The free alkaloid is strongly laevo-rotatory.
The natural (laevo) base is twice as toxic as the dextro.
All albumins are laevo-rotatory; and on incineration a small amount of inorganic ash is invariably left.
The name is applied in commerce to a complex mixture of carbohydrates obtained by boiling starch with dilute mineral acids; in chemistry, it denotes, with the prefixes d, 1 and d+l (or i), the dextro-rotatory, laevo-rotatory and inactive forms of the definite chemical compound defined above.
The inactive mixture may be resolved into its active components by fractional crystallization of the cinchonine salt, when the salt of the dextro modification separates first; or the ammonium salt may be fermented by Penicillium glaucum, when the laevo form is destroyed and the dextro form remains untouched; on the other' hand, Saccharomyces ellipsoideus destroys the dextro form, but does not touch the laevo form.
It was surmised that a-acrose was a mixture of dextro and laevo fructose, a supposition which was proved correct by an indirect method.
Also Kiliani found that the lactone derived from the cyanhydrin of natural arabinose (laevo) was identical with the previous lactone except that its rotation was equal and opposite.
Similarly the 1 acid yields the laevo derivatives.
The identity of the formulae and osazones of d-mannose and d-glucose showed that the stereochemical differences were situated at the carbon atom adjacent to the aldehyde group. Fischer applied a method indicated by Pasteur in converting dextro into laevo-tartaric acid; he found that both d-mannonic and d-gluconic acids (the latter is yielded by glucose on oxidation) were mutually convertible by heating with quinoline under pressure at 140°.
Fischer's a-acrose therefore led to the synthesis of the dextro and laevo forms Gf mannose, glucose and fructose; and these substances have been connected synthetically with many other sugars by means of his cyanhydrin process, leading to higher sugars, and Wohl and.
As there is no means of distinguishing between the configuration of a dextroand laevo-modification, an arbitrary assumption must be made.
Since the acid contains an asymmetric carbon atom, it can exist in three forms, a dextro-rotatory, a laevo-rotatory and an inactive form; the acid obtained in the various synthetical processes is the inactive form.
It is obtained by hydrolysing cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198° to 199° C. It is laevo-rotatory, and on warming with alkalis gives iso-ecgonine, which is dextro-rotatory.
Four acids of this composition are known, namely dextroand laevo-tartaric acids, racemic acid and mesotartaric acid, the two last being optically inactive (see Stereo-Isomerism).
Laevo-tartaric acid is identical in its chemical and in most of its physical properties with the dextro-acid, differing chiefly in its action on polarized light, the plane of polarization being rotated to the left.
The acid solution of sulphate of quinine is fluorescent, especially when dilute; and it is laevo-rotatory.
The other alkaloids are distinguished from quinine thus: quinidine resembles quinine, but is dextro-rotatory, and the iodide is very insoluble in water; the solution of cinchonidine, which is laevo-rotatory, does not give the thalleoquin test, nor fluorescence; cinchonine resembles cinchonidine in these respects, but is dextrorotatory.
The fourth isomer, formed by the action of Bacillus laevo-lacti on cane-sugar, resembles sarcolactic acid in every respect, except in its action on polarized light (see Stereoisomerism).
The a-propyl piperidine so obtained is the inactive (racemic) form of conine, and it can be resolved into the dextroand laevo-varieties by means of dextro-tartaric acid, the d-conine d-tartrate with caustic soda giving d-conine closely resembling the naturally occurring alkaloid.