(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol

• ChemBase编号: 72919
• 分子式: C12H16O7
• 平均质量: 272.25124
• 单一同位素质量: 272.08960285
• SMILES: [C@H]1([C@H]([C@@H]([C@H]([C@@H](O1)Oc1ccc(cc1)O)O)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@@H](Oc2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
• InChI: 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
• InChIKey: BJRNKVDFDLYUGJ-RMPHRYRLSA-N

名称和登记号

名称

• IUPAC标准名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4,5-triol
• IUPAC传统名: arbutin; β-arbutin
• 别名: Ursi; Arbutin; Uva; Arbutoside; Hydroquinone β-D-glucopyranoside; 4-Hydroxyphenyl-β-D-glucopyranoside; p-Arbutin; Arbutin

登记号

• CAS号: 497-76-7
• EC号: 207-850-3
• MDL号: MFCD00016915
• Beilstein号: 89673
• PubChem SID: 24890841; 162037839
• PubChem CID: 440936
• CHEBI ID: 18305
• CHEMBL: 232202
• Chemspider ID: 389765
• 美国药典/FDA物质标识码: C5INA23HXF
• 维基百科标题: Arbutin

理论计算性质

• Acid pKa: 9.820456
• 质子受体: 7
• 质子供体: 5
• LogD (pH = 5.5): -0.90197355
• LogD (pH = 7.4): -0.9035902
• Log P: -0.9019529
• 摩尔折射率: 62.1642 cm^3
• 极化性: 25.27814 Å^3
• 极化表面积: 119.61 Å^2
• 可自由旋转的化学键: 3
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: H2O: soluble50 mg/mL, clear (hot)
• 熔点: 195-198 °C; 199.5°C
• 比旋光度: [α]/D -64.0±2.0°, c = 3 in H2O; [α]20/D -65±2°, c = 2% in H2O

安全信息

• 保存条件: -20°C
• 德国WGK号: 3
• 安全公开号: R
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

产品相关信息

• 纯度: ≥96.0% (HPLC); ≥98%; ≥98% (HPLC)
• 级别: analytical standard
• 成盐信息: Free Base
• 有效期: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C12H16O7

详细说明

Selleck Chemicals - S2263

Research Area: Cancer
Biological Activity:
Arbutin(Uva, p-Arbutin) is a tyrosinase inhibitor with an IC50 of 1.09 mM. Arbutin is glucosylated hydroquinone, and may carry similar cancer risks, although there are also claims that arbutin reduces cancer risk. It prevents the formation of melanin. [1][2]

Sigma Aldrich - A4256

Biochem/physiol Actions
Arbutin is a glycosylated hydroquinone used in traditional Chinese medicine (TCM). Arbutin inhibits melanin formation due to its tyrosinase inhibitory activity.
Application
Arbutin, a glycosylated hydroquinone, is used in studies on melanin biosynthesis and as an inhibitor to identify, differentiate and characterize tyrosinase(s).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A4256.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

参考文献

• O’Donoghue JL. J Cosmet Dermatol. 2006 Sep;5(3):196-203.