| Identification | Back Directory | [Name]
SENECIONINE | [CAS]
130-01-8 | [Synonyms]
qlgn
Aureine
Sencionine
SENECIONIN
SENECIONINE
Senecionine/Aureine
12-Hydroxysenecionan-11,16-dione
16-dione,12-hydroxy-senecionan-1
Senecionan-11,16-dione, 12-hydroxy-
(15cis)-12-Hydroxysenecionan-11,16-dione
[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)- | [Molecular Formula]
C18H25NO5 | [MDL Number]
MFCD00221720 | [MOL File]
130-01-8.mol | [Molecular Weight]
335.39 |
| Chemical Properties | Back Directory | [Melting point ]
236 °C(lit.)
| [alpha ]
D25 -55.1° (c = 0.034 in chloroform) | [Boiling point ]
472.03°C (rough estimate) | [density ]
1.266 g/cm3 | [refractive index ]
1.5100 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMF: 5 mg/ml; DMSO: 2 mg/ml; Ethanol: 1 mg/ml; PBS (pH 7.2): 0.1 mg/ml | [form ]
neat | [pka]
12.81±0.40(Predicted) | [optical activity]
[α]25/D 55.1°, c = 0.034% in chloroform | [BRN ]
8162955 | [InChIKey]
HKODIGSRFALUTA-JTLQZVBZSA-N | [LogP]
0.880 (est) | [EPA Substance Registry System]
Senecionine (130-01-8) |
| Hazard Information | Back Directory | [Description]
This hepatotoxic alkaloid is widely distributed among the Senecio species, being found in S. aureus, S. ilicifolius Thunb., S. integerrirnus, S. pseudaarnica, S. squaUdus, S. viscosus and S. vulgaris. The base is laevorotatory with [α]D - 54.6° (CHCI3 ) and the crystals sublime at 130-140°CfO.2 mm. The nitrate has m.p. 214°C;[α]D - 34.2° (H2 0); the aurichloride, m.p. 186°C; the picrate, m.p. 191°C and the methiodide, m.p. 249°C. Alkaline hydrolysis furnishes retronecine and senecic acid (6-hydroxy-5-methyl-2-heptene-3 :6-dicarboxylic acid). | [Uses]
Senecionine is a pyrrolizidine alkaloid with the potential to affect hepatic drug metabolizing enzymes in rat cells. | [Definition]
ChEBI: A pyrrolizidine alkaloid isolated from the plant species of the genus Senecio. | [Safety Profile]
Poison by intravenous,intraperitoneal, and possibly other routes. Anexperimental teratogen. Other experimental reproductiveeffects. Mutation data reported. When heated todecomposition it emits toxic fumes of NOx. | [References]
Grandval, Lajoux., Cornpt. rend., 120,1120 (1895)
Grandval, Lajoux., Bull. Soc. Chirn. Fr., 13,942 (1895)
Manske., Can. J. Res., S, 651 (1931)
Manske., ibid, 14B, 6 (1936)
Barger, Blackie., J. Chern. Soc., 584 (1937)
Blackie., Pharrn. J., 138,102 (1937)
Manske., Can. J. Res., 17B, I (1939) |
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