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Details

Stereochemistry ACHIRAL
Molecular Formula C10H19O2.Na
Molecular Weight 194.2464
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM CAPRATE

SMILES

[Na+].CCCCCCCCCC([O-])=O

InChI

InChIKey=FIWQZURFGYXCEO-UHFFFAOYSA-M
InChI=1S/C10H20O2.Na/c1-2-3-4-5-6-7-8-9-10(11)12;/h2-9H2,1H3,(H,11,12);/q;+1/p-1

HIDE SMILES / InChI
Molecular Formula C10H19O2
Molecular Weight 171.2567
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

1968
62
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 0.43 mM [IC50]
Peroxisome proliferator-activated receptor gamma
111
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
Modulator
828
 41.7 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effects of medium-chain fatty acids on intracellular calcium levels and the cytoskeleton in human intestinal (Caco-2) cell monolayers.
2001 Apr
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
In vivo absorption of medium-chain fatty acids by the rat colon exceeds that of short-chain fatty acids.
2001 Apr
Activity of different Candida antarctica lipase B formulations in organic solvents.
2001 Apr 20
Structural basis of non-specific lipid binding in maize lipid-transfer protein complexes revealed by high-resolution X-ray crystallography.
2001 Apr 27
[New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)].
2001 Aug
Biosynthesis of acaterin: coupling of C(5) unit with octanoate.
2001 Aug 24
Increased vigabatrin entry into the brain by polysorbate 80 and sodium caprate.
2001 Feb
Increased incidence of dyskinesias and other behavioral effects of re-exposure to neuroleptic treatment in social colonies of Cebus apella monkeys.
2001 Jan
Addition of hydrophilic and lipophilic compounds of biological relevance to the monoolein/water system. I. Phase behavior.
2001 Jan
Decreased choline acetyltransferase immunoreactivity in discrete striatal subregions following chronic haloperidol in rats.
2001 Jan
Medium-chain fatty acids stimulate interleukin-8 production in Caco-2 cells with different mechanisms from long-chain fatty acids.
2001 Jul
Coupling of fermentation and esterification: microbial esterification of decanoic acid with ethanol produced via fermentation.
2001 Jun
Acute and chronic haloperidol treatments increase parkin mRNA levels in the rat brain.
2001 Jun 22
Antipsychotic prescription use and costs for persons with schizophrenia in the 1990s: current trends and five year time series forecasts.
2001 Mar 1
Computer-aided control of water activity for lipase-catalyzed esterification in solvent-free systems.
2001 Mar-Apr
D2 but not D3 receptors are elevated after 9 or 11 months chronic haloperidol treatment: influence of withdrawal period.
2001 May
A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, designed by prediction of the fluorescence intensity.
2001 May 15
Bullfrog ghrelin is modified by n-octanoic acid at its third threonine residue.
2001 Nov 2
Effect of chronic treatment with haloperidol on vasopressin release and behavioral changes by osmotic stimulation of the supraoptic nucleus.
2001 Sep 21
Prolonged anti-inflammatory action of DL-lactide/glycolide copolymer nanospheres containing betamethasone sodium phosphate for an intra-articular delivery system in antigen-induced arthritic rabbit.
2002 Apr
The influence of caprate on rectal absorption of phenoxymethylpenicillin: experience from an in-vivo perfusion in humans.
2002 Apr
Penetration of engineered antibody fragments into the eye.
2002 Apr
Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length.
2002 Apr
PCR cloning of polyhydroxyalkanoate biosynthesis genes from Burkholderia caryophylli and their functional expression in recombinant Escherichia coli.
2002 Apr 23
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
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
19F-magnetic resonance spectroscopy and chemical shift imaging for schizophrenic patients using haloperidol decanoate.
2002 Dec
Enhancement of paracellular transport of heparin disaccharide across Caco-2 cell monolayers.
2002 Feb
Palmitate-induced cardiac apoptosis is mediated through CPT-1 but not influenced by glucose and insulin.
2002 Feb
The enhancing effect of nasal absorption of FITC-dextran 4,400 by beta-sitosterol beta-D-glucoside in rabbits.
2002 Feb 19
Preparation and catalytic performance of lipases encapsulated in sol-gel materials.
2002 Jan
Fluphenazine plasma level monitoring for patients receiving fluphenazine decanoate.
2002 Jan 1
Effect of fatty acid chain length on initial reaction rates and regioselectivity of lipase-catalysed esterification of disaccharides.
2002 Jul 16
Suppressive effect of saturated acyl L-ascorbate on the oxidation of linoleic acid encapsulated with maltodextrin or gum arabic by spray-drying.
2002 Jul 3
Evidence in favor of a facilitated transport system for FA uptake in cultured L6 cells.
2002 Mar
Tardive dyskinesia model in the common marmoset.
2002 Mar
Haloperidol decanoate doses of 200, 100, or 50 mg/month reduced symptomatic exacerbations more than a 25 mg/month dose in schizophrenia.
2002 Nov
Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid.
2002 Nov
Effect of sodium caprate on the intestinal absorption of two modified antisense oligonucleotides in pigs.
2002 Nov
Biochemical evidence against protein-mediated uptake of myristic acid in the bioluminescent marine bacterium Vibrio harveyi.
2002 Oct
Solid-phase microextraction in combination with GC/MS for quantification of the major volatile free fatty acids in ewe cheese.
2002 Oct 15
Beta-ketoacyl-acyl carrier protein synthase IV: a key enzyme for regulation of medium-chain fatty acid synthesis in Cuphea lanceolata seeds.
2002 Sep
Metabolic engineering of Escherichia coli for the production of medium-chain-length polyhydroxyalkanoates rich in specific monomers.
2002 Sep 10
Intramuscular preparations of antipsychotics: uses and relevance in clinical practice.
2003
Combinatorial use of sodium laurate with taurine or L-glutamine enhances colonic absorption of rebamipide, poorly absorbable antiulcer drug, without any serious histopathological mucosal damages.
2003 Apr
Research on psychological testing supervision using the Holloway (1995) method: a critique of DeCato (2002).
2003 Feb
Enhancement of adenovirus-mediated gene transfer to the airways by DEAE dextran and sodium caprate in vivo.
2003 Jan
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
The effect of conjugated linoleic acid and medium-chain fatty acids on transepithelial calcium transport in human intestinal-like Caco-2 cells.
2003 May
Patents

Patents

04003749
2
04009039
2
04076534
2
04609650
17
04935444
2
05676925
4
05998433
6
06166265
2
06685908
3
07404964
2
07605123
3
07705169
2
07872095
5
08563685
2
08642652
3
JP2000336383A
2
JP2000514095A
2
JP2002537321A
7
JP2004525957A
2
JP2004537516A
4
JP2005270101A
2
JP2005517752A
4
JP2006089496A
2
JP2006516987A
4
JP2009522400A
3
JP2010116487A
2
JP2011506492A
5
JP3585245B2
3
JP4327604B2
4
JP4690404B2
11
JPH01206510A
2
JPH01256343A
2
JPH02268659A
3
JPH03119108A
2
JPH05123194A
2
JPH05156075A
2
JPH05279775A
2
JPH0549410A
2
JPH0556751A
2
JPH06211606A
2
JPH06228403A
2
JPH07123919A
2
JPH07135943A
2
JPH07277983A
2
JPH07277984A
2
JPH07305014A
2
JPH08154576A
2
JPH08295744A
5
JPH0995468A
2
JPH10194935A
2
JPH10226650A
2
JPH10295272A
2
JPH10295347A
2
JPH11246439A
2
JPS55144022A
2
JPS5795997A
2
JPS58134145A
2
JPS60244524A
2
JPS63218750A
2

Sample Use Guides

In Vivo Use Guide
The oral minimal dose is 1723 mg/kg (animal model).
Route of Administration: Oral
In Vitro Use Guide
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 Fri Dec 15 18:38:44 GMT 2023
Edited
by admin
on Fri Dec 15 18:38:44 GMT 2023
Record UNII
4I820XKV2A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM CAPRATE
INCI  
INCI  
Official Name English
SODIUM DECANOATE
Systematic Name English
CAPRIC ACID, SODIUM SALT
Common Name English
DECANOIC ACID, SODIUM SALT
Common Name English
CAPRIC ACID SODIUM SALT
Common Name English
SODIUM CAPRATE [INCI]
Common Name English
Code System Code Type Description
EVMPD
SUB69937
Created by admin on Fri Dec 15 18:38:44 GMT 2023 , Edited by admin on Fri Dec 15 18:38:44 GMT 2023
PRIMARY
FDA UNII
4I820XKV2A
Created by admin on Fri Dec 15 18:38:44 GMT 2023 , Edited by admin on Fri Dec 15 18:38:44 GMT 2023
PRIMARY
MESH
C031071
Created by admin on Fri Dec 15 18:38:44 GMT 2023 , Edited by admin on Fri Dec 15 18:38:44 GMT 2023
PRIMARY
SMS_ID
100000135236
Created by admin on Fri Dec 15 18:38:44 GMT 2023 , Edited by admin on Fri Dec 15 18:38:44 GMT 2023
PRIMARY
PUBCHEM
4457968
Created by admin on Fri Dec 15 18:38:44 GMT 2023 , Edited by admin on Fri Dec 15 18:38:44 GMT 2023
PRIMARY
CAS
1002-62-6
Created by admin on Fri Dec 15 18:38:44 GMT 2023 , Edited by admin on Fri Dec 15 18:38:44 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-688-4
Created by admin on Fri Dec 15 18:38:44 GMT 2023 , Edited by admin on Fri Dec 15 18:38:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID0027351
Created by admin on Fri Dec 15 18:38:44 GMT 2023 , Edited by admin on Fri Dec 15 18:38:44 GMT 2023
PRIMARY
Related Record Type Details
Structure of CAPRIC ACID
PARENT -> SALT/SOLVATE
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