(2E,4R,5R)-5-hydroxy-4-methylhex-2-enoic acid | 1318763-87-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4R,5R)-5-hydroxy-4-methylhex-2-enoic acid
• 英文别名: (4R,5R,2E)-5-hydroxy-4-methylhex-2-enoic acid；(E,4R,5R)-5-hydroxy-4-methylhex-2-enoic acid
• CAS: 1318763-87-9
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: RYNHARGJLCFBSO-BYVKAKODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  chaetomugilin P 在 对甲苯磺酸 、 potassium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 (2E,4R,5R)-5-hydroxy-4-methylhex-2-enoic acid
  参考文献：
  名称：

  New class azaphilone produced by a marine fish-derived Chaetomium globosum. The stereochemistry and biological activities

  摘要：

  Four new metabolites, chaetomugilins P-R and 11-epi-chaetomugilin I, were isolated from a strain of Chaetomium globosum originally obtained from the marine fish Mugil cephalus, and their absolute stereo-structures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR techniques and various chemical transformations. Particularly, the skeleton of chaetomugilin P is different from that of other azaphilones isolated from this fungal strain to date. In addition, these compounds significantly inhibited the growth of cultured P388, HL-60, L1210 and KB cell lines. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.05.008

文献信息

• Three new azaphilones produced by a marine fish-derived chaetomium globosum
  作者：Takeshi Yamada、Masaaki Jinno、Takashi Kikuchi、Tetsuya Kajimoto、Atsushi Numata、Reiko Tanaka

  DOI：10.1038/ja.2012.40

  日期：2012.8

  were isolated from a strain of Chaetomium globosum originally obtained from the marine fish Mugil cephalus, and their absolute stereostructures were elucidated based on the basis of spectroscopic analyses, including 1D and 2D NMR techniques and some chemical transformations. Particularly, chaetomugilins T and U are the first compounds without a chlorine atom in azaphilones isolated from this fungal strain

  从最初从海水鱼Mugil cephalus的球壳拟杆菌（Chaetomium globosum）菌株中分离出了三种新的代谢产物，即chaetomugilin S，dechloro-chaetomugilin D和dechloro-chaetomugilin D，并基于光谱分析，包括1D，阐明了它们的绝对立体结构。和2D NMR技术以及一些化学转化。特别地，迄今为止，脂粘蛋白T和U是在从该真菌菌株分离的氮杂苯甲酮中首先没有氯原子的化合物。此外，这些化合物适度抑制了培养的P388，HL-60，L1210和KB细胞系的生长。
• 11- and 4′-Epimers of Chaetomugilin A, Novel Cytostatic Metabolites from Marine Fish-Derived Fungus<i>Chaetomium globosum</i>
  作者：Yasuhide Muroga、Takeshi Yamada、Atsushi Numata、Reiko Tanaka

  DOI：10.1002/hlca.200900272

  日期：2010.3

  11‐ and 4′‐epichaetomugilin A were isolated from a strain of Chaetomium globosum that was originally isolated from the marine fish Mugil cephalus. 11‐Epichaetomugilin A is the first compound to have an opposite absolute configuration at C(11) to that of other azaphilones isolated to date. Their absolute configurations were elucidated on the basis of spectroscopic analyses, including 1D‐ and 2D‐NMR

  从最初从海鱼Mugil cephalus中分离出的Chaetomium globosum菌株中分离出11和4'-epichaetomugilinA 。11-Epichaetomugilin A是第一个在C（11）处具有与迄今分离的其他氮杂甲酮相反的绝对构型的化合物。在光谱分析的基础上阐明了它们的绝对构型，包括一维和二维核磁共振技术以及一些化学转化。11-Epichaetomugilin弱抑制培养的P388细胞和HL-60细胞的生长（IC 50 88.9和66.7μ中号，RESP）。
• Chaetomugilins I–O, new potent cytotoxic metabolites from a marine-fish-derived Chaetomium species. Stereochemistry and biological activities
  作者：Yasuhide Muroga、Takeshi Yamada、Atsushi Numata、Reiko Tanaka

  DOI：10.1016/j.tet.2009.06.125

  日期：2009.9

  Chaetomugilins I-O were isolated from a strain of Chaetomium globosum originally isolated from the marine fish Mugil cephalus, and their absolute stereostructures were elucidated on the basis of spectroscopic analyses, including 1D and 2D NMR techniques, as well as chemical transformations. These compounds exhibited significant growth inhibition of cultured P388, HL-60, L1210, and KB cell lines. In addition, chaetomugilin I showed selective cytotoxic activity against 39 human cancer cell lines. (C) 2009 Elsevier Ltd. All rights reserved.