|
|
| | METELOIDINE Basic information |
| Product Name: | METELOIDINE | | Synonyms: | METELOIDINE;6,7-Dihydroxy-3-tiglyloxytropane;(E)-2-Methyl-2-butenoic acid (1S,5R)-6β,7β-dihydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3α-yl ester;Meteloidin;Meteloidin-14C;3-tigloyloxy-6,7-dihydroxytropane;3endo-tigloyloxy-tropane-6exo,7exo-diol;2-Butenoic acid, 2-methyl-, (1R,3-endo,5S,6S,7R)-6,7-dihydroxy-8-methyl-8-azabicyclo[3.2.1]oct-3-yl ester, (2E)-rel- | | CAS: | 526-13-6 | | MF: | C13H21NO4 | | MW: | 255.31 | | EINECS: | | | Product Categories: | | | Mol File: | 526-13-6.mol |  |
| | METELOIDINE Chemical Properties |
| Melting point | 141-142° | | Boiling point | 383.9±41.0 °C(Predicted) | | density | 1.23±0.1 g/cm3(Predicted) | | pka | 13.48±0.60(Predicted) |
| | METELOIDINE Usage And Synthesis |
| Description | A tropane alkaloid first found by Pyman and Reynolds in Datura rneteloides, the
base also occurs in D. ferox and the leaves of Erythroxylurn australe. It crystallizes
from C6H6 in tabular needles and is readily soluble in CHC13 or EtOH but
only slightly so in Et20, C6H6 or H20. The hydrochloride is obtained as chiselshaped
needles of the diliydrate, m.p. 250°C (dry); the aurich10ride hemihydrate
also forms needles, m.p. 149-1500 C, the picrate, m.p. 177-1800 C and the
reineckate, m.p. 140°C (dec.). Hydrolysis with Ba(OHh furnishes tiglic acid and
teloidine, CSH1S0 3N, m.p. 168-9°C. The latter may be characterized as the
crystalline hydrochloride, m.p. > 300°C; hydrobromide, m.p. 295°C and the
aurichloride, m.p. 225°C. The alkaloid is physiologically inactive. | | References | Pyman, Reynolds.,]. prakt. Chern., 64,274 (1901)
Evans, Partridge., Chern. Abstr., 42,7486 (1948)
Sheehan, Bissell.,]. Org. Chern., 19,270 (1954)
Heusner., Z. Naturforsch., 96,683 (1954)
Heusner., Ber., 87, 1032 (1954)
Johns, Lamberton., Austral. J. Chern., 20,1301 (1967) |
| | METELOIDINE Preparation Products And Raw materials |
|