JPS6258324B2 - - Google Patents
Info
- Publication number
- JPS6258324B2 JPS6258324B2 JP11323980A JP11323980A JPS6258324B2 JP S6258324 B2 JPS6258324 B2 JP S6258324B2 JP 11323980 A JP11323980 A JP 11323980A JP 11323980 A JP11323980 A JP 11323980A JP S6258324 B2 JPS6258324 B2 JP S6258324B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydroxy
- sodium
- alkylbenzoic
- alkyl
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000606 toothpaste Substances 0.000 description 11
- 229940034610 toothpaste Drugs 0.000 description 11
- 241000194017 Streptococcus Species 0.000 description 9
- 241000894006 Bacteria Species 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 208000002064 Dental Plaque Diseases 0.000 description 7
- 208000002925 dental caries Diseases 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 6
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 6
- 239000001768 carboxy methyl cellulose Substances 0.000 description 6
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 6
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 6
- 229960003260 chlorhexidine Drugs 0.000 description 6
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 description 6
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 6
- 229940081974 saccharin Drugs 0.000 description 6
- 235000019204 saccharin Nutrition 0.000 description 6
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 6
- 229960004793 sucrose Drugs 0.000 description 6
- XGRSAFKZAGGXJV-UHFFFAOYSA-N 3-azaniumyl-3-cyclohexylpropanoate Chemical compound OC(=O)CC(N)C1CCCCC1 XGRSAFKZAGGXJV-UHFFFAOYSA-N 0.000 description 5
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 208000028169 periodontal disease Diseases 0.000 description 5
- 230000007505 plaque formation Effects 0.000 description 5
- 229960004711 sodium monofluorophosphate Drugs 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 150000004676 glycans Chemical class 0.000 description 4
- 239000010903 husk Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000002324 mouth wash Substances 0.000 description 4
- 201000001245 periodontitis Diseases 0.000 description 4
- 229920001282 polysaccharide Polymers 0.000 description 4
- 239000005017 polysaccharide Substances 0.000 description 4
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 4
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 229920002307 Dextran Polymers 0.000 description 3
- 108010001682 Dextranase Proteins 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 229940112822 chewing gum Drugs 0.000 description 2
- 235000015218 chewing gum Nutrition 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 210000003298 dental enamel Anatomy 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 108010000165 exo-1,3-alpha-glucanase Proteins 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229940051866 mouthwash Drugs 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011775 sodium fluoride Substances 0.000 description 2
- 235000013024 sodium fluoride Nutrition 0.000 description 2
- 229960000414 sodium fluoride Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000003053 toxin Substances 0.000 description 2
- 231100000765 toxin Toxicity 0.000 description 2
- 108700012359 toxins Proteins 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 244000205574 Acorus calamus Species 0.000 description 1
- 235000006480 Acorus calamus Nutrition 0.000 description 1
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 description 1
- 235000001271 Anacardium Nutrition 0.000 description 1
- 241000693997 Anacardium Species 0.000 description 1
- 244000226021 Anacardium occidentale Species 0.000 description 1
- 235000001274 Anacardium occidentale Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 101000925662 Enterobacteria phage PRD1 Endolysin Proteins 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- 102000000340 Glucosyltransferases Human genes 0.000 description 1
