CN110584045A - Method for inhibiting hydrogen sulfide generation in hot pickled mustard tuber production - Google Patents

Method for inhibiting hydrogen sulfide generation in hot pickled mustard tuber production Download PDF

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Publication number
CN110584045A
CN110584045A CN201911042845.6A CN201911042845A CN110584045A CN 110584045 A CN110584045 A CN 110584045A CN 201911042845 A CN201911042845 A CN 201911042845A CN 110584045 A CN110584045 A CN 110584045A
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hydrogen sulfide
solution
inhibitor
preserved szechuan
szechuan pickle
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邓利民
蒯念生
候映天
苟绍华
张勤
郑彩英
代小明
陈丽丽
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Sichuan Anke Technology Consulting Co Ltd
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Sichuan Anke Technology Consulting Co Ltd
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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
    • A23L19/00—Products from fruits or vegetables; Preparation or treatment thereof
    • A23L19/20—Products from fruits or vegetables; Preparation or treatment thereof by pickling, e.g. sauerkraut or pickles
    • 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
    • A23L29/03—Organic compounds
    • A23L29/045—Organic compounds containing nitrogen as heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/90—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in food processing or handling, e.g. food conservation

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  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Storage Of Fruits Or Vegetables (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)

Abstract

The invention relates to a method for inhibiting hydrogen sulfide generation in tuber mustard production, which comprises the following steps: s1, cleaning fresh green head vegetables to be used as a raw material of hot pickled mustard tuber; s2, putting the cleaned preserved szechuan pickle raw materials into a pickle tank, adding salt for pickling for 2-3 days to obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% of hydrogen sulfide inhibitor during pickling; s3, fishing out the pickled mustard tuber semi-finished product, and washing with water for desalting; s4, adding 0.1-0.2% of hydrogen sulfide inhibitor into the desalted preserved szechuan pickle, mixing uniformly, putting into a plastic film bag, vacuumizing for storage, and sealing and fermenting at a set temperature for 10 days to obtain a finished preserved szechuan pickle; during the fermentation process, the tuber mustard in partial fermentation is selected for testing, and the hydrogen sulfide production amount is judged. The invention can reduce the generation amount of hydrogen sulfide, ensure the food safety of the preserved szechuan pickle and does not influence the taste of the preserved szechuan pickle; the method has strong adaptability and can be popularized and applied to other aspects in the field of food processing.

Description

Method for inhibiting hydrogen sulfide generation in hot pickled mustard tuber production
Technical Field
The invention relates to the field of food processing, in particular to a method for inhibiting hydrogen sulfide generation in the production process of hot pickled mustard tuber.
Background
The preserved szechuan pickle is a simple and delicious food, is popular among people in most regions, and the preparation process of the preserved szechuan pickle generally comprises the following steps: cleaning, pickling, dewatering, salting, packaging, fermenting, mixing, and packaging to obtain the final product, wherein in the production process of hot pickled mustard tuber, since vegetables are sulfur-containing organic substances, the organic substances can generate toxic gas hydrogen sulfide (H) in the anaerobic decomposition process2S), hydrogen sulfide is a highly toxic substance, the toxicity of the hydrogen sulfide is second to cyanide, the hydrogen sulfide is widely used in industries such as oil gas production, paper-making leather, sewage treatment, food processing and the like, and the hydrogen sulfide can cause damage to human bodies when the concentration of the hydrogen sulfide in air exceeds 10 ppm. In the production of the preserved szechuan pickle, the concentration of hydrogen sulfide under partial conditions even exceeds 1000ppm, and workers can be poisoned and even die if the workers do not timely treat the generated hydrogen sulfide in the production process, and safety accidents caused by the poisoning of the hydrogen sulfide occur in domestic preserved szechuan pickle plants, thereby bringing disastrous results to enterprises and workers.
In the current industrial production, the generation of hydrogen sulfide is generally reduced by adopting a method of adding compounds such as hydrogen peroxide, organic alcohol amine and the like as a hydrogen sulfide inhibitor, so that the content of the hydrogen sulfide in the air is reduced, but the chemical agents also have certain toxicity, cannot be used as additives to be put into food, and cannot meet the requirements of tuber mustard production. To inhibit hydrogen sulfide by adding an inhibitor, it is necessary to provide a non-toxic and harmless inhibitor to ensure food safety.
