CN110294683A - A kind of glycine betaine phenolic acid ion salt and the preparation method and application thereof technical field - Google Patents
A kind of glycine betaine phenolic acid ion salt and the preparation method and application thereof technical field Download PDFInfo
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- CN110294683A CN110294683A CN201910420492.2A CN201910420492A CN110294683A CN 110294683 A CN110294683 A CN 110294683A CN 201910420492 A CN201910420492 A CN 201910420492A CN 110294683 A CN110294683 A CN 110294683A
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- glycine betaine
- phenolic acid
- ion salt
- acid ion
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- 229960003237 betaine Drugs 0.000 title claims abstract description 158
- -1 glycine betaine phenolic acid ion salt Chemical class 0.000 title claims abstract description 115
- 238000002360 preparation method Methods 0.000 title claims abstract description 36
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims abstract description 55
- 150000007965 phenolic acids Chemical class 0.000 claims abstract description 46
- 239000012266 salt solution Substances 0.000 claims abstract description 20
- 239000003960 organic solvent Substances 0.000 claims abstract description 14
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 230000008025 crystallization Effects 0.000 claims abstract description 8
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 claims description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- JMSVCTWVEWCHDZ-UHFFFAOYSA-N syringic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1O JMSVCTWVEWCHDZ-UHFFFAOYSA-N 0.000 claims description 29
- 235000004515 gallic acid Nutrition 0.000 claims description 20
- 229940074391 gallic acid Drugs 0.000 claims description 20
- YIBXWXOYFGZLRU-UHFFFAOYSA-N syringic aldehyde Natural products CC12CCC(C3(CCC(=O)C(C)(C)C3CC=3)C)C=3C1(C)CCC2C1COC(C)(C)C(O)C(O)C1 YIBXWXOYFGZLRU-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 8
- 230000008014 freezing Effects 0.000 claims description 7
- 238000007710 freezing Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- XOXYHGOIRWABTC-UHFFFAOYSA-N gentisin Chemical compound C1=C(O)C=C2C(=O)C3=C(O)C=C(OC)C=C3OC2=C1 XOXYHGOIRWABTC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 244000269722 Thea sinensis Species 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
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- 239000003814 drug Substances 0.000 claims description 5
- 235000019441 ethanol Nutrition 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 2
- 235000015872 dietary supplement Nutrition 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 235000009499 Vanilla fragrans Nutrition 0.000 claims 1
- 244000263375 Vanilla tahitensis Species 0.000 claims 1
- 235000012036 Vanilla tahitensis Nutrition 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 21
- 239000000178 monomer Substances 0.000 abstract description 14
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000000047 product Substances 0.000 description 10
- YQUVCSBJEUQKSH-UHFFFAOYSA-N protochatechuic acid Natural products OC(=O)C1=CC=C(O)C(O)=C1 YQUVCSBJEUQKSH-UHFFFAOYSA-N 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 230000000259 anti-tumor effect Effects 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 238000001291 vacuum drying Methods 0.000 description 5
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 235000016068 Berberis vulgaris Nutrition 0.000 description 4
- 241000335053 Beta vulgaris Species 0.000 description 4
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 4
- 244000223014 Syzygium aromaticum Species 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- 230000003078 antioxidant effect Effects 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 229940114119 gentisate Drugs 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 230000005311 nuclear magnetism Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002091 cationic group Chemical group 0.000 description 3
- 230000036541 health Effects 0.000 description 3
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- 230000000144 pharmacologic effect Effects 0.000 description 3
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- 235000006793 Artemisia stelleriana Nutrition 0.000 description 2
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- 241000544061 Cuculus canorus Species 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 235000006486 human diet Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000036651 mood Effects 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 229930000044 secondary metabolite Natural products 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 2
- BBJUSJOGHYQDQX-WODDMCJRSA-N (2S)-4-[(E)-2-[(2S)-2-carboxy-5,6-dihydroxy-2,3-dihydroindol-1-yl]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid Chemical compound OC(=O)[C@@H]1Cc2cc(O)c(O)cc2N1\C=C\C1=CC(=N[C@@H](C1)C(O)=O)C(O)=O BBJUSJOGHYQDQX-WODDMCJRSA-N 0.000 description 1
