(E)-2-methylgeranial | 73141-53-4

• 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: (E)-2-methylgeranial
• 英文别名: (E)-2,3,7-trimethyl-octa-2,6-dienal；2-methyl-geranial；2,3,7-trimethyl-2,6-octadiene-al；(2E)-2,3,7-trimethylocta-2,6-dienal
• CAS: 73141-53-4
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: WHMUVYIQFYVVKT-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-methylgeranial 在 sodium hydroxide 、 [³H]-sodium borohydride 、 水 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以75%的产率得到[1-³H]-2-methylgeraniol
  参考文献：
  名称：

  Biochemistry and Molecular Genetics of the Biosynthesis of the Earthy Odorant Methylisoborneol in Streptomyces coelicolor

  摘要：

  Methylisoborneol (2) is a volatile organic compound produced by a wide variety of Actinomycetes soil orgainisms, myxobacteria, and cyanobacteria. It has an unusually low odor threshold and, together with geosmin, is responsible for the characteristics smell of moist soil as well as unpleasant taste and odor episodes assoiciated with public water supplies and contamination of various foodstuffs, including fish, wine and beer. Despite considerable interest in detection and remediation of methylisoborneal, the biosynthesis of this methylated monoterpene has been obscure. In Streptomyces coelicor, the sco7700 and sco7701 genes are shown to correspond to a two-gene operon responsible for methylisoborneol biosynthesis. Both genes have been amplified by PCR and the resulting DNA has been cloned and expressed in Escherichia coli. Incubation of recombinant SCO7701 protein, annotated as a possible C-methyltransferase, with geranyl diphosphate (1) and S-adenosylmethionine gave the previously unknown compound. (E)-2-methylgeranyl diphosphate (3). Incubation of 3 in the presence of Mg2+ with recombinant SCO7700, previously annotated only as a possible metal-binding protein or terpenoid synthase, resulted in the formation of 2-methylisoborneal (2). The steady-state kinetic parameters for both biochemical reactions have been determined. Incubation of geranyl diphosphate and S-adenosylmethionine with a mixture of both SCO7700 and SCO7701 resulted in formation of methylisoborneal (2). Cyclization of 2-methylgeranyl diphosphate (3) to methylisoborneal (2) likely involves the intermediacy of 2-methylinalyl diphosphate.

  DOI：

  10.1021/ja803639g
• 作为产物：
  描述：

  (2E)-2,3,7-trimethylocta-2,6-dien-1-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (E)-2-methylgeranial
  参考文献：
  名称：

  Biochemistry and Molecular Genetics of the Biosynthesis of the Earthy Odorant Methylisoborneol in Streptomyces coelicolor

  摘要：

  Methylisoborneol (2) is a volatile organic compound produced by a wide variety of Actinomycetes soil orgainisms, myxobacteria, and cyanobacteria. It has an unusually low odor threshold and, together with geosmin, is responsible for the characteristics smell of moist soil as well as unpleasant taste and odor episodes assoiciated with public water supplies and contamination of various foodstuffs, including fish, wine and beer. Despite considerable interest in detection and remediation of methylisoborneal, the biosynthesis of this methylated monoterpene has been obscure. In Streptomyces coelicor, the sco7700 and sco7701 genes are shown to correspond to a two-gene operon responsible for methylisoborneol biosynthesis. Both genes have been amplified by PCR and the resulting DNA has been cloned and expressed in Escherichia coli. Incubation of recombinant SCO7701 protein, annotated as a possible C-methyltransferase, with geranyl diphosphate (1) and S-adenosylmethionine gave the previously unknown compound. (E)-2-methylgeranyl diphosphate (3). Incubation of 3 in the presence of Mg2+ with recombinant SCO7700, previously annotated only as a possible metal-binding protein or terpenoid synthase, resulted in the formation of 2-methylisoborneal (2). The steady-state kinetic parameters for both biochemical reactions have been determined. Incubation of geranyl diphosphate and S-adenosylmethionine with a mixture of both SCO7700 and SCO7701 resulted in formation of methylisoborneal (2). Cyclization of 2-methylgeranyl diphosphate (3) to methylisoborneal (2) likely involves the intermediacy of 2-methylinalyl diphosphate.

  DOI：

  10.1021/ja803639g

文献信息

• US3971830A
  申请人：——

  公开号：US3971830A

  公开（公告）日：1976-07-27
• US3971831A
  申请人：——

  公开号：US3971831A

  公开（公告）日：1976-07-27
• US4029709A
  申请人：——

  公开号：US4029709A

  公开（公告）日：1977-06-14
• US5710290A
  申请人：——

  公开号：US5710290A

  公开（公告）日：1998-01-20
• Biochemistry and Molecular Genetics of the Biosynthesis of the Earthy Odorant Methylisoborneol in <i>Streptomyces coelicolor</i>
  作者：Chieh-Mei Wang、David E. Cane

  DOI：10.1021/ja803639g

  日期：2008.7.1

  Methylisoborneol (2) is a volatile organic compound produced by a wide variety of Actinomycetes soil orgainisms, myxobacteria, and cyanobacteria. It has an unusually low odor threshold and, together with geosmin, is responsible for the characteristics smell of moist soil as well as unpleasant taste and odor episodes assoiciated with public water supplies and contamination of various foodstuffs, including fish, wine and beer. Despite considerable interest in detection and remediation of methylisoborneal, the biosynthesis of this methylated monoterpene has been obscure. In Streptomyces coelicor, the sco7700 and sco7701 genes are shown to correspond to a two-gene operon responsible for methylisoborneol biosynthesis. Both genes have been amplified by PCR and the resulting DNA has been cloned and expressed in Escherichia coli. Incubation of recombinant SCO7701 protein, annotated as a possible C-methyltransferase, with geranyl diphosphate (1) and S-adenosylmethionine gave the previously unknown compound. (E)-2-methylgeranyl diphosphate (3). Incubation of 3 in the presence of Mg2+ with recombinant SCO7700, previously annotated only as a possible metal-binding protein or terpenoid synthase, resulted in the formation of 2-methylisoborneal (2). The steady-state kinetic parameters for both biochemical reactions have been determined. Incubation of geranyl diphosphate and S-adenosylmethionine with a mixture of both SCO7700 and SCO7701 resulted in formation of methylisoborneal (2). Cyclization of 2-methylgeranyl diphosphate (3) to methylisoborneal (2) likely involves the intermediacy of 2-methylinalyl diphosphate.