Juniperonic acid
Chemical compound
From Wikipedia, the free encyclopedia
Juniperonic acid is a polyunsaturated fatty acid featuring a 20-carbon chain with four cis-configured double bonds at positions 5, 11, 14, and 17. These structural traits categorize the compound as an omega-3 fatty acid, and it has drawn significant scientific attention due to its influence on regulating lipid membrane function and cell signaling processes.[1][2][3]
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| Names | |
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| IUPAC name
(5Z,11Z,14Z,17Z)-icosa-5,11,14,17-tetraenoic acid | |
| Identifiers | |
3D model (JSmol) |
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| Properties | |
| C20H32O2 | |
| Molar mass | 304.474 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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It is an isomer of eicosatetraenoic acid like the better known omega-6 fatty acid, arachidonic acid.[4]
History and natural occurrence
The acid was isolated for the first time in 1963 on the leaves and fruits of Ginkgo biloba by JL Gellerman and H. Schlenk.[5] It was then identified in the oils of other plants, especially conifers: Taxodium distichum (14.25%), Cupressus funebris (10.27%), Platycladus orientalis (9%), Taxus cuspidata (6.8%), etc.; in other flowering plants: Ephedra gerardiana (19.2%), Caltha sp. (9.4%), Ephedra nevadensis (9.3%), and Ephedra przewalskii (8.8%), among others; and in some marine animals.
The acid was later discovered in the seed oil of Juniperus communis (18%), which is why the acid is called juniperonic.[6] It was first synthesized in 2010 by A. Vik and co-workers.[7]
Oftentimes, it is found in conifers together with other fatty acids (taxoleic, pinolenic, taxoleic, sciadonic acid) that have a double bond in the position 5, separated by more than one methylene group from the next double bond.[8]
Uses
Thuja seeds are used in traditional Chinese medicine.[9] This acid exhibits interesting biological activity and becomes α-linolenic acid in animal models.