spinochrome E | 476-37-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: spinochrome E
• 英文别名: Spinochrom E；2,3,5,6,7,8-hexahydroxy-1,4-naphthoquinone；2,3,6,7-tetrahydroxynaphthazarin；Hexahydroxy-2,3-naphthalenedione；2,3,5,6,7,8-hexahydroxynaphthalene-1,4-dione
• CAS: 476-37-9
• 化学式: C₁₀H₆O₈
• 分子量: 254.153
• InChiKey: RUQPQFLYDCXMGX-UHFFFAOYSA-N

物化性质

• 熔点：
  187-188 °C
• 沸点：
  770.8±60.0 °C(Predicted)
• 密度：
  2.392±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  156
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  spinochrome E 在 硫酸 、 水 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 、 苯 为溶剂， 反应 5.0h， 生成 2,3,6,7,8-pentaacetoxy-5-hydroxynaphthalene-1,4-dione
  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
• 作为产物：
  描述：

  1,2-bis-chloromethyl-3,4,5,6-tetramethoxy-benzene 在 氢溴酸 作用下， 生成 spinochrome E
  参考文献：
  名称：

  天然存在的醌。第七部分 旋转色素E的合成

  摘要：

  通过3,4,5,6-四甲氧基邻苯二甲醛与乙二醛的缩合反应合成了Spinochrome E. hexahydroxy-1,4-萘醌。

  DOI：

  10.1039/j39660000426

文献信息

• Simple preparative synthesis of spinochrome e, a pigment from sea urchins of the genus Echinothrix
  作者：K. L. Borisova、V. F. Anufriev

  DOI：10.1007/s10600-012-0204-6

  日期：2012.5

  A preparative synthesis of spinochrome E (2,3,5,6,7,8-hexahydroxy-1,4-naphthoquinone, 1), a metabolite of sea urchins of the genus Echinothrix, is proposed starting from 2,3-dichloro-6,7-diethoxynaphthazarine (4) with simultaneous substitution of the Cl atoms by hydroxyl- and nitro-groups, reduction of the latter, and subsequent removal of alkoxy groups and hydrolysis of the amine in the resulting

  Spinochrome E (2,3,5,6,7,8-hexahydroxy-1,4-naphthoquinone, 1) 是 Echinothrix 属海胆的代谢物，建议从 2,3-二氯- 6,7-diethoxynaphthazarine (4) 同时用羟基和硝基取代 Cl 原子，还原后者，随后去除烷氧基并水解生成的 3-氨基-2-羟基- 6,7-二乙氧基萘扎林 (6)。
• A simple synthesis of natural spinazarins and their analogues
  作者：Dmitry N. Pelageev、Ksenia L. Borisova、Svetlana M. Kovach、Vyacheslav V. Makhankov、Victor Ph. Anufriev

  DOI：10.1016/j.mencom.2023.02.026

  日期：2023.3

  simple synthesis of spinazarins (2,3-dihydroxy-naphthazarins or 2,3,5,8-tetrahydroxy-1,4-naphtho-quinones) from available 2,3-dichloronaphthazarin derivatives involves replacement of chlorine atoms with azido groups followed by their acidic hydrolysis. The procedure can be used for the preparative synthesis of natural biologically active spinazarins and their analogues.

  从可用的 2,3-二氯萘并衍生物中简单合成 spinazarin（2,3-二羟基-萘并或 2,3,5,8-四羟基-1,4-萘并醌）涉及用叠氮基取代氯原子，然后通过它们的酸性水解。该程序可用于天然生物活性菠菜素及其类似物的制备合成。
• Use of quinones in the treatment of cancer or AIDS
  申请人：RADOPATH LIMITED

  公开号：EP0499467A2

  公开（公告）日：1992-08-19

  The invention relates to a pharmaceutical composition comprising at least one quinone and to its use in the treatment of disease, especially cancer and virus infections. The composition of the invention comprises at least one quinone dissolved or dispersed in a liquid diluent or carrier at a concentration of about 103 moles/litre or below, preferably down to 1018 moles/litre. In the composition the at least one quinone is preferably: An anthraquinone glycoside, more preferably carminic acid. A compound of the formula : wherein R1 is hydrogen, a sugar e.g. -C6H11O5, hydroxy, in which R5 is - CH2NHAc, - CH20H, - CH(NH2)C02H or -CH2NH2; R2 is methyl or -C02H ; R3 is hydrogen, -NH2 or - SO3X in which X is H, Na or K; and R4 is hydrogen or hydroxy. Quinhydrone of the formula : Tetrahydroxyquinone of the formula :

  本发明涉及一种包含至少一种醌的药物组合物及其在治疗疾病，特别是癌症和病毒感染中的用途。 本发明的组合物包含至少一种溶解或分散在液体稀释剂或载体中的醌，浓度约为 103 摩尔/升或更低，最好低至 1018 摩尔/升。 在组合物中，至少一种醌最好是： 蒽醌苷，更优选卡米酸。 式......的化合物： 其中 R1 是氢、糖如-C6H11O5、羟基、 其中 R5 是-CH2NHAc、-CH20H、-CH(NH2)C02H 或-CH2NH2；R2 是甲基或-C02H；R3 是氢、-NH2 或-SO3X，其中 X 是 H、Na 或 K；R4 是氢或羟基。式中的......四氢酮 式中的四羟基醌
• PERITONEAL THERAPEUTIC FLUID
  申请人：Opterion Health AG

  公开号：EP3120842A1

  公开（公告）日：2017-01-25

  Peritoneal therapeutic fluid comprising one or more of a biocompatibility enhancing agent (BCA) that is selected from the group consisting of a polyphenolic compound, a metabolite of a polyphenolic compound which is obtained by metabolization in the human or animal body, a salt or a glycoside of a polyphenolic compound.

  含有一种或多种生物相容性增强剂（BCA）的腹膜治疗液，这种生物相容性增强剂选自多酚类化合物、多酚类化合物在人或动物体内代谢产生的代谢产物、多酚类化合物的盐或糖苷组成的组。
• AQUEOUS SOLUTION COMPRISING A POLYPHENOL
  申请人：Opterion Health AG

  公开号：EP3120838A1

  公开（公告）日：2017-01-25

  Aqueous solution, comprising, in dissolved state, - at least one polyphenolic compound (e. g. resveratrol or piceid) - at least one saccharide (e. g. glucose or icodextrin), and method for increasing the solubility of a polyphenolic compound in water

  水溶液，以溶解状态包含 - 至少一种多酚类化合物（如白藜芦醇或 piceid） - 至少一种糖类（如葡萄糖或冰糖糊精）、 以及提高多酚类化合物在水中溶解度的方法