(E)-oleic acid
(E)-9-octadecenoic acid
Identification
| Name | (E)-oleic acid |
| IUPAC | (E)-octadec-9-enoic acid |
| CAS Number | 112-79-8 |
| EINECS | 204-006-6 |
| FDA UNII | 4837010H8C |
| Molecular Formula | C18 H34 O2 |
| Molecular Weight | 282.46738000 |
| MDL Number | MFCD00063954 |
| Nikkaji Number | J10.103F |
| Beilstein | 1726543 |
| XlogP3 | 6.50 (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 SDS | View |
| Oral/Parenteral Toxicity | intravenous-mouse LD50 100 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not 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
| Category | natural substances and extractives |
| Recommendation for (E)-oleic acid usage levels up to | not for fragrance use. |
| Recommendation for (E)-oleic acid flavor usage levels up to | not for flavor use. |
Penta International Corporation
Chemistry innovation
At Penta, our products and services help businesses do business better.
Potential Uses
Natural Occurrence
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/6Â 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 GCÃGC-FID and GCÃGC-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.