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Jacobine.

CAS No.
6870-67-3
Chemical Name:
Jacobine.
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)-
CBNumber:
CB71248363
Molecular Formula:
C18H25NO6
Molecular Weight:
351.39
MDL Number:
MFCD00870079
MOL File:
6870-67-3.mol
MSDS File:
SDS
Last updated:2023-05-04 17:34:41

Jacobine. Properties

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)
FDA UNII GM32U80H1R
IARC 3 (Vol. 10, Sup 7) 1987

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302
Precautionary statements  P264-P270-P301+P312-P330-P501
RIDADR  1544
HazardClass  6.1(b)
PackingGroup  III

Jacobine. price More Price(10)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
TRC J210395 Jacobine 6870-67-3 0.25mg $160 2021-12-16 Buy
TRC J210395 Jacobine 6870-67-3 0.5mg $305 2021-12-16 Buy
TRC J210395 Jacobine 6870-67-3 1mg $570 2021-12-16 Buy
Biosynth Carbosynth BJ161539 Jacobine 6870-67-3 10mg $900 2021-12-16 Buy
Biosynth Carbosynth BJ161539 Jacobine 6870-67-3 25mg $1875 2021-12-16 Buy
Product number Packaging Price Buy
J210395 0.25mg $160 Buy
J210395 0.5mg $305 Buy
J210395 1mg $570 Buy
BJ161539 10mg $900 Buy
BJ161539 25mg $1875 Buy

Jacobine. Chemical Properties,Uses,Production

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)

Jacobine. Preparation Products And Raw materials

Raw materials

Preparation Products

Jacobine. Suppliers

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Jacobine. (15R,20S)-15,20-Dihydro-15,20-epoxy-12-hydroxysenecionan-11,16-dione (20S)-15α,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione NSC-89936 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)- 6870-67-3 C8H25NO6