CN106666327A - Gamma-cyclodextrin-sorbate compound and preparation method thereof - Google Patents
Gamma-cyclodextrin-sorbate compound and preparation method thereof Download PDFInfo
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- CN106666327A CN106666327A CN201710014709.0A CN201710014709A CN106666327A CN 106666327 A CN106666327 A CN 106666327A CN 201710014709 A CN201710014709 A CN 201710014709A CN 106666327 A CN106666327 A CN 106666327A
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- cyclodextrin
- gamma
- sorbic acid
- clathrate
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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
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3481—Organic compounds containing oxygen
- A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
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- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention discloses a gamma-cyclodextrin-sorbate compound and a preparation method thereof. The compound contains gamma-cyclodextrin and sorbic acid in the formation ratio of 1:1. The method comprises the preparation steps of (1) feeding the gamma-cyclodextrin and n sorbic acid in the molar ratio of 1:2.2 and dissolving gamma-cyclodextrin and n sorbic acid into deionized water and absolute ethyl alcohol separately; (2) mixing and heating the two solutions, and carrying out ultrasonic treatment for complete reaction; and (3) putting a reaction solution in a shade place and volatilizing the solvent in a natural state to obtain gamma-cyclodextrin-sorbate compound crystal. Cyclodextrin has a hydrophobic cavity and is coated with an organic active ingredient to play a role in stabilizing an organic matter. Sorbic acid is an organic antibacterial agent, and has the disadvantages of being awful in smell, relatively poor in water solubility and easy to oxidize and discolor. According to the prepared stable gamma-cyclodextrin-sorbate compound, the stability of sorbic acid is obviously improved, the solubility is improved, the pungent smell is covered and a better application prospect is developed for the antibacterial agent.
Description
Technical field
The invention belongs to food additive synthesis technical field, and in particular to a kind of gamma-cyclodextrin-sorbic acid clathrate,
The invention also discloses the preparation method of this clathrate.
Background technology
Sorbic acid（2,4 1 hexadienoic acids）It is weak-type antibacterial, has significantly suppression to mycete, yeast and aerobe
Effect, toxicity are weaker, and sorbic acid is widely used in the newborn class of milk product, various bread snack food products, beverage, tune, meat, water producing system
In the middle of the food industry such as product.But the bacteriostasis of sorbic acid are easily affected by pH values, only in non-dissociated molecularity
Bacteriostasis are played, and due to containing active carboxyl and hydrophobic conjugated double bond in its molecule, chemical property also less stable,
These drawbacks limit its further extensively apply.
In view of gamma-cyclodextrin is nontoxic, tasteless, and the special annular stereochemical structure with " hydrophilic outward, interior hydrophobic ", cyclodextrin was both
Also guest molecule can be included to form clathrate with its hydrophobic cavity in the solid state in aqueous, so as to cause
The change of the properties such as the physics of guest molecule, chemistry, biology, the present invention modify Pyrusussuriensiss using gamma-cyclodextrin inclusion technique
Acid, forms stable gamma-cyclodextrin-sorbic acid clathrate, is expected to solution sorbic acid and dashes forward as some that food preservative is present
Go wrong.The clathrate can will be stored and be used with good aqueous solubility steadily in the long term.Therefore, the γ that prepared by the present invention-ring paste
Essence-sorbic acid clathrate, not only remains the intrinsic advantages of guest molecule sorbic acid, improves its defect, but also imparts master
The functions such as the identification inclusion of body molecule gamma-cyclodextrin, can play improves food technology and quality, preferably plays sorbic acid
The performance such as antibacterial, fresh-keeping, is expected to open up the application new way of sorbic acid antibacterial in field of food industry.
The content of the invention
The technical problem to be solved is, for active, strong, poorly water-soluble of Odor stimulation of Pyrusussuriensiss Acidity etc.
A kind of problem, there is provided gamma-cyclodextrin-sorbic acid clathrate so that the stability of sorbic acid, water solublity are improved, zest
Abnormal smells from the patient is covered.
The present invention provides a kind of gamma-cyclodextrin-sorbic acid clathrate, includes gamma-cyclodextrin and sorbic acid, wherein inclusion
Than for 1:1.
The present invention provides a kind of preparation method of above-mentioned gamma-cyclodextrin-sorbic acid clathrate, comprises the following steps.
