2-(ethoxymethyl)-5-hydroxy-4H-pyran-4-one | 135100-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(ethoxymethyl)-5-hydroxy-4H-pyran-4-one
• 英文别名: 2-ethoxymethyl-5-hydroxy-gamma-pyrone；2-(ethoxymethyl)-5-hydroxypyran-4-one
• CAS: 135100-43-5
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: GCMPGTUGHASJNO-UHFFFAOYSA-N

物化性质

• 沸点：
  311.8±42.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(ethoxymethyl)-5-hydroxy-4H-pyran-4-one 在 sodium hydroxide 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 3-Benzyloxy-6-ethoxymethyl-2-hydroxymethyl-pyran-4-one
  参考文献：
  名称：

  The monoethyl ester of meconic acid is an active site inhibitor of HCV NS5B RNA-dependent RNA polymerase

  摘要：

  Screening of the in-house sample collection for compounds with HCV NS5B RNA dependent RNA polymerase inhibition led to the identification of a new lead. Afterwards, we discovered that the screening lead, rather than containing the expected structure 1, was comprised of roughly a 1:1 mixture of meconic acid 2 and its monoethyl ester 3, with all inhibitory potency residing with 3. We propose that this compound shares critical common features for activity with alpha,gamma-diketoacids inhibitors previously discovered by our group. SAR around this molecule will be presented to provide an improved basis for structure-based ligand design. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.087
• 作为产物：
  描述：

  2-(Ethoxymethyl)-5-phenylmethoxypyran-4-one 在 盐酸 作用下， 反应 2.0h， 以46%的产率得到2-(ethoxymethyl)-5-hydroxy-4H-pyran-4-one
  参考文献：
  名称：

  羟基吡喃酮和羟基吡啶酮的合成，理化性质和生物学评估：用于细胞标记的新型双齿配体。

  摘要：

  描述了一系列可能与铟（III）螯合的羟基吡喃酮和羟基吡啶酮。给出了两种铟配合物的晶体结构。报告了配体和相应的铁（III），镓（III）和铟（III）配合物的分布系数。在铁和镓配合物与铁和铟配合物的分布系数之间获得了良好的线性关系。相反，在游离配体的分布系数与三组配合物的分布系数之间获得了非线性关系。后一种关系用于鉴定具有最佳细胞标记特性的化合物。已经将两种这样的化合物（6-（烷氧基甲基）-3-羟基-4H-吡喃-4-酮）与托酚酮比较了它们用111 In标记人白细胞的能力。所选配体的白细胞标记效率更高，体外血浆稳定性与111In-对羟基苯甲酸类似。这些结果表明，新的双齿配体可能比目前用于细胞标记的配体具有优势。

  DOI：

  10.1021/jm960220g

文献信息

• Hydroxamic acid and its derivatives as inhibitors of melanocyte tyrosinase for topical skin lighteners
  申请人：Integriderm, Inc.

  公开号：US20030199558A1

  公开（公告）日：2003-10-23

  Methods, compounds, and formulations are provided to reduce pigmentation in mammalian skin, comprising hydroxamic acid and its derivatives, and especially benzohydroxamic acid and its derivatives. The compounds preferably inhibit pigment synthesis in melanocytes through inhibition of melanocyte tyrosinase. The methods can be used for lightening skin, and for treating uneven skin complexions, which result from hyperpigmentation-related medical conditions such as melasma, age spots, freckles, ochronosis, and lentigo. The compounds can be used medically or cosmetically, and preferably as topical formulations.

  提供了一种用于减少哺乳动物皮肤色素沉着的方法、化合物和配方，包括羟羧酸及其衍生物，尤其是苯甲羟羧酸及其衍生物。这些化合物通过抑制黑素细胞酪氨酸酶的活性，从而抑制黑色素合成。这些方法可用于美白皮肤，治疗因色素沉着相关医疗状况（如雀斑、老年斑、晒斑、黑变病和雀斑）而导致的不均匀肤色。这些化合物可在医学上或美容上使用，最好作为局部制剂。
• Synthesis, Physicochemical Properties, and Biological Evaluation of Hydroxypyranones and Hydroxypyridinones:  Novel Bidentate Ligands for Cell-Labeling
  作者：Beverley L. Ellis、Anne K. Duhme、Robert C. Hider、M. Bilayet Hossain、Safia Rizvi、Dick van der Helm

