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 | C18H32O2 |
| Molecular Weight | 280.4455 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 2 |
| Optical Activity | NONE |
| 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 |
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 |
|
| 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 |
|
| Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions. | 2000 Jun 20 |
|
| Changes in matrix proteoglycans induced by insulin and fatty acids in hepatic cells may contribute to dyslipidemia of insulin resistance. | 2001 Sep |
|
| 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 |
|
| 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 |
|
| Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004 Dec |
|
| 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 |
|
| Sesquiterpenes from Warburgia ugandensis and their antimycobacterial activity. | 2005 Oct |
|
| Cyclooxygenase-2 promoter activation by the aromatic hydrocarbon receptor in breast cancer mcf-7 cells: repressive effects of conjugated linoleic acid. | 2007 |
|
| Comprehensive analysis of the effects of ordinary nutrients on hepatitis C virus RNA replication in cell culture. | 2007 Jun |
|
| Characterization of Madin-Darby bovine kidney cell line for peroxisome proliferator-activated receptors: temporal response and sensitivity to fatty acids. | 2008 Jul |
|
| Sex hormone influence on hepatitis in young male A/JCr mice infected with Helicobacter hepaticus. | 2008 Sep |
|
| Antimicrobial activity of n-6, n-7 and n-9 fatty acids and their esters for oral microorganisms. | 2010 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 |
|
| Exposure to DEHP decreased four fatty acid levels in plasma of prepartum mice. | 2013 Jul 5 |
|
| 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
Thu Jul 06 02:17:27 UTC 2023
by
admin
on
Thu Jul 06 02:17:27 UTC 2023
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| Record UNII |
H9ODY63839
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| Record Status |
Validated (UNII)
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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 |