- 108010055629 Glucosyltransferases Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241001316290 Gypsophila Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 108010014251 Muramidase Proteins 0.000 description 1
- 102000016943 Muramidase Human genes 0.000 description 1
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 208000025157 Oral disease Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 235000001537 Ribes X gardonianum Nutrition 0.000 description 1
- 235000001535 Ribes X utile Nutrition 0.000 description 1
- 235000016919 Ribes petraeum Nutrition 0.000 description 1
- 244000281247 Ribes rubrum Species 0.000 description 1
- 235000002355 Ribes spicatum Nutrition 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- KGUHOFWIXKIURA-VQXBOQCVSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl dodecanoate Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](COC(=O)CCCCCCCCCCC)O[C@@H]1O[C@@]1(CO)[C@@H](O)[C@H](O)[C@@H](CO)O1 KGUHOFWIXKIURA-VQXBOQCVSA-N 0.000 description 1
- SZYSLWCAWVWFLT-UTGHZIEOSA-N [(2s,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)-2-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-yl]methyl octadecanoate Chemical compound O([C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)[C@]1(COC(=O)CCCCCCCCCCCCCCCCC)O[C@H](CO)[C@@H](O)[C@@H]1O SZYSLWCAWVWFLT-UTGHZIEOSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- LFVVNPBBFUSSHL-UHFFFAOYSA-N alexidine Chemical compound CCCCC(CC)CNC(=N)NC(=N)NCCCCCCNC(=N)NC(=N)NCC(CC)CCCC LFVVNPBBFUSSHL-UHFFFAOYSA-N 0.000 description 1
- 229950010221 alexidine Drugs 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960000458 allantoin Drugs 0.000 description 1
- TUFYVOCKVJOUIR-UHFFFAOYSA-N alpha-Thujaplicin Natural products CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 description 1
- 229940024548 aluminum oxide Drugs 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- KAOMOVYHGLSFHQ-UTOQUPLUSA-N anacardic acid Chemical compound CCC\C=C/C\C=C/CCCCCCCC1=CC=CC(O)=C1C(O)=O KAOMOVYHGLSFHQ-UTOQUPLUSA-N 0.000 description 1
- 235000014398 anacardic acid Nutrition 0.000 description 1
- ADFWQBGTDJIESE-UHFFFAOYSA-N anacardic acid 15:0 Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1C(O)=O ADFWQBGTDJIESE-UHFFFAOYSA-N 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 230000001147 anti-toxic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
- 239000007621 bhi medium Substances 0.000 description 1
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- 229960003563 calcium carbonate Drugs 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 229960004830 cetylpyridinium Drugs 0.000 description 1
- NEUSVAOJNUQRTM-UHFFFAOYSA-N cetylpyridinium Chemical compound CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 NEUSVAOJNUQRTM-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910002026 crystalline silica Inorganic materials 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
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- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229940095079 dicalcium phosphate anhydrous Drugs 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
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- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
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- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004325 lysozyme Substances 0.000 description 1
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- 210000000214 mouth Anatomy 0.000 description 1
- 208000030194 mouth disease Diseases 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 239000008363 phosphate buffer Substances 0.000 description 1
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- 150000003013 phosphoric acid derivatives Chemical group 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
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- 150000003856 quaternary ammonium compounds Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Chemical group 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 229940075560 sodium lauryl sulfoacetate Drugs 0.000 description 1