  DOI：10.1021/jm960220g

  日期：1996.1.1

  The synthesis of a range of hydroxypyranones and hydroxypyridinones with potential for the chelation of indium(III) is described. The crystal structures of two of the indium complexes are presented. The distribution coefficients of the ligands and the corresponding iron(III), gallium(III), and indium(III) complexes are reported. Good linear relationships between the distribution coefficients of the

  描述了一系列可能与铟（III）螯合的羟基吡喃酮和羟基吡啶酮。给出了两种铟配合物的晶体结构。报告了配体和相应的铁（III），镓（III）和铟（III）配合物的分布系数。在铁和镓配合物与铁和铟配合物的分布系数之间获得了良好的线性关系。相反，在游离配体的分布系数与三组配合物的分布系数之间获得了非线性关系。后一种关系用于鉴定具有最佳细胞标记特性的化合物。已经将两种这样的化合物（6-（烷氧基甲基）-3-羟基-4H-吡喃-4-酮）与托酚酮比较了它们用111 In标记人白细胞的能力。所选配体的白细胞标记效率更高，体外血浆稳定性与111In-对羟基苯甲酸类似。这些结果表明，新的双齿配体可能比目前用于细胞标记的配体具有优势。
• 2-ethoxymethyl-5-hydroxy-gamma-pyrone and melanogenesis-inhibiting
  申请人：Sansho Seiyaku Co., Ltd.

  公开号：US05102661A1

  公开（公告）日：1992-04-07

  The compound 2-ethoxymethyl-5-hydroxy-.gamma.-pyrone and a melanogenesis-inhibiting endermic preparation for external application containing the compound as an active ingredient. The endermic preparations are almost non-toxic and have an extremely high melanogenesis-inhibiting activity.

  化合物2-乙氧甲基-5-羟基-.gamma.-吡喃酮及其作为活性成分的外用美白制剂。这些美白制剂几乎无毒，并具有极高的抑制黑色素生成活性。
• EXTRACT POWDER OF INDIGO PLANT, AND ITS PREPARATION AND USES
  申请人：Fujii Mitsukiyo

  公开号：US20100034757A1

  公开（公告）日：2010-02-11

  The present invention has objects to provide an extract powder of indigo plant, which has a relatively low hygroscopicity, satisfactory fluidability, and improved storage stability; a process thereof; and a composition incorporated with the extract powder. The objects are solved by a process for producing an extract powder of indigo plant, which comprises incorporating a partial starch hydrolyzate with a dextrose equivalent of 10.2 or lower into one part by weight, on a dry solid basis, of an indigo plant extract contained in a liquid extract of indigo plant in an amount of not lower than 0.25 part by weight but not higher than 5 parts by weight, on a dry solid basis, and drying the resulting mixture; an extract powder of indigo plant prepared thereby; and a composition incorporated with the extract powder.

  本发明旨在提供一种靛蓝植物的提取粉末，其具有相对较低的吸湿性、满意的流动性和改善的储存稳定性；其制备方法；以及与提取粉末混合的组合物。通过将DE值为10.2或更低的部分淀粉水解物以不低于0.25份重量但不高于5份重量的干固物基础加入到液态提取的靛蓝植物提取物的一份重量中，并将所得混合物干燥，来解决上述问题；由此制备的靛蓝植物提取粉末；以及与提取粉末混合的组合物。
• 2-Ethoxymethyl-5-hydroxy-gamma-pyrone and melanogenesis-inhibiting endermic preparation containing the same compound as active ingredient
  申请人：Sansho Seiyaku Co., Ltd.

  公开号：EP0417632A2

  公开（公告）日：1991-03-20

  Disclosed are 2-ethoxymethyl-5-hydroxy-γ-pyrone and an melanogenesis-inhibiting endermic preparation for external application containing the compound as an active ingredient. The endermic preparation is almost non-toxic and has an extremely high melanogenesis-­inhibiting activity.

  本发明公开了 2-乙氧基甲基-5-羟基-γ-吡喃酮和含有该化合物作为活性成分的外用黑色素生成抑制内服制剂。这种外用制剂几乎无毒，而且具有极高的黑色素生成抑制活性。