Arbutin

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Arbutin
Arbutin structure.svg
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.138
RTECS number CE8663000
UNII
Properties
C12H16O7
Molar mass 272.25 g·mol−1
Appearance colorless to white powder
Melting point 199.5 °C (391.1 °F; 472.6 K)
Boiling point 561.6
5.0 g/100 mL
Solubility soluble in alcohol
slightly soluble in ethyl ether
insoluble in benzene, chloroform, carbon disulfide
log P -1.35
Vapor pressure almost 0 (25 °C)
-158.0·10−6 cm3/mol
Hazards
Safety data sheet Sigma-Aldrich
NFPA 704
Flammability code 0: Will not burn. E.g., waterHealth code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chlorideReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
0
0
Flash point 293.4 °C (560.1 °F; 566.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Arbutin is a glycoside; a glycosylated hydroquinone extracted from the bearberry plant in the genus Arctostaphylos among many other medicinal plants, primarily in the Ericaceae family. Applied topically, it inhibits tyrosinase and thus prevents the formation of melanin. Arbutin is therefore used as a skin-lightening agent. Very tiny amounts of arbutin are found in wheat, pear skins, and some other foods. It is also found in Bergenia crassifolia.[1] Arbutin was also produced by an in vitro culture of Schisandra chinensis.[2]

It can be prepared synthetically from the reaction of acetobromoglucose and hydroquinone in the presence of alkali.[3]

Folk medicine[edit]

Bearberry, which contains arbutin, is a traditional treatment for urinary tract infections.[4]

Skin lightening agent[edit]

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.[5]

Risks[edit]

Arbutin is glucosylated hydroquinone,[6] and may carry similar cancer risks,[7] although there are also claims that arbutin reduces cancer risk.[8] 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.[9]

See also[edit]

References[edit]

  1. ^ Carmen Pop; Laurian Vlase; Mircea Tamas (2009). "Natural Resources Containing Arbutin. Determination of Arbutin in the Leaves of Bergenia crassifolia (L.) Fritsch. acclimated in Romania". Not. Bot. Hort. Agrobot. Cluj. 37 (1): 129–132. Archived from the original on 2011-08-23.
  2. ^ Dusková J, Dusek J, Jahodár L, Poustka F (2005). "[Arbutin, salicin: the possibilities of their biotechnological production]". Ceska Slov Farm. 54 (2): 78–81. PMID 15895970.
  3. ^ PubChem - Arbutin
  4. ^ Garrett, J. T. (2003). The Cherokee Herbal: Native Plant Medicine from the Four Directions. Bear & Company. p. 209. ISBN 1879181967.
  5. ^ Arbutin Archived May 27, 2010, at the Wayback Machine., Supporting Nomination for Toxicological Evaluation by the National Toxicology Program
  6. ^ O'Donoghue, J L (September 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
  7. ^ Treatment of hyperpigmentation problems / skin lightening[unreliable source?]
  8. ^ Bowman, Lee. July 25, 2005. Scripps Howard News Service. High yuck factor not necessarily good for us anymore Archived September 28, 2007, at the Wayback Machine.
  9. ^ Blaut M, Braune A, Wunderlich S, Sauer P, Schneider H, Glatt H (2006). "Mutagenicity of arbutin in mammalian cells after activation by human intestinal bacteria". Food Chem. Toxicol. 44 (11): 1940–7. doi:10.1016/j.fct.2006.06.015. PMID 16904805.