Lesquerolic acid

Lesquerolic acid

Stereo, skeletal formula of lesquerolic acid (Z,R)
Names
IUPAC name (11Z, 14R)-14-Hydroxyicos-11-enoic acid
Identifiers
CAS Number	4103-20-2 Y
ChemSpider	4472235 Y
Jmol 3D model	Interactive image
MeSH	lesquerolic+acid
PubChem	5312810
InChI 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 Y Key: OONXYOAWMIVMCI-KWRJMZDGSA-N Y
SMILES O=C(O)CCCCCCCCC\C=C/C[C@H](O)CCCCCC
Properties
Chemical formula	C20H38O3
Molar mass	326.52 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 hydroxy acid that occurs naturally in Paysonia lasiocarpa and other Paysonia and Physaria species. It was first isolated in 1961 by a team from the Northern Regional Research Laboratory. 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. Lesquerolic acid, with other hydroxy fatty acids, has important industrial uses, including making resins, waxes, nylons and plastics.