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A4256

Sigma-Aldrich

Arbutin

≥98% (HPLC)

Synonym(s):

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

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About This Item

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

biological source

synthetic or plant

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

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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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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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
Shinji Sakuma et al.
Molecular pharmaceutics, 9(4), 922-929 (2012-02-23)
A carboxyl group-terminated polyamidoamine dendrimer (generation: 3.0) bearing arbutin, which is a substrate of Na⁺/glucose cotransporter 1 (SGLT1), via a nonbiodegradable ω-amino triethylene glycol linker (PAMAM-ARB), inhibits SGLT1-mediated D-glucose uptake, as does phloridzin, which is a typical SGLT1 inhibitor. Here
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
Hyo-Jong Lee et al.
Inflammation research : official journal of the European Histamine Research Society ... [et al.], 61(8), 817-825 (2012-04-11)
Arbutin, which is found in the genus Arctostaphylos, is an anti-oxidant and a depigmenting agent. The present study was designed to validate the anti-inflammatory effect of arbutin. The anti-inflammatory properties of arbutin were studied using a lipopolysaccharide (LPS)-stimulated murine BV2
Hsiou-Yu Ding et al.
Experimental dermatology, 20(9), 720-724 (2011-05-28)
Two natural acetophenone derivatives, 2,5-dihydroxyacetophenone (2,5-DHAP) and 2,6-DHAP, were purified from Cynanchum bungei and identified as murine tyrosinase inhibitors. Investigation into 2,5-DHAP showed it to be an uncompetitive inhibitor of murine tyrosinase (K(I) 0.28 mm). 2,5-DHAP strongly inhibited both melanogenesis and
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