islandic acid I methyl ester | 85998-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: islandic acid I methyl ester
• 英文别名: islandic acid-I methyl ester；islandic acid methyl ester；[5-(hydroxymethyl)-4-methoxy-6-[(E)-3-methoxy-3-oxoprop-1-enyl]-2-oxopyran-3-yl]methyl (2Z,4E)-hexa-2,4-dienoate
• CAS: 85998-71-6
• 化学式: C₁₈H₂₀O₈
• 分子量: 364.352
• InChiKey: YNDNVBYUPJUKAH-QCPPJIGLSA-N

物化性质

• 沸点：
  569.5±50.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2(Z),4(E)-sorbic acid 在 4-二甲氨基吡啶 、 dimethyl sulfide borane 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 islandic acid I methyl ester
  参考文献：
  名称：

  Total Synthesis of Islandic Acid I Methyl Ester, Rosellisin and Rosellisin Aldehyde

  摘要：

  Total synthesis of islandic acid I methyl ester (2), rosellisin (3) and rosellisin aldehyde (4) has been accomplished starting from 4-hydroxy-5-hydroxymethyl-6-methyl-2H-pyran-2-one (9a) via formylation of 9a with dichloromethyl methyl ether and titanium tetrachloride as a key step.

  DOI：

  10.3987/com-93-6568

文献信息

• Studies on the biological activities of islandic acid and related compounds.
  作者：YASUO FUJIMOTO、TSUYOSHI KIHARA、KIYOSHI ISONO、HIROSHI TSUNODA、TAKASHI TATSUNO、KOUJI MATSUMOTO、HIDEO HIROKAWA

  DOI：10.1248/cpb.32.1583

  日期：——

  The effects of islandic acid-I (1) and related compounds on the growth of Yosida sarcoma cells and on the transfection of Bacillus phage M2-DNA have been investigated. Compound 1 inhibited the growth of Yoshida sarcoma cells at 100μg/ml, while its methyl ester (2) was 100 times more potent. Islandic acid-II methyl ester (4) and 2 produced 83 and 97% inhibition of the transfection of Bacillus phage M2-DNA at 33 and 66μg/ml, respectively. Methyl (2Z, 4E)-hexadienoate (5), having the same configuration as the side chain of 1, also inhibited the transfection of M2-DNA over a wide concentration range, but did not show cytotoxicity against Yoshida sarcoma cells in tissue culture even at 100μg/ml.

  已对岛状酸-I（1）和相关化合物对Yosida肉瘤细胞生长和Bacillus phage M2-DNA转染的影响进行了研究。化合物1在100μg/ml浓度下抑制了Yoshida肉瘤细胞的生长，而其甲基酯（2）的效力则高出100倍。岛状酸-II甲基酯（4）和2在33和66μg/ml浓度下分别对Bacillus phage M2-DNA转染产生83%和97%的抑制作用。甲基（2Z，4E）-己二烯酸酯（5）与1的侧链具有相同的结构，在较宽的浓度范围内也抑制了M2-DNA的转染，但在组织培养中即使浓度达到100μg/ml，也未显示对Yoshida肉瘤细胞的细胞毒性。
• Structure of lslandic acid, a new metabolite from Penicillium islandicum Sopp.
  作者：Yasuo Fujimoto、Hirsohi Tsunoda、Jun Uzawa、Takashi Tatsuno

  DOI：10.1039/c39820000083

  日期：——

  The structure of islandic acid a new anit-tumour metabolite isolated from P. islandicum Sopp., has been determined by the application of 13C–1H} long range selective proton decoupling experiments on its methyl ester.

  岛酸的结构是一种从P. islandicum Sopp。分离得到的新的抗肿瘤代谢物，已通过对其甲酯应用13 C– 1 H}远程选择性质子去偶联实验来确定。
• Total Synthesis of Islandic Acid I Methyl Ester, Rosellisin and Rosellisin Aldehyde
  作者：Takeshi Shimizu、Sayoko Hiranuma、Tsumoru Watanabe、Masayuki Kirihara

  DOI：10.3987/com-93-6568

  日期：——

  Total synthesis of islandic acid I methyl ester (2), rosellisin (3) and rosellisin aldehyde (4) has been accomplished starting from 4-hydroxy-5-hydroxymethyl-6-methyl-2H-pyran-2-one (9a) via formylation of 9a with dichloromethyl methyl ether and titanium tetrachloride as a key step.