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methyl linoleate

Chemical Structure

General Material Information

Preferred name methyl linoleate
Trivial Name Methyl linoleate
Short Description methyl 9-cis,12-cis-octadecadienoate
Formula C19 H34 O2
CAS Number 112-63-0
Deleted CAS Number 1198018-53-9
FEMA Number 3411
ECHA Number 203-993-0
FDA UNII 24N6726DE5
Nikkaji Number J1.998D
Beilstein Number 1727614
MDL MFCD00009534
COE Number 713
xLogP3-AA 6.90 (est)
Bio Activity Summary External link
NMR Predictor External link
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • linoleic acid methyl ester
  • linoleic acid, methyl ester
  • methyl (9Z,12Z)-9,12-octadecadienoate
  • methyl (9Z,12Z)-octadeca-9,12-dienoate
  • methyl (Z,Z)-9,12-octadecadienoate
  • methyl 9-cis,12-cis-octadecadienoate
  • methyl cis,cis-9,12-octadecadienoate
  • methyl lineoleate
  • methyl octadecadienoate
  • methyllinoleate
  • 9,12-octadecadienoic acid (9Z,12Z)-, methyl ester
  • 9,12-octadecadienoic acid (Z,Z)-, methyl ester
  • (9Z,12Z)- octadecadienoic acid methyl ester
  • (Z,Z)-9,12-octadecadienoic acid methyl ester
  • octadecadienoic acid methyl ester, 9,12-(Z,Z)-
  • 9,12-octadecadienoic acid, methyl ester, (9Z,12Z)-
  • 9,12-octadecadienoic acid, methyl ester, (Z,Z)-
  • 9,12-Octadecadienoic acid (9Z,12Z)-, methyl ester
  • 9,12-Octadecadienoic acid (Z,Z)-, methyl ester
  • Methyl cis-9,cis-12 linoleate
  • Methyl cis-9,cis-12-octadecadienoate
  • Methyl (9Z,12Z)-octadecadienoate
  • (9Z,12Z)-Octadecadienoic acid methyl ester
  • Methyl octadec-9,12-dienoate
  • (9Z,12Z)-9,12-Octadecadienoic acid methyl ester
  • Radia 7062
  • (Z,Z)-9,12-Octadecadienoic acid methyl ester
  • 9Z,12Z-Octadedecadienoic acid methyl ester

