Title: Picein
CAS Registry Number: 530-14-3
CAS Name: 1-[4-(b-D-Glucopyranosyloxy)phenyl]ethanone
Synonyms: p-(acetylphenyl)-b-D-glucopyranoside; 4￠-(b-D-glucopyranosyloxy)acetophenone;
p-hydroxyacetophenone-D-glucoside; piceoside; salinigrin; salicinerein; ameliaroside
Molecular Formula: C14H18O7
Molecular Weight: 298.29
Percent Composition: C 56.37%, H 6.08%, O 37.55%
Literature 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).
Properties: Needles or prisms from methanol; mp 195-196°. [a]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).
Melting point: mp 195-196°
Optical Rotation: [a]D23 -88° (c = 1)
![CAS No:530-14-3 Ethanone, 1-[4-(b-D-glucopyranosyloxy)phenyl]-](/structure/cas-530/530-14-3.png)
