160 



AROMATIC ALCOHOLS AND PHENOLS 



[85-86. 



85. Hydroxyqiiiiiol ; 



Hydroxyliydroqtiiiioue ; 



1:2: 4-Phenetriol. 



HO 



H 



V 



NATURAL SOURCE. 



The complex is probably contained in 

 the colouring-matter of red grapes 

 (Sostegni, Gazz. 32, 17). 



SYNTHETICAL PROCESSES. 



[A.] From quinol [7l] by fusion with 

 caustic soda (Barth and Schreder, 

 Monats. 4, 176; 5, 590). 



[B.] Qvinone [142] on treatment with 

 acetic anhydride and strong sulphuric 

 or phosphoric acid gives hydroxyquinol- 

 triacetate, from which the phenol is 

 liberated by acid hydrolysis (Thiele, 

 Ber. 81, 1247; Bayer & Co., Germ. 

 Pat. 101607 of 1897 ; Ch. Centr. 1899, 

 1, 1094 ; and Suppl. Pat. 107508 of 

 1898; Ch. Centr. 1900, 1, 1087). 



86. Phloroglncinol ; 

 1:3: 5-Plienetriol. 



HO 



H 



HOv ;OH 



H 

 0:' 



V 



NATURAL SOURCES. 



Phloroglucinol has been said to occur 

 in the free state in many plants (Wein- 

 zierl, Lindt, and Waage, Ber. deutsch. 

 bot. Gesell. 8, 250), but according to 

 Moller (Ch. Centr. 1897, 2, 1151) this 

 observation is erroneous. Occurs in 

 the colouring-matter of red grapes 

 (Sostegni, Journ. Ch. Soc. 70, II, 122). 

 Said to have been found in the bark 

 of Styrax benzoin and (as dibutyrate) in 

 the root of Aspidiumfilix mas. 



The phloroglucinol complex is con- 

 tained in the glucosides : 



Hesperidin; widely distributed in 

 fruit of the genus Citrus, such as C. 

 aurantium, C. limonum, O. limetta, C. 

 medico, , &c. In fruit of Diosma alia 

 and other species. Hesperidin is de- 

 composed by certain moulds, such as 

 Aspergittus niger, &c. (Puriewitsch, Ber. 

 deutsch. bot. Gesell. 16, 368). 



Glycyphyllin (through phloretin) ; 

 from leaves of Smilax glycyphylla from 

 Australia. 



Phloridzin (through phloretin) ; from 

 root-bark of apple, cherry, plum, pear, 

 &c. 



Naringin or aurantiin ; from all parts, 

 and especially from the full-blown 

 flowers, of Citrus decumana from Java. 



Loka'in; the colouring-matter of 

 Chinese green from the berries of the 

 buckthorns Rhamnus utilis and R. chloro- 

 phorus. 



The phloroglucinol complex exists 

 in quercetin, rhamnetin, isorhamnetin, 

 rhamnazin, Inteolin [l4l], and con- 

 sequently in glucosides such as xantho- 

 rhamnin, quercitrin, rutin, osyritrin, 

 violaquercitrin, and robinin. (For 

 occurrence see under catechol [69].) 



Also in maclurin [69], morin (see 

 under resorcinol [70]), and myricetin 

 (see under pyrogallol [84]) ; in chrysin 

 [138], the yellow colouring-matter of 

 poplar buds from Populus nigra, P. bal- 

 samifera, and P. pyramidalis (Kosta- 

 necki, Ber. 26, 2901) ; in apiin (through 

 apigettin [140]), a glucoside found in the 

 stem, seeds, and leaves of parsley, Apium 

 petroselium (A. G. Perkin, Trans. Ch. 

 Soc. 71, 817). Apigenin has been 

 found also (with luteolin) in weld 

 (A. G. Perkin and Horsfall, Proc. Ch. 

 Soc. 16, 182). 



Cyanomaclurin, obtained from Arto- 

 carpus integrifolia (A. G. P. and Cope, 

 Trans. Ch. Soc. 67, 939), contains the 

 phloroglucinol group, and is related to 

 the catechins of Gambir and Acacia 

 catechu, which also contain this com- 

 plex (A. G. P. and Yoshitake, Proc. Ch. 

 Soc. 18, 139; Trans. 81, 1172). 



Lotusin, a glucoside contained in 

 Lotus arabicus from Egypt and N. 

 Africa, gives on hydrolysis lotoflavin, 



