Details
Stereochemistry | ACHIRAL |
Molecular Formula | C18H32O2 |
Molecular Weight | 280.4462 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC/C(/[H])=C(/[H])\C/C(/[H])=C(/[H])\CCCCCCCC(=O)O
InChI
InChIKey=OYHQOLUKZRVURQ-HZJYTTRNSA-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-
Molecular Formula | C18H32O2 |
Molecular Weight | 280.4462 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Optical Activity | NONE |
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: GO:0008283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23341188 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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 |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Cerebrospinal fluid lipids in demyelinating disease. II. Linoleic acid as an index of impaired blood-CSF barrier. | 1980 Jan |
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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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Evidence for direct binding of fatty acids and eicosanoids to human peroxisome proliferators-activated receptor alpha. | 1999 Jul 14 |
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Plasma saturated and linoleic fatty acids are independently associated with blood pressure. | 1999 Sep |
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Zinc protects against apoptosis of endothelial cells induced by linoleic acid and tumor necrosis factor alpha. | 2000 Jan |
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Long-chain fatty acids regulate liver carnitine palmitoyltransferase I gene (L-CPT I) expression through a peroxisome-proliferator-activated receptor alpha (PPARalpha)-independent pathway. | 2001 Feb 15 |
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Abundant expression of uncoupling protein-2 in the small intestine: up-regulation by dietary fish oil and fibrates. | 2001 Jan 15 |
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Linoleic acid, other fatty acids, and the risk of stroke. | 2002 Aug |
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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 |
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Divergent effects of selective peroxisome proliferator-activated receptor-gamma 2 ligands on adipocyte versus osteoblast differentiation. | 2002 Jun |
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Polyunsaturated fatty acid status and relapse vulnerability in cocaine addicts. | 2003 Aug 30 |
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PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation. | 2003 Feb |
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A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs. | 2003 Feb 7 |
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Linoleic acid supplementation of Barth syndrome fibroblasts restores cardiolipin levels: implications for treatment. | 2003 Mar |
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Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40. | 2003 Mar 13 |
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The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids. | 2003 Mar 28 |
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Beneficial effect of oleoylated lipids on paraoxonase 1: protection against oxidative inactivation and stabilization. | 2003 Oct 15 |
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Preferential inhibition of paraoxonase activity of human paraoxonase 1 by negatively charged lipids. | 2004 Dec |
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Dietary alpha-linolenic acid reduces COX-2 expression and induces apoptosis of hepatoma cells. | 2004 Feb |
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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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High-fat feeding reduces endothelium-dependent vasodilation in rats: differential mechanisms for saturated and unsaturated fatty acids? | 2006 Aug |
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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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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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TGF-β-SMAD3 signaling mediates hepatic bile acid and phospholipid metabolism following lithocholic acid-induced liver injury. | 2012 Dec |
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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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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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.clinicaltrials.gov/ct2/show/NCT00638196
Linoleic acid emulsion is administered at a dose of 30 g two times daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4856264
Lymphocytes from patients with multiple sclerosis were incubated with linoleic acid at concnetration of 0.08 mg/ml and the inhibition achieved 91%.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Jun 26 06:12:01 UTC 2021
by
admin
on
Sat Jun 26 06:12:01 UTC 2021
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Record UNII |
9KJL21T0QJ
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C68398
Created by
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LOINC |
35165-0
Created by
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LOINC |
2564-3
Created by
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LOINC |
90917-6
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LOINC |
75117-2
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NCI_THESAURUS |
C2563
Created by
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CFR |
21 CFR 357.210
Created by
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CFR |
21 CFR 184.1065
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LOINC |
90915-0
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LOINC |
47686-1
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DSLD |
1537 (Number of products:578)
Created by
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Code System | Code | Type | Description | ||
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LINOLEIC ACID
Created by
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PRIMARY | |||
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5200
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PRIMARY | |||
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D019787
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PRIMARY | |||
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9KJL21T0QJ
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PRIMARY | |||
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60-33-3
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PRIMARY | |||
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3323
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PRIMARY | |||
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DB14104
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PRIMARY | |||
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M6830
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PRIMARY | Merck Index | ||
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C615
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5280450
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6400
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200-470-9
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70611
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ALTERNATIVE | |||
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60-33-3
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PRIMARY | |||
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SUB14359MIG
Created by
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PRIMARY |
Related Record | Type | Details | ||
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LIPID -> FATTY ACID |
Values are % of total.
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID |
JB Rossell and co-workers; JAOCS62(2), 221-230(1985).
Range weight is a mean.
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LIPID -> FATTY ACID |
Value is % of composition.
Oleic safflower variety UC-1 cited by Knowles, P, Calif. Agr. 19(12),15(1965), produced 15.00% by composition.
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for US corn oil w/std. deviation of 1.20%
LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
U.S produced rice oil. Values are % of composition.
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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LIPID -> FATTY ACID |
TURKISH SOURCE
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LIPID -> FATTY ACID |
Values are % of weight of fatty acid composition.
O?Connor, RT, Herb, SF; J Am Oil Chem Soc 47, 186A, 195A, 197A(1970)(range)
Brignoli, CA et al: J Am Diet Assoc 68, 224(1976)(average)
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Value is fatty acid composition (%) for international corn oil w/std. deviation of 2.4%
LR Strecker, et al; Proc World Conf Edible Fats & Oils Proc, Amer Oil Chem Soc, pp-309-323(1990)
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LIPID -> FATTY ACID |
G Jurriens and ACJ Kroesen, J Am Oil Chem Soc, 42(9)(1965)(average value).
Range values as of FAO/WHO Codex Alimentarius Committee on commercial fats and oils.(unspecified percent)
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
varies depending of method of extraction
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PARENT -> CONSTITUENT ALWAYS PRESENT |
Compound measured as 2.50% of the composition of the steam distillate of Elymus repens rhizome as per R Boesel in Planta Medica iss:4 pg:399-400, 1989.
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
From Cannabis seed oil.
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PARENT->INNOVATOR | |||
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LIPID -> FATTY ACID |
USP
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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LIPID -> FATTY ACID |
Value is % of total fatty acids.
Goden VJ, Spensley PC; Oils and Oilseeds, TPI, London, 1971, p.151
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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LIPID -> FATTY ACID |
Values given are in undefined precent.
Average is typical for U.S. Sunflower oil.
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LIPID -> FATTY ACID |
Values are % of total.
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |