(3R,5S)-3,5-Dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane | 153381-09-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (3R,5S)-3,5-Dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane
• 英文别名: (3R,5S)-1,7-Bis(4-hydroxy-3-methoxyphenyl)heptan-3,5-diol；meso-octahydrocurcumin；octahydrocurcumin；meso-OHC；(3R,5S)-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol；meso-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-diol
• CAS: 153381-09-0
• 化学式: C₂₁H₂₈O₆
• 分子量: 376.45
• InChiKey: OELMAFBLFOKZJD-CALCHBBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3R,5S)-3,5-Dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane 在 吡啶 作用下， 生成 [4-[(3S,5R)-3,5-diacetyloxy-7-(4-acetyloxy-3-methoxyphenyl)heptyl]-2-methoxyphenyl] acetate
  参考文献：
  名称：

  Constituents of Zingiberaceae. I. Diarylheptanoids from the rhizomes of ginger (Zingiber officinale Roscoe).

  摘要：

  两种新的二芳基庚烷，meso-3, 5-二乙酰氧基-1, 7-双(4-羟基-3-甲氧基苯基)庚烷 (3a) 和 3, 5-二乙酰氧基-1-(4-羟基-3, 5-二甲氧基苯基)从生姜 (Zingiber officinale ROSCOE) 的根茎中分离出 -7-(4-羟基-3-甲氧基苯基)庚烷 (4a)、脱羟基四氢姜黄素 (gingerenone A, 1) 和六氢姜黄素 (2)。它们的结构是根据化学和光谱证据阐明的。

  DOI：

  10.1248/cpb.39.120
• 作为产物：
  描述：

  (3R,5R)-1,7-bis(4-benzyloxy-3-methoxyphenyl)hept-1-ene-3,5-diol 在 10% palladium on carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 6.0h， 以90%的产率得到(3R,5S)-3,5-Dihydroxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane
  参考文献：
  名称：

  从d-葡萄糖开始，立体保守合成顺式-二芳基庚烷类化合物（Zingiber的活性成分）

  摘要：

  一个高效和立体受控合成策略已经被开发，以访问SYN -diarylheptanoids，例如，2 ， 3，4 ，和图5b从起始d -葡萄糖作为手性池。这些庚类化合物中存在的3-（R），5-（S）-顺式-二醇立体化学是在合成转化过程中保持d-葡萄糖的C2和C4立体化学后获得的。该合成策略的关键特征包括：（i）将d-葡萄糖转化为已知的手性模板6，该模板具有所需的1,3-装甲。顺式二醇立体化学以及两个末端醛官能团，用于构建定制的“二芳基翅膀”；（ii）通过在C5-醛上的初始Wittig烯化反应将6转化为7；（ⅲ）利用半缩醛的7作为共同中间体使用适当选择的叶立德获得经由第二Wittig反应的个体heptanoids在其异头中心。

  DOI：

  10.1016/j.tetlet.2011.04.097

文献信息

• Microbial Conversion of Curcumin into Colorless Hydroderivatives by the Endophytic Fungus Diaporthe sp. Associated with Curcuma longa
  作者：Shoji Maehara、Michiteru Ikeda、Hiroyuki Haraguchi、Chinami Kitamura、Tetsuro Nagoe、Kazuyoshi Ohashi、Hirotaka Shibuya

  DOI：10.1248/cpb.59.1042

  日期：——

  We investigated the microbial conversion of curcumin (1) using endophytic fungi associated with the rhizome of Curcuma longa (Zingiberaceae). We found that Diaporthe sp., an endophytic filamentous fungus, converts curcumin (1) into four colorless derivatives, namely (3R,5R)-tetrahydrocurcumin (2), a novel (3R,5S)-hexahydrocurcumin (3) named neohexahydrocurcumin, (3S,5S)-octahydrocurcumin (4) and meso-octahydrocurcumin (5).

