methyl (6S)-2-trans-6-hydroxy-2,6-dimethyl-2,7-octadienoate | 75979-27-0

• 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: methyl (6S)-2-trans-6-hydroxy-2,6-dimethyl-2,7-octadienoate
• 英文别名: (6S)-2-trans-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid methyl ester；(2E,6S)-2,6-dimethyl-6-hydroxy-2,7-octadienoic acid methyl ester；(+)-(2E,6S)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid methyl ester；methyl (2E,6S)-6-hydroxy-2,6-dimethylocta-2,7-dienoate
• CAS: 75979-27-0
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: NWDBBLFNNILKKJ-MXMFLMJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  jashemsloside C 在 acetate buffer 、 sodium methylate 作用下， 反应 7.5h， 生成 methyl (6S)-2-trans-6-hydroxy-2,6-dimethyl-2,7-octadienoate
  参考文献：
  名称：

  Structure Elucidation of Six Acylated Iridoid Glucosides from Jasminum hemsleyi.

  摘要：

  从茉莉叶中分离出六种新的萜烯甙，即茉莉甙A-D（2-5）、6'-O-反式对香豆酰表儿茶素（6）和6'-O-顺式对香豆酰表儿茶素（7），以及已知的甙类，即表儿茶素、7-脱氢表儿茶素、茉莉甙、10-羟基油甙二甲酯和落叶松脂素-4-O-β-D-葡萄糖苷。通过光谱和化学研究，阐明了新甙类2-7的结构，其中除了表儿茶素部分外，还含有薄荷酸单元或对香豆酰基。对由2和3制备的单萜酸衍生物进行手性高效液相色谱分析，发现每种新化合物都是两种不可分离的非对映异构体的混合物。

  DOI：

  10.1248/cpb.43.729

文献信息

• Studies on the constituents of leguminous plants. VI. The structure elucidations of monoterpene glycosides from fruits of Gymnocladus chinensis Baillon.
  作者：TAKAO KONOSHIMA、TOKUNOSUKE SAWADA

  DOI：10.1248/cpb.32.2617

  日期：——

  Two monoterpene glycosides 1 and 2 were isolated from the fruits of Gymnocladus chinensis BAILLON (Leguminosae). On the basis of chemical and physicochemical evidence, these glycosides were characterized as (6S)-2-trans-6-α-L-arabinopyranosyloxy-2, 6-dimethyl-2, 7-octadienoic acid and (6S)-2-trans-2, 6-dimethyl-6-[3-O-(β-D-glucopyranosyl)-4-O-(2-methylbutyroyl)-α-L-arabino-pyranosyloxy]-2, 7-octadienoic acid.

  从中国南木豆的果实中分离出两种单萜糖苷1和2。根据化学和物理化学证据，这些糖苷的特征被确定为(6S)-2-trans-6-α-L-阿拉伯吡喃糖氧基-2, 6-二甲基-2, 7-辛二烯酸和(6S)-2-trans-2, 6-二甲基-6-[3-O-(β-D-葡萄糖吡喃糖基)-4-O-(2-甲基丁酰)-α-L-阿拉伯吡喃糖氧基]-2, 7-辛二烯酸。
• Two diastereomeric saponins with cytotoxic activity from Albizia julibrissin
  作者：Kun Zou、Yuying Zhao、Guangzhong Tu、Jingrong Cui、Zhonghua Jia、Ruyi Zhang

  DOI：10.1016/s0008-6215(99)00294-3

  日期：2000.2

  [4-O-((6S)-2-trans-2,6-dimethyl-6-O-(beta-D-quinovopyranosyl)-2,7- octadienoyl)-beta-D-quinovopyranosyl]-2,7-octadienoyl] acacic acid-28-O-beta-D-glucopyranosyl-(1-->3)-[alpha-L-arabinofuranosyl-(1-->4 )]-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-glucopyranosyl ester. Saponin 2 is a new saponin named julibroside J9. Both julibrosides J1 and J9 show good inhibitory action against the KB cancer cell line in vitro

  从杜鹃花杜仲的茎皮中获得了两种非对映体皂苷，朱利哌利德J1（1）和J9（2），均显示出细胞毒活性。根据化学和光谱证据[LB Ma等，Carbohydr。Res。281（1996）35-46]，将1的结构修改为3-O- [β-D-吡喃吡喃糖基-（1-> 2）-alpha-L-阿拉伯吡喃糖基-（1-> 6 ）-β-D-吡喃葡萄糖基] -21-O-[（6S）-2-trans-2-羟甲基-6-甲基-6-O- [4-O-（（（6R）-2-trans-2， 6-二甲基-6-O-（β-D-喹啉并吡喃糖基）-2,7-辛二烯酰基）-β-D-喹啉并吡喃糖基] -2,7-辛二烯酰基]乙酸-28-O-β-D-吡喃葡糖基-（ 1-> 3）-[α-L-阿拉伯呋喃糖基-（1-> 4）]-α-L-鼠李糖基-（1-> 2）-β-D-吡喃葡萄糖基酯。1的非对映异构体2被确定为3-O-β-D-吡喃吡喃糖基-（1-> 2）-alpha-L-阿拉伯吡喃糖基-（1->
• Cytotoxic Oleanane Triterpene Saponins from <i>Albizia chinensis</i>
  作者：Rui Liu、Shuanggang Ma、Shishan Yu、Yuehu Pei、Sen Zhang、Xiaoguang Chen、Jianjun Zhang

  DOI：10.1021/np800576s

  日期：2009.4.24

  Three new oleanane-type triterpene saponins, albizosides A-C (1-3), were isolated from the stem bark of Albizia chinensis. Their structures were established by 1D and 2D NMR experiments and chemical methods. Compounds 1-3 showed cytotoxic activity against a small panel of human tumor cell lines as well as hemolytic activity against rabbit erythrocytes.
• Structure Elucidation of Six Acylated Iridoid Glucosides from Jasminum hemsleyi.
  作者：Takao TANAHASHI、Atsuko SHIMADA、Naotaka NAGAKURA、Kenichiro INOUE、Masami ONO、Tetsuro FUJITA、Cheng-Chang CHEN

  DOI：10.1248/cpb.43.729

  日期：——

  Six new iridoid glucosides, jashemslosides A-D (2-5), 6'-O-trans-p-coumaroylloganin (6) and 6'-O-cis-p-coumaroylloganin (7), were isolated from the leaves of Jasminum hemsleyi, together with the known glycosides, loganin, 7-dehydrologanin, jasminoside, 10-hydroxyoleoside dimethyl ester and lariciresinol-4-O-β-D-glucoside. The structures of the new glucosides 2-7, which contain a menthiafolic acid unit or p-coumaroyl group in addition to the loganin moiety, were elucidated by spectroscopic and chemical studies. Chirospecific HPLC analysis of the monoterpenic acid derivatives prepared from 2 and 3 revealed that each of the new compounds was a mixture of two inseparable diastereoisomers.

  从茉莉叶中分离出六种新的萜烯甙，即茉莉甙A-D（2-5）、6'-O-反式对香豆酰表儿茶素（6）和6'-O-顺式对香豆酰表儿茶素（7），以及已知的甙类，即表儿茶素、7-脱氢表儿茶素、茉莉甙、10-羟基油甙二甲酯和落叶松脂素-4-O-β-D-葡萄糖苷。通过光谱和化学研究，阐明了新甙类2-7的结构，其中除了表儿茶素部分外，还含有薄荷酸单元或对香豆酰基。对由2和3制备的单萜酸衍生物进行手性高效液相色谱分析，发现每种新化合物都是两种不可分离的非对映异构体的混合物。