2,3,4'-trihydroxy-4-methoxydeoxybenzoin | 1173918-22-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2,3,4'-trihydroxy-4-methoxydeoxybenzoin
• 英文别名: 2,3,4''-Trihydroxy-4-methoxydeoxybenzoin；1-(2,3-dihydroxy-4-methoxyphenyl)-2-(4-hydroxyphenyl)ethanone
• CAS: 1173918-22-3
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: KQWFSABOMCCDLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,4'-trihydroxy-4-methoxydeoxybenzoin 、 N,N-二甲基甲酰胺 在 三氟化硼乙醚 、 甲基磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以73%的产率得到8,4’-dihydroxy-7-methoxyisoflavone
  参考文献：
  名称：

  合成异黄酮的自由基清除、抗酪氨酸酶和细胞黑色素生成抑制活性

  摘要：

  在这项研究中，我们研究了合成异黄酮在药妆品中的应用潜力。合成了 25 种异黄酮，并评估了它们清除自由基和抑制蘑菇酪氨酸酶的能力，以及它们对 B16F10 鼠黑色素瘤细胞和 HaCaT 人角质形成细胞的细胞活力的影响。进一步研究了显示出显着蘑菇酪氨酸酶抑制活性的异黄酮在体外 B16F10 黑素细胞中减少细胞黑色素形成和抗酪氨酸酶活性。在测试的异黄酮中，6-羟基黄豆苷元 (2) 是 ABTS.+ 和 DPPH 的最强清除剂。SC50 值分别为 11.3±0.3 和 9.4±0.1 μM 的自由基。Texasin (20) 表现出最有效的蘑菇酪氨酸酶抑制作用 (IC50 14.9±4.5 μM)，而 retusin (17) 分别显示出对 B16F10 黑素细胞中细胞黑色素形成和抗酪氨酸酶活性的最有效抑制。总之，retusin (17) 和 texasin (20) 都表现出强大的自由基清除能力

  DOI：

  10.1002/cbdv.201400208
• 作为产物：
  描述：

  对羟基苯乙酸 、 3-甲氧基儿茶酚 在 三氟化硼乙醚 作用下， 反应 2.0h， 以78.5%的产率得到2,3,4'-trihydroxy-4-methoxydeoxybenzoin
  参考文献：
  名称：

  Potential antioxidants and tyrosinase inhibitors from synthetic polyphenolic deoxybenzoins

  摘要：

  Deoxybenzoins (DOBs) are one-pot synthetic precursors of isoflavones with feature analogous to those beneficial polyphenols such as resveratrol (stilbene) and phloretin (dihydrochalcone). In this study, seventeen polyphenolic DOBs were synthesized and evaluated by various antioxidant assays and tyrosinase inhibitory effect in vitro. Results displayed that these DOBs are powerful antioxidants; for example, 2,3,4-trihydroxy-3',4'-dimethoxydeoxybenzoin possesses an excellent anti-lipid peroxidation activity (IC50 = 0.72 +/- 0.16 mu M), whilst 2,4,4',5-tetrahydroxydeoxybenzoin showed good DPPH radical scavenging activity (IC50 = 0.69 +/- 0.04 mu M), which were better than Trolox and vitamin C. Besides exhibiting a weak metal chelating effect, these DOBs were effective in scavenging ABTS(center dot+) and superoxide anion (O-2(center dot-)) radicals. DOBs also exhibited potent mushroom tyrosinase inhibitory activity; for example 2,3,4'-trihydroxy4- methoxydeoxybenzoin displayed stable and significant inhibitory effect on tyrosinase activity, with IC50 values 43.37, 43.10 and 46.10 mu M at incubation intervals of 0.5, 1.5, and 2.5 h, respectively. These results suggest that, with the advantage of being readily synthesizable small molecules, DOBs can be potentially developed into clinical and industrial antioxidants. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.05.019