- AQMNWCRSESPIJM-UHFFFAOYSA-M sodium metaphosphate Chemical compound [Na+].[O-]P(=O)=O AQMNWCRSESPIJM-UHFFFAOYSA-M 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- UAJTZZNRJCKXJN-UHFFFAOYSA-M sodium;2-dodecoxy-2-oxoethanesulfonate Chemical compound [Na+].CCCCCCCCCCCCOC(=O)CS([O-])(=O)=O UAJTZZNRJCKXJN-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960002799 stannous fluoride Drugs 0.000 description 1
- ANOBYBYXJXCGBS-UHFFFAOYSA-L stannous fluoride Chemical compound F[Sn]F ANOBYBYXJXCGBS-UHFFFAOYSA-L 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- -1 sucrose fatty acid ester Chemical class 0.000 description 1
- 229940032085 sucrose monolaurate Drugs 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GYDJEQRTZSCIOI-LJGSYFOKSA-N tranexamic acid Chemical compound NC[C@H]1CC[C@H](C(O)=O)CC1 GYDJEQRTZSCIOI-LJGSYFOKSA-N 0.000 description 1
- 229960000401 tranexamic acid Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 229930007845 β-thujaplicin Natural products 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- 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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/368—Carboxylic acids; Salts or anhydrides thereof with carboxyl groups directly bound to carbon atoms of aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Cosmetics (AREA)
Description
本発明は2−ヒドロキシ−6−アルキルベンゾ
イツクアシドを配合することにより、歯垢の形成
及び酸産生を抑制してう蝕及び歯周疾患を予防す
る口腔用組成物に関する。
歯の表面に付着する歯垢は、約70%の細菌、細
菌により形成された約20%の多糖、及び約10%の
食物残渣よりなり、固く歯面にこびりついてい
る。そして、その内部に貯えられた酸がエナメル
質を脱灰し、菌及び産生された毒素が歯肉炎、歯
周炎、更には歯槽膿漏をもたらすといわれてお
り、口腔の二大疾患であるう蝕、歯槽膿漏の原因
として注目されている。
この歯垢はストレプトコツカス・ミユータンス
を中心とする口腔内細菌によつて口腔内に存在す
るシヨ糖を利用して形成される。即ち、ストレプ
トコツカス・ミユータンスはGTF(グルコシル
トランスフエラーゼ、デキストラン合成酵素)を
産生し、これによりシヨ糖からデキストラン、ム
タン等の粘着性多糖を合成する。そして、この合
成された多糖はストレプトコツカス・ミユータン
スをはじめ、他の菌(病原菌)を巻き込み、一定
の菌叢を有する歯垢を形成する。また、ストレプ
トコツカス・ミユータンス等の菌は種々の糖を利
用して酸を産生し、この酸は多糖及び菌の壁の中
に滞留することにより、エナメル表面を脱灰して
いく。更に、菌の死骸や産生された種々の物質、
毒素は歯肉に対して悪影響を及ぼし、歯槽膿漏の
原因として作用する。
従つて、歯垢の形成を抑制、阻止し、また酸産
生を抑制することは、う蝕、歯周疾患を予防する
という点から非常に有効なことである。
本発明者らは、このような点を考慮し、う蝕、
歯周疾患の予防に好適な口腔用組成物につき鋭意
研究を行なつた結果、2−ヒドロキシ−6−アル
キルベンゾイツクアシドを有効成分として配合す
ることにより、上記目的が達成されることを知見
した。即ち、2−ヒドロキシ−6−アルキルベン
ゾイツクアシド(アナカルド酸)は従来より駆虫
作用、酵素阻害作用、抗毒素作用、解熱作用、殺
菌作用があることが知られているが、本発明者ら
が種々検討を行なつた結果、2−ヒドロキシ−6
−アルキルベンゾイツクアシドは比較的低濃度に
おいてもストレプトコツカス・ミユータンスによ
る歯垢の形成を抑制し、その結果酸産生を抑制
し、従つて2−ヒドロキシ−6−アルキルベンゾ
イツクアシドが口腔用組成物の有効成分としてう
蝕、歯周疾患の予防に有効であることを知見し、
本発明をなすに至つたものである。
以下、本発明につき詳しく説明する。
本発明に係る口腔用組成物は、練歯磨、粉歯
磨、水歯磨などの歯磨類、マウスウオツシユ、ト
ローチ、パスタ、塗布剤、うがい用錠剤、歯肉マ
ツサージクリーム、チユーインガム等として使用
されるもので、有効成分として2−ヒドロキシ−
6−アルキルベンゾイツクアシドを含有してなる
ものである。
この場合、2−ヒドロキシ−6−アルキルベン
ゾイツクアシドとしては、アルキル基の炭素数が
13〜17で、アルキル基中に二重結合が0〜3個存
在しているものが好適に使用し得、これら2−ヒ
ドロキシ−6−アルキルベンゾイツクアシドはそ
の1種を単独で使用しても、2種以上の混合物と
して配合してもよい。なお、アルキル基は直鎖で
も分枝鎖があつてもよい。2−ヒドロキシ−6−
アルキルベンゾイツクアシドは、アルキル基の炭
素数13〜17、アルキル基の二重結合の数0〜3の
ものの混合物としてイチヨウ(Ginkgo biloba L.
)の果実及び葉、カシユウ(Anacardium
occidentale L.)の種子殻、オリエンタルカシユ
ウ(Semicarpus anacardium L.)の種子等に含
まれており、従つてこれらの植物より抽出するこ
とによつて得られる2−ヒドロキシ−6−アルキ
ルベンゾイツクアシドの混合物を配合することが
できる。
2−ヒドロキシ−6−アルキルベンゾイツクア
シドの口腔用組成物中への配合量は、全体の
0.0001〜1%(重量%、以下同じ)、特に0.001〜
0.1%とすることが好ましい。
本発明の他の成分としては、口腔用組成物の種
類に応じた適宜な成分が用いられる。例えば練歯
磨の場合であれば、第2リン酸カルシウム、炭酸
カルシウム、不溶性メタリン酸ナトリウム、非晶
質シリカ、結晶質シリカ、酸化アルミニウム等の
研磨剤、カルボキシメチルセルロース、ヒドロキ
シエチルセルロース、アルギン酸塩、カラゲナ
ン、アラビアガム、ポリビニルアルコール等の粘
結剤、ポリエチレングリコール、ソルビトール、
グリセリン、プロピレングリコール等の粘稠剤、
ラウリン硫酸ナトリウム、ドデシルベンゼンスル
ホン酸ナトリウム、水素添加ココナツツ脂肪酸モ
ノグリセリドモノ硫酸ナトリウム、ラウリルスル
ホ酢酸ナトリウム、N−ラウロイルザルコシン酸
ナトリウム、N−アシルグルタミン酸塩、シヨ糖
脂肪酸エステル等の発泡剤、それに甘味剤、香
料、防腐剤などの成分を水と混和し、常法に従つ
て製造する。また、マウスウオツツユ等の口腔洗
浄剤その他においても、製品の性状に応じた成分
が適宜配合される。
なお、本発明においては、2−ヒドロキシ−6
−アルキルベンゾイツクアシドに加えて塩化リゾ
チーム、デキストラナーゼ、溶菌酵素、ムタナー
ゼ、クロルヘキシジン、ソルビン酸、アレキシジ
ン、ヒノキチオール、セチルピリジニウム、アル
キルグリシン、アルキルジアミノエチルグリシン
塩、トラネキサム酸、ε−アミノカプロン酸、ア
ラントイン、アズレン、ビタミンE、モノフルオ
ロリン酸ナトリウム、フツ化ナトリウム、フツ化
第1錫、水溶性第一もしくは第二リン酸塩、第四
級アンモニウム化合物、塩化ナトリウムなどの有
効成分を配合することもできる。
本発明に係る口腔用組成物は、2−ヒドロキシ
−6−アルキルベンゾイツクアシドを配合したこ
とにより、ストレプトコツカス・ミユータンスに
よる歯垢の形成を効果的に抑制すると共に、酸産
生を抑制し、従つてう蝕の発生、歯周疾患を良好
に防止する。
