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Details

Stereochemistry ACHIRAL
Molecular Formula C18H32O2
Molecular Weight 280.4462
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of LINOLEIC ACID

SMILES

CCCCC/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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

839289600000
Primary
PubMed

PubMed

TitleDatePubMed
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
Physiology and pathophysiology of organic acids in cerebrospinal fluid.
1993
Evidence for a novel keratinocyte fatty acid uptake mechanism with preference for linoleic acid: comparison of oleic and linoleic acid uptake by cultured human keratinocytes, fibroblasts and a human hepatoma cell line.
1994 Feb 10
Pseudo-acylceramide with linoleic acid produces selective recovery of diminished cutaneous barrier function in essential fatty acid-deficient rats and has an inhibitory effect on epidermal hyperplasia.
1994 Jul
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
Plasma saturated and linoleic fatty acids are independently associated with blood pressure.
1999 Sep
Low-saturated fat, low-cholesterol diet in 3-year-old children: effect on intake and composition of trans fatty acids and other fatty acids in serum phospholipid fraction-The STRIP study. Special Turku coronary Risk factor Intervention Project for children.
2000 Jan
Zinc protects against apoptosis of endothelial cells induced by linoleic acid and tumor necrosis factor alpha.
2000 Jan
Organotropic chemopreventive effects of n-3 unsaturated fatty acids in a rat multi-organ carcinogenesis model.
2001 Nov
Linoleic acid both enhances activation and blocks Kv1.5 and Kv2.1 channels by two separate mechanisms.
2001 Oct
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
Linoleic acid supplementation of Barth syndrome fibroblasts restores cardiolipin levels: implications for treatment.
2003 Mar
Zinc modulates PPARgamma signaling and activation of porcine endothelial cells.
2003 Oct
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
Binding analyses between Human PPARgamma-LBD and ligands.
2004 Jan
Omega-3 fatty acids inhibit an increase of proinflammatory cytokines in patients with active Crohn's disease compared with omega-6 fatty acids.
2005 Dec
Expression of cFABP and PPAR in trophoblast cells: effect of PPAR ligands on linoleic acid uptake and differentiation.
2005 Feb 21
Specificity of receptor-ligand interactions and their effect on dimerisation as observed by electrospray mass spectrometry: bile acids form stable adducts to the RXRalpha.
2005 Nov
Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity.
2005 Oct
Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway.
2005 Oct 28
Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules.
2006 Jul
Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification.
2006 Jul
Role of FoxO1 in FFA-induced oxidative stress in adipocytes.
2007 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
Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes.
2008 Jan
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
Role of polyunsaturated fatty acids in the management of Egyptian children with autism.
2008 Sep
Bezafibrate mildly stimulates ketogenesis and fatty acid metabolism in hypertriglyceridemic subjects.
2010 Jul
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.
2012
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.
2013 Jul 5
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
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
Name Type Language
LINOLEIC ACID
FCC   HSDB   INCI   MART.   MI   VANDF   WHO-DD  
INCI  
Official Name English
LINOLEIC ACID [INCI]
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
EMERSOL 315
Brand 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
LINOLEIC ACID [WHO-DD]
Common 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 Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 35165-0
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 2564-3
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 90917-6
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 75117-2
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
NCI_THESAURUS C2563
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
CFR 21 CFR 357.210
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
CFR 21 CFR 184.1065
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 90915-0
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
LOINC 47686-1
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
DSLD 1537 (Number of products:578)
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
Code System Code Type Description
WIKIPEDIA
LINOLEIC ACID
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
HSDB
5200
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
MESH
D019787
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
FDA UNII
9KJL21T0QJ
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
CAS
60-33-3
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
DRUG CENTRAL
3323
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
DRUG BANK
DB14104
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
MERCK INDEX
M6830
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C615
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
PUBCHEM
5280450
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
RXCUI
6400
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-470-9
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
RXCUI
70611
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
ALTERNATIVE
EPA CompTox
60-33-3
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY
EVMPD
SUB14359MIG
Created by admin on Sat Jun 26 06:12:02 UTC 2021 , Edited by admin on Sat Jun 26 06:12:02 UTC 2021
PRIMARY