2-己酰-1,3,6,8-四羟基蒽-9,10-二酮 | 10254-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 2-己酰-1,3,6,8-四羟基蒽-9,10-二酮
• 英文名称: norsolorinic acid
• 英文别名: 2-hexanoyl-1,3,6,8-tetrahydroxyanthracene-9,10-dione
• CAS: 10254-99-6
• 化学式: C₂₀H₁₈O₇
• 分子量: 370.359
• InChiKey: XIJDBHLQUYAZJI-UHFFFAOYSA-N

物化性质

• 熔点：
  256-257 °C
• 沸点：
  584.9±50.0 °C(Predicted)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 海关编码：
  2914690090

反应信息

• 作为反应物：
  描述：

  2-己酰-1,3,6,8-四羟基蒽-9,10-二酮 在 metabolite-free SU-1 cell-free extract 、 S-Adenosylmethionine 、 还原型辅酶II(NADPH)四钠盐 、 腺嘌呤黄素 作用下， 以 水 为溶剂， 反应 8.0h， 生成 黄曲霉毒素 B1
  参考文献：
  名称：

  The in Vitro Conversion of Norsolorinic Acid to Aflatoxin B₁. An Improved Method of Cell-Free Enzyme Preparation and Stabilization

  摘要：

  The biosynthesis of the environmental carcinogen aflatoxin B(1) (13) is initiated by the formation of a C(6)-primer by a dedicated yeast-like fatty acid synthase. Homologation of this starter unit by a polyketide synthase gives the anthraquinone norsolorinic acid (2). Approximately 15 chemical steps follow from this first stable intermediate to the mycotoxin (13) itself. A new protocol of cell-free enzyme preparation has been developed from the fungus Aspergillus parasiticus which carries out all of these transformations for the first time. The key experimental step involves rapid concentration and efficient dialysis by membrane filtration to remove primary and secondary metabolites, cofactors, and small biomolecules (MW < 10 000). All enzymes of the aflatoxin biosynthetic pathway have been dramatically stabilized by this procedure, and the effects of added substrates and cofactors can be assayed against virtually no background reactions. The overall pathway from norsolorinic acid (2) to aflatoxin B1 (13) has been investigated, cofactor requirements defined for each step, and a time-course run in which only versicolorin A (9) and sterigmatocystin (11) were observed to accumulate. The post-bisfuran skeletal rearrangement of versicolorin A (9) to demethylsterigmatocystin (10) was studied in O-methylsterigmatocystin (12) in the presence of D(2)O and/or d(7)-glucose or stereospecifically labeled NADPD. Unexpectedly high extents of proton exchange were found in the A ring during this transformation, including at a site of formal reduction. A tentative mechanism is discussed to account for this multi enzyme process.

  DOI：

  10.1021/ja974367o
• 作为产物：
  描述：

  1,1,3-tris(trimethylsiloxy)-1,3-butadiene 、 3-chloro-6-hexanoyl-7-hydroxyjuglone 在 盐酸 作用下， 以81%的产率得到2-己酰-1,3,6,8-四羟基蒽-9,10-二酮
  参考文献：
  名称：

  Cycloaddition of Cross-Conjugated Trienes to Halogenated Quinones

  摘要：

  我们研究了富电子交叉共轭三烯和卤代醌的 [4 + 2] 环加成反应的化学选择性。该方法改进了 6-乙酰基-2,3,7-三羟基丁酮、索罗林酸和诺沙林酸以及艾维林的制备方法。它还证实了所提出的血塞通和 3,8-二羟基-4-甲氧基-2-甲氧基羰基-1-甲基-蒽醌的结构，但否定了 sopheranin 的结构。

  DOI：

  10.1055/s-1994-25553

文献信息

• Cycloaddition of Cross-Conjugated Trienes to Halogenated Quinones
  作者：Michel Couturier、Paul Brassard

  DOI：10.1055/s-1994-25553

  日期：——

  The chemoselectivity of [4 + 2] cycloadditions involving electronrich cross-conjugated trienes and halogenated quinones has been examined. The approach provides improved preparations of 6-acetyl-2,3,7-trihydroxyjuglone, solorinic and norsolorinic acids, and averythrin. It also confirms the structure proposed for haematommone and 3,8-dihydroxy-4-methoxy-2-methoxycarbonyl-1-methyl-anthraquinone but invalidates that of sopheranin.

  我们研究了富电子交叉共轭三烯和卤代醌的 [4 + 2] 环加成反应的化学选择性。该方法改进了 6-乙酰基-2,3,7-三羟基丁酮、索罗林酸和诺沙林酸以及艾维林的制备方法。它还证实了所提出的血塞通和 3,8-二羟基-4-甲氧基-2-甲氧基羰基-1-甲基-蒽醌的结构，但否定了 sopheranin 的结构。
• The in Vitro Conversion of Norsolorinic Acid to Aflatoxin B₁. An Improved Method of Cell-Free Enzyme Preparation and Stabilization
  作者：Coran M. H. Watanabe、Craig A. Townsend

  DOI：10.1021/ja974367o

  日期：1998.7.1

  The biosynthesis of the environmental carcinogen aflatoxin B(1) (13) is initiated by the formation of a C(6)-primer by a dedicated yeast-like fatty acid synthase. Homologation of this starter unit by a polyketide synthase gives the anthraquinone norsolorinic acid (2). Approximately 15 chemical steps follow from this first stable intermediate to the mycotoxin (13) itself. A new protocol of cell-free enzyme preparation has been developed from the fungus Aspergillus parasiticus which carries out all of these transformations for the first time. The key experimental step involves rapid concentration and efficient dialysis by membrane filtration to remove primary and secondary metabolites, cofactors, and small biomolecules (MW < 10 000). All enzymes of the aflatoxin biosynthetic pathway have been dramatically stabilized by this procedure, and the effects of added substrates and cofactors can be assayed against virtually no background reactions. The overall pathway from norsolorinic acid (2) to aflatoxin B1 (13) has been investigated, cofactor requirements defined for each step, and a time-course run in which only versicolorin A (9) and sterigmatocystin (11) were observed to accumulate. The post-bisfuran skeletal rearrangement of versicolorin A (9) to demethylsterigmatocystin (10) was studied in O-methylsterigmatocystin (12) in the presence of D(2)O and/or d(7)-glucose or stereospecifically labeled NADPD. Unexpectedly high extents of proton exchange were found in the A ring during this transformation, including at a site of formal reduction. A tentative mechanism is discussed to account for this multi enzyme process.