CN110214950A - The preparation method of curcumin water dispersant - Google Patents
The preparation method of curcumin water dispersant Download PDFInfo
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- CN110214950A CN110214950A CN201910479316.6A CN201910479316A CN110214950A CN 110214950 A CN110214950 A CN 110214950A CN 201910479316 A CN201910479316 A CN 201910479316A CN 110214950 A CN110214950 A CN 110214950A
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- curcumin
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- VFLDPWHFBUODDF-FCXRPNKRSA-N curcumin Chemical compound C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-FCXRPNKRSA-N 0.000 title claims abstract description 150
- 229940109262 curcumin Drugs 0.000 title claims abstract description 75
- 235000012754 curcumin Nutrition 0.000 title claims abstract description 75
- 239000004148 curcumin Substances 0.000 title claims abstract description 75
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 title claims abstract description 75
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 78
- 235000019441 ethanol Nutrition 0.000 claims abstract description 32
- 239000007788 liquid Substances 0.000 claims abstract description 30
- 238000001556 precipitation Methods 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 20
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims abstract description 19
- 238000003756 stirring Methods 0.000 claims abstract description 7
- WHGYBXFWUBPSRW-UHFFFAOYSA-N Cycloheptaamylose Natural products O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO WHGYBXFWUBPSRW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000007791 liquid phase Substances 0.000 claims abstract description 3
- 238000001694 spray drying Methods 0.000 claims abstract description 3
- 229920000858 Cyclodextrin Polymers 0.000 claims description 14
- 150000007522 mineralic acids Chemical class 0.000 claims description 14
- 239000001116 FEMA 4028 Substances 0.000 claims description 13
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 13
- 229960004853 betadex Drugs 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229920001353 Dextrin Polymers 0.000 claims description 9
- 239000004375 Dextrin Substances 0.000 claims description 9
- 235000019425 dextrin Nutrition 0.000 claims description 9
- 229960000583 acetic acid Drugs 0.000 claims description 6
- 239000012362 glacial acetic acid Substances 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 5
- 238000003801 milling Methods 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 241000206575 Chondrus crispus Species 0.000 claims description 2
- 229920002907 Guar gum Polymers 0.000 claims description 2
- 229920000881 Modified starch Polymers 0.000 claims description 2
- 239000004368 Modified starch Substances 0.000 claims description 2
- HDSBZMRLPLPFLQ-UHFFFAOYSA-N Propylene glycol alginate Chemical compound OC1C(O)C(OC)OC(C(O)=O)C1OC1C(O)C(O)C(C)C(C(=O)OCC(C)O)O1 HDSBZMRLPLPFLQ-UHFFFAOYSA-N 0.000 claims description 2
- 235000010489 acacia gum Nutrition 0.000 claims description 2
- 239000001785 acacia senegal l. willd gum Substances 0.000 claims description 2
- 239000000420 anogeissus latifolia wall. gum Substances 0.000 claims description 2
- 235000010417 guar gum Nutrition 0.000 claims description 2
- 239000000665 guar gum Substances 0.000 claims description 2
- 229960002154 guar gum Drugs 0.000 claims description 2
- 235000019314 gum ghatti Nutrition 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 235000019426 modified starch Nutrition 0.000 claims description 2
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 claims description 2
- 239000000770 propane-1,2-diol alginate Substances 0.000 claims description 2
- 238000012163 sequencing technique Methods 0.000 claims description 2
- 235000010493 xanthan gum Nutrition 0.000 claims description 2
- 239000000230 xanthan gum Substances 0.000 claims description 2
- 229920001285 xanthan gum Polymers 0.000 claims description 2
- 229940082509 xanthan gum Drugs 0.000 claims description 2
- 239000001202 beta-cyclodextrine Substances 0.000 claims 1
- 239000001814 pectin Substances 0.000 claims 1
- 235000010987 pectin Nutrition 0.000 claims 1
- 229920001277 pectin Polymers 0.000 claims 1
- 239000000243 solution Substances 0.000 description 31
- 244000163122 Curcuma domestica Species 0.000 description 17
- 235000003392 Curcuma domestica Nutrition 0.000 description 16
- 235000003373 curcuma longa Nutrition 0.000 description 16
- 235000013976 turmeric Nutrition 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 12
- 238000013019 agitation Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- UEPVWRDHSPMIAZ-IZTHOABVSA-N (1e,4z,6e)-5-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)hepta-1,4,6-trien-3-one Chemical compound C1=C(O)C(OC)=CC(\C=C\C(\O)=C\C(=O)\C=C\C=2C=CC(O)=CC=2)=C1 UEPVWRDHSPMIAZ-IZTHOABVSA-N 0.000 description 2
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- HJTVQHVGMGKONQ-LUZURFALSA-N Curcumin II Natural products C1=C(O)C(OC)=CC(\C=C\C(=O)CC(=O)\C=C\C=2C=CC(O)=CC=2)=C1 HJTVQHVGMGKONQ-LUZURFALSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- NMRUIRRIQNAQEB-UHFFFAOYSA-N demethoxycurcumin Natural products OC(=CC(C=CC1=CC(=C(C=C1)O)OC)=O)C=CC1=CC=C(C=C1)O NMRUIRRIQNAQEB-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UEPVWRDHSPMIAZ-UHFFFAOYSA-N p-hydroxycinnamoyl feruloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(O)=CC(=O)C=CC=2C=CC(O)=CC=2)=C1 UEPVWRDHSPMIAZ-UHFFFAOYSA-N 0.000 description 2
- 235000014375 Curcuma Nutrition 0.000 description 1
- 240000009138 Curcuma zedoaria Species 0.000 description 1
- 235000003405 Curcuma zedoaria Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000273928 Zingiber officinale Species 0.000 description 1
- 235000006886 Zingiber officinale Nutrition 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000002300 anti-fibrosis Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000001812 curcuma zedoaria berg. rosc. Substances 0.000 description 1
- -1 curcumin chemical compounds Chemical class 0.000 description 1
- 235000019503 curry powder Nutrition 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000008397 ginger Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 235000019509 white turmeric Nutrition 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/015—Inorganic compounds
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/03—Organic compounds
- A23L29/035—Organic compounds containing oxygen as heteroatom
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/231—Pectin; Derivatives thereof
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/238—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin from seeds, e.g. locust bean gum or guar gum
-
- 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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
- A23L29/20—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents
- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/25—Exudates, e.g. gum arabic, gum acacia, gum karaya or tragacanth
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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
- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
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- A23L29/206—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin
- A23L29/256—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of vegetable origin from seaweeds, e.g. alginates, agar or carrageenan
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- A23L29/269—Foods or foodstuffs containing additives; Preparation or treatment thereof containing gelling or thickening agents of microbial origin, e.g. xanthan or dextran
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- 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
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
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- 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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Abstract
The present invention relates to a kind of preparation methods of curcumin water dispersant, the following steps are included: (1): curcumin is added in the ethyl alcohol of heating, stir to obtain A liquid, configure the acid solution that acid content is 10%, obtain B liquid, cycloheptaamylose is added in the water synthermal with A liquid phase and is dissolved, obtains C liquid；(2): dispersing agent being added to the water and dissolves to obtain D liquid；(3): C liquid being added in A liquid and is mixed, E liquid is obtained, E liquid pH to 3.0-3.3 is adjusted with B liquid, obtains mixed system；(4): obtained above-mentioned mixed system is subjected to reduced pressure precipitation；(5): D liquid being added in the curcumin of precipitation, is stirred continuously, uniform system is obtained；(6): above-mentioned uniform system is ground, spray drying to get.Preparation process of the present invention is simple, and after implementation, the water solubility of curcumin is greatly improved, and can keep permanent stable state in water, expand the application range of product.
Description
Technical field
The invention belongs to technical field of health care food, and in particular to a kind of preparation method of curcumin water dispersant.
Background technique
Curcumin is a kind of natural pigment, is to clean the underground rhizome of turmeric, Radix Curcumae, curcuma zedoary etc., is dry, crushing
Afterwards, obtained from the extracting of the organic solvents such as ethyl alcohol, filtering, concentration purification.Curcumin mainly includes three kinds of active constituents: turmeric
Element (C21H20O6, 70%) molecular weight 368 accounts for about, demethoxycurcumin (C20H18O5, molecular weight 338 accounts for about 15%) and double
Demethoxycurcumin (C19H16O4, 10%) molecular weight 308 accounts for about.
