Title: Verbenalin
CAS Registry Number: 548-37-8
CAS Name: [1S-(1a,4aa,7a,7aa)]-1-(b-D-Glucopyranosyloxy)-1,4a,5,6,7,7a-hexahydro-7-methyl-5-oxocyclopenta[c]pyran-4-carboxylic acid methyl ester
Additional Names: cornin
Molecular Formula: C17H24O10
Molecular Weight: 388.37
Percent Composition: C 52.57%, H 6.23%, O 41.20%
Literature References: A glycoside isolated from Verbena officinalis L., Verbenaceae, Cornus florida L., Cornaceae. Refs: Bourdier, J. Pharm. Chim. 27(6), 49, 101 (1908); Holste, Arch. Exp. Pathol. Pharmakol. 101, 46 (1924); Miller, J. Am. Pharm. Assoc. 17, 744 (1928). Identity with cornin: Reichert, Arch. Pharm. 273, 357 (1935). Structure: Büchi, Manning, Tetrahedron Lett. 1960, 5 (1960); eidem, Tetrahedron 18, 1049 (1962). Synthesis of verbenalol, the aglycone: P. Callant et al., ibid. 37, 2085 (1981).
Properties: Bitter needles, mp 182-183°. [a]D25 -173° (water). uv max: 238, 290 nm (e 9600, 105) in ethanol. Freely sol in water, slightly in alcohol, ethyl acetate, acetone. Practically insol in chloroform, ether.
Melting point: mp 182-183°
Optical Rotation: [a]D25 -173° (water)
Absorption maximum: uv max: 238, 290 nm (e 9600, 105) in ethanol |