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A4256

Sigma-Aldrich

Arbutin

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C12H16O7
Número de CAS:
497-76-7
Peso molecular:
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

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

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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)

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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
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
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
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
Dong-Ho Seo et al.
Applied microbiology and biotechnology, 95(6), 1417-1425 (2012-07-31)
Arbutins (α- and β-arbutins) are glycosylated hydroquinones that are commercially used in the cosmetic industry. These compounds have an inhibitory function against tyrosinase, a critical enzyme for generating pigments, which leads to the prevention of melanin formation, resulting in a
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