CN115806478B - Metal salt of hinokitiol, and preparation method and application thereof - Google Patents
Metal salt of hinokitiol, and preparation method and application thereof Download PDFInfo
- Publication number
- CN115806478B CN115806478B CN202111156394.6A CN202111156394A CN115806478B CN 115806478 B CN115806478 B CN 115806478B CN 202111156394 A CN202111156394 A CN 202111156394A CN 115806478 B CN115806478 B CN 115806478B
- Authority
- CN
- China
- Prior art keywords
- hinokitiol
- metal salt
- salt
- sodium
- acid
- 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.)
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Links
- FUWUEFKEXZQKKA-UHFFFAOYSA-N beta-thujaplicin Chemical compound CC(C)C=1C=CC=C(O)C(=O)C=1 FUWUEFKEXZQKKA-UHFFFAOYSA-N 0.000 title claims abstract description 236
- TUFYVOCKVJOUIR-UHFFFAOYSA-N alpha-Thujaplicin Natural products CC(C)C=1C=CC=CC(=O)C=1O TUFYVOCKVJOUIR-UHFFFAOYSA-N 0.000 title claims abstract description 121
- 229930007845 β-thujaplicin Natural products 0.000 title claims abstract description 121
- 150000003839 salts Chemical class 0.000 title claims abstract description 62
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 57
- 239000002184 metal Substances 0.000 title claims abstract description 57
- 238000002360 preparation method Methods 0.000 title claims abstract description 27
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 69
- 239000000126 substance Substances 0.000 claims abstract description 12
- 229940079593 drug Drugs 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 5
- 235000013305 food Nutrition 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 59
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 27
- -1 organic acid salt Chemical class 0.000 claims description 17
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 229960003975 potassium Drugs 0.000 claims description 10
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 9
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 claims description 9
- 230000000845 anti-microbial effect Effects 0.000 claims description 9
- 235000002949 phytic acid Nutrition 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 8
- ZMJBYMUCKBYSCP-UHFFFAOYSA-N Hydroxycitric acid Chemical compound OC(=O)C(O)C(O)(C(O)=O)CC(O)=O ZMJBYMUCKBYSCP-UHFFFAOYSA-N 0.000 claims description 7
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 claims description 7
- FENRSEGZMITUEF-ATTCVCFYSA-E [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].OP(=O)([O-])O[C@@H]1[C@@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H]1OP(=O)([O-])[O-] Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].OP(=O)([O-])O[C@@H]1[C@@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H](OP(=O)([O-])[O-])[C@H](OP(=O)(O)[O-])[C@H]1OP(=O)([O-])[O-] FENRSEGZMITUEF-ATTCVCFYSA-E 0.000 claims description 7
- 229940089491 hydroxycitric acid Drugs 0.000 claims description 7
- 229940068041 phytic acid Drugs 0.000 claims description 7
- 239000000467 phytic acid Substances 0.000 claims description 7
- 239000001509 sodium citrate Substances 0.000 claims description 7
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 claims description 7
- 229940083982 sodium phytate Drugs 0.000 claims description 7
- 229960004106 citric acid Drugs 0.000 claims description 5
- 229960001790 sodium citrate Drugs 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 2
- 229960001484 edetic acid Drugs 0.000 claims description 2
- 239000001630 malic acid Substances 0.000 claims description 2
- 235000011090 malic acid Nutrition 0.000 claims description 2
- 229940099690 malic acid Drugs 0.000 claims description 2
- AVTYONGGKAJVTE-OLXYHTOASA-L potassium L-tartrate Chemical compound [K+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O AVTYONGGKAJVTE-OLXYHTOASA-L 0.000 claims description 2
- 239000001508 potassium citrate Substances 0.000 claims description 2
- 229960002635 potassium citrate Drugs 0.000 claims description 2
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 claims description 2
- 235000011082 potassium citrates Nutrition 0.000 claims description 2
- 229940111695 potassium tartrate Drugs 0.000 claims description 2
- 235000019265 sodium DL-malate Nutrition 0.000 claims description 2
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 claims description 2
- WPUMTJGUQUYPIV-UHFFFAOYSA-L sodium malate Chemical compound [Na+].[Na+].[O-]C(=O)C(O)CC([O-])=O WPUMTJGUQUYPIV-UHFFFAOYSA-L 0.000 claims description 2
- 239000001476 sodium potassium tartrate Substances 0.000 claims description 2
- 235000011006 sodium potassium tartrate Nutrition 0.000 claims description 2
- 239000001433 sodium tartrate Substances 0.000 claims description 2
- 229960002167 sodium tartrate Drugs 0.000 claims description 2
- 235000011004 sodium tartrates Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 229960001367 tartaric acid Drugs 0.000 claims description 2
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 18
- 230000002829 reductive effect Effects 0.000 abstract description 6
