Compound: Tricaprylin
SMILES: O=C(OC(COC(=O)CCCCCCC)COC(=O)CCCCCCC)CCCCCCC
InChIKey: VLPFTAMPNXLGLX-UHFFFAOYSA-N
Synonyms: Tricaprylin, Trioctanoin, 538-23-8, Tricaprilin, Glycerol trioctanoate, Rato, Glycerol tricaprylate, Caprylin, Trioctanoylglycerol, Glyceryl trioctanoate, Maceight, Caprylic acid triglyceride, Glyceryl tricaprylate, Tricaprylic glyceride, Caprylic triglyceride, Octanoin, tri-, Octanoic acid triglyceride, Tricaprylyl glycerin, Panacete 800, Octanoic acid, 1,2,3-propanetriyl ester, Glycerin tricaprylate, Miglyol 808, Sefsol 800, Tricapryloylglycerol, Tricaprylyl glycerol, Tricaprilina, Tricapriline, 1,2,3-Propanetriol trioctanoate, CER-0001, NSC-4059, trioctanoylglyceride, Caprylic acid, 1,2,3-propanetriyl ester, DTXSID6021375, DTXCID801375, CHEBI:76978, NSC4059, 6P92858988, tricaprilinum, 1,3-bis(octanoyloxy)propan-2-yl octanoate, RefChem:899159, 208-686-5, Propane-1,2,3-triyl trioctanoate, 1,2,3-Tri-n-octanoylglycerol, Axona, 2,3-di(octanoyloxy)propyl octanoate, MFCD00036236, Glycerol Tri-n-octanoate, NSC 4059, AC-1202, Octanoic acid, 1,1',1''-(1,2,3-propanetriyl) ester, Trioctanoin;Glyceryl trioctanoate, AC-1204, NCGC00091285-01, TG(8:0/8:0/8:0), Tricaprilin [JAN], caprylidene, Tri-n-octanoin, CAS-538-23-8, GLYCERYL TRI(OCTANOATE-2,2-D2), GLYCERYL TRI(OCTANOATE-8,8,8-D3), EINECS 208-686-5, 1,2,3-Tricapryloylglycerol, BRN 1717202, tricaprylm, Tri-octanoin, Tri-n-caprylin, Tricaprylin CRS, HSDB 7829, Emalex KTG, Glycerol trioctanoin, UNII-6P92858988, Sefsol 810, Tricaprylin(>90%), Captex 8000, Tricaprilin (Standard), AXONA [VANDF], Glycerol trioctanoic acid, TRICAPRYLIN [II], TRICAPRILIN [INN], Tricaprilin (JAN/USAN), Tricaprilin [USAN:JAN], TRICAPRILIN [HSDB], TRICAPRILIN [USAN], 1,2,3-Trioctanoylglycerol, TRICAPRYLIN [MART.], 1,2,3-trioctanoyl glycerol, SCHEMBL61958, TRICAPRILIN [WHO-DD], 4-02-00-00991 (Beilstein Handbook Reference), MLS002454452, Trioctanoin-1,1,1-13C3, Glyceryl trioctanoate, >=99%, orb1301941, CHEMBL1406148, HY-B1804R, MSK2023, Propane-1,2,3-triyltrioctanoate, Trioctanoin; Glyceryl trioctanoate, GLYCERYL TRICAPRYLATE [NF], HMS3039H17, HMS5085K16, 1,2,3-tris-(octanoyloxy)-propane, HY-B1804, Tox21_111110, Tox21_201480, Tox21_302762, CAPRYLIC TRIGLYCERIDE [VANDF], s6342, WHO 10584, Octanoic acid,2,3-propanetriyl ester, AKOS015899778, GLYCERYL TRICAPRYLATE [USP-RS], Tox21_111110_1, CCG-214786, DB12176, 2,3-Bis(octanoyloxy)propyl octanoate #, NCGC00091285-02, NCGC00091285-03, NCGC00256431-01, NCGC00259031-01, AS-75522, BP-29597, FT166788, SMR001372028, SY052070, DB-071745, CS-0013846, NS00013245, ST51037450, A11562, D01587, Glyceryl trioctanoate, technical, >=90% (GC), 2-octanoyloxy-1-(octanoyloxymethyl)ethyl octanoate, F813335, SR-01000854712, TG 8:0_8:0_8:0, Q2747851, SR-01000854712-2, BRD-K24790130-001-07-1, Tricaprylin, European Pharmacopoeia (EP) Reference Standard, 352431-34-6, 352431-35-7
Theoretical properties:
molecular_formula: C27H50O6
molecular_weight: 470.7 g/mol
exact_mass: 470.36073931 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 26
heavy_atom_count: 33
topological_polar_surface_area: 78.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Clear, colorless to amber liquid
color: Clear, colorless to amber liquid
boiling_point: 451.6 °F at 760 mmHg (NTP, 1992)
melting_point: 50 °F (NTP, 1992)
density: 0.954 at 68 °F (NTP, 1992) - Less dense than water; will float
solubility: less than 1 mg/mL at 72 °F (NTP, 1992)
flash_point: 351 °F (NTP, 1992)
vapor_pressure: 3 mmHg at 77 °F ; 13 mmHg at 122 °F (NTP, 1992)
Descriptions:
pubchem: Trioctanoin is a triglyceride obtained by acylation of the three hydroxy groups of glycerol by octanoic acid. Used as an alternative energy source to glucose for patients with mild to moderate Alzheimer's disease. It has a role as an anticonvulsant and a plant metabolite. It is a triglyceride and an octanoate ester.
chebi: A triglyceride obtained by acylation of the three hydroxy groups of glycerol by octanoic acid. Used as an alternative energy source to glucose for patients with mild to moderate Alzheimer's disease.
chembl: TRICAPRILIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Axona was previously marketed as a medical food for the clinical dietary management of the impairment of metabolic processes associated with mild to moderate Alzheimer's disease.  It is a proprietary formulation of fractionated palm kernel oil (caprylic triglyceride), a medium-chain triglyceride.  Cericin, the company that makes Axona, states that during digestion, caprylic triglyceride is broken down into ketones, which provide an alternative energy source for the brain.  Its use is based on the idea that the brain's ability to use its normal energy source, glucose, is impaired in Alzheimer's disease.  Axona was first sold in March 2009.
In 2013, US Food and Drug Administration (FDA) determined Axona was misbranded because the product was labeled and marketed as a medical food but does not meet the statutory definition of a medical food.  Axona has not been approved by the FDA as a drug to treat Alzheimer's and the efficacy of managing the health of Alzheimer's patients by use of this medical food has been questioned by experts in the field, including the Alzheimer's Association.