12-hydroxyfarnesol | 69809-46-7

• 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: 12-hydroxyfarnesol
• 英文别名: 12-Hydroxyfarnesol；(2E,6E,10E)-2,6,10-trimethyldodeca-2,6,10-triene-1,12-diol
• CAS: 69809-46-7
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: FLIKBVTXNBEPQQ-RDUMTQBOSA-N

物化性质

• 沸点：
  368.9±37.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  8
• 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

ADMET

代谢

羟基法尼醇已知的人类代谢物包括 (2S,3S,4S,5R)-3,4,5-三羟基-6-[（2E,6E,10E）-12-羟基-2,6,10-三甲基十二碳-2,6,10-三烯氧基]氧杂环己烷-2-羧酸。

Hydroxyfarnesol has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[(2E,6E,10E)-12-hydroxy-2,6,10-trimethyldodeca-2,6,10-trienoxy]oxane-2-carboxylic acid.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  12-hydroxyfarnesol 在 lipase PS-D 作用下， 反应 26.0h， 生成 E,E,E-12-hydroxyfarnesyl acetate
  参考文献：
  名称：

  Highly regioselective lipase-catalyzed acetylation and hydrolysis of acyclic α,ω-terpenediols and their diacetates

  摘要：

  Highly regioselective transformations of the acyclic alpha,omega-terpenediols and their diacetates to the monoacetates using lipase were accomplished. The acetylation of the alpha,omega-terpenediols gave regioselectively the omega-monoacetates 3, whereas the alpha-monoacetates 2 were obtained by hydrolysis of the alpha,omega-diacetates. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00626-9
• 作为产物：
  描述：

  E,E,E-12-hydroxyfarnesyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以99%的产率得到12-hydroxyfarnesol
  参考文献：
  名称：

  固相硒催化多烯丙酸酯的选择性烯丙基氯化：生物活性萜类化合物的简便合成。

  摘要：

  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。

  DOI：

  10.1021/jo060760d

文献信息

• Control of the Regio- and Diastereoselectivity for the Preparation of Highly Functionalized Terpenic Cyclopentanes through Radical Cyclization
  作者：Jesús F. Arteaga、Horacio R. Diéguez、José A. González-Delgado、José F. Quílez del Moral、Alejandro F. Barrero

  DOI：10.1002/ejoc.201100400

  日期：2011.9

  The titanocene-mediated cyclization of suitably functionalized acyclic C10 epoxy-polyprenes leads, with moderate stereoselectivity, to high yields of functionalized terpenic cyclopentanes with three contiguous stereogenic centers. These highly functionalized cyclopentanes are useful intermediates for the synthesis of several natural compounds that include this interesting subunit in their structure

  适当官能化的无环 C10 环氧-聚戊二烯的二茂钛介导的环化以中等立体选择性导致具有三个连续立体中心的官能化萜烯环戊烷的高产率。这些高度官能化的环戊烷是合成几种天然化合物的有用中间体，这些天然化合物的结构中包含这种有趣的亚基。生成环戊烷的过程的区域选择性和环化的立体选择性都可以通过使用丙二酰衍生物或 α,β-不饱和腈作为自由基受体来控制。
• Triterpenoid saponins and others glycosides from the stem barks of Pancovia turbinata Radlk
  作者：Armand Emmanuel Moffi Biang、Lin Marcellin Messi、Eutrophe Le Doux Kamto、Line Made Simo、Pierre Lavedan、Marc Vedrenne、Josephine Ngo Mbing、Dieudonné Emmanuel Pegnyemb、Mohamed Haddad、Olivier Placide Noté

  DOI：10.1016/j.carres.2021.108393

  日期：2021.10

  In our continuing search of saponins from the plant of Sapindaceae family, phytochemical investigation of the stem barks of Pancovia turbinata Radlk., led to the isolation and structural characterization of two new triterpenoid saponins, named turbinatosides A-B (1–2), one new farnesyl glycoside, named turbinoside A (3), one new coumarin glucoside, named panturboside A (4), together with a known saponin

