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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:42 UTC
Update Date2019-07-23 06:05:14 UTC
HMDB IDHMDB0029943
Secondary Accession Numbers
  • HMDB29943
Metabolite Identification
Common NameArbutin
DescriptionArbutin, also known as arbutoside or beta-arbutin, 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. Very tiny amounts of arbutin are found in wheat, pear skins, and some other foods. Arbutin is an extremely weak basic (essentially neutral) compound (based on its pKa). Arbutin is a bitter tasting compound. Outside of the human body, Arbutin is found, on average, in the highest concentration within a few different foods, such as bilberries, quinces, and pears. Arbutin has also been detected, but not quantified in, several different foods, such as apples, lingonberries, sweet marjorams, asian pears, and milk (cow). This could make arbutin a potential biomarker for the consumption of these foods. Bearberry, which contains arbutin, is a traditional treatment for urinary tract infections. Bearberry extract is used in skin lightening treatments designed for long term and regular use. Arbutin is a glycoside; a glycosylated hydroquinone extracted from the bearberry plant in the genus Arctostaphylos among many other medicinal plants, primarily in the family Ericaceae. It is also found in Bergenia crassifolia. Arbutin is glucosylated hydroquinone, and may carry similar cancer risks, although there are also claims that arbutin reduces cancer risk. Arbutin was also produced by an in vitro culture of Schisandra chinensis. In vitro studies of human melanocytes exposed to arbutin at concentrations below 300 μg/mL reported decreased tyrosinase activity and melanin content with little evidence of cytotoxicity.
Structure
Data?1563861914
Synonyms
ValueSource
4-Hydroxyphenyl b-D-glucopyranoside, 9ci, 8ciHMDB
4-Hydroxyphenyl beta-D-glucopyranosideHMDB
4-Hydroxyphenyl-beta-D-glucopyranosideHMDB
ArbutinumHMDB
ArbutosideHMDB
beta -D-Glucopyranoside, 4-hydroxyphenylHMDB
beta-ArbutinHMDB
EricolinHMDB
Hydroquinone beta -D-glucopyranosideHMDB
Hydroquinone beta-D-glucopyranosideHMDB
Hydroquinone O-beta-D-glucopyranosideHMDB
Hydroquinone-glucoseHMDB
Hydroquinone-O-beta-D-glucopyranosideHMDB
p-ArbutinHMDB
p-Hydroxyphenyl beta -D-glucopyranosideHMDB
p-Hydroxyphenyl beta -D-glucosideHMDB
p-Hydroxyphenyl beta-D-glucopyranosideHMDB
p-Hydroxyphenyl beta-D-glucosideHMDB
UrsinHMDB
UvasolHMDB
Chemical FormulaC12H16O7
Average Molecular Weight272.2512
Monoisotopic Molecular Weight272.089602866
IUPAC Name2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
Traditional Namearbutin
CAS Registry Number497-76-7
SMILES
OCC1OC(OC2=CC=C(O)C=C2)C(O)C(O)C1O
InChI Identifier
InChI=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
InChI KeyBJRNKVDFDLYUGJ-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
  • 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
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142 - 143 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.35Not Available
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
Polarizability25.92 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, Positivesplash10-0w29-5950000000-b06dd9542fa7bbd667f2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-014i-2201239000-2f42b1022552b40a482eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0970000000-7f1103faf15e6a906252Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-f96f8a574fa0e00ad323Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9800000000-5ea8ff882118ae29ef23Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1790000000-08eaec414aecf42a9f90Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-51e3a547305d55828467Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4900000000-481f6d878e6db1bc8f7cSpectrum
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 ID659
FoodDB IDFDB001221
KNApSAcK IDC00002638
Chemspider ID339
KEGG Compound IDC06186
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkArbutin
METLIN IDNot Available
PubChem Compound346
PDB IDNot Available
ChEBI ID18305
Food Biomarker OntologyNot Available
VMH IDARBT
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Siegers C, Bodinet C, Ali SS, Siegers CP: Bacterial deconjugation of arbutin by Escherichia coli. Phytomedicine. 2003;10 Suppl 4:58-60. [PubMed:12807345 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .