4628. Helicin

Nomenclature

CAS number: 618-65-5
2-(β-d-Glucopyranosyloxy)benzaldehyde; salicylaldehyde β-d-glucoside.
C13H16O7; mol wt 284.26.
C 54.93%, H 5.67%, O 39.40%.

Description and references

Prepn by the oxidation of salicin with dil nitric acid: Schiff, Ann. 154, 19 (1870); from salicylaldehyde + O-tetraacetyl-α-glucosidyl bromide: Robertson, Waters, J. Chem. Soc. 1930, 2729. ORD and stereochemical studies: Tsuzuki et al., Bull. Chem. Soc. Jpn. 44, 526 (1971).

Chemical structure

Properties

Needles with 0.75 mol H2O from H2O; mp 175-176° when dried at 100°. [α]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.

Derivative

Tetraacetate.
C21H24O11; mol wt 452.41.
C 55.75%, H 5.35%, O 38.90%.

Properties

Needles from alc, mp 142°. [α]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.