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Literature & References

methyl (9Z,12Z)-octadeca-9,12-dienoate
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:112-63-0
Pubchem (cid):5284421
Pubchem (sid):134973524
Pherobase:View
Publications by PubMed
Effect of olive storage conditions on Chemlali olive oil quality and the effective role of fatty acids alkyl esters in checking olive oils authenticity.
Effects of various emulsification methods on the oxidation of methyl linoleate.
Effect of boiling in water of barley and buckwheat groats on the antioxidant properties and dietary fiber composition.
Nonallergenic urushiol derivatives inhibit the oxidation of unilamellar vesicles and of rat plasma induced by various radical generators.
Effect of droplet size on autoxidation rates of methyl linoleate and α-linolenate in an oil-in-water emulsion.
Synthesis of linoleoyl ethanolamide.
UVA photoirradiation of benzo[a]pyrene metabolites: induction of cytotoxicity, reactive oxygen species, and lipid peroxidation.
UVA photoirradiation of nitro-polycyclic aromatic hydrocarbons-induction of reactive oxygen species and formation of lipid peroxides.
Riboflavin-photosensitized oxidation is enhanced by conjugation in unsaturated lipids.
Phototoxicity of kava - formation of reactive oxygen species leading to lipid peroxidation and DNA damage.
Statistical optimization of culture media for growth and lipid production of Chlorella protothecoides UTEX 250.
Kinetic study of Sasa veitchii extract as a radical scavenger and an antioxidant.
Green tea extract as food antioxidant. Synergism and antagonism with α-tocopherol in vegetable oils and their colloidal systems.
Antioxidant activity of isolated ellagitannins from red raspberries and cloudberries.
Photoirradiation of dehydropyrrolizidine alkaloids--formation of reactive oxygen species and induction of lipid peroxidation.
Photoirradiation of polycyclic aromatic hydrocarbon diones by UVA light leading to lipid peroxidation.
Design of Ru-zeolites for hydrogen-free production of conjugated linoleic acids.
Culture of microalgae Chlorella minutissima for biodiesel feedstock production.
Preparation of acetonides from soybean oil, methyl soyate, and fatty esters.
Light-induced oxidation of unsaturated lipids as sensitized by flavins.
Properties of synthetic homoisoflavonoids to reduce oxidants and to protect linoleic acid and dna against oxidation.
Assessing palatability of long-chain fatty acids from the licking behavior of BALB/c mice.
Unusual antioxidant behavior of alpha- and gamma-terpinene in protecting methyl linoleate, DNA, and erythrocyte.
Quantification of antioxidant capacity in a microemulsion system: synergistic effects of chlorogenic acid with alpha-tocopherol.
Analytical evaluation of polyunsaturated fatty acids degradation during thermal oxidation of edible oils by Fourier transform infrared spectroscopy.
In vitro digestion of betalainic foods. Stability and bioaccessibility of betaxanthins and betacyanins and antioxidative potential of food digesta.
UVA photoirradiation of anhydroretinol--formation of singlet oxygen and superoxide.
Kaiware Daikon (Raphanus sativus L.) extract: a naturally multipotent chemopreventive agent.
Contribution of lipid oxidation products to acrylamide formation in model systems.
Azide derivatives of soybean oil and fatty esters.
UVA photoirradiation of oxygenated benz[a]anthracene and 3-methylcholanthene--generation of singlet oxygen and induction of lipid peroxidation.
Effect of oil-droplet size on the oxidation of microencapsulated methyl linoleate.
Bioactive components of caper (Capparis spinosa L.) from Sicily and antioxidant effects in a red meat simulated gastric digestion.
Efficacy of metmyoglobin and hemin as a catalyst of lipid peroxidation determined by using a new testing system.
Photo-irradiation of Aloe vera by UVA--formation of free radicals, singlet oxygen, superoxide, and induction of lipid peroxidation.
Elucidation of structural isomers from the homogeneous rhodium-catalyzed isomerization of vegetable oils.
High-throughput quantitation of peroxyl radical scavenging capacity in bulk oils.
Photoirradiation of retinyl palmitate in ethanol with ultraviolet light--formation of photodecomposition products, reactive oxygen species, and lipid peroxides.
Photoirradiation of representative polycyclic aromatic hydrocarbons and twelve isomeric methylbenz[a]anthracene with UVA light: formation of lipid peroxidation.
Isolation and characterization of rosmarinic acid oligomers in Celastrus hindsii Benth leaves and their antioxidative activity.
ESR and NMR spectroscopy studies on protein oxidation and formation of dityrosine in emulsions containing oxidised methyl linoleate.
Dual positional and stereospecificity of lipoxygenase isoenzymes from germinating barley (green malt): biotransformation of free and esterified linoleic acid.
Free-radical-scavenging and antioxidant activities of secondary metabolites from reddened cv. Annurca apple fruits.
UVA photoirradiation of retinyl palmitate--formation of singlet oxygen and superoxide, and their role in induction of lipid peroxidation.
Synthesis of carbonated fatty methyl esters using supercritical carbon dioxide.
Catechins and procyanidins in berries of vaccinium species and their antioxidant activity.
Antioxidative compounds from the outer scales of onion.
Antioxidant activity of steryl ferulate extracts from rye and wheat bran.
Antioxidant activity of olive pulp and olive oil phenolic compounds of the arbequina cultivar.
Antioxidative polyphenols from berries of Pimenta dioica.
Photodecomposition of retinyl palmitate in ethanol by UVA light-formation of photodecomposition products, reactive oxygen species, and lipid peroxides.
Antioxidant properties of gingerol related compounds from ginger.
Total phenolics and antioxidant activities of fenugreek, green tea, black tea, grape seed, ginger, rosemary, gotu kola, and ginkgo extracts, vitamin E, and tert-butylhydroquinone.
Myoglobin species with enhanced prooxidative activity is formed during mild proteolysis by pepsin.
Comparative methyl linoleate and methyl linolenate oxidation in the presence of bovine serum albumin at several lipid/protein ratios.
ELISA for monitoring lipid oxidation in chicken myofibrils through quantification of hexanal-protein adducts.
Antioxidative activities of volatile extracts from green tea, oolong tea, and black tea.
Effects of oral stimulation with fats on the cephalic phase of pancreatic enzyme secretion in esophagostomized rats.
Chain-breaking antioxidant activity and cyclic voltammetry characterization of polyphenols in a range of green, oolong, and black teas.
Isolation and characterization of some antioxidative compounds from the rhizomes of smaller galanga (Alpinia officinarum Hance).
Solid phase microextraction-gas chromatography for quantifying headspace hexanal above freeze-dried chicken myofibrils.
Nonradiometric HPLC measurement of 13(S)-hydroxyoctadecadienoic acid from rat tissues.
Preparation of a t,t conjugated linoleic acid methylester (CLA-Me) isomers mixture from synthetic CLA by methylation with BF3/methanol.
Studies on dimerisation of tocopherols under the influence of methyl linoleate peroxides.
Commercial dietary antioxidant supplements assayed for their antioxidant activity by different methodologies.
Chain-Breaking Antioxidant Capability of Some Beverages as Determined by the Clark Electrode Technique.
Antioxidant activity of anthocyanins and their aglycons.
