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methyl linolenate

General Material Information

Preferred name methyl linolenate
Trivial Name methyl octadeca-9,12,15-trienoate
Short Description methyl 9,12,15-octadecatrienoate
Formula C19 H32 O2
CAS Number 7361-80-0
FDA UNII Search
xLogP3-AA 6.20 (est)
Bio Activity Summary External link
NMR Predictor External link
Synonyms
  • linolenic acid methyl ester
  • methyl 9,12,15-octadecatrienoate
  • methyl octadeca-9,12,15-trienoate
  • octadeca-9,12,15-trienoic acid methyl ester
  • 9,12,15-octadecatrienoic acid methyl ester
  • 9,12,15-octadecatrienoic acid, methyl ester

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Literature & References

methyl octadeca-9,12,15-trienoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):9316
Pubchem (sid):135051444
Pherobase:View
Publications by PubMed
Profile of volatile components of hydrodistilled and extracted leaves of Jacaranda acutifolia and their antimicrobial activity against foodborne pathogens.
Selective oxidation reactions of natural compounds with hydrogen peroxide mediated by methyltrioxorhenium.
Statistical optimization of culture media for growth and lipid production of Chlorella protothecoides UTEX 250.
Rate constants of oxidation of unsaturated fatty esters studied by chemiluminescence.
Activity of compounds isolated from Baccharis dracunculifolia D.C. (Asteraceae) against Paracoccidioides brasiliensis.
Antimicrobial and antioxidant activities of the flower essential oil of Halimodendron halodendron.
Antimicrobial investigation of Linum usitatissimum for the treatment of acne.
Culture of microalgae Chlorella minutissima for biodiesel feedstock production.
[Autooxidation of a mixture of lemon essential oils, methyl linolenoate, and methyl oleinate].
Melanogenesis inhibitory effect of fatty acid alkyl esters isolated from Oxalis triangularis.
Phenolic profiles and antioxidant properties of apple skin extracts.
Light-induced oxidation of unsaturated lipids as sensitized by flavins.
One-pot process combining transesterification and selective hydrogenation for biodiesel production from starting material of high degree of unsaturation.
Inhibition of oxidation of aqueous emulsions of omega-3 fatty acids and fish oil by phloretin and phloridzin.
Marine diatom, Navicula sp. strain JPCC DA0580 and marine green alga, Chlorella sp. strain NKG400014 as potential sources for biodiesel production.
Solid phase extraction and enrichment of essential fatty acid methyl esters from soy-derived biodiesel by novel pi-complexing sorbents.
[Determination of 11 fatty acids and fatty acids methyl esters in biodiesel using ultra performance liquid chromatography].
Combined analysis of C-18 unsaturated fatty acids using natural abundance deuterium 2D NMR spectroscopy in chiral oriented solvents.
Linoleic acid induces Ca2+-induced inactivation of voltage-dependent Ca2+ currents in rat pancreatic beta-cells.
Multivariate near infrared spectroscopy models for predicting the methyl esters content in biodiesel.
A direct and fast method to monitor lipid oxidation progress in model fatty acid methyl esters by high-performance size-exclusion chromatography.
[Cloning and expression of delta6-desaturase gene from Thamnidium elegans in Saccharomyces cerevisiae].
Identification of 4-oxo-2-hexenal and other direct mutagens formed in model lipid peroxidation reactions as dGuo adducts.
Impact of lipid physical state on the oxidation of methyl linolenate in oil-in-water emulsions.
4-oxo-2-hexenal, a mutagen formed by omega-3 fat peroxidation, causes DNA adduct formation in mouse organs.
Evaluation of activity of selected antioxidants on proteins in solution and in emulsions.
[Contrastive analysis of volatile oil from Serissa serissoides in different seasons].
Comparative methyl linoleate and methyl linolenate oxidation in the presence of bovine serum albumin at several lipid/protein ratios.
Effect of quercetin and genistein on copper- and iron-induced lipid peroxidation in methyl linolenate.
Formation of polycyclic aromatic hydrocarbons in the smoke from heated model lipids and food lipids.
Superoxide dismutase inhibits lipid peroxidation in micelles.
Extension of AOAC Official Method 996.01 to the analysis of Standard Reference Material (SRM) 1846 and infant formulas.
Modifications of proteins by polyunsaturated fatty acid peroxidation products.
Determination of hydroperoxides and structures by high-performance liquid chromatography with post-column detection with diphenyl-1-pyrenylphosphine.
An improved method for rapid analysis of the fatty acids of glycerolipids.
Estimation of essential fatty acid requirements of common carp larvae using semi-purified artificial diets.
