(3R)-7,2'-二羟基-3',4'-二甲氧基异黄烷 | 64474-51-7

• 物质功能分类: 有机原料 - 杂环化合物
• 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: (3R)-7,2'-二羟基-3',4'-二甲氧基异黄烷
• 中文别名: 7,2'-二羟基-3',4'-二甲氧基异黄烷
• 英文名称: isomucronulatol
• 英文别名: (-)-(3R)-isomucronulatol；(3R)-7,2'-dihydroxy-3',4'-dimethoxyisoflavan；(R)-Isomucronulatol；(3R)-3-(2-hydroxy-3,4-dimethoxyphenyl)-3,4-dihydro-2H-chromen-7-ol
• CAS: 64474-51-7
• 化学式: C₁₇H₁₈O₅
• 分子量: 302.327
• InChiKey: NQRBAPDEZYMKFL-NSHDSACASA-N

物化性质

• 熔点：
  152-153℃ (chloroform )
• 沸点：
  426.8±45.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099
• 储存条件：
  存于2-8℃环境中，应避光、干燥并密封保存。

制备方法与用途

(R)-异muecronulatol是一种天然的类黄酮，可以从盐生球藻的种子中提取获得。

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (3R)-7,2'-二羟基-3',4'-二甲氧基异黄烷 以 乙醚 为溶剂， 反应 1.0h， 以2 mg的产率得到7-0-methylisomucronulatol
  参考文献：
  名称：

  来自蒙古黄芪的异黄酮和翼果

  摘要：

  摘要 三种新的异黄烷，7-O-甲基异鼠尾醇，异鼠尾醇 7,2'-二-O-葡萄糖苷，5'-羟基异鼠尾醇 2',5'-二-O-葡萄糖苷，和一种新的紫檀醇，3,9-二- O-methylnissolin 是从黄芪根中分离出来的。它们的结构是通过光谱分析和化学转化确定的。

  DOI：

  10.1016/0031-9422(91)85143-n
• 作为产物：
  描述：

  刺芒柄花素 在 Colutea arborescens 作用下， 反应 672.0h， 生成 (3R)-7,2'-二羟基-3',4'-二甲氧基异黄烷
  参考文献：
  名称：

  异黄烷异木糖醇的生物合成：2',3',4'-氧化模式的起源

  摘要：

  摘要 用 14 C-标记的异黄酮喂养番泻叶 (Colutea arborescens) 的幼苗和豆荚的实验表明，7-羟基-4'-甲氧基异黄酮 (formononetin)、7,3'-二羟基-4'-甲氧基异黄酮 (花萼)、 7,2',3'-三羟基-4'-甲氧基异黄酮 (koparin) 和 7,2'-二羟基-3',4'-二甲氧基异黄酮是 (3 R )-isomucronulatol (7,2'-dihydroxy- 3',4'-二甲氧基异黄烷）。然而，7,2'-二羟基-4'-甲氧基异黄酮（2'-羟基甲氧基异黄酮）和7-羟基-3',4'-二甲氧基异黄酮（cladrin）是较差的底物。因此，从芒柄花素到异木糖醇的生物合成顺序包括 3'-羟基化、2'-羟基化和 3'-O-甲基化，然后大概是 7,2'-二羟基-3',4'-二甲氧基异黄酮的立体定向还原。处理 2',3',

  DOI：

  10.1016/s0031-9422(00)80806-7

文献信息

• Inhibitors of Prostaglandin Biosynthesis from Dalbergia odorifera.
  作者：Yukihiro GODA、Fumiyuki KIUCHI、Masaaki SHIBUYA、Ushio SANKAWA

  DOI：10.1248/cpb.40.2452

  日期：——

  (+)-isoduartin (isoflavan), odoriflavene (isoflav-3-ene) and (-)-odoricarpan (pterocarpan) were isolated and their structures were elucidated on the basis of chemical and spectroscopic methods. Of the fifteen compounds isolated, cinnamylphenols, isoflavans, isoflavene and benzoic acid derivative significantly inhibited prostaglandin biosynthesis as well as platelet aggregation induced by arachidonic acid.

  Dalbergia odorifera T. Chen（Leguminosae）的根心材是一种用于停滞血液综合症（血液停滞；日语，oketsu）的中药（日语名称koshinko）。除10种已知化合物外，还分离了五种新的酚类化合物，异丁烯基苯乙烯和羟基邻苯二酚（肉桂基酚），（+）-异都丁（isoflavan），奥多弗拉芬（isoflav-3-ene）和（-）-奥多氯潘（罗汉果）。在化学和光谱学方法的基础上进行了阐明。在分离的15种化合物中，肉桂基酚，异黄烷酮，异黄酮和苯甲酸衍生物显着抑制前列腺素的生物合成以及花生四烯酸诱导的血小板凝集。
• A pterocarpan and two isoflavans from alfalfa
  作者：Gayland F. Spencer、Barry E. Jones、Ronald D. Plattner、David E. Barnekow、Linda S. Brinen、Jon Clardy

  DOI：10.1016/0031-9422(91)83483-2

  日期：1991.1

  (7-hydroxy-2′,3′,4′-trimethoxyisoflavan) and (+)-(2,3,4-trimethoxy-5-hydroxyphenyl)-2,3-dihydro-7-hydroxy-4 H -1-benzopyran (7,5′-dihydroxy-2′,3′,4′-trimethoxyisoflavan) were isolated for the first time from dried Medicago sativa hay. Structural assignments were based on 1 H NMR and mass spectra, X-ray crystallography, and optical rotations.