文献信息

• Synthesis and Structure−Activity Relationship Study of Deoxybenzoins on Relaxing Effects of Porcine Coronary Artery
  作者：Tzy-Ming Lu、Daih-Huang Kuo、Horng-Huey Ko、Lean-Teik Ng

  DOI：10.1021/jf1023643

  日期：2010.9.22

  Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC(50) = 3.30 mu M (E(max) = 100%, n = 7) and 2,4-dihydroxy-4'-methoxydeoxybenzoin EC(50) = 3.70 mu M (E(max) = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H >= p-OMe > p-OH > o-OMe > m,p-diOMe >= m-OMe.
• Free-Radical-Scavenging, Antityrosinase, and Cellular Melanogenesis Inhibitory Activities of Synthetic Isoflavones
  作者：Tzy-Ming Lu、Horng-Huey Ko、Lean-Teik Ng、Yen-Pin Hsieh

  DOI：10.1002/cbdv.201400208

  日期：2015.6

  potential of synthetic isoflavones for application in cosmeceuticals. Twenty‐five isoflavones were synthesized and their capacities of free‐radical‐scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further

  在这项研究中，我们研究了合成异黄酮在药妆品中的应用潜力。合成了 25 种异黄酮，并评估了它们清除自由基和抑制蘑菇酪氨酸酶的能力，以及它们对 B16F10 鼠黑色素瘤细胞和 HaCaT 人角质形成细胞的细胞活力的影响。进一步研究了显示出显着蘑菇酪氨酸酶抑制活性的异黄酮在体外 B16F10 黑素细胞中减少细胞黑色素形成和抗酪氨酸酶活性。在测试的异黄酮中，6-羟基黄豆苷元 (2) 是 ABTS.+ 和 DPPH 的最强清除剂。SC50 值分别为 11.3±0.3 和 9.4±0.1 μM 的自由基。Texasin (20) 表现出最有效的蘑菇酪氨酸酶抑制作用 (IC50 14.9±4.5 μM)，而 retusin (17) 分别显示出对 B16F10 黑素细胞中细胞黑色素形成和抗酪氨酸酶活性的最有效抑制。总之，retusin (17) 和 texasin (20) 都表现出强大的自由基清除能力
• Potential antioxidants and tyrosinase inhibitors from synthetic polyphenolic deoxybenzoins
  作者：Lean-Teik Ng、Horng-Huey Ko、Tzy-Ming Lu

  DOI：10.1016/j.bmc.2009.05.019

  日期：2009.7

  Deoxybenzoins (DOBs) are one-pot synthetic precursors of isoflavones with feature analogous to those beneficial polyphenols such as resveratrol (stilbene) and phloretin (dihydrochalcone). In this study, seventeen polyphenolic DOBs were synthesized and evaluated by various antioxidant assays and tyrosinase inhibitory effect in vitro. Results displayed that these DOBs are powerful antioxidants; for example, 2,3,4-trihydroxy-3',4'-dimethoxydeoxybenzoin possesses an excellent anti-lipid peroxidation activity (IC50 = 0.72 +/- 0.16 mu M), whilst 2,4,4',5-tetrahydroxydeoxybenzoin showed good DPPH radical scavenging activity (IC50 = 0.69 +/- 0.04 mu M), which were better than Trolox and vitamin C. Besides exhibiting a weak metal chelating effect, these DOBs were effective in scavenging ABTS(center dot+) and superoxide anion (O-2(center dot-)) radicals. DOBs also exhibited potent mushroom tyrosinase inhibitory activity; for example 2,3,4'-trihydroxy4- methoxydeoxybenzoin displayed stable and significant inhibitory effect on tyrosinase activity, with IC50 values 43.37, 43.10 and 46.10 mu M at incubation intervals of 0.5, 1.5, and 2.5 h, respectively. These results suggest that, with the advantage of being readily synthesizable small molecules, DOBs can be potentially developed into clinical and industrial antioxidants. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.