Antioxidant constituents of almond [Prunus dulcis (Mill.) D.A. Webb] hulls.
Antioxidant activity and characterization of volatile constituents of Taheebo (Tabebuia impetiginosa Martius ex DC).
Antioxidant synergy and regeneration effect of quercetin, (-)-epicatechin, and (+)-catechin on alpha-tocopherol in homogeneous solutions of peroxidating methyl linoleate.
Antioxidant properties of differently processed spinach products.
Methyl linoleate oxidation in the presence of bovine serum albumin.
Ability of lipid hydroperoxides to partition into surfactant micelles and alter lipid oxidation rates in emulsions.
Determination of antioxidant potential of volatile extracts isolated from various herbs and spices.
Effects of riboflavin and fatty acid methyl esters on cholesterol oxidation during illumination.
Effect of nitrosylmyoglobin and saturated fatty acid anions on metmyoglobin-catalyzed oxidation of aqueous methyl linoleate emulsions.
Antioxidant properties of ferulic acid and its related compounds.
Antioxidant activity of chemical components from sage (Salvia officinalis L.) and thyme (Thymus vulgaris L.) measured by the oil stability index method.
Effect of lipid composition on meat-like model systems containing cysteine, ribose, and polyunsaturated fatty acids.
Formation of polycyclic aromatic hydrocarbons in the smoke from heated model lipids and food lipids.
Impact of tween 20 hydroperoxides and iron on the oxidation of methyl linoleate and salmon oil dispersions.
Berry phenolics and their antioxidant activity.
Extension of AOAC Official Method 996.01 to the analysis of Standard Reference Material (SRM) 1846 and infant formulas.
Antioxidant mechanism of flavonoids. Solvent effect on rate constant for chain-breaking reaction of quercetin and epicatechin in autoxidation of methyl linoleate.
Antioxidant Activity of Berry and Fruit Wines and Liquors.
Identification, quantitative determination, and antioxidative activities of chlorogenic acid isomers in prune (Prunus domestica L. ).
Interaction of gum arabic, maltodextrin and pullulan with lipids in emulsions.
Ability of surfactant hydrophobic tail group size to alter lipid oxidation in oil-in-water emulsions.
Ability of surfactant headgroup size to alter lipid and antioxidant oxidation in oil-in-water emulsions.
Identification of new geometric isomers of methyl linoleate hydroperoxide and their chromatographic behavior.
Isolation and structure determination of new antioxidative ferulic acid glucoside esters from the rhizome of Alpinia speciosa, a Zingiberaceae plant used in Okinawan food culture.
Antioxidant properties of a North American ginseng extract.
Peroxidation of linoleate at physiological pH: hemichrome formation by substrate binding protects against metmyoglobin activation by hydrogen peroxide.
Antioxidant activity and partitioning of phenolic acids in bulk and emulsified methyl linoleate.
Antioxidant activity of plant extracts containing phenolic compounds.
Effect of pH and temperature on comparative antioxidant activity of nonenzymatically browned proteins produced by reaction with oxidized lipids and carbohydrates.
Effect of pH and temperature on comparative nonenzymatic browning of proteins produced by oxidized lipids and carbohydrates.
Change in the positional specificity of lipoxygenase 1 due to insertion of fatty acids into phosphatidylcholine deoxycholate mixed micelles.
Proportion of geometrical hydroperoxide isomers generated by radical oxidation of methyl linoleate in homogeneous solution and in aqueous emulsion.
The orosensory recognition of long-chain fatty acids in rats.
Antioxidative activities of several marine polysaccharides evaluated in a phosphatidylcholine-liposomal suspension and organic solvents.
Reaction of alpha-tocopherol in heated bulk phase in the presence of methyl linoleate (13S)-hydroperoxide or methyl linoleate.
Determination of hydroperoxides and structures by high-performance liquid chromatography with post-column detection with diphenyl-1-pyrenylphosphine.
Effect of alpha-tocopherol and Trolox on the decomposition of methyl linoleate hydroperoxides.
Estimation of essential fatty acid requirements of common carp larvae using semi-purified artificial diets.
Recognition system for dietary fatty acids in the rat small intestine.
The recognition system of dietary fatty acids by the rat small intestinal cells.
Radioprotective effect of antioxidative flavonoids in gamma-ray irradiated mice.
Antioxidant activity of 9-cis compared to all-trans beta-carotene in vitro.
Protective effect of epicatechin, epicatechin gallate, and quercetin on lipid peroxidation in phospholipid bilayers.
Carotenoid scavenging of radicals. Effect of carotenoid structure and oxygen partial pressure on antioxidative activity.
Reaction of alpha-tocopherol with alkyl and alkylperoxyl radicals of methyl linoleate.
Evaluation of immunochemical changes in ovalbumin due to reaction with oxidizing methyl linoleate by an enzyme linked immunosorbent assay.
The inhibitory effect of water on the Co2+ and Cu2+ catalyzed decomposition of methyl linoleate hydroperoxides.
Properties of agents that effectively entrap liquid lipids.
Comparison of the cytotoxicity of different hydroperoxides to V79 cells.
In vivo effects of single or combined dietary antimutagens on mutagen-induced chromosomal aberrations.
Solvent effects in the spin trapping of lipid oxyl radicals.
Rapid headspace gas chromatography of hexanal as a measure of lipid peroxidation in biological samples.
The effect of dietary autoxidized oils on immunocompetent cells in mice.
Antioxidant activity of beta-carotene-related carotenoids in solution.
Multiple forms of glutathione S-transferase from pig liver--reaction with methyl linoleate hydroperoxides.
Characterization of fluorescent products from reaction of methyl linoleate hydroperoxides with adenine in the presence of Fe2+ and ascorbic acid.
The effect of dietary lipid hydroperoxide on lymphoid tissues in mice.
Microcomputer-based system for data acquisition and analysis of oxygen uptake studies.
Effects of relative humidity on lipid autoxidation in a model system.
Effect of dietary lipid peroxides on lymphoid tissues.
Quantitative determination of linoleic acid in infant formulas by gas chromatography.
Limitations of the hemoglobin method for detecting lipid hydroperoxides.
Mutagenicity tests of lipid oxidation products in Salmonella typhimurium: monohydroperoxides and secondary oxidation products of methyl linoleate and methyl linolenate.
Effects of methyl linoleate hydroperoxide and hydrogen peroxide on N-nitrosation of dimethylamine.
Effect of organic solvents and unsaturated fatty acids on nitrosamine formation.
Changes in lysozyme due to reactions with volatile products of peroxidizing methyl linoleate.
The effect of ionizing radiation on the fatty acid composition of natural fats and on lipid peroxide formation.
Reactions between peroxidizing lipids and histidyl residue analogues: enhancement of lipid oxidation and browning by 4-methylimidazole.
Changes in lysozyme due to reactions with peroxidizing methyl linoleate in a dehydrated model system.
Interaction of peroxidizing methyl linoleate with some proteins and amino acids.
Minor peroxide components as catalysts and precursors to monocarbonyls in the autoxidation of methyl linoleate.
Effects of model system composition on autoxidation of methyl linoleate.
Publications by J-Stage
The Antioxidative Effect of Fullerenes during the Peroxidation of Methyl Linoleate in Toluene

