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linoleic and linolenic acids
linoleic and linolenic acid (mixture)

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Name:(9Z,12Z)-octadeca-9,12-dienoic acid; (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
CAS Number: 60-33-3 (N)Picture of molecule3D/inchi
Other(deleted CASRN):8024-22-4
Molecular Weight:558.88694000
Formula:C36 H62 O4
NMR Predictor:Predict (works with chrome, Edge or firefox)
Also(can) Contains:linolenic acid
 linoleic acid
EFSA/JECFA Comments:
44-46% linolenic acid; 18-20% linoleic acid; 22-25% stearic and oleic acid; 7-8% palmitic acid. (JECFA)
Category:cosmetic, flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Perfumer and Flavorist:Search
Google Patents:Search
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JECFA Food Flavoring:332 linoleic and linolenic acid (mixture)
FEMA Number:3380 linoleic and linolenic acid (mixture)
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF):977043-76-7 ; 9,12-OCTADECADIENOIC ACID (48%) AND 9,12,15-OCTADECATRIENOIC ACID (52%)
Physical Properties:
Food Chemicals Codex Listed: No
Boiling Point: 365.20 °C. @ 760.00 mm Hg
logP (o/w): 7.050
Soluble in:
 water, 0.03771 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor Strength:none
Odor Description:at 100.00 %. faint fatty
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antistatic agents
cleansing agents
hair conditioning
skin conditioning
skin conditioning - emollient
Alfa Biotechnology
For experimental / research use only.
Linoleic acid 95%
Linolenic Acid (52%) With Linoleic Acid (48%)
Tianjin Danjun International
Linoleic acid
Linoleic acid
Chemical Sources Association
Need This Item for Flavor/Food?: You can contact the Chemical Sources Association
Safety Information:
European information :
Most important hazard(s):
Xi - Irritant
R 36 - Irritating to eyes.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
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
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LD50 280 mg/kg
Yakugaku Zasshi. Journal of Pharmacy. Vol. 104, Pg. 793, 1984.

oral-mouse LD50 > 50000 mg/kg
United States Patent Document. Vol. #3728459

intraperitoneal-rat LD50 > 50000 mg/kg
Oyo Yakuri. Pharmacometrics. Vol. 4, Pg. 327, 1970.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
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
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: 6
Click here to view publication 6
 average usual ppmaverage maximum ppm
baked goods: -15.00000
beverages(nonalcoholic): -15.00000
beverages(alcoholic): -15.00000
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: -15.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -15.00000
fruit ices: -15.00000
gelatins / puddings: -15.00000
granulated sugar: --
gravies: --
hard candy: -15.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: -15.00000
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):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 6 (FGE.06): Straight-and branched-chain aliphatic unsatured primary alcohols, aldehydes, carboxylic acids, and esters from chemical groups 1 and 4
View page or View pdf

Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC) on a request from the Commission related to Flavouring Group Evaluation 5: Esters of 23 branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and 24 branched- and straight-chain unsaturated carboxylic acids from chemical groups 1, 2, and 5
View page or View pdf

Flavouring Group Evaluation 6, Revision 1 (FGE.06Rev1) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 5, Revision 1 (FGE.05Rev1):Esters of branched- and straight-chain aliphatic saturated primary alcohols and of one secondary alcohol, and branched- and straight-chain unsaturated carboxylic acids from chemical groups 1, 2, and 5 (Commission Regulation (EC) No 1565/2000 of 18 July 2000) [1] - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 29 (FGE29)[1] - Substance from the priority list: Vinylbenzene from chemical group 31 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food (AFC)
View page or View pdf

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :9937654
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(9Z,12Z)-octadeca-9,12-dienoic acid; (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
EPA/NOAA CAMEO:hazardous materials
 (9Z,12Z)-octadeca-9,12-dienoic acid; (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:60-33-3
Pubchem (cid):9937654
Pubchem (sid):134972931
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
FDA Substances Added to Food (formerly EAFUS):View
KEGG (GenomeNet):C01595
HMDB (The Human Metabolome Database):HMDB00673
YMDB (Yeast Metabolome Database):YMDB00884
Export Tariff Code:2916.15.1000
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
 antistatic agents
 hair conditioning
 skin conditioning
Occurrence (nature, food, other):note
 ophrys exaltata
Search Trop Picture
 zizyphus mauritiana
Search Trop Picture
 linoleic (48%) and linolenic (52%) acids
 linoleic and linolenic acid (mixture)
 linolenic (52%) acids and linoleic (48%)
 octadeca-9,12-dienoic acid and octadeca-9,12,15-trienoic acid
(9Z,12Z)-octadeca-9,12-dienoic acid; (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid
 octadeca-9,12,15-trienoic acid and octadeca-9,12-dienoic acid
 octadecadienoic acid (48%) + 9,12- & 9,12,15-octadecatrienoic acid (52%)
9,12-octadecadienoic acid (48%) and 9,12,15-octadecatrienoic acid (52%)
9,12,15-octadecatrienoic acid (52%) and 9,12-octadecadienoic acid (48%)


