DE1039194B - Process for the production of 1,4-dicaffeeylquinic acid - Google Patents
Process for the production of 1,4-dicaffeeylquinic acidInfo
- Publication number
- DE1039194B DE1039194B DES54976A DES0054976A DE1039194B DE 1039194 B DE1039194 B DE 1039194B DE S54976 A DES54976 A DE S54976A DE S0054976 A DES0054976 A DE S0054976A DE 1039194 B DE1039194 B DE 1039194B
- Authority
- DE
- Germany
- Prior art keywords
- plants
- genus
- acid
- family
- foeniculum
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 239000002253 acid Substances 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title description 4
- 241000196324 Embryophyta Species 0.000 claims description 12
- 241000208947 Cynara Species 0.000 claims description 9
- 235000003198 Cynara Nutrition 0.000 claims description 9
- 238000000605 extraction Methods 0.000 claims description 9
- 241000208838 Asteraceae Species 0.000 claims description 7
- 241000212314 Foeniculum Species 0.000 claims description 4
- 235000011173 Foeniculum vulgare subsp piperitum Nutrition 0.000 claims description 4
- 241000824740 Foeniculum vulgare subsp. piperitum Species 0.000 claims description 4
- 240000006927 Foeniculum vulgare Species 0.000 claims description 2
- 235000004204 Foeniculum vulgare Nutrition 0.000 claims description 2
- 241000132519 Galactites Species 0.000 claims description 2
- 241000320349 Onopordum Species 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 244000019459 Cynara cardunculus Species 0.000 description 3
- 235000019106 Cynara scolymus Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 101100495769 Caenorhabditis elegans che-1 gene Proteins 0.000 description 1
- 244000272323 Cirsium lanceolatum Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 240000005687 Scolymus hispanicus Species 0.000 description 1
- 235000018520 Scolymus hispanicus Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000016520 artichoke thistle Nutrition 0.000 description 1
- 150000001553 barium compounds Chemical class 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 229940056932 lead sulfide Drugs 0.000 description 1
- 229910052981 lead sulfide Inorganic materials 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/28—Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/216—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acids having aromatic rings, e.g. benactizyne, clofibrate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/23—Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
- A61K36/235—Foeniculum (fennel)
Landscapes
- Health & Medical Sciences (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Alternative & Traditional Medicine (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Medical Informatics (AREA)
- Botany (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Emergency Medicine (AREA)
- Medicines Containing Plant Substances (AREA)
- Cosmetics (AREA)
Description
Verfahren zur Gewinnung von 1 ,4-Dikaffeeyld.inasäure Zusatz zur Patentanmeldung F 17482 IVa/30h (Auslegeschrift 1 030 514) Die Patentanmeldung F 17482 INTa/30h betrifft ein Verfahren zur Gewinnung der 1,4-Dikaffeeylchinasäure, welche eine hervorragende physiologische Wirksamkeit als Anregungsmittel der Galleabsonderung und des Cholesterinstoffwechsels besitzt. Zu diesem Zweck werden wäßrige Extrakte von Pflanzen, die, wie z. B. Disteln (Cynara cardunkulus) oder Artischocken (Cynara scolymus), diese Säure enthalten, mit einem Überschuß von wäßrigen Lösungen der 131ei- oder Bariumverbindungen in der Kälte oder Wärme versetzt, und die 1,4-Dikaffeeylchinasäure wird durch Versetzen des entstandenen Niederschlages mit sauren Agentien von den Verunreinigungen selektiv abgetrennt. Process for the production of 1, 4-Dikaffeeyld.inasäure additive for Patent application F 17482 IVa / 30h (Auslegeschrift 1 030 514) The patent application F 17482 INTa / 30h relates to a process for the production of 1,4-dicaffeeylquinic acid, which has excellent physiological activity as a stimulant of bile secretion and cholesterol metabolism. Aqueous extracts are used for this purpose of plants that, e.g. B. thistles (Cynara cardunkulus) or artichokes (Cynara scolymus), containing this acid, with an excess of aqueous solutions of the 131 egg or barium compounds are added in the cold or heat, and 1,4-dicaffeeylquinic acid is obtained by adding acidic agents to the resulting precipitate Selective separation of impurities.
Cynara carcunculus und Cynara scolymus gehören zur Familie der Compositae, Unterfamilie Tubiflorales, Gattung Cynara. Cynara carcunculus and Cynara scolymus belong to the Compositae family, Subfamily Tubiflorales, genus Cynara.
Es wurde nun gefunden, daß auch andere Pflanzen der gleichen Gattung der Cynarae 1,4-Dikaffeeylchi nasäure enthalten und als Ausgangsmaterial für die Extraktion dieser Säure verwendet werden können, z. B. Onopordon illyricum, Scolymus hispanicus und Lupsia galactites. It has now been found that other plants of the same genus the Cynarae contain 1,4-Dikaffeeylchi nasäure and as a starting material for the Extraction of this acid can be used, e.g. B. Onopordon illyricum, Scolymus hispanicus and Lupsia galactites.
