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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

Oleic acid is an unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Oleic acid occurs naturally in various animal and vegetable fats and oils. It is a component of the normal human diet as a part of animal fats and vegetable oils. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil. Oleic acid has being shown to have a potential anticancer activity.

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
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
Effects of acute lung injury and anesthesia on left ventricular mechanics.
1986 Dec
Induction of fatty acid binding protein by peroxisome proliferators in primary hepatocyte cultures and its relationship to the induction of peroxisomal beta-oxidation.
1990 Apr 23
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB.
1994 Sep 30
Gender differences in regional fatty acid metabolism before and after meal ingestion.
1995 Nov
Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage.
1996 Nov
Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man.
2000
Down-regulation of uncoupling protein-3 and -2 by thiazolidinediones in C2C12 myotubes.
2000 Oct 27
The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells.
2001 Jan
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.
2001 Jan-Feb
Regulation of uncoupling protein-2 mRNA in L6 myotubules: II: Thyroid hormone amplifies stimulation of uncoupling protein-2 gene by thiazolidinediones and other peroxisome proliferator-activated receptor ligands in L6 myotubules: evidence for a priming effect.
2002 Nov
Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability.
2003 Aug
Endogenous phospholipase D2 localizes to the plasma membrane of RBL-2H3 mast cells and can be distinguished from ADP ribosylation factor-stimulated phospholipase D1 activity by its specific sensitivity to oleic acid.
2003 Jan 15
Exchanging carbohydrates for monounsaturated fats in energy-restricted diets: effects on metabolic profile and other cardiovascular risk factors.
2003 Jun
Characterization of a heart-specific fatty acid transport protein.
2003 May 2
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers.
2004 Sep-Oct
Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation.
2005 Dec
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005 Jan
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
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.
2005 Oct 28
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?
2006 Aug
Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells.
2006 Aug
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
[Effects of recruitment maneuvers in prone position for pulmonary or extra-pulmonary acute respiratory distress syndrome on hemodynamics in dog].
2008 Jun
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
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
Sophocarpine alleviates hepatocyte steatosis through activating AMPK signaling pathway.
2013 Apr
Amelioration by chicory seed extract of diabetes- and oleic acid-induced non-alcoholic fatty liver disease (NAFLD)/non-alcoholic steatohepatitis (NASH) via modulation of PPARα and SREBP-1.
2013 Aug
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
Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal.
2014 Dec 5
Patents

Sample Use Guides

diet, containing 15% energy as fat from dairy products, meat, bread and cereals, was supplemented with oleic or elaidic acid
Route of Administration: Oral
In Vitro Use Guide
It was studied the impact of both cis and trans forms of C 18:1 fatty acids. It was found that cis and trans vaccenic acid (cis and trans C 18:1 delta11), as well as oleic acid (cis C 18:1 delta9) and elaidic acid (trans 18:1 delta9), caused a dose-dependent increase in glucose (16.7 mmol/L)-stimulated insulin secretion during static islet incubations. The maximal stimulatory effect for cis and trans vaccenic acid and for oleic and elaidic acid was observed at concentrations of 2.0 and 3.0 mmol/L, respectively. The trans isomers, trans vaccenic and elaidic acid, elicited a higher maximal insulin output than the respective cis isomers, cis vaccenic and oleic acid. In the presence of another insulin secretagogue, L-leucine, trans vaccenic but not elaidic acid caused a higher response than their cis isomeric fatty acids.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:02:01 UTC 2023
Edited
by admin
on Thu Jul 06 02:02:01 UTC 2023
Record UNII
EH7L6J9LHN
Record Status Validated (UNII)
Record Version
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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 Thu Jul 06 02:02:01 UTC 2023 , Edited by admin on Thu Jul 06 02:02:01 UTC 2023
Code System Code Type Description
FDA UNII
EH7L6J9LHN
Created by admin on Thu Jul 06 02:02:01 UTC 2023 , Edited by admin on Thu Jul 06 02:02:01 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-873-1
Created by admin on Thu Jul 06 02:02:01 UTC 2023 , Edited by admin on Thu Jul 06 02:02:01 UTC 2023
PRIMARY
PUBCHEM
6435897
Created by admin on Thu Jul 06 02:02:01 UTC 2023 , Edited by admin on Thu Jul 06 02:02:01 UTC 2023
PRIMARY
CAS
544-60-5
Created by admin on Thu Jul 06 02:02:01 UTC 2023 , Edited by admin on Thu Jul 06 02:02:01 UTC 2023
PRIMARY
EPA CompTox
DTXSID50878372
Created by admin on Thu Jul 06 02:02:01 UTC 2023 , Edited by admin on Thu Jul 06 02:02:01 UTC 2023
PRIMARY
MERCK INDEX
M1802
Created by admin on Thu Jul 06 02:02:01 UTC 2023 , Edited by admin on Thu Jul 06 02:02:01 UTC 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE