U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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

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
Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses.
1980 Dec
Screening for new compounds with antiherpes activity.
1984 Oct
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
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
Binding of prostaglandins to human PPARgamma: tool assessment and new natural ligands.
2001 Apr 6
Organotropic chemopreventive effects of n-3 unsaturated fatty acids in a rat multi-organ carcinogenesis model.
2001 Nov
Arachidonic and linoleic acid metabolism in mouse intestinal tissue: evidence for novel lipoxygenase activity.
2002 Feb 1
Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models.
2002 Jan
Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation.
2002 Jun
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.
2003 Feb 7
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?
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
Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules.
2006 Jul
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
Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids.
2008 Jul
Comparison of hypolipidemic activity of synthetic gallic acid-linoleic acid ester with mixture of gallic acid and linoleic acid, gallic acid, and linoleic acid on high-fat diet induced obesity in C57BL/6 Cr Slc mice.
2008 Jul 30
Changing ratios of omega-6 to omega-3 fatty acids can differentially modulate polychlorinated biphenyl toxicity in endothelial cells.
2008 Mar 10
Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus.
2008 Sep
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
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
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 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
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 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
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 90915-0
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 47686-1
Created by admin on Mon Mar 31 17:45:00 GMT 2025 , Edited by admin on Mon Mar 31 17:45:00 GMT 2025
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
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
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
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
PUBCHEM
5280450
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
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
ACTIVE MOIETY
Structure of LINOLEIC ACID
SALT/SOLVATE (PARENT)
Structure of MANGANESE LINOLEATE
SALT/SOLVATE (PARENT)
Structure of AMMONIUM LINOLEATE
SALT/SOLVATE (PARENT)
Structure of POTASSIUM LINOLEATE
SALT/SOLVATE (PARENT)
Structure of ZINC LINOLEATE
SALT/SOLVATE (PARENT)
Structure of ALUMINIUM TRILINOLEATE
SALT/SOLVATE (PARENT)
Structure of SODIUM LINOLEATE
SALT/SOLVATE (PARENT)
Structure of COPPER LINOLEATE
SALT/SOLVATE (PARENT)
Structure of COBALTOUS LINOLEATE
SALT/SOLVATE (PARENT)
Structure of Cadmium linoleate
SALT/SOLVATE (PARENT)
Structure of MERCURIC LINOLEATE
SALT/SOLVATE (PARENT)
Structure of CALCIUM LINOLEATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966