| Identification | Back Directory | [Name]
Zygadenine | [CAS]
545-45-9 | [Synonyms]
Zygadenine
4α,9-Epoxycevane-3β,4,14,15α,16β,20-hexol
Cevane-3,4,14,15,16,20-hexol, 4,9-epoxy-, (3β,4α,15α,16β)- | [Molecular Formula]
C27H43NO7 | [MDL Number]
MFCD22380979 | [MOL File]
545-45-9.mol | [Molecular Weight]
493.63 |
| Hazard Information | Back Directory | [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) |
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