| Identification | Back Directory | [Name]
QUININE | [CAS]
511-98-8 | [Synonyms]
Soladulcidine
Dihydrosolasodine
(22R,25R)-5α-Spirosolane-3β-ol
Spirosolan-3-ol, (3β,5α,22α,25R)-
(2aS,2'R,4S,5'R,6aS,6bS,8aS,8bR,9S,11aS,12aS,12bR)-5',6a,8a,9-tetramethyloctadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-piperidin]-4-ol | [Molecular Formula]
C27H45NO2 | [MDL Number]
MFCD00212688 | [MOL File]
511-98-8.mol | [Molecular Weight]
415.65 |
| Hazard Information | Back Directory | [Description]
This alkaloid from Solanum dulcamara forms colourless plates when crystallized from MeOH. It is laevorotatory with [α]D - 50° (c 0.4, CHCI3). The alkaloid forms the O,N-diformyl derivative which exists as two rotational isomers, the trans with m.p. 222-4°C; [α]20D - 21.2° (CHCI3) and the cis isomer with m.p. 202-4°C; [α]20D - 69.6° (CHCI3). | [Uses]
Soladulcidine is a steroidal glycoalkaloid extracted from tomato leaves and berries and can induce craniofacial malformations in hamsters. | [Definition]
ChEBI: Soladulcidine is an azaspiro compound, a steroid and an oxaspiro compound. | [References]
Schreiber., Planta Med., 6,93 (1958)
Alkemeyer, Sandor., Naturwiss., 46, 207 (1959)
Schreiber, Adam., Experientia, 17,13 (1961)
Schreiber, Adam., Annalen, 666, 155 (1963)
Synthesis:
Adam, Schreiber., Experientia, 21,471 (1965)
Adam, Schreiber., Tetrahedron, 22, 3591 (1966)
Absolute configuration:
Boll, von Philipsborn., Acta Chem. Scand., 19,1365 (1965) |
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