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 |
|---|---|---|
| Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets. | 2015-09-18 |
|
| Bongkrekic acid as a selective activator of the peroxisome proliferator-activated receptor γ (PPARγ) isoform. | 2015-04 |
|
| Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach. | 2014-07 |
|
| Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice. | 2013-07-05 |
|
| 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. | 2013-05 |
|
| TGF-β-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury. | 2012-12 |
|
| New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors. | 2012-11 |
|
| 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. | 2012-10 |
|
| Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells. | 2012-09 |
|
| A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
|
| 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. | 2011-08 |
|
| Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms. | 2010-08 |
|
| Bezafibrate mildly stimulates ketogenesis and fatty acid metabolism in hypertriglyceridemic subjects. | 2010-07 |
|
| 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 |
|
| Role of polyunsaturated fatty acids in the management of Egyptian children with autism. | 2008-09 |
|
| Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus. | 2008-09 |
|
| 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. | 2008-07-30 |
|
| Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids. | 2008-07 |
|
| A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine. | 2008-05 |
|
| Changing ratios of omega-6 to omega-3 fatty acids can differentially modulate polychlorinated biphenyl toxicity in endothelial cells. | 2008-03-10 |
|
| Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha. | 2008-03 |
|
| Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes. | 2008-01 |
|
| Role of FoxO1 in FFA-induced oxidative stress in adipocytes. | 2007-07 |
|
| Comprehensive analysis of the effects of ordinary nutrients on hepatitis C virus RNA replication in cell culture. | 2007-06 |
|
| Unsaturated fatty acids suppress the expression of the ATP-binding cassette transporter G1 (ABCG1) and ABCA1 genes via an LXR/RXR responsive element. | 2007-03 |
|
| Cyclooxygenase-2 promoter activation by the aromatic hydrocarbon receptor in breast cancer mcf-7 cells: repressive effects of conjugated linoleic acid. | 2007 |
|
| The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. | 2006-11-25 |
|
| High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids? | 2006-08 |
|
| Differential activation of nuclear receptors by perfluorinated fatty acid analogs and natural fatty acids: a comparison of human, mouse, and rat peroxisome proliferator-activated receptor-alpha, -beta, and -gamma, liver X receptor-beta, and retinoid X receptor-alpha. | 2006-08 |
|
| Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules. | 2006-07 |
|
| Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification. | 2006-07 |
|
| Omega-3 fatty acids inhibit an increase of proinflammatory cytokines in patients with active Crohn's disease compared with omega-6 fatty acids. | 2005-12 |
|
| Specificity of receptor-ligand interactions and their effect on dimerisation as observed by electrospray mass spectrometry: bile acids form stable adducts to the RXRalpha. | 2005-11 |
|
| Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway. | 2005-10-28 |
|
| Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. | 2005-10 |
|
| Expression of cFABP and PPAR in trophoblast cells: effect of PPAR ligands on linoleic acid uptake and differentiation. | 2005-02-21 |
|
| Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004-12 |
|
| Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. | 2004-10 |
|
| Quercetin protects against linoleic acid-induced porcine endothelial cell dysfunction. | 2004-04 |
|
| In Vivo Studies of the Biosynthesis of [alpha]-Eleostearic Acid in the Seed of Momordica charantia L. | 1997-04 |
|
| Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes. | 1995-12-01 |
|
| 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. | 1994-09-30 |
|
| 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. | 1994-07 |
|
| 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. | 1994-02-10 |
|
| Physiology and pathophysiology of organic acids in cerebrospinal fluid. | 1993 |
|
| Screening for new compounds with antiherpes activity. | 1984-10 |
|
| Interaction of polyunsaturated fatty acids with animal cells and enveloped viruses. | 1980-12 |
|
| Cerebrospinal fluid lipids in demyelinating disease. II. Linoleic acid as an index of impaired blood-CSF barrier. | 1980-01 |
|
| Fatty acids and derivatives as antimicrobial agents. | 1972-07 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:33:47 GMT 2025
by
admin
on
Mon Mar 31 19:33:47 GMT 2025
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| Record UNII |
H9ODY63839
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| Record Status |
Validated (UNII)
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| Record Version |
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7721-14-4
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H9ODY63839
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231-757-7
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6441307
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DTXSID201340285
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PARENT -> SALT/SOLVATE |
