Arbutin
From Wikipedia, the free encyclopedia
| Arbutin | |
|---|---|
 |
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| 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] |
| PubChem | |
| SMILES | C1=CC(=CC=C1O)O[C@H]2[C@@H] ([C@H]([C@@H]([C@H](O2)CO)O)O)O |
| Properties | |
| Molecular formula | C12H16O7 |
| Molar mass | 272.251 g/mol |
| Melting point |
199.5 °C, 473 K, 391 °F |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Arbutin is both an ester and a glycoside; a glycosylated benzoquinone 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 also found in wheat, and is concentrated in pear skins.
[edit] Risks
Arbutin is glucosylated hydroquinone,[1] and may carry similar cancer risks,[2] although there are also claims that arbutin reduces cancer risk.[3] The German Institute of Food Research in Potsdam found that intestinal bacteria can transform arbutin into hydroquinone, which creates an environment favourable 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.
[edit] References
- ^ O'Donoghue, J L (Sep 2006). "Hydroquinone and its analogues in dermatology – a risk-benefit viewpoint". Journal of Cosmetic Dermatology 5 (3): 196–203. doi:. PMID 17177740.
- ^ smartskincare.com Treatment of hyperpigmentation problems / skin lightening
- ^ Bowman, Lee. July 25, 2005. Scripps Howard News Service. High yuck factor not necessarily good for us anymore
