U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
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
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
T cells ignore aniline, a prohapten, but respond to its reactive metabolites generated by phagocytes: possible implications for the pathogenesis of toxic oil syndrome.
2001 Apr
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates.
2001 Jan 15
Arachidonic and linoleic acid metabolism in mouse intestinal tissue: evidence for novel lipoxygenase activity.
2002 Feb 1
Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation.
2002 Jun
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.
2003 Feb
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
Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells.
2004 Feb
Expression of cFABP and PPAR in trophoblast cells: effect of PPAR ligands on linoleic acid uptake and differentiation.
2005 Feb 21
Cyclooxygenase-2 promoter activation by the aromatic hydrocarbon receptor in breast cancer mcf-7 cells: repressive effects of conjugated linoleic acid.
2007
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
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
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
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
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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
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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