laurotetanine

laurotetanine Structure
CAS No.
128-76-7
Chemical Name:
laurotetanine
Synonyms
Litsoeine;NSC106610;NSC-106610;NSC 106610;Laurotetanin;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;4H-Dibenzo[de,g]quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-, (6aS)-
CBNumber:
CB01339347
Molecular Formula:
C19H21NO4
Molecular Weight:
327.37
MOL File:
128-76-7.mol
MSDS File:
SDS
Modify Date:
2026/4/24 14:59:02

laurotetanine 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)

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laurotetanine Chemical Properties,Uses,Production

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.

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)

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Raw materials

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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 4H-Dibenzo[de,g]quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-, (6aS)- 128-76-7