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 235000006576 Althaea officinalis Nutrition 0.000 description 1
- 244000208874 Althaea officinalis Species 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 208000004429 Bacillary Dysentery Diseases 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 235000004385 Conyza canadensis Nutrition 0.000 description 1
- 244000074881 Conyza canadensis Species 0.000 description 1
- 241000186427 Cutibacterium acnes Species 0.000 description 1
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 1
- 241001269238 Data Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 240000006927 Foeniculum vulgare Species 0.000 description 1
- 206010017915 Gastroenteritis shigella Diseases 0.000 description 1
- 206010018498 Goitre Diseases 0.000 description 1
- 241001453894 Lindsaeaceae Species 0.000 description 1
- 241000219071 Malvaceae Species 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241001531309 Quercus infectoria Species 0.000 description 1
- 241000208422 Rhododendron Species 0.000 description 1
- 241000681946 Rhododendron dauricum Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 229930003268 Vitamin C Natural products 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- FPFIFCBPMJFKJR-LLVKDONJSA-M betanidin Natural products O=C([O-])[C+]1/[N+](=C/C=C/2\C=C(C(=O)O)N[C@@H](C(=O)O)C\2)/c2c(cc(O)c(O)c2)C1 FPFIFCBPMJFKJR-LLVKDONJSA-M 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 229940074360 caffeic acid Drugs 0.000 description 1
- 235000004883 caffeic acid Nutrition 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- BCAARMUWIRURQS-UHFFFAOYSA-N dicalcium;oxocalcium;silicate Chemical compound [Ca+2].[Ca+2].[Ca]=O.[O-][Si]([O-])([O-])[O-] BCAARMUWIRURQS-UHFFFAOYSA-N 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000003631 expected effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 201000003872 goiter Diseases 0.000 description 1
- 230000023597 hemostasis Effects 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 201000002037 lung adenoma Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 230000000065 osmolyte Effects 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 235000009048 phenolic acids Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229940055019 propionibacterium acne Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 201000005113 shigellosis Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- 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
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
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- Communicable Diseases (AREA)
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- Birds (AREA)
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- Pain & Pain Management (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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- Nutrition Science (AREA)
- Food Science & Technology (AREA)
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- Emergency Medicine (AREA)
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- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention discloses a kind of glycine betaine phenolic acid ion salt and the preparation method and application thereof, wherein, the preparation method of the glycine betaine phenolic acid ion salt is comprising steps of at a predetermined temperature, phenolic acid and glycine betaine are added in organic solvent, obtain glycine betaine phenolic acid ion salt solution, crystallization operation is carried out to the glycine betaine phenolic acid ion salt solution, obtains glycine betaine phenolic acid ion salt.Glycine betaine phenolic acid ion salt produced by the present invention has effects that phenolic acid and glycine betaine and bioactivity, and its water-soluble two order of magnitude higher than monomer phenolic acid simultaneously, can effectively improve the trap of phenolic acid monomer and enhance its application effect.
Description
The present invention relates to medicine, compound field used for cosmetic more particularly to a kind of glycine betaine phenolic acid ion salt and its systems
Preparation Method and application.
Background technique
Glycine betaine is also known as trimethylaminyl ethlyl lactone or betanidin, is a kind of quaternary amine type alkaloid, is widespread in nature.
Intermediate product of the glycine betaine as animal metabolism is excellent methyl donor and Osmolyte regulator, in the metabolism of nutriment
It plays a very important role.Studies have shown that glycine betaine has the effects that osmotic adjustment, antitumor, help to maintain liver, the heart
The health of blood vessel, enteron aisle and kidney possesses excellent bioactivity and pharmacological activity.But in view of the pharmacological activity of glycine betaine itself
It is not very strong and lower bioavailability, it is often necessary to be used in combination with other active components and can be only achieved expected effect
Fruit, to limit its application range.
