Title: Helicin
CAS Registry Number: 618-65-5
CAS Name: 2-(b-D-Glucopyranosyloxy)benzaldehyde
Additional Names: salicylaldehyde b-D-glucoside
Molecular Formula: C13H16O7
Molecular Weight: 284.26
Percent Composition: C 54.93%, H 5.67%, O 39.40%
Literature References: Prepn by the oxidation of salicin with dil nitric acid: Schiff, Ann. 154, 19 (1870); from salicylaldehyde + O-tetraacetyl-a-glucosidyl bromide: Robertson, Waters, J. Chem. Soc. 1930, 2729. ORD and stereochemical studies: Tsuzuki et al., Bull. Chem. Soc. Jpn. 44, 526 (1971).
Properties: Needles with 0.75 mol H2O from H2O; mp 175-176° when dried at 100°. [a]D20 -60° (c = 1.4). One gram dissolves in 55 ml water; freely sol in hot water, alcohol. Forms compds with urea, thiourea, certain amino acids.
Melting point: mp 175-176° when dried at 100°
Optical Rotation: [a]D20 -60° (c = 1.4)
Derivative Type: Tetraacetate
Molecular Formula: C21H24O11
Molecular Weight: 452.41
Percent Composition: C 55.75%, H 5.35%, O 38.90%
Properties: Needles from alc, mp 142°. [a]D20 -37° (acetone).
Melting point: mp 142°
Optical Rotation: [a]D20 -37° (acetone)
NOTE: The same formula is ascribed to spirein, found in Spiraea camtschatica Pall. and in S. ulmaria L., Rosaceae. Emulsin hydrolyzes helicin and spirein, yielding D-glucose and salicylaldehyde. |