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

Description
Sources: http://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/25430075https://www.ncbi.nlm.nih.gov/pubmed/8018112

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

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 8297	61.31 µM [IC50]
Anandamide amidohydrolase 26 Target ID: CHEMBL3455 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24191036	Inhibitor 8297
SiHa 5 Target ID: CHEMBL612542 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25430075	Inhibitor 8297
Fatty acid binding protein adipocyte 12 Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17502136	Inhibitor 8297	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 1430

Conditions

Condition	Modality	Highest Phase	Product
Atherosclerosis 74 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25528432 https://www.ncbi.nlm.nih.gov/pubmed/9034243	Primary	Phase I 428	Unknown Approved Use Unknown
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11023139 https://www.ncbi.nlm.nih.gov/pubmed/23238293	Primary	Phase I 428	Unknown Approved Use Unknown
Obesity 203 Sources: https://clinicaltrials.gov/ct2/show/NCT00059254 https://www.ncbi.nlm.nih.gov/pubmed/24829493	Primary	Phase I 428	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: https://clinicaltrials.gov/ct2/show/NCT01661764 https://www.ncbi.nlm.nih.gov/pubmed/21956128	Preventing	Phase II 1132	Unknown Approved Use Unknown
Unknown 2578

PubMed

Title	Date	PubMed
Fatty acids and derivatives as antimicrobial agents.	1972 Jul	4670656
Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses.	1980 Dec	7235682
Effect of sodium nitroprusside on cardiovascular function and pulmonary shunt in canine oleic acid pulmonary edema.	1981 Nov	7294408
Effects of hydralazine on cardiopulmonary function in canine low-pressure pulmonary edema.	1983 Sep	6881582
Effects of acute lung injury and anesthesia on left ventricular mechanics.	1986 Dec	3789173
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	2328261
Physiology and pathophysiology of organic acids in cerebrospinal fluid.	1993	8412012
Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein.	1994 Nov 4	7954810
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	7929039
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.	1995 Dec 1	8536680
Gender differences in regional fatty acid metabolism before and after meal ingestion.	1995 Nov	7593616
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
Fat mobilization in adipose tissue is promoted by adipose triglyceride lipase.	2004 Nov 19	15550674
COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers.	2004 Sep-Oct	15602154
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.	2005 Jan	15619630
Glucosamine-induced endoplasmic reticulum stress promotes ApoB100 degradation: evidence for Grp78-mediated targeting to proteasomal degradation.	2005 Mar	15618547
Fatty acids and expression of adipokines.	2005 May 30	15949695
The repression of E2F-1 is critical for the activity of Minerval against cancer.	2005 Oct	16027227
Fatty acid sensor for low-cost lifetime-assisted ratiometric sensing using a fluorescent fatty acid binding protein.	2005 Oct 1	16137630
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.	2005 Oct 28	16118212
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.	2006 May	16489205
Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men.	2007 Apr	17138722
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.	2008 Jan	18154422
Regulation of fat-stimulated neurotensin secretion in healthy subjects.	2008 May	18303078
Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus.	2008 Sep	18559427
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
Activation of group IVC phospholipase A(2) by polycyclic aromatic hydrocarbons induces apoptosis of human coronary artery endothelial cells.	2011 Jun	21132278
PKC activation by resveratrol derivatives with unsaturated aliphatic chain.	2012	23285216
Differential signaling by splice variants of the human free fatty acid receptor GPR120.	2012 May	22282525
New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors.	2012 Nov	22859314
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
Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells.	2012 Sep	22683933
Changes in mitochondrial carriers exhibit stress-specific signatures in INS-1Eβ-cells exposed to glucose versus fatty acids.	2013	24349266
Sophocarpine alleviates hepatocyte steatosis through activating AMPK signaling pathway.	2013 Apr	23395669
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	23603006
Extra virgin olive oil potentiates the effects of aromatase inhibitors via glutathione depletion in estrogen receptor-positive human breast cancer (MCF-7) cells.	2013 Dec	24161488
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	22898471
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.	2013 Jul 5	23619606
Quercetin ameliorate insulin resistance and up-regulates cellular antioxidants during oleic acid induced hepatic steatosis in HepG2 cells.	2013 Mar	23348005
Gustducin couples fatty acid receptors to GLP-1 release in colon.	2013 Mar 15	23341498
PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells.	2014 Apr 1	24534255
Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal.	2014 Dec 5	25451573
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
Structure-dependent binding and activation of perfluorinated compounds on human peroxisome proliferator-activated receptor γ.	2014 Sep 15	24998974
The interplay between hepatic stellate cells and hepatocytes in an in vitro model of NASH.	2015 Oct	26187275
Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets.	2015 Sep 18	26240151

Patents

Sample Use Guides

In Vivo Use Guide

Rats were gavaged with oleic acid FFA (500 mg/10 mL/kg)

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

SODIUM OLEATE

Official Name

English

OLEIC ACID SODIUM SALT

Common 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

SODIUM OLEATE [INCI]

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)