Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H31O2.H4N |
| Molecular Weight | 297.476 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[NH4+].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O
InChI
InChIKey=KQLYFVFFPVJGRM-NBTZWHCOSA-N
InChI=1S/C18H32O2.H3N/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);1H3/b7-6-,10-9-;
| Molecular Formula | H3N |
| Molecular Weight | 17.0305 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| 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.
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 |
|---|---|---|
| Fatty acids and derivatives as antimicrobial agents. | 1972 Jul |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Binding of prostaglandins to human PPARgamma: tool assessment and new natural ligands. | 2001 Apr 6 |
|
| Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates. | 2001 Jan 15 |
|
| 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 |
|
| Topical peroxisome proliferator activated receptor-alpha activators reduce inflammation in irritant and allergic contact dermatitis models. | 2002 Jan |
|
| 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 |
|
| Quercetin protects against linoleic acid-induced porcine endothelial cell dysfunction. | 2004 Apr |
|
| Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004 Dec |
|
| Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. | 2004 Oct |
|
| Omega-3 fatty acids inhibit an increase of proinflammatory cytokines in patients with active Crohn's disease compared with omega-6 fatty acids. | 2005 Dec |
|
| 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 |
|
| The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. | 2006 Nov 25 |
|
| 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 |
|
| Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element. | 2007 Mar |
|
| Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha. | 2008 Mar |
|
| 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 |
|
| 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 |
|
| Regulation of stearoyl-coenzyme A desaturase and fatty acid delta-6 desaturase-2 expression by linoleic acid and arachidonic acid in human sebocytes leads to enhancement of proinflammatory activity but does not affect lipogenesis. | 2011 Aug |
|
| A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
|
| 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 |
|
| 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 |
|
| Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells. | 2012 Sep |
|
| 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 |
|
| Bongkrekic acid as a selective activator of the peroxisome proliferator-activated receptor γ (PPARγ) isoform. | 2015 Apr |
|
| 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 19:09:13 GMT 2023
by
admin
on
Fri Dec 15 19:09:13 GMT 2023
|
| Record UNII |
H9ODY63839
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
7721-14-4
Created by
admin on Fri Dec 15 19:09:13 GMT 2023 , Edited by admin on Fri Dec 15 19:09:13 GMT 2023
|
PRIMARY | |||
|
H9ODY63839
Created by
admin on Fri Dec 15 19:09:13 GMT 2023 , Edited by admin on Fri Dec 15 19:09:13 GMT 2023
|
PRIMARY | |||
|
231-757-7
Created by
admin on Fri Dec 15 19:09:13 GMT 2023 , Edited by admin on Fri Dec 15 19:09:13 GMT 2023
|
PRIMARY | |||
|
6441307
Created by
admin on Fri Dec 15 19:09:13 GMT 2023 , Edited by admin on Fri Dec 15 19:09:13 GMT 2023
|
PRIMARY | |||
|
DTXSID201340285
Created by
admin on Fri Dec 15 19:09:13 GMT 2023 , Edited by admin on Fri Dec 15 19:09:13 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
