Record Information
Version1.0
Creation date2010-04-08 22:04:53 UTC
Update date2017-10-05 10:25:40 UTC
Primary IDFDB001221
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameArbutin
DescriptionArbutin is a glycoside; a glycosylated hydroquinone extracted from the bearberry plant in the genus Arctostaphylos. It inhibits tyrosinase and thus prevents the formation of melanin. Arbutin is therefore used as a skin-lightening agent. Arbutin is found in wheat, and is concentrated in pear skins (Pyrus communis) (Wikipedia). It has been found as biomarker for the consumption of pears..
CAS Number497-76-7
Structure
Thumb
Synonyms
SynonymSource
β-D-Glucopyranoside, 4-hydroxyphenylbiospider
4-Hydroxyphenyl b-D-glucopyranoside, 9CI, 8CIdb_source
4-hydroxyphenyl beta-D-glucopyranosidebiospider
4-Hydroxyphenyl-beta-D-glucopyranosidebiospider
Arbutinumbiospider
Arbutosidedb_source
Beta-arbutinbiospider
Ericolindb_source
Hydroquinone β-d-glucopyranosidebiospider
Hydroquinone beta-d-glucopyranosidebiospider
Hydroquinone o-beta-d-glucopyranosidebiospider
Hydroquinone-glucosedb_source
Hydroquinone-o-beta-d-glucopyranosidebiospider
P-arbutinbiospider
P-hydroxyphenyl β-d-glucopyranosidebiospider
P-hydroxyphenyl β-d-glucosidebiospider
P-hydroxyphenyl beta-d-glucopyranosidebiospider
P-hydroxyphenyl beta-d-glucosidebiospider
Ursinbiospider
Uvasolbiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H16O7
IUPAC name2-(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
InChI KeyInChIKey=BJRNKVDFDLYUGJ-UHFFFAOYSA-N
Isomeric SMILESOCC1OC(OC2=CC=C(O)C=C2)C(O)C(O)C1O
Average Molecular Weight272
Monoisotopic Molecular Weight272
Classification
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 52.94%; H 5.92%; O 41.14%DFC
Melting PointMp 142-143°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-1.35HANSCH,C ET AL. (1995)
Experimental pKa10
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]18D -60.34 (H2O)DFC
Spectroscopic UV Data[neutral] lmax 294 () (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w29-5950000000-b06dd9542fa7bbd667f2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-014i-2201239000-2f42b1022552b40a482eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03k9-0970000000-7f1103faf15e6a906252View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-f96f8a574fa0e00ad323View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-9800000000-5ea8ff882118ae29ef23View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fr-1790000000-08eaec414aecf42a9f90View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-51e3a547305d55828467View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4900000000-481f6d878e6db1bc8f7cView in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC06186
Pubchem Compound ID440936
Pubchem Substance IDNot Available
ChEBI ID18305
Phenol-Explorer ID659
DrugBank IDNot Available
HMDB IDHMDB29943
CRC / DFC (Dictionary of Food Compounds) IDBWQ88-O:BWQ88-O
EAFUS IDNot Available
Dr. Duke IDARBUTIN
BIGG IDNot Available
KNApSAcK IDC00002638
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDArbutin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allelochemicDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti edemicDUKE
anti melanogenic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti streptococcic33282 A substance that kills or slows the growth of bacteria.DUKE
anti tussive52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
artemicideDUKE
candidicideDUKE
diuretic35498 An agent that promotes the excretion of urine through its effects on kidney function.DUKE
insulin-sparingDUKE
mycoplasmistatDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
urinary antisepticDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.