4-O-propanoyl-2-methoxyhydroquinone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-O-propanoyl-2-methoxyhydroquinone
• 英文别名: (4-Hydroxy-3-methoxyphenyl) propanoate
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: XORALDVCJCDBJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-methoxy-1,4-di-O-propanoylhydroquinone 在 Candida antarctica lipase B 作用下， 以 异丙醚 、 异丙醇 为溶剂， 反应 0.25h， 以6%的产率得到4-O-propanoyl-2-methoxyhydroquinone
  参考文献：
  名称：

  Candida antarctica lipase B-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxy groups

  摘要：

  南极酵母催化的脂肪酶B在脱酰基化取代的对羟基苯酚和间苯二酚上表现出高活性。脱酰基化反应比同一酶催化的这些二羟基苯酚的直接酰化要快得多。更重要的是，它们通常以明显的区域选择性方式进行：远离取代基的酰氧基被优先裂解。主要或独家获得的产物是通过对二羟基苯酚的直接酰化产生的同分异构体。对于烷基取代的对羟基苯醌衍生物，随着取代基体积的增加，区域选择性增加。对于4-取代的二酰基间苯二酚，通常获得3-O-单酰基衍生物作为唯一产物。有趣的是，在这些酶催化的脱酰化反应中，一些次生醇被证明比相应的一次醇更好地作为酰基受体。

  DOI：

  10.1139/cjc-2015-0335

文献信息

• Highly regioselective propanoylation of dihydroxybenzenes mediated by Candida antarctica lipase B in organic solvents
  作者：Toshifumi Miyazawa、Manabu Hamada、Ryohei Morimoto、Takashi Murashima、Takashi Yamada

  DOI：10.1016/j.tetlet.2007.10.124

  日期：2008.1

  Candida antarctica lipase B (CAL-B) was found to be a highly active biocatalyst for the direct acylation of the phenolic hydroxyls of substituted hydroquinones and resorcinols with vinyl propanoate as an acyl donor. The acylation reactions took place generally in a very regioselective manner. Especially in the case of 4-substituted resorcinols, the hydroxyl remote from the substituent was regiospecifically

  已发现南极假丝酵母脂肪酶B（CAL-B）是一种高活性生物催化剂，可将丙酸乙烯酯作为酰基供体直接取代取代的对苯二酚和间苯二酚的酚羟基。酰化反应通常以非常区域选择性的方式发生。特别是在4-取代的间苯二酚的情况下，远离取代基的羟基被区域特异性地酰化，仅得到1- O-丙酰基化的间苯二酚。
• Candida antarctica lipase B-mediated regioselective acylation of dihydroxybenzenes in organic solvents
  作者：Toshifumi Miyazawa、Manabu Hamada、Ryohei Morimoto、Yuki Maeda

  DOI：10.1016/j.tet.2015.04.033

  日期：2015.6

  Candida antarctica lipase B proved to be a highly active biocatalyst for the direct acylation of phenolic hydroxy groups of substituted hydroquinones and resorcinols, which have rarely been reported so far. More importantly, the acylation reactions took place generally in a markedly regioselective manner: the hydroxy group remote from the substituent was preferentially acylated. In the case of substituted

  南极假丝酵母脂肪酶B被证明是一种高活性生物催化剂，可直接酰化取代的对苯二酚和间苯二酚的酚羟基，到目前为止，鲜有报道。更重要的是，酰化反应通常以明显的区域选择性方式发生：远离取代基的羟基优先被酰化。在取代氢醌的情况下，选择性随取代基体积的增加而增加。有趣的是，在4-取代的间苯二酚的情况下，作为唯一产物获得了1- O-单酰化的衍生物。
• METHOD AND KIT FOR DETECTION OF GUAIACOL-PRODUCING BACTERIUM
  申请人：Calpis Co., Ltd.

  公开号：EP2444502A1

  公开（公告）日：2012-04-25

  Disclosed is a method for detecting guaiacol-producing bacteria in a specimen comprising culturing the specimen or a dilution thereof on a plate of a solid medium for acidophilic bacteria comprising a compound represented by the following formula, wherein R is -H, -OH, -C(O)H, -C(O)CH3, -COOH, C1-C3 alkyl or C1-C3 alkenyl, wherein alkyl and alkenyl may optionally be substituted by -OH, -C(O) H or -COOH); and detecting a colony formed on the solid medium. According to preferred embodiments, the solid medium for acidophilic bacteria comprises 50 ppm or more of vanillic acid and the plate culture is carried out at 20°C to 55°C. The present invention also provides a solid medium for acidophilic bacteria and a kit for detection of guaiacol-producing bacteria in a specimen. According to the present invention, guaiacol-producing bacteria present in a specimen such as fruit juice raw materials can be detected rapidly in a simple manner.

  本发明公开了一种检测标本中产生愈创木酚的细菌的方法，该方法包括将标本或其稀释液培养在嗜酸性细菌固体培养基的平板上，该培养基包含下式所代表的化合物，其中R为-H、-OH、-C(O)H、-C(O)CH3、-COOH、C1-C3烷基或C1-C3烯基，其中烷基和烯基可任选被-OH、-C(O)H或-COOH取代；检测在固体培养基上形成的菌落。根据优选的实施方案，嗜酸性细菌的固体培养基包含 50ppm 或更多的香草酸，平板培养在 20°C 至 55°C 下进行。本发明还提供了一种嗜酸性细菌固体培养基和一种检测标本中愈创木酚产生菌的试剂盒。根据本发明，可以用简单的方法快速检测果汁原料等标本中的愈创木酚细菌。
• Secondary alcohols act as better nucleophiles than primary alcohols in the lipase-catalyzed regioselective deacylation of dihydroxybenzenes acylated at both phenolic hydroxyls
  作者：Toshifumi Miyazawa、Manabu Hamada、Ryohei Morimoto、Takashi Murashima、Takashi Yamada

  DOI：10.1016/j.tetlet.2007.09.104

  日期：2007.11

  Candida antarctica lipase B (CAL-B) was found to be highly regioselective as well as active in the deacylation of resorcinols and hydroquinones acylated at both phenolic hydroxyls. Contrary to expectation, secondary alcohols acted as better nucleophiles than primary alcohols in these enzymatic deacylations. (C) 2007 Elsevier Ltd. All rights reserved.
• US8921059B2
  申请人：——

  公开号：US8921059B2

  公开（公告）日：2014-12-30