Lesquerolic acid

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Lesquerolic acid
Stereo, skeletal formula of lesquerolic acid (Z,R) Lesquerolic acid.png
Stereo, skeletal formula of lesquerolic acid (Z,R)
Names
Preferred IUPAC name
(11Z,14R)-14-Hydroxyicos-11-enoic acid [1]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH lesquerolic+acid
PubChem CID
UNII
  • InChI=1S/C20H38O3/c1-2-3-4-13-16-19(21)17-14-11-9-7-5-6-8-10-12-15-18-20(22)23/h11,14,19,21H,2-10,12-13,15-18H2,1H3,(H,22,23)/b14-11-/t19-/m1/s1 Yes check.svgY
    Key: OONXYOAWMIVMCI-KWRJMZDGSA-N Yes check.svgY
  • O=C(O)CCCCCCCCC\C=C/C[C@H](O)CCCCCC
Properties
C20H38O3
Molar mass 326.521 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lesquerolic acid is a hydroxycarboxylic acid that occurs naturally in Paysonia lasiocarpa and other Paysonia and Physaria species. [2] The acid is typically found together with other hydroxylated fatty acids, such as densipolic, auricolic, ricinoleic, etc. [3]

This compound has the R configuration at the alcohol-bearing stereocenter, and it is of the Z configuration at the olefin. Lesquerolic acid is chemically similar to ricinoleic acid, but with two additional carbons at the carboxyl end of the carbon chain. [4]

Uses

Lesquerolic acid, with other hydroxy fatty acids, has important industrial uses, including making resins, waxes, nylons and plastics.

References

  1. ↑ "CID 20980884 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 5 December 2007. Retrieved 20 November 2011.
  2. ↑ C. R. Smith Jr.; T. L. Wilson; T. K. Miwa; H. Zobel; R. L. Lohmar; I. A. Wolff (1961). "Lesquerolic Acid. A New Hydroxy Acid from Lesquerella Seed Oil1a". J. Org. Chem. 26 (8): 2903–2905. doi:10.1021/jo01066a067.
  3. ↑ Salywon, Andrew M.; Dierig, David A.; Rebman, Jon P.; de Rodríguez, Diana Jasso (2005). "Evaluation of new Lesquerella and Physaria (Brassicaceae) oilseed germplasm" . American Journal of Botany . 92 (1): 53–62. doi:10.3732/ajb.92.1.53. ISSN   1537-2197 . Retrieved 4 April 2025.
  4. ↑ David A. Dierig (1995). "Lesquerella". New Crop FactSHEET.


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