Phlomic acid
From Wikipedia, the free encyclopedia
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| Names | |
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| Other names
Eicosa-7,8-dienoic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| Properties | |
| C20H36O2 | |
| Molar mass | 308.506 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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Phlomic acid is an unsaturated fatty acid with an allene group, which gives it axial chirality and makes it optically active. Phlomic is related to laballenic acid but has a shorter chain length.[1]
Phlomic acid is composed of 20 carbon atoms, with two consecutive double bonds (allene) in the position 7=8=9. The acid has the structural formula CH3-(CH2)10-CH=C=CH-(CH2)5-COOH. This is one of the rare allenic fatty acids found in nature, probably biosynthesized by elongation of laballenic acid.[2]
Phlomisic acid is found in some plant species of the Lamiaceae family. For example, it is present at 2.9% in the seed oil of Phlomoides tuberosa.[2] Other species of the genera Phlomis, such as deadnettle, hedgenettle, and Leonurus also contain the compound.[3] Out many species of the genus Leucas examined, 11 species contained small amounts of phlomisic acid. Only in two species was the content above 1%, and the highest measured content was 1.86%.[4]
Synthesis
Starting from hex-5-yn-1-ol, phlomic acid can be synthesized by a copper(II) bromide-catalyzed reaction with (S)-dimethylprolinol as a chiral auxiliary.[5]