Chemistry:Lesquerolic acid

From HandWiki
Lesquerolic acid
Stereo, skeletal formula of lesquerolic acid (Z,R)
Names
Preferred IUPAC name
(11Z,14R)-14-Hydroxyicos-11-enoic acid[1]
Identifiers
3D model (JSmol)
ChemSpider
MeSH lesquerolic+acid
UNII
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).
Infobox references

Lesquerolic acid is a hydroxycarboxylic acid that occurs naturally in Paysonia lasiocarpa and other Paysonia and Physaria species.[2] 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.[3] 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. https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=20980884. 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. David A. Dierig (1995). "Lesquerella". New Crop FactSHEET. http://www.hort.purdue.edu/newcrop/cropfactsheets/Lesquerella.html.