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Details

Stereochemistry ACHIRAL
Molecular Formula C18H33O2.H4N
Molecular Weight 299.4919
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of AMMONIUM OLEATE

SMILES

[NH4+].CCCCCCCC\C=C/CCCCCCCC([O-])=O

InChI

InChIKey=WFXRJNDIBXZNJK-KVVVOXFISA-N
InChI=1S/C18H34O2.H3N/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20;/h9-10H,2-8,11-17H2,1H3,(H,19,20);1H3/b10-9-;

HIDE SMILES / InChI

Molecular Formula H3N
Molecular Weight 17.0305
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C18H34O2
Molecular Weight 282.4614
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Elaidic acid is the 9-trans isomer of oleic acid. It is a monounsaturated trans-fatty acid, which can be found in partially hydrogenated cooking oils. It was revealed, that elaidic acid inhibits HHT and HETE formation in human platelets incubated with arachidonic acid. Also was shown, that trans oleic acid increased plasma CETP activity, which increases low-density lipoprotein (LDL) cholesterol and decreases high-density lipoprotein (HDL).

CNS Activity

Curator's Comment: It was demonstrated that the 18 carbon-monocarboxylic fatty acids, linoleic acid with two cis-double bonds entered brain, whereas oleic acid, with one cis-double bond, did not enter brain. It was concluded the entry of essential fatty acids into brain is accomplished in a highly selective and discrete manner

Originator

Curator's Comment: Oleic acid was recognized in pork fat by Chevreul M.E. in 1823 while the structure was elucidated later by the works of Baruch J. (1894) and Edmed F.G. (1898); it was synthesized for the first time by Noller C.R. et al. in 1934.

Approval Year

PubMed

PubMed

TitleDatePubMed
Fatty acids and derivatives as antimicrobial agents.
1972 Jul
Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses.
1980 Dec
Effect of sodium nitroprusside on cardiovascular function and pulmonary shunt in canine oleic acid pulmonary edema.
1981 Nov
Effects of hydralazine on cardiopulmonary function in canine low-pressure pulmonary edema.
1983 Sep
Hypothalamic modulation of growth hormone secretion in the rhesus monkey: evidence from intracerebroventricular infusions of glucose, free fatty acid, and ketone bodies.
1991 Oct
Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage.
1996 Nov
Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat.
1998
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
Stearoyl-CoA desaturase 1 gene expression is necessary for fructose-mediated induction of lipogenic gene expression by sterol regulatory element-binding protein-1c-dependent and -independent mechanisms.
2004 Jun 11
Accuracy of the double indicator method for measurement of extravascular lung water depends on the type of acute lung injury.
2004 Mar
Copper ions and hypochlorite are mainly responsible for oxidative inactivation of paraoxon-hydrolyzing activity in human high density lipoprotein.
2004 Mar 7
Fat mobilization in adipose tissue is promoted by adipose triglyceride lipase.
2004 Nov 19
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
Dietary trans fatty acids and composition of human atheromatous plaques.
2004 Oct
COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers.
2004 Sep-Oct
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005 Jan
Glucosamine-induced endoplasmic reticulum stress promotes ApoB100 degradation: evidence for Grp78-mediated targeting to proteasomal degradation.
2005 Mar
Fatty acids and expression of adipokines.
2005 May 30
Effect of a sustained reduction in plasma free fatty acid concentration on intramuscular long-chain fatty Acyl-CoAs and insulin action in type 2 diabetic patients.
2005 Nov
The repression of E2F-1 is critical for the activity of Minerval against cancer.
2005 Oct
Fatty acid sensor for low-cost lifetime-assisted ratiometric sensing using a fluorescent fatty acid binding protein.
2005 Oct 1
Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha.
2006 Aug
Dual inhibition of mycobacterial fatty acid biosynthesis and degradation by 2-alkynoic acids.
2006 Mar
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.
2006 May
Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men.
2007 Apr
Intake of fish oil, oleic acid, folic acid, and vitamins B-6 and E for 1 year decreases plasma C-reactive protein and reduces coronary heart disease risk factors in male patients in a cardiac rehabilitation program.
2007 Feb
Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element.
2007 Mar
Methotrexate-induced alterations in beta-oxidation correlate with cognitive abilities in children with acute lymphoblastic leukemia.
2008 Apr
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.
2008 Jan
Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids.
2008 Jul
Regulation of fat-stimulated neurotensin secretion in healthy subjects.
2008 May
Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus.
2008 Sep
Glucosamine-induced endoplasmic reticulum stress attenuates apolipoprotein B100 synthesis via PERK signaling.
2009 Sep
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.
2010 Aug
Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion.
2010 Feb
Activation of group IVC phospholipase A(2) by polycyclic aromatic hydrocarbons induces apoptosis of human coronary artery endothelial cells.
2011 Jun
PKC activation by resveratrol derivatives with unsaturated aliphatic chain.
2012
Differential signaling by splice variants of the human free fatty acid receptor GPR120.
2012 May
New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors.
2012 Nov
Oleic acid decreases BCRP mediated efflux of mitoxantrone in Caco-2 cell monolayers.
2012 Oct
Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line.
2012 Oct 15
Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells.
2012 Sep
Changes in mitochondrial carriers exhibit stress-specific signatures in INS-1Eβ-cells exposed to glucose versus fatty acids.
2013
Sophocarpine alleviates hepatocyte steatosis through activating AMPK signaling pathway.
2013 Apr
Increased autoimmune responses against auto-epitopes modified by oxidative and nitrosative damage in depression: implications for the pathways to chronic depression and neuroprogression.
2013 Jul
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.
2013 Jul 5
PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells.
2014 Apr 1
Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal.
2014 Dec 5
The interplay between hepatic stellate cells and hepatocytes in an in vitro model of NASH.
2015 Oct
Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets.
2015 Sep 18
Patents

