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linoleic acid
cis,cis-9,12-octadecadienoic acid

Sponsors

Name:(9Z,12Z)-octadeca-9,12-dienoic acid
CAS Number: 60-33-3Picture of molecule3D/inchi
Other:8024-22-4
ECHA EINECS - REACH Pre-Reg:200-470-9
FDA UNII:9KJL21T0QJ
Nikkaji Web:J4.801A
Beilstein Number:1727101
MDL:MFCD00064241
CoE Number:694
XlogP3:6.80 (est)
Molecular Weight:280.45144000
Formula:C18 H32 O2
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
Register name to be changed to Linoleic acid.
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 FDA/DG SANTE Petitions, Reviews, Notices:
184.1065 Linoleic acid View-review
JECFA Food Flavoring:332 linoleic acid
FLAVIS Number:08.041 (Old)
DG SANTE Food Flavourings:08.041 linoleic acid
DG SANTE Food Contact Materials:linoleic acid
FDA Mainterm: LINOLEIC ACID
FDA Regulation:
FDA PART 184 -- DIRECT FOOD SUBSTANCES AFFIRMED AS GENERALLY RECOGNIZED AS SAFE
Subpart B--Listing of Specific Substances Affirmed as GRAS
Sec. 184.1065 Linoleic acid.
 
Physical Properties:
Appearance:colorless to pale yellow clear oily liquid (est)
Assay: 99.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.90300 to 0.90600 @ 20.00 °C.
Pounds per Gallon - (est).: 7.523 to 7.548
Refractive Index:1.46800 to 1.47100 @ 20.00 °C.
Melting Point: -5.00 °C. @ 760.00 mm Hg
Boiling Point: 229.00 to 230.00 °C. @ 16.00 mm Hg
Boiling Point: 365.00 to 366.00 °C. @ 760.00 mm Hg
Vapor Pressure:1.000000 mm/Hg @ 180.00 °C.
Vapor Density:9.7 ( Air = 1 )
Flash Point:> 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w): 7.050
Shelf Life: 12.00 month(s) or longer if stored properly.
Storage:refrigerate in tightly sealed containers.
Soluble in:
 alcohol
 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
emollients
hair conditioning
skin conditioning
surfactants
 
Suppliers:
Aceto
Linoleic Acid
Acme Synthetic Chemicals
Linoleic Acid 99% Min. By GC
Amax Nutrasource
Conjugated Linoleic Acid (CLA), 75% (CLA)
Beijing Lys Chemicals
Natural Linoleic acid
BOC Sciences
For experimental / research use only.
(9Z,12Z)-9,12-Octadecadienoic Acid technical
Charkit Chemical
LINOLEIC ACID
Eastman Chemical
Pamolyn™ 210 Linoleic Acid
Odor: characteristic
Use: Pamolyn™ 210 linoleic acid is a high purity grade of linoleic acid derived wholly from a tall oil fatty acid source. It is a pale, oily liquid with low odor, and is highly resistant to discoloration on exposure to heat and light. Because of the near absence of saturated fatty acids, this product has exceptionally low titer. Pamolyn™ 210 linoleic acid contains a low percentage of unsaponifiables and resin acids. Pamolyn™ 210 linoleic acid is designed especially for the protective coatings industry for production of pale, color retentive, fast drying alkyds and epoxy resin ester coatings. Other uses for this linoleic acid are in applications that require both wetting and drying properties, such as printing ink vehicles and caulking and sealant compositions.
ExtraSynthese
For experimental / research use only.
Linoleic Acid (GC) ≥99%
Inoue Perfumery
LINOLEIC ACID
Kraft Chemical
Linoleic Acid
Lluch Essence
LINOLEIC ACID 55%
Penta International
LINOLEIC ACID PURE 99%, Kosher
Penta International
LINOLEIC ACID, CONJUGATED (CLA) 50% POWDER, Kosher
Penta International
LINOLEIC ACID, Kosher
Penta International
LINOLEIC ACID, NATURAL, Kosher
Penta International
LINOLEIC AICD, CONJUGATED (CLA) 80% OIL, Kosher
Sigma-Aldrich
Linoleic acid, ≥95%, FG
Certified Food Grade Products
Sigma-Aldrich
Linoleic acid, ≥95%
Synerzine
Linoleic Acid (Natural)
Synerzine
Linoleic Acid
TCI AMERICA
For experimental / research use only.
Linoleic Acid >97.0%(GC)(T)
 
