(αR)-α,2',4,4'-tetrahydroxydihydrochalcone | 131319-67-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (αR)-α,2',4,4'-tetrahydroxydihydrochalcone
• 英文别名: α,2',4,4'-tetrahydroxydihydrochalcone；1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(4-hydroxyphenyl)-1-propanone；4,2',4',alpha-Tetrahydroxydihydrochalcone；(2R)-1-(2,4-dihydroxyphenyl)-2-hydroxy-3-(4-hydroxyphenyl)propan-1-one
• CAS: 131319-67-0
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: SLKHLLNCFGPWAZ-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (αR)-α,2',4,4'-tetrahydroxydihydrochalcone 生成 (αR)-α,2',4,4'-tetra-O-acetyldihydrochalcone
  参考文献：
  名称：

  AUGUSTYN, JAN A. N.;BEZUIDENHOUDT, BAREND C. B.;SWANEPOEL, ANNELIE;FERREI+, TETRAHEDRON, 46,(1990) N2, C. 4429-4442

  摘要：

  DOI：
• 作为产物：
  描述：

  (αR)-α,2',4,4'-tetra-O-acetyldihydrochalcone 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以16 mg的产率得到(αR)-α,2',4,4'-tetrahydroxydihydrochalcone
  参考文献：
  名称：

  黄酮类化合物的对映选择性合成。第2部分。多氧合α-羟基二氢查耳酮和其绝对构型的圆二色性评估

  摘要：

  表现出天然黄酮和异黄酮的氧化模式的手性查尔酮环氧化物被转化为相应的α-羟基二氢查耳酮。两种对映异构体的可用性使得可以通过CD光谱法评估单个手性中心的绝对构型；这种方案适用于定义一些天然存在的类似物的构型，其中两个是新化合物。

  DOI：

  10.1016/s0040-4020(01)86778-8

文献信息

• Anti-osteoporotic and antioxidant activities of chemical constituents of the aerial parts of Ducrosia ismaelis
  作者：Abubaker M.A. Morgan、Hyun Woo Lee、Sang-Hyun Lee、Chi-Hwan Lim、Hae-Dong Jang、Young Ho Kim

  DOI：10.1016/j.bmcl.2014.05.077

  日期：2014.8

  A new pterocarpan glycoside, glycino1-3-O-beta-D-glucopyranoside (1), and a new dihydrochalcone glycoside, ismaeloside A (2), were isolated together with 13 known compounds, including several flavonoids (3-8), lignans (9-11), and phenolic compounds (12-15), from the methanol extract of the aerial parts of Ducrosia ismaelis. The chemical structures of these compounds were elucidated from spectroscopic data and by comparison of these data with previously published results. The anti-osteoporotic and antioxidant activities of the isolated compounds were assessed using tartrate-resistant acid phosphatase (TRAP), oxygen radical absorbance capacity (ORAC), and reducing capacity assays. Compound 15 exhibited a dose-dependent inhibition of osteoclastic TRAP activity with a TRAP value of 86.05 +/- 6.55% of the control at a concentration of 10 mu M. Compounds 1,3-5, and 8 showed potent peroxyl radical-scavenging capacities with ORAC values of 22.79 +/- 0.90, 25.57 +/- 0.49, 20.41 +/- 0.63, 26.55 +/- 0.42, and 24.83 +/- 0.12 mu M Trolox equivalents (TE) at 10 mu M, respectively. Only compound 9 was able to significantly reduce Cu(I) with 23.44 mu M TE at a concentration of 10 mu M. All of the aforementioned compounds were isolated for the first time from a Ducrosia species. (C) 2014 Elsevier Ltd. All rights reserved.
• Enantioselective synthesis of flavonoids. Part 2. Poly-oxygenated α-hydroxydihydrochalcones and circular dichroic assessment of their absolute configuration
  作者：Jan A.N. Augustys、Babend C.B. Bezuidenhoudt、Annelie Swanepoel、Daneel Ferreira

  DOI：10.1016/s0040-4020(01)86778-8

  日期：——

  Chiral chalcone epoxides exhibiting the oxygenation patterns of naturally occurring flavonoids and isoflavonoids were transformed into the corresponding α-hydroxydihydrochalcones. The availability of both enantiomers permitted assessment of the absolute configuration at the single chiral centre by CD spectroscopy; such protocol being applicable to defining the configuration of some naturally occurring

  表现出天然黄酮和异黄酮的氧化模式的手性查尔酮环氧化物被转化为相应的α-羟基二氢查耳酮。两种对映异构体的可用性使得可以通过CD光谱法评估单个手性中心的绝对构型；这种方案适用于定义一些天然存在的类似物的构型，其中两个是新化合物。
• AUGUSTYN, JAN A. N.;BEZUIDENHOUDT, BAREND C. B.;SWANEPOEL, ANNELIE;FERREI+, TETRAHEDRON, 46,(1990) N2, C. 4429-4442
  作者：AUGUSTYN, JAN A. N.、BEZUIDENHOUDT, BAREND C. B.、SWANEPOEL, ANNELIE、FERREI+

  DOI：——

  日期：——