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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
1467
Targets

Targets

Primary TargetPharmacologyConditionPotency
Activator
1430
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
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
428
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
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
Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts.
2003 Aug 30
Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme.
2003 Jun
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
2003 Mar 13
Zinc modulates PPARgamma signaling and activation of porcine endothelial cells.
2003 Oct
Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells.
2004 Feb
Binding analyses between Human PPARgamma-LBD and ligands.
2004 Jan
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
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
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
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?
2006 Aug
Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification.
2006 Jul
The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes.
2006 Nov 25
Cyclooxygenase-2 promoter activation by the aromatic hydrocarbon receptor in breast cancer mcf-7 cells: repressive effects of conjugated linoleic acid.
2007
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
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
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
Role of polyunsaturated fatty acids in the management of Egyptian children with autism.
2008 Sep
Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus.
2008 Sep
Identification of an endogenous ligand bound to a native orphan nuclear receptor.
2009
Optimization of an enzyme-linked immunosorbent assay to screen ligand of Peroxisome proliferator-activated receptor alpha.
2009
Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms.
2010 Aug
Bezafibrate mildly stimulates ketogenesis and fatty acid metabolism in hypertriglyceridemic subjects.
2010 Jul
Regulation of stearoyl-coenzyme A desaturase and fatty acid delta-6 desaturase-2 expression by linoleic acid and arachidonic acid in human sebocytes leads to enhancement of proinflammatory activity but does not affect lipogenesis.
2011 Aug
A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis.
2012
TGF-β-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury.
2012 Dec
New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors.
2012 Nov
Advanced glycation end products (AGE) induce the receptor for AGE in the colonic mucosa of azoxymethane-injected Fischer 344 rats fed with a high-linoleic acid and high-glucose diet.
2012 Oct
Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells.
2012 Sep
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
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 Îł (PPARÎł) 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 Fri Dec 15 15:03:37 GMT 2023
Edited
by admin
on Fri Dec 15 15:03:37 GMT 2023
Record UNII
9KJL21T0QJ
Record Status Validated (UNII)
Record Version
  • Download
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 [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
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
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 Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
LOINC 35165-0
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
LOINC 2564-3
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LOINC 90917-6
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
LOINC 75117-2
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
NCI_THESAURUS C2563
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
CFR 21 CFR 357.210
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
CFR 21 CFR 184.1065
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
LOINC 90915-0
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
LOINC 47686-1
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DSLD 1537 (Number of products:578)
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
Code System Code Type Description
CHEBI
17351
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
WIKIPEDIA
LINOLEIC ACID
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
HSDB
5200
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
MESH
D019787
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
FDA UNII
9KJL21T0QJ
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
CAS
60-33-3
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
SMS_ID
100000077113
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
DRUG CENTRAL
3323
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
DRUG BANK
DB14104
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
MERCK INDEX
m6830
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C615
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
NSC
281243
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
PUBCHEM
5280450
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PRIMARY
RXCUI
6400
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
DAILYMED
9KJL21T0QJ
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-470-9
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
RXCUI
70611
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
ALTERNATIVE
EPA CompTox
DTXSID2025505
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
EVMPD
SUB14359MIG
Created by admin on Fri Dec 15 15:03:38 GMT 2023 , Edited by admin on Fri Dec 15 15:03:38 GMT 2023
PRIMARY
Related Record Type Details
Coconut oil
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
PEANUT OIL
LIPID -> FATTY ACID
Values are % of total.
RICE BRAN OIL
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
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
KRILL OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
CANOLA OIL
LIPID -> FATTY ACID
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 15.00% by composition.
SPIRULINA
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
Structure of AMMONIUM LINOLEATE
SALT/SOLVATE -> PARENT
Structure of POTASSIUM LINOLEATE
SALT/SOLVATE -> PARENT
PALM OIL
LIPID -> FATTY ACID
Values are % of total.
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
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
varies depending of method of extraction
Structure of ZINC LINOLEATE
SALT/SOLVATE -> PARENT
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)
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
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
EUROPEAN SOURCE
ARCTIUM LAPPA ROOT
PARENT -> CONSTITUENT ALWAYS PRESENT
CANNABIS SATIVA SUBSP. INDICA TOP
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
FISH OIL
LIPID -> FATTY ACID
USP
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
BORAGE SEED OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
COD LIVER OIL
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SUNFLOWER OIL
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
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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