laurotetanine
laurotetanine Basic information
- Product Name:
- laurotetanine
- Synonyms:
-
- laurotetanine
- (6aS)-5,6,6a,7-Tetrahydro-1,2,10-trimethoxy-4H-dibenzo[de,g]quinolin-9-ol
- [S,(+)]-5,6,6a,7-Tetrahydro-1,2,10-trimethoxy-4H-dibenzo[de,g]quinolin-9-ol
- Litsoeine
- Laurotetanin
- NSC 106610
- NSC106610
- NSC-106610
- CAS:
- 128-76-7
- MF:
- C19H21NO4
- MW:
- 327.37
- Mol File:
- 128-76-7.mol
laurotetanine Chemical Properties
- Melting point:
- 125°C
- Boiling point:
- 465.27°C (rough estimate)
- Density
- 1.2223 (rough estimate)
- refractive index
- 1.5000 (estimate)
- pka
- 9.76±0.20(Predicted)
laurotetanine Usage And Synthesis
Description
The noraporphine alkaloid was first isolated by Greshoff from Litsea chrysocorna and subsequently from other species of Lauraceae including L. citrata and L. cubeba. When freshly crystallized from Me2 CO it yields colourless crystals but these become yellow in air. The alkaloid behaves as a phenolic base giving salts with mineral acids which all contain H20 of crystallization. The picrate monohydrate has m.p. 1480 C, the dibenzoyl derivative, m.p. 169-1700 C and the phenylthiocarbamide, m.p. 211-2°C. Three methoxyl groups, an imino group and a phenolic hydroxyl group are present, the latter giving the O-methyl ether which is an amorphous powder but yields a crystalline hydrochloride, m.p. 245°C; an oxalate, m.p. 233°C and the thiocarbamide, m.p. 154-5°C. The Nmethyl derivative (q.v.) is found naturally in Peurnus boldus and the O,Ndimethyl derivative is glaucine. The structure has been determined from chemical degradation and synthesis.
Definition
ChEBI: Litsoeine is an isoquinoline alkaloid.
References
Greshoff., Ber., 23,3537 (1890)
Filippo., Arch. Pharm., 236, 601 (1898)
Gorter., Bull. Jard. bot. Buitenzorg., 3, 180 (1921)
Barger, Silberschmidt.,J. Chem. Soc., 2919 (1928)
Barger et al., Ber., 66, 450 (1933)
Ruegger., Helv. Chim. Acta, 42,754 (1959)
Kikkawa.,J. Pharm. Soc., Japan, 79,83,425 (1959)