3656. Ergosine

Nomenclature

CAS number: 561-94-4
12′-Hydroxy-2′-methyl-5′α-(2-methylpropyl)ergotaman-3′,6′,18-trione.
C30H37N5O5; mol wt 547.65.
C 65.79%, H 6.81%, N 12.79%, O 14.61%.

Description and 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).

Chemical structure

Properties

Prisms from ethyl acetate, dec 228°. [α]D20 -161° (chloroform). Sol in chloroform; fairly sol in methanol, acetone; sparingly sol in ethyl acetate, benzene.

Derivative

8α-Isomer.

Nomenclature

Ergosinine; ergoclavinine.
C30H37N5O5; mol wt 547.65.
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. [α]D20 +420° (chloroform); [α]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.

Note

Ergoclavine is an equimolar mixture of ergosine and ergosinine.