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| 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 | |
| 3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.007.138 
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| PubChem CID | |
| UNII | |
| CompTox Dashboard (EPA) | |
InChI
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SMILES
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| Properties | |
| Chemical formula | C12H16O7 |
| Molar mass | 272.25 g/mol |
| Melting point | 199.5 °C (391.1 °F; 472.6 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
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Arbutin also known as Uva Ursi and Bearberry Extract 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.
Skin Lightening Agent
Bearberry Extract is used in skin lightening treatments designed for for long term and regular use. An active agent in brands of skin lightening preparations like Super Skin Lightener, 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.
Risks
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 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. it also has an antiglycation activity
References
- Natural Resources Containing Arbutin. Determination of Arbutin in the Leaves of Bergenia crassifolia (L.) Fritsch. acclimated in Romania. Carmen Pop, Laurian Vlase, Mircea Tamas, Not. Bot. Hort. Agrobot. Cluj 37 (1) 2009, 129-132
- Arbutin - Supporting Nomination for Toxicological Evaluation by the National Toxicology Program
- O'Donoghue, J L (2006). "Hydroquinone and its analogues in dermatology – a risk-benefit viewpoint". Journal of Cosmetic Dermatology. 5 (3): 196–203. doi:10.1111/j.1473-2165.2006.00253.x. PMID 17177740.
The potential toxicity of HQ (hydroquinone) is dependent on the route of exposure
{{cite journal}}: Unknown parameter|month=ignored (help) - 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
Arom Jedsadayanmata, In Vitro Antiglycation Activity of Arbutin, Naresuan University Journal 2005; 13(2): 35-41