The reasons for generating hydrogen sulfide in the process of producing the preserved szechuan pickle are mainly two: firstly, certain microorganisms can decompose sulfur-containing organic matters such as tryptophan, cysteine, coenzyme A, biotinidase and the like in vegetables under anaerobic conditions; and the other is that the sulfate in the salt can be reduced by microorganism sulfate reducing bacteria such as gram negative and endogenous bacillus. For these two reasons, the generation of hydrogen sulfide can be reduced radically by adding some safe and effective chemical inhibitors in the production process of the preserved szechuan pickle to inhibit the growth of microorganisms. However, the existing tuber mustard manufacturers do not adopt the method to inhibit the generation of hydrogen sulfide, generally, after the hydrogen sulfide is generated, the hydrogen sulfide is naturally discharged by simply adopting physical methods such as ventilation, water dissolution and the like, and the methods are difficult to ensure that the content of the hydrogen sulfide in the production environment is kept in a standard range, thereby causing potential safety hazards.
Disclosure of Invention
In view of the above problems, an object of the present invention is to provide a method for effectively inhibiting the generation of hydrogen sulfide in the production of hot pickled mustard tuber, which is characterized in that while the prior art of the physical treatment of hydrogen sulfide is maintained, a hydrogen sulfide inhibitor meeting the food processing requirements is added to treat the production process of hot pickled mustard tuber, so as to reduce the generation of hydrogen sulfide and ensure the production safety.
The technical scheme of the invention is as follows:
a method for inhibiting hydrogen sulfide generation in preserved szechuan pickle production comprises the following steps:
s1, cleaning fresh green head vegetables to be used as a raw material of hot pickled mustard tuber;
s2, putting the cleaned preserved szechuan pickle raw materials into a pickle tank, adding salt for pickling for 2-3 days to obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% of hydrogen sulfide inhibitor during pickling;
s3, fishing out the pickled mustard tuber semi-finished product, and washing with water for desalting;
s4, adding 0.1-0.2% of hydrogen sulfide inhibitor into the desalted preserved szechuan pickle, mixing uniformly, putting into a plastic film bag, vacuumizing for storage, and sealing and fermenting at a set temperature for 10 days to obtain a finished preserved szechuan pickle; during the fermentation process, the tuber mustard in partial fermentation is selected for testing, and the hydrogen sulfide production amount is judged.
Further, the hydrogen sulfide inhibitor is a fructose derivative. The fructose derivative can inhibit the growth of microorganisms, reduce the decomposition of organic matters and reduce the amount of hydrogen sulfide generated by the putrefaction of amino acid.
Further, the fructose derivative is fructose derivative I ((3a 'R,4S,7a' R) -2,2,2',2' -tetramethyldihydrospiro [1, 3-dioxalane-4, 6'- [1,3] dioxazo [4,5-c ] pyran ] -7' (4'H) -one), fructose derivative II ((3aR,6S,7aR) -2,2,2',2 '-tetramethyl-3' - (4-methylphenyl) dihydrospiro [1, 3-dioxazo [4,5-c ] pyrano-6, 5'- [1,3] oxazolidine ] -7(4H) -one), fructose derivative III ((3aR,6S,7aR) -3' - (4-ethylphenyl) -2, one or more of 2,2',2' -tetramethyl dihydro spiro [1, 3-dioxazo [4,5-c ] pyrano-6, 5' - [1,3] oxazolidine ] -7(4H) -ketone), and the structural formulas are respectively as follows:
the fructose derivative I, the fructose derivative II and the fructose derivative III are respectively prepared into a No. 1 hydrogen sulfide inhibitor, a No. 2 hydrogen sulfide inhibitor and a No. 3 hydrogen sulfide inhibitor with clear water.
Further, in step S2, the tuber mustard raw material: the mass ratio of the salt is 100: 2 to 8.
Further, in step S3, the pickled mustard tuber semi-finished product is washed and desalted until the surface is free of salt crystals.
Further, in step S3, the operator needs to keep a safe distance and wear a negative pressure mask during the fishing and cleaning process.
Further, in the step S4, the set temperature is 25 to 35 ℃.
Further, in the step S4, 1 part of preserved szechuan pickle in fermentation is selected, the vacuumized plastic film bag is opened, the lead acetate test paper stained with water is put into the vacuum bag by tweezers every 1 day, the color change of the test paper is observed, and the hydrogen sulfide production amount is judged according to the color depth of the test paper.
