16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol | 83790-52-7

• 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: 16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol
• 英文别名: (2E,6E,10E,14E)-16-hydroxygeranylgeraniol；16-hydroxygeranylgeraniol；2,6,10,14-tetramethyl-2,6,10,14-hexadecatetraene-1,16-diol；(2E,6E,10E,14E)-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraene-1,16-diol
• CAS: 83790-52-7
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: CLOPQFCHWDTGFD-BMTMAWCHSA-N

物化性质

• 熔点：
  29-30 °C
• 沸点：
  440.4±40.0 °C(Predicted)
• 密度：
  0.936±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol 、 乙酸酐 反应 1.0h， 生成 16-acetoxygeranyl geraniol acetate
  参考文献：
  名称：

  来自薇甘菊属植物的二聚锗烷内酯和其他倍半萜内酯

  摘要：

  摘要 对先前归入 Kanimia 属的两种薇甘菊物种的研究，除了已知化合物外，还提供了几种新的细菌。

  DOI：

  10.1016/0031-9422(82)80140-4
• 作为产物：
  描述：

  香叶基香叶醇 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 二异丁基氢化铝 、 过碘酸 作用下， 以 四氢呋喃 、 吡啶 、 水 、 乙腈 为溶剂， 反应 4.0h， 生成 16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol
  参考文献：
  名称：

  Synthesis of Plaunotol Derivatives and their Antibacterial Activities against Helicobacter pylori

  摘要：

  Plaunotol, a known antiulcer drug, has antibacterial activities against Helicobacter pylori. Plaunotol thiourea derivatives 2-4 and diol derivatives 6-10 were designed in search For a compound with high amtobacteroa; activities. Thiourea derivatives 2-4 were synthesized regioselectively using our effective synthetic route for plaunotol (1), and diol derivatives 6 10 were also synthesized. Their antibacterial activities against H. pylori are described and we found that the most potent antibacterial agent was Cl-thiourea derivative 2c. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00080-3

文献信息

• Design and synthesis of biologically active analogues of vitamin K2: Evaluation of their biological activities with cultured human cell lines
  作者：Yoshitomo Suhara、Yoshihisa Hirota、Kimie Nakagawa、Maya Kamao、Naoko Tsugawa、Toshio Okano

  DOI：10.1016/j.bmc.2007.12.025

  日期：2008.3.15

  Novel omega-oxygenated vitamin K(2) analogues were efficiently synthesized and their biological activities were evaluated. Some were biologically active and the side-chain played an important role in gamma-carboxylation and apoptosis-inducing activity. The results provide useful information on the structure-activity relationship of vitamin K(2) analogues for the development of new drugs.

  新型的ω-氧化的维生素K（2）类似物被有效地合成，并对其生物学活性进行了评估。一些具有生物活性，并且侧链在γ-羧化和诱导细胞凋亡的活性中起重要作用。结果提供了有关维生素K（2）类似物的结构-活性关系的新药开发有用的信息。
• Solid-Phase Selenium-Catalyzed Selective Allylic Chlorination of Polyprenoids:  Facile Syntheses of Biologically Active Terpenoids
  作者：Alejandro F. Barrero、José F. Quílez del Moral、M. Mar Herrador、Manuel Cortés、Pilar Arteaga、Julieta V. Catalán、Elena M. Sánchez、Jesús F. Arteaga

  DOI：10.1021/jo060760d

  日期：2006.7.1

  Regioselective halogenation of the terminal isopropylidene unit of different acyclic polyolefinic polyprenoids (farnesyl acetate, geranylgeranyl acetate, squalene, etc.) using NCS/catalytic polymer-supported selenenyl bromide is described; good to excellent yields are obtained (68−96%). The first applications of this protocol include the concise synthesis of bioactive terpenoids 1−3.

  描述了使用NCS /催化聚合物负载的亚硒基溴化物对不同的无环聚烯烃多异戊二烯酸酯（乙酸法呢酯，乙酸香叶基香叶酯，角鲨烯等）的末端异亚丙基单元进行区域选择性卤化；获得了良好至极好的产量（68-96％）。这个协议的第一应用包括生物活性类萜的简明合成1 - 3。
• Synthesis from geraniol of (2E,6E,10E,14E)-16-hydroxygeranylgeraniol and some of its derivatives
  作者：M. Grin’ko、V. Kulcitki、N. Ungur、A. Barba、K. Delyanu、P. F. Vlad

  DOI：10.1007/s10600-007-0104-3

  日期：2007.5

  Several α,ω-bifunctional derivatives of E,E,E-geranylgeraniol were prepared via convergent synthesis starting with geraniol (8), which was converted in three steps into the tetrahydropyranyl ether of 8-chlorogeraniol (9) and 8-hydroxygeranylphenylsulfone (10). Combination of synthons 9 and 10 with subsequent reductive removal of the phenylsulfonyl group produced the tetrahydropyranyl ether of ω-hydroxygeranylgeraniol (5), hydrolysis of which gave exclusively trans-ω-hydroxygeranylgeraniol (1). Derivatives 5–7 of geranylgeraniol were synthesized using standard methods.

