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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:52:18 UTC
Update Date2022-03-07 02:53:29 UTC
HMDB IDHMDB0032857
Secondary Accession Numbers
  • HMDB32857
Metabolite Identification
Common NameGlycerol tripropanoate
DescriptionGlycerol tripropanoate, also known as glycerol tripropionic acid or 1,2,3-tripropanoylglycerol, 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. Based on a literature review a significant number of articles have been published on Glycerol tripropanoate.
Structure
Data?1563862318
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 Weight260.2836
Monoisotopic Molecular Weight260.125988372
IUPAC Name1,3-bis(propanoyloxy)propan-2-yl propanoate
Traditional Nametripropionin
CAS Registry Number139-45-7
SMILES
CCC(=O)OCC(COC(=O)CC)OC(=O)CC
InChI Identifier
InChI=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
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point175.00 to 176.00 °C. @ 20.00 mm HgThe Good Scents Company Information System
Water Solubility3.07 mg/mL at 37 °CNot Available
LogP1.745 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+162.56431661259
DarkChem[M-H]-158.49731661259
DeepCCS[M+H]+162.89130932474
DeepCCS[M-H]-160.53330932474
DeepCCS[M-2H]-194.13630932474
DeepCCS[M+Na]+169.09330932474
AllCCS[M+H]+164.532859911
AllCCS[M+H-H2O]+161.432859911
AllCCS[M+NH4]+167.332859911
AllCCS[M+Na]+168.132859911
AllCCS[M-H]-159.932859911
AllCCS[M+Na-2H]-160.832859911
AllCCS[M+HCOO]-161.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Glycerol tripropanoateCCC(=O)OCC(COC(=O)CC)OC(=O)CC2487.8Standard polar33892256
Glycerol tripropanoateCCC(=O)OCC(COC(=O)CC)OC(=O)CC1552.8Standard non polar33892256
Glycerol tripropanoateCCC(=O)OCC(COC(=O)CC)OC(=O)CC1697.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Glycerol tripropanoate EI-B (Non-derivatized)splash10-0a4i-9400000000-a0a6aa29bbc356c639312017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycerol tripropanoate EI-B (Non-derivatized)splash10-0a4i-9000000000-395760d45c9442f98c2e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycerol tripropanoate EI-B (Non-derivatized)splash10-0a4i-9400000000-a0a6aa29bbc356c639312018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Glycerol tripropanoate EI-B (Non-derivatized)splash10-0a4i-9000000000-395760d45c9442f98c2e2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerol tripropanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Glycerol tripropanoate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 10V, Positive-QTOFsplash10-004i-0090000000-e255af8673c1a3e6e2ae2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 20V, Positive-QTOFsplash10-004i-0090000000-e255af8673c1a3e6e2ae2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 40V, Positive-QTOFsplash10-01p9-0970000000-26256e73865319ca134d2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 10V, Positive-QTOFsplash10-001i-0090000000-96e4787f4c0ad9f150672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 20V, Positive-QTOFsplash10-001i-0090000000-96e4787f4c0ad9f150672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 40V, Positive-QTOFsplash10-001i-0090000000-96e4787f4c0ad9f150672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 10V, Positive-QTOFsplash10-014i-0090000000-4239986e4d797ec22e1a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 20V, Positive-QTOFsplash10-014i-0090000000-4239986e4d797ec22e1a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 40V, Positive-QTOFsplash10-0166-9990000000-90e8990e72debe46c8192021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 10V, Positive-QTOFsplash10-03di-0390000000-7f3b56ccd60cd915e83a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 20V, Positive-QTOFsplash10-03gi-1930000000-c26c1f2e4117623b8e6b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 40V, Positive-QTOFsplash10-01si-4900000000-5cbb9368e934ac8a946d2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 10V, Positive-QTOFsplash10-004i-0090000000-edd8de00dc3985168e092021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 20V, Positive-QTOFsplash10-004i-0090000000-edd8de00dc3985168e092021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 40V, Positive-QTOFsplash10-01p9-1970000000-ca5c9d27b429369bcb942021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 10V, Negative-QTOFsplash10-0002-2940000000-9db7ce1eb8c921cb0c152021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 20V, Negative-QTOFsplash10-00di-9400000000-5b0b726f9f9ccb185dc62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Glycerol tripropanoate 40V, Negative-QTOFsplash10-00di-9400000000-134c271f572496e020942021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010834
KNApSAcK IDNot Available
Chemspider ID8433
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound8763
PDB IDNot Available
ChEBI ID88153
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1025161
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
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  2. 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. [PubMed:9822688 ]
  3. 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. [PubMed:4985219 ]
  4. 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. [PubMed:15837431 ]
  5. 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. [PubMed:10518741 ]
  6. 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. [PubMed:16780787 ]
  7. 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. [PubMed:20655391 ]
  8. 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 . [PubMed:18382924 ]
  9. 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. [PubMed:11170561 ]
  10. 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. [PubMed:12117564 ]
  11. Sayari A, Mejdoub H, Gargouri Y: Characterization of turkey pancreatic lipase. Biochimie. 2000 Feb;82(2):153-9. [PubMed:10727771 ]
  12. 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. [PubMed:10669782 ]
  13. 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. [PubMed:16842350 ]
  14. Sayari A, Agrebi N, Jaoua S, Gargouri Y: Biochemical and molecular characterization of Staphylococcus simulans lipase. Biochimie. 2001 Sep;83(9):863-71. [PubMed:11698108 ]
  15. 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. [PubMed:9501519 ]
  16. 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. [PubMed:11750885 ]
  17. Lombardo D, Guy O: Binding of human pancreatic carboxylic ester hydrolase to lipid interfaces. Biochim Biophys Acta. 1981 Jun 15;659(2):401-10. [PubMed:7260101 ]
  18. 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. [PubMed:12216836 ]
  19. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  20. 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. [PubMed:16902246 ]
  21. 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. [PubMed:17374880 ]
  22. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  23. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
  24. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  25. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  26. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..