Studies have shown that curcumin chemical compounds are natural pigments bright in colour existing for nature, and it has relatively by force
Heat resistance, oxidisability, reducing resistance advantage, curcumin is nontoxic to people and animals, and tinting strength, tinting power is than all synthetic dyestuffs, natural colour
Element is all strong, is lemon yellow, 3~4 times of sunset yellow, is a kind of excellent pigment.It is more long-drawn-out as the history that colorant is eaten
It long, is the traditional raw material of curry powder, salted white etc..Curcumin can be dissolved in ethyl alcohol, propylene glycol, glacial acetic acid etc., but its
But it is difficult to be dissolved in water at normal temperature, therefore limits its application in aqueous product.
Other than good coloring effect, curcumin is mainly derived from traditional Chinese medicine turmeric, and turmeric has breaking blood and promoting the circulation of qi,
The functions such as inducing meastruation to relieve menalgia, curcumin are its main compositions, modern scientific research show curcumin have anticancer, it is anti-inflammatory,
The functions such as anti-oxidant, in addition, there are also liver protection, anti-gastric duodenal ulcer, anti-fibrosis, promotion immunocompetences, suppression for curcumin
System is a kind of natural activity of multiple-effect by various pharmacological actions such as UV light-induced skin mutation, hypoglycemic, nematicidals
Substance.But due to its water-insoluble, by oral administration after, only minimal amount of curcumin can be absorbed by the body, just because of this,
In recent years, more and more scholars, enterprise are conceived to the solubility problem for solving curcumin, and then improve the biology benefit of curcumin
Expenditure.
Summary of the invention
The water-soluble preferably curcumin product of exploitation, so that human body, which need to largely be taken, can just show due effect, if
It can be improved the dissolubility of curcumin in water, the absorbability in human body aqueous environment can also increase therewith, the present invention
People passes through lot of experiments, solves the water solubility problems of curcumin finally, and so as to complete the present invention, the present invention provides
A kind of preparation method of curcumin water dispersant, according to sequencing the following steps are included:
(1) curcumin is added in the ethyl alcohol of heating, stirs to being completely dissolved, obtains A liquid, inorganic acid is added to water
In, it is configured to the acid solution that acid content is 10%, B liquid is obtained, cycloheptaamylose is added in the water synthermal with A liquid phase and is dissolved,
Obtain C liquid；
(2) dispersing agent is added to the water, stirs to being completely dissolved, obtains D liquid；
(3) C liquid is added in A liquid and is mixed, obtain E liquid, adjusted E liquid pH to 3.0-3.3 with B liquid, obtain mixed system；
(4) obtained above-mentioned mixed system is placed in Rotary Evaporators and precipitation is concentrated under reduced pressure, obtained by beta-cyclodextrin packet
The curcumin wrapped up in and be precipitated；
(5) it in the curcumin that the precipitation that D liquid is continuously added step (4) is precipitated, is stirred continuously, obtains uniform system；
(6) above-mentioned uniform system is successively ground, spray drying to get.
The preparation method of curcumin water dispersant according to claim 1, which is characterized in that described in step (1)
The food grade ethyl alcohol that ethyl alcohol is 95%, the temperature of heating are 30-90 DEG C.
In any of the above-described scheme preferably, in step (1), the inorganic acid is that inorganic acid is selected from glacial acetic acid, lemon
One of acid, phosphoric acid, hydrochloric acid.
In any of the above-described scheme preferably, in step (1), the beta-cyclodextrin can be changed to as hydroxy propyl-Beta-ring
One of shape dextrin, modified starch, dextrin.
In any of the above-described scheme preferably, in step (2), the dispersing agent is selected from Arabic gum, ghatti gum, fruit
One of glue, guar gum, carragheen, propylene glycol alginate and xanthan gum or a variety of mixing.
In any of the above-described scheme preferably, in step (4), the process of precipitation is concentrated under reduced pressure up to nothing in whole system
Until ethyl alcohol.
In any of the above-described scheme preferably, in step (5), stirring is until whole system is with mobility together
Only.
In any of the above-described scheme preferably, in step (6), process of lapping carries out in grinder, and grinding revolving speed is
2800~3500r/min, milling time are 6~8h, obtain a kind of 1 μm of partial size < of good ginger color of uniform water dispersible
Plain aqueous products.
Turmeric is traditional Chinese medicine, there is long applicating history in China, equally has the high personal value in other countries,
It is one of the major health food of Okinawa longevity in Japan, in the U.S., carries out pipe using turmeric, curcumin as food additives
Turmeric and Turmeric P.E are included in change constitution/function medicine by reason, Canada, also known as " natural health-care products new drug ", in India,
It is the important herbal medicine of Ayurveda, is curried main component, referred to as solid gold.
Curcumin is the main nutrient composition of turmeric, still, due to the water-insoluble of curcumin, by oral administration after, only pole
A small amount of curcumin can be absorbed by the body, and just because of this, in recent years, more and more scholars, enterprise, which are conceived to, solves turmeric
The solubility problem of element.
Preparation process of the present invention is simple, and after implementation, the water solubility of curcumin is greatly improved, can be
Permanent stable state is kept in water, expands the application range of product.
Detailed description of the invention
Fig. 1 is the solute effect of rear water dispersion curcumin processed by the invention；
Fig. 2 is the solute effect of common curcumin.
Specific embodiment
In order to be further understood that summary of the invention of the invention, the present invention is elaborated below in conjunction with specific embodiment.
Embodiment one
(1) preparation of premixed solution:
A, the ethanol solution of curcumin: 95% food-grade ethanol for measuring 10~100 parts by weight is heated to 30 DEG C, weighs 2
The Turmeric P.E that the turmeric cellulose content of~20 parts by weight is 95%, is added in 95% ethyl alcohol, under agitation until whole
Dissolution, obtains the ethanol solution of curcumin；
B, the preparation of acid solution: by the inorganic acid of 1~10 parts by weight, (inorganic acid is selected from glacial acetic acid, citric acid, phosphoric acid, hydrochloric acid
One of) be added in the water of 10~100 parts by weight, it is configured to the acid solution that acid content is 10%；
C, the preparation of beta-cyclodextrin solution: measuring the water of 80~800 parts by weight and is heated to the ethanol solution with curcumin
Identical temperature, the cycloheptaamylose for weighing 8~80 parts by weight are dissolved in the aqueous solution for wherein obtaining beta-cyclodextrin；
D, the preparation of aqueous dispersant: the water of 10~100 parts by weight is measured, the dispersing agent of 2~20 parts by weight is being stirred
It mixes down and is continuously added in water, until being completely dissolved, obtain the aqueous solution of dispersing agent；
(2) it mixes
Under agitation, the hydrothermal solution of the beta-cyclodextrin of 80~800 parts by weight is added slowly to equipped with 10~
In the hot ethanol solution of the curcumin of 100 parts by weight, until the two mixes completely, a kind of mixed solution is obtained, then with acid
The inorganic acid solution that content is 10%, is adjusted to 3.0~3.3 for the pH of system, and when pH is lower than 5, curcumin is wrapped in β-ring
It solidifies and is precipitated in dextrin；
(3) precipitation: precipitation is concentrated under reduced pressure in the mixed system that will be obtained through above-mentioned steps in Rotary Evaporators, until entire
Until system is without ethyl alcohol；
(4) dilute: by the aqueous solution containing dispersing agent of 10~100 parts by weight be continuously added through precipitation obtain by β-ring
Dextrin wraps up in the curcumin of precipitation, is stirred continuously, until whole system has mobility together；
(5) it grinds: will be ground by the uniform ground machine of system obtained by the above method, grinding revolving speed is 2800r/
Min, milling time 6h obtain a kind of good curcumin aqueous products of 1 μm of partial size < of uniform water dispersible；
(6) be spray-dried: by the resulting curcumin aqueous solution of the above method it is spray-dried after, water dispersion can be obtained
Property good curcumin embed powder product.