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
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
HMDB (The Human Metabolome Database):HMDB34381
FooDB:FDB012761
Export Tariff Code:2916.15.1000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 294.47839355469
Specific gravity @ 20 °C
Pounds per Gallon 7.381 to 7.414
Refractive Index 1.46 to 1.463 @ 20 °C
Boiling Point 373 to 374°C @ 760 mm Hg
Vapor Pressure 9.0E-6 mmHg @ 25 °C
Flash Point TCC Value 110 °C TCC
logP (o/w) 6.82
Shelf life 12 months (or longer if stored properly.)
Storage notes Refrigerate in tightly sealed containers.
Solubility
alcohol Yes
water, 0.01981 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

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

Occurrences

Safety Information

Safety information

Preferred SDS: View
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:
cosmetic, 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 linoleate usage levels up to:
20.0000 % in the fragrance concentrate.
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 7
Click here to view publication 7
average usual ppmaverage maximum ppm
baked goods: -10.00000
beverages(nonalcoholic): -10.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: -10.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -10.00000
fruit ices: -10.00000
gelatins / puddings: -10.00000
granulated sugar: --
gravies: --
hard candy: -10.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: -10.00000
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Authority (EFSA) reference(s):

Efficacy of methyl ester of conjugated linoleic acid (t10,c12 isomer) for sows and cows for reproduction
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA Substance Registry Services (TSCA):112-63-0
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5284421
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
methyl (9Z,12Z)-octadeca-9,12-dienoate
Chemidplus:0000112630