Oleyl alcohol

Oleyl alcohol
Names
IUPAC name
(Z)-Octadec-9-en-1-ol
Other names
Octadecenol
cis-9-Octadecen-1-ol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.005.089
KEGG
UNII
Properties
C18H36O
Molar mass 268.478 g/mol
Density 0.845-0.855 g/cm3
Melting point 13 to 19 °C (55 to 66 °F; 286 to 292 K)
Boiling point 330 to 360 °C (626 to 680 °F; 603 to 633 K)
Insoluble
Hazards
NFPA 704
Flammability code 0: Will not burn. E.g., waterHealth code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentineReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Oleyl alcohol /ˈoʊliˌɪl, ˈoʊliəl/,[1][2] octadecenol /ˌɒktəˈdɛsɪˌnɒl/, 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 can be produced by the hydrogenation of oleic acid esters;[3] which can be obtained naturally from beef fat, fish oil and in particular olive oil (from which it gains its name). Production by the Bouveault–Blanc reduction of ethyl oleate or n-butyl oleate esters was reported by Louis Bouveault in 1904[4] and subsequently refined.[5][6]

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.[7]

See also

References

  1. ↑ "Oleyl" at Dictionary.com
  2. ↑ "Oleyl" in the McGraw–Hill Dictionary of Scientific & Technical Terms (2003)
  3. ↑ Kreutzer, Udo R. (1984). "Manufacture of fatty alcohols based on natural fats and oils". J. Am. Oil Chem. Soc. 61 (2): 343–348. doi:10.1007/BF02678792.
  4. ↑ 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.
  5. ↑ 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. ; Collective Volume, 2, p. 468
  6. ↑ Adkins, Homer; Gillespie, R. H. (1949). "Oleyl alcohol". Organic Syntheses. 29: 80. doi:10.15227/orgsyn.029.0080. ; Collective Volume, 3, p. 671
  7. ↑ 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.
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