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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

Description

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

CNS Non-penetrant
1050
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
1447
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 61.31 µM [IC50]
Inhibitor
8228
SiHa
5
Target ID: CHEMBL612542
Inhibitor
8228
Inhibitor
8228
 185.0 nM [Ki]
Cholesteryl ester transfer protein
15
Target ID: P11597
Gene ID: 1071.0
Gene Symbol: CETP
Target Organism: Homo sapiens (Human)
Activator
1410
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
424
Unknown

Approved Use

Unknown
Primary
Phase I
424
Unknown

Approved Use

Unknown
Primary
Phase I
424
Unknown

Approved Use

Unknown
Preventing
Phase II
1144
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Fatty acids and derivatives as antimicrobial agents.
1972 Jul
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
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.
1995 Dec 1
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
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.
2000 Mar
Transdermal delivery of levosimendan.
2000 Oct
Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents.
2001 Jul
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.
2003 Feb 7
Exchanging carbohydrates for monounsaturated fats in energy-restricted diets: effects on metabolic profile and other cardiovascular risk factors.
2003 Jun
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
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
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
Dietary trans fatty acids and composition of human atheromatous plaques.
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
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
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
PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.
2006 May
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
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
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
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.
2010 Aug
Role of fat hydrolysis in regulating glucagon-like Peptide-1 secretion.
2010 Feb
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
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.
2013 Jul 5
Gustducin couples fatty acid receptors to GLP-1 release in colon.
2013 Mar 15
Fatty acids binding to human serum albumin: Changes of reactivity and glycation level of Cysteine-34 free thiol group with methylglyoxal.
2014 Dec 5
Structure-dependent binding and activation of perfluorinated compounds on human peroxisome proliferator-activated receptor γ.
2014 Sep 15
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
53
JP2004307635A
5
JP2005082715A
5
JP2008201951A
6
JP2010195782A
5
JP2010537404A
9
JP2011507590A
5
JP2011524743A
31
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
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.
Substance Class Chemical
Created
by admin
on Wed Jul 05 22:43:52 UTC 2023
Edited
by admin
on Wed Jul 05 22:43:52 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 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
Related Record Type Details
OLIVE OIL
LIPID -> FATTY ACID
TUNISIAN SOURCE
Structure of LEAD OLEATE
SALT/SOLVATE -> PARENT
COIX LACRYMA-JOBI SEED
PARENT -> CONSTITUENT ALWAYS PRESENT
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
EVENING PRIMROSE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of MERCURY OLEATE
SALT/SOLVATE -> PARENT
Structure of DIMETHYL LAURAMINE OLEATE
SALT/SOLVATE -> PARENT
KRILL OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of FRAMYCETIN OLEATE
SALT/SOLVATE -> PARENT
Structure of ETHANOLAMINE OLEATE
SALT/SOLVATE -> PARENT
Structure of ZINC OLEATE
SALT/SOLVATE -> PARENT
SESAME OIL
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
Structure of FERRIC OLEATE
SALT/SOLVATE -> PARENT
CANOLA OIL
LIPID -> FATTY ACID
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)
AVOCADO OIL
LIPID -> FATTY ACID
dependent on method of extraction
PEANUT OIL
LIPID -> FATTY ACID
Values are % of total.
Structure of PHENYLMERCURIC OLEATE
SALT/SOLVATE -> PARENT
FISH OIL
LIPID -> FATTY ACID
MAY BE PRESENT
USP
Structure of CALCIUM OLEATE
SALT/SOLVATE -> PARENT
RICE BRAN OIL
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
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.
BORAGE SEED OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of TRIETHANOLAMINE OLEATE
SALT/SOLVATE -> PARENT
PALM OIL
LIPID -> FATTY ACID
Values are % of total.
Structure of MORPHOLINE OLEATE
SALT/SOLVATE -> PARENT
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of SODIUM OLEATE
SALT/SOLVATE -> PARENT
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
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.
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of MAGNESIUM OLEATE
SALT/SOLVATE -> PARENT
Structure of COBALTOUS OLEATE
SALT/SOLVATE -> PARENT
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)
Structure of ETHYLAMINE OLEATE
SALT/SOLVATE -> PARENT
SPIRULINA
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of SORBITAN SESQUIOLEATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of Oleic acid
ACTIVE MOIETY
NIH
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