Octanoin, tri- (Octanoic acid, 1,2,3-propanetriyl ester; Tricaprylin) (CHEM015742)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 05:01:28 UTC
Update Date2016-10-28 10:03:29 UTC
Accession NumberCHEM015742
Identification
Common NameOctanoin, tri- (Octanoic acid, 1,2,3-propanetriyl ester; Tricaprylin)
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • Cosmetic Chemicals
  • FooDB Chemicals
  • OECD HPV Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3-Propanetriol trioctanoateChEBI
1,2,3-TrioctanoylglycerolChEBI
AxonaChEBI
Caprylic acid triglycerideChEBI
Caprylic acid, 1,2,3-propanetriyl esterChEBI
Caprylic triglycerideChEBI
CaprylinChEBI
Glycerin tricaprylateChEBI
Glycerol tricaprylateChEBI
Glycerol trioctanoateChEBI
Glycerol trioctanoinChEBI
Glyceryl tricaprylateChEBI
Octanoic acid triglycerideChEBI
Octanoic acid, 1,1',1''-(1,2,3-propanetriyl) esterChEBI
Octanoic acid, 1,2,3-propanetriyl esterChEBI
TricaprilinChEBI
Tricaprylic glycerideChEBI
TricaprylinChEBI
TricapryloylglycerolChEBI
Tricaprylyl glycerinChEBI
TrioctanoylglycerideChEBI
TrioctanoylglycerolChEBI
1,2,3-Propanetriol trioctanoic acidGenerator
Caprylate triglycerideGenerator
Caprylate, 1,2,3-propanetriyl esterGenerator
Glycerin tricaprylic acidGenerator
Glycerol tricaprylic acidGenerator
Glycerol trioctanoic acidGenerator
Glyceryl tricaprylic acidGenerator
Octanoate triglycerideGenerator
Octanoate, 1,1',1''-(1,2,3-propanetriyl) esterGenerator
Octanoate, 1,2,3-propanetriyl esterGenerator
2-Ethylhexanoic acid, 1,2,3-propanetriyl esterMeSH
Panasate 800MeSH
Glyceryl trioctanoateMeSH
Octanoic acid, 1,2,3- propanetriyl esterMeSH
TriethylhexanoinMeSH
TrioctanoinMeSH
1-capryloyl-2-capryloyl-3-capryloyl-glycerolLipid Annotator, HMDB
TAG(8:0/8:0/8:0)Lipid Annotator, HMDB
TAG(24:0)Lipid Annotator, HMDB
Tracylglycerol(24:0)Lipid Annotator, HMDB
TriacylglycerolLipid Annotator, HMDB
TriglycerideLipid Annotator, HMDB
TG(24:0)Lipid Annotator, HMDB
1-octanoyl-2-octanoyl-3-octanoyl-glycerolLipid Annotator, HMDB
Tracylglycerol(8:0/8:0/8:0)Lipid Annotator, HMDB
TG(8:0/8:0/8:0)Lipid Annotator, ChEBI
Chemical FormulaC27H50O6
Average Molecular Mass470.682 g/mol
Monoisotopic Mass470.361 g/mol
CAS Registry Number538-23-8
IUPAC Name1,3-bis(octanoyloxy)propan-2-yl octanoate
Traditional NameRato
SMILES[H]C(COC(=O)CCCCCCC)(COC(=O)CCCCCCC)OC(=O)CCCCCCC
InChI IdentifierInChI=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
InChI KeyVLPFTAMPNXLGLX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassTriradylcglycerols
Direct ParentTriacylglycerols
Alternative Parents
Substituents
  • Triacyl-sn-glycerol
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.4e-05 g/LALOGPS
logP7.41ALOGPS
logP8.25ChemAxon
logS-6.9ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity130.87 m³·mol⁻¹ChemAxon
Polarizability57.31 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-2ec19e7d19282502723bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-2ec19e7d19282502723bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-0009700000-74eec0b6f556539a1960Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-b234d06f8a74d84a1ec8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-b234d06f8a74d84a1ec8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00b9-0109700000-95dc0351f8ea2f8fc008Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000900000-ed09fdff10743d8648cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0000900000-ed09fdff10743d8648cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uji-0909900000-7a2f04eb34118f1dfeddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00fr-0205900000-ebdc13d71ea6e7ed7fb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ufs-3988600000-ab2ef16f12938610e275Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ugj-5942000000-025420f6cf19090c67b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000900000-65c575fb46b6dd8d287cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000900000-65c575fb46b6dd8d287cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0000900000-65c575fb46b6dd8d287cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00mo-0916400000-ec4e89b54212438d375cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0096-0901000000-d3d63ccae972b08be42aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0900000000-96575af340fc74287e24Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12176
HMDB IDHMDB0011187
FooDB IDFDB003135
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAxona
Chemspider ID10393
ChEBI ID76978
PubChem Compound ID10850
Kegg Compound IDC13044
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=100603
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=21262136
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24169853
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=3752242
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=6616756
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=884170
7. Fendri A, Louati H, Sellami M, Gargouri H, Smichi N, Zarai Z, Aissa I, Miled N, Gargouri Y: A thermoactive uropygial esterase from chicken: purification, characterisation and synthesis of flavour esters. Int J Biol Macromol. 2012 Jun 1;50(5):1238-44. doi: 10.1016/j.ijbiomac.2012.04.008. Epub 2012 Apr 13.
8. Messaoudi A, Belguith H, Ben Hamida J: Three-Dimensional Structure of Arabidopsis thaliana Lipase Predicted by Homology Modeling Method. Evol Bioinform Online. 2011;7:99-105. doi: 10.4137/EBO.S7122. Epub 2011 Jun 28.
9. Tetrick MA, Greer FR, Benevenga NJ: Blood D-(-)-3-hydroxybutyrate concentrations after oral administration of trioctanoin, trinonanoin, or tridecanoin to newborn rhesus monkeys (Macaca mulatta). Comp Med. 2010 Dec;60(6):486-90.
10. Mateos-Diaz E, Rodriguez JA, de Los Angeles Camacho-Ruiz M, Mateos-Diaz JC: High-throughput screening method for lipases/esterases. Methods Mol Biol. 2012;861:89-100. doi: 10.1007/978-1-61779-600-5_5.
11. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
12. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
13. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
14. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
15. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
16. The lipid handbook with CD-ROM
17. Triglycerides and Cholesterol Research