Embodiment two
(1) preparation of premixed solution:
A, the ethanol solution of curcumin: 95% food-grade ethanol for measuring 10~100 parts by weight is heated to 60 DEG C, weighs 2
The Turmeric P.E that the turmeric cellulose content of~20 parts by weight is 95%, is added in 95% ethyl alcohol, under agitation until whole
Dissolution, obtains the ethanol solution of curcumin；
B, the preparation of acid solution: by the inorganic acid of 1~10 parts by weight (inorganic acid is selected from glacial acetic acid, citric acid, phosphoric acid, hydrochloric acid)
It is added in the water of 10~100 parts by weight, is configured to the acid solution that acid content is 10%；
C, the preparation of beta-cyclodextrin solution: measuring the water of 80~800 parts by weight and is heated to the ethanol solution with curcumin
Identical temperature, the cycloheptaamylose for weighing 8~80 parts by weight are dissolved in the aqueous solution for wherein obtaining beta-cyclodextrin；
D, the preparation of aqueous dispersant: the water of 10~100 parts by weight is measured, the dispersing agent of 2~20 parts by weight is being stirred
It mixes down and is continuously added in water, until being completely dissolved, obtain the aqueous solution of dispersing agent；
(2) it mixes
Under agitation, the hydrothermal solution of the beta-cyclodextrin of 80~800 parts by weight is added slowly to equipped with 10~
In the hot ethanol solution of the curcumin of 100 parts by weight, until the two mixes completely, a kind of mixed solution is obtained, then with acid
The inorganic acid solution that content is 10%, is adjusted to 3.0~3.3 for the pH of system, and when pH is lower than 5, curcumin is wrapped in β-ring
It solidifies and is precipitated in dextrin；
(3) precipitation: precipitation is concentrated under reduced pressure in the mixed system that will be obtained through above-mentioned steps in Rotary Evaporators, until entire
Until system is without ethyl alcohol；
(4) dilute: by the aqueous solution containing dispersing agent of 10~100 parts by weight be continuously added through precipitation obtain by β-ring
Dextrin wraps up in the curcumin of precipitation, is stirred continuously, until whole system has mobility together；
(5) it grinds: will be ground by the uniform ground machine of system obtained by the above method, grinding revolving speed is 3100r/
Min, milling time 7h obtain a kind of good curcumin aqueous products of 1 μm of partial size < of uniform water dispersible；
(6) be spray-dried: by the resulting curcumin aqueous solution of the above method it is spray-dried after, water dispersion can be obtained
Property good curcumin embed powder product.
Embodiment three
(1) preparation of premixed solution:
A, the ethanol solution of curcumin: 95% food-grade ethanol for measuring 10~100 parts by weight is heated to 90 DEG C, weighs 2
The Turmeric P.E that the turmeric cellulose content of~20 parts by weight is 95%, is added in 95% ethyl alcohol, under agitation until whole
Dissolution, obtains the ethanol solution of curcumin；
B, the preparation of acid solution: by the inorganic acid of 1~10 parts by weight (inorganic acid is selected from glacial acetic acid, citric acid, phosphoric acid, hydrochloric acid)
It is added in the water of 10~100 parts by weight, is configured to the acid solution that acid content is 10%；
C, the preparation of beta-cyclodextrin solution: measuring the water of 80~800 parts by weight and is heated to the ethanol solution with curcumin
Identical temperature, the cycloheptaamylose for weighing 8~80 parts by weight are dissolved in the aqueous solution for wherein obtaining beta-cyclodextrin；
D, the preparation of aqueous dispersant: the water of 10~100 parts by weight is measured, the dispersing agent of 2~20 parts by weight is being stirred
It mixes down and is continuously added in water, until being completely dissolved, obtain the aqueous solution of dispersing agent；
(2) it mixes
Under agitation, the hydrothermal solution of the beta-cyclodextrin of 80~800 parts by weight is added slowly to equipped with 10~
In the hot ethanol solution of the curcumin of 100 parts by weight, until the two mixes completely, a kind of mixed solution is obtained, then with acid
The inorganic acid solution that content is 10%, is adjusted to 3.0~3.3 for the pH of system, and when pH is lower than 5, curcumin is wrapped in β-ring
It solidifies and is precipitated in dextrin；
(3) precipitation: precipitation is concentrated under reduced pressure in the mixed system that will be obtained through above-mentioned steps in Rotary Evaporators, until entire
Until system is without ethyl alcohol；
(4) dilute: by the aqueous solution containing dispersing agent of 10~100 parts by weight be continuously added through precipitation obtain by β-ring
Dextrin wraps up in the curcumin of precipitation, is stirred continuously, until whole system has mobility together；
(5) it grinds: will be ground by the uniform ground machine of system obtained by the above method, grinding revolving speed is 3500r/
Min, milling time 8h obtain a kind of good curcumin aqueous products of 1 μm of partial size < of uniform water dispersible；
(6) be spray-dried: by the resulting curcumin aqueous solution of the above method it is spray-dried after, water dispersion can be obtained
Property good curcumin embed powder product.
