5-(methanesulfinyl)pentanenitrile | 61121-66-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 亚砜
• 英文名称: 5-(methanesulfinyl)pentanenitrile
• 英文别名: 5-(methylsulfinyl)-pentanenitrile；5-(methylsulfinyl)pentanenitrile；5-methylsulfinylpentanenitrile；sulforaphane nitrile；SFN-nitrile；Pentanenitrile, 5-(methylsulfinyl)-
• CAS: 61121-66-2
• 化学式: C₆H₁₁NOS
• 分子量: 145.225
• InChiKey: FGYQUFZANKOISC-UHFFFAOYSA-N

物化性质

• 沸点：
  368.3±25.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)
• 保留指数：
  1520

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  60.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-溴戊腈 在 硫酸 、 双氧水 作用下， 以 甲醇 、 水 、 异丙醇 为溶剂， 反应 10.0h， 生成 5-(methanesulfinyl)pentanenitrile
  参考文献：
  名称：

  分析和抗幽门螺杆菌萝卜硫素的活动和相关化合物目前在西兰花（甘蓝L.）豆芽

  摘要：

  从新鲜西兰花芽中制得的粗甲醇提取物依次用己烷，氯仿，乙酸乙酯和丁醇提取。从残余水层获得残余水部分。幽门螺杆菌有最大的抑制区（> 5 cm）依次用氯仿萃取液，己烷萃取液（5.03 cm），乙酸乙酯萃取液（4.90 cm），丁醇萃取液（3.10 cm）和粗甲醇萃取液（2.80 cm）显示任何抑制区。包括萝卜硫烷在内，在氯仿提取物中鉴定出了五种与萝卜硫烷相关的化合物，其中5-甲基亚磺酰基戊基腈的浓度最高（新鲜芽苗为475.7 mg / kg），其次是萝卜硫烷（222.6 mg / kg）和4-甲基亚磺酰基丁基腈。 （63.0 mg / kg）。在合成的18种萝卜硫烷和相关化合物（6种胺，6种异硫氰酸盐和6个腈）中，有2种胺，6种异硫氰酸盐和1个腈对幽门螺杆菌的抑制区大于5厘米拉紧。结果表明，西兰花芽可以作为药用物质的极佳食物来源。

  DOI：

  10.1021/jf1003573

文献信息

• The Arabidopsis Epithiospecifier Protein Promotes the Hydrolysis of Glucosinolates to Nitriles and Influences <i>Trichoplusia ni</i> Herbivory
  作者：Virginia Lambrix、Michael Reichelt、Thomas Mitchell-Olds、Daniel J. Kliebenstein、Jonathan Gershenzon

  DOI：10.1105/tpc.010261

  日期：2001.12

  Glucosinolates are anionic thioglucosides that have become one of the most frequently studied groups of defensive metabolites in plants. When tissue damage occurs, the thioglucoside linkage is hydrolyzed by enzymes known as myrosinases, resulting in the formation of a variety of products that are active against herbivores and pathogens. In an effort to learn more about the molecular genetic and biochemical regulation of glucosinolate hydrolysis product formation, we analyzed leaf samples of 122 Arabidopsis ecotypes. A distinct polymorphism was observed with all ecotypes producing primarily isothiocyanates or primarily nitriles. The ecotypes Columbia (Col) and Landsberg erecta (Ler) differed in their hydrolysis products; therefore, the Col × Ler recombinant inbred lines were used for mapping the genes controlling this polymorphism. The major quantitative trait locus (QTL) affecting nitrile versus isothiocyanate formation was found very close to a gene encoding a homolog of a Brassica napus epithiospecifier protein (ESP), which causes the formation of epithionitriles instead of isothiocyanates during glucosinolate hydrolysis in the seeds of certain Brassicaceae. The heterologously expressed Arabidopsis ESP was able to convert glucosinolates both to epithionitriles and to simple nitriles in the presence of myrosinase, and thus it was more versatile than previously described ESPs. The role of ESP in plant defense is uncertain, because the generalist herbivore Trichoplusia ni (the cabbage looper) was found to feed more readily on nitrile-producing than on isothiocyanate-producing Arabidopsis. However, isothiocyanates are frequently used as recognition cues by specialist herbivores, and so the formation of nitriles instead of isothiocyanates may allow Arabidopsis to be less apparent to specialists.

