17,23β-エポキシ-3β-ヒドロキシベラトラマン-11-オン

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

  P201：使用前に取扱説明書を入手すること。

17,23β-エポキシ-3β-ヒドロキシベラトラマン-11-オン 価格

17,23β-エポキシ-3β-ヒドロキシベラトラマン-11-オン 化学特性,用途語,生産方法

• 外観

  白色〜わずかに薄い褐色, 結晶性粉末〜粉末

• 溶解性

  メタノールに溶ける。

• 説明

  First obtained from Veratrum grandiflorum by Wright and Luff, this alkaloid is also present in V. album. It was originally given the formula C26H3703N. 2H20, subsequently altered to that given above by Jacobs and Craig. The base crystallizes from aqueous EtOH in stellate groups of colourless prisms and has [α]_D - 147° (EtOH). The hydrochloride (dihydrate) has m.p. 208°C (Wright and Luff) or 330-334°C (dec.) according to Jacobs and Craig, the latter finding a change in crystalline form at 280°C. The hydriodide has m.p. 302-5°C; the nitrate and aurichloride are both crystalline and the picrate melts at 278-284°C. TheN-nitroso derivative has m.p. 246-7°C; the N-acety1 compound, m.p. 161-2°C and the O,N-diacetyl derivative, m.p. 17 6-7°C.
  Treatment with aluminium tert-butoxide gives Δ4-jervone, m.p. 193-4°C; [α]²⁸_D + 28.3° (EtOH), giving an oxime, m.p. 287-9°C and reduced by aluminium isopropoxide to Δ4-jervine, m.p. 203- 2 11°C. Catalytic hydrogenation with Pd-C yields the dihydro derivative, m.p. 248-251°C; [α]²⁶_D - 82° (EtOH). On further hydrogenation, the tetrahydro compound is formed, m.p. 216- 221°C; [α]²⁸_D - 18° (EtOH). Jervine may be reduced by sodium in butanol to a:-dihydrojervinol, m.p. 223-5°C; [α]²⁷_D - 107° (EtOH). The similar reduction of dihydrojervine yields (3-dihydrojervino1, m.p. 286-9°C; [α]²⁸_D-4 C(EtOH). On Se dehydrogenation, the alkaloid behaves like cevine (q.v.) giving a mixture of bases and hydrocarbons from which the following have been isolated; 5-methyl- 2-ethylpyridine; 5-methyl-2-ethyl-3-hydroxypyridine; C2oH22 , m.p. 79°C; C24H30, m.p. 100- 1°C; C2l H24 , m.p. 70-8 1°C; C2oH 16 , m.p. I 25-7°C and C22H20 , m.p. I 54-5℃。
  In large doses, the alkaloid produces vasodilatation and a fall in blood pressure

• 化学的特性

  White Crystalline Solid

• 使用

  Has antibacterial properties. Jervine demonstrates teratogenic properties. It is the starting material for C-nor-D-homosteroids. Jervine induces holoprosencephaly and blocks endogenous Sonic hedgehog signaling

• 純化方法

  4 Crystallise Jervine from MeOH/H2O or Me2O. The hydrochloride has m 300-302o (from MeOH/Et2O), and the picrate has m 26

• 参考文献

  Wright, Luff., J. Chern. Soc., 35,405 (1879)
  Saltzberger., Arch. Pharrn., 228,462 (1890)
  Bredemann., Apoth. Zeit., 21,41,53 (1906)
  Saito, Suginome, Takaoka., Bull. Chern. Soc. Japan, 9, 15(1934)
  Saito, Suginome, Takaoka., ibid, 11, 168, 172 (I936)
  Poethke., Arch. Pharrn., 357,571 (I937)
  Poethke., ibid, 276, 170 (1938)
  Jacobs, Craig., J. BioI. Chern., 148, 51 (1943)
  Seiferle.,J. Econ. Entorn., 35,35 (1942)
  Jacobs et al., J. Bioi. Chern., 170, 635 (1947)
  Wintersteiner et al., J. A mer. Chern. Soc., 73, 2970 (1951)
  Wintersteiner, Hosansky., ibid, 74,4474 (1952)
  Stereochemistry:
  Kupchan, Suffness., J. A mer. Chern. Soc., 90, 2730 (1968)
  Masamune et al., Tetrahedron, 24, 3461 (1968)

17,23β-エポキシ-3β-ヒドロキシベラトラマン-11-オン 生産企業

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