  我们利用与姜黄（姜科）根茎相关的内生真菌研究了姜黄素（1）的微生物转化。我们发现内生丝状真菌 Diaporthe sp.能将姜黄素（1）转化为四种无色衍生物，即（3R,5R）-四氢姜黄素（2）、一种名为新六氢姜黄素的新型（3R,5S）-六氢姜黄素（3）、（3S,5S）-八氢姜黄素（4）和中八氢姜黄素（5）。
• <i>In Vitro</i> Production of Optically Active Octahydrocurcumin by Human Intestinal Bacterium
  作者：Toshio Niwa、Shin-ichiro Yokoyama、Mika Mochizuki、Toshihiko Osawa

  DOI：10.1248/bpb.b21-00992

  日期：2022.3.1

  Enterococcus avium, producing 5R-hexahydrocurcumin metabolized tetrahydrocurcumin to octahydrocurcumin in vitro. Based on a detailed analysis of the two secondary alcohols, the metabolite obtained from tetrahydrocurcumin via 5R-hexahydrocurcumin was identified as 3R,5R-octahydrocurcumin. The activities of 5R-hexahydrocurcumin and 3R,5R-octahydrocurcumin were compared to those of the synthetic compounds, using monocyte chemoattractant protein-1 produced via murine adipocytes in vitro. The optically active curcuminoids reduced the cytokine production similar to tetrahydrocurcumin without any difference in their stereochemistry.

  鸟肠球菌产生 5R-六氢姜黄素，在体外将四氢姜黄素代谢为八氢姜黄素。基于对两种仲醇的详细分析，四氢姜黄素经5R-六氢姜黄素得到的代谢物被鉴定为3R,5R-八氢姜黄素。使用小鼠脂肪细胞体外产生的单核细胞趋化蛋白-1，将 5R-六氢姜黄素和 3R,5R-八氢姜黄素的活性与合成化合物的活性进行比较。光学活性姜黄素与四氢姜黄素类似，可减少细胞因子的产生，但其立体化学没有任何差异。
• Chiroptical spectroscopic studies for the absolute configuration determination of hexahydrocurcumin and octahydrocurcumin
  作者：Andrew R. Puente、Kalyanam Nagabhushanam、Savita Ganjihal、Muhammed Majeed、Prasad L. Polavarapu

  DOI：10.1002/chir.23511

  日期：2022.12

  Hexahydrocurcumin (HHC) and octahydrocurcumin (OHC) were synthesized, and their enantiomers were separated using supercritical fluid chromatography. The absolute configurations (ACs) of HHC and OHC were independently determined using experimental measurements and quantum theoretical predictions of vibrational circular dichroism, electronic circular dichroism, and optical rotatory dispersion. These

  合成了六氢姜黄素 (HHC) 和八氢姜黄素 (OHC)，并使用超临界流体色谱分离了它们的对映体。HHC 和 OHC 的绝对构型 (AC) 是使用振动圆二色性、电子圆二色性和旋光色散的实验测量和量子理论预测独立确定的。这些研究导致 (−)-( R )-HHC 和 (+)-( R , R )-OHC 的 AC 分配。OHC 的 AC 由单晶 X 射线衍射确定的结构进一步证实。
• Chemical and<i>in vitro</i>biological formation of octahydrocurcumin stereoisomers, and<i>in vitro</i>activity of raceme and<i>meso</i>-octahydrocurcumin
  作者：Toshio Niwa、Yoji Kato、Toshihiko Osawa

  DOI：10.1093/bbb/zbac204

  日期：2023.2.24

  meso-octahydrocurcumin than raceme octahydrocurcumin. Similar result was found in the product obtained from tetrahydrocurcumin and NaBH4, whereas using palladium carbon as a catalyst increased the meso-octahydrocurcumin ratio. Compared with chemical methods, baker's yeast produced 3S,5S-octahydrocurcumin and meso-octahydrocurcumin from tetrahydrocurcumin. The different activity between raceme and meso-octahydrocurcumin

  PtO2 催化的姜黄素氢化产生的内消旋八氢姜黄素比消旋体八氢姜黄素略占优势。在由四氢姜黄素和 NaBH4 获得的产物中发现了类似的结果，而使用钯碳作为催化剂增加了内消旋八氢姜黄素的比率。与化学方法相比，面包酵母从四氢姜黄素中产生3S、5S-八氢姜黄素和内消旋八氢姜黄素。在我们的实验中没有发现消旋体和内消旋八氢姜黄素之间的不同活性。
• Synthesis of gingerol and diarylheptanoids
  作者：Gowravaram Sabitha、Chitti Srinivas、Teega Rammohan Reddy、Kurra Yadagiri、Jhillu Singh Yadav

  DOI：10.1016/j.tetasy.2011.11.010

  日期：2011.12

  The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds. (C) 2011 Elsevier Ltd. All rights reserved.