=1320-06-5
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem=5841742
| UNII = G7S71FND9B
| SMILES = Cc4cc(/N=N/c1cc(C)c(cc1C)/N=N/c2c3ccccc3ccc2O)c(C)cc4
| PubChem=5841742
| MeSHName=oil+red+O
| SMILES = Cc4cc(/N=N/c1cc(C)c(cc1C)/N=N/c2c3ccccc3ccc2O)c(C)cc4
| MeSHName=oil+red+O
}} }}
|Section2={{Chembox Properties |Section2={{Chembox Properties
| Formula=C<sub>26</sub>H<sub>24</sub>N<sub>4</sub>O | Formula=C<sub>26</sub>H<sub>24</sub>N<sub>4</sub>O
| MolarMass=408.49496 | MolarMass=408.49496
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3={{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}
'''Oil Red O''' ('''Solvent Red 27''', '''Sudan Red 5B''', '''C.I. 26125''', C<sub>26</sub>H<sub>24</sub>N<sub>4</sub>O) is a ] (fat-soluble dye) ] used for ] of neutral ] and ]s on frozen sections and some ] on paraffin sections. It has the appearance of a red powder with maximum absorption at 518(359) nm. '''Oil Red O''' ('''Solvent Red 27''', '''Sudan Red 5B''', '''C.I. 26125''', C<sub>26</sub>H<sub>24</sub>N<sub>4</sub>O) is a ] (fat-soluble dye) ] used for ] of neutral ] and ]s on frozen sections and some ] on paraffin sections. It has the appearance of a red powder with an ] maximum at 518 nanometers.<ref name="KrausEhebauer2016">{{cite journal|last1=Kraus|first1=Nils A.|last2=Ehebauer|first2=Franziska|last3=Zapp|first3=Benedikt|last4=Rudolphi|first4=Bianca|last5=Kraus|first5=Bettina J.|last6=Kraus|first6=Daniel|display-authors=3|title=Quantitative assessment of adipocyte differentiation in cell culture|journal=Adipocyte|volume=5|issue=4|year=2016|pages=351–358|issn=2162-3945|doi=10.1080/21623945.2016.1240137|pmid=27994948|pmc=5160397|doi-access=free}}</ref>


==Uses== ==Uses==
Oil Red O is one of the dyes used for ]ing. Similar dyes include ], ], and ]. The staining has to be performed on fresh samples, as alcohol fixation removes most lipids. Oil Red O largely replaced Sudan III and Sudan IV, as it provides much deeper red color and the stains are therefore much easier to see.
Oil Red O is one of the dyes used for ]ing.
Similar dyes include ], ], and ]. The staining has to be performed on fresh samples, as alcohol fixation removes the lipids.


Oil Red O can be used to mark lipid-containing vacuoles, particularly in cases of ] or ]. It can also be used to stain liver sections for histological analysis, quantify cell lipid content, and to stain the aorta to examine lesions from atherosclerosis.<ref>{{cite web |title=Oil Red O |url=https://www.sigmaaldrich.com/US/en/product/sial/o0625 |website=MilliporeSigma |access-date=15 February 2023}}</ref>
Oil Red O largely replaced Sudan III and Sudan IV, as it provides much deeper red color and the stains are therefore much easier to see.


In ], Oil Red O is used in some compositions of red ]s. It is also used to dye some ]s, e.g. ] ]s. In ], Oil Red O is used in some compositions of red ]s.


==Forensic== ==Forensic==
When staining, Oil Red O can make fat more visible in various cuts in pathology.<ref name="urlForensic Pathology">{{cite web |url=http://library.med.utah.edu/WebPath/FORHTML/FOR002.html |title=Forensic Pathology }}</ref>

When staining, Oil Red O can make fat more visible in various cuts in pathology.<ref name="urlForensic Pathology">{{cite web |url=http://library.med.utah.edu/WebPath/FORHTML/FOR002.html |title=Forensic Pathology |work= |accessdate=}}</ref>


It is also used in a technique (the method is called as the dye: Oil Red O), discovered in 2004 by ], for staining latent ]s.<ref>Triplett M, ''Fingerprint Dictionary'', Two Rings Publishing, Bellevue, Washington.</ref> This technique allows the development of latent fingerprints on porous exhibits (such as paper, cardboard, etc.) that are dry or wet. It is also used in a technique (the method is called as the dye: Oil Red O), discovered in 2004 by ], for staining latent ]s.<ref>Triplett M, ''Fingerprint Dictionary'', Two Rings Publishing, Bellevue, Washington.</ref> This technique allows the development of latent fingerprints on porous exhibits (such as paper, cardboard, etc.) that are dry or wet.


It mainly targets fat deposits on the surface of porous exhibits.<ref>Beaudoin, A. New technique for revealing latent fingerprints on wet, porous surfaces: Oil Red O. Journal of Forensic Identification, 2004, 54 (4), 413-421.</ref> It is a non-destructive technique (which does not destroy the exhibit and doesn’t prevent the use of other techniques). It mainly targets fat deposits on the surface of porous exhibits.<ref>Beaudoin, A. New technique for revealing latent fingerprints on wet, porous surfaces: Oil Red O. Journal of Forensic Identification, 2004, 54 (4), 413-421.</ref> It is a non-destructive technique (which does not destroy the exhibit nor prevents the use of other techniques).


It is a safe alternative to the Physical Developer method,<ref>Rawji, A. ; Beaudoin, A. Oil Red O versus Physical Developer on wet papers: a comparitive study. Journal of Forensic Identification, 2006, 56 (1), 33-54.</ref> and is also used in sequence with other methods of fingerprints development.<ref>Guigui, K.; Beaudoin, A. The use of Oil Red O in sequence with other methods of fingerprint development. Journal of Forensic Identification, 2007, 57 (4), 550-581.</ref> It is a safe alternative to the Physical Developer method,<ref>Rawji, A. ; Beaudoin, A. Oil Red O versus Physical Developer on wet papers: a comparative study. Journal of Forensic Identification, 2006, 56 (1), 33-54.</ref> and is also used in sequence with other methods of fingerprints development.<ref>Guigui, K.; Beaudoin, A. The use of Oil Red O in sequence with other methods of fingerprint development. Journal of Forensic Identification, 2007, 57 (4), 550-581.</ref>


==References== ==References==
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==External links== ==External links==
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