Ximenynic 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, a long-chain acetylenic fatty acid.

Discovery

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

Natural occurrence

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

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.

Species% of kernel oilNotes
S. spicatum34
S. obtusifolium71.5
S. acuminatum?

Patents

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 The patent application was deemed withdrawn in August 2012.

Uses

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

See also

References

  1. 1 2 3 4 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. 1 2 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. 1 2 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". Archived from the original on 2024-12-30. Retrieved 2016-02-03.
  6. ↑ Ximenynic acid
  7. ↑ "Sandalwood Nut CO2 Oil (product)". Archived from the original on 2016-03-06. Retrieved 2016-02-03.