DE151036C - - Google Patents
Info
- Publication number
- DE151036C DE151036C DENDAT151036D DE151036DA DE151036C DE 151036 C DE151036 C DE 151036C DE NDAT151036 D DENDAT151036 D DE NDAT151036D DE 151036D A DE151036D A DE 151036DA DE 151036 C DE151036 C DE 151036C
- Authority
- DE
- Germany
- Prior art keywords
- arbutin
- monobenzoylarbutine
- parts
- benzoyl chloride
- water
- 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.)
- Active
Links
- BJRNKVDFDLYUGJ-RMPHRYRLSA-N ARBUTIN Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC=C(O)C=C1 BJRNKVDFDLYUGJ-RMPHRYRLSA-N 0.000 claims description 14
- 229960000271 Arbutin Drugs 0.000 claims description 8
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 230000001264 neutralization Effects 0.000 claims description 2
- 230000005591 charge neutralization Effects 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 210000004369 Blood Anatomy 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000006480 benzoylation reaction Methods 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L Barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 210000004211 Gastric Acid Anatomy 0.000 description 1
- 210000002784 Stomach Anatomy 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 238000002844 melting Methods 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
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
Vom medizinischen Standpunkte aus erscheint es von großem Werte, eine Verbindung des Arbutins herzustellen, in welcher es nicht den intensiv bitteren Geschmack hat, nicht schon im Magen von der Magensäure zersetzt wird, sondern in das Blut übertritt, aber vom Blute in die Komponenten zerlegt und nun dasArbutin, event, auch der andere ' Teil der Verbindung, in Wirksamkeit tritt.From a medical standpoint, it appears of great value, a connection of arbutin, in which it does not have the intensely bitter taste, is not broken down by the gastric acid in the stomach, but passes into the blood, but broken down into the components by the blood and now the arbutine, event, also the other 'Part of the connection that comes into effect.
ίο Es ist bereits bekannt, daß durch Einwirkung von Benzoylchlorid auf Arbutin Pentabenzoylarbutin entsteht.ίο It is already known that by acting from benzoyl chloride to arbutin pentabenzoylarbutin is formed.
Nach dem bekannten Verfahren zur Benzoylierung von Glykosiden, im besonderen auch des Arbutins, läßt man das Benzoylchlorid im Überschuß auf das Glykosid einwirken; abgesehen von einer teilweisen Zersetzung des Arbutins bei Benzoylierung desselben nach diesem Verfahren entsteht hierbei die Pentaverbindung. Wird aber die Reaktion so geleitet, daß das Arbutin im Überschuß ist und daß die Reaktionsflüssigkeit neutral ist, so entsteht Monobenzoylarbutin.According to the known process for the benzoylation of glycosides, in particular also of arbutin, the benzoyl chloride is allowed to act in excess on the glycoside; apart from a partial decomposition of the arbutine on benzoylation of the same after this process creates the penta compound. But if the reaction is directed that the arbutin is in excess and that the reaction liquid is neutral, so monobenzoylarbutine is formed.
Das Verfahren zur Herstellung von Monobenzoylarbutin ist hiernach folgendes:The procedure for making monobenzoylarbutine is as follows:
Etwa 22 Teile Arbutin werden in Wasser gelöst und nach und nach mit 8 bis 10 Teilen Benzoylchlorid vermischt, und zwar so, daß Benzoylchlorid unter Schütteln in kleinen Mengen zugesetzt und die Mischung jedesmal 40 Approximately 22 parts of arbutin are dissolved in water and gradually mixed with 8 to 10 parts of benzoyl chloride in such a way that benzoyl chloride is added in small amounts with shaking and the mixture 40 each time
mit Alkali neutralisiert wird, damit keine freie Salzsäure entsteht.neutralized with alkali so that no free hydrochloric acid is formed.
Die Verbindung Monobenzoylarbutin fällt als weißes Pulver aus. Der Niederschlag wird gesammelt, gewaschen und getrocknet. Behufs Reinigung wird der Körper durch Kochen mit Wasser gelöst; beim Erkalten scheidet er sich in feinen Nadeln wieder aus; Monobenzoylarbutin ist in kaltem Wasser schwer löslich.The compound monobenzoylarbutine precipitates out as a white powder. The precipitation is collected, washed and dried. The body becomes through for purification Boiling dissolved with water; when it cools down, it separates out again in fine needles; Monobenzoylarbutine is sparingly soluble in cold water.
Das so erhaltene Monobenzoylarbutin ist fast geschmacklos; es wird bei Einwirkung von Alkalien, auch von Baryt und Magnesia, leicht verseift. Hieraus folgt die leichte Spaltbarkeit der Monoverbindung im Körper, welche für die medizinische Verwendung und Wirkung von Bedeutung ist. Das Monobenzoylarbutin löst sich in 1300 Teilen Wasser von 150, in 1800 Teilen von 90 und in 80 Teilen von ioo°. Der Schmelzpunkt des Körpers liegt bei 184,5° C.The monobenzoylarbutin thus obtained is almost tasteless; it is easily saponified when exposed to alkalis, including barite and magnesia. From this follows the easy cleavage of the mono-compound in the body, which is important for medical use and effectiveness. The Monobenzoylarbutin dissolves in 1300 parts of water of 15 0, in 1,800 parts of 9 and 0 in 80 parts of ioo °. The melting point of the body is 184.5 ° C.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE151036C true DE151036C (en) |
Family
ID=417889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT151036D Active DE151036C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE151036C (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10729664B2 (en) | 2009-07-10 | 2020-08-04 | President And Fellows Of Harvard College | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
| US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10786485B1 (en) | 2019-03-11 | 2020-09-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10842798B1 (en) | 2019-11-06 | 2020-11-24 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10927096B2 (en) | 2019-03-11 | 2021-02-23 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
| US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10934263B2 (en) | 2019-03-11 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11021443B2 (en) | 2015-08-03 | 2021-06-01 | President And Fellows Of Harvard College | Charged ion channel blockers and methods for use |
| US11332446B2 (en) | 2020-03-11 | 2022-05-17 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11377422B2 (en) | 2019-03-11 | 2022-07-05 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
-
0
- DE DENDAT151036D patent/DE151036C/de active Active
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10729664B2 (en) | 2009-07-10 | 2020-08-04 | President And Fellows Of Harvard College | Permanently charged sodium and calcium channel blockers as anti-inflammatory agents |
| US11021443B2 (en) | 2015-08-03 | 2021-06-01 | President And Fellows Of Harvard College | Charged ion channel blockers and methods for use |
| US11512058B2 (en) | 2019-03-11 | 2022-11-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10780083B1 (en) | 2019-03-11 | 2020-09-22 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10786485B1 (en) | 2019-03-11 | 2020-09-29 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10828287B2 (en) | 2019-03-11 | 2020-11-10 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11643404B2 (en) | 2019-03-11 | 2023-05-09 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
| US10927096B2 (en) | 2019-03-11 | 2021-02-23 | Nocion Therapeutics, Inc. | Ester substituted ion channel blockers and methods for use |
| US10934263B2 (en) | 2019-03-11 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11603355B2 (en) | 2019-03-11 | 2023-03-14 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11377422B2 (en) | 2019-03-11 | 2022-07-05 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10933055B1 (en) | 2019-11-06 | 2021-03-02 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US10842798B1 (en) | 2019-11-06 | 2020-11-24 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11696912B2 (en) | 2019-11-06 | 2023-07-11 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
| US11332446B2 (en) | 2020-03-11 | 2022-05-17 | Nocion Therapeutics, Inc. | Charged ion channel blockers and methods for use |
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