(E)-oleic acid

(E)-9-octadecenoic acid

CAS: 112-79-8 C18 H34 O2 MW: 282.46738000

Identification

Name(E)-oleic acid
IUPAC(E)-octadec-9-enoic acid
CAS Number112-79-8
EINECS204-006-6
FDA UNII4837010H8C
Molecular FormulaC18 H34 O2
Molecular Weight282.46738000
MDL NumberMFCD00063954
Nikkaji NumberJ10.103F
Beilstein1726543
XlogP36.50 (est)

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 45.00 °C. @ 760.00 mm Hg
Boiling Point 360.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure 5.460000 mmHg @ 25.00 °C. (est)
Flash Point > 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w) 7.698 (est)
Soluble in water, 0.01151 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityintravenous-mouse LD50 100 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00371']

Safety in Use

Categorynatural substances and extractives
Recommendation for (E)-oleic acid usage levels up tonot for fragrance use.
Recommendation for (E)-oleic acid flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

pomegranate pericarp

Synonyms

(E)- elaidic acid trans- elaidic acid (9E)- octadec-9-enoic acid (E)- octadec-9-enoic acid trans- octadec-9-enoic acid (9E)- octadecenoic acid (9E)-9- octadecenoic acid (E)-9- octadecenoic acid 9-trans- octadecenoic acid trans-9- octadecenoic acid 9- octadecenoic acid, (9E)- 9- octadecenoic acid, (E)- trans- oleic acid PubMed: Evaluation of the Impact of Ruminant trans Fatty Acids on Human Health: Important Aspects to Consider. PubMed: Effects of elaidic acid, a predominant industrial trans fatty acid, on bacterial growth and cell surface hydrophobicity of lactobacilli. PubMed: Elaidic, vaccenic, and rumenic acid status during pregnancy: association with maternal plasmatic LC-PUFAs and atopic manifestations in infants. PubMed: Study of the surfactant properties of aqueous stream from the corn milling industry. PubMed: Elaidic acid (EA) generates dysfunctional high-density lipoproteins and consumption of EA exacerbates hyperlipidemia and fatty liver change in zebrafish. PubMed: The trans fatty acids content of selected foods in Malaysia. PubMed: Optimization of extraction conditions and fatty acid characterization of Lactobacillus pentosus cell-bound biosurfactant/bioemulsifier. PubMed: Enhanced production of biomass and lipids by supplying CO2 in marine microalga Dunaliella sp. PubMed: Lipid rafts and Fas/FasL pathway may involve in elaidic acid-induced apoptosis of human umbilical vein endothelial cells. PubMed: Validation of a short, qualitative food frequency questionnaire in French adults participating in the MONA LISA-NUT study 2005-2007. PubMed: Mechanism of formation of trans fatty acids under heating conditions in triolein. PubMed: The trans fatty acid content in human milk and its association with maternal diet among lactating mothers in Malaysia. PubMed: Fatty acid analysis of Iranian junk food, dairy, and bakery products: Special attention to trans-fats. PubMed: Prediabetic changes in gene expression induced by aspartame and monosodium glutamate in Trans fat-fed C57Bl/6 J mice. PubMed: Trans fatty acids in a range of UK processed foods. PubMed: Linolelaidic acid induces a stronger proliferative effect on human umbilical vein smooth muscle cells compared to elaidic acid. PubMed: High-throughput FTIR spectroscopy of intact HepG2 cells reveals additive and non-additive effects of individual fatty acids when given as mixtures. PubMed: [Terahertz spectroscopic investigation of elaidic acid]. PubMed: Trans fatty acid isomers and the trans-9/trans-11 index in fat containing foods. PubMed: Ecological-level associations between highly processed food intakes and plasma phospholipid elaidic acid concentrations: results from a cross-sectional study within the European prospective investigation into cancer and nutrition (EPIC). PubMed: Fatty acid composition in preterm and term breast milk. PubMed: Caspase pathway of elaidic acid (9t-C18:1)-induced apoptosis in human umbilical vein endothelial cells. PubMed: NMR-based metabolomics reveals that conjugated double bond content and lipid storage efficiency in HepG2 cells are affected by fatty acid cis/trans configuration and chain length. PubMed: Determination of elaidic and vaccenic acids in foods using GC×GC-FID and GC×GC-TOFMS. PubMed: Monitoring cellular responses upon fatty acid exposure by Fourier transform infrared spectroscopy and Raman