CN112798581A - Preparation method of 2-hexenal adsorption color development film - Google Patents
Preparation method of 2-hexenal adsorption color development film Download PDFInfo
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Abstract
The invention provides a preparation method of a 2-hexenal adsorption color development film, which comprises the following steps: (1) dissolving polyvinyl alcohol in deionized water at 75-95 deg.C under stirring, adding ethanol at 45-65 deg.C, and stirring for 2-4h to obtain casting solution. Extracting 5-10ml of casting solution in a clean culture dish by using an injector, and drying to obtain a PVA film; (2) and uniformly stirring methyl red sodium salt, water, methanol and glycerol (the volume ratio of the water to the methanol to the glycerol is 6.25:5.25: 1) to obtain the aldehyde indicator. And dropwise adding an aldehyde indicator on the PVA film and drying to obtain the color developing film. The product prepared by the method has good adsorption color development capability on 2-hexenal, the raw material is a very safe high molecular organic material, and the product has wide application prospect in the fields of food analysis and detection, high molecular chemical industry and the like.
Description
Technical Field
The invention designs a preparation method of a hexenal adsorption color development film, and belongs to the field of food analysis and detection.
Background
Volatile substances are often an important indicator in assessing the quality of food products. Of the odor volatile compounds of many vegetables and fruits (apples, tomatoes, grapes, etc.) during harvest and storage, 2-hexenal contributes significantly to their aroma. 2-hexenal is a common component of plants and is therefore also called leaf aldehyde. In fact, its concentration in all vegetables and fruits is 3-40 ppm. Dierkes found that the quality of olive oil in different qualities and the content of aldehyde substances including Z-3-hexenal and E-2-hexenal in the olive oil are in positive correlation by studying the quality of the olive oil and the detection of volatile components. Zhang Xin et al, which adopts an electronic nose system to evaluate and research the 'Jinxiu yellow peach' fruits with different ripeness degrees, found that the characteristic aroma main components with different ripeness degrees of the peach fruits in the color transition period, the mature period and the complete mature period are 2-hexenal.
At low levels of aldehydes, a pleasant aroma is produced, but beyond a certain level, spoilage of the food is exacerbated, producing an irritating odor. Research shows that aldehydes have toxicity and teratogenicity to biological tissues, can generate strong irritation to ears, noses and throats, and are closely related to the formation of certain diseases, such as heart disease, cancer, arteriosclerosis and the like. Therefore, the detection of the aldehydes in the food not only concerns the safety problem of the food, but also provides a basis for the evaluation of the food quality, and has very important practical application value. At present, the methods for measuring several aldehydes mainly comprise a spectrophotometric method, a gas chromatography-mass spectrometry combined technology (GC-MS), a high performance liquid chromatography-ultraviolet visible detector (HPLC-UV), a liquid chromatography-mass spectrometry (LC-MS), a high performance liquid chromatography-fluorescence detector (HPLC-FLD) and the like. In the reported aldehyde analysis methods, in order to realize high-selectivity and high-sensitivity detection of the aldehydes, complex pretreatment or derivatization steps are generally required to be carried out on samples, so that the analysis process becomes complicated and tedious. Therefore, how to find a simple and accurate aldehyde qualitative and quantitative method is a problem to be solved urgently at present.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides the hexenal adsorption color developing film which is simple to manufacture, convenient and fast to detect and high in cost benefit, so that the on-site screening, monitoring and early warning of the 2-hexenal in the food are realized, a standard curve for detecting the 2-hexenal is manufactured by combining the analysis gray level of image J software, and the quantitative analysis of the 2-hexenal is further realized.
In order to achieve the purpose, the invention adopts the technical scheme that:
a preparation method of a 2-hexenal adsorption color development film comprises the following steps:
(1) preparation of modified PVA film
Dissolving polyvinyl alcohol in deionized water at 75-95 deg.C, cooling to 45-65 deg.C, adding 6-40ml anhydrous alcohol, and magnetically stirring at constant temperature for 2-4 hr. Standing the solution for 2h until no air bubbles exist to obtain membrane casting solution, pumping 4-10 mL of the membrane casting solution to a dry and clean culture dish by using an injector, and drying at 40-50 ℃ under normal pressure.
