{{Chembox <!-- Images --> | Name = Coniferonic acid | ImageFile = Coniferoric acid.svg | ImageSize = 250px | ImageAlt = <!-- Names --> | IUPACName = (5''Z'',9''Z'',12''Z'',15''Z'')-octadecatetraenoic acid | OtherNames = | Section1 = {{Chembox Identifiers | CASNo = | CASNo_Ref = {{Cascite|changed|CAS}} | ChemSpiderID = 34999888 | DTXSID = | EC_number = | ChEBI = 86135 | ChEMBL = | KEGG = | UNII = | PubChem = 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- | InChIKey = DNOBNGNBPVOMLW-XRPCLMINSA-N | SMILES = CCC=CCC=CCC=CCCC=CCCCC(=O)O }} | Section2 = {{Chembox Properties | H=28|O=2|C=18 | MolarMass = | Appearance = | Density = | MeltingPtC = | BoilingPtC = | BoilingPt_ref = | Solubility = }} | Section3 = {{Chembox Hazards | GHSPictograms = | GHSSignalWord = | GHS_ref = | HPhrases = | PPhrases = | MainHazards = | FlashPt = | AutoignitionPt = }} }} '''Coniferonic acid''' is a polyunsaturated 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.<ref>{{cite book |last1=Alasalvar |first1=Cesarettin |last2=Shahidi |first2=Fereidoon |title=Tree Nuts: Composition, Phytochemicals, and Health Effects |date=17 December 2008 |publisher=CRC Press |isbn=978-1-4200-1939-1 |page=287 |url=https://books.google.com/books?id=Uu4nzKx74noC&dq=Coniferonic+acid&pg=PA287 |access-date=2 June 2025 |language=en}}</ref><ref>{{cite book |last1=Hock |first1=Franz J. |last2=Pugsley |first2=Michael K. |title=Drug Discovery and Evaluation: Safety and Pharmacokinetic Assays |date=21 October 2024 |publisher=Springer Nature |isbn=978-3-031-35529-5 |page=1429 |url=https://books.google.com/books?id=0mUrEQAAQBAJ&dq=Coniferonic+acid&pg=PA1429 |access-date=2 June 2025 |language=en}}</ref>

==Discovery and natural occurrence== 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%).<ref>{{cite journal |last1=Mongrand |first1=Sébastien |last2=Badoc |first2=Alain |last3=Patouille |first3=Brigitte |last4=Lacomblez |first4=Chantal |last5=Chavent |first5=Marie |last6=Cassagne |first6=Claude |last7=Bessoule |first7=Jean-Jacques |title=Taxonomy of gymnospermae: multivariate analyses of leaf fatty acid composition |journal=Phytochemistry |date=1 September 2001 |volume=58 |issue=1 |pages=101–115 |doi=10.1016/S0031-9422(01)00139-X |pmid=11524119 |bibcode=2001PChem..58..101M |url=https://www.sciencedirect.com/science/article/abs/pii/S003194220100139X |access-date=2 June 2025 |issn=0031-9422|url-access=subscription }}</ref><ref>{{cite journal |last1=Jamieson |first1=G. R. |last2=Reid |first2=E. H. |title=The leaf lipids of some conifer species |journal=Phytochemistry |date=1 January 1972 |volume=11 |issue=1 |pages=269–275 |doi=10.1016/S0031-9422(00)90002-5 |bibcode=1972PChem..11..269J |url=https://www.sciencedirect.com/science/article/abs/pii/S0031942200900025 |access-date=2 June 2025 |issn=0031-9422|url-access=subscription }}</ref>

It is also found in the seed oil of Korean pine or ''Pinus koraiensis'' (≈14.6%) and ''Fokienia hodginsii'' (≈2.8%).<ref>{{cite journal |last1=Wolff |first1=Robert L. |last2=Pédrono |first2=Frédérique |last3=Pasquier |first3=Elodie |last4=Marpeau |first4=Anne M. |title=General characteristics of Pinus spp. Seed fatty acid compositions, and importance of Δ5-olefinic acids in the taxonomy and phylogeny of the genus |journal=Lipids |date=2000 |volume=35 |issue=1 |pages=1–22 |doi=10.1007/s11745-000-0489-y |pmid=10695919 |url=https://aocs.onlinelibrary.wiley.com/doi/10.1007/s11745-000-0489-y |access-date=2 June 2025 |language=en |issn=1558-9307|url-access=subscription }}</ref><ref>{{cite journal |last1=Wolff |first1=Robert L. |last2=Pédrono |first2=Frédérique |last3=Marpeau |first3=Anne M. |title=Fokienia hodginsii seed oil, another source of all-cis 5,9,12,15-18:4 (coniferonic) acid |journal=Journal of the American Oil Chemists' Society |date=1999 |volume=76 |issue=4 |pages=535–536 |doi=10.1007/s11746-999-0037-z |url=https://aocs.onlinelibrary.wiley.com/doi/10.1007/s11746-999-0037-z |access-date=2 June 2025 |language=en |issn=1558-9331|url-access=subscription }}</ref>

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.<ref>{{cite journal |last1=Pédrono |first1=Frédérique |last2=Boulier-Monthéan |first2=Nathalie |last3=Boissel |first3=Françoise |last4=Ossemond |first4=Jordane |last5=Viel |first5=Roselyne |last6=Fautrel |first6=Alain |last7=Marchix |first7=Justine |last8=Dupont |first8=Didier |title=Sciadonic acid derived from pine nuts as a food component to reduce plasma triglycerides by inhibiting the rat hepatic Δ9-desaturase |journal=Scientific Reports |date=10 April 2020 |volume=10 |issue=1 |pages=6223 |doi=10.1038/s41598-020-63301-3 |pmid=32277113 |bibcode=2020NatSR..10.6223P |url=https://www.nature.com/articles/s41598-020-63301-3 |access-date=19 May 2025 |language=en |issn=2045-2322|pmc=7148351 }}</ref>

==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.<ref>{{cite book |last1=Grossman |first1=Arthur |last2=Wollman |first2=Francis-André |title=The Chlamydomonas Sourcebook: Volume 2: Organellar and Metabolic Processes |date=15 February 2023 |publisher=Academic Press |isbn=978-0-323-91058-3 |page=56 |url=https://books.google.com/books?id=SNpVEAAAQBAJ&dq=Coniferonic+acid&pg=PA56 |access-date=2 June 2025 |language=en}}</ref>

== References == <references/>

Category:Alkenoic acids Category:Fatty acids