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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

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
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
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
[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
Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man.
2000
Transdermal delivery of levosimendan.
2000 Oct
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
Behenic acid is a cholesterol-raising saturated fatty acid in humans.
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
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
Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells.
2003 Dec
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
Accuracy of the double indicator method for measurement of extravascular lung water depends on the type of acute lung injury.
2004 Mar
Fat mobilization in adipose tissue is promoted by adipose triglyceride lipase.
2004 Nov 19
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers.
2004 Sep-Oct
Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120.
2005 Jan
Glucosamine-induced endoplasmic reticulum stress promotes ApoB100 degradation: evidence for Grp78-mediated targeting to proteasomal degradation.
2005 Mar
Fatty acids and expression of adipokines.
2005 May 30
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
Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men.
2007 Apr
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
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.
2008 Jan
[Effects of recruitment maneuvers in prone position for pulmonary or extra-pulmonary acute respiratory distress syndrome on hemodynamics in dog].
2008 Jun
Regulation of fat-stimulated neurotensin secretion in healthy subjects.
2008 May
PPARalpha-mediated effects of dietary lipids on intestinal barrier gene expression.
2008 May 19
Activation of group IVC phospholipase A(2) by polycyclic aromatic hydrocarbons induces apoptosis of human coronary artery endothelial cells.
2011 Jun
Differential signaling by splice variants of the human free fatty acid receptor GPR120.
2012 May
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
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
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 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
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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
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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
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
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
LIPID -> FATTY ACID
Value is % of total fatty acids. Goden VJ, Spensley PC; Oils and Oilseeds, TPI, London, 1971, p.151
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
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.
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 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)
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
LIPID -> FATTY ACID
MAY BE PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
Values are % of total.
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
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
IOOC limits
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.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
dependent on method of extraction
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)
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY