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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

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

1996
Primary
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
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
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
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
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
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
Quercetin protects against linoleic acid-induced porcine endothelial cell dysfunction.
2004 Apr
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
Comprehensive analysis of the effects of ordinary nutrients on hepatitis C virus RNA replication in cell culture.
2007 Jun
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
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
New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors.
2012 Nov
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
Patents

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
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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
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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
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
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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
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PRIMARY
NSC
281243
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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
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
LIPID -> FATTY ACID
Values are % of total.
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
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)
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
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.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Values are % of total.
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
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)
LIPID -> FATTY ACID
varies depending of method of extraction
SALT/SOLVATE -> PARENT
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)
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)
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
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.
LIPID -> FATTY ACID
EUROPEAN SOURCE
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
LIPID -> FATTY ACID
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY