CN103694084A - Preparation method and application of water-soluble compound of menthol - Google Patents
Preparation method and application of water-soluble compound of menthol Download PDFInfo
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- CN103694084A CN103694084A CN201310720755.4A CN201310720755A CN103694084A CN 103694084 A CN103694084 A CN 103694084A CN 201310720755 A CN201310720755 A CN 201310720755A CN 103694084 A CN103694084 A CN 103694084A
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- mentha camphor
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- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 title abstract description 57
- 229940041616 menthol Drugs 0.000 title abstract description 57
- 150000001875 compounds Chemical class 0.000 title abstract description 14
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 title abstract 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 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 claims abstract description 12
- 239000011734 sodium Substances 0.000 claims abstract description 12
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 12
- 159000000000 sodium salts Chemical class 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 6
- 239000012299 nitrogen atmosphere Substances 0.000 claims abstract description 6
- 239000011591 potassium Substances 0.000 claims abstract description 6
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 5
- 238000012545 processing Methods 0.000 claims abstract description 4
- 239000000126 substance Substances 0.000 claims abstract description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims abstract 2
- 235000011164 potassium chloride Nutrition 0.000 claims abstract 2
- 239000001103 potassium chloride Substances 0.000 claims abstract 2
- NOOLISFMXDJSKH-KXUCPTDWSA-N (-)-Menthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1O NOOLISFMXDJSKH-KXUCPTDWSA-N 0.000 claims description 64
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 230000000844 anti-bacterial effect Effects 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- 235000013361 beverage Nutrition 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- 229960004873 levomenthol Drugs 0.000 claims 13
- 230000001476 alcoholic effect Effects 0.000 claims 4
- 238000011034 membrane dialysis Methods 0.000 claims 2
- 229940088710 antibiotic agent Drugs 0.000 claims 1
- 230000006837 decompression Effects 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract description 8
- 239000012528 membrane Substances 0.000 abstract description 6
- 238000001035 drying Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 210000004379 membrane Anatomy 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 238000000502 dialysis Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000003204 osmotic effect Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 235000016257 Mentha pulegium Nutrition 0.000 description 3
- 244000246386 Mentha pulegium Species 0.000 description 3
- 235000004357 Mentha x piperita Nutrition 0.000 description 3
- 235000001050 hortel pimenta Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- -1 Ammonium fluorosilicate Chemical compound 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 description 2
- 235000002899 Mentha suaveolens Nutrition 0.000 description 2
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 2
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 235000013312 flour Nutrition 0.000 description 2
- 235000015203 fruit juice Nutrition 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- 229940051866 mouthwash Drugs 0.000 description 2
- 235000015927 pasta Nutrition 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229960000502 poloxamer Drugs 0.000 description 2
- 229920001983 poloxamer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 229940034610 toothpaste Drugs 0.000 description 2
- 239000000606 toothpaste Substances 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 201000008197 Laryngitis Diseases 0.000 description 1
- 235000004347 Perilla Nutrition 0.000 description 1
- 241000229722 Perilla <angiosperm> Species 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 239000002386 air freshener Substances 0.000 description 1
- 230000001139 anti-pruritic effect Effects 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical class [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 230000002026 carminative effect Effects 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019543 dairy drink Nutrition 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/68—Preparation of metal alcoholates
- C07C29/70—Preparation of metal alcoholates by converting hydroxy groups to O-metal groups
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/145—Acids, anhydrides or salts thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
-
- 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
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- A—HUMAN NECESSITIES
- 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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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Nutrition Science (AREA)
- Polymers & Plastics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
技术领域 technical field
本发明属于化工技术领域，具体涉及薄荷脑的水溶性化合物的制备方法及其应用。 The invention belongs to the technical field of chemical industry, and in particular relates to a preparation method and an application of a water-soluble compound of menthol.
背景技术 Background technique
一种化学药剂，薄荷脑系由薄荷的叶和茎中所提取，白色晶体，分子式C10H20O，为薄荷和欧薄荷精油中的主要成分。中国和巴西是主要的天然薄荷生产国，薄荷脑和消旋薄荷脑均可用作牙膏、香水、饮料和糖果等的赋香剂；在医药上用作刺激药，作用于皮肤或粘膜，有清凉止痒作用；内服可作为驱风药，用于头痛及鼻、咽、喉炎症等；其酯用于香料和药物；其又是高级香料，还是重要的化工原料。 A chemical agent, menthol is extracted from the leaves and stems of peppermint. It is a white crystal with molecular formula C 10 H 20 O. It is the main component of peppermint and peppermint essential oils. China and Brazil are the main natural mint producing countries. Both menthol and racemic menthol can be used as flavoring agents for toothpaste, perfume, beverages and candies; they are used as stimulants in medicine, acting on the skin or mucous membranes. Cooling and antipruritic effect; oral administration can be used as a carminative for headaches and inflammation of the nose, pharynx, and laryngitis; its esters are used in spices and medicines; it is also a high-grade spice and an important chemical raw material.
性状：该品为无色针状或棱柱状结晶或白色结晶性粉末；有薄荷的特殊香气，味初灼热后清凉；乙醇溶液显中性反应；在乙醇、氯仿、乙醚、液状石蜡或挥发油中极易溶解，在水中极微溶解，熔点：应为42～44℃ Properties: This product is colorless needle-like or prismatic crystal or white crystalline powder; it has a special aroma of mint, and tastes cool after burning hot at first; neutral reaction in ethanol solution; in ethanol, chloroform, ether, liquid paraffin or volatile oil Very soluble, very slightly soluble in water, melting point: should be 42-44°C
能溶于醇和醚，不溶于水。由于薄荷脑不溶于水的特性，对其开发利用带来了不必要的麻烦。 Soluble in alcohol and ether, insoluble in water. Due to the water-insoluble characteristics of menthol, unnecessary troubles have been brought to its development and utilization.
发明内容 Contents of the invention
针对现有技术存在的问题，本发明的目的在于设计提供一种薄荷脑的水溶性化合物的制备方法及其应用的技术方案。 Aiming at the problems existing in the prior art, the object of the present invention is to design and provide a technical solution for a preparation method of a water-soluble compound of menthol and its application.
所述的薄荷脑的水溶性化合物的制备方法，其特征在于包括以下工艺步骤： The preparation method of the water-soluble compound of menthol is characterized in that comprising the following processing steps:
1）氮气气氛下，在薄荷脑的醚或醇溶液中加入钠或钾，并进行缓慢搅拌充分反应，静置，过夜； 1) Under a nitrogen atmosphere, add sodium or potassium to the ether or alcohol solution of menthol, and carry out slow stirring to fully react, let it stand overnight;
2）将步骤1）得到的混合物过滤浓缩，洗涤，干燥，收集固体； 2) The mixture obtained in step 1) was concentrated by filtration, washed, dried, and the solid was collected;
3）将步骤2）得到的固体溶解于水，再采用渗透膜渗析，然后减压除水，得到薄荷脑的水溶性钠盐或钾盐。 3) Dissolving the solid obtained in step 2) in water, dialysis with an osmotic membrane, and then removing water under reduced pressure to obtain a water-soluble sodium or potassium salt of menthol.
所述的薄荷脑的水溶性化合物的制备方法，其特征在于所述的步骤1）中薄荷脑与钠或钾的摩尔比为1:1.1～1.3。 The preparation method of the water-soluble compound of menthol is characterized in that the molar ratio of menthol to sodium or potassium in the step 1) is 1:1.1-1.3.
所述的薄荷脑的水溶性化合物的制备方法，其特征在于所述的步骤1）中搅拌反应温度为24～28℃，搅拌反应时间500～700分钟。 The preparation method of the water-soluble compound of menthol is characterized in that the stirring reaction temperature in the step 1) is 24-28° C., and the stirring reaction time is 500-700 minutes.