Safety Information:
Preferred SDS: View
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 36/39 - Wear suitable clothing 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
 
Pictogram
 
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:
Category: flavor and fragrance agents
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 110.00 (μg/capita/day)
 
Safety References:
European Food Safety Athority(efsa):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

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

Flavouring Group Evaluation 5, Revision 2 (FGE.05Rev2): Branched- and straight-chain unsaturated carboxylic acids and esters of these with aliphatic saturated alcohols from chemical groups 1, 2, 3 and 5
View page or View pdf

Review of substances/agents that have direct beneficial effect on the environment: mode of action and assessment of efficacy
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 49, Revision 1 (FGE.49Rev1): xanthine alkaloids from the priority list
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
NLM Hazardous Substances Data Bank:Search
Chemical Carcinogenesis Research Information System:Search
Env. Mutagen Info. Center:Search
NLM Developmental and Reproductive Toxicity:Search
EPA Substance Registry Services (TSCA):60-33-3
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :5280450
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
(9Z,12Z)-octadeca-9,12-dienoic acid
Chemidplus:0000060333
EPA/NOAA CAMEO:hazardous materials
RTECS:RF9990000 for cas# 60-33-3
 
References:
 (9Z,12Z)-octadeca-9,12-dienoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:60-33-3
Pubchem (cid):5280450
Pubchem (sid):134972931
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
KEGG (GenomeNet):C01595
HMDB (The Human Metabolome Database):Search
FooDB:FDB012760
Export Tariff Code:2916.15.1000
Haz-Map:View
Household Products:Search
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Formulations/Preparations:
grade: technical, purified (99+%), edible.
 
Potential Blenders and core components note
None Found
 
Potential Uses:
 antistatic agents
 emollients
 hair conditioning
 skin conditioning
 surfactants
 
Occurrence (nature, food, other):note
 ambrette seed concrete @ 0.21%
Data GC Search Trop Picture
 ambrette seed oil @ 0.50%
Data GC Search Trop Picture
 cabbage savoy cabbage
Search Trop Picture
 calamus leaf oil @ 0.02%
Data GC Search Trop Picture
 celery seed oil CO2 extract india @ 1.04%
Data GC Search Trop Picture
 champaca concrete @ 1.00%
Data GC Search Trop Picture
 cichorium intybus l. root extract @ 6.74%
Data GC Search Trop Picture
 cistus oil @ 1.0%
Data GC Search Trop Picture
 coffee roasted coffee
Search PMC Picture
 genet absolute @ 4.00%
Data GC Search Trop Picture
 parsley leaf oil @ 0.01%
Data GC Search Trop Picture
 rue seed
Search Trop Picture
 saffron
Search Trop Picture
 
Synonyms:
 emersol 310
 emersol 315
9-cis,12-cis-grape seed oil
9-cis,12-cis-linoleic acid
9Z,12Z-linoleic acid
cis-linoleic acid
cis-9,cis-12-linoleic acid
 linoleic acid pure 99%
 linolic acid
(9Z,12Z)-octadeca-9,12-dienoic acid
(9Z,12Z)-octadecadienoic acid
(9Z,12Z)-9,12-octadecadienoic acid
(Z,Z)-9,12-octadecadienoic acid
(Z)-9,12-octadecadienoic acid
9-cis,12-cis-octadecadienoic acid
9Z,12Z-octadecadienoic acid
all-cis-9,12-octadecadienoic acid
cis-9,cis-12-octadecadienoic acid
cis-delta9,12-octadecadienoic acid
cis,cis-9,12-octadecadienoic acid
 pamolyn 210 linoleic acid
 polylin 515
 telfairic acid
 unifac 6550
 

Articles:

