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Details

Stereochemistry ACHIRAL
Molecular Formula C18H34O2
Molecular Weight 282.462
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OLEIC ACID

SMILES

CCCCCCCC/C(/[H])=C(/[H])\CCCCCCCC(=O)O

InChI

InChIKey=ZQPPMHVWECSIRJ-KTKRTIGZSA-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
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

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
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
Hypothalamic modulation of growth hormone secretion in the rhesus monkey: evidence from intracerebroventricular infusions of glucose, free fatty acid, and ketone bodies.
1991 Oct
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein.
1994 Nov 4
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
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.
1995 Dec 1
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
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
Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation.
2005 Dec
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
Fatty acid sensor for low-cost lifetime-assisted ratiometric sensing using a fluorescent fatty acid binding protein.
2005 Oct 1
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?
2006 Aug
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.
2006 May
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
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.
2008 Jan
Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids.
2008 Jul
[Effects of recruitment maneuvers in prone position for pulmonary or extra-pulmonary acute respiratory distress syndrome on hemodynamics in dog].
2008 Jun
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine.
2008 May
PPARalpha-mediated effects of dietary lipids on intestinal barrier gene expression.
2008 May 19
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
New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors.
2012 Nov
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
Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells.
2012 Sep
Changes in mitochondrial carriers exhibit stress-specific signatures in INS-1Eβ-cells exposed to glucose versus fatty acids.
2013
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
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
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
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.
2013 Jul 5
Quercetin ameliorate insulin resistance and up-regulates cellular antioxidants during oleic acid induced hepatic steatosis in HepG2 cells.
2013 Mar
Gustducin couples fatty acid receptors to GLP-1 release in colon.
2013 Mar 15
PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells.
2014 Apr 1
Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal.
2014 Dec 5
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
Structure-dependent binding and activation of perfluorinated compounds on human peroxisome proliferator-activated receptor γ.
2014 Sep 15
The interplay between hepatic stellate cells and hepatocytes in an in vitro model of NASH.
2015 Oct
Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets.
2015 Sep 18
Patents

Sample Use Guides

Rats were gavaged with oleic acid FFA (500 mg/10 mL/kg)
Route of Administration: Oral
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
OLEIC ACID
EP   FCC   FHFI   HSDB   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
OLEIC ACID [EP MONOGRAPH]
Common Name English
CIS-9-OCTADECENOIC ACID
Systematic Name English
9-OCTADECENOIC ACID (9Z)-
Systematic Name English
OLEIC ACID (CONSTITUENT OF EVENING PRIMROSE OIL) [DSC]
Common Name English
OLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC]
Common Name English
OLEIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]
Common Name English
OLEIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
VOPCOLENE 27
Common Name English
WECOLINE OO
Common Name English
OLEIC ACID [MART.]
Common Name English
OLEIC ACID [MI]
Common Name English
OLEIC ACID [II]
Common Name English
OLEIC ACID (C18:1) (CONSTITUENT OF KRILL OIL) [DSC]
Common Name English
OLEIC ACID (CONSTITUENT OF FLAX SEED OIL) [DSC]
Common Name English
PRIOLENE 6936
Common Name English
OLEIC ACID [HSDB]
Common Name English
OLEIC ACID [FHFI]
Common Name English
OLEATE
Systematic Name English
18:1(N-9)
Code English
FEMA NO. 2815
Code English
9-OCTADECENOIC ACID, (Z)-
Common Name English
OLEIC ACID [INCI]
Common Name English
NSC-9856
Code English
OLEIC ACID [VANDF]
Common Name English
OLEIC ACID [USP-RS]
Common Name English
9Z-OCTADECENOIC ACID
Common Name English
OLEIC ACID [WHO-DD]
Common Name English
OLEIC ACID [FCC]
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 31702
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LOINC 2673-2
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CFR 21 CFR 172.210
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LOINC 35166-8
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LOINC 75102-4
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CFR 21 CFR 172.862
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CFR 21 CFR 172.860
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LOINC 47713-3
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LOINC 27108-0
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DSLD 262 (Number of products:639)
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JECFA EVALUATION OLEIC ACID
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LOINC 74620-6
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LOINC 74621-4
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Code System Code Type Description
NCI_THESAURUS
C68405
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PRIMARY
FDA UNII
2UMI9U37CP
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
USP_CATALOG
1478130
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY USP-RS
ChEMBL
CHEMBL8659
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
DRUG CENTRAL
3400
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
MESH
D019301
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
HSDB
1240
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
PUBCHEM
445639
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-007-1
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PRIMARY
RXCUI
70616
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ALTERNATIVE
RXCUI
7631
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
EPA CompTox
112-80-1
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
CAS
112-80-1
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
WIKIPEDIA
OLEIC ACID
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
RXCUI
32559
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
DRUG BANK
DB04224
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
EVMPD
SUB12542MIG
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY
MERCK INDEX
M8191
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
PRIMARY Merck Index