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Revision as of 21:46, 11 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_C← Previous edit Latest revision as of 02:22, 17 September 2024 edit undoAzn bookworm10 (talk | contribs)Extended confirmed users1,274 editsm spelling 
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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 415881502
| Watchedfields = changed
| Reference = <ref></ref>
⚫ | verifiedrevid = 444338320
| ImageFile = Oleyl alcohol structure.png | ImageFile1 = Oleyl-alcohol-spacefilling.png
| ImageSize =
| ImageAlt1 = Space-filling model of oleyl alcohol
| ImageFile2 = Oleyl alcohol Structural Formula V1.svg
| ImageAlt2 = Structural model of oleyl alcohol
| IUPACName = (''Z'')-Octadec-9-en-1-ol | IUPACName = (''Z'')-Octadec-9-en-1-ol
| OtherNames = Octadecenol<br>''cis''-9-Octadecen-1-ol | OtherNames = ''cis''-9-Octadecen-1-ol
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4447562 | ChemSpiderID = 4447562
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
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| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D05245 | KEGG = D05245
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 73504
| InChI = 1/C18H36O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10,19H,2-8,11-18H2,1H3/b10-9- | InChI = 1/C18H36O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19/h9-10,19H,2-8,11-18H2,1H3/b10-9-
| InChIKey = ALSTYHKOOCGGFT-KTKRTIGZBF | InChIKey = ALSTYHKOOCGGFT-KTKRTIGZBF
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| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 143-28-2 | CASNo = 143-28-2
| PubChem = 5284499 | PubChem = 5284499
| SMILES = OCCCCCCCC\C=C/CCCCCCCC | SMILES = OCCCCCCCC\C=C/CCCCCCCC
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=18 | H=36 | O=1
| Formula = {{Carbon}}<sub>18</sub>{{Hydrogen}}<sub>36</sub>{{Oxygen}}
⚫ | Appearance =
| MolarMass = 268.478 g/mol
⚫ | Density = 0.845-0.855 g/cm<sup>3</sup>
⚫ | Appearance =
| MeltingPtC = 13 to 19
⚫ | Density = 0.845-0.855 g/cm<sup>3</sup>
| MeltingPt_notes =
| MeltingPt = 13-19 °C
| BoilingPt = 330-360 °C | BoilingPtC = 330 to 360
| BoilingPt_notes =
| Solubility = Insoluble | Solubility = Insoluble
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| NFPA-H = 1 | NFPA-H = 1
| NFPA-F = 0 | NFPA-F = 0
| NFPA-R = 0 | NFPA-R = 0
| NFPA-O = | NFPA-S =
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
}} }}
}} }}
{{about|the unsaturated octadecanol, cis-9-octadecen-1-ol|the saturated octadecanol, octadecan-1-ol|Stearyl alcohol}}

'''Oleyl alcohol''' {{IPAc-en|ˈ|oʊ|l|i|ˌ|ɪ|l|,_|ˈ|oʊ|l|i|əl}},<ref></ref> or '''''cis''-9-octadecen-1-ol''', is an ] ] with the ] {{chem2|auto=1|C18H36O}} or the ] {{chem2|1=CH3(CH2)7\sCH=CH\s(CH2)8OH}}. It is a colorless oil, mainly used in cosmetics.<ref name=Ullmann>{{Ullmann|first1=Klaus|last1=Noweck|first2=Wolfgang|last2=Grafahrend|title=Fatty Alcohols|year=2006|doi=10.1002/14356007.a10_277.pub2}}</ref>


It can be produced by the ] of ] esters by ], which avoids reduction of the C=C group (as would occur with usual catalytic hydrogenation). The required oleate esters are obtained from ] ], ], and, in particular, ] (from which it gains its name). The original procedure was reported by ] in 1904<ref>{{cite journal |author1=Bouveault, L. |authorlink1=Louis Bouveault |author2=Blanc, G. | journal = ] | year = 1904 | volume = 31 | issue = 3 | pages = 1210–1213 | title = Hydrogénation des éthers des acides possédant en outre les fonctions éther-oxyde ou acétal | language = French | url = http://gallica.bnf.fr/ark:/12148/bpt6k5469971k/f1214.image | trans-title = Hydrogenation of the ether of the acids furthermore possessing the ether-oxide or acetal functions}}</ref> and subsequently refined.<ref>{{OrgSynth|title = Oleyl Alcohol|first1 = E. E.|last1 = Reid|first2 = F. O.|last2 = Cockerille|first3 = J. D.|last3 = Meyer|first4 = W. M.|last4 = Cox|first5 = J. R.|last5 = Ruhoff|year = 1935|volume = 15|pages = 51|collvol = 2|collvolpages = 468|prep = cv2p0468|doi = 10.15227/orgsyn.015.0051}}</ref><ref>{{cite journal|journal=Org. Synth.|last1 = Adkins|first1 = Homer|authorlink1 = Homer Burton Adkins|last2 = Gillespie|first2 = R. H.|title = Oleyl alcohol|year = 1935|volume = 29|pages = 51|doi = 10.15227/orgsyn.015.0051}}</ref>
'''Oleyl alcohol''', '''octadecenol''', or '''cis-9-octadecen-1-ol''', is a ] coming from inedible ] ]. It is also found in ].
Its ] is {{Carbon}}<sub>18</sub>{{Hydrogen}}<sub>36</sub>{{Oxygen}} or CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>-CH=CH-(CH<sub>2</sub>)<sub>8</sub>OH.


It has uses as a nonionic ], ], ] and ] in ]s, ]s and many other ] products including ]s and ]s. It has also been investigated as a carrier for delivering medications through the skin or mucous membranes; particularly the lungs.<ref>{{cite journal|last1=Hussain|first1=Alamdar|last2=Arnold|first2=John J.|last3=Khan|first3=Mansoor A.|last4=Ahsan|first4=Fakhrul|title=Absorption enhancers in pulmonary protein delivery|journal=]|year=2004|volume=94|issue=1|pages=15–24|doi=10.1016/j.jconrel.2003.10.001|pmid=14684268}}</ref>
It is a non-]ic, ] ].


==See also==
It has uses as a nonionic ], ], ] and ] in ]s, ]s and many other ] products, ] for softening fabrics, surfactant and hair coating in ]s and ]s, and a carrier for medications.<ref>{{HPD|1701}}</ref>
* ] - the corresponding fatty acid
* ] - the corresponding amine
* ] - the corresponding amide


==References== ==References==
{{Reflist}} {{Reflist}}


{{alcohols}}
==External links==


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