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Details

Stereochemistry ACHIRAL
Molecular Formula C18H33O2.Na
Molecular Weight 304.4432
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SODIUM OLEATE

SMILES

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

InChI

InChIKey=BCKXLBQYZLBQEK-KVVVOXFISA-M
InChI=1S/C18H34O2.Na/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);/q;+1/p-1/b10-9-;

HIDE SMILES / InChI

Molecular Formula C18H33O2
Molecular Weight 281.4534
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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
Fatty acids and derivatives as antimicrobial agents.
1972 Jul
Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage.
1996 Nov
Effects of beta-adrenoceptor subtype stimulation on obese gene messenger ribonucleic acid and on leptin secretion in mouse brown adipocytes differentiated in culture.
1997 Feb
Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat.
1998
[Changes of thromboxane A2 receptors and their mRNA expression and effects of their antagonist phenol red in the lung of acute lung injury of rats].
1998 Jan
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.
2000 Mar
Long-chain fatty acids regulate liver carnitine palmitoyltransferase I gene (L-CPT I) expression through a peroxisome-proliferator-activated receptor alpha (PPARalpha)-independent pathway.
2001 Feb 15
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates.
2001 Jan 15
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.
2001 Jan-Feb
Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents.
2001 Jul
Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane.
2001 Jun
Enhanced GLUT2 gene expression in an oleic acid-induced in vitro fatty liver model.
2002 Jun
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
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.
2003 Feb 7
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
Effects of rosiglitazone and oleic acid on UCP-3 expression in L6 myotubes.
2003 Mar
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
2003 Mar 13
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.
2003 Mar 28
Characterization of a heart-specific fatty acid transport protein.
2003 May 2
Glucosamine-induced endoplasmic reticulum stress promotes ApoB100 degradation: evidence for Grp78-mediated targeting to proteasomal degradation.
2005 Mar
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
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
Methotrexate-induced alterations in beta-oxidation correlate with cognitive abilities in children with acute lymphoblastic leukemia.
2008 Apr
Regulation of fat-stimulated neurotensin secretion in healthy subjects.
2008 May
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
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
Monascin and ankaflavin act as natural AMPK activators with PPARα agonist activity to down-regulate nonalcoholic steatohepatitis in high-fat diet-fed C57BL/6 mice.
2014 Feb
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 Mon Mar 31 17:34:30 GMT 2025
Edited
by admin
on Mon Mar 31 17:34:30 GMT 2025
Record UNII
399SL044HN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLEIC ACID SODIUM SALT
MI  
Preferred Name English
SODIUM OLEATE
HSDB   INCI   MART.   WHO-DD  
INCI  
Official Name English
9-OCTADECENOIC ACID (Z)-, SODIUM SALT
Common Name English
E-470(II)OLEIC ACID, SODIUM SALT
Common Name English
SODIUM OLEATE [HSDB]
Common Name English
Sodium oleate [WHO-DD]
Common Name English
SODIUM OLEATE [MART.]
Common Name English
INS-470(II)OLEIC ACID, SODIUM SALT
Common Name English
OLEATE SODIUM
GREEN BOOK  
Systematic Name English
INS NO.470(II)OLEIC ACID, SODIUM SALT
Common Name English
OLEATE SODIUM [GREEN BOOK]
Common Name English
SODIUM 9-OCTADECENOATE, (Z)-
Common Name English
OLEIC ACID SODIUM SALT [MI]
Common Name English
Classification Tree Code System Code
CODEX ALIMENTARIUS (GSFA) INS-470(II)
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
NCI_THESAURUS C737
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
CFR 21 CFR 522.1610
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
CFR 21 CFR 186.1770
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
EPA PESTICIDE CODE 31704
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
JECFA EVALUATION INS-470(II)
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
Code System Code Type Description
HSDB
758
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
EPA CompTox
DTXSID7021077
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
CAS
143-19-1
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
SMS_ID
100000078138
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
NCI_THESAURUS
C84162
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
DRUG BANK
DBSALT001653
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-591-0
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
PUBCHEM
23665730
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
MESH
C013173
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
FDA UNII
399SL044HN
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
MERCK INDEX
m8191
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY Merck Index
EVMPD
SUB15309MIG
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
DAILYMED
399SL044HN
Created by admin on Mon Mar 31 17:34:30 GMT 2025 , Edited by admin on Mon Mar 31 17:34:30 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE