14,15,16,17-テトラデヒドロベラトラマン-3β,23β-ジオール

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Danger

• 危険有害性情報

  H301：飲み込むと有毒

• 注意書き

  P264：取扱い後は皮膚をよく洗うこと。

  P264：取扱い後は手や顔をよく洗うこと。

  P270：この製品を使用する時に、飲食または喫煙をしないこ と。

  P405：施錠して保管すること。

14,15,16,17-テトラデヒドロベラトラマン-3β,23β-ジオール 価格

14,15,16,17-テトラデヒドロベラトラマン-3β,23β-ジオール 化学特性,用途語,生産方法

• 外観

  白色～わずかにうすい褐色、結晶～粉末

• 溶解性

  メタノールに溶ける。

• 説明

  This alkaloid occurs naturally in Veratrum grandi/lorum and V. viride and is also formed during the hydrolysis of Veratrosine (q.v.). It forms colourless crystals of the monohydrate from aqueous EtOH and has [α]¹⁹_D - 70° (MeOH). The hydrochloride forms colourless plates from EtOH, m.p. 20l-2°C and the picrate, yellow plates, m.p. 217.5 - 218°C. Two non-phenolic hydroxyl groups and an imino group are present and the triacetyl derivative, m.p. 205.5-206°C; [α]^14.5_D + 37.8° (MeOH), on controlled hydrolysis furnishes the N-acetyl com_x0002_pound, m.p. 176-8°C. The O-acetate has also been prepared as colourless prisms from aqueous EtOH, m.p. 20l-2°C but it is still uncertain which of the hydroxyl groups is acetylated in this derivative. Treatment with methyl iodide in MeOH in the presence of sodium carbonate gives N-methylveratraminc methiodide, m.p. 268°C (dec.) from which the methochloride, m.p. 277°C can be obtained. On catalytic hydrogenation, the base furnishes the dihydro derivative, m.p. 198- 200°C; [α]²⁷_D + 27.4°, which forms the N-acetyl compound, m.p. 220-3°C; [α]²⁸_D + 81° and the triacetyl derivative, m.p. l89.5-190.5°C; [α]²⁴_D + 84°.

• 化学的特性

  White Solid

• 使用

  The hedgehog (Hh) signaling pathway, which is blocked by cyclopamine , plays a key role in morphogenesis and has potential applications in the treatment of cancer. Veratramine, a teratogenic steroidal alkaloid isolated from the corn lily (Veratrum sp.), is an analog of cyclopamine that can inhibit the Hh signaling-dependent proliferation of NIH/3T3 cells at 8 μM. Additionally, veratramine has anti-thrombotic activity as it dose dependently inhibits platelet aggregation in rabbits ex vivo. While it may be most useful as a signal transduction inhibitor for treating tumors, veratramine also induces serotonin release and inhibits its re-uptake in the CNS.

• 定義

  ChEBI: A piperidine alkaloid comprising the 14,15,16,17-tetradehydro derivative of veratraman having two hydroxy groups at the 3- and 23-positions.

• 参考文献

  Saito., Bull. Chem. Soc., Japan, 15, 22 (1940)
  Jacobs, Craig.,J. Biol. Chem., 155,565 (1944)
  Jacobs,.Craig., ibid, 160,555 (1945)
  Tamm, Wintersteiner., J. Amer. Chem. Soc., 74,3842 (1952)
  Mass spectra: Budzikiwicz., Tetrahedron, 20,2267 (1964)
  Synthesis: Masamune, Takasugi, Murai., Tetrahedron, 27,3369 (1971)

14,15,16,17-テトラデヒドロベラトラマン-3β,23β-ジオール 生産企業

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