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A4256

Sigma-Aldrich

Arbutin

≥98% (HPLC)

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C12H16O7
Numéro CAS:
497-76-7
Poids moléculaire :
272.25
Numéro Beilstein :
89673
Numéro CE :
207-850-3
Numéro MDL:
MFCD00016915
Code UNSPSC :
12352201
ID de substance PubChem :
24890841
Nomenclature NACRES :
NA.25

Source biologique

synthetic or plant

Niveau de qualité

200

Pureté

≥98% (HPLC)

Forme

powder

Activité optique

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

Technique(s)

HPLC: suitable

Couleur

light yellow

Pf

195 °C

Solubilité

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

Température de stockage

room temp

Chaîne SMILES 

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

Clé InChI

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).

Actions biochimiques/physiologiques

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

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (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
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
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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