2'-羟基金雀异黄素 | 1156-78-1

• 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 - 异黄酮类化合物
• 中文名称: 2'-羟基金雀异黄素
• 中文别名: 2',4',5,7-四羟基异黄酮
• 英文名称: 2',4',5,7-tetrahydroxyisoflavone
• 英文别名: 2'-Hydroxygenistein；2′-hydroxygenistein；5,7,2',4'-tetrahydroxyisoflavone；2',4',5,7-Tetrahydroxy-isoflavon；2’-hydroxygenistein；3-(2,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
• CAS: 1156-78-1
• 化学式: C₁₅H₁₀O₆
• mdl: MFCD00075967
• 分子量: 286.241
• InChiKey: GSSOWCUOWLMMRJ-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 物理描述：
  Solid
• 熔点：
  270-273°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2914501900

反应信息

• 作为反应物：
  描述：

  2'-羟基金雀异黄素 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以66%的产率得到1,3,8-三羟基-11H-苯并呋喃并[2,3-b][1]苯并吡喃-11-酮
  参考文献：
  名称：

  Total synthesis of the pyranocoumaronochromone lupinalbin H

  摘要：

  The pyranocoumaronochromone lupinalbin H was synthesized in three major steps, which involved preparation of 2'-hydroxygenistein by the Suzuki-Miyaura reaction, followed by oxidative cyclodehydrogenation into lupinalbin A. The final step was the regiospecific introduction of the dimethylpyran moiety to ring A of lupinalbin A via an aldol-type condensation with 3-methyl-2-butenal and 6 pi-electrocyclization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.042
• 作为产物：
  描述：

  1,3-双(甲氧基甲氧基)苯 在 盐酸 、 正丁基锂 、 palladium 10% on activated carbon 、 水 、 碘 、 silver(I) acetate 、 sodium carbonate 、 氯化铵 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 正己烷 、 氯仿 、 水 为溶剂， 反应 19.0h， 生成 2'-羟基金雀异黄素
  参考文献：
  名称：

  Total synthesis of the pyranocoumaronochromone lupinalbin H

  摘要：

  The pyranocoumaronochromone lupinalbin H was synthesized in three major steps, which involved preparation of 2'-hydroxygenistein by the Suzuki-Miyaura reaction, followed by oxidative cyclodehydrogenation into lupinalbin A. The final step was the regiospecific introduction of the dimethylpyran moiety to ring A of lupinalbin A via an aldol-type condensation with 3-methyl-2-butenal and 6 pi-electrocyclization. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.09.042

文献信息

• Total synthesis of apios isoflavones and investigation of their tyrosinase inhibitory activity
  作者：Nana Asebi、Ken-ichi Nihei

  DOI：10.1016/j.tet.2019.130589

  日期：2019.10

  key steps. In addition, aglycones 4 and 5 and related natural isoflavone cajanin (6) were synthesized in short steps. Evaluation of the inhibitory activity of these compounds toward tyrosinase indicated that all the compounds were active. In particular, the half-maximal inhibitory concentration of compound 1 toward tyrosinase was measured to be 729 μM.

  通过Friedel-Crafts反应，Bischler-Napieralski型环化和相转移催化糖基化作为关键步骤，首次合成了Apios异黄酮葡萄糖苷1和2。此外，糖苷元4和5以及相关的天然异黄酮木豆素（6）可以在短时间内合成。这些化合物对酪氨酸酶的抑制活性的评估表明所有化合物都是有活性的。特别地，测得化合物1对酪氨酸酶的最大抑制浓度的一半为729μM。
• METHOD OF BIOTRANSFORMATION OF BENZOPYRONE COMPOUNDS INTO THE CORRESPONDING PHOSPHATE-CONJUGATED DERIVATIVES
  申请人：National Taiwan University

  公开号：US20170305944A1

  公开（公告）日：2017-10-26

  The present invention is related to a biotransformation process, effected by means of an isolated polypeptide possessing benzopyrone phosphate synthetase activity, and also a microorganism comprising a nucleic acid sequence that encodes the polypeptide, for the preparation of phosphate-conjugated derivatives of benzopyrone compounds. The hydrophilic property of the benzopyrone compounds is enhanced after catalyzed by the benzopyrone phosphate synthetase of the present invention.

