Germine
Title: Germine
CAS Registry Number: 508-65-6
CAS Name: (3b,4a,7a,15a,16b)-4,9-Epoxycevane-3,4,7,14,15,16,20-heptol
Molecular Formula: C27H43NO8
Molecular Weight: 509.63
Percent Composition: C 63.63%, H 8.50%, N 2.75%, O 25.12%
Literature References: Alkamine present in many polyester alkaloids which occur in Veratrum and Zygadenus species. Isoln: Poethke, Pharm. Monatsh. 18, 77 (1937); idem, Arch. Pharm. 275, 571 (1937); Seiferle et al., J. Econ. Entomol. 35, 35 (1942); Klohs et al., J. Am. Chem. Soc. 75, 4925 (1953); Kupchan, Deliwala, ibid. 76, 5545 (1954); Myers et al., ibid. 77, 3348 (1955); 78, 1621 (1956). Structure and configuration: Kupchan, Narayanan, ibid. 81, 1913 (1959). Comparative toxicity: O. Krayer et al., J. Pharmacol. Exp. Ther. 82, 167 (1944).
Properties: Crystals from methanol, mp 221.5-223°. [a]D25 +4.5° (95% ethanol); [a]D16 +23.1° (c = 1.13 in 10% acetic acid). Sol in chloroform, methanol, ethanol, acetone, water; slightly sol in ether. LD50 i.v. in mice: 139.0 mg/kg (Krayer).
Melting point: mp 221.5-223°
Optical Rotation: [a]D25 +4.5° (95% ethanol); [a]D16 +23.1° (c = 1.13 in 10% acetic acid)
Toxicity data: LD50 i.v. in mice: 139.0 mg/kg (Krayer)
 
Derivative Type: 3-Acetate
Molecular Formula: C29H45NO9
Molecular Weight: 551.67
Percent Composition: C 63.14%, H 8.22%, N 2.54%, O 26.10%
Properties: Needles from ether, mp 219-221°. [a]D23 +10° (c = 1.05 in pyridine).
Melting point: mp 219-221°
Optical Rotation: [a]D23 +10° (c = 1.05 in pyridine)
 
Derivative Type: 16-Acetate
Molecular Formula: C29H45NO9
Molecular Weight: 551.67
Percent Composition: C 63.14%, H 8.22%, N 2.54%, O 26.10%
Properties: Crystals from chloroform, mp 225-227°. [a]D23 -19° (c = 0.93 in pyridine).
Melting point: mp 225-227°
Optical Rotation: [a]D23 -19° (c = 0.93 in pyridine)
 
Derivative Type: 3,4,7,15,16-Pentaacetate
Molecular Formula: C37H53NO13
Molecular Weight: 719.82
Percent Composition: C 61.74%, H 7.42%, N 1.95%, O 28.90%
Properties: Prisms from acetone + petr ether, dec 285-287°. [a]D23 -65° (c = 0.65 in pyridine).
Optical Rotation: [a]D23 -65° (c = 0.65 in pyridine)

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