Therefore, the existing technology needs to be improved and developed.
Summary of the invention
In view of above-mentioned deficiencies of the prior art, the purpose of the present invention is to provide a kind of glycine betaine phenolic acid ion salt and its systems
Preparation Method and application, it is intended to by glycine betaine and natural phenolic acid at salt split, solve existing glycine betaine monomer in application process
In there are problems that pharmacological activity is not strong, bioavailability is low etc..
Technical scheme is as follows:
A kind of preparation method of glycine betaine phenolic acid ion salt, wherein the following steps are included:
At a predetermined temperature, phenolic acid and glycine betaine are added in organic solvent, obtain glycine betaine phenolic acid ion salt solution；
Crystallization operation is carried out to the glycine betaine phenolic acid ion salt solution, obtains glycine betaine phenolic acid ion salt.
The preparation method of the glycine betaine phenolic acid ion salt, wherein the step at a predetermined temperature, by phenolic acid and beet
Alkali is added in organic solvent, is obtained glycine betaine phenolic acid ion salt solution, is specifically included:
In atmosphere of inert gases, phenolic acid is mixed in organic solvent at a predetermined temperature with glycine betaine, reacts the predetermined time,
Obtain glycine betaine phenolic acid ion salt solution.
The preparation method of the glycine betaine phenolic acid ion salt, wherein the step is molten to the glycine betaine phenolic acid ion salt
Liquid carries out crystallization operation, obtains glycine betaine phenolic acid ion salt, specifically includes:
Under vacuum conditions, be concentrated simultaneously freezing and crystallizing to the glycine betaine phenolic acid ion salt solution, obtain glycine betaine phenolic acid
Ion salt.
The preparation method of the glycine betaine phenolic acid ion salt, wherein mole that the phenolic acid and the glycine betaine mix
Than for 1:1.2-1.8.
The preparation method of the glycine betaine phenolic acid ion salt, wherein the predetermined temperature is 30-100 DEG C.
The preparation method of the glycine betaine phenolic acid ion salt, wherein the phenolic acid is vanillic acid, syringic acid, gallic acid
Any one of with gentianic acid.
The preparation method of the glycine betaine phenolic acid ion salt, wherein the organic solvent is acetonitrile, methanol, ethyl alcohol and second
One of glycol is a variety of.
The preparation method of the glycine betaine phenolic acid ion salt, wherein the predetermined time is 12-24h.
A kind of glycine betaine phenolic acid ion salt, wherein the glycine betaine phenolic acid ion salt uses glycine betaine phenolic acid described above
The preparation method of ion salt is prepared.
A kind of application of glycine betaine phenolic acid ion salt, wherein the glycine betaine phenolic acid ion salt is used as cosmetics
Formula material, nutritional supplement raw material or medicine material.
The utility model has the advantages that the present invention is that cationic presoma passes through ionization using phenolic acid as anion presoma with glycine betaine
Salt-forming reaction synthesizing betaine phenolic acid ion salt realizes isolating and purifying for product by condensing crystallizing after reaction.The present invention
Glycine betaine phenolic acid ion salt obtained has the effect that first, compared with monomer phenolic acid, after at salt split, glycine betaine phenol
The irritation of acid ion salt is substantially reduced, while significantly improving dissolubility, to substantially increase trap, enhances application
Effect；Second, the main body of glycine betaine and phenolic acid monomer has been fully retained in the glycine betaine phenolic acid ion salt of generation after at salt split
Molecular skeleton and functional group, thus have bioactivity and effect there are two types of substance simultaneously, and for anti-inflammatory, antitumor etc. two kinds
For substance has effects that simultaneously, at will have significant reinforcing effect after salt.
Detailed description of the invention
Fig. 1 is a kind of flow chart of the preparation method preferred embodiment of glycine betaine phenolic acid ion salt of the present invention.
Fig. 2 is glycine betaine gallate nucleus magnetic hydrogen spectrum figure.
Fig. 3 is glycine betaine syringic acid salt nuclear-magnetism hydrogen spectrogram.
Fig. 4 is glycine betaine vanillate nucleus magnetic hydrogen spectrum figure.
Fig. 5 is glycine betaine gentisate nucleus magnetic hydrogen spectrum figure.
Specific embodiment
The present invention provides a kind of glycine betaine phenolic acid ion salt and the preparation method and application thereof, for make the purpose of the present invention,
Technical solution and effect are clearer, clear, and the present invention is described in more detail below.It should be appreciated that described herein
Specific examples are only used to explain the present invention, is not intended to limit the present invention.
Referring to Fig. 1, Fig. 1 provides a kind of stream of the preparation method preferred embodiment of glycine betaine phenolic acid ion salt for the present invention
Cheng Tu, as shown, it includes the following steps:
Phenolic acid and glycine betaine are added in organic solvent, obtain glycine betaine phenolic acid ion salt solution by S10, at a predetermined temperature；
S20, crystallization operation is carried out to the glycine betaine phenolic acid ion salt solution, obtains glycine betaine phenolic acid ion salt.
Specifically, glycine betaine phenolate provided by the present invention is cationic presoma with glycine betaine, is yin with phenolic acid
Ion presoma is realized by condensing crystallizing after reaction by being ionized into reactant salt synthesizing betaine phenolic acid ion salt
Product isolates and purifies, and has obtained glycine betaine phenolic acid ion salt, and the preparation method is made using usual vehicle simple and easy to get
For reaction medium, instrument and reaction condition are also easily achieved, and synthesis step is succinct, convenient post-treatment, and products obtained therefrom is pure
Degree is high, high income, can meet general Study requirement.
In above-mentioned preparation method provided by the present invention, the phenolic acid is widely present in plant as Secondary metabolites
It is that the very wide element of the first species is distributed in human diet in object cell.Natural phenolic acid have multiple biological activities, human body and other
In animal body, remove free radical, in addition to anti-oxidant, antitumor, bacteria resistance function except having, also have and inhibit fat, improve mood and
Promote the functions such as human body intestinal canal health.However, the water solubility of most natural phenolic acids is very poor, and the bioactivity phase of phenolic acid monomer
To weaker, to limit its application effect and application range.Using natural phenolic acid as anion presoma pair in the present invention
After glycine betaine carries out Ionization Modification, available one kind it is pure natural there are excellent performances such as anti-oxidant, anti-inflammatory, antitumor
The water solubility of glycine betaine phenolic acid ion salt, the glycine betaine phenolic acid ion salt increases significantly compared with monomer phenolic acid, thus
Trap is substantially increased, application effect is enhanced.
The phenolic acid is widely present in plant cell as Secondary metabolites, is to be distributed in human diet very extensively
The element of the first species.Common natural phenolic acid has multiple biological activities, in human body and other animal bodies, removes freely except having
Outside base, anti-oxidant, antitumor, bacteria resistance function, also have and inhibit fat, improve mood and promotes the functions such as human body intestinal canal health.
In one or more embodiments, the phenolic acid is syringic acid, gallic acid, vanillic acid, gentianic acid, caffeic acid
One of Deng, but not limited to this.
