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Details

Stereochemistry ACHIRAL
Molecular Formula C18H32O2
Molecular Weight 280.4455
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of LINOLEIC ACID

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(O)=O

InChI

InChIKey=OYHQOLUKZRVURQ-HZJYTTRNSA-N
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-

HIDE SMILES / InChI
Molecular Formula C18H32O2
Molecular Weight 280.4455
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description

Linoleic acid is a naturally occurring omega-6 essential fatty acid, present in a variety of foods, including the oils. Linoleic acid is a precursor for arachidonic acid biosynthesis; on the first enzymatic step of the pathway involves delta-6-desaturase, which converts linoleic acid to gamma-lenolenic acid. Linoleic acid has beneficial effects on human skin and hair. Replacement of saturated fat with linoleic acid is advocated to improve serum lipoprotein profiles and reduce the risk of coronary artery disease. Linoleic acid was tested in clinical trilas as a possible remedy against multiple sclerosis.

CNS Activity

Approval Year

1921
1468
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
Intralipid

Approved Use

Intralipid® 10% is indicated as a source of calories and essential fatty acids for patients requiring parenteral nutrition for extended periods of time (usually for more than 5 days) and as a source of essential fatty acids for prevention of EFAD.

Launch Date

1996
Primary
Phase I
438
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Fatty acids and derivatives as antimicrobial agents.
1972 Jul
Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses.
1980 Dec
Cerebrospinal fluid lipids in demyelinating disease. II. Linoleic acid as an index of impaired blood-CSF barrier.
1980 Jan
Screening for new compounds with antiherpes activity.
1984 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
Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes.
1995 Dec 1
In Vivo Studies of the Biosynthesis of [alpha]-Eleostearic Acid in the Seed of Momordica charantia L.
1997 Apr
Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha.
1999 Jul 14
T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome.
2001 Apr
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
Organotropic chemopreventive effects of n-3 unsaturated fatty acids in a rat multi-organ carcinogenesis model.
2001 Nov
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.
2003 Feb
Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme.
2003 Jun
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
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
The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes.
2006 Nov 25
Comprehensive analysis of the effects of ordinary nutrients on hepatitis C virus RNA replication in cell culture.
2007 Jun
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
Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha.
2008 Mar
Changing ratios of omega-6 to omega-3 fatty acids can differentially modulate polychlorinated biphenyl toxicity in endothelial cells.
2008 Mar 10
A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine.
2008 May
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.
2012
Inhibition of matrix metalloproteinase-9 expression by docosahexaenoic acid mediated by heme oxygenase 1 in 12-O-tetradecanoylphorbol-13-acetate-induced MCF-7 human breast cancer cells.
2013 May
Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach.
2014 Jul
Bongkrekic acid as a selective activator of the peroxisome proliferator-activated receptor γ (PPARγ) isoform.
2015 Apr
Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets.
2015 Sep 18
Patents

Patents

JP2000247965A
4
JP2001081026A
4
JP2002146382A
4
JP2002501019A
7
JP2002533379A
53
JP2002536075A
14
JP2002536412A
7
JP2003508487A
10
JP2003533978A
6
JP2004236605A
5
JP2004256496A
4
JP2004531543A
5
JP2005194222A
4
JP2005314576A
4
JP2006230373A
4
JP2006282650A
4
JP2006321718A
4
JP2006326886A
4
JP2007135591A
4
JP2007176837A
4
JP2007504443A
9
JP2007514727A
4
JP2008113586A
4
JP2008540795A
5
JP2009051755A
4
JP2009084286A
4
JP2009132721A
4
JP2009184990A
4
JP2009256645A
4
JP2010195825A
4
JP2010502769A
10
JP2010535563A
8
JP2010538142A
5
JP2011103906A
4
JP2011503287A
5
JP2011508668A
16
JP2011524393A
8
JP2014195425A
4
JP2014201554A
4
JP3120091B2
9
JP4213205B2
14
JP4634804B2
4
JP4707659B2
4
JP4838936B2
15
JPH00491788A
4
JPH01135797A
4
JPH01186811A
8
JPH01300897A
4
JPH02113850A
4
JPH02178338A
7
JPH02191213A
4
JPH02283798A
4
JPH023498A
4
JPS56138111A
4
JPS6351486A
8
US2894909
4