Further, in the step S4, a concentration curve chart of the hydrogen sulfide production amount during the fermentation period is drawn according to the color change of the test paper, and the hydrogen sulfide content value generated every day during the fermentation period is established based on the concentration curve chart.
Further, in the step S4, when the test paper color determines that the hydrogen sulfide content exceeds the standard, the hydrogen sulfide inhibitor is added again to keep the hydrogen sulfide content within the safety standard.
The invention has the advantages that:
1. the fructose derivative is adopted to inhibit the hydrogen sulfide generated in the production process of the preserved szechuan pickle, the generation amount of the hydrogen sulfide is obviously reduced, and the harmfulness of the production process of the preserved szechuan pickle is obviously reduced;
2. the fructose derivative is used as the hydrogen sulfide inhibitor, has wide raw material source, low cost, no toxicity, easy degradation, greenness and no pollution, can meet the requirements of tuber mustard production, and is also suitable for other food processing fields;
3. the method for inhibiting the generation of hydrogen sulfide in the production of hot pickled mustard tuber has the advantages of simple operation, obvious effect of inhibiting the hydrogen sulfide, no damage to the taste of the hot pickled mustard tuber, environmental protection and the like.
Detailed Description
The present invention will be described in further detail with reference to the following examples, but the present invention is not limited thereto.
In the following examples, all chemicals were obtained in a conventional manner unless otherwise specified.
In the following examples, "%" is a mass percentage unless otherwise specified.
In the hydrogen sulfide inhibitor provided by the invention, the hydrogen sulfide inhibitors No. 1, No. 2 and No. 3 can be eaten, wherein the hydrogen sulfide inhibitor No. 1 is an existing product and can be directly purchased, and the hydrogen sulfide inhibitors No. 2 and No. 3 need to be prepared by self.
Example 1:
the invention provides a method for synthesizing a No. 2 hydrogen sulfide inhibitor in hydrogen sulfide inhibitors, which comprises the following steps:
(1) adding 167mmol of D-glucose and 224mmol of p-methylaniline into a mixed solution of 9mL of water and 3.0mmol of acetic acid, heating the mixed solution to 100 ℃ in an oil bath, stirring the mixed solution for 1 hour, and cooling the mixed solution to room temperature;
(2) adding 300mL of ethanol into the mixture for dilution, freezing at minus 25 ℃ for 24h, filtering, washing a filter cake by using a mixed solution of ethanol and ether with the volume ratio of 2:3 to obtain a white solid 1-p-toluidinyl-1-deoxy-D-fructose;
(3) to a solution of 72.0mmol of 1-p-toluidinyl-1-deoxy-D-fructose and 146.0mmol of trimethyl orthoformate in acetone at 0 ℃ was added 225.0mmol of H2SO4；
(4) Stirring at 0 deg.C for 2 hours with NH4OH termination, filtration and concentration to give a solid as CH2Cl2Dissolving and using Na2SO4Drying, filtering again and concentrating to about 50 mL;
(5) adding boiling 150mL of n-hexane into the solution, standing the mixture at room temperature for 1 hour, freezing at-25 ℃ for 2 hours, filtering, and washing with cooled n-hexane to obtain a white solid product, namely aminodiol;
(6) 25.0mmol of aminodiol 72.0mmol of triethylamine in CH2Cl2Dripping 31.0mmol 20% phosgene toluene solution into the solution at 0 ℃, stirring the solution for 6 hours at 0 ℃ after more than 30 minutes, adding 60mL 1mol/L NaOH, stirring for 5 minutes, and stopping the reaction;
(7) standing the solution for layering, and adding CH to the water layer2Cl2Extracting, mixing the organic phase with 1mol/L HCl and saturated NaHCO respectively3Washed with saturated brine and Na2SO4Drying, concentrating, and dissolving in 100mL methanol;
(8) adding solid 25.0mmol of K2CO3Stirring at room temperature for 30 min, concentrating, and adding CH2Cl2Dissolving, washing with water, and adding Na2SO4Drying, filtering and concentrating the solution to 30 mL;
(9) adding 90mL of boiling n-hexane, standing the mixed solution at room temperature for 1 hour, freezing at-25 ℃ for 1 hour, filtering, and washing with cold n-hexane to obtain white solid alcohol;
(10) adding CH of solid alcohol2Cl2The solution was added to freshly ground 18.0g of 0.3nm molecular sieve, 30.0mmol of Pyridinium Dichromate (PDC) and 3 drops of acetic acid inStirring overnight at room temperature;
(11) the mixture was passed through a celite pad, washed with ether, then passed through a short silica gel column, washed with ether, concentrated, and then washed with 15mL of CH2Cl2Dissolving;
(12) adding 60mL of boiling n-hexane, standing at room temperature for 3 hours, freezing at-25 ℃ for 2 hours, and filtering to obtain white solid ketone;
(13) the above product was purified by chromatography (developing solvent: v (n-hexane): v (ethyl acetate): 1) to give inhibitor No. 2 in 72% yield.
