Record Information
Version1.0
Creation date2015-05-07 20:29:59 UTC
Update date2019-11-26 03:21:56 UTC
Primary IDFDB030911
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namehydroquinone-O-β-D-glucopyranoside
DescriptionArbutin, also known as hydroquinone-O-beta-D-glucopyranoside or P-hydroxyphenyl beta-D-glucopyranoside, is a member of the class of compounds known as phenolic glycosides. Phenolic glycosides 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. Arbutin is soluble (in water) and a very weakly acidic compound (based on its pKa). Arbutin can be found in a number of food items such as guava, lingonberry, irish moss, and rowal, which makes arbutin a potential biomarker for the consumption of these food products. Arbutin is a glycoside; a glycosylated hydroquinone extracted from the bearberry plant in the genus Arctostaphylos among many other medicinal plants, primarily in the Ericaceae family. Applied topically, it inhibits tyrosinase and thus prevents the formation of melanin. Arbutin is therefore used as a skin-lightening agent. Very tiny amounts of arbutin are found in wheat, pear skins, and some other foods. It is also found in Bergenia crassifolia. Arbutin was also produced by an in vitro culture of Schisandra chinensis .
CAS Number497-76-7
Structure
Thumb
Synonyms
SynonymSource
Hydroquinone-O-beta-D-glucopyranosideChEBI
p-Hydroxyphenyl beta-D-glucopyranosideChEBI
p-Hydroxyphenyl beta-D-glucosideChEBI
UrsinChEBI
UvasolChEBI
Hydroquinone-O-b-D-glucopyranosideGenerator
Hydroquinone-O-β-D-glucopyranosideGenerator
p-Hydroxyphenyl b-D-glucopyranosideGenerator
p-Hydroxyphenyl β-D-glucopyranosideGenerator
p-Hydroxyphenyl b-D-glucosideGenerator
p-Hydroxyphenyl β-D-glucosideGenerator
4-Hydroxyphenyl-b-glucopyranosideHMDB
4-Hydroxyphenyl-β-glucopyranosideHMDB
4-Hydroxyphenyl beta-D-glucopyranosideHMDB
4-Hydroxyphenyl β-D-glucopyranosideHMDB
ArbutineHMDB
ArbutosideHMDB
ArbutyneHMDB
Hydroquinone beta-D-glucopyranosideHMDB
Hydroquinone glucoseHMDB
Hydroquinone β-D-glucopyranosideHMDB
beta-ArbutinHMDB
p-ArbutinHMDB
Β-arbutinHMDB
ArbutinChEBI
Predicted Properties
PropertyValueSource
Water Solubility39.1 g/LALOGPS
logP-1.4ALOGPS
logP-0.9ChemAxon
logS-0.84ALOGPS
pKa (Strongest Acidic)9.82ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area119.61 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.16 m³·mol⁻¹ChemAxon
Polarizability25.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H16O7
IUPAC name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
InChI IdentifierInChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
InChI KeyBJRNKVDFDLYUGJ-RMPHRYRLSA-N
Isomeric SMILES[H][C@]1(CO)O[C@@]([H])(OC2=CC=C(O)C=C2)[C@]([H])(O)[C@@]([H])(O)[C@]1([H])O
Average Molecular Weight272.2512
Monoisotopic Molecular Weight272.089602866
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
  • 4-alkoxyphenol
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MShydroquinone-O-β-D-glucopyranoside, 5 TMS, GC-MS Spectrumsplash10-0uxr-1971000000-e8260464bad4d4a7fa0cSpectrum
GC-MShydroquinone-O-β-D-glucopyranoside, non-derivatized, GC-MS Spectrumsplash10-0uxs-0940000000-9984522469f86670798fSpectrum
Predicted GC-MShydroquinone-O-β-D-glucopyranoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0r00-9750000000-b52a5d3b5fb7e98f0009Spectrum
Predicted GC-MShydroquinone-O-β-D-glucopyranoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MShydroquinone-O-β-D-glucopyranoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0002-0090000000-a7028a3a9618849334b7Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0920000000-532b692f9942a62cc7c8Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0229-0910000000-1cb0580496288b7004fcSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0950000000-4bafd0325d0163331c0aSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0950000000-ffffdfe1cd448f0ea135Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-016r-0290000000-0ebc801fded534434aa5Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-016r-0390000000-5831b5a141106482d24dSpectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-0a4i-0900000000-e517344bdabb66a133e9Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-0a4i-0900000000-315daa57d6f694ca71fbSpectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0a4i-1900000000-df811a65eba1be7fd68dSpectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0a4i-0900000000-4efe3ed1e7614387deb4Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-014i-9000000000-6f8b05f1e0b20e00a25fSpectrum
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-014i-9100000000-7092290163d035871936Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0a4i-0900000000-a0b2ea306ed135900292Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-0a4i-1900000000-26385cb99dd5b38d4f3cSpectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-0a4i-0900000000-0a4c12f1e9730c4685eaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0970000000-e87519bd2c30ca193e5eSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-f812a22889a4e7871758Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-9600000000-9a8f2b8fb568a07413b4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1890000000-cb67c77a9f0c57c986bdSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-52b74ad8f6f3181df26dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-5900000000-45bf1851196d0254c239Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0950000000-597b2277ebb9d13fbb41Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-4940000000-6a46c2768079c1935cb9Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-7900000000-56f28af9a02294ffb2faSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
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