また、本発明の口腔用組成物は、有効成分とし
て2−ヒドロキシ−6−アルキルベンゾイツクア
シドを配合する場合、比較的低濃度の配合でも歯
垢形成阻止効果、酸産生阻止効果が高く、従つて
配合量を少なくすることができるので、使用上の
安全性も高いものである。
次に実験例を示し、本発明の効果を具体的に説
明する。
〔実験例〕
イチヨウ葉の乾燥粉末100gを石油エーテルで
3回室温にて抽出し、その抽出液を濃縮後、画分
をエチルエーテルに溶解させた。これに1%炭酸
ナトリウム溶液を加えて充分振盪する操作を3回
繰返し、1%炭酸ナトリウム溶液に移行する酸性
物質に1N塩酸溶液を加えてPHを下げ(PH2にす
る)、再びエチルエーテルに溶解させ、濃縮し
て、2.1gの褐色のペーストを得た。これを更に
石油エーテル:酢酸=100:1(容量比)の混合
液50mlに溶かし、シリカゲル(ワコーゲルC−
200)を充填したカラム(φ2cm×20cm)に通
し、上と同じ混合液で溶出させて、淡黄色油状の
2−ヒドロキシ−6−アルキルベンゾイツクアシ
ド1.7gを得た。
また、炒つたカシユウの種子殻粉末100gを上
記と同様に操作して2−ヒドロキシ−6−アルキ
ルベンゾイツクアシド5.0gを得た。
なお、イチヨウ葉からの2−ヒドロキシ−6−
アルキルベンゾイツクアシド、カシユウ種子殻か
らの2−ヒドロキシ−6−アルキルベンゾイツク
アシドのアルキル基の炭素数、二重結合の数及び
位置は第1表の通りである。
The present invention relates to an oral composition containing 2-hydroxy-6-alkylbenzoic acid to inhibit dental plaque formation and acid production to prevent dental caries and periodontal disease. Dental plaque that adheres to the tooth surface is made up of about 70% bacteria, about 20% polysaccharide formed by bacteria, and about 10% food residue, and is firmly stuck to the tooth surface. The acid stored inside demineralizes the enamel, and the bacteria and toxins produced are said to cause gingivitis, periodontitis, and even pyorrhea, two major oral diseases. It is attracting attention as a cause of caries and alveolar pyorrhea. This dental plaque is formed by oral bacteria, mainly Streptococcus miutans, using sucrose present in the oral cavity. That is, Streptococcus miutans produces GTF (glucosyltransferase, dextran synthase), which synthesizes sticky polysaccharides such as dextran and mutan from sucrose. This synthesized polysaccharide then attracts Streptococcus miutans and other bacteria (pathogens), forming dental plaque with a certain bacterial flora. Furthermore, bacteria such as Streptococcus miutans produce acids using various sugars, and this acid demineralizes the enamel surface by staying in the walls of polysaccharides and bacteria. Furthermore, dead bacteria and various substances produced,
Toxins have a negative effect on the gums and act as a cause of pyorrhea. Therefore, suppressing or inhibiting the formation of dental plaque and inhibiting acid production are very effective in preventing dental caries and periodontal diseases. Taking these points into consideration, the present inventors have investigated caries, caries,
As a result of intensive research into oral compositions suitable for the prevention of periodontal diseases, it was discovered that the above objectives could be achieved by incorporating 2-hydroxy-6-alkylbenzoitic acid as an active ingredient. . That is, 2-hydroxy-6-alkylbenzoic acid (anacardic acid) has been known to have anthelmintic, enzyme-inhibiting, antitoxin, antipyretic, and bactericidal effects; As a result of investigation, 2-hydroxy-6
- Even at relatively low concentrations, alkyl benzoitukacids inhibit plaque formation by Streptococcus miutans and, as a result, acid production; We discovered that it is effective in preventing caries and periodontal disease as an active ingredient in products.
This has led to the present invention. The present invention will be explained in detail below. The oral composition according to the present invention can be used as dentifrices such as toothpaste, powdered toothpaste, water toothpaste, mouthwash, troche, pasta, liniment, gargling tablet, gingival massage cream, chewing gum, etc. , 2-hydroxy- as an active ingredient
It contains 6-alkylbenzoic acid. In this case, as the 2-hydroxy-6-alkylbenzoic acid, the number of carbon atoms in the alkyl group is
13 to 17 in which 0 to 3 double bonds are present in the alkyl group can be suitably used, and these 2-hydroxy-6-alkyl benzoitic acids can be used singly. They may also be blended as a mixture of two or more. Note that the alkyl group may be a straight chain or a branched chain. 2-hydroxy-6-
Alkylbenzoitukacid is a mixture of alkyl groups with 13 to 17 carbon atoms and alkyl groups with 0 to 3 double bonds, such as Ginkgo biloba L.
