7395. Picein

Nomenclature

CAS number: 530-14-3
1-[4-(β-d-Glucopyranosyloxy)phenyl]ethanone; p-(acetylphenyl)-β-d-glucopyranoside; 4′-(β-d-glucopyranosyloxy)acetophenone; p-hydroxyacetophenone-d-glucoside; piceoside; salinigrin; salicinerein; ameliaroside.
C14H18O7; mol wt 298.29.
C 56.37%, H 6.08%, O 37.55%.

Description and references

In needles and sprouts of Pinus picea L., Picea excelsa Link., Picea glehnii Mast., Coniferae: Tanret, Bull. Soc. Chim. [3] 11, 944 (1894); Kariyone et al., Yakugaku Zasshi 79, 394 (1959), C.A. 53, 14096i (1953). In various willow barks, especially in bark of Salix discolor Muhl., S. nigra Marsh., Salicaceae: Jowett, J. Chem. Soc. 77, 707 (1900); Nonomura, J. Pharm. Soc. Jpn. 75, 80 (1955). In English mistletoe, Amelanchier vulgaris Moench., Rosaceae: Bridel et al., Compt. Rend. 187, 56 (1928). Synthesis: Mauthner, J. Prakt. Chem. [2] 85, 564 (1912).

Chemical structure

Properties

Needles or prisms from methanol; mp 195-196°. [α]D23 -88° (c = 1). One gram dissolves in 50 ml water at 15°, in 1 ml boiling water, in ≈650 ml abs alc at 15°, in ≈40 ml boiling abs alc, in 140 ml ethyl acetate at 15°. Sol in hot glacial acetic acid. Practically insol in ether, chloroform. Hydrolysis with dil mineral acids or with emulsin yields d-glucose and p-hydroxyacetophenone (Piceol). Alkaline hydrolysis yields levoglucosan and p-hydroxyacetophenone: Montgomery et al., J. Org. Chem. 10, 194 (1945).