9,11-dehydro-β-boswellic acid | 471-65-8

• 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: 9,11-dehydro-β-boswellic acid
• 英文别名: 9,11-Dehydro-beta-boswellic acid；(3R,4R,4aR,6aS,6bR,8aR,11R,12S,12aR,14bS)-3-hydroxy-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a-dodecahydro-1H-picene-4-carboxylic acid
• CAS: 471-65-8
• 化学式: C₃₀H₄₆O₃
• 分子量: 454.693
• InChiKey: TWPITYZFXPKIQX-XRPAIOGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  beta-乳香酸 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 9,11-dehydro-β-boswellic acid
  参考文献：
  名称：

  Synthesis and Structural Proof of a Potent 5-Lipoxygenase Inhibitor

  摘要：

  C–H···O and O–H···O types of氢键相互作用。5-脂氧合酶抑制剂3-O-乙酰基-9,11-脱氢-β-乳香酸的合成和晶体结构分析。抑制剂的A、B、D和E环采用椅子构象，C环采用扭曲的半椅子构象。分子堆积通过C-H·O和O-H·O类型的氢键相互作用稳定。

  DOI：

  10.1007/s10870-010-9956-7

文献信息

• Synthesis and Structural Proof of a Potent 5-Lipoxygenase Inhibitor
  作者：Devipriya Balu、Kumaradhas Poomani、Kalyanam Nagabushanam、Sridhar Balasubramanium、Rajendran Ramanujam、Majeed Muhammed

  DOI：10.1007/s10870-010-9956-7

  日期：2011.5

  5-Lipoxygenase inhibitor 3-O-acetyl-9,11-dehydro-β-boswellic acid was detected in the extract of Boswellia serrata gum resulting from unstable 11-hydroxy precursor. It was reported more potent than other Boswellic acids in its inhibition of 5-Lipoxygenase. Here, we report the method of conversion of 3-acetoxy-β-boswellic acid to 3-O-acetyl-9,11-dehydro-β-boswellic acid, and the crystal structure of later. This compound crystallizes in orthorhombic space group P212121 with cell parameters of a = 12.726(1) Å, b = 16.597(1) Å, c = 27.332(2) Å, α = β = γ = 90°, V = 5772.7(5) Å3, D c = 1.143 Mg/m3, and Z = 8. The X-ray structure investigation indicates that the rings A, B, D and E are exhibit chair and the ring C adopts a distorted half chair conformation. The conformational difference of the two structures in the arrangement is due to crystal packing of 3-O-acetyl-9,11-dehydro-β-boswellic acid. The molecular packing is stabilized by C–H···O and O–H···O types of hydrogen bonding interactions. Synthesis and crystal structure analysis of 5-Lipoxygenase Inhibitor 3-O-acetyl-9,11-dehydro-β-boswellic acid are reported. Rings A, B, D and E of the inhibitor adopt chair conformation and the C-ring exhibit a distorted half chair conformation. The molecular packing is stabilized by C–H···O and O–H···O types of hydrogen bonding interactions.

  C–H···O and O–H···O types of氢键相互作用。5-脂氧合酶抑制剂3-O-乙酰基-9,11-脱氢-β-乳香酸的合成和晶体结构分析。抑制剂的A、B、D和E环采用椅子构象，C环采用扭曲的半椅子构象。分子堆积通过C-H·O和O-H·O类型的氢键相互作用稳定。