DE753133C

DE753133C - Process for the production of odorless and tasteless compounds of guaiacol with protein or protein breakdown products

Info

Publication number: DE753133C
Application number: DEK157611D
Authority: DE
Inventors: Hans P Dr Kaufmann
Original assignee: Individual
Current assignee: Individual
Priority date: 1940-05-15
Filing date: 1940-05-15
Publication date: 1952-12-15

Description

Die Anwendung des als Heilmittel wertvollen Guajacols wird dturdi seinen durchdringenden Geruch und seinen unangenehmen Geschmack sehr erschwert. Das vorliegende Verfahren will diese Nachteile dadurch, beheben, daß Guajacol mit solchen Verbindungen chemisch vereinigt wird, die im Darm verdaut werden, wahrend Guajacol in Freiheit gesetzt wird. Dazu eignen sich, wie gefunden wurde, Eiweißstoffe und Eiweißspaltprodukte, die nicht nur physiologisch indifferent sind, sondern vom Körper leicht abgebaut werden.The use of guaiacol, which is valuable as a remedy, becomes dturdi its pervasive Smell and its unpleasant taste very difficult. The present The method aims to remedy these disadvantages by using guaiacol with such compounds is chemically combined, which are digested in the intestine, while guaiacol is set free will. As has been found, proteins and protein breakdown products are suitable for this purpose are not only physiologically indifferent, but are easily broken down by the body.

Es wurde gefunden, daß es gelingt, durch Umsetzung des^! aus Guajacol erhältlichen Guajacolkohlensäurechlorids mit Stoffen der vorgenannten Art Arzneimittel zu schaffen, die völlig geruch- und geschmacklos sind. Im Darmsaft zerfallen sie jedoch;. Während die verdauliche Komponente verschwindet, entfaltet sich die Heilwirkung des Guajacols.It has been found that it is possible to implement the ^! to create guaiacol carbonic acid chloride obtainable from guaiacol with substances of the aforementioned type drugs which are completely odorless and tasteless. However, they disintegrate in the intestinal juice. While the digestible component disappears, the medicinal properties of guaiacol unfold.

Derartige neue Stoffe entstehen durch Umsetzung der Komponenten unter Abspaltung von Salzsäure, und zwar besonders vorteilhaft bei Gegenwart säurebindender Mittel,Such new substances are created by converting the components and splitting them off of hydrochloric acid, particularly advantageous in the presence of acid-binding agents,

Claims

such as pyridine, or when using the alkali compounds, each with guaiacol carbonic acid cfaloride substances to be converted.

Sodium lysalbinate, mixed with guaiacol carbonic acid chloride while cooling with ice, When properly worked up, it produces an amorphous powder, bound guaiacol contains. Casein, mixed with pyridine, forms an odorless and odorless with the chloride

ίο tasteless powder, the guaiacol content of which depends on the proportions of the starting materials. The complexity of the structure of the protein bodies makes it impossible to obtain clearly characterized substances. This is achieved by using the building blocks of proteins, the amino acids. If you solve z. B. Glycocolla in water, neutralized with sodium hydroxide solution and shaken in the cold with guaiacol carbonic acid chloride, so you get the carbo- ^{melting at 15S 0} with appropriate workup. gua j acoxyglykokol 1:

NH, ■ GH., • COOH +

-OCH ₃

- Ο. CO Cl

= HCl

-OCH ₃

- O-CO-NH-CH., - COOH

From the patent specification 162 656 are from guaiacol and egg white by heating to 115 to 120 ° available products known. However, these contain guaiacol in such a way that it can be split off easily Form that they smell and taste of it. One relatives instead of protein its primary As our own experiments have shown, hydrolysis products `` emerged '' later, a dissolving one resinous mass, while amino acids did not react at all.

From the patent 680 879 is the implementation of chlorocarbonic acid esters of Alcohols with protein products are known. About the chemistry of the unfolding Reactions are not communicated. The chlorocarbonic acid esters of phenols, so that too Guaiacol carbonic acid chloride, but behave, for example with regard to their cleavage, often different. The patent specification does not contain any information on therapeutic properties of the products.

Examples

.1. S parts will be sodium lysalbimate dissolved in water and under Eiskühktng with 3 parts guaiacol carbonic acid chloride up to Disappearance of the same implemented. Then you acidify weakly, evaporate in vacuo carefully to dryness and takes off with Metharvol. The solution obtained is concentrated, filtered and falls with ether. The amorphous product obtained contains about 10% bound Guaiacol.

2. Dissolve 15 parts of protalbic acid in water with the addition of tertiary sodium phosphate, cool with ice water and introduce 10 parts of guaiacol carbonic acid chloride with vigorous stirring. As soon as the latter has reacted, it is precipitated with dilute hydrochloric acid, the deposited substance is nitrated, it is dissolved in methanol for purification and it is precipitated with ether. The amorphous substance that precipitates is purified again by reprecipitating it from methanol using ether and dried ^{to 40 ° C.} It contains 16% bound guaiacol.

3. 5 parts of casein and 12.5 parts of anhydrous pyridine are slowly mixed with 5 parts of guaiacol carbonic acid chloride, after which the mixture is heated ^{to 50 to 60 ° C. for several hours.} The odorless and tasteless reaction product obtained after washing with water contains 40% guaiacol.

4. 3 parts of glycocolla are dissolved in 15 parts of water, 4 parts of sodium hydroxide solution are added while cold and 8 parts of guaiacol carbonic acid chloride ^{1 are} shaken. To avoid an acidic reaction, add 2 parts of dry soda. When the reaction is complete, the mixture is made acidic, evaporated under reduced pressure and extracted with ether. The ether solution, treated with petroleum ether until the onset of turbidity, separates on standing at 158 ⁰ crystals melting of Carboguajacoxyglykokolls from. The compound obtained in exactly the same way from alanine melts at 136 ^° . Both substances are: odorless and tasteless.

100 Pa τ enta χ s ρ r γ; c η:

Process for the preparation of odorless and tasteless compounds of guaiacol with protein or protein breakdown products, characterized in that guaiacol carbonic acid chloride is used with protein or protein breakdown products.

To differentiate the subject matter of the invention from the state of the art, the granting procedure the following publications have been considered:

German patent specifications No. 162 656, 680 879.