所述的薄荷脑的水溶性化合物的制备方法，其特征在于所述的步骤1）中醚溶液为乙醚或四氢呋喃，醇溶液为乙醇。 The preparation method of the water-soluble compound of menthol is characterized in that in the step 1), the ether solution is diethyl ether or tetrahydrofuran, and the alcohol solution is ethanol.
所述的薄荷脑的水溶性化合物的制备方法，其特征在于所述的步骤2）中洗涤采用醚或醇溶液，所述的醚溶液为乙醚或四氢呋喃，醇溶液为乙醇。 The preparation method of the water-soluble compound of menthol is characterized in that ether or alcohol solution is used for washing in the step 2), the ether solution is diethyl ether or tetrahydrofuran, and the alcohol solution is ethanol.
所述的薄荷脑的水溶性化合物的制备方法，其特征在于所述的步骤3）中渗透膜渗析3～6天。 The preparation method of the water-soluble compound of menthol is characterized in that in the step 3), the permeable membrane is dialyzed for 3-6 days.
所述的薄荷脑的水溶性化合物在日化产品中的应用。 The application of the water-soluble compound of menthol in daily chemical products.
所述的薄荷脑的水溶性化合物在饮料中的应用。 The application of the water-soluble compound of menthol in beverages.
所述的薄荷脑的水溶性化合物在食品中的应用。 The application of the water-soluble compound of menthol in food.
所述的薄荷脑的水溶性化合物在制备抗菌药物中的应用。 The application of the water-soluble compound of menthol in the preparation of antibacterial drugs.
本发明对薄荷脑通过本发明的步骤条件制成薄荷脑的水溶性钠盐或钾盐，改变了薄荷脑不溶于水的特点，得到的产品极易溶于水，为后续的加工带来了方便。另外，本发明开发了薄荷脑的水溶性钠盐或钾盐的新用途。 The present invention makes the water-soluble sodium salt or potassium salt of menthol through the step condition of the present invention to menthol, has changed the characteristic that menthol is insoluble in water, and the product that obtains is very easily soluble in water, has brought for follow-up processing convenient. In addition, the present invention develops a new application of the water-soluble sodium or potassium salt of menthol.
具体实施方式 Detailed ways
以下结合实施例来进一步说明本发明。 The present invention will be further described below in conjunction with the examples.
实施例1：薄荷脑的水溶性钠盐的制备 Embodiment 1: the preparation of the water-soluble sodium salt of menthol
1）氮气气氛下，在反应容器中向薄荷脑的乙醇溶液中加入金属钠，薄荷脑和金属钠的摩尔比为1:1.1，并在温度25℃下进行缓慢搅拌600分钟，充分反应，静置，过夜； 1) Under a nitrogen atmosphere, add metal sodium to the ethanol solution of menthol in a reaction vessel, the molar ratio of menthol and metal sodium is 1:1.1, and slowly stir at a temperature of 25°C for 600 minutes to fully react and statically place overnight;
2）将步骤1）得到的混合物过滤浓缩，乙醇洗涤，干燥，收集固体； 2) Concentrate the mixture obtained in step 1) by filtration, wash with ethanol, dry, and collect the solid;
3）将步骤2）得到的固体溶解于水，再采用渗透膜渗析5天，然后减压除水，得到薄荷脑的水溶性钠盐。 3) Dissolving the solid obtained in step 2) in water, and then using an osmotic membrane for dialysis for 5 days, and then removing water under reduced pressure to obtain a water-soluble sodium salt of menthol.
