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Details

Stereochemistry ACHIRAL
Molecular Formula C18H31O2.Na
Molecular Weight 302.4273
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of SODIUM LINOLEATE

SMILES

[Na+].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O

InChI

InChIKey=WYPBVHPKMJYUEO-NBTZWHCOSA-M
InChI=1S/C18H32O2.Na/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);/q;+1/p-1/b7-6-,10-9-;

HIDE SMILES / InChI

Molecular Formula C18H31O2
Molecular Weight 279.4375
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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

8.392896E11
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Fatty acids and derivatives as antimicrobial agents.
1972 Jul
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
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
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
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
2000 Jun 20
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 both enhances activation and blocks Kv1.5 and Kv2.1 channels by two separate mechanisms.
2001 Oct
Changes in matrix proteoglycans induced by insulin and fatty acids in hepatic cells may contribute to dyslipidemia of insulin resistance.
2001 Sep
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
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
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
Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro.
2004 Oct
Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity.
2005 Oct
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
Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha.
2008 Mar
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
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 Thu Jul 06 01:50:50 UTC 2023
Edited
by admin
on Thu Jul 06 01:50:50 UTC 2023
Record UNII
872C9A1W9I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM LINOLEATE
INCI  
INCI  
Official Name English
PRISAVON L
Brand Name English
LINOLEIC ACID, SODIUM SALT
Common Name English
9,12-OCTADECADIENOIC ACID, SODIUM SALT
Common Name English
SODIUM LINOLEATE [INCI]
Common Name English
Code System Code Type Description
CAS
822-17-3
Created by admin on Thu Jul 06 01:50:51 UTC 2023 , Edited by admin on Thu Jul 06 01:50:51 UTC 2023
PRIMARY
FDA UNII
872C9A1W9I
Created by admin on Thu Jul 06 01:50:51 UTC 2023 , Edited by admin on Thu Jul 06 01:50:51 UTC 2023
PRIMARY
DRUG BANK
DBSALT002734
Created by admin on Thu Jul 06 01:50:51 UTC 2023 , Edited by admin on Thu Jul 06 01:50:51 UTC 2023
PRIMARY
PUBCHEM
23676150
Created by admin on Thu Jul 06 01:50:51 UTC 2023 , Edited by admin on Thu Jul 06 01:50:51 UTC 2023
PRIMARY
EPA CompTox
DTXSID5041562
Created by admin on Thu Jul 06 01:50:51 UTC 2023 , Edited by admin on Thu Jul 06 01:50:51 UTC 2023
PRIMARY
DAILYMED
872C9A1W9I
Created by admin on Thu Jul 06 01:50:51 UTC 2023 , Edited by admin on Thu Jul 06 01:50:51 UTC 2023
PRIMARY
RXCUI
2471869
Created by admin on Thu Jul 06 01:50:51 UTC 2023 , Edited by admin on Thu Jul 06 01:50:51 UTC 2023
PRIMARY
ECHA (EC/EINECS)
212-491-0
Created by admin on Thu Jul 06 01:50:51 UTC 2023 , Edited by admin on Thu Jul 06 01:50:51 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE