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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
Molecular Formula C18H34O2
Molecular Weight 282.462
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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

CNS Non-penetrant
1062
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

Chevreul, M.E.
21
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

1921
1413
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7728
 61.31 µM [IC50]
Inhibitor
7728
SiHa
5
Target ID: CHEMBL612542
Inhibitor
7728
Inhibitor
7728
 185.0 nM [Ki]
Cholesteryl ester transfer protein
14
Target ID: P11597
Gene ID: 1071.0
Gene Symbol: CETP
Target Organism: Homo sapiens (Human)
Activator
1343
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
409
Unknown

Approved Use

Unknown
Primary
Phase I
409
Unknown

Approved Use

Unknown
Primary
Phase I
409
Unknown

Approved Use

Unknown
Preventing
Phase II
1101
Unknown

Approved Use

Unknown
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
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
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
Dual inhibition of mycobacterial fatty acid biosynthesis and degradation by 2-alkynoic acids.
2006 Mar
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
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

Patents

07019071
5
20030104740
5
JP1036633A
5
JP2000044411A
5
JP2000093079A
7
JP2000093080A
7
JP2000103726A
5
JP2000178208A
15
JP2000503711A
5
JP2001294538A
10
JP2002501616A
5
JP2002533379A
51
JP2004307635A
5
JP2005082715A
5
JP2008201951A
6
JP2010195782A
5
JP2010537404A
9
JP2011507590A
5
JP2011524743A
29
JP3271988B2
5
JP4690404B2
11
JP4690405B2
9
JP4690406B2
6
JP4800570B2
5
JP4814107B2
7
JP4818355B2
5
JP4838936B2
15
JPH00657282A
5
JPH01102060A
5
JPH01190362A
5
JPH01190666A
5
JPH01207131A
5
JPH01245039A
5
JPH02117944A
5
JPH02123199A
6
JPH02207740A
6
JPH02208375A
5
JPH02231701A
8
JPH02281062A
5
JPH03265693A
5
JPH03269196A
5
JPH0376797A
5
JPH04114740A
5
JPH04164979A
5
JPH0431318A
5
JPH0433985A
5
JPH046105A
5
JPH05112608A
6
JPH05171129A
5
JPH05287293A
5
JPH0567512A
5
JPH06345802A
21
JPH0641440A
5
US2705723
5
US4601856
5

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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:13:15 UTC 2021
Edited
by admin
on Fri Jun 25 21:13:15 UTC 2021
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
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
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
LOINC 2673-2
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
CFR 21 CFR 172.210
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
LOINC 35166-8
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LOINC 75102-4
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CFR 21 CFR 172.862
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
CFR 21 CFR 172.860
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
LOINC 47713-3
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
LOINC 27108-0
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
DSLD 262 (Number of products:639)
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
JECFA EVALUATION 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
LOINC 74620-6
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LOINC 74621-4
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Code System Code Type Description
NCI_THESAURUS
C68405
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
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
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
70616
Created by admin on Fri Jun 25 21:13:15 UTC 2021 , Edited by admin on Fri Jun 25 21:13:15 UTC 2021
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
Related Record Type Details
Structure of LEAD OLEATE
SALT/SOLVATE -> PARENT
COIX LACRYMA-JOBI SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
SESAME OIL
LIPID -> FATTY ACID
Value is % of total fatty acids. Goden VJ, Spensley PC; Oils and Oilseeds, TPI, London, 1971, p.151
EVENING PRIMROSE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of AMMONIUM OLEATE
SALT/SOLVATE -> PARENT
COCONUT OIL
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
Structure of THEOBROMINE MAGNESIUM OLEATE
SALT/SOLVATE -> PARENT
Structure of MERCURY OLEATE
SALT/SOLVATE -> PARENT
Structure of DIMETHYL LAURAMINE OLEATE
SALT/SOLVATE -> PARENT
Structure of FRAMYCETIN OLEATE
SALT/SOLVATE -> PARENT
Structure of ETHANOLAMINE OLEATE
SALT/SOLVATE -> PARENT
Structure of ZINC OLEATE
SALT/SOLVATE -> PARENT
Structure of FERRIC OLEATE
SALT/SOLVATE -> PARENT
CANOLA OIL
LIPID -> FATTY ACID
SAFFLOWER OIL
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.
CASTOR OIL
LIPID -> FATTY ACID
COTTONSEED OIL
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)
CANNABIS SATIVA SUBSP. INDICA TOP
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
Structure of COPPER OLEATE
SALT/SOLVATE -> PARENT
SOYBEAN OIL
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)
Structure of PHENYLMERCURIC OLEATE
SALT/SOLVATE -> PARENT
PEANUT OIL
LIPID -> FATTY ACID
Values are % of total.
FISH OIL
LIPID -> FATTY ACID
MAY BE PRESENT
USP
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PALM OIL
LIPID -> FATTY ACID
Values are % of total.
Structure of CALCIUM OLEATE
SALT/SOLVATE -> PARENT
BORAGE SEED OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of TRIETHANOLAMINE OLEATE
SALT/SOLVATE -> PARENT
RICE BRAN OIL
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
Structure of MORPHOLINE OLEATE
SALT/SOLVATE -> PARENT
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of SODIUM OLEATE
SALT/SOLVATE -> PARENT
KRILL OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of POTASSIUM OLEATE
SALT/SOLVATE -> PARENT
SUNFLOWER OIL
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
Structure of LITHIUM OLEATE
SALT/SOLVATE -> PARENT
OLIVE OIL
LIPID -> FATTY ACID
IOOC limits
ELYMUS REPENS ROOT
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.
Structure of MAGNESIUM OLEATE
SALT/SOLVATE -> PARENT
Structure of COBALTOUS OLEATE
SALT/SOLVATE -> PARENT
AVOCADO OIL
LIPID -> FATTY ACID
dependent on method of extraction
CORN OIL
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)
CORN OIL
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)
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of ETHYLAMINE OLEATE
SALT/SOLVATE -> PARENT
Structure of SORBITAN SESQUIOLEATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of OLEIC ACID
ACTIVE MOIETY
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