Title: Verticine
CAS Registry Number: 23496-41-5
CAS Name: (3b,5a,6a)-Cevane-3,6,20-triol
Additional Names: peimine
Molecular Formula: C27H45NO3
Molecular Weight: 431.65
Percent Composition: C 75.13%, H 10.51%, N 3.24%, O 11.12%
Literature References: A member of the hexacyclic Ceveratrum group of alkaloids. Isoln from Fritillaria verticillata Willd. var. Thunbergii Baker, Liliaceae: Fukuda: Sci. Rep. Res. Inst. Tohoku Univ. Ser. A 18, 323 (1929); Morimoto, Kimata, Chem. Pharm. Bull. 8, 302 (1960). Also isolated from F. roylei Hook: Chou, Chen, Chin. J. Physiol. 6, 265 (1932), C.A. 26, 5703 (1932). Structure: Ito et al., ibid. 11, 1337 (1963). Abs config: S. Ito et al., Tetrahedron Lett. 1968, 5373. Total synthesis: J. P. Kutney et al., J. Am. Chem. Soc. 99, 964 (1977).
Properties: Needles from ethanol, mp 223-224°. [a]D16 -19.4° (ethanol); [a]D17 -20° (CHCl3). pK¢a 9.5. uv max (ethanol + HCl): 215 nm (e 10).
Melting point: mp 223-224°
pKa: pK¢a 9.5
Optical Rotation: [a]D16 -19.4° (ethanol); [a]D17 -20° (CHCl3)
Absorption maximum: uv max (ethanol + HCl): 215 nm (e 10)
Derivative Type: Hydrochloride
Molecular Formula: C27H45NO3.HCl
Molecular Weight: 468.11
Percent Composition: C 69.28%, H 9.90%, N 2.99%, O 10.25%, Cl 7.57%
Properties: Prisms from water, dec 291-294°. [a]D18 -18.5°.
Optical Rotation: [a]D18 -18.5°
Derivative Type: Perchlorate
Molecular Formula: C27H45NO3.HClO4
Molecular Weight: 532.11
Percent Composition: C 60.94%, H 8.71%, N 2.63%, O 21.05%, Cl 6.66%
Properties: Prisms from water, dec 273°. [a]D23 -15° (c = 0.05).
Optical Rotation: [a]D23 -15° (c = 0.05)
Derivative Type: Methiodide
Molecular Formula: C27H45NO3.CH3I
Molecular Weight: 573.59
Percent Composition: C 58.63%, H 8.43%, N 2.44%, O 8.37%, I 22.12%
Properties: Crystals from butanol + ether, dec 205-210°. [a]D18 -14.0° (water). Sol in water, methanol, ethanol; practically insol in chloroform, benzene, acetone.
Optical Rotation: [a]D18 -14.0° (water)
Derivative Type: 3-Glucoside
Additional Names: Peiminoside
Molecular Formula: C33H55NO8
Molecular Weight: 593.79
Percent Composition: C 66.75%, H 9.34%, N 2.36%, O 21.56%
Properties: Pale brown powder. Sol in water, methanol, alc; sparingly sol in benzene.
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