GLYCEROL TRIBUTYRATE (CHEM005860)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:07:18 UTC
Update Date2016-11-09 01:09:37 UTC
Accession NumberCHEM005860
Identification
Common NameGLYCEROL TRIBUTYRATE
ClassSmall Molecule
DescriptionA triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by butyric acid.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,2,3-Propanetriol, tributyrateChEBI
1,2,3-Propanetriyl tributanoateChEBI
1,2,3-TributanoylglycerolChEBI
1,2,3-TributyrylglycerolChEBI
2,3-Bis(butyryloxy)propyl butyrateChEBI
Butanoic acid, 1,2,3-propanetriyl esterChEBI
ButyrinChEBI
Butyryl triglycerideChEBI
Glycerin tributyrateChEBI
Glycerol tributyrateChEBI
GlyceroltributyrinChEBI
Glyceryl tributyrateChEBI
Propane-1,2,3-triyl tributyrateChEBI
Tri-N-butyrinChEBI
TributinChEBI
Tributyryl glycerideChEBI
1,2,3-Propanetriol, tributyric acidGenerator
1,2,3-Propanetriyl tributanoic acidGenerator
2,3-Bis(butyryloxy)propyl butyric acidGenerator
Butanoate, 1,2,3-propanetriyl esterGenerator
Glycerin tributyric acidGenerator
Glycerol tributyric acidGenerator
Glyceryl tributyric acidGenerator
Propane-1,2,3-triyl tributyric acidGenerator
Glycerol tributanoic acidGenerator
TributyrylglycerolMeSH
Butyric acid triester with glycerinHMDB
FEMA 2223HMDB
KodaflexHMDB
NSC 661583HMDB
Tri-butyrinHMDB
TributyrinHMDB
TributyrinineHMDB
Tributyrl glycerideHMDB
TributyroinHMDB
Glycerol tributanoateChEBI
Chemical FormulaC15H26O6
Average Molecular Mass302.363 g/mol
Monoisotopic Mass302.173 g/mol
CAS Registry Number60-01-5
IUPAC Name1,3-bis(butanoyloxy)propan-2-yl butanoate
Traditional Nametributyrin
SMILESCCCC(=O)OCC(COC(=O)CCC)OC(=O)CCC
InChI IdentifierInChI=1S/C15H26O6/c1-4-7-13(16)19-10-12(21-15(18)9-6-3)11-20-14(17)8-5-2/h12H,4-11H2,1-3H3
InChI KeyUYXTWWCETRIEDR-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 Solubility0.32 g/LALOGPS
logP2.71ALOGPS
logP2.92ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity75.65 m³·mol⁻¹ChemAxon
Polarizability32.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9100000000-a0f9426f5cd5d1ad3c83Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9110000000-053a735053ae0621fe88Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9100000000-a0f9426f5cd5d1ad3c83Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-00di-9110000000-053a735053ae0621fe88Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-c4d130796e01a45caadaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-c4d130796e01a45caadaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-0097000000-b93aef222c9f718aa3b2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-38db4a07206d84284415Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0009000000-38db4a07206d84284415Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ai2-9099000000-12c3d7bdd61a16d085a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0459000000-babf77e8c5a51a5e69ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0v00-2953000000-f878b874e5b39892ae4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00ds-8900000000-a1b857778d6727f6a47bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-1e1f8e781385aeed294dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-1e1f8e781385aeed294dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-1097000000-9e038df610fe764fc17eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gw0-9756000000-9862c21f5688e05dd3b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9800000000-48475bab8381d831aee3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-6900000000-acef2739fe3f4e2cd066Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-ab75fe3f6e5f939e6f27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-ab75fe3f6e5f939e6f27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-0009000000-ab75fe3f6e5f939e6f27Spectrum
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 IDDB12709
HMDB IDHMDB0031094
FooDB IDFDB003099
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-13014
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkButyrin
Chemspider ID13849665
ChEBI ID35020
PubChem Compound ID6050
Kegg Compound IDC13870
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=23568954
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23630018
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23887917
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24121865
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24302446
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24506942
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24576724
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24890666
9. Kobayashi R, Hirano N, Kanaya S, Haruki M: Enhancement of the enzymatic activity of Escherichia coli acetyl esterase by a double mutation obtained by random mutagenesis. Biosci Biotechnol Biochem. 2012;76(11):2082-8. Epub 2012 Nov 7.
10. Lookene A, Bengtsson-Olivecrona G: Chymotryptic cleavage of lipoprotein lipase. Identification of cleavage sites and functional studies of the truncated molecule. Eur J Biochem. 1993 Apr 1;213(1):185-94.
11. Biver S, Vandenbol M: Characterization of three new carboxylic ester hydrolases isolated by functional screening of a forest soil metagenomic library. J Ind Microbiol Biotechnol. 2013 Feb;40(2):191-200. doi: 10.1007/s10295-012-1217-7. Epub 2012 Nov 18.
12. Feng X, Patterson DA, Balaban M, Emanuelsson EA: Enabling the utilization of wool as an enzyme support: enhancing the activity and stability of lipase immobilized onto woolen cloth. Colloids Surf B Biointerfaces. 2013 Feb 1;102:526-33. doi: 10.1016/j.colsurfb.2012.08.037. Epub 2012 Sep 4.
13. Lesot P, Serhan Z, Aroulanda C, Billault I: Analytical contribution of NAD 2D-NMR spectroscopy in polypeptide mesophases to the investigation of triglycerides. Magn Reson Chem. 2012 Dec;50 Suppl 1:S2-11. doi: 10.1002/mrc.3855.
14. Heidor R, Ortega JF, de Conti A, Ong TP, Moreno FS: Anticarcinogenic actions of tributyrin, a butyric acid prodrug. Curr Drug Targets. 2012 Dec;13(14):1720-9.
15. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
16. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
17. 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.
18. 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.
19. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
20. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
21. The lipid handbook with CD-ROM
22. Triglycerides and Cholesterol Research