In a kind of specific embodiment, when the phenolic acid is syringic acid, then the syringic acid and glycine betaine are existed
It is mixed under predetermined temperature in organic solvent, the syringic acid and glycine betaine is made to be ionized into reactant salt, sweet tea is made
Dish alkali cloves acid salt solution.The syringic acid can be from compositae plant knitting wool careless (Artemisia stelleriana, Horseweed Herb), overground part ericad
Rhododendron dauricum, leaf korean rhododendron, Ye Baihua cuckoo, Ye little Hua cuckoo, leaf umbelliferae fennel, leaf Lindsaeaceae plant Stenoloma chusana
, leaf malvaceae plant Althaea officinalis and leaf Fagaceae gall oak goitre in extract and obtain, syringic acid has stronger antioxygen
Change and antibacterial action are the main antibiotic effective ingredient of Artemisia stelleriana, play the role of antibacterium and fungi, the cloves acid monomers are 25
Water solubility under the conditions of DEG C is about 7 mmolL-1, prepared by water-soluble > of glycine betaine cloves hydrochlorate under the conditions of 25 DEG C
1000 mmol·L-1.The glycine betaine cloves hydrochlorate has the bioactivity and function of two kinds of substances of syringic acid and glycine betaine simultaneously
Effect, and the trap of syringic acid and glycine betaine is substantially increased, enhance its application effect.
In a kind of specific embodiment, when the phenolic acid is gallic acid, then by the gallic acid and beet
Alkali mixes in organic solvent under predetermined temperature, and the gallic acid and glycine betaine is made to be ionized into reactant salt,
Glycine betaine gallic acid salting liquid is made.The gallic acid has bacteriostasis to 17 kinds of fungies under 3% concentration, to influenza
Virus also has certain inhibiting effect, can treat bacillary dysentery；It has convergence, hemostasis, anti-diarrhea effect, to caused by morpholine plus sodium nitrite
Mouse lung adenoma has high inhibition effect.Water solubility of gallic acid under the conditions of 25 DEG C is about 71 mmolL-1, and be made
Water-soluble > 1000 mmolL of glycine betaine gallate under the conditions of 25 DEG C-1.The glycine betaine gallate is same
When have effects that the bioactivity of two kinds of substances of gallic acid and glycine betaine and, and substantially increase gallic acid and glycine betaine
Trap, enhance its application effect.
In one or more embodiments, the organic solvent is one in acetonitrile, methanol, ethyl alcohol and ethylene glycol etc.
Kind.It is furthermore preferred that the solvent is methanol, to improve the Crystallization Separation effect of product.
In one or more embodiments, the ratio for being 1:1.2-1.8 according to the molar ratio of phenolic acid and glycine betaine, by institute
It states phenolic acid and glycine betaine to mix under predetermined temperature in organic solvent, is ionized into the phenolic acid and glycine betaine
Glycine betaine phenolic acid ion salt solution is made in reactant salt.It is furthermore preferred that the molar ratio of the phenolic acid and glycine betaine is 1:1.3-1.6.
In one or more embodiments, phenolic acid and glycine betaine are blended under the conditions of 30-100 DEG C of temperature organic
In solvent, after so that the phenolic acid and glycine betaine is ionized into reactant salt 12-24h, glycine betaine phenolic acid ion salt solution is made.
Under the reaction temperature, not only there is faster reaction rate, but also the generation of side reaction can be effectively suppressed；Under the reaction time,
It can promote fully reacting between phenolic acid and glycine betaine.
In some embodiments, the glycine betaine phenolic acid ion salt solution is concentrated into its volume under vacuum conditions
When 1/5 to 1/10, then freezing and crystallizing is carried out, pure glycine betaine phenolic acid ion salt is made.
It in some embodiments, further include step after carrying out Freeze crystallization to the glycine betaine phenolic acid ion salt solution
It is rapid: separation and vacuum drying are successively filtered to glycine betaine phenolic acid ion salt obtained, wherein drying time 24-48h,
Thoroughly to remove the residual solvent in product.
After the present invention carries out Ionization Modification to glycine betaine using natural phenolic acid as anion presoma, the beet of generation
Host molecule skeleton and the functional group of glycine betaine and phenolic acid monomer has been fully retained in alkali phenolic acid ion salt, thus simultaneously there are two types of tool
The bioactivity and effect of substance, and for two kinds of substances such as anti-inflammatory, antitumor have effects that simultaneously, will have at after salt
There is significant reinforcing effect.
