6255. Monotropein
Nomenclature
CAS number: 5945-50-6
[1S-(1α,4aα,7β,7aα)]-1-(β-d-Glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid. C16H22O11; mol wt 390.34.
C 49.23%, H 5.68%, O 45.09%.
Description and references
From herb of Monotropa hypopitys L., Ericaceae: Bridel, Compt. Rend. 176, 1742 (1923); Bull. Soc. Chim. Biol. 5, 722 (1923). Structure: Inouye et al., Tetrahedron Lett. 1963, 1031; Bobbitt et al., Chem. Ind. (London) 1964, 931. Stereochemistry: Norio et al., Tetrahedron Lett. 1967, 2367. GC-mass spec studies: H. Inouye et al., J. Chromatogr. 118, 201 (1976). Purgative activity: eidem, Planta Med. 25, 285 (1976).
Derivative
Monohydrate.Properties
Needles from water, dec 170-173°. [α]D18 -127.7° (water). uv max: 235 nm (log ε 3.98). Soluble in water, alcohol. Practically insol in ethyl acetate.Derivative
Pentaacetate.C26H32O16; mol wt 600.52.
C 52.00%, H 5.37%, O 42.63%.