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 239000000843 powder Substances 0.000 description 24
- 229910003002 lithium salt Inorganic materials 0.000 description 22
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- 241000894006 Bacteria Species 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 159000000002 lithium salts Chemical class 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- 238000002156 mixing Methods 0.000 description 11
- 244000005700 microbiome Species 0.000 description 10
- 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 9
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052744 lithium Inorganic materials 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 230000002335 preservative effect Effects 0.000 description 8
- 230000002421 anti-septic effect Effects 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 239000003755 preservative agent Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- FRPWTKJJZHVSHD-UHFFFAOYSA-M sodium;7-oxo-3-propan-2-ylcyclohepta-1,3,5-trien-1-olate Chemical compound [Na+].CC(C)C1=CC=CC(=O)C([O-])=C1 FRPWTKJJZHVSHD-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 241000233866 Fungi Species 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 241000192125 Firmicutes Species 0.000 description 3
- 241000274177 Juniperus sabina Species 0.000 description 3
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 241000228245 Aspergillus niger Species 0.000 description 2
- 241000222122 Candida albicans Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000218691 Cupressaceae Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 241000282376 Panthera tigris Species 0.000 description 2
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 2
- GJJYQFPADNKBDY-UHFFFAOYSA-N Sabinol Natural products C=C1CCC2(C(C)C)C1(O)C2 GJJYQFPADNKBDY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-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 compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940095731 candida albicans Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 230000002147 killing effect Effects 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 239000006916 nutrient agar Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- MDFQXBNVOAKNAY-HWOCKDDLSA-N sabinol Chemical compound C([C@@H](O)C1=C)C2(C(C)C)C1C2 MDFQXBNVOAKNAY-HWOCKDDLSA-N 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- 241000193755 Bacillus cereus Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 240000005308 Juniperus chinensis Species 0.000 description 1
- 240000006024 Lactobacillus plantarum Species 0.000 description 1
- 235000013965 Lactobacillus plantarum Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QMHJFZUWNUAXQW-UHFFFAOYSA-J [Li+].[Cl-].[Mg+2].[Li+].[Cl-].[Cl-].[Cl-] Chemical compound [Li+].[Cl-].[Mg+2].[Li+].[Cl-].[Cl-].[Cl-] QMHJFZUWNUAXQW-UHFFFAOYSA-J 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- AIUDWMLXCFRVDR-UHFFFAOYSA-N dimethyl 2-(3-ethyl-3-methylpentyl)propanedioate Chemical compound CCC(C)(CC)CCC(C(=O)OC)C(=O)OC AIUDWMLXCFRVDR-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229940072205 lactobacillus plantarum Drugs 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910001386 lithium phosphate Inorganic materials 0.000 description 1
- INHCSSUBVCNVSK-UHFFFAOYSA-L lithium sulfate Inorganic materials [Li+].[Li+].[O-]S([O-])(=O)=O INHCSSUBVCNVSK-UHFFFAOYSA-L 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
- 229910052939 potassium sulfate Inorganic materials 0.000 description 1
- 235000011151 potassium sulphates Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003312 sabinol derivatives Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention belongs to the technical field of antibacterial substances, and discloses a metal salt of hinokitiol, and a preparation method and application thereof. The structural formula of the metal salt of hinokitiol is shown as formula (1): Wherein R + represents any one of Li +、Na+ or K +. The metal salt of the hinokitiol has good high-temperature resistance stability, good water solubility and good antibacterial performance, and the good antibacterial performance is beneficial to reducing the addition amount of the metal salt of the hinokitiol, so that the cost can be reduced. Can be widely applied to daily chemicals, foods or medicines.
Description
Technical Field
The invention belongs to the technical field of antibacterial substances, and particularly relates to a metal salt of hinokitiol, and a preparation method and application thereof.
Background
Hinokitiol is a well known bacteriostatic substance and can be used in cosmetics. But it has many limitations, so that it is not widely used in the daily chemical industry. Limitations of hinokitiol include: (1) The unit price is high, the common market hinokitiol is more than 5000 yuan/Kg, and the raw materials are quite expensive; (2) poor water solubility, which is unfavorable for application; (3) The stability of the product is poor, and most daily chemical products involve high temperature treatment.
Therefore, there is a need to provide a new sabinol derivative which has better high temperature stability than sabinol, further has better water solubility and further has better antibacterial performance.
Disclosure of Invention
The present invention aims to solve at least one of the technical problems in the prior art described above. Therefore, the metal salt of hinokitiol, as well as the preparation method and the application thereof are provided, and the metal salt of hinokitiol has good high-temperature stability, good water solubility and better antibacterial performance, and the better antibacterial performance is beneficial to reducing the addition amount of the metal salt of hinokitiol, so that the cost can be reduced.
The first aspect of the present invention provides a metal salt of hinokitiol.
Specifically, the structural formula of the metal salt of hinokitiol is shown as formula (1):
wherein R + represents any one of Li +、Na+ or K +. I.e. the metal salt of hinokitiol represents the lithium, sodium or potassium salt of hinokitiol.
Preferably, the R + represents Li +.
Preferably, the raw material component for preparing the metal salt of hinokitiol comprises hinokitiol and at least one of a lithium source, a sodium source or a potassium source.
Preferably, the lithium source is selected from at least one of lithium hydroxide, lithium carbonate, lithium phosphate, lithium magnesium lithium chloride silicate, or lithium sulfate.
Preferably, the sodium source is selected from at least one of sodium hydroxide, sodium carbonate, sodium bicarbonate or sodium sulfate.
Preferably, the potassium source is selected from at least one of potassium hydroxide, potassium carbonate, potassium phosphate or potassium sulfate.
Preferably, the raw material component for preparing the metal salt of hinokitiol further comprises a solvent; further preferably, the solvent is water.
Preferably, the mass ratio of the hinokitiol to at least one of the lithium source, the sodium source or the potassium source is 1: (0.05-4); further preferably, the mass ratio of the hinokitiol to at least one of the lithium source, the sodium source or the potassium source is 1: (0.1-3); more preferably, the mass ratio of the hinokitiol to at least one of the lithium source, the sodium source or the potassium source is 1: (0.5-3).
In a second aspect, the invention provides a method for preparing a metal salt of hinokitiol.
Specifically, the preparation method of the metal salt of hinokitiol comprises the following steps:
mixing at least one of a lithium source, a sodium source or a potassium source with a solvent, then adding hinokitiol, and heating for reaction to obtain the metal salt of hinokitiol.
Preferably, the mass-to-volume ratio of the solvent to at least one of the lithium source, the sodium source or the potassium source is (2-20) g: (40-250) mL; further preferably, the mass to volume ratio of the solvent to at least one of the lithium source, the sodium source or the potassium source is (5-15) g: (50-200) mL.
Preferably, the temperature of the heating reaction is 45-95 ℃; further preferably, the temperature of the heating reaction is 50-90 ℃; more preferably, the temperature of the heating reaction is 60-80 ℃.
Preferably, the heating reaction time is 10 minutes or more; further preferably, the heating reaction is carried out for a period of 20 to 120 minutes.
Preferably, after the heating reaction is finished, the product is filtered and freeze-dried to obtain a powdery product.
Preferably, after the heating reaction is finished, the metal salt of hinokitiol can be purified by washing with diethyl ether. The metal salt of hinokitiol is insoluble in diethyl ether.
Preferably, the metal salt of hinokitiol is prepared into an aqueous solution with the mass fraction of 0.1-50%; further preferably, the metal salt of hinokitiol is formulated as an aqueous solution of 0.1-40% by mass. The subsequent use of the metal salt of hinokitiol is facilitated.
In a third aspect, the invention provides the use of a metal salt of hinokitiol.
Specifically, an antibacterial composition comprises the metal salt, organic acid and/or organic acid salt of hinokitiol.
Preferably, the organic acid is at least one selected from citric acid, hydroxycitric acid, phytic acid, ethylenediamine tetraacetic acid, malic acid or tartaric acid.
Preferably, the organic acid salt is at least one selected from sodium citrate, potassium citrate, sodium phytate, potassium phytate, disodium edetate, tetrasodium edetate, disodium malate, sodium tartrate or potassium tartrate.
Preferably, the antibacterial composition comprises, by weight, 0.01-100 parts of the metal salt of hinokitiol, 0.05-50 parts of an organic acid and/or 0.05-80 parts of an organic acid salt.
Further preferably, the antibacterial composition comprises, by weight, 0.01-90 parts of the metal salt of hinokitiol, 0.05-45 parts of an organic acid and/or 0.05-75 parts of an organic acid salt.