Further, the present invention reacts generation with glycine betaine to different types of phenolic acid monomer under the conditions of 25 DEG C of temperature
Glycine betaine phenolic acid ion salt and the water solubility datas of various phenolic acid monomers be tested, specifically, the glycine betaine phenol
Acid ion salt it is water-soluble shown in the experimental data are shown in the following table:
Water solubility relatively (mmolL-1, 25℃)
| Gallic acid | Syringic acid | Vanillic acid | Gentianic acid | |
| Phenolic acid monomer | 71 | 7 | 10 | 4 |
| Glycine betaine phenolic acid ion salt | > 1000 | > 1000 | > 1000 | > 1000 |
By comparison, it was found that the water solubility of the glycine betaine phenolic acid ion salt improves two order of magnitude left sides compared with monomer phenolic acid
The right side enhances its application effect to substantially increase its trap.
Further, the present invention tests the minimum inhibitory concentration (MIC) of glycine betaine phenolic acid ion salt, specifically, institute
The bacteriostatic experiment data for stating glycine betaine phenolic acid ion salt are as shown in the table:
Minimum inhibitory concentration (MIC)
By test result as can be seen that four kinds of glycine betaine phenolic acid ion salts are to candida albicans, Escherichia coli, black song
Mould, Pseudomonas aeruginosa, staphylococcus aureus and propionibacterium acnes etc. all have good fungistatic effect, can significantly inhibit thin
The growth of bacterium, fungi and mould etc..
Based on above-mentioned preparation method, the present invention also provides a kind of glycine betaine phenolic acid ion salts, wherein using as described above
The preparation method of glycine betaine phenolic acid ion salt is prepared.
Further, the present invention also provides a kind of applications of glycine betaine phenolic acid ion salt, wherein by institute of the embodiment of the present invention
The glycine betaine phenolic acid ion salt stated is used as the formula material of cosmetics；Alternatively, by glycine betaine phenolic acid described in the embodiment of the present invention
Ion salt is used as the medicinal ingredient of the drugs such as antitumor, anticancer.In other words, glycine betaine phenolic acid ion salt described in the present embodiment
Anti-inflammatory bactericidal agent, mite killing be can not only be used for except acne agent and moisturizer etc. are used for the formula material of cosmetics, be also used as it is anti-inflammatory,
The raw material of the drugs such as antitumor, anticancer.
Below by specific embodiment, the invention will be further described.
Embodiment 1
The preparation method of the present embodiment glycine betaine gallic acid ion salt, comprising the following steps:
Under nitrogen atmosphere, 0.01 mol gallic acid is dissolved in reactor with the methanol of 30 ml, it is molten with the methanol of 20 ml
0.01 mol glycine betaine is solved, and is added dropwise in the reactor dissolved with gallic acid, 60 DEG C is heated to, is ionized into reactant salt
12 hours；
After completion of the reaction, under vacuum conditions concentrate solution to reaction solution 1/10, freezing and crystallizing, and be filtered, washed point
From glycine betaine gallic acid ion salt crystalline product is obtained, drying obtain purity in 48 hours in a vacuum drying oven is more than 99%
Glycine betaine gallic acid ion salt 2.68g, yield 93.32%.
As shown in Fig. 2, the nucleus magnetic hydrogen spectrum data of glycine betaine gallic acid ion salt are made in the present embodiment are as follows:1H NMR
(400 MHz, MeOD) δ 7.06 (s, 2H), 3.84 (s, 2H), 3.26 (s, 9H)；Nuclear-magnetism carbon modal data are as follows:13C
NMR (101 MHz, MeOD) δ 169.05, 167.46, 145.07, 138.21, 120.71, 108.97, 65.83,
52.48, 52.44, 52.40.The fusing point that glycine betaine gallic acid ion salt is made in the present embodiment is 206-208 DEG C.
