References of 1H,3H-Pyrano[3,4-c]pyran-1-one,5-ethenyl-4,4a,5,6-tetrahydro-6-[[2-O-[(3,3',5-trihydroxy[1,1'-biphenyl]-2-yl)carbonyl]-b-D-glucopyranosyl]oxy]-,(4aS,5R,6S)-
Title: Amarogentin
CAS Registry Number: 21018-84-8
CAS Name: [4a
S-(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-1
H,3
H-pyrano[3,4-
c]pyran-1-one
Synonyms: 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)