Example 2:
the synthesis method of the No. 3 hydrogen sulfide inhibitor comprises the following steps:
(1) adding 167mmol of D-glucose and 224mmol of p-ethylaniline into a mixed solution of 9mL of water and 3.0mmol of acetic acid, heating the mixed solution to 100 ℃ in an oil bath, stirring the mixed solution for 1 hour, and cooling the mixed solution to room temperature;
(2) the mixture was diluted with 300mL of ethanol, frozen at-25 ℃ for 24 hours, filtered, and the filter cake was diluted with 2:3, washing with mixed solution of ethanol and diethyl ether to obtain white solid 1-p-ethylanilino-1-deoxy-D-fructose;
(3) to a solution of 72.0mmol of 1-p-ethylanilino-1-deoxy-D-fructose and 146.0mmol of trimethyl orthoformate in acetone at 0 ℃ was added 225.0mmol of H2SO4；
(4) Stirring at 0 deg.C for 2 hours with NH4OH termination, filtration and concentration to give a solid as CH2Cl2Dissolving and using Na2SO4Drying, filtering again and concentrating to about 50 mL;
(5) adding boiling 150mL of n-hexane into the solution, standing the mixture at room temperature for 1 hour, freezing at-25 ℃ for 2 hours, filtering, and washing with cooled n-hexane to obtain a white solid product, namely aminodiol;
(6) 25.0mmol of aminodiol 72.0mmol of triethylamine in CH2Cl2The solution was added dropwise to 31.0mmol of 20% phosgene-toluene solution at 0 ℃ for more than 30 minutes, after which the solution was stirred at 0 ℃ for 6 hours, 60mL of 1mol/L NaOH was added thereto and stirred for 5 minutes to terminate the reactionThe preparation method comprises the following steps of;
(7) standing the solution for layering, and adding CH to the water layer2Cl2Extracting, mixing the organic phase with 1mol/LHCl and saturated NaHCO3Washed with saturated brine and Na2SO4Drying, concentrating, and dissolving in 100mL methanol;
(8) adding solid 25.0mmol of K2CO3Stirring at room temperature for 30 min, concentrating, and adding CH2Cl2Dissolving, washing with water, and adding Na2SO4Drying, filtering and concentrating the solution to 30 mL;
(9) adding 90mL of boiling n-hexane, standing the mixed solution at room temperature for 1 hour, freezing at-25 ℃ for 1 hour, filtering, and washing with cold n-hexane to obtain white solid alcohol;
(10) adding CH of solid alcohol2Cl2Adding the milled 18.0g of 0.3nm molecular sieve, 30.0mmol of Pyridinium Dichromate (PDC) and 3 drops of acetic acid into the solution, and stirring at room temperature overnight;
(11) the mixture was passed through a celite pad, washed with ether, then passed through a short silica gel column, washed with ether, concentrated and then washed with 15mL CH2Cl2Dissolving;
(12) adding 60mL of boiling n-hexane, standing at room temperature for 3 hours, freezing at-25 ℃ for 2 hours, and filtering to obtain white solid ketone;
(13) the above product was purified by chromatography (developing solvent: v (n-hexane): v (ethyl acetate): 1) to give inhibitor No. 3 in 65% yield.
