(-)-Pancracine
- CAS No.
- 21416-14-8
- Chemical Name:
- (-)-Pancracine
- Synonyms
- Pancracine;(-)-Pancracine;(6aS)-5,6a,7,8,9,11-Hexahydro-6β,11β-methano-6H-1,3-benzodioxolo[5,6-c][1]benzazepine-8α,9β-diol;6,11-Methano-6H-1,3-benzodioxolo[5,6-c][1]benzazepine-8,9-diol, 5,6a,7,8,9,11-hexahydro-, (6R,6aS,8S,9S,11S)-
- CBNumber:
- CB32414301
- Molecular Formula:
- C16H17NO4
- Molecular Weight:
- 287.31
- MDL Number:
- MOL File:
- 21416-14-8.mol
(-)-Pancracine Chemical Properties,Uses,Production
Description
This alkaloid occurs in Narcissus poeticus, Pancratium maritium and Rhodo_x0002_phiala bifida. It yields long, colourless prisms when recrystallized from MeOH and is laevorotatory with [α]25D - 74° (c 0.02, MeOH). The ultraviolet spectrum has two absorption maxima at 241 and 292 mil. It yields a crystalline perchlorate, m.p. 163-6°C and a picrate, m.p. 249-2S2°C. Two non-phenolic hydroxyl groups and one methylenedioxy group are present in the molecule. The 2-a-O-acetate is an amorphous solid which cannot be obtained crystalline but the 3-{3-0-acetate forms colourless crystals from MeOH, m.p. 213-6°C. The O,O-diacetate, also crystalline, has m.p. 163-S°C. The O-methyl derivatives occur naturally, the 2-methyl compound is Montanine (q.v.) and the 2:3-dimethyl ether is Manthine (q.v.). The structure is based primarily upon the mass spectrum fragmentation pattern.
Definition
ChEBI: Hippagine is a benzazepine.
References
Sandberg, Michel., Lloydia, 26, 78 (1963)
Structure:
Wildman, Brown.,J. Amer. Chem. Soc., 90,6439 (1968)