Wakeman—Pigments of Flowering Plants. 
839 
a study of chrysin. In a series of articles he described its 
principal properties and attacked the problem of its constitu¬ 
tion. This was determined later by Kostanecki 4 and his as¬ 
sociates. (1893-1904) The work of Kostanecki was confirmed 
by that of Darier 5 in 1895. 
Our present conception of the constitution of chrysin is based 
upon its decomposition by caustic alkalies into phloroglucin, 
acetic acid and benzoic acid, with small quantities of aceto¬ 
phenone. Also upon its synthesis from phloracetophenone 
trimethyl ether and ethyl benzoate. 
Chrysin occurs in the buds of many species of poplar, including 
Populus pyramidalis , 6 7 Populus nigra, 1 Populus monolifera 8 and 
Populus balsamifera. 9 
Chrysin forms clear yellow crystals. It melts at 275 and 
sublimes in fine needles at a temperature a little above the melt¬ 
ing point. It is insoluble in water but soluble in both hot and 
cold alcohol, in aniline and acetic acid. It is difficultly soluble 
in ether and almost insoluble in carbon disulphide. In alka¬ 
line solutions it dissolves with a yellow color. Chrysin is pre¬ 
cipitated from alcoholic solutions by lead acetate but dissolves 
in an excess of the reagent. 
Treated with chromic acid and acetic acid chrysin is oxidized 
to chrysone, 10 a red amorphous powder which crystallizes in deep 
red needles melting above 360. Chrysone is insoluble in the 
ordinary organic solvents. It dissolves in concentrated sulph¬ 
uric acid with a red color, in alkalies with a blue color. It 
forms a monoacetyl derivative which crystallizes in red needles. 
The acetyl derivative when reduced with zinc and acetic acid an¬ 
hydride forms a white acetylated hydroxychrysin which, when 
hydrolized, crystallizes in small crystals melting at 304-305. 
Tectochrysin , a methyl ether of chrysin. 
Tectochrysin 11 was first obtained by Piccard in the purifica¬ 
tion of chrysin. He called it tectochrysin from a Greek word 
4 Ber., 26, p. 2901; 32, p. 2260, 2449; 37, p. 3167. 
6 Ber., 27, p. 21. 
6 Ber., 6, p. 884. 
7 Ann., 101, p. 372. 
8 Ber., 6, 890; 7, p. 1485. 
9 Ber., 16, p. 176. 
10 Ber., 45, p. 499. 
11 Ber., 6, p. 888. 
