DE1011870B - Process for the preparation of the sodium salt of lactose triphosphoric acid ester - Google Patents

Description

Process for the preparation of the sodium salt of the lactose triphosphoric acid ester The invention relates to the preparation of the sodium salt of the lactose triphosphoric acid ester by the action of phosphorus oxychloride on lactose in the presence of pyridine and subsequent neutralization with sodium hydroxide solution.

According to the invention, the procedure is that the phosphorus oxychloride act on the lactose at temperatures below 0 ° in the presence of pyridine leaves, the temperature is then increased to about 0 ° and the mixture at this temperature Can linger for a long time, whereupon the reaction mixture is stirred continuously heated and the pyridine is removed by distillation under vacuum. The dry residue is then taken up with ice, neutralized with sodium hydroxide solution and finally filtered. The sodium salt of the ester obtained in this way is precipitated with alcohol and against flowing Dialyzed water, followed by repeated precipitation and drying under vacuum connects.

There are processes for the production of phosphoric acid esters of carbohydrates and polyhydric alcohols already become known, which consist in it. that he these treated with phosphorus pentoxide in the presence of tertiary bases, while one according to even older proposals, the phosphoric acid esters of carbohydrates and polyvalent ones Alcohols were obtained by adding phosphorus oxychloride to the aqueous solutions let act of glucose or cane sugar in the presence of lime or chalk. Man the lime salt of the phosphoric acid ester, which is insoluble in alcohol, is obtained in this way must precipitate from the concentrated reaction liquid with alcohol. This lime salt is contaminated with large amounts of calcium chloride, which can only be obtained by repeating it Can remove precipitating and washing with alcohol.

In the case of levulose, milk sugar and maltose, the removal of calcium chloride is essential but practically impossible because there are constant compounds of the phosphoric acid ester and calcium chloride form. In contrast, according to the new way of working, the Sodium salt of the lactose triphosphoric acid ester obtained, the more soluble and less is more poisonous than the corresponding lime salt.

The corresponding barium salt already shown is therapeutic completely unusable because of its toxicity.

Embodiment 1 kg of lactose with a melting point of 211 ° is used during Dried under vacuum at 80 ° for 12 hours, then carefully protected from moisture Suspended protected in 101 anhydrous pyridine with stirring and then this Suspension cooled to -30 °. Thereupon one leaves slowly 0.5 l of phosphorus oxychloride drop in and the temperature rise to 0 °, at which the mixture 90 Left for minutes. The mixture is then heated to 40 ° with stirring for 12 hours and the pyridine is distilled off under vacuum at 60 ° to dryness, the residue taken up with ice, neutralized with 40% sodium hydroxide solution, filtered and the Sodium salt precipitated with alcohol. Then dialyze against fluids for 48 hours Water, precipitates again and dries again in vacuo at 60 °.

This is obtained in the form of a brown, odorless and tasteless powder the sodium salt of lactose triphosphoric acid ester with a content of 13.1% phosphorus, corresponding to the formula C12 Hls 0ll (Na2 P 03) 3 with a molecular weight of 714.31.

This ester, injected into a lipemic animal, shows a significant one antilipaemic effect. This anti-lipaemic effect is also shown by a Transmission percentage increase on the Beckmann spectrophotometer, according to the technique Seifters working. A lipemic dog plasma is mixed with mouse plasma, the was treated with the ester, then kept in a thermostat at 22 ° and then on the Beckmann the percentage of transmission at the moment of the union of the both plasmas and read a few hours later.

The sodium salt of the ester, which has no anticoagulant effect, is the first synthetic product that, because of its anti-lipaemic effect, is used for healing purposes can be used.

Claims (1)

PATENT CLAIM.- - Process for the preparation of the sodium salt of lactose triphosphoric acid ester, characterized in that lactose is treated with phosphorus oxychloride in the presence of pyridine at temperatures below -0 °, then the reaction mixture is kept at 0 ° for some time, then heated with stirring, the pyridine Distilled off to dryness, the residue neutralized with sodium hydroxide solution, filtered, the sodium salt is precipitated with alcohol, dialyzed against water, reprecipitated and dried. Documents considered: German Patent No. 484 356; Micheel, Chemie der Zucker und Polysaccharide, 1939, p. 150; Reports of the German Chemical Society, 47, p.3195 (1914).