7-acetoxy-3-(4-methoxyphenyl)-8-methyl-4H-chromen-4-one | 262600-96-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-acetoxy-3-(4-methoxyphenyl)-8-methyl-4H-chromen-4-one
• 英文别名: 7-Acetoxy-4'-methoxy-8-methylisoflavone；7-Acetoxy4'-methoxy-8-methylisoflavone；[3-(4-methoxyphenyl)-8-methyl-4-oxochromen-7-yl] acetate
• CAS: 262600-96-4
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: MYCGSQLQPUGWCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-acetoxy-3-(4-methoxyphenyl)-8-methyl-4H-chromen-4-one 在 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 32.0h， 生成 8-(2-carboxyethyl)-7-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of Haptens and Conjugates for ELISAs of Phytoestrogens. Development of the Immunological Tests

  摘要：

  Seven carboxylic acid haptens of isoflavonoids were synthesized, with the spacer arm on the oxygen atom at the C7 position for one series, with formononetin, daidzein, equol, biochanin A, and genistein, and at the C8 position for a second series, with only formononetin and daidzein. The different haptens were coupled to bovine serum albumin (BSA) and to swine thyroglobulin (Thyr). Polyclonal antibodies were generated against the BSA conjugates. Enzyme-linked immunosorbent assays (ELISAs) were developed based on competition between free phytoestrogens and the Thyr-hapten conjugates for specific antibodies. IC50 values of the standard curves ranged between 0.8 and 20 ng/mL that is, 0.3 and 9.2 pmol/well. The antibodies obtained should be useful for assays in vegetable matter as well as in biological fluids after a separation step. These ELISAs should be valuable also in the food industry to control phytoestrogen concentrations prior to and after processing.

  DOI：

  10.1021/jf990896v
• 作为产物：
  描述：

  1-(2,4-dihydroxy-3-methylphenyl)-2-(4-methoxyphenyl)ethanone 在 吡啶 、 三氟化硼乙醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 7-acetoxy-3-(4-methoxyphenyl)-8-methyl-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis of Haptens and Conjugates for ELISAs of Phytoestrogens. Development of the Immunological Tests

  摘要：

  Seven carboxylic acid haptens of isoflavonoids were synthesized, with the spacer arm on the oxygen atom at the C7 position for one series, with formononetin, daidzein, equol, biochanin A, and genistein, and at the C8 position for a second series, with only formononetin and daidzein. The different haptens were coupled to bovine serum albumin (BSA) and to swine thyroglobulin (Thyr). Polyclonal antibodies were generated against the BSA conjugates. Enzyme-linked immunosorbent assays (ELISAs) were developed based on competition between free phytoestrogens and the Thyr-hapten conjugates for specific antibodies. IC50 values of the standard curves ranged between 0.8 and 20 ng/mL that is, 0.3 and 9.2 pmol/well. The antibodies obtained should be useful for assays in vegetable matter as well as in biological fluids after a separation step. These ELISAs should be valuable also in the food industry to control phytoestrogen concentrations prior to and after processing.

  DOI：

  10.1021/jf990896v

文献信息

• Production of isoflavone derivatives
  申请人：Heaton Andrew

  公开号：US20050143588A1

  公开（公告）日：2005-06-30

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  描述了异黄酮氢化的方法，可以获得可操作数量的异黄烷-4-醇、异黄烯和异黄烷。在使用药用可接受的试剂和溶剂时，可以高纯度地获得异黄酮衍生物，并且产率接近定量。
• [EN] PRODUCTION OF ISOFLAVONE DERIVATIVES<br/>[FR] DERIVES D'ISOFLAVONE
  申请人：NOVOGEN RES PTY LTD

  公开号：WO2000049009A1

  公开（公告）日：2000-08-24

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  本文描述了一些对异黄酮进行氢化的方法，可以获得可用量的异黄酮-4-醇、异黄酮-3-烯和异黄酮。在使用药用可接受试剂和溶剂的同时，可以高纯度地获得异黄酮衍生物，并且接近定量收率。
• PRODUCTION OF ISOFLAVONE DERIVATIVES
  申请人：Novogen Research Pty. Ltd.

  公开号：EP1153020A1

  公开（公告）日：2001-11-14
• EP1153020A4
  申请人：——

  公开号：EP1153020A4

  公开（公告）日：2002-08-21
• US7906660B2
  申请人：——

  公开号：US7906660B2

  公开（公告）日：2011-03-15