Chemistry:Oleyl oleate

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Oleyl oleate
File:Oleyl oleate.svg
Names
IUPAC name
(9Z)-Octadec-9-enyl (9Z)-octadec-9-enoate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 222-980-0
KEGG
UNII
Properties
C36H68O2
Molar mass 532.938 g·mol−1
Appearance Yellow liquid[1]
Insoluble[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Tracking categories (test):

Oleyl oleate is a wax ester formed by the condensation of oleic acid and oleyl alcohol.

Properties

Oleyl oleate has the chemical formula C
36
H
68
O
2
and a molecular weight of 532.92 g/mol.[2] It is the ester derived from oleic acid and oleyl alcohol, both featuring a cis double bond at the 9-position. The systematic name is (9Z)-octadec-9-en-1-yl (9Z)-octadec-9-enoate.

Uses

Oleyl oleate is used as an emollient in cosmetics, providing skin conditioning and a non-greasy feel.[3] It is an ingredient in creams, lotions, and other personal care products. Oleyl oleate serves as a synthetic analogue of jojoba oil,[4] which consists primarily of similar long-chain wax esters, and has been explored for applications in lubricants and biofuels through biotechnological production in plant seeds.[5]

References

  1. 1.0 1.1 Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  2. CID 5364672 from PubChem
  3. "Oleyl oleate". SpecialChem. https://cosmetics.specialchem.com/inci-ingredients/oleyl-oleate. 
  4. Lopes, Danielle Branta; Duarte, Marta Cristina Teixeira; MacEdo, Gabriela Alves (2011). "Biosynthesis of oleyl oleate wax ester by non-commercial lipase". Food Science and Biotechnology 20 (5): 1203–1209. doi:10.1007/s10068-011-0166-7. 
  5. Yu, Dan; Hornung, Ellen; Iven, Tim; Feussner, Ivo (2018). "High-level accumulation of oleyl oleate in plant seed oil by abundant supply of oleic acid substrates to efficient wax ester synthesis enzymes". Biotechnology for Biofuels 11 (1). doi:10.1186/s13068-018-1057-4. PMID 29507605. Bibcode2018BB.....11...53Y.