trans-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-benzopyran-4-ol | 124093-19-2

• 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: trans-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-benzopyran-4-ol
• 英文别名: trans-4',7-dihydroxyisoflavan-4-ol；trans-tetrahydrodaidzein；(3R,4S)-tetrahydrodaidzein；(3R,4S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromene-4,7-diol
• CAS: 124093-19-2
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: YOSDNAMJVOLJKI-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 储存条件：
  室温、密封、干燥保存。

反应信息

• 作为产物：
  描述：

  大豆甙元 在 palladium on activated charcoal 锂硼氢 、 甲酸铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 29.0h， 生成 trans-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-benzopyran-4-ol
  参考文献：
  名称：

  The Synthesis, Structure, and Anticancer Activity of cis- and trans-4‘,7-Dihydroxyisoflavan-4-ols

  摘要：

  cis-4',7-Dihydroxyisoflavan-4-ol (4) and trans-4',7-dihydroxyisoflavan-4-ol (5), two proposed metabolites of daidzein (4',7-dihydroxyisoflavone), have been synthesized and fully characterized for the first time. The vicinal coupling constants of the pyran ring protons are compatible with a half-chair conformation. The cis isomer is anancomeric while the trans isomer consists of a 68:32 mixture of two ring inversion conformers. Molecular mechanical calculations are in agreement with the half-chair conformation of the pyran ring and suggest that the cis isomer is biased because of an unfavorable gauche interaction of the equatorial hydroxyl and the axial phenyl group. The isoflavanols 4 and 5 are comparable to genistein (4',5,7-trihydroxyisoflavone) in antitumor activity against human prostate cancer cells.

  DOI：

  10.1021/jo970892u

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。
• ENZYME ASSOCIATED WITH EQUOL SYNTHESIS
  申请人：Shimada Yoshikazu

  公开号：US20100330627A1

  公开（公告）日：2010-12-30

  An object of the present invention is to provide enzymes associated with equol synthesis, genes coding such enzymes, and a process for producing equol and its intermediates using the enzymes and genes. The present invention provides a dihydrodaidzein synthesizing enzyme, tetrahydrodaidzein synthesizing enzyme, equol synthesizing enzyme, and genes coding these enzymes. The present invention also provides a process for synthesizing dihydrodaidzein, tetrahydrodaidzein, and/or equol using these enzymes.

  本发明的目的是提供与大豆异黄酮代谢有关的酶、编码这些酶的基因以及利用这些酶和基因生产大豆异黄酮代谢产物的方法。本发明提供了一种合成二氢异黄酮的酶、四氢异黄酮合成酶、大豆异黄酮合成酶和编码这些酶的基因。本发明还提供了一种利用这些酶合成二氢异黄酮、四氢异黄酮和/或大豆异黄酮的方法。
• THERAPEUTIC METHODS AND COMPOSITIONS INVOLVING ISOFLAVONES
  申请人：KELLY Graham Edmund

  公开号：US20080287528A1

  公开（公告）日：2008-11-20

  Therapeutic methods of treatment, compositions and foodstuffs are described which contain isoflavone compounds described by general formula (1), in which Z is H, R 1 is H, or R A CO where R A is C 1-10 alkyl or an amino acid, R 2 is H, OH, or OR B where R B is an amino acid, or COR A where R A is as previously defined, W is H, A is H or OH, and B is selected from (a), (b), (c), or W is H, and A and B taken together form a six-membered ring selected from (d), or W, A and B taken with the groups with which they are associated comprise (e), or W and A taken together with the groups with which they are associated comprise (f) and B is (g) wherein R 3 is H, COR A where R A is as previously defined, CO 2 R C where R C is C 1-10 alkyl, or COR B where R B is as previously defined, R 4 is H, COR D where R D is H, OH, C 1-10 alkyl or an amino acid, CO 2 R C where R C is as previously defined, COR E where R E is H, C 1-10 alkyl or an amino acid, COOH, COR C where R C is as previously defined, or CONHR E where R E is as previously defined, R 5 is H, CO 2 R C where R C is as previously defined, or COR C OR E where R C and R E are as previously defined, and where the two R 5 groups are attached to the same group they are the same or different, R 6 is H or hydroxy C 1-10 alkyl, X is preferably O, but may be N or S, and Y is (h) where R 7 is H, or C 1-10 alkyl.

  本文描述了治疗方法、组合物和食品，其中包含一般式（1）所描述的异黄酮化合物，其中Z为H，R1为H或RACO，其中RA为C1-10烷基或氨基酸，R2为H、OH或ORB，其中RB为氨基酸，或CORA，其中RA如先前定义，W为H，A为H或OH，B选自（a）、（b）、（c），或W为H，A和B结合形成六元环，选自（d），或W、A和B与它们相关的基团组成（e），或W和A与它们相关的基团组成（f），B为（g），其中R3为H，CORA，其中RA如先前定义，CO2RC，其中RC为C1-10烷基，或CORB，其中RB如先前定义，R4为H，CORD，其中RD为H、OH、C1-10烷基或氨基酸，或CO2RC，其中RC如先前定义，CORE，其中RE为H、C1-10烷基或氨基酸，或COOH，CORC，其中RC如先前定义，或CONHRE，其中RE如先前定义，R5为H，CO2RC，其中RC如先前定义，或CORCORE，其中RC和RE如先前定义，且当两个R5基团连接到同一基团时，它们相同或不同，R6为H或羟基C1-10烷基，X优选为O，但也可以为N或S，Y为（h），其中R7为H或C1-10烷基。
• Waehaelae, K.; Hase, T. A., Heterocycles, 1989, vol. 28, # 1, p. 183 - 186
  作者：Waehaelae, K.、Hase, T. A.

  DOI：——

  日期：——
• Experimental and DFT ¹H NMR Study of Conformational Equilibria in <i>trans</i>-4‘,7-Dihydroxyisoflavan-4-ol and <i>trans</i>-Isoflavan-4-ol
  作者：Kalevi Pihlaja、Petri Tähtinen、Karel D. Klika、Tuija Jokela、Auli Salakka、Kristiina Wähälä

  DOI：10.1021/jo0301200

  日期：2003.9.1

  The solution-state conformational equilibria of trans-4',7-dihydroxyisoflavan-4-ol (1) and trans-isoflavan-4-ol (2) were assessed based on the temperature dependence of their vicinal coupling constants J(H-2alpha,H-3) and J(H-3,H-4) in comparison to values calculated with density functional theory (DFT) methods at the B3LYP/cc-pVTZ//B3LYP/6-31G(d,p) level of theory. For each half-chair conformer, several rotamers with respect to the C-4 hydroxyl and C-3 phenyl were calculated and the overall diequatorial-to-diaxial ratio at 298 K was assessed as 66:34 for 1 and 73:27 for 2. The syntheses of 1 and 2 are described.