The preparation method of the antibacterial composition comprises the following steps:
The components are mixed to produce the antimicrobial composition.
A fourth aspect of the present invention provides the use of a metal salt of hinokitiol as described above.
The metal salt of hinokitiol is used for preparing daily chemicals, foods or medicines.
The antibacterial composition is applied to the preparation of daily chemicals, foods or medicines.
Preferably, the daily chemical product comprises shampoo, bath lotion, cosmetics or washing powder.
Compared with the prior art, the invention has the following beneficial effects:
(1) The metal salt of hinokitiol has good high-temperature resistance stability, good water solubility and good antibacterial performance, and the good antibacterial performance is beneficial to reducing the addition amount of the metal salt of hinokitiol, so that the cost can be reduced.
(2) The antibacterial composition prepared from the metal salt of hinokitiol and organic acid and/or organic acid salt still has good antibacterial performance and high-temperature stability, so that the addition amount of the metal salt of hinokitiol can be further reduced, and the cost can be reduced.
(3) The metal salt of the hinokitiol has simple preparation process and high antibacterial effect, thereby having high cost performance and being widely applied to daily chemicals, foods or medicines.
Drawings
FIG. 1 is a 1 H-NMR (hydrogen nuclear magnetic resonance spectrum) chart of hinokitiol;
FIG. 2 is a 1 H-NMR chart of a lithium salt powder of hinokitiol prepared in example 1 of the present invention.
Detailed Description
In order to make the technical solutions of the present invention more apparent to those skilled in the art, the following examples will be presented. It should be noted that the following examples do not limit the scope of the invention.
The starting materials, reagents or apparatus used in the following examples are all available from conventional commercial sources or may be obtained by methods known in the art unless otherwise specified.
Example 1: preparation of metal salt of hinokitiol and antibacterial composition
A metal salt of hinokitiol has a structural formula shown in formula (2):
namely, formula (2) represents a lithium salt of hinokitiol.
The preparation method of the metal salt of hinokitiol comprises the following steps:
Mixing 10g of lithium hydroxide with 50mL of water, stirring for dissolution, adding 4g of hinokitiol, magnetically stirring at 100 r/min, heating at 60 ℃ for reaction for 30 min, cooling to separate out crystalline salt, filtering with a 0.2 mu m filter membrane, taking filter residues, and freeze-drying to obtain hinokitiol lithium salt powder. The mass content of the hinokitiol in the obtained hinokitiol lithium salt powder is 5.3%, and the mass content of the hinokitiol lithium salt is 94.7%.
To demonstrate that the above reaction gave a lithium salt of hinokitiol, the resulting product, i.e., a powder of a lithium salt of hinokitiol, was characterized with hinokitiol by 1 H-NMR, and the results are shown in FIGS. 1-2.
FIG. 1 is a 1 H-NMR chart of hinokitiol; FIG. 1 (abscissa "f1" in FIG. 1 shows chemical shift in ppm) shows signals of different protons related to carbon atoms in hinokitiol, which are assigned as 1.17 to 1.19ppm (H of CH 3 portion), 2.88 to 2.91ppm (H of CH portion), and 7.21 to 7.51ppm (H at carbon 3,5, 6, 7 positions in aromatic ring). At 4.70ppm is the solvent peak.
FIG. 2 is a 1 H-NMR chart of a lithium salt powder of hinokitiol prepared in example 1 of the present invention. FIG. 2 (abscissa "f1" in FIG. 2 shows chemical shift in ppm) shows signals of different protons in lithium salt of hinokitiol, which are allocated as follows: 1.12 to 1.13ppm (H of CH 3 portion), 2.72 to 2.78ppm (H of CH portion), 6.71 to 7.22ppm (H at carbon 3, 5, 6, 7 positions in aromatic ring). At 4.70ppm is the solvent peak.
The results shown in FIGS. 1 and 2 clearly show the forward movement of protons associated with aromatic rings (from 7.21-7.51ppm forward to 6.71-7.22 ppm). This shows that the aromatic ring of the lithium salt of hinokitiol in the product prepared in example 1 carries a negative charge and thus exists in anionic form, also confirming the formation of the lithium salt of hinokitiol.
An antibacterial composition comprises 99.5 parts of the above cypress alcohol lithium salt powder and 0.5 parts of citric acid.
The preparation method of the antibacterial composition comprises the following steps:
Mixing the lithium salt powder of hinokitiol and citric acid to obtain antibacterial composition.
