Pinolenic acid

Pinolenic acid

Names
Preferred IUPAC name (5Z,9Z,12Z)-Octadeca-5,9,12-trienoic acid
Other names Columbinic acid
Identifiers
CAS Number	16833-54-8  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:86136  N
ChemSpider	4471920  N
PubChem CID	5312493
UNII	B810C93MD7  Y
CompTox Dashboard (EPA)	DTXSID00895852
InChI InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,13-14H,2-5,8,11-12,15-17H2,1H3,(H,19,20)/b7-6-,10-9-,14-13- N Key: HXQHFNIKBKZGRP-URPRIDOGSA-N N InChI=1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10,13-14H,2-5,8,11-12,15-17H2,1H3,(H,19,20)/b7-6-,10-9-,14-13- Key: HXQHFNIKBKZGRP-URPRIDOGBF
SMILES CCCCC/C=C\C/C=C\CC/C=C\CCCC(=O)O
Properties
Chemical formula	C18H30O2
Molar mass	278.4296 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Pinolenic acid (often misspelled as pinoleic acid) is a fatty acid contained in Siberian Pine nuts, Korean Pine nuts and the seeds and xylem of other pine ( Pinus ) species. The highest percentage of pinolenic acid is found in Siberian pine nuts and the oil produced from them.^{[ citation needed ]}

Chemistry and biochemistry

Pinolenic acid is formally designated as all-cis-5,9,12-18:3. ^{[1] [2]} Some sources also use the term columbinic acid for this substance. ^[2] But columbinic acid sometimes designates an E-Z isomer (trans,cis,cisdelta-5,9,12/18:3) in the biologic literature. ^[3]

Pinolenic acid is an isomer of gamma-linolenic acid (GLA). GLA is an ω-6 essential fatty acid (EFA) but pinolenic acid is not. However, like the EFAs, it forms biologically active metabolites in the presence of cyclooxygenase or lipoxygenase. These metabolites can partially relieve some of the symptoms of EFA deficiency. ^[4]

Physiology

Recent research has shown its potential use in weight loss by curbing appetite. ^[5] Pinolenic acid causes the triggering of two hunger suppressants—cholecystokinin and glucagon-like peptide-1 (GLP-1). Pinolenic acid may have LDL-lowering properties by enhancing hepatic LDL uptake. ^[6]

Natural occurrence

Oftentimes, it is found in conifers together with other fatty acids (juniperonic, coniferonic, 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]

References

Pine nuts are a rich source of pinolenic acid

1. Cyberlipid Center. "POLYENOIC FATTY ACIDS". Archived from the original on 2018-09-30. Retrieved 2007-10-24.
2. PubChem. "PubChem - CID 5312493" . Retrieved 2007-10-25.
3. Tanaka T, Hattori T, Kouchi M, Hirano K, Satouchi K (1998). "Methylene-interrupted double bond in polyunsaturated fatty acid is an essential structure for metabolism by the fatty acid chain elongation system of rat liver". Biochim. Biophys. Acta. 1393 (2–3): 299–306. doi:10.1016/s0005-2760(98)00084-8. PMID   9748638.
4. Elliott WJ, Sprecher H, Needleman P (1985). "Physiologic effects of columbinic acid and its metabolites on rat skin". Biochim. Biophys. Acta. 835 (1): 158–60. doi:10.1016/0005-2760(85)90043-8. PMID   3924106.
5. "Korean pine nut may offer help for obesity" . Retrieved 2006-09-08.^{[ dead link ]}
6. Lee JW; Lee KW; Lee SW; Kim IH; Rhee C. (April 2004). "Selective increase in pinolenic acid (all-cis-5,9,12-18:3) in Korean pine nut oil by crystallization and its effect on LDL-receptor activity". Lipids. 39 (4): 383–7. doi:10.1007/s11745-004-1242-2. PMID   15357026. S2CID   4058921.
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. doi:10.1038/s41598-020-63301-3. ISSN   2045-2322. PMC   7148351 . Retrieved 19 May 2025.