Title: Amarogentin
CAS Registry Number: 21018-84-8
CAS Name: [4aS-(4aa,5b,6a)]-3,3¢,5-Trihydroxy[1,1¢-biphenyl]-2-carboxylic acid 2-ester with 5-ethenyl-6-(b-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one
Additional Names: sweroside-2¢-(3¢¢,5¢¢,3¢¢¢-trihydroxydiphenyl)-2¢¢-carboxylic acid ester
Molecular Formula: C29H30O13
Molecular Weight: 586.54
Percent Composition: C 59.38%, H 5.16%, O 35.46%
Literature References: Strongly bitter glucoside. Isoln from Swertia chirata Buch-Ham., Gentianaceae: Korte, Ber. 88, 704 (1955); 89, 2404 (1956); from Swertia japonica Makino: Inouye et al., Chem. Pharm. Bull. 18, 1856 (1970). Occurrence in gentianaceous plants: Inouye, Nakamura, J. Pharm. Soc. Jpn. 91, 755 (1971), C.A. 75, 95431b (1971). Structure: eidem, Tetrahedron Lett. 1968, 4919; eidem, Tetrahedron 27, 1951 (1971).
Properties: Colorless needles, mp 229-230° (monohydrate). [a]D20 -116.6° (methanol). uv max: 230, 266, 306 nm (log e 4.46, 4.07, 3.68). Slightly sol in benzene, water; freely sol in acetone, anhydr dioxane, tetrahydrofuran, methanol, ethanol. Practically insol in petr ether, ether, cyclohexane, CHCl3.
Melting point: mp 229-230° (monohydrate)
Optical Rotation: [a]D20 -116.6° (methanol)
Absorption maximum: uv max: 230, 266, 306 nm (log e 4.46, 4.07, 3.68) |