Coniferonic acid

Coniferonic acid
Names
	IUPAC name (5Z,9Z,12Z,15Z)-octadecatetraenoic acid
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:86135;
ChemSpider	34999888;
PubChem CID	13751481;
	InChI InChI=1S/C18H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h3-4,6-7,9-10,13-14H,2,5,8,11-12,15-17H2,1H3,(H,19,20)/b4-3-,7-6-,10-9-,14-13- Key: DNOBNGNBPVOMLW-XRPCLMINSA-N;
	SMILES CCC=CCC=CCC=CCCC=CCCCC(=O)O;
Properties
Chemical formula	C18H28O2
Molar mass	276.420 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

Coniferonic acid is a saturated fatty acid composed of 18 carbon atoms with four double bonds, in positions 5=6, 9=10, 12=13, 15=16; all in cis-configuration.^[1]^[2]

Discovery and natural occurence

The acid has been isolated in the leaves of conifers, from which it took its common name. The species with the highest concentration are Larix decidua containing about 44% of the total fatty acids, Abies grandis (≈38%), Araucaria montana (≈8.9%), and Abies veitchii (≈7.8%).^[3]^[4]

It is also found in the seed oil of Korean pine or Pinus koraiensis (≈14.6%) and Fokienia hodginsii (≈2.8%).^[5]^[6]

Oftentimes, it is found in conifers together with other fatty acids (juniperonic, 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.^[7]

Biosynthesis

The acid is assumed to be biosynthesized from α-linolenic acid by the enzyme Δ5-desaturase. The ratio of the concentration of coniferonic acid to that of α-linolenic acid allows the taxonomic differentiation of some plant genera.^[8]

References

^ 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 2 June 2025.
^ Hock, Franz J.; Pugsley, Michael K. (21 October 2024). Drug Discovery and Evaluation: Safety and Pharmacokinetic Assays. Springer Nature. p. 1429. ISBN 978-3-031-35529-5. Retrieved 2 June 2025.
^ Mongrand, Sébastien; Badoc, Alain; Patouille, Brigitte; Lacomblez, Chantal; Chavent, Marie; Cassagne, Claude; Bessoule, Jean-Jacques (1 September 2001). "Taxonomy of gymnospermae: multivariate analyses of leaf fatty acid composition". Phytochemistry. 58 (1): 101–115. Bibcode:2001PChem..58..101M. doi:10.1016/S0031-9422(01)00139-X. ISSN 0031-9422. PMID 11524119. Retrieved 2 June 2025.
^ Jamieson, G. R.; Reid, E. H. (1 January 1972). "The leaf lipids of some conifer species". Phytochemistry. 11 (1): 269–275. Bibcode:1972PChem..11..269J. doi:10.1016/S0031-9422(00)90002-5. ISSN 0031-9422. Retrieved 2 June 2025.
^ Wolff, Robert L.; Pédrono, Frédérique; Pasquier, Elodie; Marpeau, Anne M. (2000). "General characteristics of Pinus spp. Seed fatty acid compositions, and importance of Δ5-olefinic acids in the taxonomy and phylogeny of the genus". Lipids. 35 (1): 1–22. doi:10.1007/s11745-000-0489-y. ISSN 1558-9307. PMID 10695919. Retrieved 2 June 2025.
^ Wolff, Robert L.; Pédrono, Frédérique; Marpeau, Anne M. (1999). "Fokienia hodginsii seed oil, another source of all-cis 5,9,12,15-18:4 (coniferonic) acid". Journal of the American Oil Chemists' Society. 76 (4): 535–536. doi:10.1007/s11746-999-0037-z. ISSN 1558-9331. Retrieved 2 June 2025.
^ 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. Bibcode:2020NatSR..10.6223P. doi:10.1038/s41598-020-63301-3. ISSN 2045-2322. PMID 32277113. Retrieved 19 May 2025.
^ Grossman, Arthur; Wollman, Francis-André (15 February 2023). The Chlamydomonas Sourcebook: Volume 2: Organellar and Metabolic Processes. Academic Press. p. 56. ISBN 978-0-323-91058-3. Retrieved 2 June 2025.

[1] 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 2 June 2025.

[2] Hock, Franz J.; Pugsley, Michael K. (21 October 2024). Drug Discovery and Evaluation: Safety and Pharmacokinetic Assays. Springer Nature. p. 1429. ISBN 978-3-031-35529-5. Retrieved 2 June 2025.

[3] Mongrand, Sébastien; Badoc, Alain; Patouille, Brigitte; Lacomblez, Chantal; Chavent, Marie; Cassagne, Claude; Bessoule, Jean-Jacques (1 September 2001). "Taxonomy of gymnospermae: multivariate analyses of leaf fatty acid composition". Phytochemistry. 58 (1): 101–115. Bibcode:2001PChem..58..101M. doi:10.1016/S0031-9422(01)00139-X. ISSN 0031-9422. PMID 11524119. Retrieved 2 June 2025.

[4] Jamieson, G. R.; Reid, E. H. (1 January 1972). "The leaf lipids of some conifer species". Phytochemistry. 11 (1): 269–275. Bibcode:1972PChem..11..269J. doi:10.1016/S0031-9422(00)90002-5. ISSN 0031-9422. Retrieved 2 June 2025.

[5] Wolff, Robert L.; Pédrono, Frédérique; Pasquier, Elodie; Marpeau, Anne M. (2000). "General characteristics of Pinus spp. Seed fatty acid compositions, and importance of Δ5-olefinic acids in the taxonomy and phylogeny of the genus". Lipids. 35 (1): 1–22. doi:10.1007/s11745-000-0489-y. ISSN 1558-9307. PMID 10695919. Retrieved 2 June 2025.

[6] Wolff, Robert L.; Pédrono, Frédérique; Marpeau, Anne M. (1999). "Fokienia hodginsii seed oil, another source of all-cis 5,9,12,15-18:4 (coniferonic) acid". Journal of the American Oil Chemists' Society. 76 (4): 535–536. doi:10.1007/s11746-999-0037-z. ISSN 1558-9331. Retrieved 2 June 2025.

[7] 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. Bibcode:2020NatSR..10.6223P. doi:10.1038/s41598-020-63301-3. ISSN 2045-2322. PMID 32277113. Retrieved 19 May 2025.

[8] Grossman, Arthur; Wollman, Francis-André (15 February 2023). The Chlamydomonas Sourcebook: Volume 2: Organellar and Metabolic Processes. Academic Press. p. 56. ISBN 978-0-323-91058-3. Retrieved 2 June 2025.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]