Zygadenine Property

Melting point:

214-216°

alpha 

D20 -48.4° (c = 1.26 in chloroform)

Hazard and Precautionary Statements (GHS)

Zygadenine Chemical Properties,Usage,Production

Description

A steroidal alkaloid isolated from the leaves of Zygadenus intermedius, this base forms clusters of colourless needles from C6H6 or Et20 or prisms of the diethanolate from EtOH. It is laevorotatory with [α]^{20/sup>_D - 48.2° (c 1.26, CHCl3). The salts and derivative crystallize well: hydrochloride, m.p. 23l-4°C; sulphate, m.p. 237-242°C; aurichloride monohydrate, decomposing at l40-l65°C; hexaacetate, m.p. 265-270°C and the vanilloyl derivative, m.p. 258-9°C; [α]23/sup>_D - 27.5° (CHCl3). The monoacetate is identical with Zygacine (q.v.) and the veratroyl derivative also occurs naturally in the rhizomes of Veratrum album. The structure of the alkaloid as 7-deoxygermine, has been established by chemical and spectroscopic investigation. The alkaloid is highly toxic and resembles cevadine in its action.}

Definition

ChEBI: Zygadenine is an alkaloid.

References

Heyl, Hepner, Loy.,!. Arner. Chern. Soc., 35,258 (1913) Heyl, Herr., ibid, 71, 1751 (1949) Stoll, Seebeck., Helv. Chirn. Acta, 36, 1570 (1953) Kupchan., J. Arner. Chern. Soc., 78,3546 (1956) Kupchan., ibid, 81, 1925 (1959) Gilbertson., Phytochern., 12,2079 (1973)