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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 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 172.2646
Charge 0
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
60
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 0.43 mM [IC50]
Peroxisome proliferator-activated receptor gamma
118
Target ID: P37231|||Q15179
Gene ID: 5468.0
Gene Symbol: PPARG
Target Organism: Homo sapiens (Human)
Modulator
846
 41.7 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Triacylglycerols determine the unusual storage physiology of Cuphea seed.
2003-09
Fatty acids as an energy source for the operation of axoplasmic transport.
2003-05-16
The effect of conjugated linoleic acid and medium-chain fatty acids on transepithelial calcium transport in human intestinal-like Caco-2 cells.
2003-05
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.
2003-05
Acute mechanism of medium chain fatty acid-induced enhancement of airway epithelial permeability.
2003-05
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.
2003-04
Alpha 2u-globulin nephropathy and carcinogenicity following exposure to decalin (decahydronaphthalene) in F344/N rats.
2003-04
Single administration toxicokinetic studies of decalin (decahydronaphthalene) in rats and mice.
2003-04
First-order kinetics analysis of monomer composition dependent polyhydroxyalkanoic acid degradation in Pseudomonas spp.
2003-03-11
Research on psychological testing supervision using the Holloway (1995) method: a critique of DeCato (2002).
2003-02
A new Escherichia coli metabolic competency: growth on fatty acids by a novel anaerobic beta-oxidation pathway.
2003-02
Enhancement of adenovirus-mediated gene transfer to the airways by DEAE dextran and sodium caprate in vivo.
2003-01
Medium- versus long-chain triglycerides for 27 days increases fat oxidation and energy expenditure without resulting in changes in body composition in overweight women.
2003-01
Plasma fatty acids and [13C]linoleic acid metabolism in preterm infants fed a formula with medium-chain triglycerides.
2003-01
The relationship between dopamine D2 receptor occupancy and the vacuous chewing movement syndrome in rats.
2003-01
Gastric emptying in rats following administration of a range of different fats measured as acetaminophen concentration in plasma.
2003
Synthesis of monocaprin catalyzed by lipase.
2003
Intramuscular preparations of antipsychotics: uses and relevance in clinical practice.
2003
Trail pheromone of ponerine ant Gnamptogenys striatula: 4-methylgeranyl esters from Dufour's gland.
2002-12
19F-magnetic resonance spectroscopy and chemical shift imaging for schizophrenic patients using haloperidol decanoate.
2002-12
Ranking the toxicity of fatty acids on Jurkat and Raji cells by flow cytometric analysis.
2002-12
Purification and characterization of a novel cholesterol esterase from Pseudomonas aeruginosa, with its application to cleaning lipid-stained contact lenses.
2002-11
In vitro evaluation of the release of albuterol sulfate from polymer gels: effect of fatty acids on drug transport across biological membranes.
2002-11
Acyl CoA profiles of transgenic plants that accumulate medium-chain fatty acids indicate inefficient storage lipid synthesis in developing oilseeds.
2002-11
Haloperidol decanoate doses of 200, 100, or 50 mg/month reduced symptomatic exacerbations more than a 25 mg/month dose in schizophrenia.
2002-11
Characterization of the exopolysaccharide produced by Streptococcus thermophilus 8S containing an open chain nononic acid.
2002-11
The effect of age on the pharmacological management of ambulatory patients treated with depot neuroleptic medications for schizophrenia and related psychotic disorders.
2002-11
Effect of sodium caprate on the intestinal absorption of two modified antisense oligonucleotides in pigs.
2002-11
Solid-phase microextraction in combination with GC/MS for quantification of the major volatile free fatty acids in ewe cheese.
2002-10-15
[Deterioration of schizoaffective disorder due to an interaction between haloperidol and carbamazepine].
2002-10-12
Biochemical evidence against protein-mediated uptake of myristic acid in the bioluminescent marine bacterium Vibrio harveyi.
2002-10
Computer-aided real-time estimation of reaction conversion for lipase-catalyzed esterification in solvent-free systems.
2002-09-30
Metabolic engineering of Escherichia coli for the production of medium-chain-length polyhydroxyalkanoates rich in specific monomers.
2002-09-10
Beta-ketoacyl-acyl carrier protein synthase IV: a key enzyme for regulation of medium-chain fatty acid synthesis in Cuphea lanceolata seeds.
2002-09
Chicken ghrelin: purification, cDNA cloning, and biological activity.
2002-09
Identification of bacteria in drinking and purified water during the monitoring of a typical water purification system.
2002-08-15
Effect of dose of calcium salts of conjugated linoleic acid (CLA) on percentage and fatty acid content of milk fat in midlactation holstein cows.
2002-08
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.
2002-08
Effect of fatty acid chain length on initial reaction rates and regioselectivity of lipase-catalysed esterification of disaccharides.
2002-07-16
Suppressive effect of saturated acyl L-ascorbate on the oxidation of linoleic acid encapsulated with maltodextrin or gum arabic by spray-drying.
2002-07-03
Simultaneous production of polyhydroxyalkanoates and rhamnolipids by Pseudomonas aeruginosa.
2002-06-20
Flavor production from edible oils and their constituents by Penicillium corylophilum.
2002-06
Comparison of effects of khat extract and amphetamine on motor behaviors in mice.
2002-06
PCR cloning of polyhydroxyalkanoate biosynthesis genes from Burkholderia caryophylli and their functional expression in recombinant Escherichia coli.
2002-04-23
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.
2002-04
The influence of caprate on rectal absorption of phenoxymethylpenicillin: experience from an in-vivo perfusion in humans.
2002-04
Kinetic analysis of hydroxylation of saturated fatty acids by recombinant P450foxy produced by an Escherichia coli expression system.
2002-04
Penetration of engineered antibody fragments into the eye.
2002-04
Saturated triglycerides and fatty acids activate neutrophils depending on carbon chain-length.
2002-04
Antipsychotic prescribing practices in Connecticut's public mental health system: rates of changing medications and prescribing styles.
2002
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 Mon Mar 31 17:48:12 GMT 2025
Edited
by admin
on Mon Mar 31 17:48:12 GMT 2025
Record UNII
4G9EDB6V73
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DECANOIC ACID
FCC   FHFI   HSDB  
Preferred Name English
CAPRIC ACID
INCI  
INCI  
Official Name English
N-CAPRIC ACID [MI]
Common Name English
PRIFAC-2906
Code English
DECANOIC ACID [FCC]
Common 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
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
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
DSLD 2486 (Number of products:70)
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
NCI_THESAURUS C68421
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
JECFA EVALUATION DECANOIC ACID
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
EPA PESTICIDE CODE 128955
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
NCI_THESAURUS C68391
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
Code System Code Type Description
MERCK INDEX
m3030
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY Merck Index
CAS
334-48-5
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
NSC
5025
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
MESH
C031071
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
FDA UNII
4G9EDB6V73
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
WIKIPEDIA
DECANOIC ACID
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
SMS_ID
100000135492
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
DAILYMED
4G9EDB6V73
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
CHEBI
44499
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-376-4
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
RXCUI
22380
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY RxNorm
DRUG BANK
DB03600
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
PUBCHEM
2969
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
EVMPD
SUB70871
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
EPA CompTox
DTXSID9021554
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
JECFA MONOGRAPH
10
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
HSDB
2751
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
CHEBI
30813
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
NCI_THESAURUS
C68329
Created by admin on Mon Mar 31 17:48:13 GMT 2025 , Edited by admin on Mon Mar 31 17:48:13 GMT 2025
PRIMARY
Related Record Type Details
Structure of Lead(2+) decanoate
SALT/SOLVATE -> PARENT
Structure of POTASSIUM CAPRATE
SALT/SOLVATE -> PARENT
Structure of LITHIUM CAPRATE
SALT/SOLVATE -> PARENT
Structure of CALCIUM DECANOATE
SALT/SOLVATE -> PARENT
Structure of ZINC DECANOATE
SALT/SOLVATE -> PARENT
Structure of MORPHOLINE DECANOATE
SALT/SOLVATE -> PARENT
Structure of MAGNESIUM DECANOATE
SALT/SOLVATE -> PARENT
Coconut oil
LIPID -> FATTY ACID
JB Rossell and co-workers; JAOCS62(2), 221-230(1985). Range weight is a mean.
Structure of SODIUM CAPRATE
SALT/SOLVATE -> PARENT
Structure of Lanthanum(3+) decanoate
SALT/SOLVATE -> PARENT
SAW PALMETTO
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of CAPRIC ACID
ACTIVE MOIETY
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
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