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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 of Oleic acid

SMILES

CCCCCCCC\C=C/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

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

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
Effects of hydralazine on cardiopulmonary function in canine low-pressure pulmonary edema.
1983 Sep
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
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
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
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
The ligands/activators for peroxisome proliferator-activated receptor alpha (PPARalpha) and PPARgamma increase Cu2+,Zn2+-superoxide dismutase and decrease p22phox message expressions in primary endothelial cells.
2001 Jan
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
Bezafibrate attenuates the overexpression of plasminogen activator inhibitor-1 messenger RNA by a combination of mono-unsaturated fatty acid and insulin in hepG2 cells.
2001 Mar 9
Enhanced GLUT2 gene expression in an oleic acid-induced in vitro fatty liver model.
2002 Jun
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
Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme.
2003 Jun
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
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
Copper ions and hypochlorite are mainly responsible for oxidative inactivation of paraoxon-hydrolyzing activity in human high density lipoprotein.
2004 Mar 7
COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers.
2004 Sep-Oct
Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation.
2005 Dec
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005 Jan
Fatty acids and expression of adipokines.
2005 May 30
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
The repression of E2F-1 is critical for the activity of Minerval against cancer.
2005 Oct
Fatty acid sensor for low-cost lifetime-assisted ratiometric sensing using a fluorescent fatty acid binding protein.
2005 Oct 1
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.
2005 Oct 28
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
Dual inhibition of mycobacterial fatty acid biosynthesis and degradation by 2-alkynoic acids.
2006 Mar
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.
2006 May
Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men.
2007 Apr
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
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.
2008 Jan
Regulation of fat-stimulated neurotensin secretion in healthy subjects.
2008 May
Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion.
2010 Feb
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
Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line.
2012 Oct 15
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
Gustducin couples fatty acid receptors to GLP-1 release in colon.
2013 Mar 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
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:12:27 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:27 GMT 2023
Record UNII
2UMI9U37CP
Record Status Validated (UNII)
Record Version
  • Download
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
OSTEUM
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
ENDOCINE COMPONENT OLEIC ACID
Common Name English
OLEIC ACID [USP-RS]
Common Name English
Oleic acid [WHO-DD]
Common Name English
9Z-OCTADECENOIC ACID
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
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PRIMARY
ChEMBL
CHEMBL8659
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PRIMARY
DAILYMED
2UMI9U37CP
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PRIMARY
DRUG CENTRAL
3400
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PRIMARY
MESH
D019301
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PRIMARY
HSDB
1240
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PRIMARY
PUBCHEM
445639
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PRIMARY
JECFA MONOGRAPH
68
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PRIMARY
CHEBI
16196
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PRIMARY
ECHA (EC/EINECS)
204-007-1
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PRIMARY
RXCUI
70616
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ALTERNATIVE
RXCUI
7631
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PRIMARY
EPA CompTox
DTXSID1025809
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PRIMARY
CAS
112-80-1
Created by admin on Fri Dec 15 15:12:27 GMT 2023 , Edited by admin on Fri Dec 15 15:12:27 GMT 2023
PRIMARY
WIKIPEDIA
OLEIC ACID
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PRIMARY
RS_ITEM_NUM
1478130
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PRIMARY
NSC
9856
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PRIMARY
RXCUI
32559
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ALTERNATIVE
DRUG BANK
DB04224
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PRIMARY
SMS_ID
100000091945
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PRIMARY
EVMPD
SUB12542MIG
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PRIMARY
MERCK INDEX
m8191
Created by admin on Fri Dec 15 15:12:27 GMT 2023 , Edited by admin on Fri Dec 15 15:12:27 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
LIPID -> FATTY ACID
dependent on method of extraction
LIPID -> FATTY ACID
LIPID -> FATTY ACID
G Jurriens and ACJ Kroesen, J Am Oil Chem Soc, 42(9)(1965)(average value). Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
LIPID -> FATTY ACID
Values are % of weight of fatty acid composition. O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range) Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
LIPID -> FATTY ACID
Value is % of composition. Oleic safflower variety UC-1 cited by Knowles, P, Calif. Agr. 19(12),15(1965), produced 77.00% by composition.
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
MAY BE PRESENT
USP
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Compound measured as 1.60% of the composition of the steam distillate of Elymus repens rhizome as per R Boesel in Planta Medica iss:4 pg:399-400, 1989.
LIPID -> FATTY ACID
Values are % of total.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Value is % of total fatty acids. Maiti, S, et al; Handbook of Annual Oilseed Crops, OIBH, New Delhi, India(1988), pp.1987-90
LIPID -> FATTY ACID
Value is fatty acid composition (%) for US corn oil w/std. deviation of 0.90% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
LIPID -> FATTY ACID
Value is fatty acid composition (%) for international corn oil w/std. deviation of 2.5% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
LIPID -> FATTY ACID
TUNISIAN SOURCE
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY