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Details

Stereochemistry ACHIRAL
Molecular Formula C27H50O6
Molecular Weight 470.6823
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRICAPRILIN

SMILES

CCCCCCCC(=O)OCC(COC(=O)CCCCCCC)OC(=O)CCCCCCC

InChI

InChIKey=VLPFTAMPNXLGLX-UHFFFAOYSA-N
InChI=1S/C27H50O6/c1-4-7-10-13-16-19-25(28)31-22-24(33-27(30)21-18-15-12-9-6-3)23-32-26(29)20-17-14-11-8-5-2/h24H,4-23H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C27H50O6
Molecular Weight 470.6823
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.drugs.com/cdi/axona.html and https://www.ncbi.nlm.nih.gov/pubmed/19664276

Tricaprylin is a triester of glycerin and caprylic acid. It is used as a fragrance ingredient, solvent, and primarily as an emollient in a variety of personal care products, including makeup, creams and lotions, deodorants, sunscreens, hair conditioners, and skin cleansers. Tricaprylin is an ingredient of Axona, a prescription medical food intended for the clinical dietary management of the metabolic processes associated with mild to moderate Alzheimer’s disease. Axona provides a simple and safe method to induce hyperketonemia, thus providing an alternative energy substrate to glucose in the brain of patients with AD. After oral administration of Axona, Tricaprylin in Axona is processed by enzymes in the gut, and the resulting medium-chain fatty acids (MCFAs) are absorbed into the blood supply leading to the liver. The MCFAs rapidly pass directly to the liver, where they undergo oxidation to form ketones. Since the liver does not use ketones, they are released into the circulation to be used by nonliver tissues. Some ketones can cross the blood-brain barrier and are then taken up by brain cells. While glucose is the brain’s chief energy source, ketones normally serve as the "backup" energy source. Ketones the body produces after Axona is consumed, act as an alternative energy source for brain cells that have lost their ability to use glucose (sugar) as a result of Alzheimer’s disease.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Axona

Approved Use

For the clinical dietary management of the metabolic processes associated with mild to moderate Alzheimer’s disease (AD)

Launch Date

2009
PubMed

PubMed

TitleDatePubMed
Blood D-(-)-3-hydroxybutyrate concentrations after oral administration of trioctanoin, trinonanoin, or tridecanoin to newborn rhesus monkeys (Macaca mulatta).
2010-12
Influence of cyclosporine A on molecular interactions in lyotropic reverse hexagonal liquid crystals.
2010-10-14
Biochemical characterization and mutational improvement of a thermophilic esterase from Sulfolobus solfataricus P2.
2010-08
Pulmonary modulation of benzo[a]pyrene-induced hemato- and hepatotoxicity in broilers.
2010-07
Should the ApoE genotype be a covariate for clinical trials in Alzheimer disease?
2010-06-08
Lysozyme entrapped within reverse hexagonal mesophases: physical properties and structural behavior.
2010-01-01
Structural rearrangements and interaction within H(II) mesophase induced by cosolubilization of vitamin E and ascorbic acid.
2009-11-17
Fatty acid selectivity of lipases during acidolysis reaction between oleic acid and monoacid triacylglycerols.
2009-11-11
Achievements and new knowledge unraveled by metagenomic approaches.
2009-11
Thermostable lipases from the extreme thermophilic anaerobic bacteria Thermoanaerobacter thermohydrosulfuricus SOL1 and Caldanaerobacter subterraneus subsp. tengcongensis.
2009-09
Lipase-catalyzed reactions at interfaces of two-phase systems and microemulsions.
2009-09
Study of the ketogenic agent AC-1202 in mild to moderate Alzheimer's disease: a randomized, double-blind, placebo-controlled, multicenter trial.
2009-08-10
Effect of octanoic acid-rich formula on plasma ghrelin levels in cachectic patients with chronic respiratory disease.
2009-06-16
Molecular dynamics simulations of functional group effects on solvation thermodynamics of model solutes in decane and tricaprylin.
2009-05-13
Modeling kinetics of subcellular disposition of chemicals.
2009-05
Molecular interactions in reverse hexagonal mesophase in the presence of Cyclosporin A.
2009-02-09
Identifying efficacious approaches to chemoprevention with chlorophyllin, purified chlorophylls and freeze-dried spinach in a mouse model of transplacental carcinogenesis.
2009-02
Cloning and characterization of a new cold-active lipase from a deep-sea sediment metagenome.
2009-01
Effects of cytochrome p450 inhibitors on itraconazole and fluconazole induced cytotoxicity in hepatocytes.
2009
Distinction between esterases and lipases: comparative biochemical properties of sequence-related carboxylesterases.
2009
Esterification and hydrolytic activities of Candida rugosa lipase isoform 1 (LIP1) immobilized on celite 545, duolite A7, and sephadex G-25.
2008-11-12
Solubilization of nutraceuticals into reverse hexagonal mesophases.
2008-08-21
Competition between lipases and monoglycerides at interfaces.
2008-07-15
Action of Humicola lanuginosa lipase on mixed monomolecular films of tricaprylin and polyethylene glycol stearate.
2008-05-01
Quantitative solubility relationships and the effect of water uptake in triglyceride/monoglyceride microemulsions.
2008-05
Low viscosity reversed hexagonal mesophases induced by hydrophilic additives.
2008-04-03
Vehicle-dependent disposition kinetics of fluoranthene in Fisher-344 rats.
2008-03
A comparative study on two fungal lipases from Thermomyces lanuginosus and Yarrowia lipolytica shows the combined effects of detergents and pH on lipase adsorption and activity.
2007-12
Isolation of lipase producing Bacillus sp. from olive mill wastewater and improving its enzyme activity.
2007-11-19
An HII liquid crystal-based delivery system for cyclosporin A: physical characterization.
2007-04-15
[Microstructure of novel solid lipid nanoparticle loaded triptolide].
2007-04
Kinetic model of 1,3-specific triacylglycerols alcoholysis catalyzed by lipases.
2007-01-20
Effects of protein composition and enzymatic activity on formation and properties of potato protein stabilized emulsions.
2006-08-23
Stability of triglyceride liquid films on hydrophilic and hydrophobic glasses.
2006-07-01
Val-407 and Ile-408 in the beta5'-loop of pancreatic lipase mediate lipase-colipase interactions in the presence of bile salt micelles.
2006-03-24
Technological properties of Enterococcus faecium isolated from ewe's milk and cheese with importance for flavour development.
2006-03
Lymphatic transport of a physical mixture of medium- and long-chain TAG in rats.
2006-01
Secretion of pro- and mature Rhizopus arrhizus lipases by Pichia pastoris and properties of the proteins.
2006-01
Substrate specificity and kinetic properties of enzymes belonging to the hormone-sensitive lipase family: comparison with non-lipolytic and lipolytic carboxylesterases.
2005-12-30
Topical absorption of piroxicam from organogels--in vitro and in vivo correlations.
2005-07-14
Transitions induced by solubilized fat into reverse hexagonal mesophases.
2005-06-25
Tricaprylin microemulsion for oral delivery of low molecular weight heparin conjugates.
2005-06-20
Mutations in the "lid" region affect chain length specificity and thermostability of a Pseudomonas fragi lipase.
2005-04-25
Dialkylphosphatidylcholine and egg yolk lecithin for emulsification of various triglycerides.
2005-04-10
Might the kinetic behavior of hormone-sensitive lipase reflect the absence of the lid domain?
2004-07-27
Structural characterisation of water-Tween 40/Imwitor 308-isopropyl myristate microemulsions using different experimental methods.
2004-05-19
On the calculation of disjoining pressure isotherms for nonaqueous films.
2004-02-15
[Effect of triester glycerol type of plasticizers on release of albumin from biodegradable polymer matrices].
2004-01
Quantitative evaluation of reconstruction methods after gastrectomy using a new type of examination: digestion and absorption test with stable isotope 13C-labeled lipid compound.
2003
Interstrain differences in susceptibility to liver carcinogenesis initiated by N-nitrosodiethylamine and its promotion by phenobarbital in C57BL/6NCr, C3H/HeNCrMTV- and DBA/2NCr mice.
1986-02
Patents

Patents

Sample Use Guides

Axona is taken orally once a day shortly after a full meal. Patients should start with a graduated dosing regimen for 7 days, or as directed by the supervising healthcare provider, before taking one full packet (40 grams) per day. Axona should be added to 4 to 8 ounces (118 to 236 milliliters) of water or other liquids, and shaken or blended until fully mixed. Axona consists primarily of a proprietary formulation of >95% pure semisynthetic caprylic triglyceride (Tricaprylin). Each 40g packet contains 20 g of Tricaprylin
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:09:20 GMT 2025
Edited
by admin
on Mon Mar 31 18:09:20 GMT 2025
Record UNII
6P92858988
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TRICAPRYLIN
II   INCI   MART.  
INCI  
Preferred Name English
TRICAPRILIN
HSDB   JAN  
INN   USAN  
Official Name English
AXONA
VANDF  
Brand Name English
CER-0001
Code English
CAPRYLIC TRIGLYCERIDE [VANDF]
Common Name English
TRICAPRYLIC GLYCERIDE
Common Name English
tricaprilin [INN]
Common Name English
AXONA [VANDF]
Common Name English
CAPRYLIC ACID TRIGLYCERIDE
Common Name English
TRICAPRILIN [JAN]
Common Name English
TRICAPRILIN [HSDB]
Common Name English
Octanoic acid, 1,2,3-propanetriyl ester
Common Name English
NSC-4059
Code English
CAPRYLIC TRIGLYCERIDE
VANDF  
Common Name English
TRICAPRYLYL GLYCEROL
Systematic Name English
GLYCERYL TRICAPRYLATE [NF]
Common Name English
TRICAPRYLIN [MART.]
Common Name English
MIGLYOL 808
Brand Name English
AC-1204
Code English
Tricaprilin [WHO-DD]
Common Name English
GLYCEROL TRIOCTANOATE
Systematic Name English
TRICAPRYLYL GLYCERIN
Systematic Name English
AC-1202
Code English
GLYCERYL TRICAPRYLATE [USP-RS]
Common Name English
TRICAPRILIN [USAN]
Common Name English
TRICAPRYLIN [II]
Common Name English
GLYCEROL TRICAPRYLATE
Systematic Name English
GLYCERYL TRICAPRYLATE
Common Name English
OCTANOIC ACID, 1,1',1''-(1,2,3-PROPANETRIYL) ESTER
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 777020
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
Code System Code Type Description
WIKIPEDIA
AXONA
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
HSDB
7829
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
ECHA (EC/EINECS)
208-686-5
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
NSC
4059
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
EPA CompTox
DTXSID6021375
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
INN
10584
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
EVMPD
SUB126762
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
RXCUI
1314420
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY RxNorm
FDA UNII
6P92858988
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
PUBCHEM
10850
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
DRUG BANK
DB12176
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
DAILYMED
6P92858988
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
CAS
538-23-8
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
ChEMBL
CHEMBL1406148
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
USAN
FG-180
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
RS_ITEM_NUM
1295797
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
CHEBI
76978
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
CONCEPT Industrial Aid
NCI_THESAURUS
C29861
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
SMS_ID
100000152983
Created by admin on Mon Mar 31 18:09:20 GMT 2025 , Edited by admin on Mon Mar 31 18:09:20 GMT 2025
PRIMARY
Related Record Type Details
LABELED -> NON-LABELED
Related Record Type Details
ACTIVE MOIETY