PubMed:Subcutaneous adipose fatty acid profiles and related rumen bacterial populations of steers fed red clover or grass hay diets containing flax or sunflower-seed.
PubMed:Effects of 1-year intervention with a mediterranean diet on plasma Fatty acid composition and metabolic syndrome in a population at high cardiovascular risk.
PubMed:Types of oilseed and adipose tissue influence the composition and relationships of polyunsaturated fatty acid biohydrogenation products in steers fed a grass hay diet.
PubMed:Protective effects of dietary PUFA against chronic disease: evidence from epidemiological studies and intervention trials.
PubMed:Oxylipins generation in Lactobacillus helveticus in relation to unsaturated fatty acid supplementation.
PubMed:Fatty acid profile, color and lipid oxidation of meat from young bulls fed ground soybean or rumen protected fat with or without monensin.
PubMed:Jacaric acid is rapidly metabolized to conjugated linoleic acid in rats.
PubMed:At line prediction of PUFA and biohydrogenation intermediates in perirenal and subcutaneous fat from cattle fed sunflower or flaxseed by near infrared spectroscopy.
PubMed:Determination of thermally induced trans-fatty acids in soybean oil by attenuated total reflectance fourier transform infrared spectroscopy and gas chromatography analysis.
PubMed:Fatty acid profile, trans-octadecenoic, α-linolenic and conjugated linoleic acid contents differing in certified organic and conventional probiotic fermented milks.
PubMed:A 4-week repeated oral dose toxicity study of dairy fat naturally enriched in vaccenic, rumenic and α-linolenic acids in rats.
PubMed:Influence of colour type and previous cultivation on secondary metabolites in hypocotyls and leaves of maca (Lepidium meyenii Walpers).
PubMed:Improving the fatty acid profile of dairy cow milk by combining grazing with feeding of total mixed ration.
PubMed:Prooxidant activity of oxidized alpha-tocopherol in vegetable oils.
PubMed:Incorporation and metabolism of punicic acid in healthy young humans.
PubMed:Punicic acid from Trichosanthes kirilowii seed oil is rapidly metabolized to conjugated linoleic acid in rats.
PubMed:Oxidative stability of conjugated linolenic acids.
PubMed:Fatty acid, triacylglycerol, and phytosterol composition in six Tunisian olive varieties.
PubMed:Effects of cis-9,trans-11 and trans-10,cis-12 CLA isomers on liver and adipose tissue fatty acid profile in hamsters.
PubMed:Analysis of alpha-linolenic acid biohydrogenation intermediates in milk fat with emphasis on conjugated linolenic acids.
PubMed:Inhibitory action of conjugated C18-fatty acids on DNA polymerases and DNA topoisomerases.
PubMed:Alpha-eleostearic acid (9Z11E13E-18:3) is quickly converted to conjugated linoleic acid (9Z11E-18:2) in rats.
PubMed:Recommended methods of fatty acid methylester preparation for conjugated dienes and trienes in food and biological samples.
PubMed:Methods for analysis of conjugated linoleic acids and trans-18:1 isomers in dairy fats by using a combination of gas chromatography, silver-ion thin-layer chromatography/gas chromatography, and silver-ion liquid chromatography.
PubMed:Influence of harvest date and crop yield on the fatty acid composition of virgin olive oils from cv. Picual.
PubMed:Tumor growth suppression by alpha-eleostearic acid, a linolenic acid isomer with a conjugated triene system, via lipid peroxidation.
PubMed:Comparative methyl linoleate and methyl linolenate oxidation in the presence of bovine serum albumin at several lipid/protein ratios.
PubMed:The metabolic conversion of 9,11,13-eleostearic acid (18:3) to 9,11-conjugated linoleic acid (18:2) in the rat.
PubMed:Nutritional profile of food yeast Kluyveromyces fragilis biomass grown on whey.
PubMed:Purification of hydroperoxide lyase from green bell pepper (Capsicum annuum L.) fruits for the generation of C6-aldehydes in vitro.
PubMed:Extension of AOAC Official Method 996.01 to the analysis of Standard Reference Material (SRM) 1846 and infant formulas.
PubMed:Fatty acid composition of lipids in sea buckthorn (Hippophaë rhamnoides L.) berries of different origins.
PubMed:Linoleic and alpha-linolenic acids differently modify the effects of elaidic acid on polyunsaturated fatty acid metabolism and some immune indices in rats.
PubMed:Comparative hypocholesterolemic effects of capybara (Hydrochoerus hydrochaeris dabbenei) oil, horse oil, and sardine oil in cholesterol-fed rats.
PubMed:Simultaneous determination of acrolein, malonaldehyde and 4-hydroxy-2-nonenal produced from lipids oxidized with Fenton's reagent.
PubMed:Medium-chain triacylglycerols in formulas for preterm infants: effect on plasma lipids, circulating concentrations of medium-chain fatty acids, and essential fatty acids.
