Lesquerolic acid
| Lesquerolic acid | |
|---|---|
 | |
| IUPAC name (11Z, 14R)-14-Hydroxyicos-11-enoic acid[1] | |
| Identifiers | |
| CAS number | 4103-20-2  |
| PubChem | 5312810 |
| ChemSpider | 4472235 |
| MeSH | lesquerolic+acid |
| Jmol-3D images | {{#if:O=C(O)CCCCCCCCC\C=C/C[C@H](O)CCCCCC|Image 1 |
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| Properties | |
| Molecular formula | C20H38O3 |
| Molar mass | 326.51 g mol−1 |
| Except where noted otherwise, 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.[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
- ↑ "CID 20980884 - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 5 December 2007. Retrieved 20 November 2011.
- ↑ C. R. Smith Jr., T. L. Wilson, T. K. Miwa, H. Zobel, R. L. Lohmar, I. A. Wolff (1961). J. Org. Chem. 26 (8): 2903–2905. doi:10.1021/jo01066a067.
- ↑ David A. Dierig (1995). "Lesquerella". New Crop FactSHEET.