7-carboxymethoxy-3-(4-hydroxyphenyl)-4H-chromen-4-one | 38588-56-6

• 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-carboxymethoxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
• 英文别名: 7-(O)-carboxymethyl daidzein；7-Carboxymethoxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one；7-O-carboxymethyl-daidzein；2-(3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yloxy)acetic acid；2-[3-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxyacetic acid
• CAS: 38588-56-6
• 化学式: C₁₇H₁₂O₆
• 分子量: 312.279
• InChiKey: YSEQWIWCJREEAV-UHFFFAOYSA-N

物化性质

• 熔点：
  244-245 °C
• 沸点：
  580.1±50.0 °C(Predicted)
• 密度：
  1.467±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  7-carboxymethoxy-3-(4-hydroxyphenyl)-4H-chromen-4-one 在 palladium on activated charcoal 氢气 作用下， 以47%的产率得到7-carboxymethoxy-3,4-dihydro-3-(4-hydroxyphenyl)-2H-chromene
  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：

  刺芒柄花素 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 72.0h， 生成 7-carboxymethoxy-3-(4-hydroxyphenyl)-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

• 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。
• ISOFLAVONE DERIVATIVES AND USES THEREOF
  申请人：Kohen Fortune

  公开号：US20100069478A1

  公开（公告）日：2010-03-18

  Isoflavone derivatives are provided comprising a carboxyalkylene moiety linked via its alkylene chain to the aromatic ring and via its carboxy group to an aminoalkyleneamino residue, which, in turn, is covalently linked to a functional group B. The isoflavone derivatives are preferably derived from biochanin A, genistein, and daidzein, and the functional group B is preferably an amino protecting group. These isoflavone derivatives are useful for treating or preventing diseases or disorders associated with estrogen receptor functioning.

  提供了一种异黄酮衍生物，其包括通过其烷基链连接到芳香环的羧基烷基部分，并通过其羧基连接到氨基烷基氨基残基，而该氨基烷基氨基残基则与功能基B共价连接。这些异黄酮衍生物优选自生物陈苯素A、异黄酮和大豆异黄酮，而功能基B优选为氨基保护基。这些异黄酮衍生物可用于治疗或预防与雌激素受体功能有关的疾病或疾病。
• Ground mixture
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0129893A2

  公开（公告）日：1985-01-02

  A ground mixture of a poorly soluble cystalline drug and an adsorbent is remarkably improved in the rates of dissolution and absorption of the drug.

  将溶解性较差的胱氨酸药物和吸附剂混合研磨后，可显著提高药物的溶解和吸收率。
• Derivatives of isoflavones
  申请人：Kohen Fortune

  公开号：US20050096381A1

  公开（公告）日：2005-05-05

  The present invention discloses novel derivatives of isoflavones, in particular carboxy derivatives of isoflavones, active as selective estrogen receptor modulators, and uses of the carboxy derivatives for the treatment of estrogen-related conditions. The present further discloses conjugates of these carboxy derivatives of isoflavones and their use for affinity targeting of drugs, imaging and detection agents to cells having estrogen receptors, particularly estrogen receptors subtype β.

  本发明公开了具有选择性雌激素受体调节剂活性的异黄酮的新型衍生物，特别是异黄酮的羧基衍生物，以及羧基衍生物在治疗雌激素相关疾病中的用途。本发明进一步公开了这些异黄酮羧基衍生物的共轭物，以及它们在药物、成像和检测剂与具有雌激素受体，特别是β亚型雌激素受体的细胞的亲和性靶向方面的用途。
• WO2008/102350
  申请人：——

  公开号：——

  公开（公告）日：——