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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
Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses.
1980 Dec
Screening for new compounds with antiherpes activity.
1984 Oct
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
Lipid peroxides induce expression of catalase in cultured vascular cells.
2000 Aug
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
Essential fatty acid metabolism and its modification in atopic eczema.
2000 Jan
Zinc protects against apoptosis of endothelial cells induced by linoleic acid and tumor necrosis factor alpha.
2000 Jan
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
2000 Jun 20
Binding of prostaglandins to human PPARgamma: tool assessment and new natural ligands.
2001 Apr 6
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
Organotropic chemopreventive effects of n-3 unsaturated fatty acids in a rat multi-organ carcinogenesis model.
2001 Nov
Linoleic acid, other fatty acids, and the risk of stroke.
2002 Aug
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
Cytosolic phospholipase A2 (cPLA2) regulation of human monocyte NADPH oxidase activity. cPLA2 affects translocation but not phosphorylation of p67(phox) and p47(phox).
2002 Jul 12
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
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.
2003 Mar 28
Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization.
2003 Oct 15
Quercetin protects against linoleic acid-induced porcine endothelial cell dysfunction.
2004 Apr
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
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
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
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
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
Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus.
2008 Sep
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
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
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LOINC 75117-2
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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
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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 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
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PRIMARY
MESH
D019787
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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
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PRIMARY
SMS_ID
100000077113
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PRIMARY
DRUG CENTRAL
3323
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PRIMARY
DRUG BANK
DB14104
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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
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PRIMARY
NSC
281243
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PRIMARY
PUBCHEM
5280450
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PRIMARY
RXCUI
6400
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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
ACTIVE MOIETY
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