Skip to Content
Merck
CN
All Photos(1)

Documents

A4256

Sigma-Aldrich

Arbutin

≥98% (HPLC)

Synonym(s):

4-Hydroxyphenyl-β-D-glucopyranoside, p-Arbutin, Hydroquinone β-D-glucopyranoside

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C12H16O7
CAS Number:
497-76-7
Molecular Weight:
272.25
Beilstein:
89673
EC Number:
207-850-3
MDL number:
MFCD00016915
UNSPSC Code:
12352201
PubChem Substance ID:
24890841
NACRES:
NA.25

biological source

synthetic or plant

Quality Level

200

Assay

≥98% (HPLC)

form

powder

optical activity

[α]25/D -66.0 to -62.0 °, c = 3% (w/v) in water

technique(s)

HPLC: suitable

color

light yellow

mp

195 °C

solubility

water: 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow

storage temp.

room temp

SMILES string

OC[C@H]1O[C@@H](Oc2ccc(O)cc2)[C@H](O)[C@@H](O)[C@@H]1O

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-RMPHRYRLSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

Application

Arbutin, a glycosylated hydroquinone, is used in studies on melanin biosynthesis and as an inhibitor to identify, differentiate and characterize tyrosinase(s).

Biochem/physiol Actions

Arbutin is a glycosylated hydroquinone used in traditional Chinese medicine (TCM). Arbutin inhibits melanin formation due to its tyrosinase inhibitory activity.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Sang Mi An et al.
Phytotherapy research : PTR, 24(8), 1175-1180 (2010-01-16)
Tyrosinase (TYR) catalyzes rate-limiting steps of melanogenesis and thus its inhibitors are potentially useful as hypopigmenting agents. Recently, p-coumaric acid (p-CA) has been suggested to interfere with the pro-melanogenic actions of tyrosine due to its structural similarity with tyrosine (An
Dong-Ho Seo et al.
Applied microbiology and biotechnology, 94(5), 1189-1197 (2012-02-09)
α-Arbutin (α-Ab) is a powerful skin whitening agent that blocks epidermal melanin biosynthesis by inhibiting the enzymatic oxidation of tyrosine and L-3,4-dihydroxyphenylalanine (L-DOPA). α-Ab was effectively synthesized from hydroquinone (HQ) by enzymatic biotransformation using amylosucrase (ASase). The ASase gene from
J J Leyden et al.
Journal of the European Academy of Dermatology and Venereology : JEADV, 25(10), 1140-1145 (2011-06-01)
Facial hyperpigmented disorders are a common complaint in the adult population of all races. First-line topical treatments are usually hydroquinone or topical retinoids, which can cause irritant reactions. The need for better tolerated, yet effective, skin lightening agents that could
Tilak Khanal et al.
Biochemical and biophysical research communications, 413(2), 318-324 (2011-09-06)
A possible role for metabolism by the human intestinal microflora in arbutin-induced cytotoxicity was investigated using human hepatoma HepG2 cells. When the cytotoxic effects of arbutin and hydroquinone (HQ), a deglycosylated metabolite of arbutin, were compared, HQ was more toxic
Chunqiao Liu et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 925, 104-109 (2013-04-02)
α-Arbutin is a glycosylated hydroquinone which has inhibitory function against tyrosinase. In this work, a one-step isolation of α-arbutin from Xanthomonas CGMCC 1243 fermentation broth by macroporous resin adsorption chromatography was investigated. The research results indicated that S-8 resin offered
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service