spectroscopy. PubMed: Distinct effects of oleic acid and its trans-isomer elaidic acid on the expression of myokines and adipokines in cell models. PubMed: Free fatty acids profile of the fetal brain and the plasma, liver, brain and kidneys of pregnant rats treated with sodium arsenite at mid-organogenesis. PubMed: Acute and chronic effects of dietary fatty acids on cholecystokinin expression, storage and secretion in enteroendocrine STC-1 cells. PubMed: Effect of Sargassum thunbergii on ROS mediated oxidative damage and identification of polyunsaturated fatty acid components. PubMed: Characterization of non-endcapped polymeric ODS column for the separation of triacylglycerol positional isomers. PubMed: Total trans fatty acid analysis in spreadable cheese by capillary zone electrophoresis. PubMed: Dietary vaccenic acid has antiatherogenic effects in LDLr-/- mice. PubMed: Evaluation of fatty acid content of some Iranian fast foods with emphasis on trans fatty acids. PubMed: Correlation of erythrocyte fatty acid composition and dietary intakes with markers of atherosclerosis in patients with myocardial infarction. PubMed: Metabolic implications of dietary trans-fatty acids. PubMed: Plasma phospholipid fatty acid profiles and their association with food intakes: results from a cross-sectional study within the European Prospective Investigation into Cancer and Nutrition. PubMed: Association between serum trans-monounsaturated fatty acids and breast cancer risk in the E3N-EPIC Study. PubMed: Structure-effect relation of C18 long-chain fatty acids in the reduction of body weight in rats. PubMed: Phosphatidylcholine and sphingomyelin containing an elaidoyl fatty acid can form cholesterol-rich lateral domains in bilayer membranes. PubMed: Activation of caspase 3 in HepG2 cells by elaidic acid (t18:1). PubMed: Trans fatty acids induce apoptosis in human endothelial cells. PubMed: Influence of diet on atherogenic risk in children with renal transplants. PubMed: Ethanol-mediated variations in cellular fatty acid composition and protein profiles of two genotypically different strains of Escherichia coli O157:H7. PubMed: Exchanging partially hydrogenated fat for palmitic acid in the diet increases LDL-cholesterol and endogenous cholesterol synthesis in normocholesterolemic women. PubMed: In vitro test for the effectiveness of antioxidants as inhibitors of thiyl radical-induced reactions with unsaturated fatty acids. PubMed: Effect of 6 dietary fatty acids on the postprandial lipid profile, plasma fatty acids, lipoprotein lipase, and cholesterol ester transfer activities in healthy young men. PubMed: Follow-up of the delta4 to delta16 trans-18:1 isomer profile and content in French processed foods containing partially hydrogenated vegetable oils during the period 1995-1999. Analytical and nutritional implications. PubMed: Lipids and immunology. PubMed: Fatty acids modulate lecithin:cholesterol acyltransferase secretion independently of effects on triglyceride secretion in primary rat hepatocytes. 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: Trans (elaidic) fatty acids adversely affect the lipoprotein profile relative to specific saturated fatty acids in humans. PubMed: Dietary fatty acids and progression of coronary artery disease in men. PubMed: Platelet trans fatty acids in relation to angiographically assessed coronary artery disease. PubMed: Dietary saturated and trans fatty acids and cholesterol and 25-year mortality from coronary heart disease: the Seven Countries Study. PubMed: Trans fatty acids: a cause for concern? PubMed: Effects of stearic acid and trans fatty acids versus linoleic acid on blood pressure in normotensive women and men. PubMed: Trans monounsaturated fatty acids in nutrition and their impact on serum lipoprotein levels in man. PubMed: A comparative study of micronucleus frequency in peripheral blood lymphocytes of human subjects given dietary cis, trans and saturated fat. PubMed: Trans fatty acids may impair biosynthesis of long-chain polyunsaturates and growth in man. PubMed: [Is nutritional intervention influencing lipid allowances beneficial?]. PubMed: Trans unsaturated fatty acids in natural products and processed foods. PubMed: Chemical and biological properties related to toxicity of heated fats. PubMed: Effects of dietary trans acids on the biosynthesis of arachidonic acid in rat liver microsomes.