JPS62181202A - 抗菌剤 - Google Patents
抗菌剤Info
- Publication number
- JPS62181202A JPS62181202A JP2229886A JP2229886A JPS62181202A JP S62181202 A JPS62181202 A JP S62181202A JP 2229886 A JP2229886 A JP 2229886A JP 2229886 A JP2229886 A JP 2229886A JP S62181202 A JPS62181202 A JP S62181202A
- Authority
- JP
- Japan
- Prior art keywords
- licochalcone
- microorganisms
- antimicrobial agent
- various products
- contamination
- 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.)
- Granted
Links
- 239000004599 antimicrobial Substances 0.000 title abstract 3
- 239000004480 active ingredient Substances 0.000 claims abstract description 7
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 235000005513 chalcones Nutrition 0.000 claims abstract description 4
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims abstract description 4
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- KAZSKMJFUPEHHW-UHFFFAOYSA-N (2E)-3-[5-(1,1-dimethyl-2-propenyl)-4-hydroxy-2-methoxyphenyl]-1-(4-hdyroxyphenyl)-2-propen-1-one Natural products COC1=CC(O)=C(C(C)(C)C=C)C=C1C=CC(=O)C1=CC=C(O)C=C1 KAZSKMJFUPEHHW-UHFFFAOYSA-N 0.000 abstract description 16
- IUCVKTHEUWACFB-UHFFFAOYSA-N Licochalcone A Natural products COC1=CC=C(C(C)(C)C=C)C=C1C=CC(=O)C1=CC=C(O)C=C1 IUCVKTHEUWACFB-UHFFFAOYSA-N 0.000 abstract description 16
- KAZSKMJFUPEHHW-DHZHZOJOSA-N Licochalcone A Chemical compound COC1=CC(O)=C(C(C)(C)C=C)C=C1\C=C\C(=O)C1=CC=C(O)C=C1 KAZSKMJFUPEHHW-DHZHZOJOSA-N 0.000 abstract description 16
- 244000005700 microbiome Species 0.000 abstract description 9
- 235000006200 Glycyrrhiza glabra Nutrition 0.000 abstract description 8
- 230000006866 deterioration Effects 0.000 abstract description 5
- 238000011109 contamination Methods 0.000 abstract description 4
- 239000002537 cosmetic Substances 0.000 abstract description 4
- 241000193830 Bacillus <bacterium> Species 0.000 abstract description 3
- 244000063299 Bacillus subtilis Species 0.000 abstract description 3
- 235000014469 Bacillus subtilis Nutrition 0.000 abstract description 3
- 241000193470 Clostridium sporogenes Species 0.000 abstract description 3
- 229930003935 flavonoid Natural products 0.000 abstract description 3
- 235000017173 flavonoids Nutrition 0.000 abstract description 3
- 150000002215 flavonoids Chemical class 0.000 abstract description 3
- 235000013305 food Nutrition 0.000 abstract description 3
- 241000589517 Pseudomonas aeruginosa Species 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 244000303040 Glycyrrhiza glabra Species 0.000 abstract 1
- 235000017443 Hedysarum boreale Nutrition 0.000 abstract 1
- 235000007858 Hedysarum occidentale Nutrition 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 230000000844 anti-bacterial effect Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 241000202807 Glycyrrhiza Species 0.000 description 7
- 235000001453 Glycyrrhiza echinata Nutrition 0.000 description 7
- 235000017382 Glycyrrhiza lepidota Nutrition 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 229940010454 licorice Drugs 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- DRDRYGIIYOPBBZ-XBXARRHUSA-N Licochalcone B Natural products COC1=C(O)C(O)=CC=C1\C=C\C(=O)C1=CC=C(O)C=C1 DRDRYGIIYOPBBZ-XBXARRHUSA-N 0.000 description 2
- WBDNTJSRHDSPSR-UHFFFAOYSA-N Licochalcone C Natural products C1=CC(O)=C(CC=C(C)C)C(OC)=C1C=CC(=O)C1=CC=C(O)C=C1 WBDNTJSRHDSPSR-UHFFFAOYSA-N 0.000 description 2
- 244000000231 Sesamum indicum Species 0.000 description 2
- 235000003434 Sesamum indicum Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229930187586 licochalcone Natural products 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000193764 Brevibacillus brevis Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004378 Glycyrrhizin Substances 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 238000005882 aldol condensation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- LPLVUJXQOOQHMX-UHFFFAOYSA-N glycyrrhetinic acid glycoside Natural products C1CC(C2C(C3(CCC4(C)CCC(C)(CC4C3=CC2=O)C(O)=O)C)(C)CC2)(C)C2C(C)(C)C1OC1OC(C(O)=O)C(O)C(O)C1OC1OC(C(O)=O)C(O)C(O)C1O LPLVUJXQOOQHMX-UHFFFAOYSA-N 0.000 description 1
- 229960004949 glycyrrhizic acid Drugs 0.000 description 1
