T-杜松醇 | 5937-11-1

• 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
• 中文名称: T-杜松醇
• 英文名称: T-cadinol
• 英文别名: τ-cadinol；epi-α-cadinol；tau-cadinol；cedrelanol；1-epi-α-cadinol；(1S,4S,4aR,8aR)-1,6-dimethyl-4-propan-2-yl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-ol
• CAS: 5937-11-1
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: LHYHMMRYTDARSZ-XQLPTFJDSA-N

物化性质

• 熔点：
  139-140 °C
• 沸点：
  303.4±31.0 °C(Predicted)
• 密度：
  0.937±0.06 g/cm3(Predicted)
• LogP：
  4.899 (est)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 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：

  T-杜松醇 、 硼烷 、 sodium hydroxide 、 双氧水 、 三氧化铬 生成 Cadinan-4-on-9β-ol
  参考文献：
  名称：

  PROSEKOVA, T. N.;XAN, V. A.;DUBOVENKO, ZH. V.;PENTEGOVA, V. A., IZV. CO AN CCCP. CEP. XIM. N.,(1988) N 9/3, 102-109

  摘要：

  DOI：
• 作为产物：
  描述：

  异戊醛 在 聚合甲醛 、 (2R)-2-[二苯基[(三甲基硅酯)氧基]甲基]-吡咯烷 、 3,4-二羟基苯甲酸乙酯 、 diisopropylammonium trifluoroacetate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 57.33h， 生成 T-杜松醇
  参考文献：
  名称：

  Identification and determination of the absolute configuration of amorph-4-en-10β-ol, a cadinol-type sesquiterpene from the scent glands of the African reed frog Hyperolius cinnamomeoventris

  摘要：

  苇蛙（Hyperolid reed frogs）是已知的少数几个拥有腺体的无尾目动物家族之一，这些腺体能释放出用于化学交流的挥发性化合物。模式物种 Hyperolius cinnamomeoventris 的声囊上有一个腺体，能释放化学物质，并在鸣叫时发出视觉和听觉信号。以前的研究表明，腺体化合物通常是大环内酯。然而，在这项工作中，我们发现雄性特异性腺体的另一种主要成分是（10R,1S,6R,7R,10R）-吗啉-4-烯-10β-醇[(1R,4R,4aR,8aS)-4-异丙基-1,6-二甲基-1,2,3,4,4a,7,8,8a-八氢萘-1-醇]。该化合物是首次合成，其构型与植物中已知的非晶-4-烯-10β-醇相反。通过串联曼尼希/分子内 Diels-Alder 反应，使用有机催化方法进行简短合成，得到了一种卡丁醇混合物，并用于确定天然卡丁醇结构及其立体异构体。

  DOI：

  10.3762/bjoc.19.16

文献信息

• [EN] PRODUCTION OF STEVIOL GLYCOSIDES IN RECOMBINANT HOSTS<br/>[FR] PRODUCTION DE GLYCOSIDES DE STÉVIOL DANS DES HÔTES DE RECOMBINAISON
  申请人：EVOLVA SA

  公开号：WO2016120486A1

  公开（公告）日：2016-08-04

  The invention relates to recombinant microorganisms and methods for producing steviol glycosides, glycosylated ent-kaurenol, and glycosylated ent-kaurenoic acid.

  这项发明涉及重组微生物和生产叶草甙、糖基化的ent-kaurenol和糖基化的ent-kaurenoic酸的方法。
• Stereochemistry of 1,6-Germacradien-5-ol, a Constituent of the Needles of Scots Pine (Pinus sylvestris) and of the Defence Secretion from Larvae of the Pine Sawfly Neodiprion sertifer.
  作者：Ove Nordin、Erik Hedenström、Hans-Erik Högberg、Sayed A. Shiba、Inger Søtofte、Jørgen Møller、Alexander Senning、Xin-Kan Yao、Hong-Gen Wang、J. -P. Tuchagues、Mattias Ögren

