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
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-
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11478373
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
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4822 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24548007 |
61.31 µM [IC50] | ||
Target ID: CHEMBL3455 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24191036 |
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Target ID: CHEMBL612542 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25430075 |
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Target ID: CHEMBL2083 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17502136 |
185.0 nM [Ki] | ||
Target ID: P11597 Gene ID: 1071.0 Gene Symbol: CETP Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8018112 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Preventing | Unknown Approved UseUnknown |
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PubMed
Title | Date | PubMed |
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Fatty acids and derivatives as antimicrobial agents. | 1972 Jul |
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Effects of hydralazine on cardiopulmonary function in canine low-pressure pulmonary edema. | 1983 Sep |
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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 |
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Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein. | 1994 Nov 4 |
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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 |
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Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes. | 1995 Dec 1 |
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Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat. | 1998 |
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[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 |
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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 |
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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 |
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Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates. | 2001 Jan 15 |
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Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation. | 2001 Jan-Feb |
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Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents. | 2001 Jul |
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Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane. | 2001 Jun |
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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 |
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Enhanced GLUT2 gene expression in an oleic acid-induced in vitro fatty liver model. | 2002 Jun |
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A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs. | 2003 Feb 7 |
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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 |
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Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme. | 2003 Jun |
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The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids. | 2003 Mar 28 |
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Characterization of a heart-specific fatty acid transport protein. | 2003 May 2 |
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Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization. | 2003 Oct 15 |
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Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004 Dec |
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Copper ions and hypochlorite are mainly responsible for oxidative inactivation of paraoxon-hydrolyzing activity in human high density lipoprotein. | 2004 Mar 7 |
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COPD results in a reduction in UCP3 long mRNA and UCP3 protein content in types I and IIa skeletal muscle fibers. | 2004 Sep-Oct |
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Lipid metabolism in trained rats: effect of guarana (Paullinia cupana Mart.) supplementation. | 2005 Dec |
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Free fatty acids regulate gut incretin glucagon-like peptide-1 secretion through GPR120. | 2005 Jan |
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Fatty acids and expression of adipokines. | 2005 May 30 |
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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 |
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The repression of E2F-1 is critical for the activity of Minerval against cancer. | 2005 Oct |
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Fatty acid sensor for low-cost lifetime-assisted ratiometric sensing using a fluorescent fatty acid binding protein. | 2005 Oct 1 |
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Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway. | 2005 Oct 28 |
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High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids? | 2006 Aug |
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Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells. | 2006 Aug |
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Dual inhibition of mycobacterial fatty acid biosynthesis and degradation by 2-alkynoic acids. | 2006 Mar |
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PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver. | 2006 May |
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Effect of CCK-1 receptor blockade on ghrelin and PYY secretion in men. | 2007 Apr |
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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 |
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Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes. | 2008 Jan |
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Regulation of fat-stimulated neurotensin secretion in healthy subjects. | 2008 May |
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Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion. | 2010 Feb |
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PKC activation by resveratrol derivatives with unsaturated aliphatic chain. | 2012 |
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Differential signaling by splice variants of the human free fatty acid receptor GPR120. | 2012 May |
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Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line. | 2012 Oct 15 |
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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 |
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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 |
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Gustducin couples fatty acid receptors to GLP-1 release in colon. | 2013 Mar 15 |
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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 |
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Structure-dependent binding and activation of perfluorinated compounds on human peroxisome proliferator-activated receptor γ. | 2014 Sep 15 |
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The interplay between hepatic stellate cells and hepatocytes in an in vitro model of NASH. | 2015 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23376733
Rats were gavaged with oleic acid FFA (500 mg/10 mL/kg)
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24548007
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
Edited
Fri Dec 15 15:12:27 GMT 2023
by
admin
on
Fri Dec 15 15:12:27 GMT 2023
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Record UNII |
2UMI9U37CP
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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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 | ||
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C68405
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2UMI9U37CP
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CHEMBL8659
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2UMI9U37CP
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PRIMARY | |||
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3400
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D019301
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1240
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445639
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68
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16196
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204-007-1
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70616
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7631
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DTXSID1025809
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112-80-1
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OLEIC ACID
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1478130
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9856
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32559
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DB04224
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100000091945
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SUB12542MIG
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m8191
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
JB Rossell and co-workers; JAOCS62(2), 221-230(1985).
Range weight is a mean.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
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LIPID -> FATTY ACID |
dependent on method of extraction
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LIPID -> FATTY ACID | |||
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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)
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PARENT -> CONSTITUENT ALWAYS PRESENT |
From Cannabis seed oil.
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Values are % of total.
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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)
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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.
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID |
MAY BE PRESENT
USP
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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SALT/SOLVATE -> PARENT |
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LIPID -> FATTY ACID |
U.S produced rice oil. Values are % of composition.
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Values given are in undefined precent.
Average is typical for U.S. Sunflower oil.
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SALT/SOLVATE -> PARENT | |||
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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.
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LIPID -> FATTY ACID |
Values are % of total.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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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
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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)
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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)
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LIPID -> FATTY ACID |
TUNISIAN SOURCE
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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