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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

Molecular Formula C18H32O2
Molecular Weight 280.4462
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

There is existed not much information about ammonium salt of linoleic acid, AMMONIUM LINOLEATE. But is known, that this compound is auto oxidized.

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

8.392896E11
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cerebrospinal fluid lipids in demyelinating disease. II. Linoleic acid as an index of impaired blood-CSF barrier.
1980 Jan
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
Zinc protects against apoptosis of endothelial cells induced by linoleic acid and tumor necrosis factor alpha.
2000 Jan
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
Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates.
2001 Jan 15
Linoleic acid, other fatty acids, and the risk of stroke.
2002 Aug
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
Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts.
2003 Aug 30
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.
2003 Feb
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
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
2003 Mar 13
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
Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids.
2004 Dec
Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells.
2004 Feb
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids?
2006 Aug
Cyclooxygenase-2 promoter activation by the aromatic hydrocarbon receptor in breast cancer mcf-7 cells: repressive effects of conjugated linoleic acid.
2007
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
TGF-β-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury.
2012 Dec
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
Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice.
2013 Jul 5
Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach.
2014 Jul
Patents

Sample Use Guides

Linoleic acid emulsion is administered at a dose of 30 g two times daily.
Route of Administration: Oral
In Vitro Use Guide
Lymphocytes from patients with multiple sclerosis were incubated with linoleic acid at concnetration of 0.08 mg/ml and the inhibition achieved 91%.
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:12:01 UTC 2021
Edited
by admin
on Sat Jun 26 06:12:01 UTC 2021
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 [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
Related Record Type Details
LIPID -> FATTY ACID
Values are % of total.
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
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.
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
LIPID -> FATTY ACID
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
U.S produced rice oil. Values are % of composition.
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
LIPID -> FATTY ACID
TURKISH SOURCE
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)
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)
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
varies depending of method of extraction
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.
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
From Cannabis seed oil.
PARENT->INNOVATOR
LIPID -> FATTY ACID
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
Value is % of total fatty acids. Goden VJ, Spensley PC; Oils and Oilseeds, TPI, London, 1971, p.151
PARENT -> CONSTITUENT ALWAYS PRESENT
LIPID -> FATTY ACID
Values given are in undefined precent. Average is typical for U.S. Sunflower oil.
LIPID -> FATTY ACID
Values are % of total.
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY