Helenynolic acid
From Wikipedia, the free encyclopedia
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| Names | |
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| IUPAC name
(E,9S)-9-hydroxyoctadec-10-en-12-ynoic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
PubChem CID |
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| Properties | |
| C18H30O3 | |
| Molar mass | 294.435 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Helenynolic acid is a hydroxylated and conjugated unsaturated fatty acid containing both a double and a triple bond.[1][2] The acid belongs to the class of alkyne and alkenoic acids, as well as to the enynes. It is optically active with a negative rotation, i.e., levorotatory.
The delta notation is S-9-OH-18:2Δ10t,12a.
The acid was initially isolated in 1965 from the glycerides of the seed oil of Helichrysum bracteatum of the Asteraceae family, by R. G. Powell and others.[3]
Helenynolic acid occurs in enantiomerically pure form in Xerochrysum bracteatum.[4][5] In some seeds, heleninolic acid is formed by oxidation during storage, e.g., in those of Crepis vesicaria from the genus Crepis.[6]
The acid's presence has also been confirmed among the lipids of Helichrysum italicum.