138 



AROMATIC ALCOHOLS AND PHENOLS 



[69. 



foliage (Kraus, N. Rep. Pharm. 22, 

 273; Journ. Ch. Soc. 26, 1049 : Preusse, 

 Bied. Centr. 1879, 874, denies the 

 existence of free catechol in plants). 



Occurs in leaves of the Virginian 

 creeper, Ampelopsis hederacea (Gorup- 

 Besanez, Ber. 4, 905), in sap of the 

 kino plants, Butea frondosa, Eucalyptus 

 resimfera, Pterocarpus marsupium, P. 

 erinaceus, &c. (Eisfeldt, Ber. 4, 906 ; 

 Fliickiger, Ber. 5, i ; Gorup-Besanez, 

 Ibid. 47), in raw beet-sugar (v. Lipp- 

 mann, Ber. 20, 3298 : see also Ber. 26, 

 3061), and in the dry external scales of 

 the onion. 



Catechol has been found in Puglia 

 olive oil (Canzoneri, Gazz. 27, 3), in the 

 colouring-matter of red grapes (Sostegni, 

 Journ. Ch. Soc. 7O, II, 122), in the 

 aqueous distillate (tar water) from bitu- 

 minous shale (Germ. Pat. 58944 of 

 1892; Ber. 35, 4325 note) and from 

 coal (Bornstein, Ber. 35, 4324). In 

 these last cases the catechol may be 

 a product of destructive distillation. 



A glucoside contained in the tansy, 

 Tanacetum vulgare, is a compound of 

 catechol with dextrose and Isevulose 

 (Nedra, Journ. Soc. Ch. Ind. 19, 686). 



The catechol complex exists in many 

 products of vegetable origin : 



Quercetin and isomerides from Persian 

 berries (fruit of various species of Rkam- 

 nus) ; from the bark of Quercus tinctoria; 

 from the fruit, flowers, and leaves of the 

 horse-chestnut ; from the berries of the 

 sea-buckthorn (Hippophae rhamnoides] 

 from the flowers of Reseda luteola from 

 Andromeda japonica; h-oidCarya tomen- 

 tosa ; from the bark of apple; from leaves 

 of the tea plant, vine, and ash; from 

 catechu, hops, and from rutin, a gluco- 

 side which is contained in the leaves of 

 rue, Ruta graveoleus. 



Quercetin occurs also in flowers of 

 Capparis spinosa, in safflower, in rose 

 leaves, and leaves of buckwheat, Poly- 

 gonum fagopyrum. The colouring-matter 

 sophorin from Chinese berries, from 

 Sopkora japonica, may contain the 

 quercetin complex in the form of a 

 glucoside. 



NOTE : Quercetin exists in the above plants 

 sometimes free, but more generally in the form 

 of the glucosides querfeitrin, rutin, robinin, &c. 



According to Schmidt and Waljaschko (Ch. 

 Centr. 1901, 2, 121) the rutin from common 

 rue is not identical with robinin or quercitrin, 

 but resembles the glucoside from capers and 

 from Viola tricolor (violaquercitrin ? : see below). 

 For details of distribution of these colouring- 

 matters and glucosides see ' Die Glykoside,' by 

 Van Rijn, 1900, and ' Die Chemie der iiatiir- 

 lichen Farbstoffe,' by Hans Kupe, 1900. 



Quercetin occurs also as the glucoside 

 osyritrin or myrticolorin in Cape sumach 

 from the leaves of Colpoon compressum 

 (A. G. Perkin, Trans. Ch. Soc. 71, 

 1132), and in the leaves of Eucalyptus 

 macrorrltyncha (Smith, Trans. Ch. Soc. 

 73, 697 ; A. G. Perkin, Proc. Ch. Soc. 

 18, 58), and in Viola tricolor variensis 

 as the glucoside violaquercitrin (Man- 

 delin, Jahresber. 1883, 1369 : accord- 

 ing to A. G. Perkin, Trans. Ch. Soc. 

 81, 477, violaquercitrin, myrticolorin, 

 and osyritrin are identical). 



The presence of quercetin in catechu 

 from Uncaria (Nauclea} gambler and 

 Acacia catechu (Lowe, Zeit. anal. Ch. 

 12, 134) has been confirmed by A. G. 

 Perkin (Trans. Ch. Soc. 71, 1135), and 

 its existence in the colouring- matters 

 from the yellow wallflower, Cheiranthus 

 cheiri, from white hawthorn flowers, 

 Cratagus oxyacantha, and from Rum ex 

 ol/tusifoliiis, shown by the same author 

 (loc. cit. 69, 1566; 15/0; 71, 1199). 



The yellow colouring-matter of In- 

 dian and American podophyllum from 

 Podopliyllum emodi and P. peltatum is 

 quercetin (Dunstan and Henry, Ibid. 

 73, 22i); the dyestuff from the Indian 

 Delphinium zalil also contains a glu- 

 coside of quercetin (A. G. Perkin and 

 Pilgrim, Ibid. 273). 



A colouring-matter from the leaves 

 and stem of Tanmris gallica and T. 

 africana is a methylquercetin (A. G. 

 Perkin and Wood, Ibid. 380); the 

 leaves of Aifanthus glandulosa contain 

 quercetin (Ibid. 382); an isomeride of 

 quercetin exists in colouring-matters 

 from the leaves of Arctostap/iylos uva- 

 ^lrsi and from S. African ' broach leaves' 

 (Tbid. 384 ; also A. G. P. Proc. Ch. Soc. 

 14, 104; 16, 45; Trans. 77, 425)- 



Quercetin is contained in the leaves 

 of R/iiif; rliod anthem a from N. S. 

 Wales (A. G. P. Trans. Ch. Soc. 73, 

 1018); in common ling or heather, 



