CAPRIC ACID

Possibly Marketed Outside US

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

Structure Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23177536 | https://www.ncbi.nlm.nih.gov/pubmed/26912516 | https://www.ncbi.nlm.nih.gov/pubmed/27080638

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
Glutamate receptor ionotropic AMPA 41 Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26608744	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) Sources: https://www.ncbi.nlm.nih.gov/pubmed/27080638	Modulator 828		41.7 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inherited metabolic diseases 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27080638	Primary		Basic research	Unknown Approved Use Unknown
Seizure 4 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26608744	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)].	2001 Aug	11862667
Antipsychotic prescribing practices in Connecticut's public mental health system: rates of changing medications and prescribing styles.	2002	12047017
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	12033371
The influence of caprate on rectal absorption of phenoxymethylpenicillin: experience from an in-vivo perfusion in humans.	2002 Apr	11999127
A multidose study of haloperidol decanoate in the maintenance treatment of schizophrenia.	2002 Apr	11925292
PCR cloning of polyhydroxyalkanoate biosynthesis genes from Burkholderia caryophylli and their functional expression in recombinant Escherichia coli.	2002 Apr 23	12023076
Detection of fast light-activated H+ release and M intermediate formation from proteorhodopsin.	2002 Apr 9	11943070
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	12214995
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	12115060
Identification of bacteria in drinking and purified water during the monitoring of a typical water purification system.	2002 Aug 15	12182763
Trail pheromone of ponerine ant Gnamptogenys striatula: 4-methylgeranyl esters from Dufour's gland.	2002 Dec	12564800
19F-magnetic resonance spectroscopy and chemical shift imaging for schizophrenic patients using haloperidol decanoate.	2002 Dec	12485307
Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis.	2002 Dec	12423658
Enhancement of paracellular transport of heparin disaccharide across Caco-2 cell monolayers.	2002 Feb	11885699
Self-assembled vesicles of monocarboxylic acids and alcohols: conditions for stability and for the encapsulation of biopolymers.	2002 Feb 10	11825583
The enhancing effect of nasal absorption of FITC-dextran 4,400 by beta-sitosterol beta-D-glucoside in rabbits.	2002 Feb 19	11853926
Nasal glucagon delivery using microcrystalline cellulose in healthy volunteers.	2002 Feb 21	11897411
Preparation and catalytic performance of lipases encapsulated in sol-gel materials.	2002 Jan	11866115
Flavor production from edible oils and their constituents by Penicillium corylophilum.	2002 Jun	12238154
Comparison of effects of khat extract and amphetamine on motor behaviors in mice.	2002 Jun	12020929
Simultaneous production of polyhydroxyalkanoates and rhamnolipids by Pseudomonas aeruginosa.	2002 Jun 20	11992535
Evidence in favor of a facilitated transport system for FA uptake in cultured L6 cells.	2002 Mar	11942478
Tardive dyskinesia model in the common marmoset.	2002 Mar	11921124
Purification and characterization of a novel cholesterol esterase from Pseudomonas aeruginosa, with its application to cleaning lipid-stained contact lenses.	2002 Nov	12506971
Haloperidol decanoate doses of 200, 100, or 50 mg/month reduced symptomatic exacerbations more than a 25 mg/month dose in schizophrenia.	2002 Nov	12440454
Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid.	2002 Nov	12423358
The effect of age on the pharmacological management of ambulatory patients treated with depot neuroleptic medications for schizophrenia and related psychotic disorders.	2002 Nov	12404650
Effect of sodium caprate on the intestinal absorption of two modified antisense oligonucleotides in pigs.	2002 Nov	12393140
[Deterioration of schizoaffective disorder due to an interaction between haloperidol and carbamazepine].	2002 Oct 12	12404911
Solid-phase microextraction in combination with GC/MS for quantification of the major volatile free fatty acids in ewe cheese.	2002 Oct 15	12403571
Beta-ketoacyl-acyl carrier protein synthase IV: a key enzyme for regulation of medium-chain fatty acid synthesis in Cuphea lanceolata seeds.	2002 Sep	12244451
Chicken ghrelin: purification, cDNA cloning, and biological activity.	2002 Sep	12193558
Metabolic engineering of Escherichia coli for the production of medium-chain-length polyhydroxyalkanoates rich in specific monomers.	2002 Sep 10	12351234
Computer-aided real-time estimation of reaction conversion for lipase-catalyzed esterification in solvent-free systems.	2002 Sep 30	12209802
Gastric emptying in rats following administration of a range of different fats measured as acetaminophen concentration in plasma.	2003	12743464
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	12661076
Alpha 2u-globulin nephropathy and carcinogenicity following exposure to decalin (decahydronaphthalene) in F344/N rats.	2003 Apr	12660359
Single administration toxicokinetic studies of decalin (decahydronaphthalene) in rats and mice.	2003 Apr	12660358
Research on psychological testing supervision using the Holloway (1995) method: a critique of DeCato (2002).	2003 Feb	12674272
A new Escherichia coli metabolic competency: growth on fatty acids by a novel anaerobic beta-oxidation pathway.	2003 Feb	12535077
Enhancement of adenovirus-mediated gene transfer to the airways by DEAE dextran and sodium caprate in vivo.	2003 Jan	12573614
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	12532160
Plasma fatty acids and [13C]linoleic acid metabolism in preterm infants fed a formula with medium-chain triglycerides.	2003 Jan	12518021
The relationship between dopamine D2 receptor occupancy and the vacuous chewing movement syndrome in rats.	2003 Jan	12417967
First-order kinetics analysis of monomer composition dependent polyhydroxyalkanoic acid degradation in Pseudomonas spp.	2003 Mar-Apr	12625741
The effect of conjugated linoleic acid and medium-chain fatty acids on transepithelial calcium transport in human intestinal-like Caco-2 cells.	2003 May	12720584
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	12621125
Fatty acids as an energy source for the operation of axoplasmic transport.	2003 May 16	12711076
Triacylglycerols determine the unusual storage physiology of Cuphea seed.	2003 Sep	12743824
Synthesis of monocaprin catalyzed by lipase.	2003 Spring	12721413

Patents

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.

Name

Type

Language

CAPRIC ACID

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

Systematic Name

English

DECANOIC ACID [FHFI]

Common Name

English

N-DECANOIC ACID

Common Name

English

1-NONANECARBOXYLIC ACID

Systematic Name

English

N-CAPRIC ACID

Common Name

English

PALMAC-99-10

Code

English

NSC-5025

Code

English

N-Capric acid [WHO-DD]

Common Name

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