U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H20O2
Molecular Weight 172.265
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CAPRIC ACID

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)

HIDE SMILES / InChI

Molecular Formula C10H20O2
Molecular Weight 172.265
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.43 mM [IC50]
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
41.7 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Antipsychotic prescribing practices in Connecticut's public mental health system: rates of changing medications and prescribing styles.
2002
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
Kinetic analysis of hydroxylation of saturated fatty acids by recombinant P450foxy produced by an Escherichia coli expression system.
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
Identification of bacteria in drinking and purified water during the monitoring of a typical water purification system.
2002 Aug 15
Trail pheromone of ponerine ant Gnamptogenys striatula: 4-methylgeranyl esters from Dufour's gland.
2002 Dec
19F-magnetic resonance spectroscopy and chemical shift imaging for schizophrenic patients using haloperidol decanoate.
2002 Dec
Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis.
2002 Dec
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
Flavor production from edible oils and their constituents by Penicillium corylophilum.
2002 Jun
Comparison of effects of khat extract and amphetamine on motor behaviors in mice.
2002 Jun
Simultaneous production of polyhydroxyalkanoates and rhamnolipids by Pseudomonas aeruginosa.
2002 Jun 20
Purification and characterization of a novel cholesterol esterase from Pseudomonas aeruginosa, with its application to cleaning lipid-stained contact lenses.
2002 Nov
In vitro evaluation of the release of albuterol sulfate from polymer gels: effect of fatty acids on drug transport across biological membranes.
2002 Nov
Acyl CoA profiles of transgenic plants that accumulate medium-chain fatty acids indicate inefficient storage lipid synthesis in developing oilseeds.
2002 Nov
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
The effect of age on the pharmacological management of ambulatory patients treated with depot neuroleptic medications for schizophrenia and related psychotic disorders.
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
[Deterioration of schizoaffective disorder due to an interaction between haloperidol and carbamazepine].
2002 Oct 12
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
Chicken ghrelin: purification, cDNA cloning, and biological activity.
2002 Sep
Metabolic engineering of Escherichia coli for the production of medium-chain-length polyhydroxyalkanoates rich in specific monomers.
2002 Sep 10
Computer-aided real-time estimation of reaction conversion for lipase-catalyzed esterification in solvent-free systems.
2002 Sep 30
Gastric emptying in rats following administration of a range of different fats measured as acetaminophen concentration in plasma.
2003
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
Alpha 2u-globulin nephropathy and carcinogenicity following exposure to decalin (decahydronaphthalene) in F344/N rats.
2003 Apr
Single administration toxicokinetic studies of decalin (decahydronaphthalene) in rats and mice.
2003 Apr
Research on psychological testing supervision using the Holloway (1995) method: a critique of DeCato (2002).
2003 Feb
A new Escherichia coli metabolic competency: growth on fatty acids by a novel anaerobic beta-oxidation pathway.
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
Plasma fatty acids and [13C]linoleic acid metabolism in preterm infants fed a formula with medium-chain triglycerides.
2003 Jan
The relationship between dopamine D2 receptor occupancy and the vacuous chewing movement syndrome in rats.
2003 Jan
First-order kinetics analysis of monomer composition dependent polyhydroxyalkanoic acid degradation in Pseudomonas spp.
2003 Mar-Apr
The effect of conjugated linoleic acid and medium-chain fatty acids on transepithelial calcium transport in human intestinal-like Caco-2 cells.
2003 May
Accumulation of 3-hydroxy-fatty acids in the culture medium of long-chain L-3-hydroxyacyl CoA dehydrogenase (LCHAD) and mitochondrial trifunctional protein-deficient skin fibroblasts: implications for medium chain triglyceride dietary treatment of LCHAD deficiency.
2003 May
Acute mechanism of medium chain fatty acid-induced enhancement of airway epithelial permeability.
2003 May
Fatty acids as an energy source for the operation of axoplasmic transport.
2003 May 16
Triacylglycerols determine the unusual storage physiology of Cuphea seed.
2003 Sep
Synthesis of monocaprin catalyzed by lipase.
2003 Spring
Patents

Sample Use Guides

The oral minimal dose is 1723 mg/kg (animal model).
Route of Administration: Oral
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 Sat Jun 26 12:46:31 UTC 2021
Edited
by admin
on Sat Jun 26 12:46:31 UTC 2021
Record UNII
4G9EDB6V73
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CAPRIC ACID
INCI  
INCI  
Official Name English
N-CAPRIC ACID [MI]
Common Name English
PRIFAC-2906
Code English
DECANOIC ACID [FCC]
Common Name English
CAPRIC ACID [INCI]
Common Name English
DECANOIC ACID
FCC   FHFI   HSDB  
Systematic Name English
DECANOIC ACID [FHFI]
Common Name English
N-DECANOIC ACID
Common Name English
1-NONANECARBOXYLIC ACID
Systematic Name English
N-CAPRIC ACID
MI   WHO-DD  
Common Name English
PALMAC-99-10
Code English
N-CAPRIC ACID [WHO-DD]
Common Name English
NSC-5025
Code English
CAPRIC ACID (CONSTITUENT OF SAW PALMETTO) [DSC]
Common Name English
DECANOIC ACID [HSDB]
Common Name English
FEMA NO. 2364
Code English
Classification Tree Code System Code
CFR 21 CFR 172.860
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
DSLD 2486 (Number of products:70)
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
NCI_THESAURUS C68421
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
JECFA EVALUATION DECANOIC ACID
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
EPA PESTICIDE CODE 128955
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
NCI_THESAURUS C68391
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
Code System Code Type Description
MERCK INDEX
M3030
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY Merck Index
CAS
334-48-5
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
MESH
C031071
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
FDA UNII
4G9EDB6V73
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
WIKIPEDIA
DECANOIC ACID
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
ECHA (EC/EINECS)
206-376-4
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
RXCUI
22380
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB03600
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
PUBCHEM
2969
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
EVMPD
SUB70871
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
EPA CompTox
334-48-5
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
HSDB
2751
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
NCI_THESAURUS
C68329
Created by admin on Sat Jun 26 12:46:31 UTC 2021 , Edited by admin on Sat Jun 26 12:46:31 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY