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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:04:02 UTC
Update Date2022-03-07 02:54:02 UTC
HMDB IDHMDB0034263
Secondary Accession Numbers
  • HMDB34263
Metabolite Identification
Common NameTriethyl citrate
DescriptionTriethyl citrate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. Triethyl citrate is a mild, fruity, and odorless tasting compound. Based on a literature review a significant number of articles have been published on Triethyl citrate.
Structure
Data?1563862536
Synonyms
ValueSource
Triethyl citric acidGenerator
e1505ChEMBL, HMDB
1,2,3-Propanetricarboxylic acid, 2-hydroxy-, triethyl esterHMDB
2-Hydroxy-1,2,3-propanetricarboxylic acid, triethyl esterHMDB
Citric acid, triethyl esterHMDB
Citroflex 2HMDB
Crodamol TCHMDB
Ethyl citrateHMDB, MeSH
Ethyl citrate, citric acid triethyl esterHMDB
EudraflexHMDB
FEMA 3083HMDB
Hydagen c.a.tHMDB
Hydragen catHMDB
TECHMDB
TriaethylcitratHMDB
Triethyl 2-hydroxy-1,2,3-propanetricarboxylateHMDB
Triethyl citrate (NF)HMDB
Triethylester kyseliny citronoveHMDB
Uniflex tecHMDB
Uniplex 80HMDB
Chemical FormulaC12H20O7
Average Molecular Weight276.283
Monoisotopic Molecular Weight276.120902994
IUPAC Name1,2,3-triethyl 2-hydroxypropane-1,2,3-tricarboxylate
Traditional Nametriethyl citrate
CAS Registry Number77-93-0
SMILES
CCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC
InChI Identifier
InChI=1S/C12H20O7/c1-4-17-9(13)7-12(16,11(15)19-6-3)8-10(14)18-5-2/h16H,4-8H2,1-3H3
InChI KeyDOOTYTYQINUNNV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Tertiary alcohol
  • Carboxylic acid ester
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point127.00 °C. @ 1.00 mm HgThe Good Scents Company Information System
Water Solubility65 mg/mLNot Available
LogP1.267 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility10.7 g/LALOGPS
logP1.17ALOGPS
logP0.19ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)11.82ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area99.13 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity64.18 m³·mol⁻¹ChemAxon
Polarizability27.83 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]+165.66631661259
DarkChem[M-H]-161.78731661259
DeepCCS[M+H]+160.08930932474
DeepCCS[M-H]-157.73130932474
DeepCCS[M-2H]-190.82330932474
DeepCCS[M+Na]+166.18230932474
AllCCS[M+H]+164.932859911
AllCCS[M+H-H2O]+161.832859911
AllCCS[M+NH4]+167.832859911
AllCCS[M+Na]+168.632859911
AllCCS[M-H]-163.532859911
AllCCS[M+Na-2H]-164.332859911
AllCCS[M+HCOO]-165.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Triethyl citrateCCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC2955.4Standard polar33892256
Triethyl citrateCCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC1542.4Standard non polar33892256
Triethyl citrateCCOC(=O)CC(O)(CC(=O)OCC)C(=O)OCC1779.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Triethyl citrate,1TMS,isomer #1CCOC(=O)CC(CC(=O)OCC)(O[Si](C)(C)C)C(=O)OCC1786.1Semi standard non polar33892256
Triethyl citrate,1TBDMS,isomer #1CCOC(=O)CC(CC(=O)OCC)(O[Si](C)(C)C(C)(C)C)C(=O)OCC2006.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Triethyl citrate EI-B (Non-derivatized)splash10-0a4i-1920000000-f7c884b67f54e12797d92017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Triethyl citrate EI-B (Non-derivatized)splash10-0a4i-0910000000-9ead4713599bcc551b122017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Triethyl citrate CI-B (Non-derivatized)splash10-004i-0190000000-7b8558c43641df82df602017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Triethyl citrate EI-B (Non-derivatized)splash10-0a4i-1920000000-f7c884b67f54e12797d92018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Triethyl citrate EI-B (Non-derivatized)splash10-0a4i-0910000000-9ead4713599bcc551b122018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Triethyl citrate CI-B (Non-derivatized)splash10-004i-0190000000-7b8558c43641df82df602018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Triethyl citrate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ufr-5890000000-e53cab1b65097a22eedf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Triethyl citrate GC-MS (1 TMS) - 70eV, Positivesplash10-004i-5092000000-6e3fc95af9f04950f62f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Triethyl citrate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0a6r-7910000000-e1114c0c65a16dd49eeb2014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate LC-ESI-ITFT , positive-QTOFsplash10-05o9-0900000000-abe5dcdf0bae8dc9ed542017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate LC-ESI-ITFT , positive-QTOFsplash10-03dr-1900000000-9aa32164a05037b216222017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate LC-ESI-ITFT , positive-QTOFsplash10-0zfr-0790000000-eaf06e927ea1ee1440b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate LC-ESI-ITFT , positive-QTOFsplash10-0zfr-0890000000-babd242488f267e298172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate LC-ESI-QFT , positive-QTOFsplash10-0a4i-0900000000-550d7ef825027f130a1e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate 35V, Positive-QTOFsplash10-0a4i-0900000000-bcaf65f04f030fc362db2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate 30V, Positive-QTOFsplash10-0a4i-0900000000-09a16a64d8b6a8409c0d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate 40V, Positive-QTOFsplash10-052r-0900000000-f5da78fc91309994cf252021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate 20V, Positive-QTOFsplash10-0a4i-0900000000-fed064182d82b13afe812021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate 10V, Positive-QTOFsplash10-0pb9-0960000000-ecc9db61ae907f31c6d82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Triethyl citrate 50V, Positive-QTOFsplash10-000i-0900000000-595e183f161fb191ea182021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 10V, Positive-QTOFsplash10-004r-0790000000-8052cd9aa829d3b3770a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 20V, Positive-QTOFsplash10-000i-9610000000-9ac2305d61fe7cc529e82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 40V, Positive-QTOFsplash10-069a-3910000000-5dd15a26bff8e43df3ef2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 10V, Negative-QTOFsplash10-004r-1960000000-62c3e6b4cc939bf1a2842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 20V, Negative-QTOFsplash10-002u-6950000000-29afe05fe47ce4f750242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 40V, Negative-QTOFsplash10-0a6s-8910000000-6dde72620e6bfe59a9e22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 10V, Positive-QTOFsplash10-004i-0090000000-f2deb2e421d123b4795f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 20V, Positive-QTOFsplash10-0a59-2390000000-8b8d674209f59fa49d882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 40V, Positive-QTOFsplash10-0005-9400000000-aa1936e1a6ab993057a42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 10V, Negative-QTOFsplash10-002r-5590000000-470583cc7469f45edd1a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 20V, Negative-QTOFsplash10-002r-0930000000-90a982ba5053949631d12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triethyl citrate 40V, Negative-QTOFsplash10-0a59-5900000000-a44b708dde613f9095562021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB012587
KNApSAcK IDNot Available
Chemspider ID13850879
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTriethyl citrate
METLIN IDNot Available
PubChem Compound6506
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012772
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .