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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:54 UTC
Update Date2020-02-26 21:44:08 UTC
HMDB IDHMDB0029664
Secondary Accession Numbers
  • HMDB29664
Metabolite Identification
Common NameVanilloside
DescriptionVanilloside, also known as avenein or glucovanillin, 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. Vanilloside is an extremely weak basic (essentially neutral) compound (based on its pKa). Vanilloside is a very mild, bitter, and vanilla tasting compound. Outside of the human body, Vanilloside has been detected, but not quantified in, cereals and cereal products and oats. This could make vanilloside a potential biomarker for the consumption of these foods.
Structure
Data?1582753448
Synonyms
ValueSource
4-(beta-D-Glucopyranosyloxy)-3-methoxy-benzaldehydeHMDB
AveneinHMDB
GlucovanillinHMDB
Chemical FormulaC14H18O8
Average Molecular Weight314.2879
Monoisotopic Molecular Weight314.100167552
IUPAC Name3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde
Traditional Nameglucovanillin
CAS Registry Number494-08-6
SMILES
COC1=C(OC2OC(CO)C(O)C(O)C2O)C=CC(C=O)=C1
InChI Identifier
InChI=1S/C14H18O8/c1-20-9-4-7(5-15)2-3-8(9)21-14-13(19)12(18)11(17)10(6-16)22-14/h2-5,10-14,16-19H,6H2,1H3
InChI KeyLPRNQMUKVDHCFX-UHFFFAOYSA-N
Chemical Taxonomy
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
  • Hexose monosaccharide
  • O-glycosyl compound
  • Phenoxy compound
  • Anisole
  • Benzaldehyde
  • Methoxybenzene
  • Benzoyl
  • Phenol ether
  • Alkyl aryl ether
  • Aryl-aldehyde
  • Monocyclic benzene moiety
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Secondary alcohol
  • Ether
  • Organoheterocyclic compound
  • Acetal
  • Oxacycle
  • Polyol
  • Aldehyde
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point188 - 192 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility10.9 g/LALOGPS
logP-0.95ALOGPS
logP-1ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity73.23 m³·mol⁻¹ChemAxon
Polarizability30.06 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kgk-9480000000-c158d3c2c5d79698074fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-000i-1211190000-856afe3b8b9ed78fa842Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0933000000-452354c3868de898b5c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-240644336a6730864119Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2900000000-d838e0093c0048ed3a85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-1938000000-1c0ed402c606cd2029f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-1920000000-a313f0fd42a192b9e740Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-4900000000-11a9d143106555fac0dbSpectrum
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 IDFDB000840
KNApSAcK IDNot Available
Chemspider ID2882053
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3648225
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.. .