Juniperonic acid

Juniperonic acid is a polyunsaturated fatty acid featuring a 20-carbon chain with four cis-configured double bonds at positions 5, 11, 14, and 17. These structural traits categorize the compound as an omega-3 fatty acid, and it has drawn significant scientific attention due to its influence on regulating lipid membrane function and cell signaling processes.^[1][2][3]

Juniperonic acid

Names
IUPAC name (5Z,11Z,14Z,17Z)-icosa-5,11,14,17-tetraenoic acid
Identifiers
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82835
ChemSpider	4471968
PubChem CID	5312543
InChI InChI=1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,15-16H,2,5,8,11-14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,16-15- Key: JDKIKEYFSJUYJZ-OUJQXAOTSA-N
SMILES CC/C=C\C/C=C\C/C=C\CCCC/C=C\CCCC(=O)O
Properties
Chemical formula	C20H32O2
Molar mass	304.474 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

It is an isomer of eicosatetraenoic acid like the better known omega-6 fatty acid, arachidonic acid.^[4]

History and natural occurrence

The acid was isolated for the first time in 1963 on the leaves and fruits of Ginkgo biloba by JL Gellerman and H. Schlenk.^[5] It was then identified in the oils of other plants, especially conifers: Taxodium distichum (14.25%), Cupressus funebris (10.27%), Platycladus orientalis (9%), Taxus cuspidata (6.8%), etc.; in other flowering plants: Ephedra gerardianaii (19.2%), Caltha sp. (9.4%), Ephedra nevadensis (9.3%), and Ephedra przewalskii (8.8%), among others; and in some marine animals.

The acid was later discovered in the seed oil of Juniperus communis (18%), which is why the acid is called juniperonic.^[6] It was first synthesized in 2010 by A. Vik and co-workers.^[7]

Oftentimes, it is found in conifers together with other fatty acids (taxoleic, 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.^[8]

Uses

Thuja seeds are used in traditional Chinese medicine.^[9] This acid exhibits interesting biological activity and becomes α-linolenic acid in animal models.