Embodiment 2
The preparation method of the present embodiment glycine betaine syringic acid ion salt, comprising the following steps:
Under nitrogen atmosphere, 0.01 mol syringic acid is dissolved in reactor with the methanol of 25 ml, is dissolved with the methanol of 20 ml
0.01 mol glycine betaine, and be added dropwise in the reactor dissolved with gallic acid, 50 DEG C are heated to, reactant salt 16 is ionized into
Hour；
After completion of the reaction, under vacuum conditions concentrate solution to reaction solution 1/6, freezing and crystallizing, and be filtered, washed separation
Glycine betaine syringic acid ion salt crystalline product is obtained, dries in a vacuum drying oven 48 hours and obtains the sweet tea that purity is more than 99%
Dish alkali syringic acid ion salt 2.95g, yield 93.51%.
As shown in figure 3, the nucleus magnetic hydrogen spectrum data of glycine betaine syringic acid ion salt are made in the present embodiment are as follows:1H NMR (400
MHz, MeOD) δ 7.32 (s, 2H), 3.88 (s, 6H), 3.85 (s, 2H), 3.28 (s, 9H)；Nuclear-magnetism carbon spectrum
Data are as follows:13C NMR (101 MHz, MeOD) δ 168.62, 167.40, 147.46, 140.29, 120.67,
106.91, 65.81, 55.41, 52.47, 52.43, 52.39.The molten of glycine betaine syringic acid ion salt is made in the present embodiment
Point is 190-195 DEG C.
Embodiment 3
The preparation method of the present embodiment glycine betaine vanillic acid ion salt, comprising the following steps:
Under nitrogen atmosphere, 0.01 mol vanillic acid is dissolved in reactor with the methanol of 35 ml, is dissolved with the methanol of 20 ml
0.01 mol glycine betaine, and be added dropwise in the reactor dissolved with vanillic acid, 65 DEG C are heated to, it is small to be ionized into reactant salt 16
When；
After completion of the reaction, under vacuum conditions concentrate solution to reaction solution 1/8, freezing and crystallizing, and be filtered, washed separation
Glycine betaine vanillic acid ion salt crystalline product is obtained, dries in a vacuum drying oven 48 hours and obtains the sweet tea that purity is more than 99%
Dish alkali vanillic acid ion salt 2.66g, yield 93.23%.
As shown in figure 4, the nucleus magnetic hydrogen spectrum data of glycine betaine vanillic acid ion salt are made in the present embodiment are as follows:1H NMR (400
MHz, MeOD) δ 7.55 (dq, J = 3.7, 1.9 Hz, 2H), 6.89 – 6.79 (m, 1H), 3.89 (s,
3H), 3.85 (s, 2H), 3.27 (s, 9H)；Nuclear-magnetism carbon modal data are as follows:13C NMR (101 MHz, MeOD) δ
168.70, 167.41, 151.27, 147.29, 123.90, 121.80, 114.50, 112.42, 65.79, 55.03,
52.47, 52.43, 52.39.The fusing point that glycine betaine vanillic acid ion salt is made in the present embodiment is 171-173 DEG C.
Embodiment 4
The preparation method of the present embodiment glycine betaine gentianic acid ion salt, comprising the following steps:
Under nitrogen atmosphere, 0.01 mol gentianic acid is dissolved in reactor with the methanol of 40ml, is dissolved with the methanol of 20 ml
0.01 mol glycine betaine, and be added dropwise in the reactor dissolved with gentianic acid, 70 DEG C are heated to, it is small to be ionized into reactant salt 24
When；
After completion of the reaction, under vacuum conditions concentrate solution to reaction solution 1/10, freezing and crystallizing, and be filtered, washed point
From glycine betaine gentisate crystalline product is obtained, dries in a vacuum drying oven 48 hours and obtain the beet that purity is more than 99%
Alkali gentisate 2.52g, yield 92.89%.
