Swertiamarin

Title: Swertiamarin
CAS Registry Number: 17388-39-5
CAS Name: [4aR-(4aa,5b,6a)]-5-Ethenyl-6-(b-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-4a-hydroxy-1H,3H-pyrano[3,4-c]pyran-1-one
Additional Names: 4,4a,5,6-tetrahydro-4aa-hydroxy-1-oxo-5b-vinyl-1H,3H-pyrano[3,4-c]pyran-6-yl b-D-glucopyranoside
Molecular Formula: C16H22O10
Molecular Weight: 374.34
Percent Composition: C 51.34%, H 5.92%, O 42.74%
Literature References: Bitter principle of Swertia japonica (Maxim.) Makino, Gentianaceae. Yields erythrocentaurin on hydrolysis with emulsin. Isoln: Kubota, Tomita, Chem. Ind. (London) 1958, 229; Inouye et al., Chem. Pharm. Bull. 18, 1856 (1970). Occurrence in gentianaceous plants: Inouye, Nakamura, J. Pharm. Sci. Japan 91, 755 (1971), C.A. 75, 95431b (1971). Structure: Kubota, Tomita, Tetrahedron Lett. 1961, 176; Bull. Chem. Soc. Jpn. 34, 1345 (1961); Koch et al., Bull. Soc. Chim. Fr. 1964, 405. Stereochemistry: Inouye et al., Tetrahedron Lett. 1968, 4429. Biosynthesis studies: Inouye et al., Chem. Pharm. Bull. 18, 2043 (1970).
Properties: Plates from ethanol + chloroform + ether, mp 113-114°. [a]D20 -127° (c = 1 in 96% ethanol). uv max (methanol): 238 nm (log e 3.93).
Melting point: mp 113-114°
Optical Rotation: [a]D20 -127° (c = 1 in 96% ethanol)
Absorption maximum: uv max (methanol): 238 nm (log e 3.93)
Derivative Type: Tetraacetate
Molecular Formula: C24H30O14
Molecular Weight: 542.49
Percent Composition: C 53.14%, H 5.57%, O 41.29%
Properties: Prisms, mp 190-191°. [a]D -100.3° (CHCl3). uv max: 206, 234 nm (log e 3.20, 4.00).
Melting point: mp 190-191°
Optical Rotation: [a]D -100.3° (CHCl3)
Absorption maximum: uv max: 206, 234 nm (log e 3.20, 4.00)
Sydnones sym-Dichloroethyl Ether sym-Dichloromethyl Ether sym-Diphenylcarbazide sym-Diphenylpyrophosphorodiamidic Acid