DE123099C - - Google Patents
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- Publication number
- DE123099C DE123099C DENDAT123099D DE123099DA DE123099C DE 123099 C DE123099 C DE 123099C DE NDAT123099 D DENDAT123099 D DE NDAT123099D DE 123099D A DE123099D A DE 123099DA DE 123099 C DE123099 C DE 123099C
- Authority
- DE
- Germany
- Prior art keywords
- product
- insoluble
- preparation
- derivatives
- acidylating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 7
- SMQUZDBALVYZAC-UHFFFAOYSA-N Salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims 3
- 239000000155 melt Substances 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 230000002421 anti-septic Effects 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229960000583 Acetic Acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N Acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 210000004051 Gastric Juice Anatomy 0.000 description 1
- 210000000936 Intestines Anatomy 0.000 description 1
- 210000002784 Stomach Anatomy 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000003260 anti-sepsis Effects 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- -1 diacetyl compound Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000000968 intestinal Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 231100000486 side effect Toxicity 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
KLASSEGREAT
In der Patentschrift' 117890 ist ein Product beschrieben, welches durch Einwirkung von 2 Mol. Resorcin auf 1 Mol. Halogenmethylsalicylaldehyd erhalten wird und welches wir in Folgendem als Diresorcylmethylensalicylaldehyd bezeichnen wollen.In the '117890 patent, there is a Product described, which by the action of 2 mol. Resorcinol on 1 mol. Halomethylsalicylaldehyde and which we will refer to as diresorcylmethylene salicylaldehyde in the following.
Dieses Präparat hat sich mit Rücksicht auf seine adstringirenden und antiseptischen Eigenschaften als werthvolles externes Antisepticum erwiesen. Einer internen Anwendung des Productes, speciell für die Zwecke der Darmantisepsis, stand jedoch bisher der überaus schlechte, zusammenziehende Geschmack im Wege.This preparation has been developed with regard to its astringent and antiseptic properties Proven as a valuable external antiseptic. An internal application of the Productes, especially for the purposes of intestinal antisepsis, has hitherto been used by the extreme bad, astringent taste in the way.
Es hat sich nun ergeben, dafs sich dieser Mangel ohne Aufhebung der erwähnten werthvollen Eigenschaften dadurch beheben läfst, dafs man das Product durch Einwirkung acidylirender Agentien, wie Essigsäureanhydrid, Acetylchlorid, Propionylchlorid u. s. w. acidylirt. Dabei entstehen je nach der Menge des angewendeten Acidylirungsmittels verschiedene Säurederivate, welche sich im Wesentlichen durch ihre Löslichkeit in Soda. unterscheiden, und zwar nimmt diese mit steigender Zahl der eingeführten Acidylgruppen ab, so dafs z. ß. der Körper, welchen man durch Behandeln des Ausgangsproductes mit einem Ueberschufs von Essigsäureanhydrid erhält, in Soda völlig unlöslich ist, während derjenige Körper, welcher bei Einwirkung von 1 Mol. Essigsä'ureanhydrid beim Kochen in eisessigsaurer Lösung erhalten wird, als leicht löslich in einprocentiger Sodalösung sich erweist. Die so erhältlichen Säurederivate weisen sämmtlich den Vorzug auf, geschmacklos und im Magensaft unlöslich.zu sein, so dafs sie den Magen unverändert passiren und erst im Darm gespalten werden, wobei mit der Rückbildung des nicht acidylirten Productes die werthvollen antiseptischen Eigenschaften jenes Productes in vollem Umfange ohne unangenehme Nebenwirkung auf den übrigen Organismus in Wirkung treten. Am praktischsten für die medicinische Anwendung erwiesen sich dabei die niedrig acidylirten, in Soda leicht löslichen Derivate, weil dieselben am raschesten gespalten werden und die antiseptische Wirkung bei ihnen daher am promptesten zu Tage tritt.It has now been found that this deficiency arises without eliminating the valuable ones mentioned Properties can be remedied by the action of acidifying the product Agents such as acetic anhydride, acetyl chloride, propionyl chloride and the like are acidylated. Depending on the amount of acidylating agent used, various acid derivatives are formed, which are mainly characterized by their solubility in soda. differ, and Although this decreases with an increasing number of acidyl groups introduced, so that z. ß. the Bodies which can be obtained by treating the starting product with an excess of Acetic anhydride is completely insoluble in soda, while the body which after the action of 1 mol. Acetic anhydride obtained when boiling in glacial acetic acid solution proves to be easily soluble in one percent soda solution. The acid derivatives obtainable in this way all have the advantage of being tasteless and insoluble in gastric juice. so that they pass through the stomach unchanged and are only split in the intestine, whereby with the regression of the unacidylated product, the valuable antiseptic properties of that product in their full extent take effect without unpleasant side effects on the rest of the organism. Most practical for medical use The low acidity derivatives, easily soluble in soda, were found, because they are the same are the quickest to split and the antiseptic effect on them is therefore most prompt comes to light.
Sehr gut bewährt sich zur Darstellung eines leicht spaltbaren, geschmacklosen Acetylproductes folgendes Verfahren:It has proven itself very well for the representation of an easily cleavable, tasteless acetyl product following procedure:
350 g Diresorcylmethylensalicylaldehyd werden fein gepulvert, mit 200 g Essigsäureanhydrid übergössen und durch Rühren zu einer dicken Paste verarbeitet. Wärmt man dann auf dem Wasserbade an, so tritt alsbald eine Reaction ein unter Steigerung der Temperatur und Verflüssigung des Gemisches. Dieses wird dann noch 1 Stunde auf dem Wasserbade erwärmt und dann in 10 1 kalten Wassers unter Umrühren einfliefsen gelassen, wobei das Acetylirungsproduct, welches nach unseren Untersuchungen hauptsächlich aus . der Diacetylverbindung besteht, in gelben Flocken ausfällt. Dasselbe wird abgesaugt, mit Wasser gewaschen und bei nicht zu hoher Temperatur getrocknet. Es bildet in getrocknetem Zustande ein feines rothgelbes Pulver, unlöslich in Wasser, leichtlöslich dagegen mit rothbrauner Farbe in ver-350 g of diresorcylmethylene salicylaldehyde are finely powdered with 200 g of acetic anhydride Poured over and processed into a thick paste by stirring. Then you warm up on the water bath, a reaction immediately takes place, with an increase in temperature and liquefaction of the mixture. This is then heated on the water bath for another hour and then allowed to flow into 10 l of cold water with stirring, the acetylation product, which, according to our investigations, mainly consists of. the diacetyl compound, precipitates in yellow flakes. The same is filtered off with suction, washed with water and dried at a temperature that is not too high. When dry it forms a fine red-yellow powder, insoluble in water, easily soluble on the other hand with a red-brown color in
Claims (1)
Verfahren zur Darstellung von in Wasser und Säuren unlöslichen, geschmacklosen Acidylderivaten des in der Patentschrift 117890 beschriebenen Diresorcylmethylensalicylaldehyds, darin bestehend, dafs man dieses Product der Einwirkung von acidylirenden Agentien unterwirft. Sponsors τ-Α ν SPRU c η:
Process for the preparation of tasteless acidyl derivatives, insoluble in water and acids, of the diresorcylmethylene salicylaldehyde described in patent 117890, consisting in subjecting this product to the action of acidylating agents.
Publications (1)
Publication Number | Publication Date |
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DE123099C true DE123099C (en) |
Family
ID=391969
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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DENDAT123099D Active DE123099C (en) |
Country Status (1)
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DE (1) | DE123099C (en) |
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