Details are given of procedures for effecting paper ionophoresis of polyhydroxy compounds in the electrolytes borax, sodium arsenite, basic lead acetate, and sodium hydroxide. and for detecting the compounds after ionophoresis. Rates of migration are reported for 96 compounds, including all pentose and hexose sugars, the common disaccharides, all sugar alcohols up to the heptitols, the cyclitols, a number of glycols, and several glycosides and other derivatives of carbohydrates. Some new or improved reagents have been developed for locating carbohydrates on paper strips under various conditions. Sodium arsenite and basic lead acetate are the most effective electrolytes for separating reducing sugars, basic lead acetate is the best for separating sugar alcohols, and borax is the best for simple glycols. Some success has been achieved in correlating the configurations of stereoisomers with their mobilities in paper ionophoresis.

A solution containing citric acid (0.lM) and ferric chloride (0.1M) was irradiated by bright sunlight for 3 hr. The products of the photochemical reaction were examined by means of paper ionophoresis using 0.05M sodium chloride as the electrolyte. Acetone-dicarboxylic acid and acetoacetic acid separated readily and were identified by their positions on the paper and by their red-violet reactions on contact with a solution of ferric chloride sprayed onto the paper. The ferrous iron simultaneously produced during the photochemical reaction also separated during ionophoresis and was identified on the paper. The existence of an anionic citrate-ferric iron complex was demonstrated by paper ionophoresis.

Carbamates (N-carboxy derivatives) are formed when solutions of primary or secondary amino compounds in strong alkali are exposed on paper strips to carbon dioxide, and may be separated by paper ionophoresis and detected as additional, anionic components. The formation of mono-, di-, tricarbamates, and so on, from a polyamino compound occurs concurrently, and when an amino compound containing n reactive groups is submitted to paper ionophoresis in 0.lN sodium hydroxide at 18-20� after exposure to carbon dioxide, it affords n additional spots. Most primary and secondary amino groups in saturated compounds, and some aromatic amino groups, are reactive, but highly hindered amino groups are not. Some unreactive groups become reactive when the ionophoresis is conducted at 1-2�. The procedure is analytically useful, and may be used to gain information about the structure of amino compounds. The conditions favouring the formation of carbamates have been defined by paper ionophoresis. The primary reaction in the formation of carbamates is the addition of carbon dioxide to the amino nitrogen atom; carbamates are not formed directly from the carbonate ion. The rate of reaction with carbon dioxide and the stability of the carbamates may be correlated with the steric and electronic environment of the amino groups. Low temperature and high alkalinity are essential for the stability of carbamates in solution.�The "basic mercury carbamates" described by Neuberg and Kerb (Biochem. Z., 1912, 40, 498) do not seem to have the structure assigned by these authors. Dithiocarbamates obtained by reaction of amines with carbon disulphide in alkaline solution are easily identified by paper ionophoresis, but they cannot readily be formed on the paper strip. Attempts to prepare N-sulphinates by reaction of amino compounds with sulphur dioxide on paper strips have been unsuccessful.

The alkaloid previously isolated from Symphytum orientale and regarded as a diester of a new, doubly unsaturated pyrrolizidine diol with tiglic and trachelanthic acids, is shown to be a monoester of retronecine N-oxide. N.m.r. and mass spectral measurements and electrophoretic data show that the tiglic acid esterifies not the C 7- hydroxyl of the pyrrolizidine ring, but the secondary hydroxyl of the trachelanthate moiety. It is proposed that the name anadoline be given in future to the corresponding tertiary base.

Directions are given for a simple, reproducible preparation of methyl a-and methyl P-D-galactopyranoside by the Fischer method.1 The initial separation affords the two compounds, 97-9894 pure, in yields of 41 and 15% respectively. raised to about 58 and 21% by re-equilibration of the residual syrup that contains methyl galactofuranosides.The preparation of the methyl galactopyranosides has been described many times. The yields obtained by the Fischer method and the details of the separation of the pure isomers vary widely, and at least some of the published procedures have proved to be capricious and unreliable in this and other laboratories. For example, Dale and Hudson* reported a clean separation of .x and 9 isomers when the crude, syrupy mixture of methyl galactosides was dissolved in isopropyl alcohol, the a isomer separating first. as the monohydrate. In other hands,3 this caused the two pyranosides to crystallize as a mixture, and when the method w-as tried in this laboratory the P isomer separated first, but both isomers were very impure.The conflicting results were probably caused by different amounts of water in solvents, although it is possible that both isomers may exist in more than one crystalline form. The a isomer seems to crystallize only as a monohydrate. I t showed no tendency to crystallize in anhydrous form from anhydrous solvents, and no unequivocal statement that this has been achieved could be found in the literature. The monohydrate could usually be crystallized from organic solvents containing water, but the results were sometimes unpredictable. The hydrated a form did crystallize excellently from concentrated solutions in water alone,lJ and showed a remarkable power to exclude isomers and coloured impurities. The P isomer, which does not form a hydrate, shox-ed the opposite behaviour-it mas very soluble in water, but crystallized readily from anhydrous ethanol. The use of water and then ethanol as solvent provided reproducible conditions under which the two pyranosides could be isolated from the crude mixture of methyl galactosides obtained by the Fischer method. The (3 form could be isolated first,5 by using ethanol before water. The yield of P form was then lower, but the method is more convenient than the four-stage preparation6 of the (3 form through tetra-0-acety~-a-D-gda~topyranosyl