Araneosol; 5,7-二羟基-3,4',6,8-四甲氧基黄酮 | 50461-86-4

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: Araneosol; 5,7-二羟基-3,4',6,8-四甲氧基黄酮
• 中文别名: Araneosol;5,7-二羟基-3,4',6,8-四甲氧基黄酮；5,7-二羟基-3,4',6,8-四甲氧基黄酮
• 英文名称: araneosol
• 英文别名: 5,7-dihydroxy-3,6,8-trimethoxy-2-(4-methoxyphenyl)chromen-4-one
• CAS: 50461-86-4
• 化学式: C₁₉H₁₈O₈
• 分子量: 374.347
• InChiKey: UZIFGCHUAVTVIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 海关编码：
  2914509090

反应信息

• 作为产物：
  描述：

  2,4-二甲氧基-1,3,5-三硝基苯 在 platinum(IV) oxide 盐酸 、 氢氧化钾 、 氢气 、 三乙胺 、 tin(ll) chloride 、 zinc(II) chloride 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 25.0~180.0 ℃ 、379.21 kPa 条件下， 反应 83.67h， 生成 Araneosol; 5,7-二羟基-3,4',6,8-四甲氧基黄酮
  参考文献：
  名称：

  Dutta, Pradeep K.; Bagchi, Debasis; Pakrashi, Satyesh C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 11, p. 1037 - 1038

  摘要：

  DOI：

文献信息

• Studies of the Selective<i>O</i>-Alkylation and Dealkylation of Flavonoids. XXI. A Convenient Method for Synthesizing 3,5,7-Trihydroxy-6,8-dimethoxyflavones and 5,7-Dihydroxy-3,6,8-trimethoxyflavones
  作者：Tokunaru Horie、Takeshi Kitou、Yasuhiko Kawamura、Kazuyo Yamashita

  DOI：10.1246/bcsj.69.1033

  日期：1996.4

  The Friedel–Crafts acetylation with boron trifluoride was studied and it was found that 1-(2,4-dihydroxy-3,5,6-trimethoxyphenyl)ethanone was conveniently synthesized from 2,3,5,6-tetramethoxyphenyl acetate in a mixture of acetic anhydride and acetic acid. 1-[2-Hydroxy-3,5,6-trimethoxy-4-(methoxymethoxy)phenyl]ethanone was cyclized to 7-hydroxy-5,6,8-trimethoxyflavone by using the Baker–Venkataraman transformation. The 7-benzyl ether of the flavone was oxidized with dimethyldioxirane and then treated with a small amount of p-toluenesulfonic acid to give 7-benzyloxy-3-hydroxy-5,6,8-trimethoxyflavone, which was converted into the methyl ether and tosylate. The 5-methoxy group in the methyl ether or tosylate was selectively cleaved with anhydrous aluminum bromide in acetonitrile under mild conditions to give the corresponding 5-hydroxyflavones and the latter compound with a 3-tosyloxy group was smoothly converted into the 3,5-dihydroxyflavone by hydrolysis with potassium carbonate in methanol. The hydrogenolysis of the 7-benzyloxy-3,5-dihydroxyflavone and its 3-methyl ether afforded quantitatively 3,5,7-trihydroxy-6,8-dimethoxyflavone and its 3-methyl ether. The process was suitable as a general method for synthesizing 3,5,7-trihydroxy-6,8-dimethoxyflavones and their 3-methyl ethers and the six flavones were synthesized for the clarification of their 1H and 13C NMR, MS, and UV spectral properties.

