2,3,7,8,16,17-hexahydrobakuchiol | 10309-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,3,7,8,16,17-hexahydrobakuchiol
• 英文别名: Hexahydrobakuchiol；4-(3-ethyl-3,7-dimethyloctyl)phenol；4-[(3R)-3-ethyl-3,7-dimethyloctyl]phenol
• CAS: 10309-38-3
• 化学式: C₁₈H₃₀O
• 分子量: 262.436
• InChiKey: WTLVMEPXYONHDA-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3,7,8,16,17-hexahydrobakuchiol 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 2.0h， 以96%的产率得到2,6-dibromo-4-(3-ethyl-3,7-dimethyloctyl)phenol
  参考文献：
  名称：

  Bakuchiol derivatives as novel and potent cytotoxic agents: A report

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.12.018
• 作为产物：
  描述：

  补骨脂酚 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 2,3,7,8,16,17-hexahydrobakuchiol
  参考文献：
  名称：

  类萜-I：补骨脂（Psoralea corylifolia Linn。）-1。爆酚，新型单萜酚

  摘要：

  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。

  DOI：

  10.1016/0040-4020(73)80071-7

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。
• Products active on arthropod. II. Insect juvenile hormone mimics. 2. Insect juvenile hormone mimics based on bakuchiol.
  作者：Purshotam BHAN、R. SOMAN、Sukh DEV

  DOI：10.1271/bbb1961.44.1483

  日期：——

  Several derivatives of bakuchiol, a meroterpenoid from Psoralea corylifolia Linn., have been prepared and evaluated for insect juvenile hormone activity against Dysdercus koenigii nymphs. Almost all of these were found to be more active than the standard farnesyl methyl ether, while some of these proved to be many times more potent.

  我们制备并评估了几种从榛子中提取的经皮甾醇的衍生物，这些衍生物对雏菊若虫具有昆虫幼虫激素活性。结果发现，几乎所有这些物质的活性都高于标准的法尼基甲基醚，而其中一些物质的活性更是法尼基甲基醚的数倍。
• 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.
• Anti-proliferative evaluation of monoterpene derivatives against leukemia
  作者：Lekh Nath Gautam、Taotao Ling、Walter Lang、Fatima Rivas

  DOI：10.1016/j.ejmech.2016.02.034

  日期：2016.5

  The cure rate of pediatric acute lymphoblastic leukemia (ALL) has significantly improved in the past thirty years, however not all patient cohorts respond well to current chemotherapy regimens. Among the high risk patient cohort is infants with MLL-rearranged (MLL-r) B-ALL, which remains dismal with an overall survival rate <35%. Our program is interested in identifying new molecular scaffolds to better understand the underlying mechanisms and ultimately provide new targeted treatments. Based on a phenotypic screen, phenolic natural products were identified as promising scaffolds for further chemical evaluation. Herein we disclose the effects of a potent anti-proliferative compound 31 against human ALL leukemia cellular models. (C) 2016 Elsevier Masson SAS. All rights reserved.
• 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.