| Identification | Back Directory | [Name]
Jacobine. | [CAS]
6870-67-3 | [Synonyms]
Jacobine.
NSC-89936
(20S)-15α,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione
(15R,20S)-15,20-Dihydro-15,20-epoxy-12-hydroxysenecionan-11,16-dione
Spiro[[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-3(2H),2'-oxirane]-2,7(4H)-dione, 5,6,9,11,13,14,14a,14b-octahydro-6-hydroxy-3',5,6-trimethyl-, (2'S,3'S,5R,6R,14aR,14bR)- | [Molecular Formula]
C18H25NO6 | [MDL Number]
MFCD00870079 | [MOL File]
6870-67-3.mol | [Molecular Weight]
351.397 |
| Chemical Properties | Back Directory | [Melting point ]
228°C | [Boiling point ]
485.2°C (rough estimate) | [density ]
1.2737 (rough estimate) | [refractive index ]
1.5100 (estimate) | [pka]
12.89±0.60(Predicted) | [IARC]
3 (Vol. 10, Sup 7) 1987 |
| Hazard Information | Back Directory | [Description]
This alkaloid of the pyrrolizidine group of bases occurs in Senecio cineraria D.C.,
S. crucifolia and S. Jacobea. It is a laevorotatory base with [α]17D - 46.3°
(CHCl 3 ). The alkaloid forms crystalline salts and derivatives, e.g. the hydrochloride, m.p. 220°C; [α]19D - 14.3° (H20); nitrate, m.p. 234°C; methiodide,
m.p. 255°C and the picrate, m.p. 180°C which is soluble in H20. The alkaloid
contains two active hydrogens and on alkaline hydrolysis yields retronecine and
jaconecic acid, ClOH16 0 6, m.p. 182°C; [α]25D + 31.7° containing three O-methyl
groups | [Uses]
Jacobine is a pyrrolizidine alkaloid which has been shown to be an herbivore insect deterrent and may be used in the protection of vegetation. Extracted from Crassocephalum plant of West Africa. | [Definition]
ChEBI: Jacobine is a pyrrolizine alkaloid. | [References]
Manske., Can. J. Res., 5,651 (1931)
Hosking, Brandt., New Zealand J. Sci. Tech., 14,638 (1936)
Blackie.,Pharrn. J., 138,102 (1937)
Barger, Blackie., J. Chern. Soc., 584 (1937)
Bradbury, Willis., Austral. J. Chern., 9,258 (1956)
Geissman., ibid, 12,247 (1959)
Bradbury, Masamune., J. Arner. Chern. Soc., 81,5201 (1959)
Masamune., ibid, 82, 5253 (1960)
Freidrichsons, Mathieson, Sutor., Tetrahedron Lett., 35 (1960) |
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