9015. Syringaldehyde

Nomenclature

CAS number: 134-96-3
4-Hydroxy-3,5-dimethoxybenzaldehyde; syringic aldehyde; 3,5-dimethoxy-4-hydroxybenzene carbonal; gallaldehyde 3,5-dimethyl ether.
C9H10O4; mol wt 182.17.
C 59.34%, H 5.53%, O 35.13%.

Description and references

Widely distributed in plants. Hydrolysis product of the naturally occurring glycosyringic aldehyde: Krner, Gazz. Chim. Ital. 18, 215 (1888). Prepn from heat-treated beechwood and lignin: Kratzl, Silbernagel, C.A. 50, 6040 (1956). Synthesis from pyrogallol 1,3-dimethyl ether: Pearl, J. Am. Chem. Soc. 70, 1746 (1948), cf. Graebe, Martz, Ber. 36, 1032 (1903); Allen, Leubner, Org. Synth. 31, 92 (1951); coll. vol. IV, 866 (1963).

Chemical structure

Properties

Very pale yellow needles from petr ether, mp 113°. bp14 192-193°. uv max (dioxane): 305 nm. Very sparingly sol in water, petr ether. Sol in alcohol, ether, chloroform, hot benzene, glacial acetic acid. Forms yellow sodium and potassium salts.