methyl zizanoate | 18444-89-8

• 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: methyl zizanoate
• 英文别名: (8aS)-7.7-dimethyl-8-methylene-(8arH)-octahydro-3H-3ac.6c-methano-azulene-carboxylic acid-(3c)-methyl ester；(8aS)-7.7-Dimethyl-8-methylen-(8arH)-octahydro-3H-3ac.6c-methano-azulen-carbonsaeure-(3c)-methylester；Zizanosaeuremethylester；Methyl-zizanonat；Methylzizanoat；1H-3a,6-Methanoazulene-3-carboxylic acid, octahydro-7,7-dimethyl-8-methylene-, methyl ester, (3S,3aR,6R,8aS)-；methyl (1R,2S,5S,8R)-7,7-dimethyl-6-methylidenetricyclo[6.2.1.01,5]undecane-2-carboxylate
• CAS: 18444-89-8
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: DZVKVIGAEDEAIN-BRXULGCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl zizanoate 在 吡啶 、 lithium aluminium tetrahydride 作用下， 生成 (+/-)-zizaene
  参考文献：
  名称：

  Stereoselective total synthesis of (+)-zizaene

  摘要：

  DOI：

  10.1021/ja00770a040
• 作为产物：
  描述：

  zizanoic alcohol 在 chromium(VI) oxide 、 硫酸 作用下， 生成 methyl zizanoate
  参考文献：
  名称：

  Trivedi,G.K. et al., Indian Journal of Chemistry, 1971, vol. 9, p. 1049 - 1051

  摘要：

  DOI：

文献信息

• A stereospecific total synthesis of zizanoic and isozizanoic acids
  作者：D.F. MacSweeney、R. Ramage

  DOI：10.1016/s0040-4020(01)98013-5

  日期：1971.1

  The total syntheses of zizanoic and isozizanoic acids, 5a and 37a respectively have been achieved starting from D(+)-camphor and utilising rearrangement of a tricyclo [6.2.1.01,6] undecane system to form the desired tricycle [6.2.1.01,5] undecane skeleton of the tricyclovetivane class of sesquiterpenes. An intermediate (33) has also been synthesised which can be transformed into epizizanoic acid (36a)

  的zizanoic和isozizanoic酸，全合成图5a和37A分别已经实现从d（+）起始-樟脑和利用三环[6.2.1.0的重排1,6 ]十一烷的系统，形成所需的三轮车[6.2.1.0 1 ，5 ]倍半萜的三环维十一烷类的十一烷骨架。还合成了中间体（33），该中间体可以转化为表哌嗪酸（36a）。
• Insect repellents from vetiver oil: I. zizanal and epizizanal
  作者：Subhash C. Jain、Stephen Nowicki、Thomas Eisner、Jerrold Meinwald

  DOI：10.1016/s0040-4039(00)85675-0

  日期：1982.1

  On the basis of spectral data and partial syntheses, structure 1 and 2 are established for zizanal and epizizanal, two new insect-repelling aldehydes isolated from Javanese vetiver oil (Vetiveria zizanoides).

  根据光谱数据和部分合成，分别从爪哇香根草油（Vetiveria zizanoides）中分离出的两个新的驱虫醛zizanal和epizizanal建立了结构1和2。
• Stereoselective total synthesis of (+)-zizaene
  作者：Robert M. Coates、Roger L. Sowerby

  DOI：10.1021/ja00770a040

  日期：1972.7
• Valorization of Brazilian Vetiver (<i>Vetiveria zizanioides </i>(L.) Nash ex Small) Oil
  作者：Julian Martinez、Paulo T. V. Rosa、Chantal Menut、Alain Leydet、Pierre Brat、Dominique Pallet、M. Angela A. Meireles

  DOI：10.1021/jf049182x

  日期：2004.10.1

  The valorization of extracts from Brazilian vetiver (Vetiveria zizanioides (L.) Nash ex Small) roots was studied. This study took into account the extraction method, the chemical composition of the extracts, their sensorial characteristics, and the possibility of chemical transformations of the product. The performed extraction methods were hydrodistillation and extraction with supercritical carbon dioxide. Some pretreatment methods were tested on the vetiver roots and evaluated in terms of extraction yield, process time, chemical composition, and sensorial properties. Supercritical carbon dioxide extraction resulted in high yield (3.2%) in significantly less time than the other methods. The chemical compositions of the extracts obtained by the different methods were also compared to those of commercial vetiver oils from other sources, showing that Brazilian samples had a greater acid amount. An extraction in basic medium from Brazilian vetiver oil was done to remove its main acid (zizanoic acid), which was chemically transformed into an alcohol (khusimol) of desirable sensorial properties. Sensory evaluation indicated that the Brazilian volatile oil without acid could be used in perfumery and the extract obtained with supercritical carbon dioxide could have application in food.
• Sesquiterpenoids of vetiver oil—I
  作者：N. Hanayama、F. Kido、R. Tanaka (née Sakuma)、H. Uda、A. Yoshikoshi

  DOI：10.1016/0040-4020(73)80044-4

  日期：1973.1