实施例2：薄荷脑的水溶性钾盐的制备 Embodiment 2: the preparation of the water-soluble potassium salt of menthol
1）氮气气氛下，在反应容器中向薄荷脑的四氢呋喃溶液中加入金属钾，薄荷脑和金属钠的摩尔比为1:1.2，并在温度24℃下进行缓慢搅拌500分钟，充分反应，静置，过夜； 1) Under a nitrogen atmosphere, add metal potassium to the menthol tetrahydrofuran solution in a reaction vessel, the molar ratio of menthol and metal sodium is 1:1.2, and slowly stir at a temperature of 24°C for 500 minutes to fully react and statically place overnight;
2）将步骤1）得到的混合物过滤浓缩，乙醚洗涤，干燥，收集固体； 2) The mixture obtained in step 1) was concentrated by filtration, washed with ether, dried, and the solid was collected;
3）将步骤2）得到的固体溶解于水，再采用渗透膜渗析3天，然后减压除水，得到薄荷脑的水溶性钾盐。 3) Dissolving the solid obtained in step 2) in water, and then using an osmotic membrane for dialysis for 3 days, and then removing water under reduced pressure to obtain a water-soluble potassium salt of menthol.
实施例3：薄荷脑的水溶性钠盐的制备 Embodiment 3: the preparation of the water-soluble sodium salt of menthol
1）氮气气氛下，在薄荷脑的乙醚溶液中加入金属钠，薄荷脑和金属钠的摩尔比为1:1.3，并在温度28℃下进行缓慢搅拌700分钟，充分反应，静置，过夜； 1) Under a nitrogen atmosphere, add metal sodium to the ether solution of menthol, the molar ratio of menthol and metal sodium is 1:1.3, and slowly stir at a temperature of 28°C for 700 minutes, fully react, stand still, overnight;
2）将步骤1）得到的混合物过滤浓缩，乙醚洗涤，干燥，收集固体； 2) The mixture obtained in step 1) was concentrated by filtration, washed with ether, dried, and the solid was collected;
3）将步骤2）得到的固体溶解于水，再采用渗透膜渗析6天，然后减压除水，得到薄荷脑的水溶性钠盐。 3) Dissolving the solid obtained in step 2) in water, and then dialysis with an osmotic membrane for 6 days, and then removing water under reduced pressure to obtain a water-soluble sodium salt of menthol.
试验例1：水溶性比较 Test Example 1: Comparison of Water Solubility
实施例1、2或3得到的薄荷脑的水溶性盐极易溶解于水，每0.001g薄荷脑的水溶性盐能溶解在大于0.5ml小于1ml的纯水中，而原料薄荷脑不溶于水。 The water-soluble salt of menthol obtained in embodiment 1, 2 or 3 is very easily soluble in water, and the water-soluble salt of every 0.001g menthol can be dissolved in pure water greater than 0.5ml and less than 1ml, while raw material menthol is insoluble in water .
试验例2：抗菌抑菌效果测定（将薄荷脑的水溶性钠盐或钾盐溶于蒸馏水中） Test example 2: Determination of antibacterial and antibacterial effect (dissolving the water-soluble sodium salt or potassium salt of menthol in distilled water)
以下具体说明本发明的应用。 The application of the present invention will be specifically described below.
应用例1：眼药水 Application example 1: eye drops
四裂霉素C 0.06%；泊洛沙姆P407 30%；泊洛沙姆P188 11%；卡波姆 0.2%、实施例1、2或3制得的薄荷脑的水溶性盐5%；生理盐水53.74%。 Tetratomycin C 0.06%; Poloxamer P407 30%; Poloxamer P188 11%; Carbomer 0.2%, embodiment 1, 2 or 3 water-soluble salts of menthol obtained in 5%; Physiological Saline 53.74%.
同时，本发明制得的实施例1、2或3制得的薄荷脑的水溶性盐除了应用于眼药水外，还可以应用于制药领域的外敷皮肤药、内服药等，主要起到一个抗菌消炎的作用，生产时只需在现有的原料中加入占总原料0.0001～0.5%的薄荷脑的水溶性盐即可。 Simultaneously, the water-soluble salt of the menthol that the embodiment 1 that the present invention makes, 2 or 3 makes except being applied to eye drops, can also be applied to externally applied skin medicine, oral medicine etc. in pharmaceutical field, mainly play an antibacterial For the anti-inflammatory effect, it is only necessary to add water-soluble salt of menthol accounting for 0.0001% to 0.5% of the total raw materials in the existing raw materials during production.