  DOI：10.3891/acta.chem.scand.53-0124

  日期：——

  (-)-1,6-Germacradien-5-ol [(E, E) -1, 5-dimethyl-8-isopropylcyclodeca-1,6-dien-5-ol, I] has been isolated from the defence secretion from larvae of the pine sawfly Neodiprion sertifer and from needles of Scots pine (Pinus sylvestris). It was characterised by means of spectroscopic methods and by its optical rotation. Acid-promoted transannular cyclisation isomerised 1 to the known (-)-alpha-cadinol. (4), whereby the configuration at position 8 was established as S. The configuration at the second stereocentre, position 5, carrying the alcohol group is discussed on the basis of molecular mechanics calculations (MM2), NMR shift values, coupling constants and NOESY experiments. 1-endo-Bourbonanol (7a) and (-)-5-methoxy-1,6-germacradiene (8) were prepared from 1 and investigated by NMR spectroscopy. The evidence collected indicated that the stereoisomer isolated was (5S,8S)-1,6-germacradien-5-ol.

  (-)-1,6-葛木二烯-5-醇 [(E, E)-1,5-二甲基-8-异丙基环十二碳-1,6-二烯-5-醇，I] 已经从松梢松enso Neodiprion sertifer 的幼虫防御分泌物以及 Scots pine（Pinus sylvestris）的针叶中分离出来。该物质通过光谱方法和旋光性质进行了表征。在酸性条件下，跨环化反应使1异构化为已知的(-)-α-卡豆醇。其中，确定了位置8的构型为S。基于分子力学计算（MM2）、NMR化学位移值、偶合常数以及NOESY实验，讨论了第二个手性中心（位置5，携带醇基的羟基）的构型。1-endo-波旁醇（7a）和 (-)-5-甲氧基-1,6-葛木二烯（8）已从1制备并进行了NMR光谱分析。所收集的证据表明，分离的立体异构体是(5S,8S)-1,6-葛木二烯-5-醇。
• Natural essential oil sanitary insect pest repellent and its use
  申请人：Komai Koichiro

  公开号：US20060257441A1

  公开（公告）日：2006-11-16

  [Object] This invention provides a dispersion containing an insect pest repellent active substance, and an adhesive or bond, ink, resin pellets, a resin product, and a sheet or a film which can exhibit a long term repellent active effect by the particles carrying the dispersion. [Means for achieving the object] The invention also concerns with a natural essential oil having a sanitary pest repellent activity; a dispersion containing, as an active component, at least one of: a first fraction of copaiba oil given by silica gel column chromatography using hexane as an elution solvent, a second fraction given by silica gel column chromatography using a 4:4:1 mixture of hexane/chloroform/ethyl acetate as an elution solvent, and a third fraction given by fractionating the remnant of the second fraction using a 1:1 mixture of ethyl acetate/chloroform as an elution solvent; a dispersion thereof containing a sedimentation inhibitor, particles carrying these dispersions, and a sanitary insect pest repellent active adhesive or bond, ink, resin pellets, resin particles, resin product, sheet or film, and device containing the same.

  [目的] 本发明提供了一种含有昆虫害虫驱避活性物质的分散剂，以及粘合剂、油墨、树脂颗粒、树脂产品、以及可以通过携带分散剂的颗粒展现长期驱避活性效果的片材或膜。 [实现目的的手段] 本发明还涉及具有卫生害虫驱避活性的天然精油；一种分散剂，其包含至少一种以下活性组分：通过使用正己烷作为洗脱溶剂的硅胶柱层析给出的可帕伊巴油的第一分数，通过使用正己烷/氯仿/乙酸乙酯的4:4:1混合物作为洗脱溶剂的硅胶柱层析给出的第二分数，以及通过使用乙酸乙酯/氯仿的1:1混合物作为洗脱溶剂分馏第二分数的残留物给出的第三分数；其分散剂还包含一种沉淀抑制剂，携带这些分散剂的颗粒，以及卫生害虫驱避活性的粘合剂、油墨、树脂颗粒、树脂颗粒、树脂产品、片材或膜和包含它们的装置。
• Molecular cloning and functional analysis of a 10-epi-junenol synthase from Inula hupehensis
  作者：Jun-Bo Gou、Zhen-Qiu Li、Chang-Fu Li、Fang-Fang Chen、Shi-You Lv、Yan-Sheng Zhang

