DE194810C - - Google Patents
Info
- Publication number
- DE194810C DE194810C DENDAT194810D DE194810DA DE194810C DE 194810 C DE194810 C DE 194810C DE NDAT194810 D DENDAT194810 D DE NDAT194810D DE 194810D A DE194810D A DE 194810DA DE 194810 C DE194810 C DE 194810C
- Authority
- DE
- Germany
- Prior art keywords
- thymol
- derivatives
- alcohol
- embelia
- condensing agent
- 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
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims description 24
- 239000005844 Thymol Substances 0.000 claims description 12
- 229960000790 thymol Drugs 0.000 claims description 12
- 241000843353 Embelia Species 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- IRSFLDGTOHBADP-UHFFFAOYSA-N embelin Chemical compound CCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O IRSFLDGTOHBADP-UHFFFAOYSA-N 0.000 claims description 7
- 241000220433 Albizia Species 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- RZCNBXBEOKUFOU-UHFFFAOYSA-N 2-(2-hydroxy-6-methyl-3-propan-2-ylphenyl)-3-methyl-6-propan-2-ylphenol Chemical compound CC(C)C1=CC=C(C)C(C=2C(=C(C(C)C)C=CC=2C)O)=C1O RZCNBXBEOKUFOU-UHFFFAOYSA-N 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 238000005238 degreasing Methods 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000001648 tannin Substances 0.000 claims description 2
- 229920001864 tannin Polymers 0.000 claims description 2
- 235000018553 tannin Nutrition 0.000 claims description 2
- LWIZJFXBIIFGRI-UHFFFAOYSA-N 2-hydroxybenzoic acid;5-methyl-2-propan-2-ylphenol Chemical compound OC(=O)C1=CC=CC=C1O.CC(C)C1=CC=C(C)C=C1O LWIZJFXBIIFGRI-UHFFFAOYSA-N 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 235000013399 edible fruits Nutrition 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- KFZXVMNBUMVKLN-UHFFFAOYSA-N 4-chloro-5-methyl-2-propan-2-ylphenol Chemical compound CC(C)C1=CC(Cl)=C(C)C=C1O KFZXVMNBUMVKLN-UHFFFAOYSA-N 0.000 description 1
- 208000033211 Ankylostomiasis Diseases 0.000 description 1
- 241000244186 Ascaris Species 0.000 description 1
- 241001473877 Biserrula isolate Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 240000006432 Carica papaya Species 0.000 description 1
- 235000009467 Carica papaya Nutrition 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000581652 Hagenia abyssinica Species 0.000 description 1
- 206010020376 Hookworm infection Diseases 0.000 description 1
- 241000612162 Maesa Species 0.000 description 1
- 241000612122 Myrsine Species 0.000 description 1
- 241000344049 Wallenia Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000002382 camphene group Chemical group 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- RBNWAMSGVWEHFP-UHFFFAOYSA-N trans-p-Menthane-1,8-diol Chemical compound CC(C)(O)C1CCC(C)(O)CC1 RBNWAMSGVWEHFP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE194810C true DE194810C (en:Method) |
Family
ID=457918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT194810D Active DE194810C (en:Method) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE194810C (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5542683A (en) * | 1994-07-27 | 1996-08-06 | Goetze Payen Gmbh | Cylinder head gasket with folded u-shaped stopper |
-
0
- DE DENDAT194810D patent/DE194810C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5542683A (en) * | 1994-07-27 | 1996-08-06 | Goetze Payen Gmbh | Cylinder head gasket with folded u-shaped stopper |
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