| Arbutin | |
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(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6- (4-hydroxyphenoxy)oxane-3,4,5-triol |
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Other names
Arbutoside |
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| Identifiers | |
| CAS number | 497-76-7 |
| PubChem | 440936 |
| ChemSpider | 389765 |
| UNII | C5INA23HXF |
| ChEBI | CHEBI:18305 |
| ChEMBL | CHEMBL232202 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C12H16O7 |
| Molar mass | 272.25 g mol−1 |
| Melting point |
199.5 °C, 473 K, 391 °F |
| (verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Arbutin is both an ether and a glycoside; a glycosylated hydroquinone extracted from 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.[1]
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.[2]
Arbutin is glucosylated hydroquinone,[3] and may carry similar cancer risks,[4] although there are also claims that arbutin reduces cancer risk.[5] 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. It is known that the body excretes 64-75% of arbutin in urine, and arbutin converted to hydroquinone has an antibacterial effect in the urinary tract, hence the use of bearberry in herbal medicine, but it is not known why this substance plays a role in cancer development. It also has an anti-glycation activity.