Arbutin

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Arbutin
200px
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
497-76-7 YesY
ChEBI CHEBI:18305 N
ChEMBL ChEMBL232202 N
ChemSpider 389765 YesY
Jmol 3D model Interactive image
PubChem 346
RTECS number CE8663000
UNII C5INA23HXF YesY
  • InChI=1S/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1 YesY
    Key: BJRNKVDFDLYUGJ-RMPHRYRLSA-N YesY
  • InChI=1/C12H16O7/c13-5-8-9(15)10(16)11(17)12(19-8)18-7-3-1-6(14)2-4-7/h1-4,8-17H,5H2/t8-,9-,10+,11-,12-/m1/s1
    Key: BJRNKVDFDLYUGJ-RMPHRYRLBW
  • c1cc(ccc1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
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, CS2
log P -1.35
Vapor pressure almost 0 (25 °C)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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] Arbutin was also produced by an in vitro culture of Schisandra chinensis.[2]

Production

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

Folk medicine

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

Skin lightening agent

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

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]

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ PubChem - Arbutin
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Arbutin, Supporting Nomination for Toxicological Evaluation by the National Toxicology Program
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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