Info:Linoleic Acid
PubMed:Effects of Enrichment with Polyunsaturated Fatty Acids (Omega-3 and Conjugated Linoleic Acid) on Consumer Liking of Beef Aged for 7 or 21 d Evaluated at Different Locations.
PubMed:Effects of acerola fruit extract on sensory and shelf-life of salted beef patties from grinds differing in fatty acid composition.
PubMed:Fatty acid composition of subcutaneous adipose tissue from entire male pigs with extremely divergent levels of boar taint compounds - An exploratory study.
PubMed:Composition and antioxidant activities of Iranian Pulicaria gnaphalodes essential oil in Soybean oil.
PubMed:Characteristic odorants from bailingu oyster mushroom (Pleurotus eryngii var. tuoliensis) and summer oyster mushroom (Pleurotus cystidiosus).
PubMed:Designer laying hen diets to improve egg fatty acid profile and maintain sensory quality.
PubMed:Fatty acid and sensory profiles of Caciocavallo cheese as affected by management system.
PubMed:Milk volatile organic compounds and fatty acid profile in cows fed timothy as hay, pasture, or silage.
PubMed:Synthesis of 9-oxononanoic acid, a precursor for biopolymers.
PubMed:Genotypic effect of ahFAD2 on fatty acid profiles in six segregating peanut (Arachis hypogaea L) populations.
PubMed:Significant influence of particular unsaturated fatty acids and pH on the volatile compounds in meat-like model systems.
PubMed:Biological activity and fatty acid composition of Caesar's mushroom.
PubMed:Blood and tissue fatty acid compositions, lipoprotein levels, performance and meat flavor of broilers fed fish oil: changes in the pre- and post-withdrawal design.
PubMed:Association of DGAT1 genotype, fatty acid composition, and concentration of copper in milk with spontaneous oxidized flavor.
PubMed:Influence of lipid content and lipoxygenase on flavor volatiles in the tomato peel and flesh.
PubMed:The chemical composition and the content of volatile oil: potential factors that can contribute to the oxidative stability of Nigella sativa L. crude oil.
PubMed:Identification of tartary buckwheat tea aroma compounds with gas chromatography-mass spectrometry.
PubMed:Characterization and stability analysis of zinc oxide nanoencapsulated conjugated linoleic acid.
PubMed:A review of fatty acid profiles and antioxidant content in grass-fed and grain-fed beef.
PubMed:Effects of feeding diets containing increasing content of corn distillers dried grains with solubles to grower-finisher pigs on growth performance, carcass composition, and pork fat quality.
PubMed:[Chemical composition of the virgin oil obtained by mechanical pressing form several grape seed varieties (Vitis vinifera L.) with emphasis on minor constituents].
PubMed:Characterization and quantification of odor-active compounds in unsaturated fatty acid/conjugated linoleic acid (UFA/CLA)-enriched butter and in conventional butter during storage and induced oxidation.
PubMed:Effects of increasing levels of dried corn distillers grains with solubles on growth performance, carcass characteristics, and meat quality of yearling heifers.
PubMed:Influence of sporophore development, damage, storage, and tissue specificity on the enzymic formation of volatiles in mushrooms (Agaricus bisporus).
PubMed:Increasing omega fatty acid content in cow's milk through diet manipulation: effect on milk flavor.
PubMed:Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
PubMed:A study of the relationships among consumer acceptance, oxidation chemical indicators, and sensory attributes in high-oleic and normal peanuts.
PubMed:Association between fatty acid compositions and genotypes of FABP4 and LXR-alpha in Japanese black cattle.
PubMed:Studies on the aroma of five fresh tomato cultivars and the precursors of cis- and trans-4,5-epoxy-(E)-2-decenals and methional.
PubMed:Influence of lipids in the generation of phenylacetaldehyde in wort-related model systems.
PubMed:The influence of diets supplemented with conjugated linoleic acid, selenium, and vitamin E, with or without animal protein, on the quality of pork from female pigs.
PubMed:Chemical properties and consumer perception of fluid milk from conventional and pasture-based production systems.
PubMed:Chemical composition of the volatile extract and antioxidant activities of the volatile and nonvolatile extracts of Egyptian corn silk (Zea mays L.).
PubMed:Mung bean lipoxygenase in the production of a C6-aldehyde. Natural green-note flavor generation via biotransformation.
PubMed:CD36 gene deletion reduces fat preference and intake but not post-oral fat conditioning in mice.
PubMed:Effects of trans-10, cis-12 conjugated linoleic acid on ovine milk fat synthesis and cheese properties.
PubMed:Cheese manufacture with milk with elevated conjugated linoleic acid levels caused by dietary manipulation.
PubMed:Effects of supplemental rumen-protected conjugated linoleic acid or corn oil on lipid content and palatability in beef cattle.