  硫代葡萄糖苷是阴离子硫代葡萄糖苷，已成为植物防御代谢物中最常被研究的类别之一。当组织受损时，硫代葡萄糖苷键会被一种名为芥子酶的酶水解，从而形成多种对食草动物和病原体具有活性的产物。为了进一步了解硫代葡萄糖苷水解产物形成的分子遗传和生化调控，我们对122种拟南芥生态型的叶片样本进行了分析。我们发现，所有生态型都表现出明显的多态性，它们主要产生异硫氰酸酯或腈。哥伦比亚（Col）和兰茨贝格直立（Ler）生态型的水解产物不同，因此，我们使用Col×Ler重组自交系来绘制控制这种多态性的基因。我们发现，影响腈和异硫氰酸酯形成的主要数量性状位点（QTL）非常接近编码油菜素内酯类同源蛋白（ESP）的基因，在某些十字花科植物的种子中，该蛋白在硫代葡萄糖苷水解过程中会导致形成表硫腈而不是异硫氰酸酯。异源表达的拟南芥ESP能够在芥子酶的作用下将硫代葡萄糖苷转化为表硫腈和简单腈，因此它比之前描述的ESP更具通用性。
• Characterisation of recombinant epithiospecifier protein and its over-expression in Arabidopsis thaliana
  作者：Marta de Torres Zabala、Murray Grant、Atle M. Bones、Richard Bennett、Yin Sze Lim、Ralph Kissen、John T. Rossiter

  DOI：10.1016/j.phytochem.2005.02.026

  日期：2005.4

  Epithiospecifier protein (ESP) is a protein that catalyses formation of epithionitriles during gluscosinolate hydrolysis. In vitro assays with a recombinant ESP showed that the formation of epithionitriles from alkenylglucosinolates is ESP and ferrous ion dependent. Nitrile formation in vitro however does not require ESP but only the presence of Fe(II) and myrosinase. Ectopic expression of ESP in Arabidopsis thaliana Col-5 under control of the strong viral CaMV 35S promoter altered the glucosinolate product profile from isothiocyanates towards the corresponding nitriles. (c) 2005 Elsevier Ltd. All rights reserved.
• Isothiocyanate containing Brassicaceae Products and Method of Preparation Thereof
  申请人：Commonwealth Scientific and Industrial Research Organisation

  公开号：US20200255872A1

  公开（公告）日：2020-08-13

  The present invention relates to methods for producing isothiocyanate containing products from Brassicaceae material and lactic acid bacteria for use in such methods. The present invention also relates to isothiocyanate containing products from Brassicaceae material produced by such methods.
• [EN] SULFORAPHANE STABILIZATION<br/>[FR] STABILISATION DU SULFORAPHANE
  申请人：AURIGA INTERNAT

  公开号：WO2012010587A1

  公开（公告）日：2012-01-26

  Composition galénique stable d'un composé de formule générale (I) dans laquelle R1 et R2 représentent tous deux, indépendamment l'un de l'autre, un groupe alkyle, aryle, arylalkyle, éventuellement substitué par un ou plusieurs groupements linéaires ou ramifiés, éventuellement cycliques, portant éventuellement un ou plusieurs hétéroatomes, Formula (I) comprenant ledit composé de formule (I) dans une quantité allant de 0,01% à 15% en poids par rapport au poids total de la composition - au moins un ester anhydre dont la chaîne principale et/ou éventuellement les chaînes ramifiées sont exemptes de groupes ou fonctions libres et/ou réactives, dans une quantité allant de 0,1 à 99,9% en poids par rapport au poids total de composition cosmétiquement et pharmaceutiquement acceptable, et - éventuellement au moins un excipient cosmétiquement et pharmaceutiquement acceptable pour compléter 100% du poids total de la composition.
• [EN] CANCER CHEMOPROTECTIVE PRODUCT COMPRISING GLUCORAPHANIN AND/OR GLUCORAPHANEN COMPOUND AND MYROSINASE ENZYME FROM BRASSICACEAE PLANT SOURCES<br/>[FR] PRODUIT CHIMIO-PROTECTEUR ANTICANCÉREUX COMPRENANT UN COMPOSÉ DE GLUCORAPHANINE ET/OU GLUCORAPHANÈNE ET UNE ENZYME MYROSINASE DÉRIVÉ DE SOURCES VÉGÉTALE DE LA FAMILLE DES BRASSICACÉES
  申请人：COMVITA NEW ZEALAND LTD

  公开号：WO2012074412A1

  公开（公告）日：2012-06-07

  A composition is described for the delivery of known and measurable quantity of agents derived from glucoraphanin and/or glucoraphanen used to induce in-vivo production of chemoprotective compounds. The composition comprises an extract from a first brassicaceae plant source comprising at least one glucosinolate compound (such as glucoraphanin and/or glucoraphanen) along with a myrosinase enzyme derived from a second brassicaceae plant source. The composition can be used in capsules or in foods such as biscuits, muesli bars or cereals to induce in-vivo production of chemoprotective agents.