  研究了三氟化硼的 Friedel-Crafts 乙酰化反应，发现在乙酸酐和乙酸的混合物中，可以方便地从 2,3,5,6- 四甲氧基苯基乙酸酯合成 1-(2,4-二羟基-3,5,6-三甲氧基苯基)乙酮。1-[2-羟基-3,5,6-三甲氧基-4-（甲氧基甲氧基）苯基]乙酮通过贝克-文卡塔拉曼转化环化成 7-羟基-5,6,8-三甲氧基黄酮。黄酮的 7-苄基醚被二甲基二氧环己烷氧化，然后用少量对甲苯磺酸处理，得到 7-苄氧基-3-羟基-5,6,8-三甲氧基黄酮，并将其转化为甲醚和对甲苯磺酸盐。在温和的条件下，用无水溴化铝在乙腈中选择性地裂解甲醚或对甲苯磺酸盐中的 5-甲氧基，得到相应的 5-羟基黄酮，而后一种带有 3-对甲苯磺酸盐基团的化合物在甲醇中用碳酸钾水解，顺利地转化为 3,5-二羟基黄酮。通过氢解 7-苄氧基-3,5-二羟基黄酮及其 3-甲基醚，可定量得到 3,5,7-三羟基-6,8-二甲氧基黄酮及其 3-甲基醚。该方法适用于合成 3,5,7-三羟基-6,8-二甲氧基黄酮及其 3-甲基醚，合成的六种黄酮的 1H 和 13C NMR、MS 和 UV 光谱特性得到了澄清。
• Application of high flavonoid elite germplasm ‘CSR6R6-777’ in breeding for functional apple
  申请人：Shandong Agricultural University

  公开号：US11109548B2

  公开（公告）日：2021-09-07

  The present invention discloses an application of high-flavonoid elite germplasm CSR6R6-777 in apple breeding. The present invention seeks to protect use of an apple (Malus domestica) CSR6R6-777 in apple breeding. The deposition number of the apple (Malus domestica) CSR6R6-777 is CGMCC NO. 12468. The purpose of the breeding is to obtain an apple germplasm with excellent traits. The apple germplasm with excellent traits is an apple plant that meets the (a) and/or (b) and/or (c) and/or (d): (a) fully red-fleshed; (b) high-flavonoid content in the flesh; (c) high anthocyanin content in the flesh; (d) high antioxidant capacity of the flesh. The present application has great value for functional apple breeding.

  本发明公开了高类黄酮精英种质 CSR6R6-777 在苹果育种中的应用。本发明旨在保护苹果（Malus domestica）CSR6R6-777在苹果育种中的应用。苹果（Malus domestica）CSR6R6-777 的保藏编号为 CGMCC NO.12468.育种的目的是获得具有优良性状的苹果种质。具有优良性状的苹果种质是指符合(a)和/或(b)和/或(c)和/或(d)的苹果植株：(a)完全红肉；(b)果肉中类黄酮含量高；(c)果肉中花青素含量高；(d)果肉抗氧化能力强。本应用对功能性苹果育种具有重要价值。
• APPLICATION OF HIGH FLAVONOID ELITE GERMPLASM 'CSR6R6-777' IN BREEDING FOR FUNCTIONAL APPLE
  申请人：Shandong Agricultural University

  公开号：US20200267919A1

  公开（公告）日：2020-08-27

  The present invention discloses an application of high-flavonoid elite germplasm CSR6R6-777 in apple breeding. The present invention seeks to protect use of an apple ( Malus domestica ) CSR6R6-777 in apple breeding. The deposition number of the apple ( Malus domestica ) CSR6R6-777 is CGMCC NO.12468. The purpose of the breeding is to obtain an apple germplasm with excellent triats. The apple germplasm with excellent triats is an apple plant that meets the (a) and/or (b) and/or (c) and/or (d): (a) fully red-fleshed; (b) high-flavonoid content in the flesh; (c) high anthocyanin content in the flesh; (d) high antioxidant capacity of the flesh. The present application has great value for functional apple breeding.
• Dutta, Pradeep K.; Bagchi, Debasis; Pakrashi, Satyesh C., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 11, p. 1037 - 1038
  作者：Dutta, Pradeep K.、Bagchi, Debasis、Pakrashi, Satyesh C.

  DOI：——

  日期：——