| Identification | Back Directory | [Name]
SENKIRKIN | [CAS]
2318-18-5 | [Synonyms]
SENKIKIN
Kushenin
renardin
nsc-89945
SENKIRKIN
RENARIDINE
Senkarkane
senkirkine
renardine[neutral]
Renardine (neutral)
senkirkine(neutral)
senkirkine[neutral]
Senkirkine (neutral)
SENKIRKIN(RENARDINE)(SH)
2,12-Dihydroxy-4-methyl-11,16-dioxosenecionanium
8,12-dihydroxy-4-methyl-11,16-dioxo-senecionaniu
11,16-trione,12-hydroxy-4-methyl-8-secosenecionan-8
Senecionanium, 8,12-dihydroxy-4-methyl-11,16-dioxo-
12-Hydroxy-4-methyl-4,8-secosenecionan-8,11,16-trione
4,8-Secosenecionan-8,11,16-trione, 12-hydroxy-4-methyl-
trans-15-ethylidene-12-beta-hydroxy-4,12-alpha,13-beta-trimethyl8-oxo-4,8se
trans-15-Ethylidene-12-beta-hydroxy-4,12-alpha,13-beta-trimethyl 8-oxo-4,8 secosenec-1-enine
(4Z)-4-Ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione
2,9-Dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione, 4-ethylidene-7-hydroxy-6,7,14-trimethyl-, (1R,4Z,6R,7R)- | [Molecular Formula]
C19H27NO6 | [MDL Number]
MFCD01684247 | [MOL File]
2318-18-5.mol | [Molecular Weight]
365.42 |
| Chemical Properties | Back Directory | [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 ]
neat | [pka]
12.67±0.40(Predicted) | [LogP]
0.690 (est) | [IARC]
3 (Vol. 31, Sup 7) 1987 |
| Hazard Information | Back Directory | [Uses]
Senkirkine is a hepatotoxic pyrrolizidine alkaloid. Studies show that Senkirkine has carincogenic activity as it induced chromosomal aberrations in cultured mammalian cells as well as hepatic tumors in rats. | [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. | [Definition]
ChEBI: Senkirkine is a macrolide. | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
22 | [RIDADR ]
1544 | [WGK Germany ]
3 | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [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 | [Hazardous Substances Data]
2318-18-5(Hazardous Substances Data) |
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