应用例2：漱口水 Application example 2: Mouthwash
紫苏油2%；实施例1、2或3制得的薄荷脑的水溶性盐5%；乙醇10%；磷酸氢钙无水盐2%；山梨醇1%；木糖醇2%；六氟硅酸铵0.01%；蒸馏水余量。 Perilla oil 2%; Water-soluble salt 5% of menthol made in embodiment 1, 2 or 3; Ethanol 10%; Calcium hydrogen phosphate anhydrous salt 2%; Sorbitol 1%; Xylitol 2%; Ammonium fluorosilicate 0.01%; the remainder in distilled water.
同时，本发明制得的实施例1、2或3制得的薄荷脑的水溶性盐除了应用于漱口水外，还可以应用于日化领域的牙膏、洗衣粉、洗手液、清洁剂、空气清新剂、花露水、香水、洗发水、洗面奶等等，制作时其只需在常规的配方中加入占原料总重量的0.00001～0.5%的薄荷脑的水溶性盐即可，主要起到一个抗菌消炎抑菌的作用。 Simultaneously, the water-soluble salt of menthol that the embodiment 1 that the present invention makes, 2 or 3 makes except being used in mouthwash, can also be used in toothpaste, washing powder, hand sanitizer, cleaning agent, air Freshener, toilet water, perfume, shampoo, facial cleanser, etc., only need to add 0.00001-0.5% of menthol water-soluble salt to the total weight of raw materials in the conventional formula when making it, which mainly plays an antibacterial role. Anti-inflammatory and antibacterial effect.
应用例3：果汁 Application example 3: Juice
果汁99.9%；实施例1、2或3制得的薄荷脑的水溶性盐0.1%。 Fruit juice 99.9%; The water-soluble salt 0.1% of the menthol that embodiment 1,2 or 3 makes.
同时，本发明制得的实施例1、2或3制得的薄荷脑的水溶性盐除了应用于果汁外，还可以应用于饮料领域的矿泉水、碳酸饮料、功能性饮料、乳品饮料等等，制作时其只需在常规的配方中加入占原料总重量的0.00001～0.5%的薄荷脑的水溶性盐即可，主要起到一个抗菌消炎抑菌的作用。 Simultaneously, the water-soluble salt of menthol prepared in Example 1, 2 or 3 of the present invention can also be applied to mineral water, carbonated drinks, functional drinks, dairy drinks, etc. in the field of beverages in addition to fruit juices When making it, it only needs to add 0.00001-0.5% of the water-soluble salt of menthol to the conventional formula, which mainly plays an antibacterial, anti-inflammatory and antibacterial role.
应用例4：面食 Application Example 4: Pasta
面粉中加入占面粉总量0.001%的实施例1、2或3制得的薄荷脑的水溶性盐即可。 Add the water-soluble salt of menthol that accounts for 0.001% of the total amount of flour in the flour and get final product.
同时，本发明制得的实施例1、2或3制得的薄荷脑的水溶性盐除了应用于面食外，还可以应用于食品领域的蛋糕、饼干等等，制作时其只需在常规的配方中加入占原料总重量的0.00001～0.5%的薄荷脑的水溶性盐即可，主要起到一个抗菌消炎抑菌的作用。 Simultaneously, the water-soluble salt of menthol that the embodiment 1 that the present invention makes, 2 or 3 makes except being used in pasta, can also be used in cake, biscuit etc. of food field, it only needs to be in conventional It only needs to add 0.00001-0.5% of water-soluble salt of menthol to the formula, which mainly plays the role of antibacterial, anti-inflammatory and antibacterial.
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