oleyl alcohol

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444338320

| ImageFile1 = Oleyl-alcohol-spacefilling.png

| 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

| OtherNames = cis-9-Octadecen-1-ol

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 4447562

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 172F2WN8DV

| KEGG_Ref = {{keggcite|correct|kegg}}

| 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-

| InChIKey = ALSTYHKOOCGGFT-KTKRTIGZBF

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/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-

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ALSTYHKOOCGGFT-KTKRTIGZSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 143-28-2

| PubChem = 5284499

| SMILES = OCCCCCCCC\C=C/CCCCCCCC

}}

|Section2={{Chembox Properties

| C=18 | H=36 | O=1

| Appearance =

| Density = 0.845-0.855 g/cm³

| MeltingPtC = 13 to 19

| MeltingPt_notes =

| BoilingPtC = 330 to 360

| BoilingPt_notes =

| Solubility = Insoluble

}}

|Section3={{Chembox Hazards

| NFPA-H = 1

| NFPA-F = 0

| NFPA-R = 0

| NFPA-S =

| MainHazards =

| FlashPt =

| 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}},[http://encyclopedia2.thefreedictionary.com/oleyl+alcohol "Oleyl" in the McGraw–Hill Dictionary of Scientific & Technical Terms (2003)] or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula {{chem2|auto=1|C18H36O}} or the condensed structural formula {{chem2|1=CH3(CH2)7\sCH=CH\s(CH2)8OH}}. It is a colorless oil, mainly used in cosmetics.{{Ullmann|first1=Klaus|last1=Noweck|first2=Wolfgang|last2=Grafahrend|title=Fatty Alcohols|year=2006|doi=10.1002/14356007.a10_277.pub2}}

It can be produced by the hydrogenation of oleic acid esters by Bouveault–Blanc reduction, which avoids reduction of the C=C group (as would occur with usual catalytic hydrogenation). The required oleate esters are obtained from beef fat, fish oil, and, in particular, olive oil (from which it gains its name). The original procedure was reported by Louis Bouveault in 1904{{cite journal |author1=Bouveault, L. |authorlink1=Louis Bouveault |author2=Blanc, G. | journal = Bull. Soc. Chim. Fr. | 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}} and subsequently refined.{{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}}{{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}}

It has uses as a nonionic surfactant, emulsifier, emollient and thickener in skin creams, lotions and many other cosmetic products including shampoos and hair conditioners. It has also been investigated as a carrier for delivering medications through the skin or mucous membranes; particularly the lungs.{{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=J. Control. Release|year=2004|volume=94|issue=1|pages=15–24|doi=10.1016/j.jconrel.2003.10.001|pmid=14684268}}