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:44:59 GMT 2025
Edited
by admin
on Mon Mar 31 17:44:59 GMT 2025
Record UNII
9KJL21T0QJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EMERSOL 315
Preferred Name English
LINOLEIC ACID
FCC   HSDB   INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
Linoleic acid [WHO-DD]
Common Name English
LINOLEIC ACID [MI]
Common Name English
LINOLEIC ACID [VANDF]
Common Name English
LINOLEIC ACID [HSDB]
Common Name English
LINOLEIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
VITAMIN F COMPONENT LINOLEIC ACID
Common Name English
LINOLEIC ACID (CONSTITUENT OF FLAX SEED OIL) [DSC]
Common Name English
LINOLEIC ACID (CONSTITUENT OF BORAGE SEED OIL) [DSC]
Common Name English
RONACARE ASC 3
Brand Name English
LINOLIC ACID
Common Name English
NSC-281243
Code English
LINOLEIC ACID (C18:2) (CONSTITUENT OF KRILL OIL) [DSC]
Common Name English
9,12-LINOLEIC ACID
Common Name English
(Z,Z)-9,12-OCTADECADIENOIC ACID
Systematic Name English
LINOLEIC ACID [MART.]
Common Name English
FEMA NO. 3380, LINOLEIC ACID-
Code English
LINOLEATE
Systematic Name English
UNIFAC 6550
Brand Name English
C18:2 (N-6)
Common Name English
LINOLEIC ACID [FCC]
Common Name English
POLYLIN 515
Brand Name English
LINOLEIC ACID (CONSTITUENT OF SPIRULINA) [DSC]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C68398
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
LOINC 35165-0
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
LOINC 2564-3
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
LOINC 90917-6
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LOINC 75117-2
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
NCI_THESAURUS C2563
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CFR 21 CFR 357.210
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
CFR 21 CFR 184.1065
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LOINC 90915-0
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LOINC 47686-1
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DSLD 1537 (Number of products:578)
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
Code System Code Type Description
CHEBI
17351
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
WIKIPEDIA
LINOLEIC ACID
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
HSDB
5200
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
MESH
D019787
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
FDA UNII
9KJL21T0QJ
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
CAS
60-33-3
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PRIMARY
SMS_ID
100000077113
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
DRUG CENTRAL
3323
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
DRUG BANK
DB14104
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
MERCK INDEX
m6830
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C615
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
NSC
281243
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PRIMARY
PUBCHEM
5280450
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PRIMARY
RXCUI
6400
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
DAILYMED
9KJL21T0QJ
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-470-9
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
RXCUI
70611
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
ALTERNATIVE
EPA CompTox
DTXSID2025505
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
EVMPD
SUB14359MIG
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
PRIMARY
Related Record Type Details
PEANUT OIL
LIPID -> FATTY ACID
Coconut oil
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
AVOCADO OIL
LIPID -> FATTY ACID
KRILL OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
CORN OIL
LIPID -> FATTY ACID
Value is fatty acid composition (%) for US corn oil w/std. deviation of 1.20% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
Structure of MANGANESE LINOLEATE
SALT/SOLVATE -> PARENT
CANOLA OIL
LIPID -> FATTY ACID
Structure of AMMONIUM LINOLEATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM LINOLEATE
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)
Structure of ZINC LINOLEATE
SALT/SOLVATE -> PARENT
SESAME OIL
LIPID -> FATTY ACID
CORN OIL
LIPID -> FATTY ACID
Value is fatty acid composition (%) for international corn oil w/std. deviation of 2.4% LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
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)
Structure of ALUMINIUM TRILINOLEATE
SALT/SOLVATE -> PARENT
ELYMUS REPENS ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
Compound measured as 2.50% of the composition of the steam distillate of Elymus repens rhizome as per R Boesel in Planta Medica iss:4 pg:399-400, 1989.
OLIVE OIL
LIPID -> FATTY ACID
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
CANNABIS SATIVA SUBSP. INDICA TOP
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
FISH OIL
LIPID -> FATTY ACID
USP
Structure of SODIUM LINOLEATE
SALT/SOLVATE -> PARENT
Structure of COPPER LINOLEATE
SALT/SOLVATE -> PARENT
SAFFLOWER OIL
LIPID -> FATTY ACID
SPIRULINA
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of COBALTOUS LINOLEATE
SALT/SOLVATE -> PARENT
Structure of Cadmium linoleate
SALT/SOLVATE -> PARENT
RICE BRAN OIL
LIPID -> FATTY ACID
PALM OIL
LIPID -> FATTY ACID
BORAGE SEED OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
Structure of MERCURIC LINOLEATE
SALT/SOLVATE -> PARENT
Structure of CALCIUM LINOLEATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of LINOLEIC ACID
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