Oxidative DNA damage induced by potassium bromate in isolated rat renal proximal tubules and renal nuclei.
Carotenoid scavenging of radicals. Effect of carotenoid structure and oxygen partial pressure on antioxidative activity.
The identification of the allylic nitrite and nitro derivatives of methyl linoleate and methyl linolenate by negative chemical ionization mass spectroscopy.
Semiochemical basis of infestation of honey bee brood byVarroa jacobsoni.
Autoxidation and yellowing of methyl linolenate.
Lipid peroxidation products mediate the formation of 8-hydroxydeoxyguanosine in DNA.
Identification of minor C18 triene and conjugated diene isomers in hydrogenated soybean oil and margarine by GC-MI-FT-IR spectroscopy.
Interaction of C-nitroso aromatics with polyunsaturated fatty acids: route to lipid peroxidation.
Arachidonic acid and related methyl ester mediate protein kinase C activation in intact platelets through the arachidonate metabolism pathways.
Free radical scavenging and cytotoxic properties in the ellipticine series.
Rapid headspace gas chromatography of hexanal as a measure of lipid peroxidation in biological samples.
Photoaddition of angelicin to linolenic acid methyl ester.
The biphasic effect of calcium on lipid peroxidation.
Thermal decomposition of methyl linoleate and methyl linolenate hydroperoxides analyzed by capillary gas chromatography.
Fluorescence formation from the interaction of DNA with lipid oxidation degradation products.
Fluorescence formation and heme degradation at different stages of lipid peroxidation.
[Mechanisms of the effects of Ca2+ ions on lipid peroxidation].
Mutagenicity tests of lipid oxidation products in Salmonella typhimurium: monohydroperoxides and secondary oxidation products of methyl linoleate and methyl linolenate.
Site-specific DNA damage caused by lipid peroxidation products.
Reactions of proteins with oxidizing lipids. 2. Influence on protein quality and on the bioavailability of lysine, methionine, cyst(e)ine and tryptophan as measured in rat assays.
Reactions of proteins with oxidizing lipids. 1. Analytical measurements of lipid oxidation and of amino acid losses in a whey protein-methyl linolenate model system.
Identification of ant repellent allomone produced by social waspPolistes fuscatus (Hymenoptera: Vespidae).
Evidence for suitability of glutathione peroxidase as a protective enzyme: studies of oxidative damage, renaturation, and proteolysis.
Peroxidation of tobacco membrane lipids by the photosensitizing toxin, cercosporin.
Effects of linolenic acid deficiency on the fatty acid patterns in plasma and liver cholesteryl esters, triglycerides and phospholipids in female rats.
Decreased formation of porstaglandins derived from arachidonic acid by dietary linolenate in rats.
Participation of superoxide, hydrogen peroxide and hydroxyl radicals in NADPH-cytochrome P-450 reductase-catalyzed peroxidation of methyl linolenate.
Metabolism and lipogenic effects of the cyclic monomers of methyl linolenate in the rat.
Cyclic peroxides from a soya lipoxygenase-catalysed oxygenation of methyl linolenate.
Linolenic acid deficiency: changes in fatty acid patterns in female and male rats raised on a linolenic acid-deficient diet for two generations.
Depletion of docosahexaenoic acid in retinal lipids of rats fed a linolenic acid-deficient, linoleic acid-containing diet.
The occurrence of cis-octadec-15-enoic acid as a major biohydrogenation product from methyl linolenate in bovine rumen liquor.
Autoxidation of polyunsaturated fatty acids. Part I. Effect of ozone on the autoxidation of neat methyl linoleate and methyl linolenate.
Nutritional effects of the cyclic monomers of methyl linolenate in the rat.
Effects of ultraviolet-irradiated methyl linolenate on cell division and respiration in Saccharomyces cerevisiae.

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 292.46243286133
Boiling Point 364 to 365°C @ 760 mm Hg
Vapor Pressure 1.6E-5 mmHg @ 25 °C
Flash Point TCC Value 101.11 °C TCC
logP (o/w) 7.119 est
Solubility
alcohol Yes
water, 0.05771 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Oily
oily, fatty, fruity
Odor strength low
General comment At 100.00 %. bland

Occurrences

Potential Uses

Applications
Other purposes Emollients

Safety Information

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

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for methyl linolenate usage levels up to:
20.0000 % in the fragrance concentrate.

Safety references

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9316
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
methyl octadeca-9,12,15-trienoate
Chemidplus:0007361800