Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H32O2 |
| Molecular Weight | 280.4455 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC\C=C\C\C=C\CCCCCCCC(O)=O
InChI
InChIKey=OYHQOLUKZRVURQ-AVQMFFATSA-N
InChI=1S/C18H32O2/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)/b7-6+,10-9+
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 |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Fatty acids and derivatives as antimicrobial agents. | 1972 Jul |
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| Screening for new compounds with antiherpes activity. | 1984 Oct |
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| Physiology and pathophysiology of organic acids in cerebrospinal fluid. | 1993 |
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| 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 |
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| 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 |
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| 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 |
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| Fatty acids and fibrates are potent inducers of transcription of the phosphenolpyruvate carboxykinase gene in adipocytes. | 1995 Dec 1 |
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| In Vivo Studies of the Biosynthesis of [alpha]-Eleostearic Acid in the Seed of Momordica charantia L. | 1997 Apr |
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| Protective action of CLA against oxidative inactivation of paraoxonase 1, an antioxidant enzyme. | 2003 Jun |
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| Zinc modulates PPARgamma signaling and activation of porcine endothelial cells. | 2003 Oct |
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| Quercetin protects against linoleic acid-induced porcine endothelial cell dysfunction. | 2004 Apr |
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| Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004 Dec |
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| Binding analyses between Human PPARgamma-LBD and ligands. | 2004 Jan |
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| Peroxisome proliferator-activated receptor and farnesoid X receptor ligands differentially regulate sebaceous differentiation in human sebaceous gland organ cultures in vitro. | 2004 Oct |
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| 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 |
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| Expression of cFABP and PPAR in trophoblast cells: effect of PPAR ligands on linoleic acid uptake and differentiation. | 2005 Feb 21 |
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| 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 Nov |
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| Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. | 2005 Oct |
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| Unsaturated fatty acids phosphorylate and destabilize ABCA1 through a phospholipase D2 pathway. | 2005 Oct 28 |
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| High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids? | 2006 Aug |
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| 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 Aug |
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| Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules. | 2006 Jul |
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| Formation of Nepsilon-(succinyl)lysine in vivo: a novel marker for docosahexaenoic acid-derived protein modification. | 2006 Jul |
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| The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. | 2006 Nov 25 |
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| Cyclooxygenase-2 promoter activation by the aromatic hydrocarbon receptor in breast cancer mcf-7 cells: repressive effects of conjugated linoleic acid. | 2007 |
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| Role of FoxO1 in FFA-induced oxidative stress in adipocytes. | 2007 Jul |
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| Comprehensive analysis of the effects of ordinary nutrients on hepatitis C virus RNA replication in cell culture. | 2007 Jun |
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| 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 |
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| Differential effects of long-chain fatty acids and clofibrate on gene expression profiles in cardiomyocytes. | 2008 Jan |
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| Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids. | 2008 Jul |
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| 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 Jul 30 |
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| Down-regulation of alpha-amino-beta-carboxymuconate-epsilon-semialdehyde decarboxylase by polyunsaturated fatty acids in hepatocytes is not mediated by PPARalpha. | 2008 Mar |
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| Changing ratios of omega-6 to omega-3 fatty acids can differentially modulate polychlorinated biphenyl toxicity in endothelial cells. | 2008 Mar 10 |
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| A cholesterol-free, high-fat diet suppresses gene expression of cholesterol transporters in murine small intestine. | 2008 May |
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| Role of polyunsaturated fatty acids in the management of Egyptian children with autism. | 2008 Sep |
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| Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus. | 2008 Sep |
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| Identification of an endogenous ligand bound to a native orphan nuclear receptor. | 2009 |
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| Optimization of an enzyme-linked immunosorbent assay to screen ligand of Peroxisome proliferator-activated receptor alpha. | 2009 |
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| Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms. | 2010 Aug |
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| Bezafibrate mildly stimulates ketogenesis and fatty acid metabolism in hypertriglyceridemic subjects. | 2010 Jul |
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| 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 |
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| A cardiac-specific robotized cellular assay identified families of human ligands as inducers of PGC-1α expression and mitochondrial biogenesis. | 2012 |
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| TGF-β-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury. | 2012 Dec |
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| New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors. | 2012 Nov |
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| 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 |
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| Effects of palmitic acid on TNF-α-induced cytotoxicity in SK-Hep-1 cells. | 2012 Sep |
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| Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice. | 2013 Jul 5 |
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| Phthalates efficiently bind to human peroxisome proliferator activated receptor and retinoid X receptor α, β, γ subtypes: an in silico approach. | 2014 Jul |
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| Bongkrekic acid as a selective activator of the peroxisome proliferator-activated receptor γ (PPARγ) isoform. | 2015 Apr |
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| Excess Linoleic Acid Increases Collagen I/III Ratio and "Stiffens" the Heart Muscle Following High Fat Diets. | 2015 Sep 18 |
Patents
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7552P0K6PN
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5282457
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Linolelaidic acid
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506-21-8
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DTXSID50897508
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SUBSTANCE RECORD
