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
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-;
| 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.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0008283 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | Intralipid Approved UseIntralipid® 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 Date8.392896E11 |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 01:50:50 UTC 2023
by
admin
on
Thu Jul 06 01:50:50 UTC 2023
|
| Record UNII |
872C9A1W9I
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Official Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 |
