234 



AROMATIC ALDEHYDES AND KETONES [139-141 A. 



139. Tectoclirysiii ; 

 l-Hydroxy-3-Methoxyflavone. 



CH 



C.C 6 H 5 

 CH 



\/\co/ 



HO 



NATURAL SOURCE. 



In poplar buds with chrysin (Piccard, 

 Ber. 6, 890). 



SYNTHETICAL PROCESS. 



[A.] From elm/sin [138] by methyla- 

 tion with methyl iodide and potassium 

 hydroxide (Piccard, Ber. 10, 176; 

 Emilewicz and Kostanecki, Ber. 32, 

 2449). 



140. Apigenin; 

 1:3: 4 1 -Trihydroxyflavone. 



OH 



HO 



NATURAL SOURCE. 



Occurs as glucoside (apiin) in stem, 

 leaves, and seeds of parsley, Apium 

 petroselinum (Braconnot, Ann. 48, 349 ; 

 Planta and Wallace, Ann. 74, 262 ; 

 Lindenborn, Ber. 9, 1123; Vongerich- 

 ten, Ibid. 1 1 24 ; 33, 2334 ; 2904; Ann. 

 318, 121 : see also under phloroglucinol 

 [86]). 



A methyl ether of apigenin (acacetin) 

 is present in the leaves of Robinia pseud- 

 acacia (A. G. Perkin, Trans. Ch. Soc. 

 77, 43)- 



SYNTHETICAL PROCESSES. 



[A.] From anisic acid [Vol. II], 

 phloroglucinol [86], acetic acid [Vol. Ill, 

 and methyl and ethyl alcohols [13 ; 14] 

 as accessories. Anisic ethyl ester is 

 condensed with phloracetophenonetri- 

 methyl ether (see under chrysin [138; 



A]) by heating with sodium in xylene 

 solution. The product = 2 : 4 : 6 : 4 1 - 

 tetramethoxybenzoylacetophenone, on 

 heating with strong hydriodic acid, 

 gives apigenin (Czajkowski, Kostanecki, 

 and Tambor, Ber. 33, 1988). 



141. Luteolin; 

 1 : 3 ; 3 1 : 4 1 -Tetrahydroxyflavone. 



OH 



HO, 



OH 



HO 



NATURAL SOURCES. 



In weld from Reseda luteola (Chev- 

 reul, Journ. Chim. Med. 6, 157 ; Berz. 

 Jahresber. 11, 280; Moldenhauer, Ann. 

 100, 180; Schiitzenberger and Paraf, 

 Bull. Soc. [i] 1861, 18; Journ. pr. Ch. 

 [i] 83, 368 ; Ann. Suppl. 1, 256 ; 

 Jahresber. 1861, 707 ; Rochleder and 

 Breuer, Zeit. [2] 2, 602 ; Hlasiwetz 

 and Pfaundler, Journ. pr. Ch. [i] 94, 

 94 ; A. G. Perkin, Trans. Ch. Soc. 69, 

 206 ; 799 ; A. G. P. and Horsfall, 

 Hid. 77, 1314). 



Luteolin occurs in the colouring- 

 matter from the flowers of dyer's 

 broom, Genista tinctoria (A. G. P. and 

 Newbury, Proc. Ch. Soc. 15, 179). 



A glucoside contained in parsley with 

 apiin is a derivative of luteolin methyl 

 ether (Vongerichten, Ber. 33, 2334; 

 2904). 



Scoparin from broom, Spartium sco- 

 parium, may be a glucoside of methyl- 

 luteolin (A. G. Perkin, Proc. Ch. Soc. 

 16, 45 ; Trans. 77, 423)- . 



Digitoflavone from Digitalis leaves is 

 identical with luteolin (Kiliani and 

 Mayer, Ber. 34, 3577). 



SYNTHETICAL PROCESS. 



[A.] From phloroglncinol [86], acetic 

 and veratric acids [Vol. II], methyl and 

 ethyl alcohols [13; 14]. Phloraceto- 

 phenonetrimethyl ether (see under 

 chrysin [138 ; A]) and ethyl veratrate 