- UYRUBYNTXSDKQT-UHFFFAOYSA-N glycyrrhizic acid Natural products CC1(C)C(CCC2(C)C1CCC3(C)C2C(=O)C=C4C5CC(C)(CCC5(C)CCC34C)C(=O)O)OC6OC(C(O)C(O)C6OC7OC(O)C(O)C(O)C7C(=O)O)C(=O)O UYRUBYNTXSDKQT-UHFFFAOYSA-N 0.000 description 1
- 235000019410 glycyrrhizin Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
- Cosmetics (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2229886A JPS62181202A (ja) | 1986-02-04 | 1986-02-04 | 抗菌剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2229886A JPS62181202A (ja) | 1986-02-04 | 1986-02-04 | 抗菌剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62181202A true JPS62181202A (ja) | 1987-08-08 |
| JPH0551561B2 JPH0551561B2 (enrdf_load_stackoverflow) | 1993-08-03 |
Family
ID=12078834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2229886A Granted JPS62181202A (ja) | 1986-02-04 | 1986-02-04 | 抗菌剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62181202A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5985935A (en) * | 1992-03-06 | 1999-11-16 | Statens Seruminstitut | Treatment and prophylaxis of diseases caused by parasites, or bacteria |
| DE10224387A1 (de) * | 2002-06-01 | 2003-12-11 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit einem aufbereiteten Extrakt aus Radix Glycyrrhizae inflatae |
| EP1541164A1 (de) * | 2003-12-02 | 2005-06-15 | Beiersdorf AG | Wirkstoffkombinationen aus Licochalcon A oder einem Extrakt aus Radix Glycyrrhizae inflatae, enthaltend Licochalcon A, Phenoxyethanol und gewünschtenfalls Glycerin |
| DE10356723A1 (de) * | 2003-12-02 | 2005-06-30 | Beiersdorf Ag | Desodorierende und/oder antitranspirierend wirkende kosmetische Zubereitungen mit einem Gehalt an Licochalcon A oder eines Licocalchon A enthaltenden Extraktes aus Radix Gly-cyrrhizae inflatae |
| DE102010012384A1 (de) * | 2010-03-22 | 2011-09-22 | Beiersdorf Ag | Hautfreundliche Wirkstoffkombination gegen Akne |
| CN110037997A (zh) * | 2019-06-20 | 2019-07-23 | 山西省农业科学院饲料兽药研究所 | 甘草查尔酮a在制备抗副猪嗜血杆菌药物中的应用 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4094332B2 (ja) * | 2002-04-23 | 2008-06-04 | 丸善製薬株式会社 | 水分散性又は水溶解性のバナバ葉抽出物組成物 |
-
1986
- 1986-02-04 JP JP2229886A patent/JPS62181202A/ja active Granted
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5985935A (en) * | 1992-03-06 | 1999-11-16 | Statens Seruminstitut | Treatment and prophylaxis of diseases caused by parasites, or bacteria |
| US6603046B1 (en) | 1992-03-06 | 2003-08-05 | Lica Pharmaceuticals A/S | Bis-aromatic a,β-unsaturated ketones |
| DE10224387A1 (de) * | 2002-06-01 | 2003-12-11 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit einem aufbereiteten Extrakt aus Radix Glycyrrhizae inflatae |
| US8470349B2 (en) | 2002-06-01 | 2013-06-25 | Beiersdorf Ag | Cosmetic or dermatological preparations containing licochalcone A or an extract of radix glycyrrhizae inflatae, containing licochalcone A |
| US9017707B2 (en) | 2002-06-01 | 2015-04-28 | Beiersdorf Ag | Cosmetic or dermatological preparations containing licochalcone A or an extract of radix glycyrrhizae inflatae, containing licochalcone A |
| EP1541164A1 (de) * | 2003-12-02 | 2005-06-15 | Beiersdorf AG | Wirkstoffkombinationen aus Licochalcon A oder einem Extrakt aus Radix Glycyrrhizae inflatae, enthaltend Licochalcon A, Phenoxyethanol und gewünschtenfalls Glycerin |
| DE10356723A1 (de) * | 2003-12-02 | 2005-06-30 | Beiersdorf Ag | Desodorierende und/oder antitranspirierend wirkende kosmetische Zubereitungen mit einem Gehalt an Licochalcon A oder eines Licocalchon A enthaltenden Extraktes aus Radix Gly-cyrrhizae inflatae |
| US8969418B2 (en) | 2003-12-02 | 2015-03-03 | Beiersdorf Ag | Active substance combination of licochalcone A and phenoxyethanol |
| US9693973B2 (en) | 2003-12-02 | 2017-07-04 | Beiersdorf Ag | Active substance combination of licochalcone A and phenoxyethanol |
| DE102010012384A1 (de) * | 2010-03-22 | 2011-09-22 | Beiersdorf Ag | Hautfreundliche Wirkstoffkombination gegen Akne |
| CN110037997A (zh) * | 2019-06-20 | 2019-07-23 | 山西省农业科学院饲料兽药研究所 | 甘草查尔酮a在制备抗副猪嗜血杆菌药物中的应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0551561B2 (enrdf_load_stackoverflow) | 1993-08-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |