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Encyclopedia Britannica



BERBERINE, CBH17NO4

This article appears in Volume V03, Page 764 of the Encyclopedia Britannica.

Encyclopedia Britannica - Main :: BEC-BER
BERBERINE, CBH17NO4 , an alkaloid occurring together with the alkaloids oxyacanthine C16H19NO3, berbamine C13H19NO3, hydrastine C21H21N06, and canadine C20H21NO4, in Berberis vulgaris; it also occurs in other
plants
 , Berberis aristata, B. aquifolium, Hydrastis canadensis, &c. It is a yellow, crystalline solid, insoluble in
ether
  and chloroform, soluble in 41 parts of water at 2 1, and moderately soluble in
alcohol
 . It is a monacid
base
 ; the hydrochloride, C2BH17NO4HCI, is insoluble in cold
alcohol
 ,
ether
  and chloroform, and soluble in 500 parts of water; the acid sulphate, C20H17N04112SO4, dissolves in about loo parts of water. Canadine is a tetrahydroberberine.
Its constitution was worked out by W. H.
Perkin
  (J.C.S., 1889, 55, p. 63; 189o, 57, p. 991). This followed from a study of the decomposition products, there being obtained hemipinic acid (CH3O)2C6H2(000H)2, and a substance which proved to be to- amino -
ethyl
 - piperonyl carboxylic acid, CH2O2:C6H2COOHCH2CH2NH2. His
formula
  was modified by Gadamer (Abs. J.C.S., 1902, I, p. 555), who made the free
base
  an aldehyde, but the salts of an iso-quinolinium type. This
formula
 , which necessitates the presence of two asymmetric carbon atoms in an alkyl tetrahydroberberine, has been accepted by M. Freund and F. Mayer (Abs. J.C.S., 1907, I, p. 632), who showed that two racemic propyl tetrahydroberberines are produced when propyl dihydroberberine is reduced.


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