Example 2: preparation of metal salt of hinokitiol and antibacterial composition
A metal salt of hinokitiol has a structural formula shown in formula (2):
namely, formula (2) represents a lithium salt of hinokitiol.
The preparation method of the metal salt of hinokitiol comprises the following steps:
Mixing 15g of lithium hydroxide with 50mL of water, stirring for dissolution, adding 10g of hinokitiol, magnetically stirring at 80 r/min, heating at 70 ℃ for reaction for 20 min, cooling to separate out crystalline salt, filtering with a 0.2 mu m filter membrane, taking filter residues, and freeze-drying to obtain hinokitiol lithium salt powder. The mass content of the hinokitiol in the obtained hinokitiol lithium salt powder is 8.5%, and the mass content of the hinokitiol lithium salt is 91.5%.
An antibacterial composition comprises 40 parts of the cypress alcohol lithium salt powder, 40 parts of citric acid and 20 parts of disodium edetate.
The preparation method of the antibacterial composition comprises the following steps:
Mixing Sabina alcohol lithium salt powder, citric acid, and disodium edetate to obtain antibacterial composition.
Example 3: preparation of metal salt of hinokitiol and antibacterial composition
A metal salt of hinokitiol has a structural formula shown in formula (3):
Namely, formula (3) represents the sodium salt of hinokitiol.
The preparation method of the metal salt of hinokitiol comprises the following steps:
Mixing 5g of sodium hydroxide and 200mL of water, stirring for dissolution, then adding 10g of hinokitiol, magnetically stirring at 120 r/min, heating at 80 ℃ for reaction for 40 min, cooling to separate out crystalline salt, filtering with a 0.2 mu m filter membrane, taking filter residues, and freeze-drying to obtain sodium salt powder of hinokitiol. The mass content of the hinokitiol in the obtained hinokitiol sodium salt powder is 5.9%, and the mass content of the hinokitiol sodium salt is 94.1%.
An antibacterial composition comprises 5 parts of the sodium salt powder of hinokitiol, 8 parts of hydroxycitric acid and 7 parts of sodium citrate.
The preparation method of the antibacterial composition comprises the following steps:
Mixing hinokitiol sodium salt powder, hydroxycitric acid and sodium citrate to obtain antibacterial composition.
Example 4: preparation of metal salt of hinokitiol and antibacterial composition
Preparation of metal salt of hinokitiol and antibacterial composition
A metal salt of hinokitiol has a structural formula shown in formula (3):
Namely, formula (3) represents the sodium salt of hinokitiol.
The preparation method of the metal salt of hinokitiol comprises the following steps:
10g of sodium hydroxide and 50mL of water are mixed and stirred for dissolution, then 5g of hinokitiol is added, the mixture is magnetically stirred at 100 revolutions per minute and heated at 85 ℃ for reaction for 35 minutes, then the mixture is cooled to separate out crystalline salt, the crystalline salt is filtered by a 0.2 mu m filter membrane, filter residues are taken out, and the filter residues are freeze-dried into powder, so as to obtain sodium salt powder of hinokitiol. The mass content of the hinokitiol in the obtained hinokitiol sodium salt powder is 5.5%, and the mass content of the hinokitiol sodium salt is 94.5%.
An antibacterial composition comprises 16 parts of the sodium salt powder of hinokitiol, 14 parts of phytic acid, 35 parts of sodium phytate and 35 parts of disodium edetate.
The preparation method of the antibacterial composition comprises the following steps:
Mixing hinokitiol sodium salt powder, phytic acid, sodium phytate, and disodium edetate to obtain antibacterial composition.
Example 5: preparation of metal salt of hinokitiol and antibacterial composition
In comparison with example 1, example 5 was only different in that potassium hydroxide was used instead of lithium hydroxide to prepare the potassium salt of hinokitiol.
Comparative example 1
Comparative example 1 differs from example 1 only in that cesium hydroxide was used instead of lithium hydroxide to prepare cesium salt of hinokitiol.
Comparative example 2
Comparative example 2 differs from example 1 only in that calcium hydroxide was used instead of lithium hydroxide to prepare the calcium salt of hinokitiol.
Comparative example 3
In comparison with example 1, comparative example 3 was only different in that silver nitrate was used instead of lithium hydroxide to prepare silver salt of hinokitiol.
Product effect test
1. Antibacterial effect test
Taking the antibacterial composition prepared in examples 1 to 5, cesium salt of hinokitiol, calcium salt of hinokitiol, silver salt of hinokitiol, and hinokitiol, citric acid, phytic acid, hydroxycitric acid, sodium citrate, sodium phytate, disodium edetate (hinokitiol, citric acid, phytic acid, hydroxycitric acid, sodium citrate, sodium phytate, disodium edetate as a control) prepared in comparative examples 1 to 3 as a sample to be tested, the sample to be tested was tested for a Minimum Inhibitory Concentration (MIC) of bacteria (including gram-positive bacteria and gram-negative bacteria, wherein gram-positive bacteria include staphylococcus aureus, bacillus cereus, bacillus subtilis, lactobacillus plantarum, gram-negative bacteria include escherichia coli, pseudomonas aeruginosa), yeast (candida albicans), mold (aspergillus niger) (concentration gradient of sample is 2000ppm, 1000ppm, 500ppm, 250ppm, 125 ppm).
The culture system was a commercially available nutrient broth (model 022010, available from Guangdong CycloKai microorganism technology Co., ltd.) and had a pH of 6, the bacteria were cultured at 36℃for 7 days, and the yeasts and molds were cultured at 28℃for 7 days, and the results are shown in Table 1.
Table 1: antibacterial Effect (data in Table 1 indicate MIC in ppm)
Remarks: in Table 1 "/" indicates no bacteriostatic effect.
As can be seen from Table 1, the antibacterial compositions prepared in examples 1 to 5 of the present invention have better antibacterial effects than hinokitiol, citric acid, phytic acid, hydroxycitric acid, sodium citrate, sodium phytate, disodium edetate. Sabina also has certain antibacterial performance, but compared with the antibacterial composition prepared in the embodiment 1-5, the antibacterial performance of the Sabina is relatively weak and the antibacterial variety is less. The antibacterial properties of the antibacterial compositions prepared in examples 1-2 were significantly better than those of the antibacterial compositions prepared in examples 3-4. The cesium salt of hinokitiol, the calcium salt of hinokitiol, and the silver salt of hinokitiol prepared in comparative examples 1 to 3 have poor antibacterial effect.
2. High temperature stability test
2.1 High temperature stability test of Metal salts of hinokitiol
The antibacterial effect of the metal salt of hinokitiol prepared in example 1 or example 3 (i.e., lithium salt of hinokitiol and sodium salt of hinokitiol) after treatment at different temperature conditions (specifically, different temperature conditions include 1 hour at room temperature 25 ℃ C., 15 minutes at high pressure wet heat treatment (101 KPa,121 ℃ C.), 1 hour at atmospheric pressure oil bath 150 ℃ C., and 1 hour at atmospheric pressure oil bath 180 ℃ C.) was measured, and the high temperature stability of the metal salt of hinokitiol prepared in example 1 or example 3 was found, and the results are shown in Table 2.
The culture system was a commercially available nutrient broth (model 022010, available from Guangdong CycloKai Biotechnology Co., ltd.) and had a pH of 6, the bacteria were cultured at 36℃for 7 days, and the yeasts and molds were cultured at 28℃for 7 days.
Table 2: antibacterial Effect (data in Table 2 indicate MIC in ppm)
It can be seen from table 2 that both the lithium salt of hinokitiol and the sodium salt of hinokitiol have good high temperature stability, and in particular, the high temperature stability of the lithium salt of hinokitiol is stronger than that of the sodium salt of hinokitiol.
2.2 High temperature stability test of antimicrobial compositions
The antibacterial compositions prepared in example 1 and example 4 were used as a control, and the antibacterial effect of the antibacterial composition prepared in example 4 was measured by treating it at different temperature conditions (specifically, different temperature conditions include 1 hour at room temperature 25 ℃,15 minutes at high pressure wet heat treatment (101 KPa,121 ℃), 1 hour at atmospheric oil bath 150 ℃ and 1 hour at atmospheric oil bath 180 ℃), and the high temperature stability of the antibacterial composition prepared in example 4 was found, and the results are shown in Table 3.
The culture system was a commercially available nutrient broth (model 022010, available from Guangdong CycloKai Biotechnology Co., ltd.) and had a pH of 6, the bacteria were cultured at 36℃for 7 days, and the yeasts and molds were cultured at 28℃for 7 days.
