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Showing Compound Vanilloside (FDB000840)

Record Information
Version1.0
Creation date2010-04-08 22:04:44 UTC
Update date2020-02-24 19:10:15 UTC
Primary IDFDB000840
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVanilloside
DescriptionVanilloside 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 a very mild, bitter, and vanilla tasting compound. Vanilloside has been detected, but not quantified in, a few different foods, such as breakfast cereal, cereals and cereal products, and oats (Avena sativa). This could make vanilloside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Vanilloside.
CAS Number494-08-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
4-(beta-D-Glucopyranosyloxy)-3-methoxy-benzaldehydeHMDB
AveneinHMDB
GlucovanillinHMDB
Benzaldehyde, 4-(beta-D-glucopyranosyloxy)-3-methoxy-biospider
Vanillosidedb_source
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
Chemical FormulaC14H18O8
IUPAC name3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}benzaldehyde
InChI IdentifierInChI=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
Isomeric SMILESCOC1=C(OC2OC(CO)C(O)C(O)C2O)C=CC(C=O)=C1
Average Molecular Weight314.2879
Monoisotopic Molecular Weight314.100167552
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
  • 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:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 53.50%; H 5.77%; O 40.73%DFC
Melting PointMp 188-192°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -88.7 (H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSVanilloside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kgk-9480000000-c158d3c2c5d79698074fSpectrum
Predicted GC-MSVanilloside, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-1211190000-856afe3b8b9ed78fa842Spectrum
Predicted GC-MSVanilloside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uxr-0933000000-452354c3868de898b5c42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-240644336a67308641192015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-2900000000-d838e0093c0048ed3a852015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-1938000000-1c0ed402c606cd2029f02015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-1920000000-a313f0fd42a192b9e7402015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-4900000000-11a9d143106555fac0db2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w2i-0904000000-3f236699a279a1ea87442021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0k9i-3920000000-49daaa8810f4d82a28f72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06ri-3902000000-d38a9afed48f9df0081f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0759000000-e167034d7b96df80df5d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ums-0910000000-ff7902020073bfe3e0f42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-3910000000-ee55c7697274b5fc674c2021-09-23View Spectrum
NMRNot Available
ChemSpider ID2882053
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID3648225
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB29664
CRC / DFC (Dictionary of Food Compounds) IDHCW75-Q:BJR58-X
EAFUS IDNot Available
Dr. Duke IDGLUCOVANILLIN|AVENEIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1407591
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
very mild
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
vanilla
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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 ReferenceNot Available