(2) Preparation of color developing film
Mixing methyl red sodium salt, water and methanol, stirring for 1h, slowly adding glycerol (the volume ratio of the water to the methanol to the glycerol is 6.25:5.25: 1), and uniformly stirring at room temperature by magnetic force to obtain the aldehyde indicator. Dripping 1.0-2.0ml aldehyde indicator on PVA membrane with pipette, and oven drying at temperature less than 60 deg.C to obtain chromogenic membrane material.
The polyvinyl alcohol in the step (1) is PVA1799, the final mass fraction of the polyvinyl alcohol is 5-15%, and the final volume percentage of the ethanol is 10-40%.
The inner diameter of the culture dish in the step (1) is 56 mm.
The volume ratio of the water to the methanol to the glycerol in the step (2) is 6.25:5.25: 1; the final concentration of methyl red sodium salt was 1.2 mM.
In the step (2), the dosage of the aldehyde indicator is 0.057-0.081ml per square centimeter of membrane.
The initial color of the prepared color developing film is yellow.
The adsorption quantity of the chromogenic membrane material to 2-hexenal is measured by software Image J, and the specific measurement method comprises the following steps: adding 50-70 μ L of 2-hexenal standard solution with different concentrations into a slightly larger culture dish bottom tray, placing the culture dish with color development membrane on it, sealing the two culture dishes with each other, and adsorbing and coloring at 45-85 deg.C for 0-60 min. Recording the color before and after the adsorption of the color developing film, and processing and analyzing the color before and after the response of the 2-hexenal by using Image processing software Image J.
The invention provides a color developing film for adsorbing hexenal, which has the following basic principle of response to 2-hexenal: the modified PVA film material has good compatibility to aldehyde indicators and strong adsorption binding capacity to 2-hexenal. The 2- [ 4-dimethylamino) phenylazo ] benzoate anion with two electron donating methyl groups at the para-terminal amino group can delocalize the lone pair of electrons, resulting in an azo tautomer with cationic and anionic groups. The azo proton in the azo tautomer will form a hydrogen bond with oxygen in the carbonyl group or the anionic group of the conjugated aldehyde in the azo complex compound to form a 6-membered chelate ring to improve the excellent stability of the azo complex. Azo complexes containing delocalized positively charged forms cause the color of the indicator to change from yellow to red, forming a visible color change. The concentration of the 2-hexenal is determined by a standard curve, the visual detection of the 2-hexenal is realized, and the result of the color reaction is shown in figure 1.
The invention has the beneficial effects that:
(1) the polyvinyl alcohol PVA is used as a base material of the film, and has the advantages of no toxicity, no harm, oil resistance, wear resistance, good biocompatibility and the like.
(2) The method adopts polyvinyl alcohol as a carrier for indicating carbon dioxide, can well combine volatile 2-hexenal and an indicator compound, adopts the PVA chromogenic membrane synthesized by molecular self-assembly, and has simple synthesis method and low cost.
(3) The hexenal detection technology provided by the invention has the advantages of simplicity and convenience in operation, short detection time, portability of the device and the like, and can realize detection of 2-hexenal in food.
(4) The invention adopts polyvinyl alcohol PVA as a carrier of an indicator, is ingeniously combined with the indication of 2-hexenal concentration and food freshness detection, and consumers can feel the freshness of food more intuitively, thereby having scientificity and convenience
Drawings
FIG. 1 is a color development before and after adsorption of the color development membrane material produced in example 1; yellow before adsorption and red after adsorption.
FIG. 2 is a standard curve prepared by detecting a series of concentrations of 2-hexenal using a prepared chromogenic membrane in example 2 of the present invention;
FIG. 3 is the effect of the adsorption time of the chromogenic membrane material on the adsorption of 2-hexenal in example 3.
Detailed Description
In order to make the invention easier to understand, the following examples will further illustrate the invention, but the scope of the invention is not limited to these examples
Example 1
(1) 5.321 g of polyvinyl alcohol (PVA 179999%, M) were charged at 90 deg.CW= 74885) is dissolved in 40mL deionized water, the temperature is reduced to 50 ℃, 10mL absolute ethyl alcohol is added, and the solution is stirred magnetically for 2h at constant temperature to be dissolved, so as to obtain casting solution. 5mL of the solution is extracted by a 10mL syringe to a dry and clean culture dish and is put into a 45 ℃ oven to be dried into a PVA film.
(2) Accurately weighing 0.0175g of methyl red sodium salt in a mixed solution of 25ml of water and 21ml of methanol, stirring for 1 hour, slowly adding 4ml of glycerol, and magnetically stirring uniformly at room temperature to obtain the aldehyde indicator. 1.6ml of aldehyde indicator is taken by a pipette and dripped on a PVA film and dried to obtain a color developing film. The amount of aldehyde indicator used was 0.08ml per square centimeter of membrane drop.
(3) The resulting color developing film was suspended in 50. mu.L of 89.47 mg/mL 2-hexenal solution with a controlled sensing distance of 0.7cm and adsorbed for color development at 65 ℃ for 30 min at ambient temperature. As a result, as shown in FIG. 1, the color was yellow before the adsorption, and a red stain was generated after the adsorption.
Example 2
This example is presented to illustrate the plotting of a standard curve for the chromogenic membrane detection of 2-hexenal.
Preparing a standard solution to be detected with a concentration gradient containing 2-hexenal, wherein the concentration of the 2-hexenal is 20, 40, 60, 80, 100, 120, 140, 160, 180 and 200mg/ml in sequence. The color developing film of example 1 was suspended in 50. mu.L of the above standard solution to be measured and the sensing distance was controlled to 0.7cm, and the color was developed by adsorption at an ambient temperature of 65 ℃ for 60 min.
Analyzing the color before and after the response of the 2-hexenal by using image J software, and specifically comprising the following steps of: selecting the same measurement area capable of containing all the color development areas, and sequentially measuring the same color development areas before and after adsorption of the culture dish paved with the color development films to obtain the average gray value before and after adsorption of each color development film. And subtracting the average gray value after adsorption from the average gray value before adsorption of the color development film to obtain the average gray value difference. As the concentration of 2-hexenal increased, the average gray value difference gradually increased and thus a standard curve of the average gray value difference with the concentration of 2-hexenal was established, as shown in fig. 2. As can be seen from FIG. 2, the chromogenic membrane shows a good linear relationship in the concentration range of 0-140mg/ml when detecting 2-hexenal, the linear equation is Y = 0.2255+11.25176, and the correlation coefficient is 0.9991. Therefore, the average gray value before and after the adsorption of the color film can be measured by image J software, and the concentration of the 2-hexenal can be accurately quantified.
Example 3
(1) 6.315 g of polyvinyl alcohol (PVA 1799) is dissolved in 45 mL of deionized water at 90 ℃, the temperature is reduced to 50 ℃, 15mL of absolute ethyl alcohol is added, and the solution is magnetically stirred for 2 hours at constant temperature to obtain the casting solution. 5mL of the solution is extracted by a 10mL syringe to a dry and clean culture dish and is put into a 45 ℃ oven to be dried into a PVA film.
(2) Accurately weighing 0.0175g of methyl red sodium salt in a mixed solution of 25ml of water and 21ml of methanol, stirring for 1 hour, slowly adding 4ml of glycerol, and magnetically stirring uniformly at room temperature to obtain the aldehyde indicator. 1.6ml of aldehyde indicator is taken by a pipette and dripped on a PVA film and dried to obtain a color developing film. The amount of aldehyde indicator used was 0.08ml per square centimeter of membrane drop.
(3) The obtained color developing film is suspended to be contained with 50 mu L of 180 mg/mL 2-hexenal solution, the induction distance is controlled to be 0.7cm, and the color is adsorbed and developed for 60min at the ambient temperature of 65 ℃.