As depicted in figs. 1 and 2, the water solubility of curcumin is greatly improved after handling by means of the present invention, can
Permanent stable state is kept in water, expands the application range of product.
It will be apparent to those skilled in the art that the preparation method of kind curcumin water dispersant of the invention includes above-mentioned hair
The summary of the invention and specific embodiment part of bright specification, as space is limited and to keep specification concise without combining these
Each scheme constituted describes one by one.All within the spirits and principles of the present invention, any modification, equivalent substitution and improvement done
Deng should all be included in the protection scope of the present invention.
Claims (8)
1. a kind of preparation method of curcumin water dispersant, according to sequencing the following steps are included:
(1) curcumin is added in the ethyl alcohol of heating, stirs to being completely dissolved, obtains A liquid, inorganic acid is added to the water, match
It is set to the acid solution that acid content is 10%, B liquid is obtained, cycloheptaamylose is added in the water synthermal with A liquid phase and is dissolved, obtain C liquid；
(2) dispersing agent is added to the water, stirs to being completely dissolved, obtains D liquid；
(3) C liquid is added in A liquid and is mixed, obtain E liquid, adjusted E liquid pH to 3.0-3.3 with B liquid, obtain mixed system；
(4) obtained above-mentioned mixed system is placed in Rotary Evaporators and precipitation is concentrated under reduced pressure, obtain by beta-cyclodextrin wrap up and
The curcumin of precipitation；
(5) D liquid is continuously added in the curcumin being precipitated in step (4) through precipitation, is stirred continuously, obtains uniform system；
(6) above-mentioned uniform system is successively ground, spray drying to get.
2. the preparation method of curcumin water dispersant according to claim 1, which is characterized in that in step (1), the second
The food grade ethyl alcohol that alcohol is 95%, the temperature of heating are 30-90 DEG C.
3. the preparation method of curcumin water dispersant according to claim 1, which is characterized in that in step (1), the nothing
Machine acid is that inorganic acid is selected from one of glacial acetic acid, citric acid, phosphoric acid, hydrochloric acid.
4. the preparation method of curcumin water dispersant according to claim 1, which is characterized in that in step (1), the β-
Cyclodextrin can be changed to one of hydroxy propyl-Beta-cyclodextrine, modified starch, dextrin.
5. the preparation method of curcumin water dispersant according to claim 1, which is characterized in that in step (2), described point
Powder is selected from one of Arabic gum, ghatti gum, pectin, guar gum, carragheen, propylene glycol alginate and xanthan gum or more
The mixing of kind.
6. the preparation method of curcumin water dispersant according to claim 1, which is characterized in that in step (4), depressurize dense
The process of contracting precipitation until in whole system without ethyl alcohol until.
7. the preparation method of curcumin water dispersant according to claim 1, which is characterized in that in step (5), stirring is straight
Until whole system has mobility together.
8. the preparation method of curcumin water dispersant according to claim 1, which is characterized in that ground in step (6)
Journey carries out in grinder, and grinding revolving speed is 2800~3500r/min, and milling time is 6~8h, obtains a kind of 1 μm of partial size <
The good curcumin aqueous products of uniform water dispersible.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111758830A (en) * | 2020-07-08 | 2020-10-13 | 天津蚓福生物科技开发有限公司 | Blood fat reducing antioxidant tabletting candy |
| CN112841643A (en) * | 2020-12-31 | 2021-05-28 | 浙江大学 | Method for solubilizing hydrophobic polyphenol by using hydrophilic polyphenol |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101619174A (en) * | 2009-07-31 | 2010-01-06 | 上海师范大学 | Method for preparing curcumin microcapsule |
