1-(2,4-二羟基苯基)-2-(4-羟基-3-甲氧基苯基)乙酮 | 40456-49-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(2,4-二羟基苯基)-2-(4-羟基-3-甲氧基苯基)乙酮
• 英文名称: 1-(2,4-dihydroxyphenyl)-2-(4'-hydroxy-3'-methoxyphenyl)ethanone
• 英文别名: 3'-methoxy-2,4,4′-trihydroxydeoxybenzoin；1-(2,4-Dihydroxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-ethanone；1-(2,4-dihydroxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)ethanone
• CAS: 40456-49-3
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: VXAPZUPSWVIAQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  516.2±40.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

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：

  1-(2,4-二羟基苯基)-2-(4-羟基-3-甲氧基苯基)乙酮 在 甲基磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以94%的产率得到7,4'-二羟基-3'-甲氧基异黄酮
  参考文献：
  名称：

  Waehaelae, Kristiina; Hase, Tapio A., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3005 - 3008

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 4-benzyloxy-3-methoxyphenylethanoate 在 palladium on activated charcoal 氢氧化钾 、 三氟化硼乙醚 、 氢气 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 1-(2,4-二羟基苯基)-2-(4-羟基-3-甲氧基苯基)乙酮
  参考文献：
  名称：

  Waehaelae, Kristiina; Hase, Tapio A., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3005 - 3008

  摘要：

  DOI：

文献信息

• USE OF 3-(3-HYDROXY-4-METHOXY-PHENYL)-1-(2,4,6-TRIHYDROXY-PHENYL) PROPAN-1-ONE
  申请人：SYMRISE AG

  公开号：US20190343777A1

  公开（公告）日：2019-11-14

  The present invention concerns the use of 3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one for masking, reducing or suppressing an unpleasant taste impression, preferably bitter, sour and/or astringent taste impression of unpleasant-tasting substances or mixture of substances, preferably bitter-, sour-, and/or astringent-tasting substances or mixtures of substances, and in particular the bitter taste impression of bitter-tasting substances, and/or modulating the taste impressions selected from the group consisting of cooling, umami, fruity and spicy notes of cooling-, umami-, fruity- or spicy-tasting substances or mixture of substances, and simultaneously intensifying the sweet-taste impression of sweet-tasting substances or mixtures of substances or both sweet- and bitter-tasting tasting substances or mixture of substances.

  本发明涉及使用3-(3-羟基-4-甲氧基苯基)-1-(2,4,6-三羟基苯基)丙酮来掩盖、减少或抑制令人不愉快的味觉印象，优选是苦、酸和/或涩的不愉快味觉印象的不愉快味道物质或物质混合物，优选是苦味、酸味和/或涩味物质或物质混合物，特别是苦味物质的苦味印象，和/或调节选自冷却、鲜味、果味和辛辣味的味觉印象的味道物质或物质混合物，同时增强甜味物质或物质混合物或甜味和苦味物质或物质混合物的甜味印象。
• Synthesis of Various Kinds of Isoflavones, Isoflavanes, and Biphenyl-Ketones and Their 1,1-Diphenyl-2-picrylhydrazyl Radical-Scavenging Activities
  作者：Hideyuki Goto、Yoshiyasu Terao、Shuji Akai

  DOI：10.1248/cpb.57.346

  日期：——

  Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10′) were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1-diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12—54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E—I) and their biphenyl-ketone derivatives (10E—H) also showed a high activity (ED50=<50 μM), while all of their corresponding isoflavones (8E—I) were not active at all. The 7-hydroxyisoflavanes having either an additional hydroxyl group at the C5-position (9D) or a methoxy group at the C6-position (9J) presented a high activity (ED50=26—32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3′-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10′) by metabolism or biotransformation.