（1）According to mol ratio nGamma-cyclodextrin: nSorbic acid=1:2.2 feed intake, and which is dissolved in deionized water and ethanol respectively.
（2）60oThis sorbic acid ethanol solution is slowly dropped in gamma-cyclodextrin aqueous solution under C ultrasound conditions, is continued
Reaction solution, after the completion of question response, is moved to shady place by 70 min of ultrasound, after 72 h that volatilize naturally, separates out crystal.Sucking filtration, uses
A small amount of deionized water and washes of absolute alcohol for several times, 60o3 h are vacuum dried under C, white powder clathrate is obtained.
（3）The present invention using the determination methods of Inclusion ratio is, a kind of gamma-cyclodextrin-mountain based on ultraviolet visible spectrometry
The Inclusion ratio criterion of pears acid clathrate.The standard concentration curve of sorbic acid is drawn initially with ultraviolet visible spectrometry, is accurately claimed
The clathrate of certain mass is taken, its absorbance is measured in certain wave strong point, substitute into standard concentration curve equation, obtain clathrate
The content of middle sorbic acid（nSorbic acid）, while calculating the content of gamma-cyclodextrin（nGamma-cyclodextrin）, Inclusion ratio is calculated for 1:1（Inclusion
Than=nSorbic acid/nGamma-cyclodextrin）.
（4）The present invention is that a kind of γ-ring based on ultraviolet visible spectrometry is pasted to the determination methods that solubilizing effect is adopted
The solubilizing effect criterion of essence-sorbic acid clathrate.The standard concentration curve of sorbic acid is drawn initially with ultraviolet visible spectrometry,
After the gamma-cyclodextrin solution of variable concentrations and sorbic acid are sufficiently mixed, institute in solution obtained according to the absorbance of measurement
The sorbic acid for containing（S）, contrast intrinsic solubility of the sorbic acid in aqueous solution under similarity condition（S0=0.017×10-5 mol/L）,
So as to calculate solubilization factor（S/S0）.
Present method invention prepares gamma-cyclodextrin-sorbic acid clathrate, and the clathrate is improved with water solublity is obviously improved
Stability, covers penetrating odor so that sorbic acid biocompatibility strengthens, and improves the bioavailability of sorbic acid.
Description of the drawings
The description of the drawings of the present invention is as follows：
Fig. 1 is gamma-cyclodextrin infrared spectrogram；
Fig. 2 is sorbic acid infrared spectrogram；
Fig. 3 is gamma-cyclodextrin and sorbic acid physical mixture and gamma-cyclodextrin-sorbic acid clathrate infared spectrum.
Specific embodiment
With reference to specific embodiment, the present invention is described in detail.
1 gamma-cyclodextrin of embodiment-sorbic acid clathrate
1.2971 g are dissolved in 40 mL deionized waters（0.001 mol）Gamma-cyclodextrin, it is separately molten in 2.0 mL dehydrated alcohol
Solve 0.2467 g（0.0022 mol）Sorbic acid, 60oUnder C ultrasound conditions by the ethanol solution of this sorbic acid be slowly dropped to γ-
In the aqueous solution of cyclodextrin, continue ultrasonic 70 min, after the completion of question response, reaction solution is moved to into shady place, naturally volatilization 72
After h, crystal is separated out.Sucking filtration, 60 with a small amount of deionized water and washes of absolute alcohol for several timeso3 h are vacuum dried under C, obtain white
Color powder clathrate.
The Inclusion ratio of 2 gamma-cyclodextrins of embodiment-sorbic acid clathrate is calculated
Gamma-cyclodextrin-sorbic acid clathrate that certain mass is implemented to prepare in 1 is weighed, using ultraviolet visible spectrometry as bag
Criterion of the knot than calculating.Concrete operations are as follows, measure absorbance in certain wave strong point, calculated according to standard concentration curve, obtained
The Determination of sorbic in clathrate, and then the content of gamma-cyclodextrin in clathrate is obtained, so as to calculate gamma-cyclodextrin-Pyrusussuriensiss
The Host-guest ratio of sour clathrate is 1:1.
The solubilized effect of the p- sorbic acid of 3 gamma-cyclodextrin of embodiment
Precise gamma-cyclodextrin, is configured to concentration and is respectively 0,5,10,15,20 and 25 mmol/L gamma-cyclodextrin solution,
Each 10 mL of above-mentioned solution, plus the sorbic acid of certain mass are taken, ultrasonic 30 min dissolvings are complete, after solid-liquid reaches balance, place
One week, filter, in maximum absorption wave strong point mensuration absorbance.1 is the results are shown in Table, sorbic acid is determined using ultraviolet visible spectrometry and is existed
Solubilized effect in gamma-cyclodextrin solution, with the increase of gamma-cyclodextrin concentration, the dissolubility of sorbate molecule increases, explanation
Gamma-cyclodextrin has good solubilization to sorbic acid
The solubilized effect of 1 gamma-cyclodextrin of table
| γ-CD（10-3mol/L） | 0 | 5 | 10 | 15 | 20 | 25 |
| S（10-5mol/L） | 0.017 | 0.053 | 0.093 | 0.155 | 0.187 | 0.231 |
| S/So | - | 2.12 | 4.89 | 6.53 | 8.53 | 10.5 |
S：Concentration of the sorbic acid in γ-CD；So：Saturation solubility of the sorbic acid in water, herein S0=0.017×10-5
mol/L；S/So：Solubilization factor.
Knowable to infrared spectrum, gamma-cyclodextrin-sorbic acid clathrate first（Fig. 3 b）With gamma-cyclodextrin spectrogram（Fig. 1）
Or the collection of illustrative plates of sorbic acid（Fig. 2）Compare, while absworption peak increased, position also there occurs movement；Secondly its clathrate with
The physical mixture of gamma-cyclodextrin and sorbic acid（Fig. 3 a）Also have significantly different, illustrate method of the present invention, using simultaneously
It is not the physical mixed that gamma-cyclodextrin and sorbic acid occur, but sorbic acid inclusion forms stable bag in gamma-cyclodextrin inner chamber
Compound.
Claims (5)
1. a kind of gamma-cyclodextrin-sorbic acid clathrate, it is characterised in that containing gamma-cyclodextrin and sorbic acid, and gamma-cyclodextrin
Inclusion ratio with sorbic acid is 1:1.
2. the preparation method of gamma-cyclodextrin as claimed in claim 1-sorbic acid clathrate, it is characterised in that including following step
Suddenly：
According to mol ratio nGamma-cyclodextrin: nSorbic acid=1:2.2 feed intake, and which is dissolved in deionized water and dehydrated alcohol respectively；
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）Mixed solution, clathrate crystal is obtained using solvent evaporation method.
3. preparation method according to claim 2 is characterized in that, step（1）Employed in organic solvent be anhydrous second
Alcohol.
4. preparation method according to claim 2, is characterised by, step（2）In ultrasonic method, the inclusion reaction time be 70
Min, reaction temperature are 60oC。
5. preparation method according to claim 2, it is characterised in that step（3）In solvent evaporation method refer to solvent from
So volatilize, clathrate crystal is separated out.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201710014709.0A CN106666327A (en) | 2017-01-10 | 2017-01-10 | Gamma-cyclodextrin-sorbate compound and preparation method thereof |
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| CN201710014709.0A CN106666327A (en) | 2017-01-10 | 2017-01-10 | Gamma-cyclodextrin-sorbate compound and preparation method thereof |
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| CN201710014709.0A Pending CN106666327A (en) | 2017-01-10 | 2017-01-10 | Gamma-cyclodextrin-sorbate compound and preparation method thereof |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102210673A (en) * | 2010-04-07 | 2011-10-12 | 上海港太药业发展有限公司 | Cyclodextrin inclusion compound containing ligustilide, and preparation method thereof |
| CN103284111A (en) * | 2013-05-25 | 2013-09-11 | 江苏丰园生物技术有限公司 | Mustard essential oil and mixed cyclodextrin inclusion compound and preparation method thereof |
-
2017
- 2017-01-10 CN CN201710014709.0A patent/CN106666327A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102210673A (en) * | 2010-04-07 | 2011-10-12 | 上海港太药业发展有限公司 | Cyclodextrin inclusion compound containing ligustilide, and preparation method thereof |
| CN103284111A (en) * | 2013-05-25 | 2013-09-11 | 江苏丰园生物技术有限公司 | Mustard essential oil and mixed cyclodextrin inclusion compound and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 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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