Lamenallenic acid

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Lamenallenic acid
Names
Other names
(E)-5,6,16-octadecatrienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h2-3,12,14H,4-11,15-17H2,1H3,(H,19,20)/b3-2+
    Key: IHBRXZJPXHXMCN-NSCUHMNNSA-N
  • C/C=C/CCCCCCCCC=C=CCCCC(=O)O
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).

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]

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

Synthesis

References

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