  DOI：10.1016/j.plaphy.2016.05.023

  日期：2016.9

  detected in many compositae plant species and were reported to exhibit various pharmacological activities. So far, the gene encoding junenol synthase has never been isolated. Here we report the molecular cloning and functional analysis of a 10-epi-junenol synthase from Inula hupehensis (designated IhsTPS1). IhsTPS1 converts the substrate farnesyl diphosphate into multiple sesquiterpenes with the product

  已在许多菊科植物物种中检测到了基于朱诺醇的大地甘露内酯，据报道其具有多种药理活性。迄今为止，从未分离出编码junenol合酶的基因。在这里，我们报告了来自湖南菊（Inula hupehensis）（命名为IhsTPS1）的10- Epi- junenol合酶的分子克隆和功能分析。IhsTPS1将底物法呢基二磷酸酯转化为多种倍半萜烯，其中产物10-表位-芥子醇为主要成分。IhsTPS1的转录水平与10-表柔红醇在hupehensis器官中的积累模式密切相关，支持其在体内的生化作用。
• Isolation and functional characterization of a τ-cadinol synthase, a new sesquiterpene synthase from Lavandula angustifolia
  作者：Frédéric Jullien、Sandrine Moja、Aurélie Bony、Sylvain Legrand、Cécile Petit、Tarek Benabdelkader、Kévin Poirot、Sébastien Fiorucci、Yann Guitton、Florence Nicolè、Sylvie Baudino、Jean-Louis Magnard

  DOI：10.1007/s11103-013-0131-3

  日期：2014.1

  In this paper we characterize three sTPSs: a germacrene D (LaGERDS), a (E)-β-caryophyllene (LaCARS) and a τ-cadinol synthase (LaCADS). τ-cadinol synthase is reported here for the first time and its activity was studied in several biological models including transiently or stably transformed tobacco species. Three dimensional structure models of LaCADS and Ocimum basilicum γ-cadinene synthase were built by homology modeling using the template structure of Gossypium arboreum δ-cadinene synthase. The depiction of their active site organization provides evidence of the global influence of the enzymes on the formation of τ-cadinol: instead of a unique amino-acid, the electrostatic properties and solvent accessibility of the whole active site in LaCADS may explain the stabilization of the cadinyl cation intermediate. Quantitative PCR performed from leaves and inflorescences showed two patterns of expression. LaGERDS and LaCARS were mainly expressed during early stages of flower development and, at these stages, transcript levels paralleled the accumulation of the corresponding terpene products (germacrene D and (E)-β-caryophyllene). By contrast, the expression level of LaCADS was constant in leaves and flowers. Phylogenetic analysis provided informative results on potential duplication process leading to sTPS diversification in lavender.

  本文描述了三种sTPS：一种为germacrene D（LaGERDS），一种为（E）-β-石竹烯（LaCARS），一种为τ-cadinol合成酶（LaCADS）。τ-cadinol合成酶是首次在此报道，其活性在包括瞬时或稳定转化的烟草物种在内的多个生物模型中进行了研究。LaCADS和Ocimum basilicum γ-cadinene合成酶的三维结构模型是通过同源建模构建的，使用Gossypium arboreum δ-cadinene合成酶的模板结构。对它们活性位点组织的描述提供了酶对τ-cadinol形成的全局影响的证据：LaCADS中整个活性位点的静电性质和溶剂可及性可能解释了cadinyl阳离子中间体的稳定性，而不是一种独特的氨基酸。从叶子和花序进行的定量PCR显示两种表达模式。LaGERDS和LaCARS主要在花发育的早期阶段表达，在这些阶段，转录水平与相应的萜烯产物（germacrene D和（E）-β-石竹烯）的积累平行。相比之下，LaCADS在叶子和花中的表达水平是恒定的。系统发育分析提供了关于导致薰衣草sTPS多样化的潜在复制过程的信息结果。