Lesquerolic acid

Lesquerolic acid
Names
Preferred IUPAC name
(11Z,14R)-14-Hydroxyicos-11-enoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
MeSH lesquerolic+acid
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 Y
    Key: OONXYOAWMIVMCI-KWRJMZDGSA-N Y
  • 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).
Infobox references

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

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.

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