Title: Ergosine
CAS Registry Number: 561-94-4
CAS Name: 12¢-Hydroxy-2¢-methyl-5¢a-(2-methylpropyl)ergotaman-3¢,6¢,18-trione
Molecular Formula: C30H37N5O5
Molecular Weight: 547.65
Percent Composition: C 65.79%, H 6.81%, N 12.79%, O 14.61%
Literature References: Isoln of ergosine and ergosinine from ergot: Smith, Timmis, J. Chem. Soc. 1937, 396. Structure: Stoll et al., Helv. Chim. Acta 34, 1544 (1951). Stereochemistry: Stoll et al., ibid. 37, 2039 (1954). Total synthesis of ergosine and ergosinine: Stadler et al., ibid. 47, 1911 (1964).
Properties: Prisms from ethyl acetate, dec 228°. [a]D20 -161° (chloroform). Sol in chloroform; fairly sol in methanol, acetone; sparingly sol in ethyl acetate, benzene.
Optical Rotation: [a]D20 -161° (chloroform)
Derivative Type: 8a-Isomer
Additional Names: Ergosinine; ergoclavinine
Molecular Formula: C30H37N5O5
Molecular Weight: 547.65
Percent Composition: C 65.79%, H 6.81%, N 12.79%, O 14.61%
Properties: Prisms from 90% alcohol, aq acetone, benzene or ethyl acetate, dec 228°. Also reported as colorless needles, mp 190-191° (dec), Stadler et al., loc. cit. [a]D20 +420° (chloroform); [a]D20 +380° (acetone). Very readily sol in chloroform; readily sol in acetone; less sol in ethyl acetate; sparingly sol in benzene; very sparingly sol in methyl alcohol; almost insol in water.
Melting point: mp 190-191° (dec), Stadler et al., loc. cit
Optical Rotation: [a]D20 +420° (chloroform); [a]D20 +380° (acetone)
NOTE: Ergoclavine is an equimolar mixture of ergosine and ergosinine. |