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| | SENKIRKIN Basic information |
| Product Name: | SENKIRKIN | | Synonyms: | RENARIDINE;SENKIKIN;SENKIRKIN;(4Z)-4-Ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione;11,16-trione,12-hydroxy-4-methyl-8-secosenecionan-8;2,12-Dihydroxy-4-methyl-11,16-dioxosenecionanium;4,8-Secosenecionan-8,11,16-trione, 12-hydroxy-4-methyl-;8,12-dihydroxy-4-methyl-11,16-dioxo-senecionaniu | | CAS: | 2318-18-5 | | MF: | C19H27NO6 | | MW: | 365.42 | | EINECS: | | | Product Categories: | Heterocycles;Mutagenesis Research Chemicals | | Mol File: | 2318-18-5.mol |  |
| | SENKIRKIN Chemical Properties |
| Melting point | 197°C | | Boiling point | 497.19°C (rough estimate) | | density | 1.2439 (rough estimate) | | refractive index | 1.5180 (estimate) | | storage temp. | -20°C | | form | Solid | | pka | 12.67±0.40(Predicted) | | color | White to off-white | | LogP | 0.690 (est) | | IARC | 3 (Vol. 31, Sup 7) 1987 |
| | SENKIRKIN Usage And Synthesis |
| Description | A further hepatotoxiC alkaloid present in Senecio kirkii Hook, S. renardi and Nardosrnia laevigata. The base has [α]25D - 16° (c 1.89, MeOH) or[α]15D - 6.2° (c 1.91, CHCI3). It forms colourless plates when crystallized from either Me2CO or AcOEt and yields a picrate, m.p. 225.5-226°C and a picrolonate, m.p. 109- 110°C. The ultraviolet spectrum shows a single absorption maximum at 219 mp.. Several crystalline salts and derivatives are known, e.g. the aurichloride, m.p. 182.5-183.5°C; platinichloride, m.p. 196-7°C (dec.); bitartrate, m.p. 201°C; reineckate, m.p. 169-171°C; picrate, m.p. 225- 225.5°C; picrolonate, m.p. 138°C and the methiodide, m.p. 194-6°C (dec.). The O-acetate occurs naturally (q.v.) in Senecio kirkii. | | Uses | Senkirkin, a pyrrolizidine alkaloid, occured in the aerial parts of the medicinal plant Tussilago farfara, could induce chromosome damage in human lymphocytes. Senkirkin can be metabolized by CYP3A4[1]. | | Definition | ChEBI: Senkirkine is a macrolide. | | Safety Profile | Poison by ingestion and
intraperitoneal routes. Questionable
carcinogen with experimental neoplastigenic
data. Mutation data reported. When heated
to decomposition it emits toxic fumes of
Nox | | References | Briggs, Mangan, Russell., J. Chern. Soc., 1891 (1948)
Massagetov, Kuzovkov.,J. Gen. Chern., USSR, 23, 158 (1953)
Danilova, Konovalova., ibid, 30, 1921 (1961)
Danilova, Koretskaya, Utkin., ibid, 31, 3815 (1961)
Wunderlich., Chern. Ind., 2089 (1962)
Briggs et al., J. Chern. Soc., 2492 (1965) |
| | SENKIRKIN Preparation Products And Raw materials |
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