Arbutin

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Arbutin
Arbutin structure.svg
Identifiers
CAS number 497-76-7 YesY
PubChem 346
ChemSpider 389765 YesY
UNII C5INA23HXF YesY
ChEBI CHEBI:18305 N
ChEMBL CHEMBL232202 N
RTECS number CE8663000
Jmol-3D images Image 1
Properties
Molecular formula 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
Solubility in water 5.0 g/100 mL
Solubility soluble in alcohol
slightly soluble in ethyl ether
insoluble in benzene, chloroform, CS2
log P -1.35
Vapor pressure almost 0 (25 °C)
Hazards
MSDS Sigma-Aldrich
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g., sodium chloride Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 293.4 °C (560.1 °F; 566.5 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Arbutin is a glycoside; a glycosylated hydroquinone extracted from the 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.[1]

Production[edit]

Pure arbutin can be prepared synthetically from the reaction of acetobromoglucose and hydroquinone in the presence of alkali.[2]

Folk medicine[edit]

Bearberry, which contains arbutin, is a traditional treatment for urinary tract infections.[3]

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.[4]

Risks[edit]

Arbutin is glucosylated hydroquinone,[5] and may carry similar cancer risks,[6] although there are also claims that arbutin reduces cancer risk.[7] 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.[citation needed]

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. 
  2. ^ PubChem - Arbutin
  3. ^ Garrett, J. T. (2003). The Cherokee Herbal: Native Plant Medicine from the Four Directions. Bear & Company. p. 209. ISBN 1879181967. 
  4. ^ Arbutin, Supporting Nomination for Toxicological Evaluation by the National Toxicology Program
  5. ^ 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" 
  6. ^ Treatment of hyperpigmentation problems / skin lightening[unreliable source?]
  7. ^ Bowman, Lee. July 25, 2005. Scripps Howard News Service. High yuck factor not necessarily good for us anymore