Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H20O2 |
Molecular Weight | 172.2646 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCC(O)=O
InChI
InChIKey=GHVNFZFCNZKVNT-UHFFFAOYSA-N
InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)
Molecular Formula | C10H20O2 |
Molecular Weight | 172.2646 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Capric acid (decanoic acid) is a medium-chain fatty acid found in saturated fats (cow butter, and plant oils like coconut oil). Capric acid is a major constituent of the MCT ketogenic diet, providing about 40% of the medium chain fat within the diet. The acid is discussed to have positive effect on seizure control through direct AMPA receptor inhibition and on mitochondrial diseases through the binding to PPARgamma. It readily crosses the blood-brain barrier, probably by a combination of diffusion and saturable carrier-mediated transport via a medium-chain fatty acid transporter.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26608744 |
0.43 mM [IC50] | ||
Target ID: P37231|||Q15179 Gene ID: 5468.0 Gene Symbol: PPARG Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27080638 |
41.7 µM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/26608744 |
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Evaluation of insulin permeability and effects of absorption enhancers on its permeability by an in vitro pulmonary epithelial system using Xenopus pulmonary membrane. | 2001 Apr |
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[New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)]. | 2001 Aug |
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Increased vigabatrin entry into the brain by polysorbate 80 and sodium caprate. | 2001 Feb |
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Increased incidence of dyskinesias and other behavioral effects of re-exposure to neuroleptic treatment in social colonies of Cebus apella monkeys. | 2001 Jan |
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Medium-chain fatty acids stimulate interleukin-8 production in Caco-2 cells with different mechanisms from long-chain fatty acids. | 2001 Jul |
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Significance of substrate hydrophobicity for recognition by an oligopeptide transporter (PEPT1). | 2001 Jul-Aug |
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Coupling of fermentation and esterification: microbial esterification of decanoic acid with ethanol produced via fermentation. | 2001 Jun |
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Acute and chronic haloperidol treatments increase parkin mRNA levels in the rat brain. | 2001 Jun 22 |
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Estimation of absorption enhancement by medium-chain fatty acids in rat large intestine. | 2001 Mar-Apr |
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Antifungal activities of pelargonic and capric acid on Microsporum gypseum. | 2001 May |
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A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, designed by prediction of the fluorescence intensity. | 2001 May 15 |
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Mechanistic study into the enhanced transdermal permeation of a model beta-blocker, propranolol, by fatty acids: a melting point depression effect. | 2001 May 21 |
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Lipolytic activity of ricin from Ricinus sanguineus and Ricinus communis on neutral lipids. | 2001 Sep 15 |
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Penetration of engineered antibody fragments into the eye. | 2002 Apr |
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Antioxidant and cyclooxygenase activities of fatty acids found in food. | 2002 Apr 10 |
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Effect of dose of calcium salts of conjugated linoleic acid (CLA) on percentage and fatty acid content of milk fat in midlactation holstein cows. | 2002 Aug |
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The role of the fatty acid beta-oxidation multienzyme complex from Pseudomonas oleovorans in polyhydroxyalkanoate biosynthesis: molecular characterization of the fadBA operon from P. oleovorans and of the enoyl-CoA hydratase genes phaJ from P. oleovorans and Pseudomonas putida. | 2002 Aug |
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Identification of bacteria in drinking and purified water during the monitoring of a typical water purification system. | 2002 Aug 15 |
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Trail pheromone of ponerine ant Gnamptogenys striatula: 4-methylgeranyl esters from Dufour's gland. | 2002 Dec |
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19F-magnetic resonance spectroscopy and chemical shift imaging for schizophrenic patients using haloperidol decanoate. | 2002 Dec |
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Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis. | 2002 Dec |
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Enhancement of paracellular transport of heparin disaccharide across Caco-2 cell monolayers. | 2002 Feb |
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Hydroxylation of fatty acids by microsomal and reconstituted cytochrome P450 2B1. | 2002 Feb 13 |
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The enhancing effect of nasal absorption of FITC-dextran 4,400 by beta-sitosterol beta-D-glucoside in rabbits. | 2002 Feb 19 |
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Nasal glucagon delivery using microcrystalline cellulose in healthy volunteers. | 2002 Feb 21 |
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Preparation and catalytic performance of lipases encapsulated in sol-gel materials. | 2002 Jan |
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Flavor production from edible oils and their constituents by Penicillium corylophilum. | 2002 Jun |
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Evidence in favor of a facilitated transport system for FA uptake in cultured L6 cells. | 2002 Mar |
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Tardive dyskinesia model in the common marmoset. | 2002 Mar |
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Purification and characterization of a novel cholesterol esterase from Pseudomonas aeruginosa, with its application to cleaning lipid-stained contact lenses. | 2002 Nov |
