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Showing Compound 2-O-Acetyl-trans-coutaric acid (FDB013140)

Record Information
Version1.0
Creation date2010-04-08 22:10:33 UTC
Update date2019-11-26 03:08:02 UTC
Primary IDFDB013140
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name2-O-Acetyl-trans-coutaric acid
Description2-O-Acetyl-trans-coutaric acid belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. 2-O-Acetyl-trans-coutaric acid has been detected, but not quantified in, green vegetables. This could make 2-O-acetyl-trans-coutaric acid a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 2-O-Acetyl-trans-coutaric acid.
CAS Number106928-35-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
2-O-Acetyl-trans-coutarateGenerator
2-O-Acetyl-3-trans-O-P-coumaroyltartaric acidHMDB
2-(Acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioateGenerator
2-O-Acetyl-3-trans-O-p-coumaroyltartaric aciddb_source
2-O-Acetyl-trans-coutaric aciddb_source
Predicted Properties
PropertyValueSource
Water Solubility0.27 g/LALOGPS
logP1.94ALOGPS
logP1.34ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.15ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area147.43 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity76.91 m³·mol⁻¹ChemAxon
Polarizability31.07 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H14O9
IUPAC name2-(acetyloxy)-3-{[(2E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid
InChI IdentifierInChI=1S/C15H14O9/c1-8(16)23-12(14(19)20)13(15(21)22)24-11(18)7-4-9-2-5-10(17)6-3-9/h2-7,12-13,17H,1H3,(H,19,20)(H,21,22)/b7-4+
InChI KeyAILCSCQIQZTQJR-QPJJXVBHSA-N
Isomeric SMILESCC(=O)OC(C(OC(=O)\C=C\C1=CC=C(O)C=C1)C(O)=O)C(O)=O
Average Molecular Weight338.2663
Monoisotopic Molecular Weight338.063782046
Classification
Description Belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentCoumaric acid esters
Alternative Parents
Substituents
  • Coumaric acid ester
  • Tetracarboxylic acid or derivatives
  • Coumaric acid or derivatives
  • Cinnamic acid ester
  • Styrene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Phenol
  • Sugar acid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.26%; H 4.17%; O 42.57%DFC
Melting PointMp 194-198° dec.DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data312 () (MeOH)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS2-O-Acetyl-trans-coutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0005-4910000000-b49ffe2cf366fa81ae95Spectrum
Predicted GC-MS2-O-Acetyl-trans-coutaric acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01bl-9360330000-de8dc951995157a09450Spectrum
Predicted GC-MS2-O-Acetyl-trans-coutaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06rg-4972000000-13326cd7eaa2968bb9bf2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-4930000000-6c1d2cf284fa9bd05f7b2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052b-8910000000-c25646efb0d6dc657b122016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003s-3790000000-e59591232d06d6c216ff2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2920000000-0a2195ebb7e2331916bd2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-9600000000-5ee80c0bad7797b9d9522021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-009b-1946000000-a96cb96a8f5c391c5d582016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-0921000000-61429a01d06f041f657e2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-2900000000-8a4e68251c193b7a6bd32016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0095-0986000000-000f9bd40fa96e6112ab2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kb-2930000000-98d12d5e4d9f389fb7302021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2910000000-7dc8d63e0290016d67032021-09-24View Spectrum
NMRNot Available
ChemSpider ID8557914
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10382471
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34621
CRC / DFC (Dictionary of Food Compounds) IDBTJ82-E:HOX89-I
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