Arbutin

Arbutin
Names

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^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:18305^N
ChemSpider	389765^Y
ECHA InfoCard	100.007.138
PubChem CID	346
RTECS number	CE8663000
UNII	C5INA23HXF^Y
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^Y Key: BJRNKVDFDLYUGJ-RMPHRYRLSA-N^Y 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	272.25 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
Safety data sheet	Sigma-Aldrich
NFPA 704	0 0 0
Flash point	293.4 °C (560.1 °F; 566.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N (what is ^YN ?)
Infobox references

Arbutin is a glycoside; a glycosylated hydroquinone extracted from the bearberry plant in the genus Arctostaphylos. It inhibits tyrosinase and thus prevents the formation of melanin. Arbutin is therefore used as a skin-lightening agent. Arbutin is found in wheat, and is concentrated in pear skins. It is also found in Bergenia crassifolia. Arbutin was also produced by an in vitro culture of Schisandra chinensis.

Pure arbutin can be prepared synthetically from the reaction of acetobromoglucose and hydroquinone in the presence of alkali.

Bearberry, which contains arbutin, is a traditional treatment for urinary tract infections.

Bearberry extract is used in skin lightening treatments designed for long term and regular use. An active agent in brands of skin lightening preparations, it is more expensive than traditional skin lightening ingredients like hydroquinone, which is now banned in many countries. In vitro studies of human melanocytes exposed to arbutin at concentrations below 300 μg/mL reported decreased tyrosinase activity and melanin content with little evidence of cytotoxicity.

Arbutin is glucosylated hydroquinone, and may carry similar cancer risks, although there are also claims that arbutin reduces cancer risk. The German Institute of Food Research in Potsdam found that intestinal bacteria can transform arbutin into hydroquinone, which creates an environment favorable for intestinal cancer.

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Wikipedia