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
Oleic acid is an unsaturated fatty acid that is the most widely distributed and abundant fatty acid in nature. It is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Oleic acid occurs naturally in various animal and vegetable fats and oils. It is a component of the normal human diet as a part of animal fats and vegetable oils. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil. Oleic acid has being shown to have a potential anticancer activity.

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
Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein.
1994 Nov 4
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
Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women.
1999 Jan
Significance of fatty acids in pregnancy-induced immunosuppression.
1999 Jul
Fat and mesenteric blood flow.
1999 Sep
Identification of the major intestinal fatty acid transport protein.
1999 Sep
Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man.
2000
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
2000 Jun 20
Transdermal delivery of levosimendan.
2000 Oct
Down-regulation of uncoupling protein-3 and -2 by thiazolidinediones in C2C12 myotubes.
2000 Oct 27
Behenic acid is a cholesterol-raising saturated fatty acid in humans.
2001 Jan
Discovery of gemifloxacin (Factive, LB20304a): a quinolone of a new generation.
2001 Jan-Feb
Novel approach to improve permeation of ondansetron across shed snake skin as a model membrane.
2001 Jun
Effects of sucrose oleate and sucrose laureate on in vivo human stratum corneum permeability.
2003 Aug
Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells.
2003 Dec
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
What does the measurement of whole-body fatty acid rate of appearance in plasma by using a fatty acid tracer really mean?
2003 Jul
Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme.
2003 Jun
Exchanging carbohydrates for monounsaturated fats in energy-restricted diets: effects on metabolic profile and other cardiovascular risk factors.
2003 Jun
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.
2003 Mar 28
Decreasing IRS-2 expression in pancreatic beta-cells (INS-1) promotes apoptosis, which can be compensated for by introduction of IRS-4 expression.
2003 Nov 14
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
Stearoyl-CoA desaturase 1 gene expression is necessary for fructose-mediated induction of lipogenic gene expression by sterol regulatory element-binding protein-1c-dependent and -independent mechanisms.
2004 Jun 11
Fatty acid sensor for low-cost lifetime-assisted ratiometric sensing using a fluorescent fatty acid binding protein.
2005 Oct 1
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
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.
2008 Jan
Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus.
2008 Sep
Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion.
2010 Feb
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
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
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
Patents

Sample Use Guides

diet, containing 15% energy as fat from dairy products, meat, bread and cereals, was supplemented with oleic or elaidic acid
Route of Administration: Oral
In Vitro Use Guide
It was studied the impact of both cis and trans forms of C 18:1 fatty acids. It was found that cis and trans vaccenic acid (cis and trans C 18:1 delta11), as well as oleic acid (cis C 18:1 delta9) and elaidic acid (trans 18:1 delta9), caused a dose-dependent increase in glucose (16.7 mmol/L)-stimulated insulin secretion during static islet incubations. The maximal stimulatory effect for cis and trans vaccenic acid and for oleic and elaidic acid was observed at concentrations of 2.0 and 3.0 mmol/L, respectively. The trans isomers, trans vaccenic and elaidic acid, elicited a higher maximal insulin output than the respective cis isomers, cis vaccenic and oleic acid. In the presence of another insulin secretagogue, L-leucine, trans vaccenic but not elaidic acid caused a higher response than their cis isomeric fatty acids.
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 Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
LOINC 2673-2
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
CFR 21 CFR 172.210
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
LOINC 35166-8
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
LOINC 75102-4
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
CFR 21 CFR 172.862
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
CFR 21 CFR 172.860
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
LOINC 47713-3
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
LOINC 27108-0
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
DSLD 262 (Number of products:639)
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
JECFA EVALUATION OLEIC ACID
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
LOINC 74620-6
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
LOINC 74621-4
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C68405
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
FDA UNII
2UMI9U37CP
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
ChEMBL
CHEMBL8659
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
DAILYMED
2UMI9U37CP
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
DRUG CENTRAL
3400
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
MESH
D019301
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
HSDB
1240
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
PUBCHEM
445639
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
CHEBI
16196
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-007-1
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
RXCUI
70616
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
ALTERNATIVE
RXCUI
7631
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
EPA CompTox
DTXSID1025809
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
CAS
112-80-1
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
WIKIPEDIA
OLEIC ACID
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
RS_ITEM_NUM
1478130
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
NSC
9856
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
RXCUI
32559
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
ALTERNATIVE
DRUG BANK
DB04224
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
SMS_ID
100000091945
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
EVMPD
SUB12542MIG
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY
MERCK INDEX
M8191
Created by admin on Wed Jul 05 22:43:53 UTC 2023 , Edited by admin on Wed Jul 05 22:43:53 UTC 2023
PRIMARY Merck Index