PubMed:Inhibitory effect of 2"-O-glycosyl isovitexin and alpha-tocopherol on genotoxic glyoxal formation in a lipid peroxidation system.
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:Application of the balance method to determining accumulation, metabolism, and apparent oxidation of linoleic and alpha-linolenic acids in the pregnant rat.
PubMed:Dietary linoleic, alpha-linolenic and oleic acids are oxidized at similar rates in rats fed a diet containing these acids in equal proportions.
PubMed:Carotenoid scavenging of radicals. Effect of carotenoid structure and oxygen partial pressure on antioxidative activity.
PubMed:Low zinc intake increases apparent oxidation of linoleic and alpha-linolenic acids in the pregnant rat.
PubMed:Borage or primrose oil added to standardized diets are equivalent sources for gamma-linolenic acid in rats.
PubMed:Arachidonic acid concentrations in plasma and liver phospholipid and cholesterol esters of piglets raised on formulas with different linoleic and linolenic acid contents.
PubMed:Determination of the optimal ratio of linoleic acid to alpha-linolenic acid in infant formulas.
PubMed:Long chain omega 3 polyunsaturates in formula-fed term infants.
PubMed:Alpha-linolenic acid: functions and effects on linoleic acid metabolism and eicosanoid-mediated reactions.
PubMed:Effects of dietary oleic, linoleic and alpha-linolenic acids on blood pressure, serum lipids, lipoproteins and the formation of eicosanoid precursors in patients with mild essential hypertension.
PubMed:[Does food affect brain functions?].
PubMed:The requirements and utilization of dietary fatty acids in the newborn infant.
PubMed:The effects of dietary alpha-linolenic acid on the composition of nerve membranes, enzymatic activity, amplitude of electrophysiological parameters, resistance to poisons and performance of learning tasks in rats.
PubMed:FDA alert on evening primrose oil.
PubMed:[A supplement with poly-unsaturated nutrients in the development and stabilization of the rat brain].
PubMed:Linoleic acid and linolenic acid: effect on permeability properties of cultured endothelial cell monolayers.
PubMed:[Current recommendations concerning rational use of fats. II. Value of polyunsaturated fatty acids from the n-6 and n-3 groups and general recommendations].
PubMed:Effects of dietary poly-unsaturated fatty acids on tracheal histaminergic and cholinergic responsiveness in experimental models of bronchial hypersensitivity and hyperreactivity.
PubMed:Comparison of the metabolism of linoleic and linolenic acids in the fetal rat.
PubMed:Pain, prostaglandins, and food lipids. Influences of dietary polyunsaturated fatty acids on eicosanoid synthesis and effects.
PubMed:Increased requirements for essential fatty acids in atopic individuals: a review with clinical descriptions.
PubMed:Mutagenicity tests of lipid oxidation products in Salmonella typhimurium: monohydroperoxides and secondary oxidation products of methyl linoleate and methyl linolenate.
PubMed:[Nutrition physiology studies with formula diets: metabolism of multiple unsaturated fatty acids and prostaglandin biosynthesis in the human].
PubMed:Dietary fat, prostaglandins and the immune response.
PubMed:Volatile lipid oxidation products.
PubMed:Decrease in essential fatty acid content of edible fats during the frying process.
PubMed:Cardiovascular effects of linoleic acid.
PubMed:Haemostatic function and polyunsaturated fatty acids.
PubMed:Effects of all cis-5,8,11,14,17 eicosapentaenoic acid and PGH3 on platelet aggregation.
PubMed:Anorectic activity of prostaglandin precursors.
PubMed:Improved procedures for the isolation of pure oleic, linoleic, and linolenic acids or their methyl esters from natural sources.
PubMed:Specific inhibition of hepatic fatty acid synthesis exerted by dietary linoleate and linolenate in essential fatty acid adequate rats.
PubMed:Essential fatty acid requirements in infancy.
PubMed:Essential fatty acids and fetal brain growth.
PubMed:Long-chain polyunsaturated fatty acids in the mammalian brain.
PubMed:Differences in the amount and range of volatile carbonyl compounds formed by lipoxygenase isoenzymes from soybeans.
PubMed:Lipid autoxidation in precooked dehydrated sweet potato flakes stored in air.
PubMed:The component fatty acids of Aspergillus ochraceus fat.
PubMed:[Results of comparative analyses of linoleic and linolenic acids in the laboratories of CSSR].
PubMed:Evaluation of modern foods as sources of lipids. In: lipids, malnutrition & the developing brain.
extractives and their physically modified derivatives. vitis, vitidaceae. Used as a food additive [EAFUS]
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