The color spots of the color developing film are collected and processed at intervals of time (adsorption time: 0-60min, interval time: 5 min), so as to obtain an adsorption kinetic curve of the color developing film on the 2-hexenal, which shows the change of the adsorption quantity of the color developing film with time, and the result is shown in figure 3. FIG. 3 shows that the adsorption rate of the color developing film increases and then decreases, and the speed increase is larger from 10min to 40 min; the acceleration rate gradually decreases after 40min, when the adsorption time is 50 min, the adsorption capacity of the color development film tends to be saturated and reaches 85.05 mu g/cm2, and simultaneously, the red color spots can be seen by naked eyes to be darker and have larger area, thereby realizing the visual adsorption.
The above description is only a preferred embodiment of the present invention, and all equivalent changes and modifications made in accordance with the claims of the present invention should be covered by the present invention.
Claims (6)
1. A preparation method of a p-hexenal adsorption color development film is characterized by comprising the following steps:
(1) preparation of PVA film
Dissolving polyvinyl alcohol in deionized water at 70-95 deg.C, cooling to 40-65 deg.C, adding 6-40ml ethanol, and magnetically stirring at constant temperature for 2-4 hr; standing the solution for 2h until no bubbles exist, obtaining a membrane casting solution, pumping 4-10 mL of the membrane casting solution to a dry and clean culture dish by using an injector, and drying at 40-50 ℃ under normal pressure;
(2) preparation of color developing film
Mixing and stirring methyl red sodium salt, water and methanol for 1h, slowly adding glycerol, and uniformly stirring at room temperature by magnetic force to obtain an aldehyde indicator; dripping 1.0-2.0ml aldehyde indicator on PVA membrane, and oven drying at temperature less than 60 deg.C to obtain chromogenic membrane material.
2. The method of claim 1, wherein: the polyvinyl alcohol in the step (1) is PVA1799, the final mass fraction of the polyvinyl alcohol is 5-15%, and the final volume percentage of the ethanol is 10-40%.
3. The method of claim 1, wherein: the inner diameter of the culture dish in the step (1) is 56 mm.
4. The method of claim 1, wherein: the volume ratio of the water to the methanol to the glycerol in the step (2) is 6.25:5.25: 1; the final concentration of methyl red sodium salt was 1.2 mM.
5. The method of claim 1, wherein: in the step (2), the dosage of the aldehyde indicator is 0.057-0.081ml per square centimeter of membrane.
6. The method of claim 1, wherein: the initial color of the prepared color developing film is yellow.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113527728A (en) * | 2021-05-26 | 2021-10-22 | 浙江工业大学 | Preparation method of hydrophobic film and application of hydrophobic film in visual detection of freshness of fruits and vegetables |
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| CN1873408A (en) * | 2005-05-30 | 2006-12-06 | 天津市燕化新材料有限公司 | Method for extracting 2 - ethyl hexenal in polyvinyl butyral acetal, and measuring content |
| US20160160157A1 (en) * | 2011-09-06 | 2016-06-09 | The Sun Products Corporation | Solid and liquid textile-treating compositions |
| CN106198419A (en) * | 2016-08-03 | 2016-12-07 | 哈尔滨普凡农牧有限公司 | Detect reagent and the method for α, β unsaturated aldehyde content in oil plant or oils and fats |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1873408A (en) * | 2005-05-30 | 2006-12-06 | 天津市燕化新材料有限公司 | Method for extracting 2 - ethyl hexenal in polyvinyl butyral acetal, and measuring content |
| US20160160157A1 (en) * | 2011-09-06 | 2016-06-09 | The Sun Products Corporation | Solid and liquid textile-treating compositions |
| CN106198419A (en) * | 2016-08-03 | 2016-12-07 | 哈尔滨普凡农牧有限公司 | Detect reagent and the method for α, β unsaturated aldehyde content in oil plant or oils and fats |
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| BETTINA REHBOKC ET AL.: "Different detection systems for the HPLC analysis of oxylipins, by-products of the enzymatic generation of 2E-hexenal", 《CONFERENCE CONTRIBUTION》 * |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113527728A (en) * | 2021-05-26 | 2021-10-22 | 浙江工业大学 | Preparation method of hydrophobic film and application of hydrophobic film in visual detection of freshness of fruits and vegetables |
| CN113527728B (en) * | 2021-05-26 | 2022-06-21 | 浙江工业大学 | Preparation method of hydrophobic film and application of hydrophobic film in visual detection of freshness of fruits and vegetables |
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