Calycanthine

Title: Calycanthine
CAS Registry Number: 595-05-1
Molecular Formula: C22H26N4
Molecular Weight: 346.47
Percent Composition: C 76.27%, H 7.56%, N 16.17%
Literature References: In Calycanthus floridus L., C. glaucus Willd.; Chimonanthus praecox (L.) Link, Calycanthaceae. First isoln: Eccles, Proc. Am. Pharm. Assoc. 84, 382 (1888). Extraction procedure: Manske-Marion, Can. J. Res. 17B, 293 (1939). Structure: Woodward et al., Proc. Chem. Soc. London 1960, 76; Hamor et al., ibid. 78; Hamor, Robertson, J. Chem. Soc. 1962, 194. Configuration: Clayton et al., Tetrahedron 18, 1495 (1962). Synthesis of DL-form: Hendrickson et al., ibid. 20, 565 (1964); Hall et al., ibid. 23, 4131 (1967).
Properties: Crystals, mp 245° (evac tube). [a]D18 +684° (c = 1.2 in abs alc). uv max (95% ethanol): 250, 309 nm (log e 4.28, 3.80). Alkaline reaction to litmus. Freely sol in alc, chloroform; sol in ether, acetone, pyridine; slightly sol in water.
Melting point: mp 245° (evac tube)
Optical Rotation: [a]D18 +684° (c = 1.2 in abs alc)
Absorption maximum: uv max (95% ethanol): 250, 309 nm (log e 4.28, 3.80)
Derivative Type: Monohydrate
Properties: Orthorhombic bipyramidal crystals from water, mp 220°.
Melting point: mp 220°
CAUTION: Highly toxic. Can cause violent convulsions, paralysis, cardiac depression.
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