(S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenyl acetate | 43010-46-4

• 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: (S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenyl acetate
• 英文别名: acetylbakuchiol；Bakuchiol-acetat；4-(3,7-dimethyl-3-vinylocta-1,6-dienyl)phenyl acetate；[4-[(1E,3S)-3-ethenyl-3,7-dimethylocta-1,6-dienyl]phenyl] acetate
• CAS: 43010-46-4
• 化学式: C₂₀H₂₆O₂
• 分子量: 298.425
• InChiKey: KLWKVZWSRSGVHJ-UPTIQUDWSA-N

物化性质

• 沸点：
  413.4±24.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  补骨脂酚 、 乙酸酐 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以90.6%的产率得到(S,E)-4-(3,7-dimethyl-3-vinylocta-1,6-dien-1-yl)phenyl acetate
  参考文献：
  名称：

  补骨脂酚衍生物作为潜在抗癌剂的合成与评价。

  摘要：

  合成了一系列爆酚酚衍生物，并使用PX-478作为阳性对照评估了它们的抗增殖和对SMMC7721细胞系迁移的抑制活性。结果显示（S，E）-4-（7-甲氧基-3,7-二甲基-3-乙烯基辛-1-烯-1-基）苯酚（10）在测试的化合物中具有最佳活性，其中包括PX-478。另外，在每种剂量下，在transwell迁移和侵袭试验中，化合物10的抑制活性均比补骨脂酚高。在蛋白质印迹试验中，化合物10显示出有希望的下调HIF-1α及其相关下游蛋白MMP-2和MMP-9表达的能力。而且，该作用是剂量依赖性的，并且可能代表化合物10的抗癌活性的可能作用机理。

  DOI：

  10.3390/molecules23030515

文献信息

• Meroterpenoids—I
  作者：G. Mehta、U.R. Nayak、Sukh Dev

  DOI：10.1016/0040-4020(73)80071-7

  日期：1973.1

  Isolation and structure elucidation of a novel monoterpene phenol, bakuchiol, from the seeds of Psoralea corylifolia Linn, is described.

  描述了一种新的单萜酚，补骨脂酚，从补骨脂（Psoralea corylifolia Linn）的种子中分离和结构解析。
• Hypoxia-inducible factor-1 and nuclear factor-κB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia
  作者：Cheng-Zhu Wu、Seong Su Hong、Xing Fu Cai、Nguyen Tien Dat、Ji-Xing Nan、Bang Yeon Hwang、Jung Joon Lee、Dongho Lee

  DOI：10.1016/j.bmcl.2008.03.028

  日期：2008.4

  Two new meroterpenoids, 12,13-dihydro-12,13-dihydroxybakuchiol (2) and (12'S)-bisbakuchiol C (3), were isolated from the seeds of Psoralea corylifolia L. (Fabaceae). The structures of 2 and 3 were elucidated by spectroscopic and chemical methods. Six meroterpenoids isolated from P. corylifolia and three semi-synthetic analogues were evaluated for HIF-1 and NF-kappaB inhibition, and O-methyl and O-ethylbakuchiols

  从Psoralea corylifolia L.（Fabaceae）的种子中分离出了两个新的金属萜类化合物，12,13-dihydro-12,13-dihydroxybakuchiol（2）和（12'S）-bisbakuchiol C（3）。通过光谱和化学方法阐明了2和3的结构。评估了六株分离自紫苏的甲氧萜类化合物和三个半合成类似物的HIF-1和NF-kappaB抑制作用，O-甲基和O-乙基爆酚（6和7）抑制了HIF-1和NF-kappaB活化而没有明显降低AGS和HeLa细胞的活力。
• Bakuchiol derivatives as novel and potent cytotoxic agents: A report
  作者：Rabiya Majeed、Mallepally V. Reddy、Praveen K. Chinthakindi、Payare L. Sangwan、Abid Hamid、Gousia Chashoo、Ajit K. Saxena、Surrinder Koul

  DOI：10.1016/j.ejmech.2011.12.018

  日期：2012.3

  A library of 28 compounds comprising of acyl, amino, halo, nitro, styryl and cyclized derivatives of bakuchiol have been evaluated against a panel of eight human cancer cell lines. Bioevaluation studies have resulted in the identification of potent cytotoxic molecules exhibiting concentration dependent growth inhibition against leukemia cancer cells with best results observed for compounds 17 and 22 exhibiting IC50 1.8 and 2.0 mu M respectively. As evident from various biological end-points, inhibition of cell proliferation by inducing G2/M cell cycle arrest, mitochondrial membrane disruption followed by DNA fragmentation and apoptosis is demonstrated. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Novel bisstyryl derivatives of bakuchiol: Targeting oral cavity pathogens
  作者：Mallepally V. Reddy、Niranjan Thota、Payare L. Sangwan、Pankaj Malhotra、Furqan Ali、Inshad A. Khan、Swapandeep S. Chimni、Surrinder Koul

  DOI：10.1016/j.ejmech.2010.03.049

  日期：2010.7

  Novel bisstyryl derivatives of bakuchiol using Heck coupling reaction as the key step were synthesized and screened against a panel of six oral cavity pathogens for their antimicrobial activity. Four compounds (9-12) showed two to fourfold and four to eightfold better activity (MIC 0.25-16 mu g/ml) than bakuchiol and triclosan respectively. These compounds effectively inhibit the biofilm formation of single and multiple species at 2 - 8 x MICs. 4- and 4'-Hydroxy/methoxy styryl moieties of the bakuchiol derivatives play a pivotal role towards the activity as established in the SAR studies. Mechanism of action studies revealed microbial membrane structure disruption as the probable mode of action of these compounds. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis and Evaluation of Bakuchiol Derivatives as Potential Anticancer Agents
  作者：Cheng-Zhu Wu、Da-Chuan Liu、Xing Guo、Yiqun Dai、Tao Ma、Hong-Mei Li、Qiang Huo

  DOI：10.3390/molecules23030515

  日期：——

  A series of bakuchiol derivatives were synthesized and evaluated for their anti-proliferative and the inhibitory activities on SMMC7721 cell line migration using PX-478 as a positive control. The results showed (S,E)-4-(7-methoxy-3,7-dimethyl-3-vinyloct-1-en-1-yl)phenol (10) to have the best activity among the tested compounds, which included PX-478. In addition, compound 10 showed greater inhibitory

  合成了一系列爆酚酚衍生物，并使用PX-478作为阳性对照评估了它们的抗增殖和对SMMC7721细胞系迁移的抑制活性。结果显示（S，E）-4-（7-甲氧基-3,7-二甲基-3-乙烯基辛-1-烯-1-基）苯酚（10）在测试的化合物中具有最佳活性，其中包括PX-478。另外，在每种剂量下，在transwell迁移和侵袭试验中，化合物10的抑制活性均比补骨脂酚高。在蛋白质印迹试验中，化合物10显示出有希望的下调HIF-1α及其相关下游蛋白MMP-2和MMP-9表达的能力。而且，该作用是剂量依赖性的，并且可能代表化合物10的抗癌活性的可能作用机理。