Arbutin

Glycoside

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| ImageFile = Arbutin structure. svg
| IUPACName = 4 Hydroxyphenyl β glucopyranoside
| SystematicName = (2R,3S,4S,5R,6S) 2 (Hydroxymethyl) 6 (4 hydroxyphenoxy)oxane 3,4,5 triol
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| ATCCode prefix = D11
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| Legal US = Not FDA approved
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| AdminRoutes = Topically
| Bioavail = 0.53% percutaneous absorption

Arbutin is a compound where a glucose molecule, specifically glucose, is chemically bound to hydroquinone. In aqueous solutions, glucose can exist in one of three stereoisomeric forms: α, β, or γ, with the β anomer being the predominant form. The standard known form of arbutin, β Arbutin, has a molecular formula of C12H16O7 and a molecular weight of 272.25g/mol. Its stereoisomers, α arbutin and γ arbutin, share the same molecular formula and weight but are distinct in their atoms' spatial arrangement. β Arbutin is soluble in water, presenting typically as a white powder that remains stable under standard storage conditions. It exhibits stability in both ethanol and water and demonstrates resistance to light exposure. When dissolved in water, β arbutin may undergo hydrolysis, converting to hydroquinone, which can subsequently oxidize to benzoquinone. Others include the pear (Pyrus spp. ), and certain species of wheat. It is also found in very small quantities in Viburnum opulus, Bergenia crassifolia and Schisandra chinensis. Synthetically, it can also be prepared from the reaction of acetobromoglucose and hydroquinone in the presence of an alkali.

The main application of β arbutin is in the cosmetic industry, where it is incorporated into various skin care products, including creams, serums and lotions, aimed at lightening skin tone and correcting hyperpigmentation. Its efficacy and safety profile make it a sought after ingredient for products targeting solar lentigo, freckles, melasma, and other forms of hyperpigmentation.

For centuries, β arbutin has been used in phytotherapy, or herbal medicine.

Conflicting evidence shows that β arbutin may also work by being decomposed into hydroquinone. If this occurs, the amount of hydroquinone created by decomposition would be small and its contribution to inhibiting the creation of melanin as small.

Arbutin is glucosylated hydroquinone, and may carry similar cancer risks,Unreliable source: date=August 2011 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.