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Names | |
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IUPAC name (5Z,9Z)-octadeca-5,9-dienoic acid | |
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3D model (JSmol) | |
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ChemSpider | |
PubChem CID | |
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Properties | |
C18H32O2 | |
Molar mass | 280.452 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Taxoleic acid is a diunsaturated fatty acid composed of 18 carbon atoms with double bonds in the positions 5=6 and 9=10, both in cis-configuration. [1] [2] Taxoleic acid is isomeric to linoleic acid.
The acid is present in the seed oils of conifers, such as Pinus nigra [3] (≈47%), Taxus cuspidata [4] (≈16.2%), Taxus baccata [5] (≈12.2%), Cedrus libani (≈9.4%), Abies pinsapo (≈8.2%), Pinus pinaster (≈7.1%), Abies alba (≈6.2%), among others. [6] [7]
It is found in conifers, along with other fatty acids (juniperonic, pinolenic, coniferonic, sciadonic acid) that have a double bond in the position 5, separated by more than one methylene group from the next double bond. [8]
Taxoleic acid is believed to be biosynthesized from oleic acid by the enzyme Δ5-desaturase. [9] A similar enzyme capable of producing taxolenic acid was also isolated from the oomycete Pythium irregulare . [10]
The biosynthesis of taxolenic acid and similar fatty acids has also been studied in sponges, where the double bonds are introduced sequentially in a random order. [11]