4464. Glucovanillin

Nomenclature

CAS number: 494-08-6
4-(β-d-Glucopyranosyloxy)-3-methoxybenzaldehyde; vanillin-d-glucoside; avenein; vanilloside.
C14H18O8; mol wt 314.29.
C 53.50%, H 5.77%, O 40.73%.

Description and references

From green fruit of vanilla: Goris, Compt. Rend. 179, 70 (1924). From coniferin by oxidation with CrO3: Tremann, Ber. 18, 1595 (1885). Structure and synthesis: Fischer, Raske, Ber. 42, 1475 (1909); Thorpe, Williams, J. Chem. Soc. 1937, 494.

Chemical structure

Properties

Needles from methanol, mp 189-190°. Bitter taste. [α]D20 89.9° (water). Soluble in hot water, alcohol. Almost insol in ether.

Derivative

Tetraacetate.
C22H26O12; mol wt 482.43.
C 54.77%, H 5.43%, O 39.80%.

Properties

Crystals from dil alcohol, mp 142-143°. [α]D 48.3° (chloroform).

Use

Pharmaceutic aid (flavor).