二氢染料木碱 | 21554-71-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 中文名称: 二氢染料木碱
• 中文别名: 4H-1-苯并吡喃-4-酮,2,3-二氢-5,7-二羟基-3-(4-羟基苯基)-
• 英文名称: dihydrogenistein
• 英文别名: 5,7-dihydroxy-3-(4-hydroxyphenyl)chroman-4-one；4',5,7-trihydroxyisoflavan-4-one；4',5,7-trihydroxyisoflavanone；4',5,7-Trihydroxyisoflavone；2,3-dihydroisoflavanone；5,7-dihydroxy-3-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 21554-71-2
• 化学式: C₁₅H₁₂O₅
• 分子量: 272.257
• InChiKey: UQGVUYNHDKMLSE-UHFFFAOYSA-N

物化性质

• 沸点：
  577.9±50.0 °C(Predicted)
• 密度：
  1.485±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于乙酸乙酯（少许）、甲醇（少许）
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

ADMET

代谢

二氢异黄酮已知的人类代谢物包括2-(4-羟基苯基)-1-(2,4,6-三羟基苯基)丙-2-烯-1-酮。

Dihydrogenistein has known human metabolites that include 2-(4-Hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  二氢染料木碱 在 吡啶 、 氯磺酸 作用下， 反应 14.0h， 以80%的产率得到2,3-dihydro-5-hydroxy-7-sulfooxy-3-(4-sulfooxyphenyl)-4H-1-benzopyran-4-one disodium salt
  参考文献：
  名称：

  Synthesis of phytoestrogenic isoflavonoid disulfates

  摘要：

  Di-O-sulfates of six phytoestrogenic isoflavonoids, daidzein (1), genistein (2), glycitein (3), and the reduced metabolites dihydrodaidzein (4), dihydrogenistein (5) and equol (6) were synthesized. These compounds are known or potential inhibitors of steroid sulfatase enzymes. The new compounds were characterized by NMR and mass spectrometry. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.03.015
• 作为产物：
  描述：

  染料木素 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以13.2 mg的产率得到二氢染料木碱
  参考文献：
  名称：

  Swartzia polyphylla心材中的异黄酮及其对龋齿细菌的抗菌活性。

  摘要：

  Swartzia polyphylla DC的甲醇提取物。心材具有抗龋齿变形链球菌的活性。提取物进行色谱纯化，得到七个类黄酮。其中，三种已知的异黄酮，二氢生物chanin A，铁瑞林和darbergioidin，以及一种新的异黄烷酮5,2'，4'-三羟基-7-甲氧基异黄烷酮（二氢卡雅宁）对龋齿细菌具有有效的抗菌活性。在异黄酮衍生物上未检测到该作用。进一步进行了各种类黄酮的比较抗菌研究，并讨论了它们的构效关系。

  DOI：

  10.1248/cpb.40.2970
• 作为试剂：
  描述：

  、 染料木素 、 甲酸铵 在 二氢染料木碱 、 氮气 、 甲醇 、 钯 、 chloroform methanol 作用下， 以to afford crude 22的产率得到二氢染料木碱
  参考文献：
  名称：

  INHIBITION AND TREATMENT OF PROSTATE CANCER METASTASIS

  摘要：

  本发明提供了抑制和治疗转移性前列腺癌的化合物和方法。这些化合物包括MEK4抑制剂。另一方面，本发明提供了通过筛选MEK4抑制剂来鉴定转移性前列腺癌抑制剂的方法。

  公开号：

  US20100137425A1

文献信息

• Dietary Phytoestrogens and Their Synthetic Structural Analogues as Calcium Channel Blockers in Human Platelets
  作者：Yuliya Dobrydneva、Roy L. Williams、Gary Z. Morris、Peter F. Blackmore

  DOI：10.1097/00005344-200209000-00009

  日期：2002.9

  Phytoestrogens have been shown to inhibit platelet activation by blocking platelet calcium channels. This study examined the effect of several synthetic derivatives of trans-resveratrol, genistein, and daidzein on plateletfree intracellular calcium ([Ca2+]i) elevation in thrombin-activated platelets and the possible mechanisms of this inhibitory effect. Studies were conducted on fresh human platelets from healthy volunteers. The fluorescent dye fura-2 was used to monitor [Ca2+]i in platelets. At 10 μM trans-resveratrol, triacetyl-trans-resveratrol, and trimethoxy-trans-resveratrol produced, respectively, 57 ± 4%, 40 ± 4%, and 21 ± 1% inhibition; genistein, acetylgenistein, and dihydrogenistein produced 51 ± 10%, 26 ± 7%, and 16 ± 2% inhibition, respectively; daidzein and diacetyldaidzein produced 56 ± 5% and 45 ± 10% inhibition of thrombin-induced [Ca2+]i elevation. The inhibitory effect was immediate and appeared to directly affect the calcium influx channels. Phytoestrogen action on [Ca2+]i did not cause alteration in nitric oxide signaling. Tyrosine phosphorylation was not involved in the inhibition of [Ca2+]i elevation by phytoestrogens, because the percent inhibition produced by the tyrosine kinase inhibitor genistein and its inactive analogue daidzein on thrombin-induced and thapsigargin-induced [Ca2+]i elevation was not significantly different for either compound at any concentration tested. Structure–activity relationship studies on this limited set of compounds reveal the requirements for the stilbene pharmacophore for the calcium-blocking activity.

  植物雌激素可通过阻断血小板钙通道抑制血小板活化。本研究考察了几种反式白藜芦醇、染料木素和大豆异黄酮的合成衍生物对凝血酶激活的血小板游离细胞内钙（[Ca2+]i）升高的影响以及这种抑制作用的可能机制。研究以健康志愿者的新鲜人体血小板为对象。使用荧光染料 fura-2 监测血小板中的[Ca2+]i。在 10 μM 的反式-白藜芦醇、三乙酰基-反式-白藜芦醇和三甲氧基-反式-白藜芦醇浓度下，分别产生 57 ± 4%、40 ± 4% 和 21 ± 1% 的抑制作用；染料木素、乙酰染料木素和二氢染料木素分别产生 51 ± 10%、26 ± 7% 和 16 ± 2% 的抑制作用；大豆雌酚和二乙酰大豆雌酚分别产生 56 ± 5% 和 45 ± 10% 的凝血酶诱导的 [Ca2+]i 升高抑制作用。抑制作用是即时的，似乎直接影响了钙离子通道。植物雌激素对[Ca2+]i 的作用不会导致一氧化氮信号的改变。酪氨酸磷酸化不参与植物雌激素对[Ca2+]i 升高的抑制作用，因为酪氨酸激酶抑制剂染料木素和其非活性类似物染料木素对凝血酶诱导的[Ca2+]i 升高和硫辛酸诱导的[Ca2+]i 升高的抑制百分比在任何测试浓度下都没有显著差异。对这组有限化合物进行的结构-活性关系研究揭示了钙阻断活性对芪类药物结构的要求。
• Nadph: Biochanin a oxidoreductase from the fungus Fusarium javanicum
  作者：Dittmar Schlieper、Wolfgang Barz

  DOI：10.1016/s0031-9422(00)83862-5

  日期：——

  Abstract A soluble enzyme which catalyses the NADPH-dependent reduction of the heterocyclic double bond of the isoflavone biochanin A (5,7-dihydroxy-4′-methoxy-isoflavone) yielding the corresponding isoflavanone was isolated from the fungus Fusarium javanicum. The NADPH: biochanin A oxidoreductase was constitutively present in the mycelium with an extractable average activity of 4 pkat/g fresh weight. The

  摘要 从真菌 Fusarium javanicum 中分离出一种可溶性酶，该酶催化异黄酮生物链素 A（5,7-二羟基-4'-甲氧基-异黄酮）的杂环双键的 NADPH 依赖性还原，产生相应的异黄烷酮。NADPH: biochanin A 氧化还原酶组成型存在于菌丝体中，可提取的平均活性为 4 pkat/g 鲜重。将酶纯化约 4500 倍至表观均一。天然酶的 Mr, 约为 87 000，由 Mr, 43 000 的两个相同亚基组成。酶反应显示最佳 pH 值为 7.5，最佳温度为 30 至 35°。biochanin A 的表观 Km 值为 43 μM，NADPH 的表观 Km 值为 190 μM，最大速度为 4 mkat/kg 蛋白质。该酶对 biochanin A 表现出显着的底物特异性。
• BIOCOMPATIBLE AND BIODEGRADABLE POLYMERS FROM RENEWABLE NATURAL POLYPHENOLS
  申请人：Dasgupta Falguni

  公开号：US20120184682A1

  公开（公告）日：2012-07-19

  This invention describes the use of resveratrol and curcumin, representatives of naturally occurring polyphenols, in their native form, after hydrogenation, and as their respective allyl derivatives, individually, in combination with themselves and other commercial monomers, to make representative varieties of polymers, e.g., polycarbonates (PC), polyurethanes (PU), co-polymers and biodegradable polymers.

  本发明描述了白藜芦醇和姜黄素的使用，它们是天然存在的多酚类代表，以它们的原始形式、氢化后形式和它们各自的丙烯基衍生物形式，单独地、与它们自己和其他商业单体的组合，制造代表性的聚合物品种，例如聚碳酸酯（PC）、聚氨酯（PU）、共聚物和生物可降解聚合物。
• Therapeutic methods and compositions involving isoflavones
  申请人：Novogen Research PTY Limited

  公开号：US20030018060A1

  公开（公告）日：2003-01-23

  Therapeutic methods of treatment, compositions and foodstuffs are described which contain isoflavone compounds described by general formula (I), 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 aIkyl, X is preferably O, but may be N or S, and Y is (h) where R 7 is H, or C 1-10 alky).

  本文描述了一种治疗方法、组合物和食品，其中包含了一般式（I）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如上定义，W为H，A为H或OH，B选自（a）、（b）、（c），或W为H，A和B共同形成六元环，选自（d），或W、A和B与它们相关联的基团共同形成（e），或W和A与它们相关联的基团共同形成（f），B为（g），其中R3为H，或CORA，其中RA如上定义，CO2RC，其中RC为C1-10烷基，或CORB，其中RB如上定义，R4为H，CORD，其中RD为H、OH、C1-10烷基或氨基酸，或CO2RC，其中RC如上定义，CORE，其中RE为H、C1-10烷基或氨基酸，COOH，CORC，其中RC如上定义，或CONHRE，其中RE如上定义，R5为H，CO2RC，其中RC如上定义，或CORCORE，其中RC和RE如上定义，如果两个R5基团连接到同一基团，则它们相同或不同，R6为H或羟基C1-10烷基，X最好为O，但也可以为N或S，Y为（h），其中R7为H或C1-10烷基。
• 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。