Example 3:
the purchased hydrogen sulfide inhibitor No. 1 is used for carrying out experiments on the situation of inhibiting the generation of hydrogen sulfide in the production process of preserved szechuan pickle, and the steps are as follows:
(1) cleaning fresh green head vegetables;
(2) putting the cleaned preserved szechuan pickle raw material into a pickle tank, adding salt according to the proportion of 2-8% (preferably 4%) for pickling for 2-3 days to preferably obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% (preferably 0.5%) of a hydrogen sulfide inhibitor during pickling;
(3) fishing out the preserved szechuan pickle raw materials, and washing and desalting with a large amount of water;
(4) mixing the desalted preserved szechuan pickle raw materials with 0.1-0.2% (preferably 0.15%) of No. 1 inhibitor, putting the mixture into a plastic film bag, vacuumizing, and sealing and fermenting for 10 days at the temperature of 25 ℃; and (5) putting the lead acetate test paper stained with water into the vacuum bag by using tweezers every 1 day, and observing whether the test paper is discolored and the depth of the color.
After the treatment according to the above steps, the result of observing the color of the test paper is shown in table 1. Table 1 shows that no hydrogen sulfide is generated in the first 3 days, a small amount of hydrogen sulfide is generated in 4-7 days, the concentration is kept in a certain range, the hydrogen sulfide is gradually increased in 8-10 days, but the color of the test paper does not become black, and the color of the test paper does not exceed 10ppm, so that the hydrogen sulfide inhibitor No. 1 can effectively inhibit the growth of microorganisms at 25 ℃, and the effect of reducing the generation amount of the hydrogen sulfide is achieved.
Inhibition effect of hydrogen sulfide inhibitor No. 11 at 25 deg.C
Example 4:
a method for inhibiting hydrogen sulfide generation in the production of hot pickled mustard tuber effectively comprises the following steps:
(1) cleaning fresh green head vegetables;
(2) putting the cleaned preserved szechuan pickle raw material into a pickle tank, adding salt according to the proportion of 2-8% (preferably 4%) for pickling for 2-3 days to preferably obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% (preferably 0.5%) of a hydrogen sulfide inhibitor during pickling;
(3) fishing out the preserved szechuan pickle raw materials, and washing and desalting with a large amount of water;
(4) mixing the desalted preserved szechuan pickle raw materials with 0.1-0.2% (preferably 0.15%) of No. 1 hydrogen sulfide inhibitor, putting the mixture into a plastic film bag, vacuumizing, and sealing and fermenting for 10 days at the temperature of 30 ℃; and (5) putting the lead acetate test paper stained with water into the vacuum bag by using tweezers every 1 day, and observing whether the test paper is discolored and the depth of the color.
After the treatment according to the above steps, the result of observing the color of the test paper is shown in Table 2. Table 2 shows that no hydrogen sulfide is generated in the first 3 days, a small amount of hydrogen sulfide is generated in 4-6 days, the concentration is kept in a certain range, the hydrogen sulfide is gradually increased in 7-10 days, but the color of the test paper does not become black, and the inhibitor No. 1 can effectively inhibit the growth of microorganisms at 30 ℃, so that the effect of reducing the generation amount of the hydrogen sulfide is achieved.
Inhibition effect of hydrogen sulfide inhibitor No. 21 in 30 deg.C
Example 5:
a method for inhibiting hydrogen sulfide generation in the production of hot pickled mustard tuber effectively comprises the following steps:
(1) cleaning fresh green head vegetables;
(2) putting the cleaned preserved szechuan pickle raw material into a pickle tank, adding salt according to the proportion of 2-8% (preferably 4%) for pickling for 2-3 days to preferably obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% (preferably 0.5%) of a hydrogen sulfide inhibitor during pickling;
(3) fishing out the preserved szechuan pickle raw materials, and washing and desalting with a large amount of water;
(4) mixing the desalted preserved szechuan pickle raw materials with 0.1-0.2% (preferably 0.15%) of No. 1 hydrogen sulfide inhibitor, putting the mixture into a plastic film bag, vacuumizing, and sealing and fermenting for 10 days at the temperature of 35 ℃; and (5) putting the lead acetate test paper stained with water into the vacuum bag by using tweezers every 1 day, and observing whether the test paper is discolored and the depth of the color.
After the treatment according to the above steps, the result of observing the color of the test paper is shown in Table 3. Table 3 shows that no hydrogen sulfide is generated in the first 2 days, a small amount of hydrogen sulfide is generated in 3-4 days, the concentration is kept in a certain range, the hydrogen sulfide is gradually increased in 5-7 days, the hydrogen sulfide concentration is increased again in more than 8 days, but the color of the test paper does not become black, and the hydrogen sulfide inhibitor No. 1 can effectively inhibit the growth of microorganisms at 35 ℃ so as to achieve the effect of reducing the generation amount of the hydrogen sulfide, but the effect is not as good as that at 25 ℃ and 30 ℃ under the ambient temperature.
