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Laballenic acid
Chemical compound From Wikipedia, the free encyclopedia
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Laballenic acid is a linear fatty acid composed of 18 carbon atoms, with two consecutive double bonds (allene) in position 5=6=7. It has the structural formula CH3-(CH2)10-CH=C=CH-(CH2)3-COOH.
The acid is one of the rare allenic fatty acids found in nature.[1]
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Discovery
The acid was initially isolated in 1964 from the seed oil of Leonotis nepetifolia, a plant of the family Lamiaceae by M.O. Bagby, C.R. Smith Jr., and I.A. Wolff, and identified by the same authors a year later.[2][3]
Laballenic acid has also been found in Phlomoides tuberosa.
Synthesis
Several methods of synthesis have been published.[4] An efficient and enantioselective synthesis dates back to the year 2022. A further enantioselective synthesis is based on copper(II) bromide catalysis and the use of diphenylprolinol as a chiral auxiliary.[5]
It has also been reported that lamenallenic acid is probably biosynthesized from laballenic acid.[6]
Physical properties
Laballenic acid has axial chirality and is therefore optically active.[7][8] The absolute configuration of laballenic acid was determined by stereoselective synthesis.[9]
There exist two configurations: the (R)-form and the (S)-form of laballenic acid.[10] The naturally occurring acid has the R-configuration: it is an isomer of linoleic acid related with the similar phlomic acid.[11]
Use
Plant derivatives with high content of allenic fatty acids have shown cytotoxic, anti-inflammatory, and antiviral activity.[12][13]
References
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