  以香叶醇（8）为起始原料，通过收敛合成法制备了E,E,E-香叶基香叶醇的几种α,ω-双官能衍生物，香叶醇（8）通过三个步骤转化为8-氯香叶醇（9）和8-羟基香叶基苯基砜（10）的四氢吡喃基醚。将合成单元9和10组合，随后还原去除苯基砜基，得到ω-羟基香叶基香叶醇（5）的四氢吡喃基醚，水解后得到纯反式-ω-羟基香叶基香叶醇（1）。香叶基香叶醇的衍生物5-7采用标准方法合成。
• Substrate Specificities of Wild and Mutated Farnesyl Diphosphate Synthases from<i>Bacillus Stearothermophilus</i>with Artificial Substrates
  作者：Masahiko NAGAKI、Minori NAKADA、Tohru MUSASHI、Jun KAWAKAMI、Norimasa OHYA、Masayo KURIHARA、Yuji MAKI、Tokuzo NISHINO、Tanetoshi KOYAMA

  DOI：10.1271/bbb.70067

  日期：2007.7.23

  To determine the substrate specificities of wild and mutated types of farnesyl diphosphate (FPP) synthases from Bacillus stearothermophilus, we examined the reactivities of 8-hydroxygeranyl diphosphate (HOGPP) and 8-methoxygeranyl diphosphate (CH3OGPP) as allylic substrate homologs.The wild-type FPP synthase reaction of HOGPP (and CH3OGPP) with isopentenyl diphosphate (IPP) gave hydroxyfarnesyl- (and methoxyfarnesyl-) diphosphates that stopped at the first stage of condensation.On the other hand, with mutated type FPP synthase (Y81S), the former gave hydroxygeranylgeranyl diphosphate as the main double-condensation product together with hydroxyfarnesyl diphosphate as a single-condensation product and a small amount of hydroxygeranylfarnesyl diphosphate as a triple-condensation product. Moreover, the latter gave a double-condensation product, methoxygeranylgeranyl diphosphate, as the main product and only a trace of methoxyfarnesyl diphosphate was obtained.

  为了确定来自嗜热脂肪芽孢杆菌的野生型和突变型法尼基二磷酸 (FPP) 合酶的底物特异性，我们检查了 8-羟基香叶基二磷酸 (HOGPP) 和 8-甲氧基香叶基二磷酸 (CH3OGPP) 作为烯丙基底物同系物的反应性。 HOGPP（和CH3OGPP）与异戊烯基二磷酸（IPP）的FPP合酶反应产生羟基法呢基-（和甲氧基法呢基-）二磷酸，该反应在缩合的第一阶段停止。另一方面，对于突变型FPP合酶（Y81S），前者产生羟基香叶基香叶基二磷酸为主要双缩合物，羟基法尼基二磷酸为单缩合物，少量羟基香叶基法尼基二磷酸为三重缩合物。此外，后者得到双缩合产物甲氧基香叶基香叶基二磷酸酯作为主要产物，仅得到痕量的甲氧基法呢基二磷酸酯。
• Two Chemotypes of<i>Boletinus cavipes</i>
  作者：Tomonari Wada、Kenji Kobata、Yasuo Hayashi、Hisao Shibata

  DOI：10.1271/bbb.59.1036

  日期：1995.1

  Eight terpenes, including four new compounds, were isolated from Boletinus cavipes collected from two different districts (strains A and B) in Japan. Their structures were determined by spectroscopic and chemical methods, these compounds being geranylgeraniol (diterpene) or farnesoI (sesquiterpene) derivatives. The geranylgeraniol derivatives were isolated from strain A, while the farnesol derivatives were isolated from strain B. These results indicate the presence of two chemotypes of the fungus B. cavipes.

  从日本两个不同地区（菌株 A 和 B）收集的牛肝菌中分离出八种萜烯，包括四种新化合物。通过光谱和化学方法测定了它们的结构，这些化合物是香叶基香叶醇（二萜）或金合欢醇（倍半萜）衍生物。从菌株 A 中分离出香叶基香叶醇衍生物，而从菌株 B 中分离出金合欢醇衍生物。这些结果表明真菌 B. cavipes 存在两种化学型。