) fruits and leaves of Anacardium
occidentale L.), seeds of Oriental oak (Semicarpus anacardium L.), etc., and therefore, 2-hydroxy-6-alkylbenzoitic acid can be obtained by extracting from these plants. A mixture of these can be blended. The amount of 2-hydroxy-6-alkylbenzoitic acid added to the oral composition is
0.0001~1% (weight%, same below), especially 0.001~
It is preferably 0.1%. As other components of the present invention, appropriate components are used depending on the type of oral composition. For example, in the case of toothpaste, dibasic calcium phosphate, calcium carbonate, insoluble sodium metaphosphate, amorphous silica, crystalline silica, abrasives such as aluminum oxide, carboxymethyl cellulose, hydroxyethyl cellulose, alginate, carrageenan, gum arabic, etc. , binders such as polyvinyl alcohol, polyethylene glycol, sorbitol,
Thickening agents such as glycerin and propylene glycol,
Foaming agents such as sodium lauric sulfate, sodium dodecylbenzenesulfonate, sodium hydrogenated coconut fatty acid monoglyceride monosulfate, sodium lauryl sulfoacetate, sodium N-lauroylsarcosinate, N-acylglutamate, sucrose fatty acid ester, and sweeteners. , fragrance, preservatives and other ingredients are mixed with water and manufactured according to conventional methods. Also, in mouthwashes and other mouthwashes, ingredients are appropriately blended depending on the properties of the product. In addition, in the present invention, 2-hydroxy-6
-In addition to alkylbenzoitic acid, lysozyme chloride, dextranase, lytic enzyme, mutanase, chlorhexidine, sorbic acid, alexidine, hinokitiol, cetylpyridinium, alkylglycine, alkyldiaminoethylglycine salt, tranexamic acid, ε-aminocaproic acid, allantoin , azulene, vitamin E, sodium monofluorophosphate, sodium fluoride, stannous fluoride, water-soluble primary or secondary phosphates, quaternary ammonium compounds, sodium chloride, and other active ingredients may also be included. can. The oral composition according to the present invention contains 2-hydroxy-6-alkylbenzoic acid, thereby effectively suppressing the formation of dental plaque caused by Streptococcus miutans, and suppressing acid production. Therefore, the occurrence of dental caries and periodontal disease can be effectively prevented. In addition, when the oral composition of the present invention contains 2-hydroxy-6-alkylbenzoitic acid as an active ingredient, it has a high plaque formation inhibiting effect and acid production inhibiting effect even at a relatively low concentration. Since the amount to be blended can be reduced, the safety in use is also high. Next, experimental examples will be shown to specifically explain the effects of the present invention. [Experimental example] 100 g of dry powder of curvaceous leaves was extracted three times with petroleum ether at room temperature, the extract was concentrated, and the fractions were dissolved in ethyl ether. Add 1% sodium carbonate solution to this and shake thoroughly three times, add 1N hydrochloric acid solution to the acidic substance that will transfer to 1% sodium carbonate solution to lower the pH (to PH2), and dissolve in ethyl ether again. and concentrated to give 2.1 g of brown paste. This was further dissolved in 50 ml of a mixture of petroleum ether and acetic acid = 100:1 (volume ratio), and silica gel (Wako Gel C-
200) and eluted with the same mixture as above to obtain 1.7 g of 2-hydroxy-6-alkylbenzoic acid as a pale yellow oil. In addition, 100 g of roasted oak seed husk powder was treated in the same manner as above to obtain 5.0 g of 2-hydroxy-6-alkylbenzoic acid. In addition, 2-hydroxy-6-
The number of carbon atoms, number and position of double bonds in the alkyl group of the alkyl benzoitic acid, 2-hydroxy-6-alkyl benzoitic acid from oak seed husk are as shown in Table 1.
【表】
る。
次に、上記イチヨウ葉及びカシユウ種子殻由来
の2−ヒドロキシ−6−アルキルベンゾイツクア
シドを試験試料とし、下記培養付着法及び反応付
着法によりその歯垢形成抑制の効果を評価した。
培養付着法
1%のシヨ糖を含むBHI培地に上記試験試料を
所定量(第2表に示す量)添加し、これに前培養
しておいたストレプトコツカス・ミユータンス
6715株を接種し、N2:CO2:H2=80:10:10に
ガス置換されたアナエロボツクス内で37℃、16時
間培養した。培養後、0.01Mリン酸緩衝液(PH
7.0)で静かに2回洗浄し、次いで培養液と同量
の同緩衝液を加えて激しく撹拌し、フオトメータ
ーを用いて550nmで吸光度(濁度)を測定し、付
着歯垢量を求めた。
反応付着法
1%のシヨ糖、0.01%の殺菌剤(NaN3)及び熱
殺菌したストレプトコツカス・ミユータンス6715
株の菌体を含む0.05Mリン酸緩衝液(PH7.0)に
上記試験試料を所定量(第2表に示す量)添加
し、これにあらかじめ調製しておいたストレプト
コツカス・ミユータンス6715株の菌体外酵素を加
えて37℃、16時間反応させた。反応後、水で2回
洗浄し、次いで反応系と同量の水を加え、約20秒
間の超音波処理を行なつて歯垢を均一に懸濁させ
た後、フオトメーターを用いて550nmで吸光度
(濁度)を測定し、付着歯垢量を求めた。
結果を第2表に示す。なお、結果は試験試料を
添加しないコントロールの付着歯垢量を100%と
した場合の百分率で示した。[Table]
Next, the above-mentioned 2-hydroxy-6-alkyl benzoitic acid derived from the Gulbus leaves and Oak seed husks were used as test samples, and their effectiveness in inhibiting dental plaque formation was evaluated by the following culture attachment method and reaction attachment method. Culture adhesion method A predetermined amount of the above test sample (amount shown in Table 2) was added to BHI medium containing 1% sucrose, and Streptococcus miutans was precultured therein.
