β-eudesmol | 473-15-4

• 物质功能分类: 有机原料 - 醇、酚、酚醇类化合物及衍生物
• 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: β-eudesmol
• 英文别名: 2-[(2R,4aR)-4a-methyl-8-methylidene-1,2,3,4,5,6,7,8a-octahydronaphthalen-2-yl]propan-2-ol
• CAS: 473-15-4；3287-59-0；57605-77-3；60132-32-3；69686-17-5；73246-03-4；79254-43-6；92790-78-8；95529-67-2
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: BOPIMTNSYWYZOC-ILWWEHDPSA-N

物化性质

• 熔点：
  72-74 °C(lit.)
• 比旋光度：
  +55～+75°(D/20℃)(c=0.2,CHCl3)(after drying)
• 沸点：
  301.7±11.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿：微溶；甲醇：微溶
• LogP：
  4.568 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 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

安全信息

• WGK Germany：
  2
• RTECS号：
  QJ9698500
• 安全说明：
  S22,S24/25

制备方法与用途

生物活性方面，Beta-Eudesmol 是一种天然的含氧倍半萜烯，能够活化 hTRPA1，其 EC50 值为 32.5 μM。此外，Beta-Eudesmol 还可以通过激活 hTRPA1 来增加食欲。

反应信息

• 作为反应物：
  描述：

  β-eudesmol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以72.1%的产率得到
  参考文献：
  名称：

  Active compounds against tinea pedis dermatophytes fromAgeratina pichinchensisvar.bustamenta

  摘要：

  Secondary metabolites 5-acetyl-3 beta-angeloyloxy-2 beta-(1-hydroxyisopropyl)-2,3-dihydrobenzofurane (1), 5-acetyl-3 beta-angeloyloxy-2 beta-(1-hydroxyisopropyl)-6-methoxy- 2,3-dihydrobenzofurane (2), espeletone (3), encecalinol (4), O-methylencecalinol (5), encecalin (6), sonorol (7), taraxerol (8), (+)-beta-eudesmol (9), and a mixture of beta-sitosterol and stigmasterol, were isolated from the aerial parts of Ageratina pichinchensis var. bustamenta. The antimicrobial activity of compounds 6, 8 and 9, together with derivatives 9a and 9b against the most important dermatophytes responsible for tinea pedis infection, Trichophyton rubrum and T. mentagrophytes, and against Candida albicans and Aspergillus niger were determined, showing that the three natural products were active against both Trichophyton species. Ageratina pichinchensis var. bustamenta is used in folk medicine to treat skin infections and wounds, and this study confirms that the n-hexane extract contains metabolites which are responsible for these utilities.

  DOI：

  10.1080/14786410902843301
• 作为产物：
  描述：

  2-((3E,8E)-4,8-Dimethyl-cyclodeca-3,8-dienyl)-propan-2-ol 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.12h， 生成 α-eudesmol 、 β-eudesmol 、 2-[(2R,4aR)-4a,8-二甲基-2,3,4,5,6,7-六氢-1H-萘-2-基]丙-2-醇
  参考文献：
  名称：

  新庚啶的全合成。它可能在Eudesmane Sesquiterpenes的生物合成中发挥作用。

  摘要：

  从已知的二酮6开始，以十个步骤完成了新庚烷醇（4）的合成过程，即新庚烷倍半萜烯庚烷醇的C（9）-C（10）双键区域异构体。中间体甲磺酸酯14的马歇尔片段用于制备新庚烷中存在的反式，反式-环癸-1,6-二烯环。在合成14的过程中，观察到了一个贯穿键相互作用（TBI）的明显例子。在光谱学上和通过化学转化成α-，β-和γ-艾地摩尔的方式证明了新庚啶的优选的细长椅子构象。这些发现表明，如文献中所提出的，在新的表皮的合成中，新庚烷醇作为前体的出现是不可能的。新庚烷醇对细长的椅子构象的偏爱进一步表明该化合物占据内消旋形式。这意味着新庚啶醇可以作为实体和通常的阿联苯胺的生物合成中的前体。