  在我们不断寻找无患子科植物皂苷的过程中，对Pancovia turbinata Radlk. 的茎皮进行植物化学研究，分离出两种新的三萜皂苷并进行结构表征，命名为 turbinatosides AB ( 1 – 2 )，一种新的法尼基皂苷糖苷，命名为 turbinoside A ( 3 )，一种新的香豆素葡萄糖苷，命名为 panturboside A ( 4 )，以及一种已知的皂苷 ( 5 )。 利用 NMR 技术的广泛分析，主要是 1D NMR（ 1 H、 13 C 和 DEPT）和 2D NMR（COSY、NOESY、HSQC、HSQC-TOCSY 和 HMBC）实验、HRESIMS 和通过与文献数据比较，如 3- O - β - d -吡喃木糖基-(1 → 3)- α - l -吡喃阿拉伯糖基-(1 → 4)- β - d -吡喃葡萄糖基-(1 → 3)- α - l -吡喃鼠李糖基-(1
• 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。
• Biochemical and structural characterization of CYP124: A methyl-branched lipid ω-hydroxylase from <i>Mycobacterium tuberculosis</i>
  作者：Jonathan B. Johnston、Petrea M. Kells、Larissa M. Podust、Paul R. Ortiz de Montellano

  DOI：10.1073/pnas.0907398106

  日期：2009.12.8

  Mycobacterium tuberculosis ( Mtb ) produces a variety of methyl-branched lipids that serve important functions, including modulating the immune response during pathogenesis and contributing to a robust cell wall that is impermeable to many chemical agents. Here, we report characterization of Mtb CYP124 ( Rv2266 ) that includes demonstration of preferential oxidation of methyl-branched lipids. Spectrophotometric titrations and analysis of reaction products indicate that CYP124 tightly binds and hydroxylates these substrates at the chemically disfavored ω-position. We also report X-ray crystal structures of the ligand-free and phytanic acid-bound protein at a resolution of 1.5 Å and 2.1 Å, respectively, which provide structural insights into a cytochrome P450 with predominant ω-hydroxylase activity. The structures of ligand-free and substrate-bound CYP124 reveal several differences induced by substrate binding, including reorganization of the I helix and closure of the active site by elements of the F, G, and D helices that bind the substrate and exclude solvent from the hydrophobic active site cavity. The observed regiospecific catalytic activity suggests roles of CYP124 in the physiological oxidation of relevant Mtb methyl-branched lipids. The enzymatic specificity and structures reported here provide a scaffold for the design and testing of specific inhibitors of CYP124.

  结论：本研究报道了对结核分枝杆菌（Mycobacterium tuberculosis，简称Mtb）CYP124（Rv2266）的表征，包括证明其对甲基支链脂类具有优先氧化作用。光谱滴定和反应产物分析表明，CYP124紧密结合并在化学上不利的ω位点水解这些底物。本研究还报道了在分辨率为1.5Å和2.1Å的情况下，无配体和配有植酸的蛋白的X射线晶体结构，这为具有主导ω-羟化酶活性的细胞色素P450提供了结构洞察。无配体和底物结合的CYP124的结构显示，底物结合引起了I螺旋的重组，并由F、G和D螺旋的元素封闭了活性位点，这些元素结合底物并将溶剂从疏水性活性位点腔中排除。观察到的区域特异性催化活性表明CYP124在生理氧化相关Mtb甲基支链脂类中发挥作用。本文报道的酶的特异性和结构为设计和测试CYP124特定抑制剂提供了支架。
• Vig, O. P.; Sharma, M. L.; Gauba, Rita, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1985, vol. 24, p. 513 - 515
  作者：Vig, O. P.、Sharma, M. L.、Gauba, Rita、Puri, S. K.

  DOI：——

  日期：——