Coniferonic acid

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]

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

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%).^[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]