  DOI：

  10.1021/jo962056a

文献信息

• BIORATIONAL REPELLENTS OBTAINED FROM TERPENOIDS FOR USE AGAINST ARTHROPODS
  申请人：Coats R. Joel

  公开号：US20070154504A1

  公开（公告）日：2007-07-05

  The compositions comprise an effective repellent amount of one or more monoterpenoids, one or more sesquiterpenoids or a blend of one or more monoterpenoids and one or more sesquiterpenoids in combination with a carrier, wherein the compositions are formulated to repel a target pest from a target area. In one embodiment, the one or more monoterpenoids, and/or one or more sesquiterpenoids are from a biorational source, such as a plant volatile. In one embodiment, the one or more sesquiterpenoids are oxygen-containing sesquiterpenoids. In a particular embodiment, the plant volatile is a monoterpenoid, such as “nepetalactone” (or the individual nepetalactone isomers) derived from catnip ( Nepeta cataria ). In another embodiment, the plant volatile is additionally or alternatively a sesquiterpenoid derived from the fruit of the Osage orange tree ( Maclura pomifera ), Siam wood or the Amyris plant. Such compositions have repellency, including long term repellency, against arthropods.
• COMPOSITIONS COMPRISING COMBINATIONS OF PURIFIED CANNABINOIDS, WITH AT LEAST ONE FLAVONOID, TERPENE, OR MINERAL
  申请人：Canopy Growth Corporation

  公开号：US20210220324A1

  公开（公告）日：2021-07-22

  Disclosed herein are new compositions having combinations of purified cannabinoids. One embodiment of this disclosure provides compositions having one or more purified cannabinoids in combination with a purified terpene. One embodiment of this disclosure provides compositions having one or more purified cannabinoids in combination with a purified flavonoid. One embodiment of this disclosure provides compositions having one or more purified cannabinoids in combination with a purified mineral.
• CARRIER SYSTEM FOR PREPARING HERBACEOUS EXTRACTS
  申请人：SISAF LIMITED

  公开号：US20220174952A1

  公开（公告）日：2022-06-09

  A method for stabilizing a bioactive herbaceous extract in a composition comprising silicon particles, the method comprising bringing the bioactive herbaceous extract into contact with the silicon particles, in the presence of at least one non-reducing disaccharide. Also related compositions and methods.
• US7939091B2
  申请人：——

  公开号：US7939091B2

  公开（公告）日：2011-05-10
• [EN] BIORATIONAL REPELLENTS OBTAINED FROM TERPENOIDS AND METHODS RELATED THERETO<br/>[FR] REPULSIFS BIORATIONNELS OBTENUS A PARTIR DE TERPÉNOÏDES ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：UNIV IOWA STATE RES FOUND INC

  公开号：WO2007109736A2

  公开（公告）日：2007-09-27

  [EN] The compositions comprise an effective repellent amount of one or more monoterpenoids, one or more oxygen-containing sesquiterpenoids or a blend of one or more monoterpenoids and one or more oxygen-containing sesquiterpenoids in combination with a carrier, wherein the compositions are formulated to repel a target pest from a target area. In one embodiment, the one or more monoterpenoids, and/or one or more sesquiterpenoids are from a biorational source, such as a plant volatile. Such compositions have repellency, including long-term repellency, against arthropods.
  [FR] Selon l'invention, les compositions comprennent une quantité efficace de répulsifs contenant un ou plusieurs monoterpénoïdes, un ou plusieurs sesquiterpénoïdes contenant de l'oxygène ou un mélange d'un ou plusieurs monoterpénoïdes et un ou plusieurs sesquiterpénoïdes contenant de l'oxygène associé à un vecteur, les compositions étant formulées de manière à repousser un nuisible cible d'une zone cible. Dans un mode de réalisation, le ou les monoterpénoïdes, et/ou un ou plusieurs sesquiterpénoïdes proviennent d'une source biorationnelle, telle qu'un composé volatile végétal. Lesdites compositions présentent des propriétés répulsives, notamment une répulsion à long-terme, en ce qui concerne les arthropodes.

表征谱图