Sample Use Guides

Rats were gavaged with oleic acid FFA (500 mg/10 mL/kg)
Route of Administration: Oral
Oleic acid noncompetitively attenuated BACE1 activity with a half-maximal inhibitory concentration (IC₅₀) value of 61.31 uM and Ki value of 34.3 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:51:26 GMT 2023
Edited
by admin
on Fri Dec 15 18:51:26 GMT 2023
Record UNII
EH7L6J9LHN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AMMONIUM OLEATE
INCI   MI  
INCI  
Official Name English
AMMONIUM OLEATE [MI]
Common Name English
(9Z)-9-OCTADECENOIC ACID AMMONIUM SALT (1:1)
Common Name English
AMMONIUM OLEATE [INCI]
Common Name English
OLEIC ACID AMMONIUM SALT
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 31703
Created by admin on Fri Dec 15 18:51:26 GMT 2023 , Edited by admin on Fri Dec 15 18:51:26 GMT 2023
Code System Code Type Description
FDA UNII
EH7L6J9LHN
Created by admin on Fri Dec 15 18:51:26 GMT 2023 , Edited by admin on Fri Dec 15 18:51:26 GMT 2023
PRIMARY
ECHA (EC/EINECS)
208-873-1
Created by admin on Fri Dec 15 18:51:26 GMT 2023 , Edited by admin on Fri Dec 15 18:51:26 GMT 2023
PRIMARY
PUBCHEM
6435897
Created by admin on Fri Dec 15 18:51:26 GMT 2023 , Edited by admin on Fri Dec 15 18:51:26 GMT 2023
PRIMARY
CAS
544-60-5
Created by admin on Fri Dec 15 18:51:26 GMT 2023 , Edited by admin on Fri Dec 15 18:51:26 GMT 2023
PRIMARY
EPA CompTox
DTXSID50878372
Created by admin on Fri Dec 15 18:51:26 GMT 2023 , Edited by admin on Fri Dec 15 18:51:26 GMT 2023
PRIMARY
MERCK INDEX
m1802
Created by admin on Fri Dec 15 18:51:26 GMT 2023 , Edited by admin on Fri Dec 15 18:51:26 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE