Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Nverify (what is YN ?)
Infobox references
Chemical compound
This article is about the unsaturated octadecanol, cis-9-octadecen-1-ol. For the saturated octadecanol, octadecan-1-ol, see Stearyl alcohol.
Oleyl alcohol/ˈoʊliˌɪl,ˈoʊliəl/,[1] or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural formula CH3(CH2)7−CH=CH−(CH2)8OH. It is a colorless oil, mainly used in cosmetics.[2]
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[3] and subsequently refined.[4][5]
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 mucus membranes; particularly the lungs.[6]
^"Oleyl" in the McGraw–Hill Dictionary of Scientific & Technical Terms (2003)
^Noweck, Klaus; Grafahrend, Wolfgang (2006). "Fatty Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_277.pub2. ISBN 978-3527306732.
^Bouveault, L.; Blanc, G. (1904). "Hydrogénation des éthers des acides possédant en outre les fonctions éther-oxyde ou acétal" [Hydrogenation of the ether of the acids furthermore possessing the ether-oxide or acetal functions]. Bull. Soc. Chim. Fr. (in French). 31 (3): 1210–1213.
^Reid, E. E.; Cockerille, F. O.; Meyer, J. D.; Cox, W. M.; Ruhoff, J. R. (1935). "Oleyl Alcohol". Organic Syntheses. 15: 51. doi:10.15227/orgsyn.015.0051; Collected Volumes, vol. 2, p. 468.
^Adkins, Homer; Gillespie, R. H. (1935). "Oleyl alcohol". Org. Synth. 29: 51. doi:10.15227/orgsyn.015.0051.
^Hussain, Alamdar; Arnold, John J.; Khan, Mansoor A.; Ahsan, Fakhrul (2004). "Absorption enhancers in pulmonary protein delivery". J. Control. Release. 94 (1): 15–24. doi:10.1016/j.jconrel.2003.10.001. PMID 14684268.
Oleylalcohol /ˈoʊliˌɪl, ˈoʊliəl/, or cis-9-octadecen-1-ol, is an unsaturated fatty alcohol with the molecular formula C18H36O or the condensed structural...
Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing...
with the source. Some commercially important fatty alcohols are lauryl, stearyl, and oleylalcohols. They are colourless oily liquids (for smaller carbon...
Vinyl alcohol, also called ethenol (IUPAC name; not ethanol) or ethylenol, is the simplest enol. With the formula CH2CHOH, it is a labile compound that...
ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula CH3CH2OH. It is an alcohol, with its...
Benzyl alcohol (also known as α-cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused...
Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable organic compound with a pungent alcoholic...
as drying in coatings. Reduction of the carboxylic acid group yields oleylalcohol. Ozonolysis of oleic acid is an important route to azelaic acid. The...
Amyl alcohols are alcohols with the formula C5H11OH. Eight are known. A mixture of amyl alcohols (also called amyl alcohol) can be obtained from fusel...
(also called methyl alcohol and wood spirit, amongst other names) is an organic chemical compound and the simplest aliphatic alcohol, with the chemical...
Cetyl alcohol /ˈsiːtəl/, also known as hexadecan-1-ol and palmityl alcohol, is a C-16 fatty alcohol with the formula CH3(CH2)15OH. At room temperature...
Stearyl alcohol, or 1-octadecanol, is an organic compound classified as a saturated fatty alcohol with the formula CH3(CH2)16CH2OH. It takes the form...
Isoamyl alcohol is a colorless liquid with the formula C 5H 12O, specifically (H3C–)2CH–CH2–CH2–OH. It is one of several isomers of amyl alcohol (pentanol)...
Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers)...
Phenethyl alcohol, or 2-phenylethanol, is an organic compound with the chemical formula C6H5CH2CH2OH. It is a colourless liquid with a pleasant floral...
Octanols are alcohols with the formula C8H17OH. A simple and important member is 1-Octanol, with an unbranched chain of carbons. Other commercially important...
A primary alcohol is an alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH”...
lauryl alcohol, is an organic compound produced industrially from palm kernel oil or coconut oil. It is a fatty alcohol. Sulfate esters of lauryl alcohol, especially...
freely soluble in water. It is classified as a polyalcohol and a sugar alcohol, specifically an alditol. The name derives from Ancient Greek: ξύλον, xyl[on]...
his new compound "glycol" because it shared qualities with both ethyl alcohol (with one hydroxyl group) and glycerin (with three hydroxyl groups). In...