Ximenynic acid

Not to be confused with ximenic acid, a 26 carbon omega-9 fatty acid.
Ximenynic acid
Names
Preferred IUPAC name
(11E)-Octadec-11-en-9-ynoic acid
Other names
Santalbic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.346 Edit this at Wikidata
EC Number
  • 209-179-1
UNII
  • InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-8H,2-6,11-17H2,1H3,(H,19,20)/b8-7+
    Key: VENIIVIRETXKSV-BQYQJAHWSA-N
  • CCCCCCC=CC#CCCCCCCCC(=O)O
Properties
C18H30O2
Molar mass 278.436 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Ximenynic acid is trans-11-octadecen-9-ynoic acid,[1] a long-chain acetylenic fatty acid.[1]

It was discovered in the fruit kernels of three species of South American plants in the genus Ximenia, after which it is named.[2] and found to have the formula C18H30O2.[2]

It can be extracted from the fruit kernels of the Santalum obtusifolium (Sandalwood)[3] and the Australian sandalwood Santalum spicatum[1]

It is also found in seed oil of other plants in the Santalaceae family, including the native cherry Exocarpos cupressiformis and sweet quandong Santalum acuminatum.[4]

Sources

Species % of kernel oil Notes
S. spicatum 34 [1]
S. obtusifolium 71.5 [3]
S. acuminatum ?

Patents

It was the subject of a 2003 European patent (for use in food).[5] The patent application was deemed withdrawn in August 2012.[6]

Uses

It is used in some skincare products.[7][better source needed]

References

  1. ^ a b c d Liu, Yandi D.; Longmore, Robert B.; Fox, John E. D. (December 1996). "Separation and identification of ximenynic acid isomers in the seed oil of Santalum spicatum R.Br. as their 4,4-dimethyloxazoline derivatives". Journal of the American Oil Chemists' Society. 73 (12): 1729–1731. doi:10.1007/BF02517979. ISSN 0003-021X. S2CID 83483921.
  2. ^ a b Lightelm, S. P.; Schwartz, H. M.; von Holdt, M. M. (1952). "193. The chemistry of ximenynic acid". Journal of the Chemical Society (Resumed): 1088–1093. doi:10.1039/jr9520001088. ISSN 0368-1769.
  3. ^ a b Medicinal Plants in Australia, Volume 1. Cheryll Williams page 274. ISBN 978-1-877058-79-0
  4. ^ Okada, Shoko; Zhou, Xue-Rong; Damcevski, Katherine; Gibb, Nerida; Wood, Craig; Hamberg, Mats; Haritos, Victoria S. (November 2013). "Diversity of Δ12 Fatty Acid Desaturases in Santalaceae and Their Role in Production of Seed Oil Acetylenic Fatty Acids". Journal of Biological Chemistry. 288 (45): 32405–32413. doi:10.1074/jbc.M113.511931. PMC 3820875. PMID 24062307.
  5. ^ EP 1402787 A1:Ximenynic acid
  6. ^ Ximenynic acid
  7. ^ Sandalwood Nut CO2 Oil (product)