Pinolenic acid
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 427061286
| ImageFile = Pinolenic acid (By JW).svg
| Name = Pinolenic acid
| PIN = (5Z,9Z,12Z)-Octadeca-5,9,12-trienoic acid
| OtherNames=Columbinic acid
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 16833-54-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = B810C93MD7
| PubChem= 5312493
| SMILES = CCCCC/C=C\C/C=C\CC/C=C\CCCC(=O)O
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4471920
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 86136
| 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-
| InChIKey = HXQHFNIKBKZGRP-URPRIDOGBF
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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-
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = HXQHFNIKBKZGRP-URPRIDOGSA-N
}}
| Section2 = {{Chembox Properties
| Formula = C18H30O2
| MolarMass = 278.4296 g/mol
| Density =
| MeltingPt =
| BoilingPt =
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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|date=March 2019}}
Chemistry and biochemistry
Pinolenic acid is formally designated as all-cis-5,9,12-18:3.
{{cite web
| title=POLYENOIC FATTY ACIDS
| url=http://www.cyberlipid.org/fa/acid0003.htm#1e
| author=Cyberlipid Center
| accessdate=2007-10-24
| archive-url=https://web.archive.org/web/20180930034042/http://www.cyberlipid.org/fa/acid0003.htm#1e
| archive-date=2018-09-30
| url-status=dead
}}
|url=https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5312493
|title= PubChem - CID 5312493
|accessdate=2007-10-25
|author=PubChem}} Some sources also use the term columbinic acid for this substance. But columbinic acid sometimes designates an E-Z isomer (trans,cis,cis
delta-5,9,12/18:3) in the biologic literature.{{cite journal |vauthors=Tanaka T, Hattori T, Kouchi M, Hirano K, Satouchi K |title=Methylene-interrupted double bond in polyunsaturated fatty acid is an essential structure for metabolism by the fatty acid chain elongation system of rat liver |journal=Biochim. Biophys. Acta |volume=1393 |issue=2–3 |pages=299–306 |year=1998 |pmid=9748638 |doi=10.1016/s0005-2760(98)00084-8}}
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.{{cite journal |vauthors=Elliott WJ, Sprecher H, Needleman P |title=Physiologic effects of columbinic acid and its metabolites on rat skin |journal=Biochim. Biophys. Acta |volume=835 |issue=1 |pages=158–60 |year=1985 |pmid=3924106 |doi=10.1016/0005-2760(85)90043-8}}
Physiology
Recent research has shown its potential use in weight loss by curbing appetite.{{cite web| url= https://news.yahoo.com/s/nm/20060908/hl_nm/indonesia_pinenut_dc
|title= Korean pine nut may offer help for obesity
|accessdate= 2006-09-08}} {{Dead link|date=October 2010|bot=H3llBot}}
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.{{cite journal
|journal= Lipids|date=April 2004|volume=39|issue=4|pages=383–7
|title= 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
|author1=Lee JW |author2=Lee KW |author3=Lee SW |author4=Kim IH |author5=Rhee C. |doi= 10.1007/s11745-004-1242-2
|pmid= 15357026|s2cid=4058921}}