  本发明涉及一种生物转化过程，通过一种具有苯并吡喃磷酸合酶活性的分离多肽实现，并且包括一种编码该多肽的核酸序列的微生物，用于制备苯并吡喃化合物的磷酸共轭衍生物。经本发明的苯并吡喃磷酸合酶催化后，苯并吡喃化合物的亲水性质得到增强。
• Molecular Characterization and Phylogenetic Analysis of Two Novel Regio-specific Flavonoid Prenyltransferases from Morus alba and Cudrania tricuspidata
  作者：Ruishan Wang、Ridao Chen、Jianhua Li、Xiao Liu、Kebo Xie、Dawei Chen、Yunze Yin、Xiaoyu Tao、Dan Xie、Jianhua Zou、Lin Yang、Jungui Dai

  DOI：10.1074/jbc.m114.608265

  日期：2014.12

  distributed in several plant families. The prenylation catalyzed by prenyltransferases represents a Friedel-Crafts alkylation of the flavonoid skeleton in the biosynthesis of natural prenylated flavonoids and contributes to the structural diversity and biological activities of these compounds. To date, all identified plant flavonoid prenyltransferases (FPTs) have been identified in Leguminosae. In the

  异戊二烯化黄酮是有吸引力的特殊代谢物，具有广泛的生物活性，分布在几个植物科中。异戊二烯基转移酶催化的异戊二烯化代表了天然异戊二烯化黄酮类化合物生物合成中类黄酮骨架的 Friedel-Crafts 烷基化，有助于这些化合物的结构多样性和生物活性。迄今为止，所有已鉴定的植物类黄酮异戊二烯基转移酶 (FPT) 都已在豆科植物中得到鉴定。在本研究中，分别从桑科植物 M. alba 和 C. tricuspidata 中鉴定了两种新的 FPT，即桑树异甘草素 3'-二甲基烯丙基转移酶 (MaIDT) 和柘木异甘草素 3'-二甲基烯丙基转移酶 (CtIDT)。MaIDT 和 CtIDT 与豆科 FPT 具有低水平的同源性。MaIDT 和 CtIDT 被预测为膜结合蛋白，具有预测的转运肽、七个跨膜区域和与其他异戊二烯酸转移酶相似的保守功能域。重组 MaIDT 和 CtIDT 能够区域选择性地将二甲基烯丙
• Synthesis of Licoisoflavone A and Related Compounds
  作者：Masao Tsukayama、Kunihiro Fujimoto、Tokunaru Horie、Mitsuo Masumura、Mitsuru Nakayama

  DOI：10.1246/bcsj.58.136

  日期：1985.1

  2′,4′,5,7-Tetrahydroxyisoflavone was partially benzoylated with benzoyl chloride to give 7-benzoyloxy-2′, 4′,5-trihydroxyisoflavone. The condensation of the 7-(benzoyloxy)isoflavone with 2-methyl-3-buten-2-ol, followed by the hydrolysis of the resultant 3′-(3-methyl-2-butenyl)isoflavone gave licoisoflavone A. Its 5′-(3-methyl-2-butenyl) isomer was also synthesized from 5-benzoyloxy-2′,4′,7-trihydroxyisoflavone in a similar manner.

  用苯甲酰氯对 2′，4′，5，7-四羟基异黄酮进行部分苯甲酰化，得到 7-苯甲酰氧基-2′，4′，5-三羟基异黄酮。将 7-（苯甲酰氧基）异黄酮与 2-甲基-3-丁烯-2-醇缩合，然后水解生成 3′-（3-甲基-2-丁烯基）异黄酮，就得到了地衣异黄酮 A。它的 5′-（3-甲基-2-丁烯基）异构体也是用类似的方法从 5-苯甲酰氧基-2′,4′,7-三羟基异黄酮合成的。
• SYNTHESES OF LICOISOFLAVONE A AND 5′-ALKENYL ISOMER
  作者：Masao Tsukayama、Kunihiro Fujimoto、Tokunaru Horie、Yoshiro Yamashita、Mitsuo Masumura、Mitsuru Nakayama

  DOI：10.1246/cl.1982.675

  日期：1982.5.5

  2′,4′,5,7-Tetrahydroxyisoflavone was partially benzoylated with benzoyl chloride to give 7-benzoyloxy-2′,4′,5-trihydroxyisoflavone. The condensation of 7-benzoyloxyisoflavone with 2-methyl-3-buten-2-ol, followed by the hydrolysis of the resultant 3′-(3-methyl-2-butenyl)isoflavone afforded licoisoflavone A. Its 5′-(3-methyl-2-butenyl) isomer was also synthesized from 5-benzoyloxyisoflavone.

  用苯甲酰氯对 2′，4′，5，7-四羟基异黄酮进行部分苯甲酰化，得到 7-苯甲酰氧基-2′，4′，5-三羟基异黄酮。将 7-苯甲酰氧基异黄酮与 2-甲基-3-丁烯-2-醇缩合，然后水解生成 3′-（3-甲基-2-丁烯基）异黄酮，得到地衣异黄酮 A。