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In vitro evaluation of the release of albuterol sulfate from polymer gels: effect of fatty acids on drug transport across biological membranes. | 2002 Nov |
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Acyl CoA profiles of transgenic plants that accumulate medium-chain fatty acids indicate inefficient storage lipid synthesis in developing oilseeds. | 2002 Nov |
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Haloperidol decanoate doses of 200, 100, or 50 mg/month reduced symptomatic exacerbations more than a 25 mg/month dose in schizophrenia. | 2002 Nov |
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Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid. | 2002 Nov |
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The effect of age on the pharmacological management of ambulatory patients treated with depot neuroleptic medications for schizophrenia and related psychotic disorders. | 2002 Nov |
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Effect of sodium caprate on the intestinal absorption of two modified antisense oligonucleotides in pigs. | 2002 Nov |
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Biochemical evidence against protein-mediated uptake of myristic acid in the bioluminescent marine bacterium Vibrio harveyi. | 2002 Oct |
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[Deterioration of schizoaffective disorder due to an interaction between haloperidol and carbamazepine]. | 2002 Oct 12 |
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Solid-phase microextraction in combination with GC/MS for quantification of the major volatile free fatty acids in ewe cheese. | 2002 Oct 15 |
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Beta-ketoacyl-acyl carrier protein synthase IV: a key enzyme for regulation of medium-chain fatty acid synthesis in Cuphea lanceolata seeds. | 2002 Sep |
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Chicken ghrelin: purification, cDNA cloning, and biological activity. | 2002 Sep |
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Metabolic engineering of Escherichia coli for the production of medium-chain-length polyhydroxyalkanoates rich in specific monomers. | 2002 Sep 10 |
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Computer-aided real-time estimation of reaction conversion for lipase-catalyzed esterification in solvent-free systems. | 2002 Sep 30 |
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Gastric emptying in rats following administration of a range of different fats measured as acetaminophen concentration in plasma. | 2003 |
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A new Escherichia coli metabolic competency: growth on fatty acids by a novel anaerobic beta-oxidation pathway. | 2003 Feb |
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Medium- versus long-chain triglycerides for 27 days increases fat oxidation and energy expenditure without resulting in changes in body composition in overweight women. | 2003 Jan |
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Plasma fatty acids and [13C]linoleic acid metabolism in preterm infants fed a formula with medium-chain triglycerides. | 2003 Jan |
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The relationship between dopamine D2 receptor occupancy and the vacuous chewing movement syndrome in rats. | 2003 Jan |
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Triacylglycerols determine the unusual storage physiology of Cuphea seed. | 2003 Sep |
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Synthesis of monocaprin catalyzed by lipase. | 2003 Spring |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26912516
The oral minimal dose is 1723 mg/kg (animal model).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23177536
In a seizure model, rat cortex-hippocampus slices were incubated with 100 uM and 1 mM of capric acid. The fatty acid was found to reduce the frequency of epileptiform discharges at these conentrations.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:40:56 UTC 2023
by
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on
Wed Jul 05 22:40:56 UTC 2023
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Record UNII |
4G9EDB6V73
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Record Status |
Validated (UNII)
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Record Version |
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CFR |
21 CFR 172.860
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DSLD |
2486 (Number of products:70)
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NCI_THESAURUS |
C68421
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JECFA EVALUATION |
DECANOIC ACID
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EPA PESTICIDE CODE |
128955
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NCI_THESAURUS |
C68391
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M3030
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334-48-5
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5025
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C031071
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4G9EDB6V73
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DECANOIC ACID
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100000135492
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4G9EDB6V73
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44499
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206-376-4
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22380
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DB03600
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2969
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SUB70871
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DTXSID9021554
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2751
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30813
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C68329
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Related Record | Type | Details | ||
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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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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
USP
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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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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SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |