Taxoleic acid

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Taxoleic acid
Names
IUPAC name
(5Z,9Z)-octadeca-5,9-dienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10,13-14H,2-8,11-12,15-17H2,1H3,(H,19,20)/b10-9-,14-13-
    Key: DFJAXEWDHVOILU-KWUOUXIESA-N
  • CCCCCCCC/C=C\CC/C=C\CCCC(=O)O
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.

Natural occurrence

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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]

Biosynthesis

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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]

References

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  1. ^ Leray, Claude (19 September 2012). Introduction to Lipidomics: From Bacteria to Man. CRC Press. p. 27. ISBN 978-1-4665-5147-3. Retrieved 18 May 2025.
  2. ^ Alasalvar, Cesarettin; Shahidi, Fereidoon (17 December 2008). Tree Nuts: Composition, Phytochemicals, and Health Effects. CRC Press. p. 287. ISBN 978-1-4200-1939-1. Retrieved 18 May 2025.
  3. ^ Bagci, Eyup (1 January 2007). "Fatty acids and tocochromanol patterns of some Turkish Apiaceae (Umbelliferae) plants; a chemotaxonomic approach". Acta Botanica Gallica. 154 (2): 143–151. Bibcode:2007AcBG..154..143B. doi:10.1080/12538078.2007.10516050. ISSN 1253-8078. Retrieved 18 May 2025.
  4. ^ Takagi, Toru; Itabashi, Yutaka (1982). "cis-5-olefinic unusual fatty acids in seed lipids of gymnospermae and their distribution in triacylglycerols". Lipids. 17 (10): 716–723. doi:10.1007/BF02534657. ISSN 1558-9307. Retrieved 18 May 2025.
  5. ^ Madrigal, R. V.; Smith Jr., C. R. (1975). "Taxus baccata seed oil: A new source ofcis-5,cis-9-octadecadienoic acid". Lipids. 10 (8): 502–504. doi:10.1007/BF02532438. ISSN 1558-9307. PMID 1160526. Retrieved 18 May 2025.
  6. ^ Wolff, R. L.; Deluc, Laurent G.; Marpeau, Anne M.; Comps, Bernard (1 December 1997). "Chemotaxonomic differentiation of conifer families and genera based on the seed oil fatty acid compositions: multivariate analyses". Trees. 12 (2): 57–65. Bibcode:1997Trees..12...57W. doi:10.1007/s004680050122. ISSN 1432-2285. Retrieved 18 May 2025.
  7. ^ Wolff, Robert L.; Deluc, Laurent G.; Marpeau, Anne M. (1996). "Conifer seeds: Oil content and fatty acid composition". Journal of the American Oil Chemists' Society. 73 (6): 765–771. doi:10.1007/BF02517953. ISSN 1558-9331. Retrieved 18 May 2025.
  8. ^ Pédrono, Frédérique; Boulier-Monthéan, Nathalie; Boissel, Françoise; Ossemond, Jordane; Viel, Roselyne; Fautrel, Alain; Marchix, Justine; Dupont, Didier (10 April 2020). "Sciadonic acid derived from pine nuts as a food component to reduce plasma triglycerides by inhibiting the rat hepatic Δ9-desaturase". Scientific Reports. 10 (1): 6223. doi:10.1038/s41598-020-63301-3. ISSN 2045-2322. PMC 7148351. Retrieved 19 May 2025.
  9. ^ Rahman, Atta-ur (23 June 2008). Studies in Natural Products Chemistry. Elsevier. p. 353. ISBN 978-0-08-056983-3. Retrieved 18 May 2025.
  10. ^ Hong, Haiping; Datla, Nagamani; Mackenzie, Samuel L.; Qiu, Xiao (2002). "Isolation and characterization of a Δ5 FA desaturase from Pythium irregulare by heterologous expression in Saccharomyces cerevisiae and oilseed crops". Lipids. 37 (9): 863–868. doi:10.1007/s11745-002-0972-5. ISSN 1558-9307. PMID 12458621. Retrieved 18 May 2025.
  11. ^ Carballeira, Néstor M.; Medina, Jesús R. (1 December 1994). "New Δ5,9 Fatty Acids in the Phospholipids of the Sea Anemone Stoichactis helianthus". Journal of Natural Products. 57 (12): 1688–1695. Bibcode:1994JNAtP..57.1688C. doi:10.1021/np50114a011. ISSN 0163-3864. PMID 7714536. Retrieved 18 May 2025.