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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2014/05/04 14:03:23」(JST)
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Arbutin |
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IUPAC name
(2R,3S,4S,5R,6S)-2-Hydroxymethyl-6- (4-hydroxyphenoxy)oxane-3,4,5-triol
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Other names
Arbutoside
Hydroquinone β-D-glucopyranoside
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Identifiers |
CAS number |
497-76-7 Y |
PubChem |
346 |
ChemSpider |
389765 Y |
UNII |
C5INA23HXF Y |
ChEBI |
CHEBI:18305 N |
ChEMBL |
CHEMBL232202 N |
RTECS number |
CE8663000 |
Jmol-3D images |
Image 1 |
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c1cc(ccc1O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
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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 Y
Key: BJRNKVDFDLYUGJ-RMPHRYRLSA-N Y
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
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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 |
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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: Y/N?) |
Infobox references |
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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]
Contents
- 1 Production
- 2 Folk medicine
- 3 Skin lightening agent
- 4 References
Production
Pure arbutin can be prepared synthetically from the reaction of acetobromoglucose and hydroquinone in the presence of alkali.[2]
Folk medicine
Bearberry, which contains arbutin, is a traditional treatment for urinary tract infections.[3]
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.[4]
Risks
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
- ^ 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.
- ^ PubChem - Arbutin
- ^ Garrett, J. T. (2003). The Cherokee Herbal: Native Plant Medicine from the Four Directions. Bear & Company. p. 209. ISBN 1879181967.
- ^ Arbutin, Supporting Nomination for Toxicological Evaluation by the National Toxicology Program
- ^ 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"
- ^ Treatment of hyperpigmentation problems / skin lightening[unreliable source?]
- ^ Bowman, Lee. July 25, 2005. Scripps Howard News Service. High yuck factor not necessarily good for us anymore
English Journal
- Simultaneous determination of arbutin and its decomposed product hydroquinone in whitening creams using high-performance liquid chromatography with photodiode array detection: Effect of temperature and pH on decomposition.
- Jeon JS1,2, Kim BH2, Lee SH2, Kwon HJ2, Bae HJ2, Kim SK1, Park JA1, Shim JH3, Abd El-Aty AM1,4, Shin HC1.
- International journal of cosmetic science.Int J Cosmet Sci.2015 Dec;37(6):567-73. doi: 10.1111/ics.12228. Epub 2015 May 7.
- OBJECTIVE: Arbutin is an effective agent for the treatment of melanin disorders. Arbutin may be converted to hydroquinone under conditions of high temperature, ultraviolet (UV) radiation and dilute acid. The aim of the current study was to develop an analytical method to determine the levels of arbu
- PMID 25857400
- Synergistic inhibition of Haemonchus contortus exsheathment by flavonoid monomers and condensed tannins.
- Klongsiriwet C1, Quijada J2, Williams AR3, Mueller-Harvey I1, Williamson EM4, Hoste H2.
- International journal for parasitology. Drugs and drug resistance.Int J Parasitol Drugs Drug Resist.2015 Jul 3;5(3):127-34. doi: 10.1016/j.ijpddr.2015.06.001. eCollection 2015.
- This study investigated the separate and combined anthelmintic (AH) effects of different phenolic compounds, including condensed tannins and flavonoids, all of which are known to occur in willow leaves, a potentially valuable dry season feed. A range of contrasting model tannins, which span the whol
- PMID 26199861
- Purification and enzymatic characterization of secretory glycoside hydrolase family 3 (GH3) aryl β-glucosidases screened from Aspergillus oryzae genome.
- Kudo K1, Watanabe A1, Ujiie S1, Shintani T1, Gomi K2.
- Journal of bioscience and bioengineering.J Biosci Bioeng.2015 Dec;120(6):614-23. doi: 10.1016/j.jbiosc.2015.03.019. Epub 2015 Apr 27.
- By a global search of the genome database of Aspergillus oryzae, we found 23 genes encoding putative β-glucosidases, among which 10 genes with a signal peptide belonging to glycoside hydrolase family 3 (GH3) were overexpressed in A. oryzae using the improved glaA gene promoter. Consequently, crude
- PMID 25936960
Japanese Journal
- アルブチン含有化粧品とハイドロキノン軟膏によるPigmented Contact Dermatitisの1例 (特集 湿疹・皮膚炎)
- FORMATION OF 2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSIDIC LINKAGES VIA GLYCOSIDATION USING A COMBINATION OF TWO LEWIS ACIDS (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)
- Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 90(1), 198-215, 2015-01-01
- NAID 40020330131
- 臨床皮膚科 = Japanese journal of clinical dermatology 68(7), 484-488, 2014-06
- NAID 40020118783
Related Links
- 「Syntheses of Arbutin-α-glycosides and a Comparison of Their Inhibitory Effects with Those of α-Arbutin and Arbutin on Human Tyrosinase」K. Sugimoto et al., Chem. Pharm. Bull. 51, 798-801(2003) 「The More Effective ...
- ・Lim YJ, Lee EH, Kang TH, Ha SK, Oh MS, Kim SM, Yoon TJ, Kang C, Park JH, Kim SY. (2009) “Inhibitory effects of arbutin on melanin biosynthesis of alpha-melanocyte stimulating hormone-induced hyperpigmentation in 核酸 ...
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