Table 3: antibacterial Effect (data in Table 3 indicate MIC in ppm)
As can be seen from Table 3, after the conditions of the high-pressure wet heat treatment for 1 hour, the atmospheric oil bath 150 ℃ for 1 hour, the atmospheric oil bath 180 ℃ for 1 hour, etc., the antibacterial effect of the antibacterial composition prepared in example 4 on gram-positive bacteria, gram-negative bacteria, yeasts and yeasts was kept consistent with that of the normal temperature 25 ℃, while the effect of sabinol itself on gram-negative bacteria was significantly reduced after the high-temperature treatment, indicating that the antibacterial composition prepared in example 4 of the present invention had good high-temperature stability. The antibacterial composition prepared in example 1 had an antibacterial effect superior to that of the antibacterial composition prepared in example 4.
The remaining examples produced antimicrobial compositions having high temperature stability similar to example 4 above.
3. Solubility test
The metal salt powders of hinokitiol prepared in examples 1 to 4, and hinokitiol were used as a control, and the solubility in water at 20℃was measured, and the results are shown in Table 4.
Table 4: solubility test results
| Solubility (g/100 g water) | Solubility of | |
| Sabina chinensis wood alcohol | ＜0.01 | Insoluble/poorly soluble |
| Example 1 | 0.5 | Soluble in water |
| Example 2 | 0.45 | Soluble in water |
| Example 3 | 0.40 | Soluble in water |
| Example 4 | 0.45 | Soluble in water |
As can be seen from Table 4, the metal salt powder of hinokitiol prepared in examples 1 to 4 of the present invention has better water solubility than hinokitiol, which has very important influence on the application and effect of the metal salt powder of hinokitiol.
4. Effect test for cosmetic applications
Test strain: staphylococcus aureus, escherichia coli, pseudomonas aeruginosa; fungi: aspergillus niger and Candida albicans.
Culture medium: TSB solid medium (trypticase soy peptone medium); SDB solid medium (glucose media of sand); lecithin Tween 80 nutrient agar medium and tiger red medium.
The corrosion challenge experiment comprises the following specific steps:
(1) Inoculation of the strain: preparing bacterial suspension with certain concentration after 3 generations of activation and subculture of each strain, preparing a test cosmetic sample, and then sub-packaging into 30mL or 30g packaging form, wherein after the bacterial suspension is respectively added, the bacterial content of the cosmetic sample is 1X 10 6 cfu/mL or 1X 10 6 cfu/g, and the fungal content is 1X 10 4 cfu/mL or 1X 10 4 cfu/g;
(2) Preparation of test samples: weighing 10g of sample to be detected, adding the sample into a triangular flask filled with glass beads and 90mL of sterilized normal saline, fully oscillating and uniformly mixing, standing for 15min, taking the supernatant as a 1:10 liquid to be detected, and sequentially preparing 10-time dilution series concentration gradient liquid to be detected for later use; hydrophobic sample: weighing 10g of sample to be detected, placing the sample into a sterilized mortar, adding 10mL of sterilized liquid paraffin, grinding the sample into a viscous state, adding 10mL of sterilized Tween 80, grinding the sample to be dissolved, adding 70mL of sterilized normal saline, and fully mixing the mixture in a water bath at 45 ℃ to prepare 1:10, and then sequentially preparing 10-time dilution series concentration gradient test liquid for later use;
(3) Detection of test sample: sampling and detecting at 0d, 4h, 1d, 7d, 14d, 21d and 28d (d is "day") after bacterial liquid is added according to the sampling method, adding 1mL of the prepared 10-time dilution series liquid into a sterilization flat plate, pouring a proper amount of lecithin Tween 80 nutrient agar medium or tiger red medium cooled to 45 ℃, shaking anticlockwise and uniformly mixing, making 2 parallel inverted flat plates for each dilution gradient, culturing bacteria in an incubator at 37 ℃ for 48 hours after the flat plates are solidified, counting, and culturing fungi in the incubator at 28 ℃ for 72 hours;
(4) Efficacy evaluation criteria for preservative systems:
(a) On day 28, the sample contains bacteria or mould >10 3 cfu/g (or cfu/mL), and the sample cannot pass the challenging experiment of microorganism attack, so that the preservative system of the sample cannot effectively inhibit microorganisms, and the product is easily polluted by microorganisms in production, storage and use;
(b) On day 28, the sample contains 10 2cfu/g-103 cfu/g (or cfu/mL) of bacteria, and the sample passes the challenging experiment conditionally, namely when the protein or other animal and plant material components in the product are not particularly high, and the produced sanitary environment meets the requirements, the packaging is not easy to cause secondary pollution, and the preservative system can be used, otherwise, the preservative system cannot be used;
(c) On day 28, the sample contains bacteria at 10cfu/g-100cfu/g (or cfu/mL), which shows that the preservative system of the sample has a stronger inhibiting and killing effect on microorganisms, and the product is not easy to be polluted by the microorganisms during production, storage and use through a challenge test;
(d) From day 7, bacteria in the sample is <10cfu/g (or cfu/mL), which indicates that the preservative system of the sample has extremely strong inhibition and killing effect on microorganisms, and the product is not easy to be polluted by microorganisms during production, storage and use through challenge tests.
