(13R,14R)-14,19-ジヒドロ-12,13-ジヒドロキシ-20-ノルクロタラナン-11,15-ジオン

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

  H351：発がんのおそれの疑い

• 注意書き

  P201：使用前に取扱説明書を入手すること。

(13R,14R)-14,19-ジヒドロ-12,13-ジヒドロキシ-20-ノルクロタラナン-11,15-ジオン 価格

(13R,14R)-14,19-ジヒドロ-12,13-ジヒドロキシ-20-ノルクロタラナン-11,15-ジオン 化学特性,用途語,生産方法

• 外観

  白色～わずかにうすい黄色, 結晶～粉末

• 溶解性

  エタノール及びアセトンに溶ける。

• 使用上の注意

  不活性ガス封入

• 説明

  A hepatotoxic alkaloid of the pyrrolizidine group obtained from Crotalaria retusa and C. spectabilis, the base is laevorotatory with [α]²⁶_D - 55.7° (CHCI3). It may be characterized as the hydrochloride, m.p. 184°C ldec.); [α]²⁸_D - 38.4° (H20) and the methiodide which crystallizes from MeOH with 3 moles of solvent, m.p. 205°C (dry, dec.); [α]²⁸_D + 23.4° (MeOH). Hydrolysis with boiling Ba(OHh furnishes retronecine and monocrotic acid, C7H120 3, b.p. 145-6°C/ 18 mm which is optically inactive. This acid yields a methyl ester, b.p. 94-6°Cj 18 mm, a p-bromophenacyl ester, m.p. 78°C and a 2:4-dinitrophenylhydrazone, m.p. 95-6°C. Hydrogenation in the presence of Pt02 as catalyst yields retro_x0002_necanol and monocrotalic acid, CSH120S' m.p. 181-2°C; [α]²⁸_D - 5.33° (H20) which gives a methyl ester, m.p. 79-800 C; [α]³⁰_D - 16.2° (EtOH) and a pbromophenacyl ester, m.p. 162-3°C.

• 化学的特性

  White to light tan powder

• 物理的性質

  Appearance: white prism crystal. Solubility: soluble in methanol, ethanol, and chloroform; slightly soluble in benzene, water, ether, and acetone; insoluble in petroleum ether. Melting point: 197–198 °C. Specific optical rotation: ?54.7 ° (in chloroform).

• 来歴

  In 1935, W.?M. Neil and L.?L. Russoff isolated monocrotaline from Crotalaria sessiliflora L.?Monocrotaline showed anticancer activity in?vivo, especially for treating squamous cell carcinoma, cervical cancer, and leukemia. However, since many pyrrolizidine alkaloid compounds have hepatotoxicity, further development of these compounds is restricted.
  China began the research of monocrotaline, as early as 1943. Crotalaria sessiliflora L. was also recorded in the 1977 edition of the Pharmacopoeia of the People’s Republic of China. But monocrotaline was reported for its liver toxicity; teratogenic, allergic reactions; and other side effects, limiting its further clinical applications. In 1992, the Ministry of Health stopped the clinical application of monocrotaline injection. Further pharmacology study is essential for monocrotaline .

• 使用

  A toxic pyrrolizidine alkaloid isolated from Crotalaria spp. It is used for inducing pulmonary diseases in rats.

• 適応症

  This product is available in the Pharmacopoeia of the People’s Republic of China (1977).
  Clinical available formulations include gel and liposome transdermal preparations. It is effective in treating skin cancer, basal cell carcinoma, acute leukemia, and cervical and penile cancer.

• 一般的な説明

  This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

• 薬理学

  Monocrotaline is a pyrrolizidine alkaloid which has anticancer and anti-choline effects. In vitro study suggested that monocrotaline has significant cytotoxicity in human BEL-7402, KB cancer cells through inducing DNA alkylation . Monocrotaline’s toxicity is low, but its metabolites in the liver have high liver toxicity. The metabolites are highly electrophilic and can bind to enzymes, proteins, DNA, and RNA, thus causing several side effects. Monocrotaline can reduce blood pressure and inhibit cardiac contractility and heart rate and also shows mild inhibition of respiratory rate and depth.

• 臨床応用

  Monocrotaline injection shows well therapeutic effect for treating squamous cell carcinoma and basal cell carcinoma. In folk, the fresh pulp or dry powder of the herb has been also used for treating squamous cell carcinoma and basal cell carcinoma .

• 安全性プロファイル

  Suspected carcinogen with experimental carcinogenic data. Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

• 純化方法

  Crotaline forms prisms from absolute EtOH and recrystallises also from CHCl3. UV in 96% EtOH has max 217nm (log  3.32). [Adams et al. J Am Chem Soc 74 5612 1952, Culvenor & Smith Aust J Chem 10 474 1957.] The hydrochloride has m 212-214o (from MeOH/Et2O) and [] D28 -38.4o (c 5, H2O) [Adams & Gianturco J Am Chem Soc 78 1922 1956]. The picrate has m 230-231.5o(dec) [Adams et al. J Am Chem Soc 74 5614 1952]. [Beilstein 27 III/IV 6660.]

• 参考文献

  Adams, Rogers., J. Amer. Chern. Soc., 61,2815 (1939)

(13R,14R)-14,19-ジヒドロ-12,13-ジヒドロキシ-20-ノルクロタラナン-11,15-ジオン 上流と下流の製品情報

(13R,14R)-14,19-ジヒドロ-12,13-ジヒドロキシ-20-ノルクロタラナン-11,15-ジオン 生産企業

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(13R,14R)-14,19-ジヒドロ-12,13-ジヒドロキシ-20-ノルクロタラナン-11,15-ジオン スペクトルデータ(¹HNMR、IR1、MS、Raman)

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