dehydrovomifoliol | 15764-81-5

• 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: dehydrovomifoliol
• 英文别名: 4-keto-1-hydroxy-α-ionone；6-hydroxy-3-oxo-α-ionone；dl-dehydrovomifoliol；dl-Dehydroromifoliol；4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one；4-hydroxy-3,5,5-trimethyl-4-[(E)-3-oxobut-1-enyl]cyclohex-2-en-1-one
• CAS: 15764-81-5
• 化学式: C₁₃H₁₈O₃
• 分子量: 222.284
• InChiKey: JJRYPZMXNLLZFH-AATRIKPKSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  367.4±42.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)
• 保留指数：
  1729;1760;1757
• 稳定性/保质期：
  存在于烟叶中。

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  dehydrovomifoliol 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 4-羟基-4-(3-羟基丁-1-烯基)-3,5,5-三甲基环己-2-烯-1-酮
  参考文献：
  名称：

  脱落酸的代谢：细菌转化为脱氢伏米叶醇和伏米叶醇脱氢酶活性

  摘要：

  摘要 从土壤中分离到了一种能够代谢脱落酸（ABA）的棒状杆菌。该生物体将 ABA 转化为脱氢伏米叶醇 [(±)-1'-hydroxy-4'-keto-α-ionone] 作为主要代谢物。无细胞提取物表现出呕吐叶醇脱氢酶活性。这表明伏米叶醇很可能是脱氢伏米叶醇的直接前体。

  DOI：

  10.1016/0031-9422(84)83012-5
• 作为产物：
  描述：

  (2Z,4E)-5-(1-Hydroxy-2,6,6-trimethyl-4-oxo-cyclohex-2-enyl)-3-methyl-penta-2,4-dienoyl azide 在 potassium phosphate buffer 作用下， 以 水 为溶剂， 生成 dehydrovomifoliol
  参考文献：
  名称：

  Synthesis and properties of C-1-azido-aba

  摘要：

  The acyl azido derivative of ABA has been synthesized in high yield via a mixed anhydride. It is stable in most organic solvents but rearranges in water (t1/2 of 30 min at 30-degrees) to yield 1'-hydroxy-4'-oxo-alpha-ionone, presumably via an isocyanate intermediate. Photolysis of (+/-) RS-[G-H-3]azido-ABA in a 1% solution of bovine serum albumin with low intensity UV254nm. light gave labelled bovine serum albumin (BSA). Racemic 1-azido-ABA inhibited wheat embryo growth with about 10% the efficacy of racemic ABA. Racemic 1-azido-ABA was resolved into its enantiomers on a chiralcel HPLC column and both enantiomers were bioassayed. The (+)S-enantiomer caused stomatal closure and inhibited growth of Lemna gibba with about 10% of the potency of ABA but the (-) R-enantiomer was inactive in both the stomatal closure and Lemna gibba bioassays. It is suggested that in one of the two canonical forms of the azide the alpha-nitrogen atom carries the negative charge in the same position as the carboxyl group of ABA and so is able to substitute for it

  DOI：

  10.1016/0031-9422(93)85222-d

文献信息

• Dual Nickel/Ruthenium Strategy for Photoinduced Decarboxylative Cross-Coupling of α,β-Unsaturated Carboxylic Acids with Cycloketone Oxime Esters
  作者：Xiao-Yu Lu、Ze-Jie Xia、Ang Gao、Qi-Le Liu、Run-Chuang Jiang、Chuang-Chuang Liu

  DOI：10.1021/acs.joc.1c00726

  日期：2021.7.2

  Herein, a dual nickel/ruthenium strategy is developed for photoinduced decarboxylative cross-coupling between α,β-unsaturated carboxylic acids and cycloketone oxime esters. The reaction mechanism is distinct from previous photoinduced decarboxylation of α,β-unsaturated carboxylic acids. This reaction might proceed through a nickelacyclopropane intermediate. The C(sp2)–C(sp3) bond constructed by the

  在此，开发了一种镍/钌双策略用于 α,β-不饱和羧酸和环酮肟酯之间的光诱导脱羧交叉偶联。反应机理不同于先前的光诱导α,β-不饱和羧酸脱羧。该反应可能通过环丙烷镍中间体进行。通过上述反应构建的 C(sp 2 )–C(sp 3 ) 键为在温和的反应条件下获得各种氰基烷基烯烃提供了一种有效的方法，它们是有机和药物化学中具有合成价值的有机骨架。该协议容忍许多关键功能组，并为复杂有机分子的修饰提供了途径。
• Photochemische Reaktionen 122. Mitteilung [1]. Zur vinylogen ?-spaltung von epoxy-enonen: Photoisomerisierung des 3,4:5,6-diepoxy-5,6-dihydro-?-jonons
  作者：Norbert Bischofberger、Guy De Weck、Bruno Frei、Hans Richard Wolf、Oskar Jeger

  DOI：10.1002/hlca.19810640606

  日期：1981.9.23

  Vinylogous β-Cleavage of Epoxy-enones: Photoisomerization of 3,4: 5,6-Diepoxy-5,6-dihydro-β-ionone

  环氧烯类化合物的乙烯基β裂解：3,4：5,6-二环氧-5,6-二氢-β-紫罗兰酮的光异构化
• Metabolism of abscisic acid: Bacterial conversion to dehydrovomifoliol and vomifoliol dehydrogenase activity
  作者：Shin Hasegawa、Stephen M. Poling、V.P. Maier、Raymond D. Bennett

  DOI：10.1016/0031-9422(84)83012-5

  日期：1984.1

  species of Corynebacterium , capable of metabolizing abscisic acid (ABA), was isolated from soil. The organism converted ABA to dehydrovomifoliol [(±)-1′-hydroxy-4′-keto-α-ionone] as the major metabolise. A cell-free extract exhibited vomifoliol dehydrogenase activity. This suggests that vomifoliol is most likely the immediate precursor of dehydrovomifoliol.

  摘要 从土壤中分离到了一种能够代谢脱落酸（ABA）的棒状杆菌。该生物体将 ABA 转化为脱氢伏米叶醇 [(±)-1'-hydroxy-4'-keto-α-ionone] 作为主要代谢物。无细胞提取物表现出呕吐叶醇脱氢酶活性。这表明伏米叶醇很可能是脱氢伏米叶醇的直接前体。
• Preparation of (±)-[1,2-13C2]Abscisic Acid for Use as a Stable and Pure Internal Standard
  作者：Tadao Asami、Katsuhiko Sekimata、Jing Ming Wang、Koichi Yoneyama、Yasutomo Takeuchi、Shigeo Yoshida

  DOI：10.1039/a904712c

  日期：——

  [1,2-13C2]ABA, which is designed as a stable and pure internal standard for GC/MS analysis, is synthesized through the Witting reaction of 1-hydroxy-4-keto-α-ionone with carbomethoxymethylenetriphenylphosphorane prepared from [1,2-13C2]bromoacetic acid followed by saponification of the product methyl [1,2-13C2]ABA.

  1-hydroxy-4-keto-α-ionone 与由 [1,2-13C2]bromoacetic acid 制备的碳甲氧基亚甲基三苯基膦发生 Witting 反应，然后对产物 [1,2-13C2]ABA 甲基进行皂化，从而合成了 [1,2-13C2]ABA。
• Method and compositions for treating dystrophies and myotonia
  申请人：Nexien Biopharma, Inc.

  公开号：US10702495B2

  公开（公告）日：2020-07-07

  Methods and compositions for treating myotonia and dystrophies.

  治疗肌张力障碍和肌营养不良症的方法和组合物。

表征谱图