(5) Preparation of test samples:
the components of the sample concentrate are shown in Table 5.
Table 5: essence composition meter
The antiseptic challenge results of the antimicrobial compositions prepared in examples 2 and 4 applied to the serum are shown in tables 6 and 7.
Table 6: essence antiseptic challenge results (bacteria)
Table 7: essence antiseptic challenge results (fungi)
The composition of the sample cream is shown in Table 8.
Table 8: face cream composition meter
The antiseptic challenge results of the application of the antimicrobial compositions prepared in examples 2 and 4 to creams are shown in tables 9 and 10.
Table 9: face cream antiseptic challenge results (bacteria)
Table 10: face cream antiseptic challenge result (fungus)
As can be seen from tables 6, 7, 9 and 10, in the antiseptic challenge test of the essence and the face cream, the antibacterial composition prepared in example 2 or 4 contains bacteria with the total bacterial colony count value of < 1 from day 21; from day 7, the antimicrobial composition of example 2 or 4 has a log value of the total number of fungal colonies of < 1, indicating that the preservative system of the sample containing the antimicrobial composition of example 2 or 4 has a very strong inhibitory or biocidal effect on microorganisms, indicating that the product added with the antimicrobial composition of the invention is not easily contaminated by microorganisms during production, storage and use. The antibacterial composition prepared in example 2 or 4 was replaced with the antibacterial composition prepared in example 1 or 3, and also had a similar preservative effect.
Claims (4)
1. An antibacterial composition comprising a metal salt of hinokitiol and at least one of an organic acid or an organic acid salt;
the structural formula of the metal salt of hinokitiol is shown as formula (1):
Wherein R + is Li +;
the organic acid is at least one of citric acid, hydroxycitric acid, phytic acid, ethylenediamine tetraacetic acid, malic acid or tartaric acid;
The organic acid salt is at least one selected from sodium citrate, potassium citrate, sodium phytate, potassium phytate, disodium edetate, tetrasodium edetate, disodium malate, sodium tartrate or potassium tartrate.
2. The antibacterial composition according to claim 1, wherein the antibacterial composition comprises, in parts by weight, at least one of 0.01 to 100 parts of the metal salt of hinokitiol and 0.05 to 50 parts of an organic acid or 0.05 to 80 parts of an organic acid salt.
3. A process for the preparation of an antibacterial composition according to claim 1 or 2, characterized in that it comprises the following steps:
The components are mixed to produce the antimicrobial composition.
4. Use of the antibacterial composition according to claim 1 or 2 for the preparation of daily chemicals, foods or medicines.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993017559A1 (en) * | 1992-03-13 | 1993-09-16 | Otsuka Pharmaceutical Co., Ltd. | Method of treating infectious disease, method of preventing putrefaction of cosmetic, and antibacterial/antifungal agent and cosmetic |
| JP2005255891A (en) * | 2004-03-12 | 2005-09-22 | Toyo Ink Mfg Co Ltd | Material for organic phosphorescent element and organic phosphorescent element using the same |
| CN100999451A (en) * | 2006-01-12 | 2007-07-18 | 中国农业科学院农业环境与可持续发展研究所 | Preparation method of cypressol metal compound |
| JP2009268698A (en) * | 2008-05-07 | 2009-11-19 | Toyo Aluminum Ekco Products Kk | Antibacterial sheet-like article |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993017559A1 (en) * | 1992-03-13 | 1993-09-16 | Otsuka Pharmaceutical Co., Ltd. | Method of treating infectious disease, method of preventing putrefaction of cosmetic, and antibacterial/antifungal agent and cosmetic |
| JP2005255891A (en) * | 2004-03-12 | 2005-09-22 | Toyo Ink Mfg Co Ltd | Material for organic phosphorescent element and organic phosphorescent element using the same |
| CN100999451A (en) * | 2006-01-12 | 2007-07-18 | 中国农业科学院农业环境与可持续发展研究所 | Preparation method of cypressol metal compound |
| JP2009268698A (en) * | 2008-05-07 | 2009-11-19 | Toyo Aluminum Ekco Products Kk | Antibacterial sheet-like article |
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