Arbutin

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ImageFile = Arbutin structure.png ImageSize = 200px
IUPACName = ("2R,3S,4S,5R,6S")-2-Hydroxymethyl-6- (4-hydroxyphenoxy)oxane-3,4,5-triol
OtherNames = Arbutoside
Hydroquinone β-D-glucopyranoside
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CASNo = 497-76-7
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PubChem = 440936
SMILES = C1=CC(=CC=C1O)O [C@H] 2 [C@@H] ( [C@H] ( [C@@H] ( [C@H] (O2)CO)O)O)O
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Formula = C₁₂H₁₆O₇
MolarMass = 272.251 g/mol
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MeltingPtC = 199.5
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Arbutin is both an ether 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.

Risks

Arbutin is glucosylated hydroquinone, [cite journal | quotes = "The potential toxicity of HQ (hydroquinone) is dependent on the route of exposure" | author = O'Donoghue, J L | date = | year = 2006 | month = Sep | title = Hydroquinone and its analogues in dermatology – a risk-benefit viewpoint | journal = Journal of Cosmetic Dermatology | volume = 5 | issue = 3 | pages = 196–203 | doi = 10.1111/j.1473-2165.2006.00253.x
pmid = 17177740 | url = | format = | accessdate = ] and may carry similar cancer risks, [smartskincare.com [http://www.smartskincare.com/conditions/pigmentation/hyperpigmentation-treatments.html Treatment of hyperpigmentation problems / skin lightening] ] although there are also claims that arbutin reduces cancer risk. [Bowman, Lee. July 25, 2005. Scripps Howard News Service. [http://www.knoxstudio.com/shns/story.cfm?pk=BITTERS-07-25-05&cat=AN High yuck factor not necessarily good for us anymore] ] 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.

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