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A4256

Sigma-Aldrich

Arbutin

≥98% (HPLC)

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C12H16O7
Číslo CAS:
497-76-7
Molekulová hmotnost:
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)

Osvědčení o analýze (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
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
Mi Jeong Kang et al.
Archives of pharmacal research, 34(4), 687-693 (2011-05-06)
A possible role of metabolism by intestinal bacteria in arbutin-induced toxicity was investigated in mammalian cell cultures. Following an incubation of arbutin with intestinal bacteria, either Bifidobacterium longum HY81 or Bifidobacterium adolescentis, for 24 h, its aglycone hydroquinone could be
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
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