The 6715 strain was inoculated and cultured at 37°C for 16 hours in an Anaerobox gas exchanged with N 2 :CO 2 :H 2 =80:10:10. After culturing, add 0.01M phosphate buffer (PH
7.0), then added the same amount of the same buffer as the culture solution, stirred vigorously, and measured the absorbance (turbidity) at 550 nm using a photometer to determine the amount of attached plaque. . Reactive deposition method 1% sucrose, 0.01% fungicide (NaN 3 ) and heat sterilized Streptococcus miutans 6715
A predetermined amount (amount shown in Table 2) of the above test sample was added to a 0.05M phosphate buffer solution (PH7.0) containing the bacterial cells of the strain, and Streptococcus miutans 6715 strain prepared in advance was added thereto. Extracellular enzyme was added and the mixture was reacted at 37°C for 16 hours. After the reaction, wash twice with water, then add the same amount of water as the reaction system, perform ultrasonic treatment for about 20 seconds to uniformly suspend the plaque, and then use a photometer to disperse the plaque at 550 nm. The absorbance (turbidity) was measured to determine the amount of attached plaque. The results are shown in Table 2. The results are expressed as a percentage, with the amount of plaque attached to the control to which no test sample was added as 100%.
【表】
第2表の結果より、2−ヒドロキシ−6−アル
キルベンゾイツクアシドは、プラークの形成を阻
害する効果を有することが知見される。
なお、イチヨウ葉由来の2−ヒドロキシ−6−
アルキルベンゾイツクアシドの急性毒性を調べた
結果はLD50>1g/Kgマウス(経口投与)であ
つた。
以下、実施例を示す。なお、%はいずれも重量
%であり、また2−ヒドロキシ−6−アルキルベ
ンゾイツクアシド(イチヨウ)及び2−ヒドロキ
シ−6−アルキルベンゾイツクアシド(カシユ
ウ)はそれぞれ実験例と同様にして製造したイチ
ヨウ葉由来の2−ヒドロキシ−6−アルキルベン
ゾイツクアシド、カシユウ種子殻由来の2−ヒド
ロキシ−6−アルキルベンゾイツクアシドを示
す。
〔実施例1〕 練歯磨
第2リン酸カルシウム・2水和物 50.0%
グリセリン 20.0
カルボキシメチルセルロース 1.0
ソジウムラウリルサルフエート 1.0
香 料 1.0
2−ヒドロキシ−6−アルキルベンゾ 0.1
イツクアシド(イチヨウ)
サツカリン 0.1
フツ化ナトリウム 0.1水 残
100.0%
〔実施例2〕 練歯磨
第2リン酸カルシウム×2水和物 50.0%
ソルビツト 10.0
グリセリン 10.0
カルボキシメチルセルロース 1.0
ソジウムラウリルサルフエート 2.0
香 料 1.0
2−ヒドロキシ−6−アルキルベンゾイツク 0.1
アシド(カシユウ)
モノフルオロリン酸ナトリウム 0.3
エタノール 2.0
サツカリン 0.1
ムタナーゼ 0.1水 残
100.0%
〔実施例3〕 練歯磨
炭酸カルシウム 50.0%
グリセリン 20.0
カラゲナン 0.5
カルボキシメチルセルロース 1.0
ラウリルジエタノールアマイド 1.0%
シヨ糖モノラウレート 2.0
2−ヒドロキシ−6−アルキルベンゾイツク 0.1
アシド(イチヨウ)
香 料 1.0
サツカリン 0.1
クロルヘキシジン 0.005
デキストラナーゼ 0.01水 残
100.0%
〔実施例4〕 練歯磨
第2リン酸カルシウム・2水和物 50.0%
グリセリン 20.0
カルボキシメチルセルロース 2.0
ソジウムラウリルサルフエート 2.0
香 料 1.0
2−ヒドロキシ−6−アルキルベンゾイツク0.05
アシド(カシユウ)
クロルヘキシジン 0.01
サツカリン 0.1水 残
100.0%
〔実施例5〕 練歯磨
無水ケイ酸 30.0%
グリセリン 30.0
ソルビツト 20.0
カルボキシメチルセルロース 1.0
ソジウムラウリルサルフエート 2.0
香 料 1.0
サツカリン 0.1
2−ヒドロキシ−6−アルキルベンゾイツク 0.1
アシド(カシユウ)
エタノール 2.0水 残
100.0%
〔実施例6〕 粉歯磨
第2リン酸カルシウム・2水和物 50.0%
炭酸カルシウム 30.0
グリセリン 10.0
α−オレフインスルフオネート 1.0
香 料 1.0%
サツカリン 0.1
2−ヒドロキシ−6−アルキルベンゾイツク0.05
アシド(イチヨウ)
2−ヒドロキシ−6−アルキルベンゾイツク0.05
アシド(カシユウ)
モノフルオロリン酸ナトリウム 0.1
デキストラン 0.5水 残
100.0%
〔実施例7〕 液状歯磨
ポリアクリル酸ナトリウム 50.0%
グリセリン 30.0
サツカリン 0.1
香 料 0.9
クロルヘキシジン 0.01
2−ヒドロキシ−6−アルキルベンゾイツク 0.1
アシド(イチヨウ)
エタノール 3.0
リノール酸 0.05水 残 %
100.0%
〔実施例8〕 マウスウオツシユ
エタノール 20.0%
サツカリン 0.05
香 料 1.0
モノフルオロリン酸ナトリウム 0.1
クロルヘキシジン 0.01
ラウリルジエタノールアマイド 0.3
