Title: Monotropein
CAS Registry Number: 5945-50-6
CAS Name: [1S-(1a,4aa,7b,7aa)]-1-(b-D-Glucopyranosyloxy)-1,4a,7,7a-tetrahydro-7-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-4-carboxylic acid
Molecular Formula: C16H22O11
Molecular Weight: 390.34
Percent Composition: C 49.23%, H 5.68%, O 45.09%
Literature 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 Type: Monohydrate
Properties: Needles from water, dec 170-173°. [a]D18 -127.7° (water). uv max: 235 nm (log e 3.98). Soluble in water, alcohol. Practically insol in ethyl acetate.
Optical Rotation: [a]D18 -127.7° (water)
Absorption maximum: uv max: 235 nm (log e 3.98)
Derivative Type: Pentaacetate
Molecular Formula: C26H32O16
Molecular Weight: 600.52
Percent Composition: C 52.00%, H 5.37%, O 42.63%
Properties: Crystals, mp 173-174.5°. [a]D18 -82.5° (ethanol).
Melting point: mp 173-174.5°
Optical Rotation: [a]D18 -82.5° (ethanol)
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