CAPRIC ACID

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

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

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 42 Target ID: CHEMBL2096670 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26608744	Antagonist 2760		0.43 mM [IC50]
Peroxisome proliferator-activated receptor gamma 109 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 822		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
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	11305600
[New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium(L.) Moench.)].	2001 Aug	11862667
Increased vigabatrin entry into the brain by polysorbate 80 and sodium caprate.	2001 Feb	11273010
Increased incidence of dyskinesias and other behavioral effects of re-exposure to neuroleptic treatment in social colonies of Cebus apella monkeys.	2001 Jan	11271400
Medium-chain fatty acids stimulate interleukin-8 production in Caco-2 cells with different mechanisms from long-chain fatty acids.	2001 Jul	11446882
Significance of substrate hydrophobicity for recognition by an oligopeptide transporter (PEPT1).	2001 Jul-Aug	11459451
Coupling of fermentation and esterification: microbial esterification of decanoic acid with ethanol produced via fermentation.	2001 Jun	11471739
Acute and chronic haloperidol treatments increase parkin mRNA levels in the rat brain.	2001 Jun 22	11403966
Estimation of absorption enhancement by medium-chain fatty acids in rat large intestine.	2001 Mar-Apr	11758652
Antifungal activities of pelargonic and capric acid on Microsporum gypseum.	2001 May	11413921
A fluorogenic reagent, 4-mercapto-7-methylthio-2,1,3-benzoxadiazole for carboxylic acids, designed by prediction of the fluorescence intensity.	2001 May 15	11393836
Mechanistic study into the enhanced transdermal permeation of a model beta-blocker, propranolol, by fatty acids: a melting point depression effect.	2001 May 21	11337176
Lipolytic activity of ricin from Ricinus sanguineus and Ricinus communis on neutral lipids.	2001 Sep 15	11535138
Penetration of engineered antibody fragments into the eye.	2002 Apr	11982592
Antioxidant and cyclooxygenase activities of fatty acids found in food.	2002 Apr 10	11929276
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
Hydroxylation of fatty acids by microsomal and reconstituted cytochrome P450 2B1.	2002 Feb 13	11852103
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
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
In vitro evaluation of the release of albuterol sulfate from polymer gels: effect of fatty acids on drug transport across biological membranes.	2002 Nov	12476868
Acyl CoA profiles of transgenic plants that accumulate medium-chain fatty acids indicate inefficient storage lipid synthesis in developing oilseeds.	2002 Nov	12445123
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
Biochemical evidence against protein-mediated uptake of myristic acid in the bioluminescent marine bacterium Vibrio harveyi.	2002 Oct	12489783
[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
A new Escherichia coli metabolic competency: growth on fatty acids by a novel anaerobic beta-oxidation pathway.	2003 Feb	12535077
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
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.

Substance Class	Chemical Created by `admin` on `Wed Jul 05 22:40:56 UTC 2023` Edited by `admin` on `Wed Jul 05 22:40:56 UTC 2023`
Record UNII	4G9EDB6V73
Record Status	`Validated (UNII)`
Record Version

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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