  合成了四十八种异黄酮（8）、三十一种异黄烷（9）以及四十七种联苯酮（10, 10′），这些化合物是由十一种取代酚（11）和六种苯乙酸（12）合成的。其中，有七十五种化合物是新发现的。这些化合物的自由基清除活性在pH 6.0下使用1,1-二苯基-2-吡唑啉酮（DPPH）进行了评估。我们发现，在四十三种含有儿茶酚基的化合物中，三十九种在A环或B环上表现出与儿茶素相似的高活性（ED50=12—54 μM）。在这些情况下，它们结构的其他部分似乎对活性影响不大。许多6-或8-羟基异黄烷（9E—I）及其联苯酮衍生物（10E—H）也显示出高活性（ED50=<50 μM），而它们对应的异黄酮（8E—I）则完全没有活性。具有在C5位增加羟基（9D）或在C6位增加甲氧基（9J）的7-羟基异黄烷则展现出高活性（ED50=26—32 μM）。本研究表明，天然异黄酮通过在C6、C8或C3′位置的羟基化，或通过代谢或生物转化形成异黄烷（9）和/或联苯酮衍生物（10′），具有表现抗氧化活性的可能性。
• USE OF HYDROXYFLAVAN DERIVATIVES FOR TASTE MODIFICATION
  申请人：Wessjohann Ludger

  公开号：US20100292175A1

  公开（公告）日：2010-11-18

  The present invention primarily relates to the use of specific compounds of formula (I) or of specific salts of a compound of formula (I) or mixtures thereof for synergistically enhancing the sweet taste of a sweet-tasting substance.

  本发明主要涉及使用特定的化合物(I)的盐或混合物，以协同增强甜味物质的甜味。
• OXALIC ACID DERIVATIVES AND USE THEREOF AS PHYSIOLOGICAL COOLING ACTIVE INGREDIENTS
  申请人：Surburg Horst

  公开号：US20090054520A1

  公开（公告）日：2009-02-26

  The present invention relates to specific oxalic acid derivatives and to corresponding mixtures and to uses thereof as physiological cooling active ingredients.

  本发明涉及特定草酸衍生物，以及相应的混合物，以及将其用作生理降温活性成分的用途。
• TEETH CLEANING COMPOUND CONTAINING MENTHOL WITH REDUCED BITTER SENSATION
  申请人：Oertling Heiko

  公开号：US20110081303A1

  公开（公告）日：2011-04-07

  The present invention primarily concerns teeth cleaning compounds containing menthol for use with a toothbrush, preferably tooth pastes, tooth crèmes, tooth cleaning gels or tooth powders. Such a tooth cleaning compound according to the invention contains menthol and a quantity, for masking the bitterness of the menthol, of menthane carboxylic acid-N-(4-methoxyphenyl)-amide (WS-12) of the following formula (Ia), in particular of the following formula (Ib), i.e. L-menthane carboxylic acid-N-(4-methoxyphenyl)-amide. The present invention also concerns the use of menthane carboxylic acid-N-(4-methoxyphenyl)-amide (WS-12) of the formulas (Ia) or (preferably) (Ib) to mask the bitter taste of menthol in a teeth cleaning compound. The present invention also concerns a method for dissolving menthane carboxylic acid-N-(4-methoxyphenyl)-amide (WS-12) in a teeth cleaning compound and a method for masking the bitterness of menthol in a teeth cleaning compound.

  本发明主要涉及含有薄荷脑的牙齿清洁化合物，用于配合牙刷使用，最好是牙膏、牙膏、牙齿清洁凝胶或牙粉。根据本发明的这种牙齿清洁化合物含有薄荷脑和一定量的用于掩盖薄荷脑苦味的薄荷酸-N-(4-甲氧基苯基)-酰胺（WS-12），其化学式为(Ia)，特别是以下化学式(Ib)，即L-薄荷酸-N-(4-甲氧基苯基)-酰胺。本发明还涉及使用化学式(Ia)或(更好地) (Ib)的薄荷酸-N-(4-甲氧基苯基)-酰胺（WS-12）来掩盖牙齿清洁化合物中薄荷脑的苦味。本发明还涉及一种溶解薄荷酸-N-(4-甲氧基苯基)-酰胺（WS-12）在牙齿清洁化合物中的方法，以及一种掩盖牙齿清洁化合物中薄荷脑苦味的方法。