(+)-fragransin A₂ | 50393-85-6

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: (+)-fragransin A₂
• 英文别名: fragransin A₂；(+)-fragransin A2；fragansin A2；4-[(2S,3S,4S,5S)-5-(4-hydroxy-3-methoxyphenyl)-3,4-dimethyloxolan-2-yl]-2-methoxyphenol
• CAS: 50393-85-6；50544-07-5；74683-16-2；76261-19-3；83198-63-4；112652-46-7；114422-21-8；126643-11-6；128524-98-1；131829-51-1；143062-67-3
• 化学式: C₂₀H₂₄O₅
• 分子量: 344.408
• InChiKey: GMXMKSFJQLFOSO-HIGYNYDNSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  509.7±50.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(-)-Galbelgin	10569-12-7	C22H28O5	372.461

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(-)-Galbelgin	10569-12-7	C22H28O5	372.461

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (+)-fragransin A₂ 以 乙醚 为溶剂， 反应 72.0h， 生成 (-)-Galbelgin
  参考文献：
  名称：

  黑曲霉对 7,7'-环氧木脂素的 O-去甲基化

  摘要：

  已经研究了黑曲霉对 7,7'-环氧木脂素、(+)-veraguensin、(+)-galbelgin 和 galgravin 的生物转化。这些木脂素被转化为它们相应的 4,4'-O-去甲基衍生物、(+)-verrucosin、(+)-fragransin A2 和 necandrin B。

  DOI：

  10.1016/0031-9422(96)00222-1
• 作为产物：
  描述：

  (7S,7′S,8R,8′R)-4,4′-dibenzyloxy-3,3′-dimethoxy-7,7′-epoxylignane-9,9′-diol 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 5%-palladium/activated carbon 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (+)-fragransin A₂
  参考文献：
  名称：

  Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity

  摘要：

  All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.

  DOI：

  10.1021/jf4046396

文献信息

• Synthesis of All Stereoisomers of 3,3′-Dimethoxy-7,7′-epoxylignane-4,4′-diol and Their Plant Growth Inhibitory Activity
  作者：Hisashi Nishiwaki、Kumiko Nakayama、Yoshihiro Shuto、Satoshi Yamauchi

  DOI：10.1021/jf4046396

  日期：2014.1.22

  All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.
• O-demethylation of 7,7′-epoxylignans by Aspergillus niger
  作者：Hiroyuki Kasahara、Mitsuo Miyazawa、Hiromu Kameoka

  DOI：10.1016/0031-9422(96)00222-1

  日期：1996.9

  Biotransformation of the 7,7'-epoxylignans, (+)-veraguensin, (+)-galbelgin and galgravin by Aspergillus niger has been investigated. These lignans were converted to their corresponding 4,4'-O-demethyl derivatives, (+)-verrucosin, (+)-fragransin A2 and nectandrin B.

  已经研究了黑曲霉对 7,7'-环氧木脂素、(+)-veraguensin、(+)-galbelgin 和 galgravin 的生物转化。这些木脂素被转化为它们相应的 4,4'-O-去甲基衍生物、(+)-verrucosin、(+)-fragransin A2 和 necandrin B。