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Showing Compound Monocaffeoyl(-)-tartaric acid (FDB021421)

Record Information
Version1.0
Creation date2010-04-08 22:15:41 UTC
Update date2019-11-26 03:20:21 UTC
Primary IDFDB021421
Secondary Accession Numbers
  • FDB018772
Chemical Information
FooDB NameMonocaffeoyl(-)-tartaric acid
DescriptionMonocaffeoyl(-)-tartaric acid belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Monocaffeoyl(-)-tartaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Monocaffeoyl(-)-tartaric acid has been detected, but not quantified in, green vegetables. This could make monocaffeoyl(-)-tartaric acid a potential biomarker for the consumption of these foods.
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Monocaffeoyl(-)-tartarateGenerator
Monocaffeoyl(-)-tartaric aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP1.68ALOGPS
logP0.6ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)2.96ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area161.59 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity69.74 m³·mol⁻¹ChemAxon
Polarizability28.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC13H12O9
IUPAC name2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid
InChI IdentifierInChI=1S/C13H12O9/c14-7-3-1-6(5-8(7)15)2-4-9(16)22-11(13(20)21)10(17)12(18)19/h1-5,10-11,14-15,17H,(H,18,19)(H,20,21)/b4-2+
InChI KeySWGKAHCIOQPKFW-DUXPYHPUSA-N
Isomeric SMILES[H]\C(=C(\[H])C1=CC(O)=C(O)C=C1)C(=O)OC(C(O)C(O)=O)C(O)=O
Average Molecular Weight312.229
Monoisotopic Molecular Weight312.048131982
Classification
Description Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acids and derivatives
Alternative Parents
Substituents
  • Cinnamic acid ester
  • Coumaric acid or derivatives
  • Tricarboxylic acid or derivatives
  • Styrene
  • Catechol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Sugar acid
  • Fatty acid ester
  • Phenol
  • Beta-hydroxy acid
  • Fatty acyl
  • Benzenoid
  • Hydroxy acid
  • Alpha-hydroxy acid
  • Monosaccharide
  • Monocyclic benzene moiety
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 50.01%; H 3.87%; O 46.12%DFC
Melting PointMp 146-147°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +37 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCaftaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9840000000-cd512aa4b5b39796cfc9Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dj-0973000000-1a96d8a708695d13762e2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gr-2940000000-a24c1bc2573e378ccd7e2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0540-4900000000-55b90a17ab1875f9bb882016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0409-3982000000-aabe941096f73c4a6cd12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02dr-3940000000-9757ec14c725e63e898e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03mi-3910000000-aec72816b3809d559efe2016-08-03View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBTJ82-E:NSV44-X
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference