pinolenic acid
trans-5,9,12-octadecatrienoic acid
 
Notes:
None found
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CAS Number: 13237-97-3Picture of molecule3D/inchi
Nikkaji Web: J412.578I
XlogP3-AA: 5.60 (est)
Molecular Weight: 278.43550000
Formula: C18 H30 O2
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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.
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Safety References:
EPI System: View
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 5312493
National Institute of Allergy and Infectious Diseases: Data
 (5E,9E,12E)-octadeca-5,9,12-trienoic acid
Chemidplus: 0013237973
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References:
 (5E,9E,12E)-octadeca-5,9,12-trienoic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 5312493
Pubchem (sid): 135084034
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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Synonyms:
 columbinic acid
(5E,9E,12E)-octadeca-5,9,12-trienoic acid
(E)-5,9,12-octadecatrienoic acid
trans-5,9,12-octadecatrienoic acid
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Articles:
PubMed: Metabolic Conversion of C20 Polymethylene-Interrupted Polyunsaturated Fatty Acids to Essential Fatty Acids.
PubMed: PGE2 production is suppressed by chemically-synthesized Δ7-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.
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