namakochrome | 476-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: namakochrome
• 英文别名: 2,5,6,7,8-pentahydroxy-3-methoxynaphthalene-1,4-dione
• CAS: 476-38-0
• 化学式: C₁₁H₈O₈
• 分子量: 268.18
• InChiKey: CVWLIMZLKJUGMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  145
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  spinochrome E 在 硫酸 、 水 、 potassium carbonate 作用下， 以 乙醚 、 乙酸乙酯 、 乙腈 为溶剂， 反应 5.0h， 生成 namakochrome
  参考文献：
  名称：

  Preparative Monomethylation of 2,3,5,6,7,8-Hexahydroxynaphthalene-1,4-dione (Spinochrome E). The First Direct Synthesis of Namakochrome: the Natural Pigment of the Holothurian Polycheira rufescens

  摘要：

  A 4-step preparative conversion of the available sea urchins pigment spinochrome E into the holothurian Polycheira rufescens pigment namakochrome was developed. Spinochrome E was converted into hexaacetate, and one beta-acetate group in the quinone core of the latter was selectively removed. The resulting pentaacetate was treated with diazomethane, and all protective acetate groups were removed by treatment with methanolic HCl. The total yield of namakochrome over 4 steps was similar to 46-51%.

  DOI：

  10.1134/s1070428020020050

文献信息

• [EN] SKIN BONDING PROCESS<br/>[FR] PROCESSUS D'ADHESION CUTANEE
  申请人：UNIV CREIGHTON

  公开号：WO2006107827A1

  公开（公告）日：2006-10-12

  [EN] The present invention relates to methods of providing a desired effect to the skin of a mammal using a Maillard initiating reagent with a skin-modifying compound.
  [FR] La présente invention concerne des procédés permettant d'obtenir un effet souhaité sur la peau d'un mammifère en utilisant une réaction de Maillard avec un composé modifiant la peau.
• Preparative Monomethylation of 2,3,5,6,7,8-Hexahydroxynaphthalene-1,4-dione (Spinochrome E). The First Direct Synthesis of Namakochrome: the Natural Pigment of the Holothurian Polycheira rufescens
  作者：S. G. Polonik、V. A. Denisenko、R. S. Popov、A. A. Artjukov、Y. E. Sabutskii

  DOI：10.1134/s1070428020020050

  日期：2020.2

  A 4-step preparative conversion of the available sea urchins pigment spinochrome E into the holothurian Polycheira rufescens pigment namakochrome was developed. Spinochrome E was converted into hexaacetate, and one beta-acetate group in the quinone core of the latter was selectively removed. The resulting pentaacetate was treated with diazomethane, and all protective acetate groups were removed by treatment with methanolic HCl. The total yield of namakochrome over 4 steps was similar to 46-51%.