| CN201657747U (en) * | 2009-12-16 | 2010-12-01 | 烟台开发区绿源生物工程有限公司 | Edible curcumin microcapsule |
| CN103272245A (en) * | 2013-05-25 | 2013-09-04 | 江苏丰园生物技术有限公司 | Curcumin and mixed-cyclodextrin inclusion compound and preparation method thereof |
| US20140228318A1 (en) * | 2010-07-20 | 2014-08-14 | Sanford Research/USD | Curcumin formulations and methods for making such formulations |
| CN104397673A (en) * | 2014-10-23 | 2015-03-11 | 西安莹朴生物科技股份有限公司 | Curcumin microcapsule preparation method |
| CN104873983A (en) * | 2015-05-25 | 2015-09-02 | 福建省力菲克药业有限公司 | Curcumin cyclodextrin clathrate compound and preparation method thereof |
| CN106727316A (en) * | 2017-02-14 | 2017-05-31 | 福州大学 | A kind of curcumin betadex nano-emulsion agent and preparation method thereof |
| CN106943604A (en) * | 2017-05-08 | 2017-07-14 | 广东海洋大学 | A kind of preparation method of curcumin cyclodextrin super molecule inclusion compound |
| CN107028185A (en) * | 2017-03-23 | 2017-08-11 | 上海应用技术大学 | A kind of amylose curcumin inclusion compound and preparation method thereof |
| CN107712543A (en) * | 2017-09-20 | 2018-02-23 | 徐宝军 | A kind of deflocculation curcumin microcapsule, preparation method and applications |
| CN107952077A (en) * | 2017-12-15 | 2018-04-24 | 河南科技大学 | One kind improves the water miscible method of curcumin and application |
| CN109222179A (en) * | 2018-08-02 | 2019-01-18 | 福建农林大学 | A kind of preparation method of curcumin nano microcapsules |
| CN109481689A (en) * | 2018-12-25 | 2019-03-19 | 广州白云山汉方现代药业有限公司 | Water-soluble composition of a kind of enhancing curcumin and preparation method thereof |
-
2019
- 2019-06-04 CN CN201910479316.6A patent/CN110214950A/en active Pending
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101619174A (en) * | 2009-07-31 | 2010-01-06 | 上海师范大学 | Method for preparing curcumin microcapsule |
| CN201657747U (en) * | 2009-12-16 | 2010-12-01 | 烟台开发区绿源生物工程有限公司 | Edible curcumin microcapsule |
| US20140228318A1 (en) * | 2010-07-20 | 2014-08-14 | Sanford Research/USD | Curcumin formulations and methods for making such formulations |
| CN103272245A (en) * | 2013-05-25 | 2013-09-04 | 江苏丰园生物技术有限公司 | Curcumin and mixed-cyclodextrin inclusion compound and preparation method thereof |
| CN104397673A (en) * | 2014-10-23 | 2015-03-11 | 西安莹朴生物科技股份有限公司 | Curcumin microcapsule preparation method |
| CN104873983A (en) * | 2015-05-25 | 2015-09-02 | 福建省力菲克药业有限公司 | Curcumin cyclodextrin clathrate compound and preparation method thereof |
| CN106727316A (en) * | 2017-02-14 | 2017-05-31 | 福州大学 | A kind of curcumin betadex nano-emulsion agent and preparation method thereof |
| CN107028185A (en) * | 2017-03-23 | 2017-08-11 | 上海应用技术大学 | A kind of amylose curcumin inclusion compound and preparation method thereof |
| CN106943604A (en) * | 2017-05-08 | 2017-07-14 | 广东海洋大学 | A kind of preparation method of curcumin cyclodextrin super molecule inclusion compound |
| CN107712543A (en) * | 2017-09-20 | 2018-02-23 | 徐宝军 | A kind of deflocculation curcumin microcapsule, preparation method and applications |
| CN107952077A (en) * | 2017-12-15 | 2018-04-24 | 河南科技大学 | One kind improves the water miscible method of curcumin and application |
| CN109222179A (en) * | 2018-08-02 | 2019-01-18 | 福建农林大学 | A kind of preparation method of curcumin nano microcapsules |
| CN109481689A (en) * | 2018-12-25 | 2019-03-19 | 广州白云山汉方现代药业有限公司 | Water-soluble composition of a kind of enhancing curcumin and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| 何小维等: "《医药用碳水化合物》", 31 January 2016, 中国轻工业出版社 * |
| 陶慧等: ""姜黄素的增溶及稳定性研究"", 《食品发酵与工业》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111758830A (en) * | 2020-07-08 | 2020-10-13 | 天津蚓福生物科技开发有限公司 | Blood fat reducing antioxidant tabletting candy |
| CN111758830B (en) * | 2020-07-08 | 2022-03-29 | 天津蚓福生物科技开发有限公司 | Blood fat reducing antioxidant tabletting candy |
| CN112841643A (en) * | 2020-12-31 | 2021-05-28 | 浙江大学 | Method for solubilizing hydrophobic polyphenol by using hydrophilic polyphenol |
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Application publication date: 20190910 |