Arbutin, inhibitor of tyrosinase

Key facts

CAS number

497-76-7

Purity

>98%

Form

Solid

form

Source

Arctostaphylos sp.

Molecular weight

272.25 Da

Molecular formula

C₁₂H₁₆O₇

PubChem

440936

Nature

Native

Solubility

Soluble in water and in ethanol

Biochemical name

Arbutin

Biological description

Naturally occurring beta-D-glucopyranoside of hydroquinone. Isolated from the leaves of Bearberry (Arctostaphylos). Competitive inhibitor of tyrosinase in melanocytes. Inhibits melanin biosynthesis.

Canonical smiles

C1=CC(=CC=C1O)OC2C(C(C(C(O2)CO)O)O)O

Isomeric smiles

C1=CC(=CC=C1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)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

IUPAC Name

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