Record Information
Version1.0
Creation date2010-04-08 22:12:19 UTC
Update date2019-11-26 03:12:56 UTC
Primary IDFDB016244
Secondary Accession NumbersNot Available
Chemical Information
FooDB Nametrans-o-Coumaric acid 2-glucoside
Descriptiontrans-o-Coumaric acid 2-glucoside, also known as melilotoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. trans-o-Coumaric acid 2-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). trans-o-Coumaric acid 2-glucoside has been detected, but not quantified in, herbs and spices and pulses. This could make trans-O-coumaric acid 2-glucoside a potential biomarker for the consumption of these foods.
CAS Number618-67-7
Structure
Thumb
Synonyms
SynonymSource
trans-O-Coumarate 2-glucosideGenerator
MelilotosideHMDB
(2E)-3-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoateGenerator
cis-O-Coumarate 2-glucosideGenerator
(2E)-3-[2-(beta-D-glucopyranosyloxy)phenyl]acrylic acidbiospider
beta-D-Glucosyl-2-coumaratebiospider
trans-beta-D-glucosyl-2-hydroxycinnamatebiospider
trans-beta-D-glucosyl-2-hydroxycinnamic acidbiospider
trans-o-Coumaric acid 2-glucosidemanual
trans-o-Coumaric acid glucosidemanual
Predicted Properties
PropertyValueSource
Water Solubility6.6 g/LALOGPS
logP-0.7ALOGPS
logP-0.44ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)3.7ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area136.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity77.19 m³·mol⁻¹ChemAxon
Polarizability31.19 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC15H18O8
IUPAC name(2E)-3-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)prop-2-enoic acid
InChI IdentifierInChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-2-1-3-8(9)5-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-5+
InChI KeyGVRIYIMNJGULCZ-AATRIKPKSA-N
Isomeric SMILESOCC1OC(OC2=C(\C=C\C(O)=O)C=CC=C2)C(O)C(O)C1O
Average Molecular Weight326.2986
Monoisotopic Molecular Weight326.100167552
Classification
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • Cinnamic acid
  • Cinnamic acid or derivatives
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Styrene
  • Phenol ether
  • Phenoxy compound
  • Benzenoid
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.21%; H 5.56%; O 39.23%DFC
Melting PointMp 240-241°DFC
Boiling PointNot Available
Experimental Water Solubility10 mg/mL at 18 oCBEILSTEIN
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -60.9 (50% EtOH aq.)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0zfr-5943000000-2c7be4677b773c69f301JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00di-1020229000-cd5e122c29a7c414bbb3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0691-0935000000-827cd1afac41e01e6be2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014j-1910000000-074126586479ea59b56aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-2900000000-efb3a4af37c4149f2cb9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01t9-1928000000-1fe18b400bb020298aeeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1911000000-74a7cc1ec970b1c43fcdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03xu-4900000000-1d2c2da5a557045613e5JSpectraViewer
ChemSpider ID10468576
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID6275271
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33581
CRC / DFC (Dictionary of Food Compounds) IDGKS64-L:KPC11-S
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
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference