U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Effect of sodium nitroprusside on cardiovascular function and pulmonary shunt in canine oleic acid pulmonary edema.
1981 Nov
Effects of acute lung injury and anesthesia on left ventricular mechanics.
1986 Dec
Hypothalamic modulation of growth hormone secretion in the rhesus monkey: evidence from intracerebroventricular infusions of glucose, free fatty acid, and ketone bodies.
1991 Oct
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
Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat.
1998
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.
1999 Jul 14
Fat and mesenteric blood flow.
1999 Sep
Identification of the major intestinal fatty acid transport protein.
1999 Sep
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
2000 Jun 20
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.
2000 Mar
Transdermal delivery of levosimendan.
2000 Oct
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
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
Regulation of uncoupling protein-2 mRNA in L6 myotubules: II: Thyroid hormone amplifies stimulation of uncoupling protein-2 gene by thiazolidinediones and other peroxisome proliferator-activated receptor ligands in L6 myotubules: evidence for a priming effect.
2002 Nov
Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells.
2003 Dec
What does the measurement of whole-body fatty acid rate of appearance in plasma by using a fatty acid tracer really mean?
2003 Jul
Exchanging carbohydrates for monounsaturated fats in energy-restricted diets: effects on metabolic profile and other cardiovascular risk factors.
2003 Jun
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
2003 Mar 13
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
Copper ions and hypochlorite are mainly responsible for oxidative inactivation of paraoxon-hydrolyzing activity in human high density lipoprotein.
2004 Mar 7
Fat mobilization in adipose tissue is promoted by adipose triglyceride lipase.
2004 Nov 19
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
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.
2005 Oct 28
Dual inhibition of mycobacterial fatty acid biosynthesis and degradation by 2-alkynoic acids.
2006 Mar
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
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
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
PPAR agonists reduce steatosis in oleic acid-overloaded HepaRG cells.
2014 Apr 1
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
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:12:27 UTC 2023
Edited
by admin
on Fri Dec 15 15:12:27 UTC 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
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
LOINC 2673-2
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
CFR 21 CFR 172.210
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
LOINC 35166-8
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
LOINC 75102-4
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
CFR 21 CFR 172.862
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
CFR 21 CFR 172.860
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
LOINC 47713-3
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
LOINC 27108-0
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
DSLD 262 (Number of products:639)
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
JECFA EVALUATION OLEIC ACID
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
LOINC 74620-6
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
LOINC 74621-4
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C68405
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
FDA UNII
2UMI9U37CP
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL8659
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
DAILYMED
2UMI9U37CP
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
DRUG CENTRAL
3400
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
MESH
D019301
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
HSDB
1240
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
PUBCHEM
445639
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
JECFA MONOGRAPH
68
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
CHEBI
16196
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-007-1
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
RXCUI
70616
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
ALTERNATIVE
RXCUI
7631
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID1025809
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
CAS
112-80-1
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
WIKIPEDIA
OLEIC ACID
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
RS_ITEM_NUM
1478130
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
NSC
9856
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
RXCUI
32559
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
ALTERNATIVE
DRUG BANK
DB04224
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
SMS_ID
100000091945
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
EVMPD
SUB12542MIG
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 2023
PRIMARY
MERCK INDEX
m8191
Created by admin on Fri Dec 15 15:12:27 UTC 2023 , Edited by admin on Fri Dec 15 15:12:27 UTC 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