As shown in figure 5, the nucleus magnetic hydrogen spectrum data of glycine betaine gentisate are made in the present embodiment are as follows:1H NMR (400 MHz,
MeOD) δ 7.26 (d, J=3.1 Hz, 1H), 6.94 (dd, J=8.9, 3.1 Hz, 1H), 6.76 (d, J =
8.9 Hz, 1H), 3.90 (s, 2H), 3.28 (s, 9H).The present embodiment be made glycine betaine gentisate fusing point be
198-203℃。
In conclusion a kind of glycine betaine phenolic acid ion salt provided by the invention and the preparation method and application thereof.The present invention with
Glycine betaine is cationic presoma, using phenolic acid as anion presoma, by be ionized into reactant salt synthesizing betaine phenolic acid from
Alite realizes isolating and purifying for product by condensing crystallizing after reaction.The glycine betaine phenolic acid ion salt is natural ion
Salt, antioxidant activity is higher than or is equivalent to vitamin C, water-soluble two numbers magnitude higher than monomer phenolic acid, and has simultaneously
There are the effect of phenolic acid and glycine betaine and bioactivity.
It should be understood that the application of the present invention is not limited to the above for those of ordinary skills can
With improvement or transformation based on the above description, all these modifications and variations all should belong to the guarantor of appended claims of the present invention
Protect range.
Claims (10)
1. a kind of preparation method of glycine betaine phenolic acid ion salt, which comprises the following steps:
At a predetermined temperature, phenolic acid and glycine betaine are added in organic solvent, obtain glycine betaine phenolic acid ion salt solution；
Crystallization operation is carried out to the glycine betaine phenolic acid ion salt solution, obtains glycine betaine phenolic acid ion salt.
2. the preparation method of glycine betaine phenolic acid ion salt according to claim 1, which is characterized in that the step is in predetermined temperature
Under degree, phenolic acid and glycine betaine are added in organic solvent, glycine betaine phenolic acid ion salt solution is obtained, specifically includes:
In atmosphere of inert gases, phenolic acid is mixed in organic solvent at a predetermined temperature with glycine betaine, reacts the predetermined time,
Obtain glycine betaine phenolic acid ion salt solution.
3. the preparation method of glycine betaine phenolic acid ion salt according to claim 1, which is characterized in that the step is to the sweet tea
Dish alkali phenolic acid ion salt solution carries out crystallization operation, obtains glycine betaine phenolic acid ion salt, specifically includes:
Under vacuum conditions, be concentrated simultaneously freezing and crystallizing to the glycine betaine phenolic acid ion salt solution, obtain glycine betaine phenolic acid
Ion salt.
4. the preparation method of glycine betaine phenolic acid ion salt according to claim 1, which is characterized in that the phenolic acid and the sweet tea
The molar ratio that dish alkali mixes is 1:1.2-1.8.
5. the preparation method of glycine betaine phenolic acid ion salt according to claim 1, which is characterized in that the predetermined temperature is
30-100℃。
6. the preparation method of glycine betaine phenolic acid ion salt according to claim 1, which is characterized in that the phenolic acid is vanilla
Any one of acid, syringic acid, gallic acid and gentianic acid.
7. the preparation method of glycine betaine phenolic acid ion salt according to claim 1, which is characterized in that the organic solvent is second
One of nitrile, methanol, ethyl alcohol and ethylene glycol are a variety of.
8. the preparation method of glycine betaine phenolic acid ion salt according to claim 2, which is characterized in that the predetermined time is
12-24h。
9. a kind of glycine betaine phenolic acid ion salt, which is characterized in that the glycine betaine phenolic acid ion salt is any using claim 1-8
The preparation method of the glycine betaine phenolic acid ion salt is prepared.
10. a kind of application of glycine betaine phenolic acid ion salt, which is characterized in that by glycine betaine phenolic acid ion as claimed in claim 9
Salt is used as formula material, nutritional supplement raw material or the medicine material of cosmetics.
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