4'-O-carboxymethyl-daidzein | 188990-70-7

• 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: 4'-O-carboxymethyl-daidzein
• 英文别名: [4-(7-Hydroxy-4-oxo-4H-1-benzopyran-3-yl)phenoxy]acetic acid；2-[4-(7-hydroxy-4-oxochromen-3-yl)phenoxy]acetic acid
• CAS: 188990-70-7
• 化学式: C₁₇H₁₂O₆
• 分子量: 312.279
• InChiKey: AGNHIVZTXBSASB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  大豆甙元 在 potassium tert-butylate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 4'-O-carboxymethyl-daidzein
  参考文献：
  名称：

  Time-resolved fluoroimmunoassay of plasma daidzein and genistein11Abbreviations: Daidzein (Da), genistein (Gen), gas-liquid chromatography (GC), high performance liquid chromatography (HPLC), mass spectrometry (MS), radioimmunoassay (RIA), time-resolved fluoroimmunoassay (TR-FIA), enzymeimmunoassay (EIA), fluoroimmunoassay (FIA), bovine serum albumin (BSA), N,N′-dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (NHS), isotope dilution gas chromatography-mass spectrometry in the selected ion monitoring mode (ID-GC-MS-SIM), coefficients of variation (CVs). B = Binding of tracer to antibody in the presence of unlabeled analyte. B0 = Binding of tracer to antibody in the absence of unlabeled analyte. T = Total amount of tracer added. Estradiol = estradiol-17β.

  摘要：

  We present a method for the determination of the phytoestrogens daidzein and genistein in plasma (serum). These weakly estrogenic isoflavones occur in soybeans and in smaller amounts in some other beans and plants. It has been suggested that they may afford protection against prostate and breast cancer. The method is based on time-resolved fluoroimmunoassay (TR-FIA) using a europium chelate as a label. After synthesis of 4'-O-carboxymethyl-daidzein and 4'-O-carboxymethyl-genistein the compounds are coupled to bovine serum albumin (BSA), then used as antigens to immunize rabbits. The tracers with the europium chelate are synthesized using the same 4'-O-derivative of the isoflavones. After enzymatic hydrolysis and ether extraction the immunoassay is carried out using the VICTOR 1420 multilabel counter (Wallac Oy, Turku, Finland). The antisera cross-reacted to some extent with some isoflavonoids but not with flavonoids. The cross-reactivity seems not to influence the results, which were highly specific for both compounds. The correlation coefficients between the TR-FIA methods and the reference method based on isotope dilution gas chromatography-mass spectrometry were high; r-values were about 0.95-0.99 depending on concentration. The intra-assay coefficients of variation (CV%) for daidzein and genistein at three different concentrations vary 3.2-4.5 and 3.2-4.1, respectively. The inter-assay CVs vary 5.0-6.3 and 4.5-5.3, respectively. The working ranges of the daidzein and genistein assays are 1.0-216 and 1.7-370 nmol/l, respectively. The plasma values (n = 80) of daidzein and genistein are very low in Finnish subjects (mean for daidzein, 3.8 +/- 6.8 and for genistein, 3.2 +/- 7.6 nmol/l; median value for daidzein 1.5 and for genistein 1.4 nmol/l). (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00089-1

文献信息

• 一种黄豆苷元半抗原和完全抗原及其制备方法和应用
  申请人：华南农业大学

  公开号：CN105669628A

  公开（公告）日：2016-06-15

  本发明公开了一种黄豆苷元半抗原和完全抗原及其制备方法和应用。所述黄豆苷元半抗原的分子结构如下式（Ⅰ）或式（Ⅱ）所示：本发明以黄豆苷元为原料，经过2步化学反应分别得到黄豆苷元7-衍生物和4`-衍生物半抗原，成功地合成了黄豆苷元半抗原，合成方法安全有效，产物纯度高。在此基础上进一步采用活泼酯法制备适合于动物免疫的黄豆苷元完全抗原，以此抗原免疫Balb/c小鼠，效价可达1：32000，抑制率可达94.9%，为建立黄豆苷元的免疫分析方法提供了核心原材料和有利条件，具有广阔的实际应用前景。
• Time-resolved fluoroimmunoassay of plasma daidzein and genistein11Abbreviations: Daidzein (Da), genistein (Gen), gas-liquid chromatography (GC), high performance liquid chromatography (HPLC), mass spectrometry (MS), radioimmunoassay (RIA), time-resolved fluoroimmunoassay (TR-FIA), enzymeimmunoassay (EIA), fluoroimmunoassay (FIA), bovine serum albumin (BSA), N,N′-dicyclohexylcarbodiimide (DCC), N-hydroxysuccinimide (NHS), isotope dilution gas chromatography-mass spectrometry in the selected ion monitoring mode (ID-GC-MS-SIM), coefficients of variation (CVs). B = Binding of tracer to antibody in the presence of unlabeled analyte. B0 = Binding of tracer to antibody in the absence of unlabeled analyte. T = Total amount of tracer added. Estradiol = estradiol-17β.
  作者：Guojie J Wang、Oldrich Lapcı́k、Richard Hampl、Mariko Uehara、Nawaf Al–Maharik、Katariina Stumpf、Heikki Mikola、Kristiina Wähälä、Herman Adlercreutz

  DOI：10.1016/s0039-128x(00)00089-1

  日期：2000.6

  We present a method for the determination of the phytoestrogens daidzein and genistein in plasma (serum). These weakly estrogenic isoflavones occur in soybeans and in smaller amounts in some other beans and plants. It has been suggested that they may afford protection against prostate and breast cancer. The method is based on time-resolved fluoroimmunoassay (TR-FIA) using a europium chelate as a label. After synthesis of 4'-O-carboxymethyl-daidzein and 4'-O-carboxymethyl-genistein the compounds are coupled to bovine serum albumin (BSA), then used as antigens to immunize rabbits. The tracers with the europium chelate are synthesized using the same 4'-O-derivative of the isoflavones. After enzymatic hydrolysis and ether extraction the immunoassay is carried out using the VICTOR 1420 multilabel counter (Wallac Oy, Turku, Finland). The antisera cross-reacted to some extent with some isoflavonoids but not with flavonoids. The cross-reactivity seems not to influence the results, which were highly specific for both compounds. The correlation coefficients between the TR-FIA methods and the reference method based on isotope dilution gas chromatography-mass spectrometry were high; r-values were about 0.95-0.99 depending on concentration. The intra-assay coefficients of variation (CV%) for daidzein and genistein at three different concentrations vary 3.2-4.5 and 3.2-4.1, respectively. The inter-assay CVs vary 5.0-6.3 and 4.5-5.3, respectively. The working ranges of the daidzein and genistein assays are 1.0-216 and 1.7-370 nmol/l, respectively. The plasma values (n = 80) of daidzein and genistein are very low in Finnish subjects (mean for daidzein, 3.8 +/- 6.8 and for genistein, 3.2 +/- 7.6 nmol/l; median value for daidzein 1.5 and for genistein 1.4 nmol/l). (C) 2000 Elsevier Science Inc. All rights reserved.