2−ヒドロキシ−6−アルキルベンゾイツク 0.1
アシド(カシユウ)水 残
100.0%
〔実施例9〕 チユーインガム
ガムベース 44.0%
炭酸カルシウム 2.0
水アメ 15.0
粉 糖 30.0
シヨ糖パルミテート 1.0
フクルトース 4.0
マルトース 3.0%
2−ヒドロキシ−6−アルキルベンゾイツク 0.1
アシド(カシユウ)香 料 0.9
100.0%
〔実施例10〕 うがい用錠剤
炭酸水素ナトリウム 54.0%
第2リン酸ナトリウム 10.0
ポリエチレングリコール 3.0
香 料 2.0
オレイン酸 0.1
モノフルオロリン酸ナトリウム 0.1
クロルヘキシジン 0.1
2−ヒドロキシ−6−アルキルベンゾイツク 0.1
アシド(イチヨウ)
クエン酸 17硫酸ナトリウム(無水) 13.6
100.0%
〔実施例11〕 歯肉マツサージクリーム
白色ワセリン 8.0%
プロピレングリコール 4.0%
デキストラナーゼ 1.0
ステアリルアルコール 8.0
ポリエチレングリコール4000 25.0
〃 400 37.0
シヨ糖ステアリン酸エステル 0.5
2−ヒドロキシ−6−アルキルベンゾイツク 0.1
アシド(イチヨウ)水 残
100.0%[Table] From the results in Table 2, it is found that 2-hydroxy-6-alkylbenzoic acid has the effect of inhibiting plaque formation. In addition, 2-hydroxy-6- derived from Gypsophila leaf
The results of examining the acute toxicity of alkyl benzoitic acid were LD 50 >1 g/Kg mouse (oral administration). Examples are shown below. In addition, all percentages are weight percent, and 2-hydroxy-6-alkylbenzoic acid (Japanese currant) and 2-hydroxy-6-alkylbenzoic acid (Japanese sardine) were obtained using the same method as in the experimental example. 2-Hydroxy-6-alkylbenzoic acid derived from leaves and 2-hydroxy-6-alkyl benzoic acid derived from oak seed husk are shown. [Example 1] Toothpaste dicalcium phosphate dihydrate 50.0% Glycerin 20.0 Carboxymethyl cellulose 1.0 Sodium lauryl sulfate 1.0 Fragrance 1.0 2-Hydroxy-6-alkylbenzo 0.1 Itsuquaside (Sweetroot) Satucalin 0.1 Sodium fluoride 0.1 Water remaining 100.0% [Example 2] Toothpaste dicalcium phosphate x dihydrate 50.0% Sorbit 10.0 Glycerin 10.0 Carboxymethylcellulose 1.0 Sodium lauryl sulfate 2.0 Fragrance 1.0 2-Hydroxy-6-alkylbenzoic 0.1 Acid ) Sodium monofluorophosphate 0.3 Ethanol 2.0 Saccharin 0.1 Mutanase 0.1 Water Remaining 100.0% [Example 3] Toothpaste calcium carbonate 50.0% Glycerin 20.0 Carrageenan 0.5 Carboxymethyl cellulose 1.0 Lauryl diethanolamide 1.0% Sucrose monolaurate 2.0 2-Hydroxy- 6-Alkylbenzoic acid 0.1 Acid Flavoring 1.0 Saccharin 0.1 Chlorhexidine 0.005 Dextranase 0.01 Water Remaining 100.0% [Example 4] Toothpaste dicalcium phosphate dihydrate 50.0% Glycerin 20.0 Carboxymethyl cellulose 2.0 Sodium lauryl Sulfate 2.0 Flavor 1.0 2-Hydroxy-6-alkylbenzoic acid 0.05 Acid Chlorhexidine 0.01 Satucalin 0.1 Water Remaining 100.0% [Example 5] Toothpaste Silicic anhydride 30.0% Glycerin 30.0 Sorbit 20.0 Carboxymethyl cellulose 1.0 sodium lauryl Sulfate 2.0 Flavor 1.0 Saccharin 0.1 2-Hydroxy-6-alkylbenzoic acid 0.1 Acid Ethanol 2.0 Water Remaining 100.0% [Example 6] Toothpaste dicalcium phosphate dihydrate 50.0% Calcium carbonate 30.0 Glycerin 10.0 α-Olefin sulfonate 1.0 Flavor 1.0% Saccharin 0.1 2-Hydroxy-6-alkylbenzoic acid 0.05 Acid 2-hydroxy-6-alkyl benzoic acid 0.05 Acid Sodium monofluorophosphate 0.1 Dextran 0.5 Water Remaining 100.0% [Example 7] Liquid toothpaste Sodium polyacrylate 50.0% Glycerin 30.0 Saccharin 0.1 Fragrance 0.9 Chlorhexidine 0.01 2-Hydroxy-6-alkylbenzoic acid 0.1 Acid Ethanol 3.0 Linoleic acid 0.05 Water Remaining % 100.0% [ Example 8] Mouthwash ethanol 20.0% Saccharin 0.05 Fragrance 1.0 Sodium monofluorophosphate 0.1 Chlorhexidine 0.01 Lauryl diethanolamide 0.3 2-Hydroxy-6-alkylbenzoic acid 0.1 Acid water Remaining 100.0% [Example 9] Chewing gum gum base 44.0% Calcium carbonate 2.0 Starch syrup 15.0 Powdered sugar 30.0 Cane sugar palmitate 1.0 Fucultose 4.0 Maltose 3.0% 2-Hydroxy-6-alkylbenzoic acid 0.1 Acid flavoring 0.9 100.0% [Example 10] For gargling Tablet Sodium bicarbonate 54.0% Sodium diphosphate 10.0 Polyethylene glycol 3.0 Flavor 2.0 Oleic acid 0.1 Sodium monofluorophosphate 0.1 Chlorhexidine 0.1 2-Hydroxy-6-alkyl benzoic acid 0.1 Acid (Galcanthus) Citric acid 17 Sodium sulfate (anhydrous ) ) 13.6 100.0% [Example 11] Gingival pine surge cream white petrolatum 8.0% Propylene glycol 4.0% Dextranase 1.0 Stearyl alcohol 8.0 Polyethylene glycol 4000 25.0 〃 400 37.0 Sucrose stearate 0.5 2-hydroxy-6-alkylbenzoic acid 0.1 Acid water remaining 100.0%
Claims (1)
アシドを含有することを特徴とする口腔用組成
物。 2 2−ヒドロキシ−6−アルキルベンゾイツク
アシドがアルキル基の炭素数13〜17、アルキル基
の二重結合の数0〜3個のものである特許請求の
範囲第1項記載の口腔用組成物。 3 2−ヒドロキシ−6−アルキルベンゾイツク
アシドの含有量が全体の0.0001〜1重量%である
特許請求の範囲第1項又は第2項記載の口腔用組
成物。[Scope of Claims] 1. An oral composition characterized by containing 2-hydroxy-6-alkylbenzoic acid. 2. The oral composition according to claim 1, wherein the 2-hydroxy-6-alkylbenzoic acid has an alkyl group having 13 to 17 carbon atoms and an alkyl group having 0 to 3 double bonds. . 3. The oral composition according to claim 1 or 2, wherein the content of 2-hydroxy-6-alkylbenzoitic acid is 0.0001 to 1% by weight of the total amount.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11323980A JPS5738709A (en) | 1980-08-18 | 1980-08-18 | Composition for oral purpose |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP11323980A JPS5738709A (en) | 1980-08-18 | 1980-08-18 | Composition for oral purpose |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5738709A JPS5738709A (en) | 1982-03-03 |
JPS6258324B2 true JPS6258324B2 (en) | 1987-12-05 |
Family
ID=14607087
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP11323980A Granted JPS5738709A (en) | 1980-08-18 | 1980-08-18 | Composition for oral purpose |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5738709A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0429922U (en) * | 1990-07-03 | 1992-03-10 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2613474B2 (en) * | 1989-03-25 | 1997-05-28 | サンスター株式会社 | Oral antibacterial composition |
JP2613301B2 (en) * | 1990-02-20 | 1997-05-28 | 御木本製薬株式会社 | Oral composition |
JP5294536B2 (en) * | 2005-03-31 | 2013-09-18 | 小林製薬株式会社 | Gingival epithelial cell spreading inhibitor |
-
1980
- 1980-08-18 JP JP11323980A patent/JPS5738709A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0429922U (en) * | 1990-07-03 | 1992-03-10 |
Also Published As
Publication number | Publication date |
---|---|
JPS5738709A (en) | 1982-03-03 |
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