  摘要 (-)6 aR ,11 aR -Dihydro-3-hydroxy-9,10-dimethoxy-6 H -benzofuro[3,2 c ] [1]-benzopyran (10-methoxymedicarpin), (+)-(2, 3,4,-三甲氧基苯基)-2,3-二氢-7-羟基-4H-1-苯并吡喃(7-羟基-2',3',4'-三甲氧基异黄烷)和(+)-(2,3, 4-三甲氧基-5-羟基苯基)-2,3-二氢-7-羟基-4 H -1-苯并吡喃(7,5'-dihydroxy-2',3',4'-trimethoxyisoflavan)首次被分离来自干燥的苜蓿干草。结构分配基于 1 H NMR 和质谱、X 射线晶体学和旋光度。
• Nitric oxide inhibitory flavonoids from traditional Chinese medicine formula Baoyuan Decoction
  作者：Xiaoli Ma、Qian Yu、Xiaoyu Guo、Kewu Zeng、Mingbo Zhao、Pengfei Tu、Yong Jiang

  DOI：10.1016/j.fitote.2015.04.011

  日期：2015.6

  Three new flavonoid glycosides, (3R)-(+)-isomucronulatol-2'-O-beta-D-glucopyranoside (I), (3R)-(-)-isomucronulatol-7-O-beta-D-apiofuranosyl(1 --> 2)-beta-D-glucopyranoside (2), and (2S)-(-)-7,8-dihydroxylflavanone-4'-O-beta-D-apiofuranosyl(1 --> 2)-beta-D-glucopyranoside (3), along with eight flavanones (4, 8, 10, 12, 15, 16, 21, and 24), four isoflavones (5, 11, 13, and 23), four chalcones (6, 14, 17, and 18), two isoflavans (19-20), one flavone (7), one flavonol (9), and one dihydrochalcone (22) were isolated from Baoyuan Decoction (BYD), a traditional Chinese medicine formula. The structures of the new compounds were established by detailed analysis of NMR and HRESIMS spectroscopic data, and their absolute configurations were determined by electronic circular dichroism (ECD) data. The inhibitory effects of the isolates were evaluated on nitric oxide production in lipopolysaccharide activated RAW 264.7 macrophage cells. Compounds 6, 9, and 10 showed the significant inhibitory activities, with IC50 values of 1.4, 13.8, and 9.3 mu M, respectively, comparable to or even better than the positive control, quercetin (IC50, 16.5 mu M). The assignment of these isolated flavonoids was achieved using UPLC-Q-trap-MS, and the results suggested that they were originated from Astragalus membranaceus and Glycyrrhiza uralensis. (C) 2015 Elsevier B.V. All rights reserved.
• Biosynthesis of the isoflavan isomucronulatol: Origin of the 2′,3′,4′-oxygenation pattern
  作者：Hakim A.M. Al-Ani、Paul M. Dewick

  DOI：10.1016/s0031-9422(00)80806-7

  日期：1985.1

  arborescens ) have demonstrated that 7-hydroxy-4′-methoxyisoflavone (formononetin), 7,3′-dihydroxy-4′-methoxyisoflavone (calycosin), 7,2′,3′-trihydroxy-4′-methoxyisoflavone (koparin) and 7,2′-dihydroxy-3′,4′-dimethoxyisoflavone are excellent precursors of (3 R )-isomucronulatol (7,2′-dihydroxy-3′,4′-dimethoxyisoflavan). 7,2′-Dihydroxy- 4′-methoxyisoflavone (2′-hydroxyformononetin) and 7-hydroxy-3′,4′-dimethoxyisoflavone

  摘要 用 14 C-标记的异黄酮喂养番泻叶 (Colutea arborescens) 的幼苗和豆荚的实验表明，7-羟基-4'-甲氧基异黄酮 (formononetin)、7,3'-二羟基-4'-甲氧基异黄酮 (花萼)、 7,2',3'-三羟基-4'-甲氧基异黄酮 (koparin) 和 7,2'-二羟基-3',4'-二甲氧基异黄酮是 (3 R )-isomucronulatol (7,2'-dihydroxy- 3',4'-二甲氧基异黄烷）。然而，7,2'-二羟基-4'-甲氧基异黄酮（2'-羟基甲氧基异黄酮）和7-羟基-3',4'-二甲氧基异黄酮（cladrin）是较差的底物。因此，从芒柄花素到异木糖醇的生物合成顺序包括 3'-羟基化、2'-羟基化和 3'-O-甲基化，然后大概是 7,2'-二羟基-3',4'-二甲氧基异黄酮的立体定向还原。处理 2',3',
• Isoflavans and a pterocarpan from Astragalus mongholicus
  作者：Anas Subarnas、Yoshiteru Oshima、Hiroshi Hikino

  DOI：10.1016/0031-9422(91)85143-n

  日期：1991.1

  Abstract Three new isoflavans, 7- O -methylisomucronulatol, isomucronulatol 7,2′-di- O -glucoside, 5′-hydroxyisomucronulatol 2′,5′-di- O -glucoside, and one new pterocarpan, 3,9-di- O -methylnissolin were isolated from Astragalus mongholicus roots. Their structures were established by spectral analyses and chemical conversions.

  摘要 三种新的异黄烷，7-O-甲基异鼠尾醇，异鼠尾醇 7,2'-二-O-葡萄糖苷，5'-羟基异鼠尾醇 2',5'-二-O-葡萄糖苷，和一种新的紫檀醇，3,9-二- O-methylnissolin 是从黄芪根中分离出来的。它们的结构是通过光谱分析和化学转化确定的。