Structure Database (LMSD)

Common Name
Pinolenic acid
Systematic Name
5Z,9Z,12Z-octadecatrienoic acid
Synonyms
  • C18:3n-6,9,13
LM ID
LMFA01030344
Formula
C18H30O2
Exact Mass
Calculate m/z
278.22458
Sum Composition
FA 18:3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
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View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Octadecanoids [FA02]

Biological Context

Pinolenic acid is a polyunsaturated fatty acid found in Korean pine (Pinus orientalis) and maritime pine (Pinus pinaster) seed oils. Both oils have been found to have lipid-lowering properties. A diet containing maritime pine seed oil (MPSO) lowered HDL and ApoA1 levels in transgenic mice expressing human ApoA1. MPSO was found to diminish cholesterol efflux in vitro.1 Korean pine seed oil supplements may help in obesity by reduction of appetite. People taking this oil had an increase in the satiety hormones CCK and GLP-1 and a reduced desire to eat.2 The activity of the oil is attributed to pinolenic acid. Pinolenic acid is not converted to arachidonic acid metabolically and can reduce arachidonic acid levels in the phosphatidylinositol fraction of HepG2 cells from 15.9% to 7.0%.3

This information has been provided by Cayman Chemical

References

1. Causey, J.L. Korean pine nut fatty acids induce satiety-producing hormone release in overweight human volunteers. The 231st ACS National Meeting,.
2. Asset, G., Leroy, A., Bauge, E., et al. Effects of dietary maritime pine (Pinus pinaster)-seed oil on high-density lipoprotein levels and in vitro cholesterol efflux in mice expressing human apolipoprotein A-I. Br. J. Nutr. 84(3), 353-360 (2000).
3. Tamotsu, T., Tatsunori, T., Morishige, J., et al. Non-methylene-interrupted polyunsaturated fatty acids: Effective substitute for arachidonate of phosphatidylinositol. Biochem. Biophys. Res. Commun. 264(3), 683-688 (1999).

Reactions

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ⓘ Reactions are shown if the E.C. number of the enzyme catalysing it is annotated in the UniProt database for a species belonging to the selected taxonomic class.
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Reactions graph legend

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Xeranthemum annuum (#145993)
Magnoliopsida (#3398)
cis-5,cis-9,cis-12-octadecatrienoic and some unusual oxygenated acids inXeranthemum annuum seed oil.,
Lipids, 1967
Pubmed ID: 17805745
Pinus (#3337)
Pinopsida (#58019)
5,9,12-Octadecatrienoic Acid in Finnish Pine Wood and Tall Oil

String Representations

InChiKey (Click to copy)
HXQHFNIKBKZGRP-URPRIDOGSA-N
InChi (Click to copy)
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-
SMILES (Click to copy)
C(CCC/C=C\CC/C=C\C/C=C\CCCCC)(=O)O

Other Databases

Wikipedia
Pinolenic_acid
LIPIDAT ID
5691
CHEBI ID
86136
PubChem CID
5312495
PlantFA ID
10100
Cayman ID
10008654

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 326.98
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.66
Molar Refractivity 86.90

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Created at
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Updated at
25th Apr 2022