GLYCERYL TRIPROPANOATE (CHEM005870)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-19 02:07:24 UTC
Update Date2016-11-09 01:09:37 UTC
Accession NumberCHEM005870
Identification
Common NameGLYCERYL TRIPROPANOATE
ClassSmall Molecule
DescriptionA triglyceride obtained by formal acylation of the three hydroxy groups of glycerol by propionic acid.
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3-Propanetriol tripropanoateChEBI
1,2,3-TripropanoylglycerolChEBI
2,3-Di(propanoyloxy)propyl propanoateChEBI
Glycerine tripropionateChEBI
Glycerol tripropionateChEBI
Glyceryl tripropanoateChEBI
Glyceryl tripropionateChEBI
TripropionylglycerolChEBI
1,2,3-Propanetriol tripropanoic acidGenerator
2,3-Di(propanoyloxy)propyl propanoic acidGenerator
Glycerine tripropionic acidGenerator
Glycerol tripropionic acidGenerator
Glyceryl tripropanoic acidGenerator
Glyceryl tripropionic acidGenerator
Glycerol tripropanoic acidGenerator
1,2,3-Propanetriol tripropanoate, 9ciHMDB
1,2,3-Propanetriol, 1,2,3-tripropanoateHMDB
1,2,3-Propanetriol, tripropanoateHMDB
1,2,3-Propanetriol, tripropionateHMDB
2,3-Bis(propionyloxy)propyl propionateHMDB
FEMA 3286HMDB
Propionic acid triglycerideHMDB
Propionin, tri- (8ci)HMDB
Tri-propioninHMDB
TripropioninHMDB
Tripropionin, 8ciHMDB
TripropionineHMDB
Chemical FormulaC12H20O6
Average Molecular Mass260.284 g/mol
Monoisotopic Mass260.126 g/mol
CAS Registry Number139-45-7
IUPAC Name1,3-bis(propanoyloxy)propan-2-yl propanoate
Traditional Nametripropionin
SMILESCCC(=O)OCC(COC(=O)CC)OC(=O)CC
InChI IdentifierInChI=1S/C12H20O6/c1-4-10(13)16-7-9(18-12(15)6-3)8-17-11(14)5-2/h9H,4-8H2,1-3H3
InChI KeyYZWRNSARCRTXDS-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
  • 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 DescriptorsNot Available
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 Solubility5.45 g/LALOGPS
logP1.69ALOGPS
logP1.59ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)-6.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area78.9 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity61.85 m³·mol⁻¹ChemAxon
Polarizability27.12 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)splash10-0a4i-9400000000-a0a6aa29bbc356c63931Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-395760d45c9442f98c2eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9400000000-a0a6aa29bbc356c63931Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9000000000-395760d45c9442f98c2eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-e255af8673c1a3e6e2aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-e255af8673c1a3e6e2aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-0970000000-26256e73865319ca134dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-96e4787f4c0ad9f15067Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0090000000-96e4787f4c0ad9f15067Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0090000000-96e4787f4c0ad9f15067Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0090000000-4239986e4d797ec22e1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0090000000-4239986e4d797ec22e1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0166-9990000000-90e8990e72debe46c819Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0390000000-7f3b56ccd60cd915e83aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-1930000000-c26c1f2e4117623b8e6bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01si-4900000000-5cbb9368e934ac8a946dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-edd8de00dc3985168e09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0090000000-edd8de00dc3985168e09Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-1970000000-ca5c9d27b429369bcb94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-2940000000-9db7ce1eb8c921cb0c15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9400000000-5b0b726f9f9ccb185dc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-9400000000-134c271f572496e02094Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
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 IDNot Available
HMDB IDHMDB0032857
FooDB IDFDB010834
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8433
ChEBI ID88153
PubChem Compound ID8763
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11750885
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12216836
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=15373841
4. Roussel A, Yang Y, Ferrato F, Verger R, Cambillau C, Lowe M: Structure and activity of rat pancreatic lipase-related protein 2. J Biol Chem. 1998 Nov 27;273(48):32121-8.
5. Vermorel M: [Energetic utilization of tripropionine by growing rats]. C R Acad Sci Hebd Seances Acad Sci D. 1970 Jan 12;270(2):400-2.
6. Mosbah H, Sayari A, Mejdoub H, Dhouib H, Gargouri Y: Biochemical and molecular characterization of Staphylococcus xylosus lipase. Biochim Biophys Acta. 2005 May 25;1723(1-3):282-91. Epub 2005 Mar 22.
7. Oh B, Kim H, Lee J, Kang S, Oh T: Staphylococcus haemolyticus lipase: biochemical properties, substrate specificity and gene cloning. FEMS Microbiol Lett. 1999 Oct 15;179(2):385-92.
8. Fendri A, Frikha F, Mosbah H, Miled N, Zouari N, Bacha AB, Sayari A, Mejdoub H, Gargouri Y: Biochemical characterization, cloning, and molecular modelling of chicken pancreatic lipase. Arch Biochem Biophys. 2006 Jul 15;451(2):149-59. Epub 2006 May 17.
9. Chahinian H, Fantini J, Garmy N, Manco G, Sarda L: Non-lipolytic and lipolytic sequence-related carboxylesterases: a comparative study of the structure-function relationships of rabbit liver esterase 1 and bovine pancreatic bile-salt-activated lipase. Biochim Biophys Acta. 2010 Nov;1801(11):1195-204. doi: 10.1016/j.bbalip.2010.07.002. Epub 2010 Jul 22.
10. Breguet V, Vojinovic V, Von Stockar U, Marison IW: Enzymatic hydrolysis of organic-core microcapsules to produce aqueous-core microcapsules. J Microencapsul. 2008 May;25(3):179-86. doi: 10.1080/02652040701843461 .
11. Weber N, Weitkamp P, Mukherjee KD: Fatty acid steryl, stanyl, and steroid esters by esterification and transesterification in vacuo using Candida rugosa lipase as catalyst. J Agric Food Chem. 2001 Jan;49(1):67-71.
12. Kim HK, Choi HJ, Kim MH, Sohn CB, Oh TK: Expression and characterization of Ca(2+)-independent lipase from Bacillus pumilus B26. Biochim Biophys Acta. 2002 Jul 11;1583(2):205-12.
13. Sayari A, Mejdoub H, Gargouri Y: Characterization of turkey pancreatic lipase. Biochimie. 2000 Feb;82(2):153-9.
14. Granon S, Semeriva M: Effect of taurodeoxycholate, colipase and temperature on the interfacial inactivation of porcine pancreatic lipase. Eur J Biochem. 1980 Oct;111(1):117-24.
15. Miled N, De Caro A, De Caro J, Verger R: A conformational transition between an open and closed form of human pancreatic lipase revealed by a monoclonal antibody. Biochim Biophys Acta. 2000 Feb 9;1476(2):165-72.
16. Salah RB, Mosbah H, Fendri A, Gargouri A, Gargouri Y, Mejdoub H: Biochemical and molecular characterization of a lipase produced by Rhizopus oryzae. FEMS Microbiol Lett. 2006 Jul;260(2):241-8.
17. Sayari A, Agrebi N, Jaoua S, Gargouri Y: Biochemical and molecular characterization of Staphylococcus simulans lipase. Biochimie. 2001 Sep;83(9):863-71.
18. Kim HK, Park SY, Lee JK, Oh TK: Gene cloning and characterization of thermostable lipase from Bacillus stearothermophilus L1. Biosci Biotechnol Biochem. 1998 Jan;62(1):66-71.
19. Nini L, Sarda L, Comeau LC, Boitard E, Dubes JP, Chahinian H: Lipase-catalysed hydrolysis of short-chain substrates in solution and in emulsion: a kinetic study. Biochim Biophys Acta. 2001 Nov 30;1534(1):34-44.
20. Lombardo D, Guy O: Binding of human pancreatic carboxylic ester hydrolase to lipid interfaces. Biochim Biophys Acta. 1981 Jun 15;659(2):401-10.
21. Chahinian H, Nini L, Boitard E, Dubes JP, Comeau LC, Sarda L: Distinction between esterases and lipases: a kinetic study with vinyl esters and TAG. Lipids. 2002 Jul;37(7):653-62.
22. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
23. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
24. 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.
25. 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.
26. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
27. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
28. The lipid handbook with CD-ROM
29. Triglycerides and Cholesterol Research