| 词条 | Arbutin |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 396293096 | ImageFile = Arbutin structure.svg | IUPACName = (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6- (4-hydroxyphenoxy)oxane-3,4,5-triol | OtherNames = Arbutoside Hydroquinone β-D-glucopyranoside |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 389765 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 232202 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = C5INA23HXF | InChIKey = BJRNKVDFDLYUGJ-RMPHRYRLBW | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = BJRNKVDFDLYUGJ-RMPHRYRLSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 497-76-7 | EINECS = | PubChem = 346 | SMILES = c1cc(ccc1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O | 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 | RTECS = CE8663000 | MeSHName = | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 18305 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = }} |Section2={{Chembox Properties | C=12 | H=16 | O=7 | Appearance = colorless to white powder | Density = | MeltingPtC = 199.5 | MeltingPt_notes = | BoilingPt = 561.6 | BoilingPt_notes = | Solubility = 5.0 g/100 mL | SolubleOther = soluble in alcohol slightly soluble in ethyl ether insoluble in benzene, chloroform, carbon disulfide | pKa = | pKb = | LogP = -1.35 | VaporPressure = almost 0 (25 °C) | MagSus = -158.0·10−6 cm3/mol }} |Section7={{Chembox Hazards | ExternalSDS = Sigma-Aldrich | EUClass = | MainHazards = | NFPA-H = 0 | NFPA-F = 0 | NFPA-R = 0 | NFPA-S = | RPhrases = | SPhrases = | RSPhrases = | FlashPtC = 293.4 | AutoignitionPtC = | ExploLimits = | PEL = }} }}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 medicineBearberry, which contains arbutin, is a traditional treatment for urinary tract infections.[4]Skin lightening agentBearberry 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] RisksArbutin 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
References1. ^{{cite journal|url=http://notulaebotanicae.ro/nbha/article/viewFile/3108/2947 |title=Natural Resources Containing Arbutin. Determination of Arbutin in the Leaves of Bergenia crassifolia (L.) Fritsch. acclimated in Romania |author1=Carmen Pop |author2=Laurian Vlase |author3=Mircea Tamas |journal=Not. Bot. Hort. Agrobot. Cluj |volume=37 |issue=1 |year=2009 |pages=129–132 |deadurl=yes |archiveurl=https://web.archive.org/web/20110823104032/http://notulaebotanicae.ro/nbha/article/viewFile/3108/2947 |archivedate=2011-08-23 |df= }} 2. ^{{cite journal | pmid = 15895970 | title = [Arbutin, salicin: the possibilities of their biotechnological production] |vauthors=Dusková J, Dusek J, Jahodár L, Poustka F | journal = Ceska Slov Farm. | volume = 54 | issue = 2 | year = 2005 | pages = 78–81}} 3. ^[https://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?q=all&cid=346#ec PubChem - Arbutin] 4. ^{{cite book|last=Garrett|first=J. T.|title=The Cherokee Herbal: Native Plant Medicine from the Four Directions|year=2003|publisher=Bear & Company|isbn=1879181967|pages=209|url=https://books.google.com/books?id=OE_dlKnYkd4C&pg=PA209&lpg=PA209&dq=bearberry+uti+cherokee&source=bl&ots=SKRzVjZDLK&sig=AJjZBXHQFPEX2R_5edbCDAZESUI&hl=en&sa=X&ei=_dSuT8yIA4ah0QXOv5GHCQ&ved=0CGYQ6AEwAw#v=onepage&q=bearberry&f=false}} 5. ^[https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/arbutin_508.pdf Arbutin] {{webarchive |url=https://web.archive.org/web/20100527233957/http://ntp.niehs.nih.gov/files/Arbutin.pdf |date=May 27, 2010 }}, Supporting Nomination for Toxicological Evaluation by the National Toxicology Program 6. ^{{cite journal | author = O'Donoghue, J L |date= September 2006 | 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 = | quote = "The potential toxicity of HQ (hydroquinone) is dependent on the route of exposure" }} 7. ^Treatment of hyperpigmentation problems / skin lightening {{Unreliable source?|date=August 2011}} 8. ^Bowman, Lee. July 25, 2005. Scripps Howard News Service. High yuck factor not necessarily good for us anymore {{webarchive |url=https://web.archive.org/web/20070928010949/http://www.knoxstudio.com/shns/story.cfm?pk=BITTERS-07-25-05&cat=AN |date=September 28, 2007 }} 9. ^{{cite journal |vauthors=Blaut M, Braune A, Wunderlich S, Sauer P, Schneider H, Glatt H |title=Mutagenicity of arbutin in mammalian cells after activation by human intestinal bacteria |journal=Food Chem. Toxicol. |volume=44 |issue=11 |pages=1940–7 |year=2006 |pmid=16904805 |doi=10.1016/j.fct.2006.06.015 |url=}} 1 : Phenol glucosides |
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