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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:59:31 UTC
Update Date2022-03-07 02:56:14 UTC
HMDB IDHMDB0039511
Secondary Accession Numbers
  • HMDB39511
Metabolite Identification
Common NameBenzoyl meso-tartaric acid
DescriptionBenzoyl meso-tartaric acid belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid. Benzoyl meso-tartaric acid has been detected, but not quantified in, pulses. This could make benzoyl meso-tartaric acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Benzoyl meso-tartaric acid.
Structure
Data?1563863389
Synonyms
ValueSource
Benzoyl meso-tartarateGenerator
2-(Benzoyloxy)-3-hydroxybutanedioateHMDB
Chemical FormulaC11H10O7
Average Molecular Weight254.1929
Monoisotopic Molecular Weight254.042652674
IUPAC Name2-(benzoyloxy)-3-hydroxybutanedioic acid
Traditional Name2-(benzoyloxy)-3-hydroxybutanedioic acid
CAS Registry Number65621-34-3
SMILES
OC(C(OC(=O)C1=CC=CC=C1)C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C11H10O7/c12-7(9(13)14)8(10(15)16)18-11(17)6-4-2-1-3-5-6/h1-5,7-8,12H,(H,13,14)(H,15,16)
InChI KeyJXXURQWKKCNUBH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Tricarboxylic acid or derivatives
  • Benzoyl
  • Sugar acid
  • Beta-hydroxy acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point192 - 196 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.67 g/LALOGPS
logP0.86ALOGPS
logP0.67ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.03ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity56.04 m³·mol⁻¹ChemAxon
Polarizability22.73 ųChemAxon
Number of Rings1ChemAxon
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]+157.3331661259
DarkChem[M-H]-152.41631661259
DeepCCS[M+H]+151.16930932474
DeepCCS[M-H]-148.81130932474
DeepCCS[M-2H]-181.72830932474
DeepCCS[M+Na]+157.26230932474
AllCCS[M+H]+155.532859911
AllCCS[M+H-H2O]+152.032859911
AllCCS[M+NH4]+158.832859911
AllCCS[M+Na]+159.732859911
AllCCS[M-H]-152.432859911
AllCCS[M+Na-2H]-152.432859911
AllCCS[M+HCOO]-152.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Benzoyl meso-tartaric acidOC(C(OC(=O)C1=CC=CC=C1)C(O)=O)C(O)=O3541.4Standard polar33892256
Benzoyl meso-tartaric acidOC(C(OC(=O)C1=CC=CC=C1)C(O)=O)C(O)=O2059.7Standard non polar33892256
Benzoyl meso-tartaric acidOC(C(OC(=O)C1=CC=CC=C1)C(O)=O)C(O)=O2050.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benzoyl meso-tartaric acid,1TMS,isomer #1C[Si](C)(C)OC(C(=O)O)C(OC(=O)C1=CC=CC=C1)C(=O)O2117.2Semi standard non polar33892256
Benzoyl meso-tartaric acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(OC(=O)C1=CC=CC=C1)C(O)C(=O)O2122.8Semi standard non polar33892256
Benzoyl meso-tartaric acid,1TMS,isomer #3C[Si](C)(C)OC(=O)C(O)C(OC(=O)C1=CC=CC=C1)C(=O)O2109.5Semi standard non polar33892256
Benzoyl meso-tartaric acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(O[Si](C)(C)C)C(OC(=O)C1=CC=CC=C1)C(=O)O2125.8Semi standard non polar33892256
Benzoyl meso-tartaric acid,2TMS,isomer #2C[Si](C)(C)OC(=O)C(OC(=O)C1=CC=CC=C1)C(O[Si](C)(C)C)C(=O)O2118.2Semi standard non polar33892256
Benzoyl meso-tartaric acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C(O)C(OC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C2081.7Semi standard non polar33892256
Benzoyl meso-tartaric acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C(OC(=O)C1=CC=CC=C1)C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C2109.8Semi standard non polar33892256
Benzoyl meso-tartaric acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(C(=O)O)C(OC(=O)C1=CC=CC=C1)C(=O)O2330.7Semi standard non polar33892256
Benzoyl meso-tartaric acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)C1=CC=CC=C1)C(O)C(=O)O2341.2Semi standard non polar33892256
Benzoyl meso-tartaric acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)C(OC(=O)C1=CC=CC=C1)C(=O)O2332.1Semi standard non polar33892256
Benzoyl meso-tartaric acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(O[Si](C)(C)C(C)(C)C)C(OC(=O)C1=CC=CC=C1)C(=O)O2560.9Semi standard non polar33892256
Benzoyl meso-tartaric acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)C1=CC=CC=C1)C(O[Si](C)(C)C(C)(C)C)C(=O)O2561.5Semi standard non polar33892256
Benzoyl meso-tartaric acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(O)C(OC(=O)C1=CC=CC=C1)C(=O)O[Si](C)(C)C(C)(C)C2548.9Semi standard non polar33892256
Benzoyl meso-tartaric acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(OC(=O)C1=CC=CC=C1)C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2749.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benzoyl meso-tartaric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-4910000000-7667c7ce151ed04c2bc32017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoyl meso-tartaric acid GC-MS (3 TMS) - 70eV, Positivesplash10-0aor-4913000000-c7890770b1659250faf02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benzoyl meso-tartaric acid 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 - Benzoyl meso-tartaric acid 10V, Positive-QTOFsplash10-0a4r-0690000000-3499df0db1e59779f4e72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 20V, Positive-QTOFsplash10-0a4i-1940000000-854edbe66405d8f9de7a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 40V, Positive-QTOFsplash10-0a4i-4900000000-82f9abceceb5bcbb8b3e2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 10V, Negative-QTOFsplash10-0pk9-2980000000-667f2ee86577859288ba2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 20V, Negative-QTOFsplash10-05fr-4940000000-996f5386843d104da2da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 40V, Negative-QTOFsplash10-0200-7900000000-a8b5cb9e77c8aae73a3b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 10V, Negative-QTOFsplash10-000i-9100000000-c3630a6d191ebf70c79e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 20V, Negative-QTOFsplash10-000i-9200000000-ab137a5dd2c050fcb5732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 40V, Negative-QTOFsplash10-004r-9000000000-1db2c8111d0665e62d742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 10V, Positive-QTOFsplash10-0a4i-0920000000-252fb06d2070cd3ef5ca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 20V, Positive-QTOFsplash10-0a6r-4900000000-153aef3172df079a24612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benzoyl meso-tartaric acid 40V, Positive-QTOFsplash10-0a4i-6900000000-71010ea9d36372cf5e632021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart 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 IDFDB019121
KNApSAcK IDC00054033
Chemspider ID15302874
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13708642
PDB IDNot Available
ChEBI ID174347
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.. .