Arbutin

Arbutin
Names
	IUPAC name 4-Hydroxyphenyl β-D-glucopyranoside
	Preferred IUPAC name (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
	Other names Arbutoside; Hydroquinone β-D-glucopyranoside
Identifiers
CAS Number	497-76-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	89673
ChEBI	CHEBI:18305 ;
ChEMBL	ChEMBL232202 ;
ChemSpider	389765 ;
ECHA InfoCard	100.007.138
EC Number	207-850-3;
KEGG	C06186 ;
PubChem CID	346;
RTECS number	CE8663000;
UNII	C5INA23HXF ;
CompTox Dashboard (EPA)	DTXSID7040152 ;
	InChI 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 Key: BJRNKVDFDLYUGJ-RMPHRYRLSA-N ; InChI=1/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 Key: BJRNKVDFDLYUGJ-RMPHRYRLBW;
	SMILES c1cc(ccc1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O;
Properties
Chemical formula	C12H16O7
Molar mass	272.253 g·mol−1
Appearance	colorless to white powder
Melting point	199.5 °C (391.1 °F; 472.6 K)
Boiling point	561.6
Solubility in water	5.0 g/100 mL
Solubility	soluble in alcohol ; slightly soluble in ethyl ether ; insoluble in benzene, chloroform, carbon disulfide
log P	-1.35
Vapor pressure	almost 0 (25 °C)
Magnetic susceptibility (χ)	-158.0·10−6 cm3/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
NFPA 704 (fire diamond)	0 0 0
Flash point	293.4 °C (560.1 °F; 566.5 K)
Safety data sheet (SDS)	Sigma-Aldrich
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Arbutin is a glycoside; a glycosylated hydroquinone extracted from the bearberry plant in the genus Arctostaphylos among many other medicinal plants, primarily in the family Ericaceae. Applied topically, it inhibits tyrosinase and thus prevents the formation of melanin. Arbutin is therefore used as a skin-lightening agent. Very tiny amounts of arbutin are found in wheat, pear skins, and some other foods. It is also found in Viburnum opulus and Bergenia crassifolia. Arbutin was also produced by an in vitro culture of Schisandra chinensis.