Ferner wurde gefunden, daß außer den Pflanzen der Gattung Cynara, Familie Compositae (Unterfamilie Tubiflorales), weitere Pflanzen als Ausgangsmaterial für die Extraktion von 1,4-Dikaffeeylchinasäure nach dem in der Hauptpatentanmeldung besch,riebenen Verfahren dienen können, und zwar von der Gattung Foenicolum aus der Familie der Umbelliflorae, z. B. It was also found that, in addition to the plants of the genus Cynara, Family Compositae (subfamily Tubiflorales), other plants as starting material for the extraction of 1,4-dicaffeeylquinic acid according to that in the main patent application dam, can serve as a method, namely from the genus Foenicolum the Umbelliflorae family, e.g. B.
Foeniculum vulgare und Foeniculum piperitum.Foeniculum vulgare and Foeniculum piperitum.
Das zur Anwendung gelangende Extraktionsverfahren entspricht demjenigen der Hauptpatentanmeldung. The extraction process used corresponds to that the main patent application.
Bezüglich der Einzelheiten des Extraktionsverfahrens sei auf die Hauptpatentanmeldung verwiesen. Im folgenden Beispiel wird als Ausgangsmaterial Foeniculum piperitum verwendet, doch sei betont, daß das gleiche Verfahren auch auf andere, die 1,4-Dikaffeeylchinasäure enthaltende Pflanzen der Gattung Foeniculum, Familie Umbelliflorae, oder der Gattung Cynara, Familie Compositae (Unterfamilie Tubiflorales), angewendet werden kann. Regarding the details of the extraction process, refer to Main patent application referenced. In the following example, the starting material is Foeniculum piperitum is used, but it should be emphasized that the same procedure is also used to other plants of the genus Foeniculum containing 1,4-dicaffeeylquinic acid, Family Umbelliflorae, or the genus Cynara, Family Compositae (subfamily Tubiflorales), can be used.
Beispiel 2 kg Foeniculum piperitum (oberirdische Teile der frischen Pflanze) werden mit 101 Wasser 6 Stunden lang auf Siedetemperatur erhitzt. Der Absud wird abgekühlt, filtriert und mit etwa 100 ccm einer gesättigten Lösung von neutralem Bleiacetat behandelt. Die ausgefällten Bleisalze werden abzentrifugiert, gewaschen und in 100 ccm 406/obiger Essigsäure, welche mit 100 ccm Wasser verdünnt ist, suspendiert. Die Suspension wird auf Siedetemperatur erhitzt, zur Abtrennung des nicht gelösten Anteils auf dem Büchner-Filtertrichter warm filtriert und der Rückstand mit siedendem Wasser gewaschen, worauf man das Filtrat mit Hilfe von Schwefelwasserstoff von Blei befreit. Example 2 kg Foeniculum piperitum (aerial parts of the fresh Plant) are heated to boiling temperature with 101 water for 6 hours. The decoction is cooled, filtered and with about 100 ccm of a saturated solution of neutral Treated lead acetate. The precipitated lead salts are centrifuged off and washed and suspended in 100 ccm 406 / acetic acid above, which is diluted with 100 ccm water. The suspension is heated to boiling temperature to separate the undissolved Share on the Büchner filter funnel filtered warm and the residue with boiling Washed with water, whereupon the filtrate was removed with the aid of hydrogen sulfide from lead freed.
Das Bleisulfid wird auf dem Büchner-Trichter abfiltriert und mit siedendem Wasser gewaschen, und das Filtrat wird im Vakuum auf etwa 40 ccm konzentriert.The lead sulfide is filtered off on the Büchner funnel and mixed with boiling Washed water and the filtrate is concentrated in vacuo to about 40 cc.
Beim Stehenlassen scheidet sich ein weißer Feststoff ab, welcher isoliert und getrocknet wird. Sein Gewicht beträgt 3 g. Durch Kristallisieren aus Wasser erhält man 0,2g 1,4-Dikaffeeylchinasäure, Schmelzpunkt 227 bis 2280 C (rasches Erhitzen), spezifische Drehung [a] D68 D -68 +10 (C = 2,0; Äthanol). A white solid separates out on standing, which is isolated and dried. Its weight is 3 g. By crystallizing out Water, 0.2 g 1,4-dicaffeeylquinic acid is obtained, melting point 227 to 2280 C (rapid Heating), specific rotation [a] D68 D -68 +10 (C = 2.0; ethanol).
PATENTANSPR(=CHE 1. Verfahren zur Gewinnung von 1,4-Dikaffeeylchinasäure nach Patentanmel dung F 17482 IVa/30 h, dadurch gekennzeichnet, daß als Ausgangsmaterial Pflanzen von der Gattung Cynara, Unterfamilie Tubiflorales, Familie Compositae, oder solche der Gattung Foeniculum, Familie Umbelliflorae, verwendet werden. PATENT APPLICATION (= CHE 1. Process for the production of 1,4-dicaffeeylquinic acid according to patent application F 17482 IVa / 30 h, characterized in that the starting material Plants of the genus Cynara, subfamily Tubiflorales, family Compositae, or those of the genus Foeniculum, family Umbelliflorae, can be used.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1039194X | 1956-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1039194B true DE1039194B (en) | 1958-09-18 |
Family
ID=11429645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES54976A Pending DE1039194B (en) | 1956-09-06 | 1957-09-03 | Process for the production of 1,4-dicaffeeylquinic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1039194B (en) |
-
1957
- 1957-09-03 DE DES54976A patent/DE1039194B/en active Pending
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