CN106579333A - Alpha-cyclodextrin-sorbic acid inclusion compound and preparation method thereof - Google Patents
Alpha-cyclodextrin-sorbic acid inclusion compound and preparation method thereof Download PDFInfo
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- CN106579333A CN106579333A CN201710014714.1A CN201710014714A CN106579333A CN 106579333 A CN106579333 A CN 106579333A CN 201710014714 A CN201710014714 A CN 201710014714A CN 106579333 A CN106579333 A CN 106579333A
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- Prior art keywords
- cyclodextrin
- sorbic acid
- alpha
- inclusion compound
- inclusion
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- 239000004334 sorbic acid Substances 0.000 title claims abstract description 63
- 229940075582 sorbic acid Drugs 0.000 title claims abstract description 59
- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-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)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 HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims abstract description 36
- 235000010199 sorbic acid Nutrition 0.000 claims abstract description 36
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims abstract description 30
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims abstract description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 239000013078 crystal Substances 0.000 claims abstract description 6
- 239000008367 deionised water Substances 0.000 claims abstract description 5
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 5
- 241000220324 Pyrus Species 0.000 claims description 3
- 235000021017 pears Nutrition 0.000 claims description 3
- 235000021050 feed intake Nutrition 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000000935 solvent evaporation Methods 0.000 claims 2
- 238000002474 experimental method Methods 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 235000013305 food Nutrition 0.000 abstract description 11
- 230000002209 hydrophobic effect Effects 0.000 abstract description 5
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(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 HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 abstract description 5
- 230000008859 change Effects 0.000 abstract description 2
- 238000002156 mixing Methods 0.000 abstract description 2
- 239000003242 anti bacterial agent Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 1
- 238000009210 therapy by ultrasound Methods 0.000 abstract 1
- 230000000694 effects Effects 0.000 description 6
- 239000000022 bacteriostatic agent Substances 0.000 description 5
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 244000005700 microbiome Species 0.000 description 3
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical class C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 3
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- 239000006069 physical mixture Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 230000007928 solubilization Effects 0.000 description 2
- 238000005063 solubilization Methods 0.000 description 2
- 230000003381 solubilizing effect Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- 238000002604 ultrasonography Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 description 1
- WSWCOQWTEOXDQX-UHFFFAOYSA-N 2,4-Hexadienoic acid Chemical class CC=CC=CC(O)=O WSWCOQWTEOXDQX-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000005909 ethyl alcohol group Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229940075554 sorbate Drugs 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- 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
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The invention relates to an alpha-cyclodextrin-sorbic acid inclusion compound and a preparation method thereof. The inclusion compound contains alpha-cyclodextrin and sorbic acid according to an inclusion ratio of 1:1. The preparation method comprises the following steps: 1, feeding alpha-cyclodextrin and sorbic acid according to a molar ratio of 1:2.2, and respectively dissolving the alpha-cyclodextrin and sorbic acid in deionized water and anhydrous ethanol; 2, mixing and heating above two solutions, and carrying out ultrasonic treatment to realize complete reaction; and 3, placing the obtained reaction solution in a shady place, volatilizing a solvent in a natural state to obtain alpha-cyclodextrin-sorbic acid inclusion compound crystals. The hydrophobic cavity of cyclodextrin can include organic molecules, and the hydrophobic property of the outer cavity makes the generated inclusion compound dissolved in water in order to change the relevant properties of the organic molecules. Sorbic acid is a fat-soluble food antibacterial agent, and difficultly plays a role in a water phase. The hydrophobic chain of the sorbic acid is included in the inner cavity of cyclodextrin in order to form the stable inclusion compound, so the water solubility is improved, and a novel food antibacterial agent with good performances is developed.
Description
Technical field
The invention belongs to food additives synthesis technical field, and in particular to a kind of alpha-cyclodextrin-sorbic acid inclusion compound, this
Invention also discloses a kind of preparation method of alpha-cyclodextrin-sorbic acid inclusion compound.
Background technology
Sorbic acid（2,4 1 hexadienoic acids）It is a kind of fat-soluble weak organic acid, as generally acknowledged a kind of efficient, low toxicity, peace
Complete a kind of fat-soluble food bacteriostatic agent, the activity of energy inhibitory enzyme, causes the collapse of the vital movement of microorganism, so sorb
Acid is that have stronger bacteriostatic activity.But, in food system, microorganism is only occurred in water phase, and bacteriostatic agent must divide
Dissipate to be entered in thalline in water and play a role.Solubility in water phase enters the direct phase of ability of thalline with bacteriostatic agent
Close, and the ageing solubility then based on antiseptic of antibacterial.Thus bacteriostatic agent must possess good water solubility, this is so as to suppressing
Application of the sorbic acid of water-soluble relative mistake in field of food.
Cyclodextrin molecular has the hydrophilic property of inner chamber hydrophobic external surface, guest molecule Jing after cyclodextrin encapsulated, solubility
Increase, stability are improved, bioavilability is dramatically increased, while excitant, toxicity, side effect reduction.Alpha-cyclodextrin itself has
There is higher water solubility, the solubility of medicine is remarkably improved after including, meanwhile, metabolism is very in alpha-cyclodextrin body
Slowly, it is best to the slow release effect of institute's inclusion drug molecule so that it can form bag with numerous all kinds of hydrophobic guest molecules
Compound, and then cause the physics and chemical property of these guest molecules to change, therefore it is widely used in many fields.
In food industry, cyclodextrin is mainly used in the labile element in stabilizing food, removes stink and bitter taste in food；Cause
This, alpha-cyclodextrin is increasingly favored in field of food.
In view of alpha-cyclodextrin solubility is big, and its cavity can include numerous guest molecules and form inclusion compound, Jin Ergai
The characteristics of becoming guest molecule correlation physicochemical property, the present invention modifies sorbic acid using alpha-cyclodextrin inclusion technique, forms stable
Alpha-cyclodextrin-sorbic acid inclusion compound, be expected to solve some outstanding problems for existing as food additives of sorbic acid.The inclusion
Thing can will steadily in the long term be stored and use with good aqueous solubility.Therefore, the alpha-cyclodextrin that prepared by the present invention-sorbic acid inclusion
Thing, not only remaining guest molecule sorbic acid can suppress growth of microorganism, the rotten characteristic of prevent food spoilage, also evade it
Poorly water-soluble feature, but also the functions such as the identification inclusion of host molecule alpha-cyclodextrin have been given full play to, preferably project sorb
The performance such as antibacterial, fresh-keeping of acid, to develop New-type wide-spectrum, efficient and economical and practical food bacteriostatic agent new way is provided.
The content of the invention
The technical problem to be solved is, for sorbic acid water-soluble is poor, the characteristic such as property is active, there is provided one
Sorbic acid inclusion compound is planted, solubility is improved in water phase, and stability is improved.
The present invention provides a kind of alpha-cyclodextrin-sorbic acid inclusion compound, includes alpha-cyclodextrin-sorbic acid, wherein Inclusion ratio
For 1:1.
The present invention provides a kind of preparation process of above-mentioned alpha-cyclodextrin-sorbic acid inclusion compound, comprises the following steps.
（1）According to mol ratio nAlpha-cyclodextrin: nSorbic acid=1:2.2 feed intake, and it is dissolved in respectively deionized water and absolute ethyl alcohol
In.
（2）Reaction temperature condition of the present invention is that a kind of alpha-cyclodextrin-sorbic acid inclusion compound is warm according to reaction
Degree condition is 60oC。
（3）Reaction time condition of the present invention is, a kind of alpha-cyclodextrin-sorbic acid inclusion compound, according to during reaction
Between condition be 70 min.
（4）0.9728 g is dissolved in 40 mL deionized waters（0.001 mol）Alpha-cyclodextrin, separately in the anhydrous second of 2.0 mL
0.2467 g is dissolved in alcohol（0.0022 mol）Sorbic acid, 60oThis sorbic acid ethanol solution is slowly added dropwise under C ultrasound conditions
To in the alpha-cyclodextrin aqueous solution, continue ultrasonic 70 min, after the completion of question response, reaction solution is moved to into shady place, volatilize naturally
After 72 h, crystal is separated out.Suction filtration, 60 with a small amount of deionized water and washes of absolute alcohol for several timeso3 h are vacuum dried under C, are obtained
White powder inclusion compound.
（5）It is of the invention to be to the determination methods that Inclusion ratio is adopted, a kind of alpha-cyclodextrin-mountain based on ultraviolet visible spectrometry
The Inclusion ratio criterion of pears acid inclusion compound.The standard concentration curve of sorbic acid is drawn initially with ultraviolet visible spectrometry, further according to
Absorbance calculates sorbic acid contained in inclusion compound（nSorbic acid）, while calculating the content of alpha-cyclodextrin（nAlpha-cyclodextrin）So as to
Calculate Inclusion ratio, Inclusion ratio nSorbic acid/nAlpha-cyclodextrinFor 1.
（4）The present invention is to the determination methods that solubilizing effect is adopted, a kind of alpha-cyclodextrin based on ultraviolet visible spectrometry-
The solubilizing effect criterion of sorbic acid inclusion compound.The standard concentration curve of sorbic acid is drawn initially with ultraviolet visible spectrometry, will
After the alpha-cyclodextrin solution of variable concentrations is sufficiently mixed with sorbic acid, mountain contained in solution is obtained according to the absorbance of measurement
Pears acid（S）, sorbic acid intrinsic solubility in aqueous under contrast similarity condition（So=0.017×10-5mol/L）, so as to
Calculate solubilization factor（S/So）.
Present method invention prepares alpha-cyclodextrin-sorbic acid inclusion compound, and the inclusion compound has and is obviously improved dissolubility, so as to carry
The high bioavailability of sorbic acid.
Description of the drawings
The description of the drawings of the present invention is as follows.
Fig. 1 is alpha-cyclodextrin infrared spectrogram.
Fig. 2 is sorbic acid infrared spectrogram.
Fig. 3 is alpha-cyclodextrin and sorbic acid physical mixture and alpha-cyclodextrin-sorbic acid inclusion compound infrared spectrum.
Specific embodiment
With reference to specific embodiment, the present invention is described in detail.
The preparation of 1 alpha-cyclodextrin of embodiment-sorbic acid inclusion compound
0.9728 g is dissolved in 40 mL deionized waters（0.001 mol）Alpha-cyclodextrin, separately dissolves in 2.0 mL absolute ethyl alcohols
0.2467 g（0.0022 mol）Sorbic acid, 60oThis sorbic acid ethanol solution is slowly dropped to into α-ring paste under C ultrasound conditions
In the smart aqueous solution, continue ultrasonic 70 min, after the completion of question response, reaction solution is moved to into shady place, after 72 h that volatilize naturally, analysis
Go out crystal.Suction filtration, 60 with a small amount of deionized water and washes of absolute alcohol for several timeso3 h are vacuum dried under C, white powder is obtained
Shape inclusion compound.
The Inclusion ratio of 2 alpha-cyclodextrins of embodiment-sorbic acid inclusion compound is calculated
Alpha-cyclodextrin-sorbic acid inclusion compound that certain mass is implemented to be prepared in 1 is weighed, using ultraviolet visible spectrometry as inclusion
Than the criterion for calculating.Concrete operations are as follows, and in certain wave strong point absorbance is measured, and calculated according to standard concentration curve, obtain
Determination of sorbic in inclusion compound, and then the content of alpha-cyclodextrin in inclusion compound is obtained, so as to calculate alpha-cyclodextrin-sorbic acid bag
The Host-guest ratio of compound is 1:1.
Solubilized effect of the alpha-cyclodextrin of embodiment 3 to sorbic acid
Precise α-CD, are configured to concentration and are respectively 0,5,10,15,20 and 25 mmol/L α-CD solution, take above-mentioned solution
Each 10 mL, plus the sorbic acid of certain mass, ultrasonic 30 min dissolvings are complete, after solid-liquid reaches balance, place one week, filter,
In maximum absorption wave strong point mensuration absorbance.Solubilising effect of the sorbic acid in α-CD solution is determined using ultraviolet visible spectrometry
Should, the results are shown in Table 1.With the increase of α-CD concentration, the solubility of sorbate molecule increases, and illustrates that α-CD have to sorbic acid good
Good solubilization.
The solubilized effect of the alpha-cyclodextrin of table 1
| α-CD（10-3mol/L） | 0 | 5 | 10 | 15 | 20 | 25 |
| S（10-5mol/L）(a) | 0.017(b) | 0.056 | 0.105 | 0.134 | 0.175 | 0.219 |
| S/So (c) | - | 3.29 | 6.18 | 7.88 | 10.3 | 12.9 |
(a) S：Concentration of the sorbic acid in α-CD；(b) So：Saturation solubility of the sorbic acid in water；(c) S/So：Solubilising
The factor.
Knowable to infrared spectrogram, first, the collection of illustrative plates of alpha-cyclodextrin-sorbic acid inclusion compound（Fig. 3 b）With alpha-cyclodextrin spectrum
Figure（Fig. 1）Or the collection of illustrative plates of sorbic acid（Fig. 2）Compare, while absworption peak increased, position also there occurs movement；Secondly include
Thing collection of illustrative plates and alpha-cyclodextrin and the physical mixture of sorbic acid（Fig. 3 a）Also have significantly different, illustrate using of the present invention
Method, is not that the simple physical mixing of the two occurs using raw material alpha-cyclodextrin and sorbic acid, but by sorbic acid inclusion α-
Cyclodextrin inner chamber forms stable inclusion compound.
Claims (5)
1. a kind of alpha-cyclodextrin-sorbic acid inclusion compound, it is characterised in that containing alpha-cyclodextrin and sorbic acid, alpha-cyclodextrin and mountain
The Inclusion ratio of pears acid is 1:1.
2. the preparation method of alpha-cyclodextrin as claimed in claim 1-sorbic acid inclusion compound, it is characterised in that including following step
Suddenly：
According to mol ratio nAlpha-cyclodextrin: nSorbic acid=1:2.2 feed intake, and it is dissolved in respectively absolute ethyl alcohol and deionized water；
Blend step（1）The two kinds of solution for obtaining, carry out inclusion experiment, and inclusion process is using heating ultrasonic method；
By step（2）The mixed solution for obtaining, obtains under inclusion compound crystal, i.e. nature, to mix using solvent evaporation method
Solution left standstill for a period of time after, have alpha-cyclodextrin-sorbic acid inclusion compound crystal to separate out in solution.
3. preparation method according to claim 2, it is characterised in that step（1）Employed in organic solvent for anhydrous
Ethanol.
4. preparation method according to claim 2, is characterised by, step（2）In ultrasonic method, the inclusion reaction time be 70
Min, reaction temperature is 60oC。
5. preparation method according to claim 2, is characterised by, step（3）The solvent evaporation method of middle employing, is to react
Solution afterwards moves to shady place, after 72 h that volatilize naturally, separates out crystal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710014714.1A CN106579333A (en) | 2017-01-10 | 2017-01-10 | Alpha-cyclodextrin-sorbic acid inclusion compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710014714.1A CN106579333A (en) | 2017-01-10 | 2017-01-10 | Alpha-cyclodextrin-sorbic acid inclusion compound and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106579333A true CN106579333A (en) | 2017-04-26 |
Family
ID=58583021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710014714.1A Pending CN106579333A (en) | 2017-01-10 | 2017-01-10 | Alpha-cyclodextrin-sorbic acid inclusion compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101223183A (en) * | 2005-06-13 | 2008-07-16 | 嘉吉公司 | Cyclodextrin inclusion complexes and methods of preparing same |
-
2017
- 2017-01-10 CN CN201710014714.1A patent/CN106579333A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101223183A (en) * | 2005-06-13 | 2008-07-16 | 嘉吉公司 | Cyclodextrin inclusion complexes and methods of preparing same |
Non-Patent Citations (2)
| Title |
|---|
| 方亮: "药剂学（第3版）", 《药剂学（第3版）》 * |
| 李学红: "环糊精在抗菌食品包装中的基础应用研究", 《中国博士学位论文全文数据库 工程科技I辑》 * |
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