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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
1040
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
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 61.31 µM [IC50]
Inhibitor
8504
SiHa
5
Target ID: CHEMBL612542
Inhibitor
8504
Inhibitor
8504
 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
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Preventing
Phase II
1147
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
Hypothalamic modulation of growth hormone secretion in the rhesus monkey: evidence from intracerebroventricular infusions of glucose, free fatty acid, and ketone bodies.
1991 Oct
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Involvement of endogenous cholecystokinin and somatostatin in gastroprotection induced by intraduodenal fat.
1998
Effect of fatty acid chain length and saturation on the gastrointestinal handling and metabolic disposal of dietary fatty acids in women.
1999 Jan
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
Substituting enzymatically interesterified butter for native butter has no effect on lipemia or lipoproteinemia in Man.
2000
Antiviral activity of ganciclovir elaidic acid ester against herpesviruses.
2000 Mar
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
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
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
Fatty acids alter monolayer integrity, paracellular transport, and iron uptake and transport in Caco-2 cells.
2003 Dec
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.
2003 Feb 7
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
Effects of rosiglitazone and oleic acid on UCP-3 expression in L6 myotubes.
2003 Mar
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
2003 Mar 13
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
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
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?
2006 Aug
Albumin-bound fatty acids induce mitochondrial oxidant stress and impair antioxidant responses in proximal tubular cells.
2006 Aug
Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha.
2006 Aug
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
Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids.
2008 Jul
Regulation of fat-stimulated neurotensin secretion in healthy subjects.
2008 May
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
PKC activation by resveratrol derivatives with unsaturated aliphatic chain.
2012
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
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 Mon Mar 31 17:50:09 GMT 2025
Edited
by admin
on Mon Mar 31 17:50:09 GMT 2025
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
18:1(N-9)
Preferred 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
FEMA NO. 2815
Code English
9-OCTADECENOIC ACID, (Z)-
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 Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
LOINC 2673-2
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
CFR 21 CFR 172.210
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
LOINC 35166-8
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LOINC 75102-4
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CFR 21 CFR 172.862
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
CFR 21 CFR 172.860
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
LOINC 47713-3
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
LOINC 27108-0
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DSLD 262 (Number of products:639)
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
JECFA EVALUATION OLEIC ACID
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
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 Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY
FDA UNII
2UMI9U37CP
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY
ChEMBL
CHEMBL8659
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY
DAILYMED
2UMI9U37CP
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY
DRUG CENTRAL
3400
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PRIMARY
MESH
D019301
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PRIMARY
HSDB
1240
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PRIMARY
PUBCHEM
445639
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PRIMARY
JECFA MONOGRAPH
68
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PRIMARY
CHEBI
16196
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-007-1
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY
RXCUI
70616
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
ALTERNATIVE
RXCUI
7631
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PRIMARY
EPA CompTox
DTXSID1025809
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PRIMARY
CAS
112-80-1
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY
WIKIPEDIA
OLEIC ACID
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY
RS_ITEM_NUM
1478130
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY
NSC
9856
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PRIMARY
RXCUI
32559
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
ALTERNATIVE
DRUG BANK
DB04224
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PRIMARY
SMS_ID
100000091945
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PRIMARY
EVMPD
SUB12542MIG
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PRIMARY
MERCK INDEX
m8191
Created by admin on Mon Mar 31 17:50:09 GMT 2025 , Edited by admin on Mon Mar 31 17:50:09 GMT 2025
PRIMARY Merck Index
Related Record Type Details
SESAME OIL
LIPID -> FATTY ACID
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
Structure of MERCURY OLEATE
SALT/SOLVATE -> PARENT
Structure of DIMETHYL LAURAMINE OLEATE
SALT/SOLVATE -> PARENT
SPIRULINA
PARENT -> CONSTITUENT ALWAYS PRESENT
EVENING PRIMROSE OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
AVOCADO OIL
LIPID -> FATTY ACID
Structure of FRAMYCETIN OLEATE
SALT/SOLVATE -> PARENT
PEANUT OIL
LIPID -> FATTY ACID
Structure of ETHANOLAMINE OLEATE
SALT/SOLVATE -> PARENT
Structure of ZINC OLEATE
SALT/SOLVATE -> PARENT
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.
KRILL OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of COPPER OLEATE
SALT/SOLVATE -> PARENT
PALM OIL
LIPID -> FATTY ACID
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)
Moringa Acid
PARENT -> CONSTITUENT ALWAYS PRESENT
MAJOR
AMOUNT PRESENT
Structure of PHENYLMERCURIC OLEATE
SALT/SOLVATE -> PARENT
FISH OIL
LIPID -> FATTY ACID
MAY BE PRESENT
USP
SAFFLOWER OIL
LIPID -> FATTY ACID
Structure of CALCIUM OLEATE
SALT/SOLVATE -> PARENT
BORAGE SEED OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of TRIETHANOLAMINE OLEATE
SALT/SOLVATE -> PARENT
OLIVE OIL
LIPID -> FATTY ACID
Structure of MORPHOLINE OLEATE
SALT/SOLVATE -> PARENT
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of SODIUM OLEATE
SALT/SOLVATE -> PARENT
RICE BRAN OIL
LIPID -> FATTY ACID
Structure of POTASSIUM OLEATE
SALT/SOLVATE -> PARENT
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.
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of MAGNESIUM OLEATE
SALT/SOLVATE -> PARENT
Structure of COBALTOUS OLEATE
SALT/SOLVATE -> PARENT
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
Moringa peregrina seed oil fatty acids
PARENT -> CONSTITUENT ALWAYS PRESENT
MAJOR
AMOUNT PRESENT
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
Structure of SORBITAN SESQUIOLEATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of Oleic acid
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