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 Date1996 |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
|
| 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 |
|
| Lipid peroxides induce expression of catalase in cultured vascular cells. | 2000 Aug |
|
| 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 |
|
| 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 |
|
| Linoleic acid, other fatty acids, and the risk of stroke. | 2002 Aug |
|
| Arachidonic and linoleic acid metabolism in mouse intestinal tissue: evidence for novel lipoxygenase activity. | 2002 Feb 1 |
|
| 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 |
|
| Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts. | 2003 Aug 30 |
|
| 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 |
|
| Binding analyses between Human PPARgamma-LBD and ligands. | 2004 Jan |
|
| Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. | 2004 Oct |
|
| Expression of cFABP and PPAR in trophoblast cells: effect of PPAR ligands on linoleic acid uptake and differentiation. | 2005 Feb 21 |
|
| Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. | 2005 Oct |
|
| Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway. | 2005 Oct 28 |
|
| Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification. | 2006 Jul |
|
| Role of FoxO1 in FFA-induced oxidative stress in adipocytes. | 2007 Jul |
|
| Comprehensive analysis of the effects of ordinary nutrients on hepatitis C virus RNA replication in cell culture. | 2007 Jun |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Bezafibrate mildly stimulates ketogenesis and fatty acid metabolism in hypertriglyceridemic subjects. | 2010 Jul |
|
| TGF-β-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury. | 2012 Dec |
|
| 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 |
|
| Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach. | 2014 Jul |
|
| Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets. | 2015 Sep 18 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:38:49 GMT 2023
by
admin
on
Fri Dec 15 18:38:49 GMT 2023
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| Record UNII |
872C9A1W9I
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| Record Status |
Validated (UNII)
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| Record Version |
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822-17-3
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872C9A1W9I
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DBSALT002734
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23676150
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DTXSID5041562
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872C9A1W9I
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2471869
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212-491-0
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE |
