Chemistry:Taxoleic acid

From HandWiki
Taxoleic acid
Names
IUPAC name
(5Z,9Z)-octadeca-5,9-dienoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
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).
Infobox references
Tracking categories (test):

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

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

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

  1. ↑ Leray, Claude (19 September 2012) (in en). Introduction to Lipidomics: From Bacteria to Man. CRC Press. p. 27. ISBN 978-1-4665-5147-3. https://books.google.com/books?id=plXOBQAAQBAJ&dq=Taxoleic+acid&pg=PA27. Retrieved 18 May 2025. 
  2. ↑ Alasalvar, Cesarettin; Shahidi, Fereidoon (17 December 2008) (in en). Tree Nuts: Composition, Phytochemicals, and Health Effects. CRC Press. p. 287. ISBN 978-1-4200-1939-1. https://books.google.com/books?id=Uu4nzKx74noC&dq=Taxoleic+acid&pg=PA287. 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. doi:10.1080/12538078.2007.10516050. ISSN 1253-8078. Bibcode: 2007AcBG..154..143B. https://www.tandfonline.com/doi/abs/10.1080/12538078.2007.10516050. 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" (in en). Lipids 17 (10): 716–723. doi:10.1007/BF02534657. ISSN 1558-9307. https://aocs.onlinelibrary.wiley.com/doi/10.1007/BF02534657. 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" (in en). Lipids 10 (8): 502–504. doi:10.1007/BF02532438. ISSN 1558-9307. PMID 1160526. https://aocs.onlinelibrary.wiley.com/doi/10.1007/BF02532438. 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" (in en). Trees 12 (2): 57–65. doi:10.1007/s004680050122. ISSN 1432-2285. Bibcode: 1997Trees..12...57W. https://link.springer.com/article/10.1007/s004680050122. Retrieved 18 May 2025. 
  7. ↑ Wolff, Robert L.; Deluc, Laurent G.; Marpeau, Anne M. (1996). "Conifer seeds: Oil content and fatty acid composition" (in en). Journal of the American Oil Chemists' Society 73 (6): 765–771. doi:10.1007/BF02517953. ISSN 1558-9331. https://aocs.onlinelibrary.wiley.com/doi/10.1007/BF02517953. 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" (in en). Scientific Reports 10 (1): 6223. doi:10.1038/s41598-020-63301-3. ISSN 2045-2322. PMC 7148351. https://www.nature.com/articles/s41598-020-63301-3. Retrieved 19 May 2025. 
  9. ↑ Rahman, Atta-ur (23 June 2008) (in en). Studies in Natural Products Chemistry. Elsevier. p. 353. ISBN 978-0-08-056983-3. https://books.google.com/books?id=-M6NmLeGVD4C&dq=Taxoleic+acid&pg=PA353. 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" (in en). Lipids 37 (9): 863–868. doi:10.1007/s11745-002-0972-5. ISSN 1558-9307. PMID 12458621. https://aocs.onlinelibrary.wiley.com/doi/10.1007/s11745-002-0972-5. 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. doi:10.1021/np50114a011. ISSN 0163-3864. PMID 7714536. Bibcode: 1994JNAtP..57.1688C. https://pubs.acs.org/doi/abs/10.1021/np50114a011. Retrieved 18 May 2025. 



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