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Merck

03338

α-Arbutin

analytical standard

Synonym(s):

4-Hydroxyphenyl α-D-glucopyranoside, Hydroquinone O-α-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):
C12H16O7
CAS Number:
Molecular Weight:
272.25
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
89675
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grade

analytical standard

Quality Segment

assay

≥99% (HPLC and GC)

shelf life

limited shelf life, expiry date on the label

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

storage temp.

2-8°C

SMILES string

O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC2=CC=C(O)C=C2

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 key

BJRNKVDFDLYUGJ-ZIQFBCGOSA-N

General description

α-Arbutin is a glycosylated hydroquinone and an anomer of naturally occurring arbutin. It is a potent inhibitor of tyrosinase, a vital enzyme involved in epidermal melanin biosynthesis. α-Arbutin finds extensive application as a powerful skin-lightening agent in cosmetic industries.

Application

α-Arbutin may be used as an analytical reference standard for the determination of the analyte in cosmetics by high-performance liquid chromatography with UV detection (HPLC-UV) method.


flash_point_f

Not applicable

flash_point_c

Not applicable

Storage Class

13 - Non Combustible Solids



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Isolation of $\alpha$-arbutin from Xanthomonas CGMCC 1243 fermentation broth by macroporous resin adsorption chromatography
Liu C, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 925, 104-109 (2013)
Syntheses of arbutin-$\alpha$-glycosides and a comparison of their inhibitory effects with those of $\alpha$-arbutin and arbutin on human tyrosinase
Sugimoto K, et al.
Chemical & Pharmaceutical Bulletin, 51(7), 798-801 (2003)
Syntheses of $\alpha$-arbutin-$\alpha$-glycosides and their inhibitory effects on human tyrosinase
Sugimoto K, et al.
Journal of Bioscience and Bioengineering, 99(3), 272-276 (2005)



Global Trade Item Number

SKUGTIN
117552-100G04061838705136
117552-25G04061838705143
03338-100MG04061838618320