Lamenallenic acid
Chemical compound
From Wikipedia, the free encyclopedia
Lamenallenic acid is a linear octadecatrienic fatty acid with the structural formula CH3CH=CH(CH2)8CH=C=CH(CH2)3COOH.[1] The delta notation is 18:3-delta-5,6allene,16t.[2] This is one of the rare allenic fatty acids found in nature, probably biosynthesized from laballenic acid.[3]
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| Other names
(E)-5,6,16-octadecatrienoic acid | |
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3D model (JSmol) |
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| Properties | |
| C18H30O2 | |
| Molar mass | 278.436 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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Physical properties
Some authors have attributed the cis-configuration to the double bond in the position 16=17.
The allene group is responsible for the marked optical activity of the acid. Lamenallenic acid is levorotatory with (R)-configuration.[4]
Discovery
The acid was initially isolated in 1967 by Mikolajczak, Rogers, Smith, and Wolff in the seed oil of Lamium purpureum (10-16%), a plant of the Lamiaceae family.[5][6] The compound is also found in the seed oil of other Lamiaceae: Lamium maculatum (~8%), Lamium album (~5%), Lamium amplexicaule (~5%).[7]
Synthesis
The acid can be obtained by a highly enantioselective synthesis, utilizing the recently developed EATA (enantioselective allenylation of terminal alkynes) reaction and aerobic oxidation reaction.[8]