CH:N_2H.C_6H_4I | C:N_2H.C_6H_4I | CH.O.R R = CO.C_6H_2(O.CO.C_6H_6)_2 | CH.O.R | CH.O.R R R R R | O O O O | | | | | CH_2.O.CH.CH.CH.CH.CH.CH_2 | | ---O--- The molecular weight of this substance is 4,021, and probably represents the highest molecular organic body obtained in any chemical synthesis. From a physiological standpoint the recognition of tannins as esters of glucose and hydroxybenzoic acids, possessing characteristics similar to those of tannin, is of great importance. Especially interesting appears the fact of plants utilising sugars for the esterification of acids, just as glycerol or monohydric alcohols may be employed for the same purpose. Free acids, as a rule, are only tolerated in certain parts of the organism, the latter usually striving to neutralise acidic groups which may be brought about by salt formation; formation of amino compounds (proteins) or esterification (fats); and, lastly, esterformation by means of sugars. Why Nature should always build up substances of very complex constitution can only be explained by biochemical investigations, but it may, at any rate, be assumed that by this means any substance poisonous to the living organism is rendered inactive. The function of the tannins present in plants may thus be explained; if, for instance, phenols are formed by the oxidation of corresponding sugars, [Footnote: Mielke, "Ueber die Stellung der Gerbstoffe im Stoffwechsel der Pflanzen" (Hamburg, 1893).] the poisonous character of the former would be lessened by the introduction of the carbonic acid esters and subsequent coupling of the substances (depside formation). The depsides thus formed would serve as vehicle of the sugars and transport the migrating tannins, [Footnote: Kraus, "Grundlinien zu einer Physiologie der Gerbstoffe" (1889).] and, after subsequent deposition of the sugars, would then be eliminated from the plant organism, either by oxidation into ellagic acid and phlobaphenes or by condensation with the formation of cork. Diagrammatically, the following would represent the physiology of the tannins:--[Footnote: Nierenstein, "Chemie der Gerbstoffe" (Stuttgart, 1910).] Sugar-->Phenol-->Hydroxybenzoic Acid-->Depside--> |Phlobaphene -->Migrating Depside-->Glucoside-->Free Depside-->-{Ellagic Acid |Cork. [Illustration: Chart Showing the Decomposition of Products of Tannin.] SECTION II SYNTHESIS OF TANNING MATTERS 1. AROMATIC SULPHONIC ACIDS In organic chemistry distinction is made between sulphonic acids of the aliphatic and the aromatic series, the characteristic group of these acids being the so-called _sulphonic acid group_, HSO_3.