methyl (2E,6E,10S)-(-)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoate | 37133-77-0

• 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 (2E,6E,10S)-(-)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoate
• 英文别名: methyl (2E,6E,10S)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoate；JH III diol；(2E,6E,10S)-10,11-dihydroxy-3,7,11-trimethyl-dodeca-2,6-dienoic acid methyl ester；S-Methyl-trans,trans-10,11-dihydroxyfarnesoat；methyl (2E,6E,10S)-10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dienoate
• CAS: 37133-77-0
• 化学式: C₁₆H₂₈O₄
• 分子量: 284.396
• InChiKey: MBJDYYPZJXVUHJ-RATZTOCSSA-N

物化性质

• 沸点：
  412.8±45.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2E,6E,10S)-(-)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoate 在 吡啶 、 potassium carbonate 、 甲基磺酰氯 作用下， 生成 保幼激素3
  参考文献：
  名称：

  Enantioselective Synthesis of Juvenile Hormone III in Three Steps from Methyl Farnesoate

  摘要：

  法诺斯酸甲酯的不对称二羟基化导致了 10、11 烯烃的区域选择性二羟基化，从而以高 ee 得到 (10S)and (10R) -(2E,6E)-10,11-dihydroxy-3,7,11-trimethyI-2,6-dodecadienoates (10S)和 (10R)。这些二元醇被转化为幼年激素 III 及其对映体。

  DOI：

  10.1055/s-1993-25939
• 作为产物：
  描述：

  methyl (S)-(-)-6,7-isopropylidenedioxy-7-methyl-2-octynoate 在 sodium hydroxide 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 sodium hydride 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 14.25h， 生成 methyl (2E,6E,10S)-(-)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoate
  参考文献：
  名称：

  Synthesis of both the enantiomers of juvenile hormone III

  摘要：

  DOI：

  10.1016/s0040-4020(01)83448-7

文献信息

• Fungal metabolism of (±)-epoxyfarnesol and its absolute stereochemistry
  作者：Yoshikatsu Suzuki、Shingo Marumo

  DOI：10.1016/s0040-4039(01)84743-2

  日期：1972.1
• Function of Phenylalanine 259 and Threonine 314 within the Substrate Binding Pocket of the Juvenile Hormone Esterase of <i>Manduca sexta</i>
  作者：Shizuo G. Kamita、Mark D. Wogulis、Christopher S. Law、Christophe Morisseau、Hiromasa Tanaka、Huazhang Huang、David K. Wilson、Bruce D. Hammock

  DOI：10.1021/bi901641x

  日期：2010.5.4

  Juvenile hormone (JH) is a key insect developmental hormone that is found at low nanomolar levels in larval insects. The methyl ester of JH is hydrolyzed in many insects by an esterase that shows high specificity for JH. We have previously determined a crystal structure of the JH esterase (JHE) of the tobacco hornworm Manditca sexta (MsJHE) [Wogulis, M., Wheelock, C. E., Kamita, S. G., Hinton, A. C., Whetstone, P. A., Hammock, B. D., and Wilson, D. K. (2006) Biochemistry 45, 4045-4057]. Our molecular modeling indicates that JH fits very tightly within the substrate binding pocket of MsJHE. This tight fit places two noncatalytic amino acid residues, Phe-259 and Thr-314, within the appropriate distance and geometry to potentially interact with the alpha,beta-unsaturated ester and epoxide, respectively, of JH. These residues are highly conserved in numerous biologically active JHEs. Kinetic analyses of mutants of Phe-259 or Thr-314 indicate that these residues contribute to the low K-M that MsJHE shows for JH. This low K-M, however, comes at the cost of reduced substrate turnover. Neither nucleophilic attack of the resonance-stabilized ester by the catalytic serine nor the availability of a water molecule for attack of the acyl-enzyme intermediate appears to be a rate-determining step in the hydrolysis of JH by MsJHE. We hypothesize that the release of the JH acid metabolite from the substrate binding pocket limits the catalytic cycle. Our findings also demonstrate that chemical bond strength does not necessarily correlate with how reactive the bond will be to metabolism.
• MORI, KENJI;MORI, HIDETO, TETRAHEDRON, 43,(1987) N 18, 4097-4106
  作者：MORI, KENJI、MORI, HIDETO

  DOI：——

  日期：——
• Enantioselective Synthesis of Juvenile Hormone III in Three Steps from Methyl Farnesoate
  作者：Gerard A. Crispino、K. Barry Sharpless

  DOI：10.1055/s-1993-25939

  日期：——

  The asymmetric dihydroxylation of methyl farnesoate resulted in regioselective dihydroxylation of the 10, 11 olefin to give the (10S)and (10R) -(2E,6E)-10,11-dihydroxy-3,7,11-trimethyI-2,6-dodecadienoates in high ee. These diols were converted to juvenile hormone III and its enantiomer.

  法诺斯酸甲酯的不对称二羟基化导致了 10、11 烯烃的区域选择性二羟基化，从而以高 ee 得到 (10S)and (10R) -(2E,6E)-10,11-dihydroxy-3,7,11-trimethyI-2,6-dodecadienoates (10S)和 (10R)。这些二元醇被转化为幼年激素 III 及其对映体。
• Synthesis of both the enantiomers of juvenile hormone III
  作者：Kenji Mori、Hideto Mori

  DOI：10.1016/s0040-4020(01)83448-7

  日期：1987.1