Pinolenic acid
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| Names | |
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| Preferred IUPAC name
(5Z,9Z,12Z)-Octadeca-5,9,12-trienoic acid | |
| Other names
Columbinic acid
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| Identifiers | |
3D model (JSmol)
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PubChemCID
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CompTox Dashboard(EPA)
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| Properties | |
| C18H30O2 | |
| Molar mass | 278.4296 g/mol |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Pinolenic acid(often misspelled aspinoleic acid) is afatty acidcontained inSiberian Pinenuts,Korean Pinenuts and theseedsandxylemof other pine (Pinus) species. The highest percentage of pinolenic acid is found in Siberianpine nutsand theoilproduced from them.[citation needed]
Chemistry and biochemistry
[edit]Pinolenic acid is formally designated asall-cis-5,9,12-18:3.[1][2]Some sources also use the termcolumbinic acidfor this substance.[2]Butcolumbinic acidsometimes designates anE-Z isomer(trans,cis,cis delta-5,9,12/18:3) in the biologic literature.[3]
Pinolenic acid is anisomerofgamma-linolenic acid(GLA). GLA is an ω-6essential fatty acid(EFA) but pinolenic acid is not. However, like the EFAs, it forms biologically activemetabolitesin the presence ofcyclooxygenaseorlipoxygenase.These metabolites can partially relieve some of the symptoms of EFA deficiency.[4]
Physiology
[edit]Recent research has shown its potential use inweight lossby curbing appetite.[5] Pinolenic acid causes the triggering of two hunger suppressants—cholecystokininandglucagon-like peptide-1(GLP-1). Pinolenic acid may haveLDL-lowering properties by enhancing hepaticLDLuptake.[6]
References
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- ^ Cyberlipid Center."POLYENOIC FATTY ACIDS".Archived fromthe originalon 2018-09-30.Retrieved2007-10-24.
- ^abPubChem."PubChem - CID 5312493".Retrieved2007-10-25.
- ^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.PMID9748638.
- ^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.PMID3924106.
- ^"Korean pine nut may offer help for obesity".Retrieved2006-09-08.[dead link]
- ^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.PMID15357026.S2CID4058921.