pinolenic acid
trans-5,9,12-octadecatrienoic acid
Identification
| Name | pinolenic acid |
| IUPAC | (5E,9E,12E)-octadeca-5,9,12-trienoic acid |
| CAS Number | 13237-97-3 |
| FDA UNII | Search |
| Molecular Formula | C18 H30 O2 |
| Molecular Weight | 278.43550000 |
| Nikkaji Number | J412.578I |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 384.00 to 385.00 °C. @ 760.00 mm Hg (est) |
| Flash Point | 539.00 °F. TCC ( 281.70 °C. ) (est) |
| logP (o/w) | 6.395 (est) |
| Soluble in | water, 0.02371 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for pinolenic acid usage levels up to | not for fragrance use. |
| Recommendation for pinolenic acid flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
columbinic acid
(5E,9E,12E)-
octadeca-5,9,12-trienoic acid
(E)-5,9,12-
octadecatrienoic acid
trans-5,9,12-
octadecatrienoic acid
PubMed:
Metabolic Conversion of C20 Polymethylene-Interrupted Polyunsaturated Fatty Acids to Essential Fatty Acids.
PubMed:
PGE2 production is suppressed by chemically-synthesized Î7-eicosatrienoic acid in macrophages through the competitive inhibition of COX-2.
PubMed:
Synthesis of phytosteryl ester containing pinolenic acid in a solvent-free system using immobilized Candida rugosa lipase.
PubMed:
Diet enriched with korean pine nut oil improves mitochondrial oxidative metabolism in skeletal muscle and brown adipose tissue in diet-induced obesity.
PubMed:
Synthesis of monoacylglycerol containing pinolenic acid via stepwise esterification using a cold active lipase.
PubMed:
Lipase-catalyzed production of pinolenic acid concentrate from pine nut oil using a recirculating packed bed reactor.
PubMed:
[Pine mouth syndrome: a global problem].
PubMed:
Effects of heat and ultraviolet radiation on the oxidative stability of pine nut oil supplemented with carnosic acid.
PubMed:
Lipase-catalysed production of triacylglycerols enriched in pinolenic acid at the sn-2 position from pine nut oil.
PubMed:
Effects of postharvest treatments on fruit quality of sweet pepper at low temperature.
PubMed:
Enrichment of pinolenic acid at the sn-2 position of triacylglycerol molecules through lipase-catalyzed reaction.
PubMed:
Metabolic diversity in biohydrogenation of polyunsaturated fatty acids by lactic acid bacteria involving conjugated fatty acid production.
PubMed:
Uptake and incorporation of pinolenic acid reduces n-6 polyunsaturated fatty acid and downstream prostaglandin formation in murine macrophage.
PubMed:
A front-end desaturase from Chlamydomonas reinhardtii produces pinolenic and coniferonic acids by omega13 desaturation in methylotrophic yeast and tobacco.
PubMed:
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.
PubMed:
Abietoid seed fatty acid compositions--a review of the genera Abies, Cedrus, Hesperopeuce, Keteleeria, Pseudolarix, and Tsuga and preliminary inferences on the taxonomy of Pinaceae.
PubMed:
An unusual desaturase in Aquilegia vulgaris.
PubMed:
General characteristics of Pinus spp. seed fatty acid compositions, and importance of delta5-olefinic acids in the taxonomy and phylogeny of the genus.
PubMed:
Non-methylene-interrupted polyunsaturated fatty acids: effective substitute for arachidonate of phosphatidylinositol.
PubMed:
Identification of Delta5-desaturase from Mortierella alpina by heterologous expression in Bakers' yeast and canola.
PubMed:
Methylene-interrupted double bond in polyunsaturated fatty acid is an essential structure for metabolism by the fatty acid chain elongation system of rat liver.
PubMed:
Effects of gamma-linolenic acid and its positional isomer pinolenic acid on immune parameters of brown-Norway rats.
PubMed:
Octadecatrienoic acids as the substrates for the key enzymes in glycerolipid biosynthesis and fatty acid oxidation in rat liver.
PubMed:
Influence of Korean pine (Pinus koraiensis)-seed oil containing cis-5,cis-9,cis-12-octadecatrienoic acid on polyunsaturated fatty acid metabolism, eicosanoid production and blood pressure of rats.
PubMed:
Barrier function regulates epidermal lipid and DNA synthesis.
PubMed:
Antagonists and inhibitors of lipid mediators in experimental inflammation of the cornea.
PubMed:
Epidermal HMG CoA reductase activity in essential fatty acid deficiency: barrier requirements rather than eicosanoid generation regulate cholesterol synthesis.
PubMed:
[Regulation of the epidermal permeability barrier by lipids and hyperproliferation].
PubMed:
Modulation of immunogenic keratitis in rabbits by topical administration of poly-unsaturated fatty acids.
PubMed:
Metabolism of 6,9,12-octadecatrienoic acid and 6,9,12,15-octadecatetraenoic acid by rat hepatocytes.
PubMed:
Naturally occurring conjugated octadecatrienoic acids are strong inhibitors of prostaglandin biosynthesis.
PubMed:
Effect of dietary columbinic acid on the fatty acid composition and physical membrane properties of different tissues of EFA-deficient rats.
PubMed:
Essential fatty acid deficiency: a new look at an old problem.
PubMed:
Effect of different acids with delta 9,12-dienoic structures on delta 9 desaturation activity in rat liver microsomes.
PubMed:
Regulation of linoleic acid delta 6-desaturation by a cytosolic lipoprotein-like fraction in isolated rat liver microsomes.
PubMed:
Urinary excretion of arginine-vasopressin and prostaglandin E2 in essential fatty acid-deficient rats after oral supplementation with unsaturated fatty acid esters.
PubMed:
A unique cardiac cytosolic acyltransferase with preferential selectivity for fatty acids that form cyclooxygenase/lipoxygenase metabolites and reverse essential fatty acid deficiency.
PubMed:
Physiologic effects of columbinic acid and its metabolites on rat skin.
PubMed:
Essential function of linoleic acid esterified in acylglucosylceramide and acylceramide in maintaining the epidermal water permeability barrier. Evidence from feeding studies with oleate, linoleate, arachidonate, columbinate and alpha-linolenate.
PubMed:
The metabolic transformations of columbinic acid and the effect of topical application of the major metabolites on rat skin.
PubMed:
The non-eicosanoid functions of the essential fatty acids.
PubMed:
Effect of fatty acids of omega 6 series on the biosynthesis of arachidonic acid in HTC cells.
PubMed:
Effect of specific dietary fatty acids on lipogenesis in the livers and mammary glands of lactating mice.
PubMed:
Effect of dietary 18-carbon fatty acids on growth of transplantable mammary adenocarcinomas in mice.
PubMed:
Columbinic acid, a new type of essential fatty acid.
PubMed:
The manipulation of the fatty acid composition of Dictyostelium discoideum and its effect on cell differentiation.