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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 Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).