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Record Information
Version1.0
Created at2020-11-23 19:38:35 UTC
Updated at2021-08-19 23:59:16 UTC
NP-MRD IDNP0002713
Secondary Accession NumbersNone
Natural Product Identification
Common NameArbutin
DescriptionArbutin, also known as ursin or uvasol, 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. Arbutin exists in all living organisms, ranging from bacteria to humans. Arbutin has been detected, but not quantified in, several different foods, such as grapefruits (Citrus X paradisi), orange mints (Mentha aquatica), italian sweet red peppers (Capsicum annuum), half-highbush blueberries (Vaccinium angustifolium X Vaccinium corymbosum), and giant butterburs (Petasites japonicus). This could make arbutin a potential biomarker for the consumption of these foods. Arbutin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 1998 (PMID: 9518563). Based on a literature review a significant number of articles have been published on Arbutin (PMID: 23438684) (PMID: 17984079) (PMID: 12807345) (PMID: 15287073).
Structure
Thumb
Synonyms
ValueSource
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
Chemical FormulaC12H16O7
Average Mass272.2512 Da
Monoisotopic Mass272.08960 Da
IUPAC Name(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
Traditional Nameβ-arbutin
CAS Registry NumberNot Available
SMILES
OC[C@H]1O[C@@H](OC2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
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/t8-,9-,10+,11-,12-/m1/s1
InChI KeyBJRNKVDFDLYUGJ-RMPHRYRLSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 500 MHz, D2O, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Adenosma caeruleumKNApSAcK Database
Angelica furcijuga KITAGAWAKNApSAcK Database
Arctostaphylos uva-ursiKNApSAcK Database
Bergenia crassifoliaKNApSAcK Database
Breynia officinalisKNApSAcK Database
Cotoneaster simonsiiKNApSAcK Database
Onobrychis bobroviKNApSAcK Database
Origanum majoranaKNApSAcK Database
Pyrus communisKNApSAcK Database
Rhododendron ferrugineumKNApSAcK Database
Rhododendron ponticumKNApSAcK Database
Sedum takesimense NakaiKNApSAcK Database
Vaccinium vitis-idaeaKNApSAcK Database
Veronica turrillianaKNApSAcK Database
Species Where Detected
Species NameSourceReference
Escherichia coliKNApSAcK Database
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point199.00 to 200.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point561.00 to 562.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility959100 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-1.350The Good Scents Company Information System
Predicted Properties
PropertyValueSource
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
External Links
HMDB IDHMDB0029943
DrugBank IDDB11217
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030911
KNApSAcK IDC00002638
Chemspider ID389765
KEGG Compound IDC06186
BioCyc IDHYDROQUINONE-O-BETA-D-GLUCOPYRANOSIDE
BiGG IDNot Available
Wikipedia LinkArbutin
METLIN IDNot Available
PubChem Compound440936
PDB IDNot Available
ChEBI ID18305
Good Scents IDrw1653821
References
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  3. Siegers C, Bodinet C, Ali SS, Siegers CP: Bacterial deconjugation of arbutin by Escherichia coli. Phytomedicine. 2003;10 Suppl 4:58-60. doi: 10.1078/1433-187x-00301. [PubMed:12807345 ]
  4. Hori I, Nihei K, Kubo I: Structural criteria for depigmenting mechanism of arbutin. Phytother Res. 2004 Jun;18(6):475-9. doi: 10.1002/ptr.1456. [PubMed:15287073 ]
  5. Oliver AE, Hincha DK, Crowe LM, Crowe JH: Interactions of arbutin with dry and hydrated bilayers. Biochim Biophys Acta. 1998 Mar 6;1370(1):87-97. doi: 10.1016/s0005-2736(97)00246-0. [PubMed:9518563 ]