(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

• ChemBase ID: 72919
• Molecular Formular: C12H16O7
• Molecular Mass: 272.25124
• Monoisotopic Mass: 272.08960285
• SMILES: [C@H]1([C@H]([C@@H]([C@H]([C@@H](O1)Oc1ccc(cc1)O)O)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: 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
• InChIKey: BJRNKVDFDLYUGJ-RMPHRYRLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
• IUPAC Traditional name: arbutin; β-arbutin
• Synonyms: Ursi; Arbutin; Uva; Arbutoside; Hydroquinone β-D-glucopyranoside; 4-Hydroxyphenyl-β-D-glucopyranoside; p-Arbutin; Arbutin

Database IDs

• CAS Number: 497-76-7
• EC Number: 207-850-3
• MDL Number: MFCD00016915
• Beilstein Number: 89673
• PubChem SID: 162037839; 24890841
• PubChem CID: 440936
• CHEBI ID: 18305
• CHEMBL: 232202
• Chemspider ID: 389765
• Unique Ingredient Identifier: C5INA23HXF
• Wikipedia Title: Arbutin

CALCULATED PROPERTIES

• Acid pKa: 9.820456
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -0.90197355
• LogD (pH = 7.4): -0.9035902
• Log P: -0.9019529
• Molar Refractivity: 62.1642 cm^3
• Polarizability: 25.27814 Å^3
• Polar Surface Area: 119.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL, clear (hot)
• Melting Point: 195-198 °C; 199.5°C
• Optical Rotation: [α]/D -64.0±2.0°, c = 3 in H2O; [α]20/D -65±2°, c = 2% in H2O

Safety Information

• Storage Condition: -20°C
• German water hazard class: 3
• Safety Statements: R
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (HPLC); ≥98%; ≥98% (HPLC)
• Grade: analytical standard
• Salt Data: Free Base
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C12H16O7

DETAILS

Selleck Chemicals - S2263

Research Area: Cancer
Biological Activity:
Arbutin(Uva, p-Arbutin) is a tyrosinase inhibitor with an IC50 of 1.09 mM. Arbutin is glucosylated hydroquinone, and may carry similar cancer risks, although there are also claims that arbutin reduces cancer risk. It prevents the formation of melanin. [1][2]

Sigma Aldrich - A4256

Biochem/physiol Actions
Arbutin is a glycosylated hydroquinone used in traditional Chinese medicine (TCM). Arbutin inhibits melanin formation due to its tyrosinase inhibitory activity.
Application
Arbutin, a glycosylated hydroquinone, is used in studies on melanin biosynthesis and as an inhibitor to identify, differentiate and characterize tyrosinase(s).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A4256.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• O’Donoghue JL. J Cosmet Dermatol. 2006 Sep;5(3):196-203.