SODIUM OLEATE

US Previously Marketed

First marketed in 1921

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8018112http://www.tuscany-diet.net/lipids/list-of-fatty-acids/oleic/ | https://www.ncbi.nlm.nih.gov/pubmed/18772370 | https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.860 | https://www.ncbi.nlm.nih.gov/pubmed/25430075

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Beta-secretase 1 21 Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24548007	Inhibitor 8504	61.31 µM [IC50]
Anandamide amidohydrolase 27 Target ID: CHEMBL3455 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24191036	Inhibitor 8504
SiHa 5 Target ID: CHEMBL612542 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25430075	Inhibitor 8504
Fatty acid binding protein adipocyte 12 Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17502136	Inhibitor 8504	185.0 nM [Ki]
Cholesteryl ester transfer protein 15 Target ID: P11597 Gene ID: 1071.0 Gene Symbol: CETP Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8018112	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Atherosclerosis 76 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25528432 https://www.ncbi.nlm.nih.gov/pubmed/9034243	Primary	Phase I 438	Unknown Approved Use Unknown
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11023139 https://www.ncbi.nlm.nih.gov/pubmed/23238293	Primary	Phase I 438	Unknown Approved Use Unknown
Obesity 206 Sources: https://clinicaltrials.gov/ct2/show/NCT00059254 https://www.ncbi.nlm.nih.gov/pubmed/24829493	Primary	Phase I 438	Unknown Approved Use Unknown
Colorectal cancer 102 Sources: https://clinicaltrials.gov/ct2/show/NCT01661764 https://www.ncbi.nlm.nih.gov/pubmed/21956128	Preventing	Phase II 1147	Unknown Approved Use Unknown
Unknown 2596

PubMed

Title	Date	PubMed
Fatty acids and derivatives as antimicrobial agents.	1972 Jul	4670656
Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage.	1996 Nov	8947319
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	9002984
Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat.	1998	9872509
[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	11263294
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.	2000 Mar	10771080
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	11171094
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates.	2001 Jan 15	11341955
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.	2001 Jan-Feb	11347965
Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents.	2001 Jul	11453902
Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane.	2001 Jun	11428654
Enhanced GLUT2 gene expression in an oleic acid-induced in vitro fatty liver model.	2002 Jun	12048068
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	12588052
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.	2003 Feb 7	12565875
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	12374567
Effects of rosiglitazone and oleic acid on UCP-3 expression in L6 myotubes.	2003 Mar	12630940
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.	2003 Mar 13	12629551
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.	2003 Mar 28	12496284
Characterization of a heart-specific fatty acid transport protein.	2003 May 2	12556534
Glucosamine-induced endoplasmic reticulum stress promotes ApoB100 degradation: evidence for Grp78-mediated targeting to proteasomal degradation.	2005 Mar	15618547
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?	2006 Aug	16895544
Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells.	2006 Aug	16837928
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	16731579
Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men.	2007 Apr	17138722
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	17237316
Methotrexate-induced alterations in beta-oxidation correlate with cognitive abilities in children with acute lymphoblastic leukemia.	2008 Apr	18398226
Regulation of fat-stimulated neurotensin secretion in healthy subjects.	2008 May	18303078
Glucosamine-induced endoplasmic reticulum stress attenuates apolipoprotein B100 synthesis via PERK signaling.	2009 Sep	19383982
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.	2010 Aug	20541177
Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion.	2010 Feb	19837920
Oleic acid decreases BCRP mediated efflux of mitoxantrone in Caco-2 cell monolayers.	2012 Oct	22819932
Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line.	2012 Oct 15	22925809
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	24275089

Patents

Sample Use Guides

In Vivo Use Guide

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

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Name

Type

Language

OLEIC ACID SODIUM SALT

Preferred Name

English

SODIUM OLEATE

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

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)