carnosic acid 12-methyl ether γ-lactone | 142279-39-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: carnosic acid 12-methyl ether γ-lactone
• 英文别名: Carnosic acid gamma-lactone 12-methyl ether；(1R,6S)-12-methoxy-5,5-dimethyl-11-propan-2-yl-14-oxatetracyclo[7.6.1.01,6.013,16]hexadeca-9,11,13(16)-trien-15-one
• CAS: 142279-39-8
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: SRVNMMQHMRWDTR-YCRPNKLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 carnosic acid 12-methyl ether γ-lactone 在 盐酸 作用下， 反应 0.08h， 以99%的产率得到methyl carnosate 12-methyl ether
  参考文献：
  名称：

  The Isolation of Carnosic Acid 12-Methyl Ether from Salvia officinalis L. and NMR Study of Its Methyl Ester

  摘要：

  在我们对栽培鼠尾草（学名：Salvia officinalis L.）的空气部分的化学成分研究中，我们首次从这种鼠尾草中分离出了标题物质。通过光谱数据和一些化学反应，我们确定了这个分离化合物的结构。对¹H和¹³C NMR、同核（COSY）(¹H-¹H)、异核（HETCOR）(¹H-¹³C)和选择性INEPT光谱的研究，使我们能够明确地分配¹H和¹³C NMR光谱，并有可能解决类似天然产物的信号。

  DOI：

  10.1135/cccc19931919
• 作为产物：
  描述：

  12-O-甲基鼠尾草酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以81%的产率得到carnosic acid 12-methyl ether γ-lactone
  参考文献：
  名称：

  Gastroprotective Effect of Carnosic Acid γ-Lactone Derivatives

  摘要：

  Carnosic acid (1) has been shown to possess gastroprotective activity in vitro and in vivo. However, little is known of the gastroprotective effect or cytotoxicity of carnosic acid gamma-lactone (3). To determine structure activity relationships, a series of 17 esters of 3 were prepared including aliphatic, aromatic, and heterocyclic derivatives. Also, two units of 3 were coupled with succinic and phthalic acid as linkers. The compounds were assessed for their gastroprotective effect in the HCl/EtOH-induced gastric lesions model in mice and for cytotoxicity in human lung fibroblasts, human adenocarcinoma AGS cells, and Hep G2 hepatocellular carcinoma cells. At a single oral dose of 40 mg/kg, the gastroprotective effect increased moderately with the length of the alkyl chain. The best effects were observed for the butyrate (9) and chloroacetate (6) derivatives. Activity of fatty acid esters increased with chain length but decreased with unsaturation. The best gastroprotective effect, with lowest cytotoxicity, was found for the palmitate (11) and oleate (12) derivatives.

  DOI：

  10.1021/np900822x

文献信息

• Gastroprotective Effect of Carnosic Acid γ-Lactone Derivatives
  作者：Mariano Walter Pertino、Cristina Theoduloz、Jaime A. Rodríguez、Tania Yáñez、Viviana Lazo、Guillermo Schmeda-Hirschmann

  DOI：10.1021/np900822x

  日期：2010.4.23

  Carnosic acid (1) has been shown to possess gastroprotective activity in vitro and in vivo. However, little is known of the gastroprotective effect or cytotoxicity of carnosic acid gamma-lactone (3). To determine structure activity relationships, a series of 17 esters of 3 were prepared including aliphatic, aromatic, and heterocyclic derivatives. Also, two units of 3 were coupled with succinic and phthalic acid as linkers. The compounds were assessed for their gastroprotective effect in the HCl/EtOH-induced gastric lesions model in mice and for cytotoxicity in human lung fibroblasts, human adenocarcinoma AGS cells, and Hep G2 hepatocellular carcinoma cells. At a single oral dose of 40 mg/kg, the gastroprotective effect increased moderately with the length of the alkyl chain. The best effects were observed for the butyrate (9) and chloroacetate (6) derivatives. Activity of fatty acid esters increased with chain length but decreased with unsaturation. The best gastroprotective effect, with lowest cytotoxicity, was found for the palmitate (11) and oleate (12) derivatives.
• The Isolation of Carnosic Acid 12-Methyl Ether from Salvia officinalis L. and NMR Study of Its Methyl Ester
  作者：Zoltan Djarmati、Ratko M. Jankov、János Csanádi、Aleksandar Djordjevic

  DOI：10.1135/cccc19931919

  日期：——

  In continuation of our studies on the chemical compositions of the aerial parts of cultivated Salvia officinalis L., we have isolated the title substance for the first time in this type of Sage. The structure of this isolated compound was established by spectroscopic data and some chemical reactions. Investigation of ¹H and ¹³C NMR, homonuclear (COSY) (¹H-¹H), heteronuclear (HETCOR) (¹H-¹³C), and selective INEPT spectra, permitted the unambiguous assignment of the ¹H and ¹³C NMR spectra, what gave the possibility to resolve signals of similar natural products.

  在我们对栽培鼠尾草（学名：Salvia officinalis L.）的空气部分的化学成分研究中，我们首次从这种鼠尾草中分离出了标题物质。通过光谱数据和一些化学反应，我们确定了这个分离化合物的结构。对¹H和¹³C NMR、同核（COSY）(¹H-¹H)、异核（HETCOR）(¹H-¹³C)和选择性INEPT光谱的研究，使我们能够明确地分配¹H和¹³C NMR光谱，并有可能解决类似天然产物的信号。