6-O-(α-L-rhamnopyranosyl)catalpol | 69484-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(α-L-rhamnopyranosyl)catalpol
• 英文别名: 6-O-α-L-rhamnopyranosylcatalpol；6-O-rhamnopyranosyl-catalpol；α-L-rhamnopyranose；(2S,3R,4R,5R,6S)-2-[[(1S,2S,4S,5S,6R,10S)-2-(hydroxymethyl)-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,9-dioxatricyclo[4.4.0.02,4]dec-7-en-5-yl]oxy]-6-methyloxane-3,4,5-triol
• CAS: 69484-83-9
• 化学式: C₂₁H₃₂O₁₄
• 分子量: 508.477
• InChiKey: GRLJTTHDCMSLHP-QHTRAVTJSA-N

物化性质

• 沸点：
  791.8±60.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  221
• 氢给体数：
  8
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  6-O-(α-L-rhamnopyranosyl)catalpol 在 sodium hydroxide 作用下， 反应 24.0h， 生成 verbascoside B
  参考文献：
  名称：

  Verbascoside B — A minor iridoid ofVerbascum georgicum

  摘要：

  DOI：

  10.1007/bf00576077
• 作为产物：
  描述：

  6-α-L-(2"-caffeoyl)rhamnopyranosylcatalpol 在 sodium hydroxide 作用下， 生成 6-O-(α-L-rhamnopyranosyl)catalpol
  参考文献：
  名称：

  来自 Premna odorata 的两种环烯醚萜糖苷咖啡酸酯

  摘要：

  摘要 从 Premna odorata 中分离出的两种新环烯醚萜苷分别为 2"- 和 3"-caffeoyl-6-α-l-rhamnopyranosylcatalpol。通过鼠李糖部分的 13 C NMR 信号中明显的酰化位移确定了这些化合物中每一种中酰基部分的位置。

  DOI：

  10.1016/0031-9422(89)80044-5

文献信息

• 6-O-α-l-(2″-O- and 3″-O-isoferuloyl) rhamnopyranosylcatalpols from Premna japonica
  作者：Hideaki Otsuka、Yukari Sasaki、Kazuo Yamasaki、Yoshio Takeda、Tarow Seki

  DOI：10.1016/0031-9422(89)80282-1

  日期：1989.1

  Abstract From the methanol extract of the leaves of Premna japonica , two new monoacyl 6- O -α- l -rhamnopyranosyl-catalpols were isolated. The structures of these compounds were determined to be 6- O -α- l -(2″- O -isoferuloyl and 3″- O -isoferuloyl)rhamnopyranosylcatalpols by NMR spectroscopy and chemical conversions.

  摘要 从白菜叶甲醇提取物中分离得到两种新的单酰基6-O-α-l-鼠李糖基-梓醇。这些化合物的结构通过NMR光谱和化学转化确定为6-O-α-1-(2″-O-异阿魏酰基和3″-O-异阿魏酰基)鼠李糖基梓醇。
• Isolation and characterization of new diacyl 6-O-.ALPHA.-L-rhamnopyranosylcatalpols from the leaves of Premna japonica Miq.
  作者：Hideaki OTSUKA、Yukari SASAKI、Kazuo YAMASAKI、Yoshio TAKEDA、Tarow SEKI

  DOI：10.1248/cpb.38.426

  日期：——

  Two diacyl rhamnopyranosylcatalpols were isolated from the leaves of Premna japonica. The structures of the compounds were determined to be 6-O-α-L-(2"-O-isoferuloyl, 4"-O-acetyl)rhamnopyranosylcatalpol and 6-O-α-L-(3"-O-isoferuloyl, 4"-O-acetyl)rhamnopyranosylcatalpol. The locations of acyl moieties were determined by long-range proton selective decoupling experiments and by partial alkaline hydrolysis.

  从白花蛇舌草（Premna japonica）的叶子中分离出了两种二酰基鼠李糖基宿主酚。化合物的结构被确定为 6-O-α-L-（2"-O-异阿魏酰，4"-O-乙酰基）rhamnopyranosylcatalpol 和 6-O-α-L-（3"-O-异阿魏酰，4"-O-乙酰基）rhamnopyranosylcatalpol。酰基的位置是通过长程质子选择性解偶联实验和部分碱性水解来确定的。
• Koelzioside, an iridoid diglycoside from Scrophularia koelzii
  作者：S.P.S. Bhandri、Anil Mishra、Raja Roy、H.S. Garg

  DOI：10.1016/0031-9422(92)90061-t

  日期：1992.2

  A new iridoid diglycoside named koclzioside has been isolated from Scrophularia koelzii. The structure of koelzioside was elucidated by chemical and spectral analysis as 6-O-(2'',3''-di-O-cinnamoyl-4''-O-acetyl)-alpha-l-rhamnopyranosyl catalpol.
• Premnosides A–D: Diacyl 6-O-α-l-rhamnopyranosylcatalpols from Premna odorata
  作者：Hideaki Otsuka、Naoko Kubo、Kazuo Yamasaki、William G. Padolina

  DOI：10.1016/0031-9422(89)80281-x

  日期：——
• Two iridoid glycoside caffeoyl esters from Premna odorata
  作者：Hideaki Otsuka、Naoko Kubo、Kazuo Yamasaki、William G. Padolina

  DOI：10.1016/0031-9422(89)80044-5

  日期：——

  Abstract Two new iridoid glycosides isolated from Premna odorata were shown to be 2″- and 3″-caffeoyl-6-α- l -rhamnopyranosylcatalpol respectively. The position of the acyl moiety in each of these compounds was established by the distinct acylation shifts in the 13 C NMR signals of the rhamnose moiety.

  摘要 从 Premna odorata 中分离出的两种新环烯醚萜苷分别为 2"- 和 3"-caffeoyl-6-α-l-rhamnopyranosylcatalpol。通过鼠李糖部分的 13 C NMR 信号中明显的酰化位移确定了这些化合物中每一种中酰基部分的位置。