ELAIDIC ACID

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ACHIRAL
Molecular Formula	C18H34O2
Molecular Weight	282.4614
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCC\C=C\CCCCCCCC(O)=O

InChI

InChIKey=ZQPPMHVWECSIRJ-MDZDMXLPSA-N

InChI=1S/C18H34O2/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)/b10-9+

HIDE SMILES / InChI

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

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
The interplay between hepatic stellate cells and hepatocytes in an in vitro model of NASH.	2015-10	26187275
Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets.	2015-09-18	26240151
Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal.	2014-12-05	25451573
Structure-dependent binding and activation of perfluorinated compounds on human peroxisome proliferator-activated receptor γ.	2014-09-15	24998974
PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells.	2014-04-01	24534255
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.	2014-02	24275089
Extra virgin olive oil potentiates the effects of aromatase inhibitors via glutathione depletion in estrogen receptor-positive human breast cancer (MCF-7) cells.	2013-12	24161488
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.	2013-08	23603006
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.	2013-07-05	23619606
Increased autoimmune responses against auto-epitopes modified by oxidative and nitrosative damage in depression: implications for the pathways to chronic depression and neuroprogression.	2013-07	22898471
Sophocarpine alleviates hepatocyte steatosis through activating AMPK signaling pathway.	2013-04	23395669
Gustducin couples fatty acid receptors to GLP-1 release in colon.	2013-03-15	23341498
Quercetin ameliorate insulin resistance and up-regulates cellular antioxidants during oleic acid induced hepatic steatosis in HepG2 cells.	2013-03	23348005
Changes in mitochondrial carriers exhibit stress-specific signatures in INS-1Eβ-cells exposed to glucose versus fatty acids.	2013	24349266
New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors.	2012-11	22859314
Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line.	2012-10-15	22925809
Oleic acid decreases BCRP mediated efflux of mitoxantrone in Caco-2 cell monolayers.	2012-10	22819932
Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells.	2012-09	22683933
Differential signaling by splice variants of the human free fatty acid receptor GPR120.	2012-05	22282525
PKC activation by resveratrol derivatives with unsaturated aliphatic chain.	2012	23285216
Activation of group IVC phospholipase A(2) by polycyclic aromatic hydrocarbons induces apoptosis of human coronary artery endothelial cells.	2011-06	21132278
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.	2010-08	20541177
Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion.	2010-02	19837920
Glucosamine-induced endoplasmic reticulum stress attenuates apolipoprotein B100 synthesis via PERK signaling.	2009-09	19383982
Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus.	2008-09	18559427
Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids.	2008-07	18565938
[Effects of recruitment maneuvers in prone position for pulmonary or extra-pulmonary acute respiratory distress syndrome on hemodynamics in dog].	2008-06	18549715
PPARalpha-mediated effects of dietary lipids on intestinal barrier gene expression.	2008-05-19	18489776
Regulation of fat-stimulated neurotensin secretion in healthy subjects.	2008-05	18303078
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine.	2008-05	18356535
Methotrexate-induced alterations in beta-oxidation correlate with cognitive abilities in children with acute lymphoblastic leukemia.	2008-04	18398226
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.	2008-01	18154422
Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men.	2007-04	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.	2007-02	17237316
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.	2000-03	10771080
Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat.	1998	9872509
Effects of beta-adrenoceptor subtype stimulation on obese gene messenger ribonucleic acid and on leptin secretion in mouse brown adipocytes differentiated in culture.	1997-02	9002984
Fatty acid composition of liver total lipids in alcoholic patients with and without liver damage.	1996-11	8947319
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.	1995-12-01	8536680
Gender differences in regional fatty acid metabolism before and after meal ingestion.	1995-11	7593616
Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein.	1994-11-04	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.	1994-09-30	7929039
Physiology and pathophysiology of organic acids in cerebrospinal fluid.	1993	8412012
Hypothalamic modulation of growth hormone secretion in the rhesus monkey: evidence from intracerebroventricular infusions of glucose, free fatty acid, and ketone bodies.	1991-10	1890151
Induction of fatty acid binding protein by peroxisome proliferators in primary hepatocyte cultures and its relationship to the induction of peroxisomal beta-oxidation.	1990-04-23	2328261
Effects of acute lung injury and anesthesia on left ventricular mechanics.	1986-12	3789173
Effects of hydralazine on cardiopulmonary function in canine low-pressure pulmonary edema.	1983-09	6881582
Effect of sodium nitroprusside on cardiovascular function and pulmonary shunt in canine oleic acid pulmonary edema.	1981-11	7294408
Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses.	1980-12	7235682
Fatty acids and derivatives as antimicrobial agents.	1972-07	4670656

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 20:20:25 GMT 2025` Edited by `admin` on `Mon Mar 31 20:20:25 GMT 2025`
Record UNII	4837010H8C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-26988

Preferred Name

English

ELAIDIC ACID

Systematic Name

English

TRANS-9-OCTADECENOIC ACID

Systematic Name

English

9-OCTADECENOIC ACID, (9E)-

Common Name

English

TRANS-.DELTA.9-OCTADECENOIC ACID

Common Name

English

9-OCTADECENOIC ACID, (E)-

Common Name

English

TRANS-OLEIC ACID

Systematic Name

English

ELAIDIC ACID [MI]

Common Name

English

TRANS-ELAIDIC ACID

Systematic Name

English

(9E)-OCTADECENOIC ACID

Common Name

English

9-TRANS-OLEIC ACID

Systematic Name

English

(E)-9-OCTADECENOIC ACID

Systematic Name

English

(E)-OLEIC ACID

Systematic Name

English

C18:1 N-9T

Common Name

English

9-TRANS-OCTADECENOIC ACID

Common Name

English

ELAIDINIC ACID

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68405