PubMed:Injection of conjugated linoleic acid into beef strip loins.
PubMed:Antioxidant property of Decalepis hamiltonii Wight & Arn.
PubMed:Descriptive flavor analysis of bacon and pork loin from lean-genotype gilts fed conjugated linoleic acid and supplemental fat.
PubMed:Study of precursors responsible for off-flavor formation during storage of potato flakes.
PubMed:Characterization of epoxydecenal isomers as potent odorants in black tea (Dimbula) infusion.
PubMed:Mapping of the loci controlling oleic and linolenic acid contents and development of fad2 and fad3 allele-specific markers in canola (Brassica napus L.).
PubMed:Lipoxygenase from banana leaf: purification and characterization of an enzyme that catalyzes linoleic acid oxygenation at the 9-position.
PubMed:The cytotoxic and genotoxic effects of conjugated trans-2-nonenal (T2N), an off-flavor compound in beer and heat processed food arising from lipid oxidation.
PubMed:Milk and cheese from cows fed calcium salts of palm and fish oil alone or in combination with soybean products.
PubMed:Conjugated linoleic acid content and organoleptic attributes of fermented milk products produced with probiotic bacteria.
PubMed:Production of gamma-lactones by the brown-rot basidiomycete Piptoporus soloniensis.
PubMed:Characterization of factors that transform linoleic acid into di- and trihydroxyoctadecenoic acids in mash.
PubMed:Effect of heated sunflower oil and dietary supplements on the composition, oxidative stability, and sensory quality of dark chicken meat.
PubMed:Chemical, physical, and sensory properties of dairy products enriched with conjugated linoleic acid.
PubMed:Consumer acceptability of conjugated linoleic acid-enriched milk and cheddar cheese from cows grazing on pasture.
PubMed:The primate amygdala: Neuronal representations of the viscosity, fat texture, temperature, grittiness and taste of foods.
PubMed:Flavor and stability of pasteurized milk with elevated levels of conjugated linoleic acid and vaccenic acid.
PubMed:Comparison of fatty acid and polar lipid contents of tubers from two potato species, Solanum tuberosum and Solanum phureja.
PubMed:Feeding encapsulated ground full-fat soybeans to increase polyunsaturated fat concentrations and effects on flavor volatiles in fresh lamb.
PubMed:Evaluation of antioxidant capacity of cereal brans.
PubMed:The effect of Lactococcus lactis starter cultures on the oxidative stability of liquid whey.
PubMed:A review of nutritional and physiological factors affecting goat milk lipid synthesis and lipolysis.
PubMed:The impact of fortification with conjugated linoleic acid (CLA) on the quality of fluid milk.
PubMed:Quality characteristics of irradiated chicken breast rolls from broilers fed different levels of conjugated linoleic acid.
PubMed:Quality characteristics of irradiated ready-to-eat breast rolls from turkeys fed conjugated linoleic acid.
PubMed:Comparison of volatile compounds in water- and oil-soluble annatto (Bixa orellana L.) extracts.
PubMed:Effect of overexpression of fatty acid 9-hydroperoxide lyase in tomatoes (Lycopersicon esculentum Mill.).
PubMed:Composition and flavor of milk and butter from cows fed fish oil, extruded soybeans, or their combination.
PubMed:Conjugated linoleic acid improves feed efficiency, decreases subcutaneous fat, and improves certain aspects of meat quality in stress-genotype pigs.
PubMed:Effect of oleic and linoleic acids on the production of deep-fried odor in heated triolein and trilinolein.
PubMed:Composition and properties of milk and butter from cows fed fish oil.
PubMed:Mechanism of volatile compound production during storage of sunflower Oil.
PubMed:Milk fat composition of Holstein and Jersey cows with control or depleted copper status and fed whole soybeans or tallow.
PubMed:Orosensory factors in the ingestion of corn oil/sucrose mixtures by the rat.
PubMed:Antioxidant activity of selected Indian spices.
PubMed:Production of tomato flavor volatiles from a crude enzyme preparation using a hollow-fiber reactor.
PubMed:Release of deuterated nonenal during beer aging from labeled precursors synthesized in the boiling kettle.
PubMed:Developmental and growth temperature regulation of two different microsomal omega-6 desaturase genes in soybeans.
PubMed:Volatile compound content and fatty acid composition of pork as influenced by linoleic acid content of the diet.
PubMed:[Isomeric trihydroxy-octadecenoic acids in beer: Evidence for their presence and quantitative determination (author's transl)].
PubMed:Effects of treatment of whole fat soybeans or soy flour with formaldehyde to protect the polyunsaturated fatty acids from biohydrogenation in the rumen.
 
Notes:
extractives and their physically modified derivatives. vitis, vitidaceae.
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