(-)-β-curcumene | 28976-67-2

• 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: (-)-β-curcumene
• 英文别名: β-Curcumene；γ-curcumene；beta-curcumene；(-)-β-Curcumen；L-β-Curcumen；(-)-beta-Curcumene；1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,4-diene
• CAS: 28976-67-2
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: JXZQZARENYGJMK-CQSZACIVSA-N

物化性质

• 沸点：
  128-130 °C(Press: 6 Torr)
• 密度：
  0.8810 g/cm3(Temp: 30 °C)
• LogP：
  6.550 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 海关编码：
  2902199090

反应信息

• 作为反应物：
  描述：

  (-)-β-curcumene 在 selenium 作用下， 生成 alpha-姜黄烯
  参考文献：
  名称：

  Terpenes and sesquiterpenes of Chamaecyparis nootkatensis leaf oil

  摘要：

  DOI：

  10.1016/s0031-9422(00)85326-1
• 作为产物：
  描述：

  2-cis,6-trans-Farnesyl diphosphate(3-) 生成 (-)-β-curcumene 、 pyrophosphoric acid
  参考文献：
  名称：

  来自烟草 5-Epi-马兜铃烯合酶催化的 (2Z,6E)-法呢基二磷酸环化反应的红没药基衍生倍半萜烯

  摘要：

  我们报告了由烟草 5-epi-马兜铃烯合酶 (TEAS) 有效催化的前所未有的 1,6-环化（cisoid 途径）产生的七种红没药酰基衍生倍半萜的结构和立体化学。使用 (2Z,6E)-法呢基二磷酸作为重组 TEAS 的替代底物导致强烈的酶促环化作用，生成一系列完全 (>/=99.5%) 来自 cisoid 途径的产物，而这些相同的产物占约. 使用 (2E,6E)-法呢基二磷酸获得的总烃的 2.5%。除了无环烯丙醇 (2Z,6E)-法呢醇 (6.7%) 和橙花醇 (3.6%)、五种环状倍半萜烃和两种环状倍半萜醇外，对 2Z,6E 底物的制备培养提取物进行色谱分离： (+)-2-epi-prezizaene (44%), (-)-α-雪松烯 (21.5%)、(R)-(-)-β-姜黄烯 (15.5%)、α-acoradiene (3.9%)、4-epi-alpha-acoradiene (1.3%)

  DOI：

  10.1021/ja909886q

文献信息

• Structural Elucidation of Cisoid and Transoid Cyclization Pathways of a Sesquiterpene Synthase Using 2-Fluorofarnesyl Diphosphates
  作者：Joseph P. Noel、Nikki Dellas、Juan A. Faraldos、Marylin Zhao、B. Andes Hess、Lidia Smentek、Robert M. Coates、Paul E. O’Maille

  DOI：10.1021/cb900295g

  日期：2010.4.16

  Sesquiterpene skeletal complexity in nature originates from the enzyme catalyzed ionization of (trans,trans)-farnesyl diphosphate (FPP) (1a) and subsequent cyclization along either 2,3-transold or 2,3-cisoid farnesyl cation pathways. Tobacco 5-epi-aristolochene synthase (TEAS), a transoid synthase, produces cisoid products as a component of its minor product spectrum. To investigate the cryptic cisoid cyclization pathway in TEAS, we employed (cis,trans)-FPP (1b) as an alternative substrate. Strikingly, TEAS was catalytically robust in the enzymatic conversion of (cis,trans)-FPP (1b) to exclusively (>= 99.5%) cisoid products. Further, crystallographic characterization of wild-type TEAS and a catalytically promiscuous mutant (M4 TEAS) with 2-fluoro analogues of both all-trans FPP (1a) and (cis,trans)-FPP (1b) revealed binding modes consistent with preorganization of the farnesyl chain These results provide a structural glimpse into both cisoid and transoid,cyclization pathways efficiently templated by a single enzyme active site, consistent with the recently elucidated stereochemistry of the cisoid products. Further, computational studies using density functional theory calculations reveal concerted highly asynchronous cyclization pathways leading to the major cisoid cyclization products. The implications of these discoveries for expanded sesquiterpene diversity in nature are discussed.
• (+)-Bisabola-2,10-diene[1,9]oxide, a constituent of the liverwort Calypogeia suecica
  作者：Ute Warmers、Angela Rieck、Wilfried A König、Hermann Muhle

  DOI：10.1016/s0031-9422(99)00081-3

  日期：1999.7

  The sesquiterpene constituents of the liverwort Calypogeia suecica (Arn. and Perss.) K. Mull. were investigated. In addition to many known compounds a new sesquiterpene oxide, (+)-bisabola-2,10-diene[1,9]oxide, could be isolated and identified. The structure elucidation was carried out by NMR spectroscopic techniques and chemical conversions. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Terpenes and sesquiterpenes of Chamaecyparis nootkatensis leaf oil
  作者：Niels H. Andersen、Daniel D. Syrdal

  DOI：10.1016/s0031-9422(00)85326-1

  日期：1970.6
• Bisabolyl-Derived Sesquiterpenes from Tobacco 5-Epi-aristolochene Synthase-Catalyzed Cyclization of (2<i>Z</i>,6<i>E</i>)-Farnesyl Diphosphate
  作者：Juan A. Faraldos、Paul E. O’Maille、Nikki Dellas、Joseph P. Noel、Robert M. Coates

  DOI：10.1021/ja909886q

  日期：2010.3.31

  acyclic allylic alcohols (2Z,6E)-farnesol (6.7%) and nerolidol (3.6%), five cyclic sesquiterpene hydrocarbons and two cyclic sesquiterpene alcohols: (+)-2-epi-prezizaene (44%), (-)-alpha-cedrene (21.5%), (R)-(-)-beta-curcumene (15.5%), alpha-acoradiene (3.9%), 4-epi-alpha-acoradiene (1.3%), and equal amounts of alpha-bisabolol (1.8%) and epi-alpha-bisalolol (1.8%). The structures, stereochemistry, and

  我们报告了由烟草 5-epi-马兜铃烯合酶 (TEAS) 有效催化的前所未有的 1,6-环化（cisoid 途径）产生的七种红没药酰基衍生倍半萜的结构和立体化学。使用 (2Z,6E)-法呢基二磷酸作为重组 TEAS 的替代底物导致强烈的酶促环化作用，生成一系列完全 (>/=99.5%) 来自 cisoid 途径的产物，而这些相同的产物占约. 使用 (2E,6E)-法呢基二磷酸获得的总烃的 2.5%。除了无环烯丙醇 (2Z,6E)-法呢醇 (6.7%) 和橙花醇 (3.6%)、五种环状倍半萜烃和两种环状倍半萜醇外，对 2Z,6E 底物的制备培养提取物进行色谱分离： (+)-2-epi-prezizaene (44%), (-)-α-雪松烯 (21.5%)、(R)-(-)-β-姜黄烯 (15.5%)、α-acoradiene (3.9%)、4-epi-alpha-acoradiene (1.3%)