Inhibition effect of hydrogen sulfide inhibitor No. 31 in 35 deg.C
Example 6:
a method for inhibiting hydrogen sulfide generation in the production of hot pickled mustard tuber effectively comprises the following steps:
(1) cleaning fresh green head vegetables;
(2) putting the cleaned preserved szechuan pickle raw material into a pickle tank, adding salt according to the proportion of 2-8% (preferably 4%) for pickling for 2-3 days to preferably obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% (preferably 0.5%) of a hydrogen sulfide inhibitor during pickling;
(3) fishing out the preserved szechuan pickle raw materials, and washing and desalting with a large amount of water;
(4) mixing the desalted preserved szechuan pickle raw materials with 0.1-0.2% (preferably 0.15%) of No. 2 hydrogen sulfide inhibitor, putting the mixture into a plastic film bag, vacuumizing, and sealing and fermenting for 10 days at 25 ℃; and (5) putting the lead acetate test paper stained with water into the vacuum bag by using tweezers every 1 day, and observing whether the test paper is discolored and the depth of the color.
After the treatment according to the above steps, the result of observing the color of the test paper is shown in Table 4. Table 4 shows that no hydrogen sulfide is generated in the first 5 days, a small amount of hydrogen sulfide is generated in 6-10 days, the concentration is kept in a certain range, but the color of the test paper is not darkened, which indicates that the hydrogen sulfide inhibitor No. 2 has a good inhibition effect on the growth of microorganisms at 25 ℃, the generation of hydrogen sulfide can be greatly reduced, and the effect is superior to that of the hydrogen sulfide inhibitor No. 1.
Inhibition effect of hydrogen sulfide inhibitor No. 42 in 25 deg.C
Example 7:
a method for inhibiting hydrogen sulfide generation in the production of hot pickled mustard tuber effectively comprises the following steps:
(1) cleaning fresh green head vegetables;
(2) putting the cleaned preserved szechuan pickle raw material into a pickle tank, adding salt according to the proportion of 2-8% (preferably 4%) for pickling for 2-3 days to preferably obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% (preferably 0.5%) of a hydrogen sulfide inhibitor during pickling;
(3) fishing out the preserved szechuan pickle raw materials, and washing and desalting with a large amount of water;
(4) mixing the desalted preserved szechuan pickle raw materials with 0.1-0.2% (preferably 0.15%) of No. 2 hydrogen sulfide inhibitor, putting the mixture into a plastic film bag, vacuumizing, and sealing and fermenting for 10 days at the temperature of 30 ℃; and (5) putting the lead acetate test paper stained with water into the vacuum bag by using tweezers every 1 day, and observing whether the test paper is discolored and the depth of the color.
After the treatment according to the above steps, the result of observing the color of the test paper is shown in Table 5. Table 5 shows that no hydrogen sulfide is generated in the first 4 days, a small amount of hydrogen sulfide is generated in 5-8 days, the concentration is kept in a certain range, the hydrogen sulfide concentration is increased in 9-10 days, but the color of the test paper does not become black, and the hydrogen sulfide inhibitor No. 2 can effectively inhibit the growth of microorganisms at 30 ℃, so that the effect of reducing the generation amount of hydrogen sulfide is achieved.
Inhibition effect of hydrogen sulfide inhibitor No. 52 at 30 ℃ in Table
Example 8:
a method for inhibiting hydrogen sulfide generation in the production of hot pickled mustard tuber effectively comprises the following steps:
(1) cleaning fresh green head vegetables;
(2) putting the cleaned preserved szechuan pickle raw material into a pickle tank, adding salt according to the proportion of 2-8% (preferably 4%) for pickling for 2-3 days to preferably obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% (preferably 0.5%) of a hydrogen sulfide inhibitor during pickling;
(3) fishing out the preserved szechuan pickle raw materials, and washing and desalting with a large amount of water;
(4) mixing the desalted preserved szechuan pickle raw materials with 0.1-0.2% (preferably 0.15%) of No. 2 hydrogen sulfide inhibitor, putting the mixture into a plastic film bag, vacuumizing, and sealing and fermenting for 10 days at the temperature of 35 ℃; and (5) putting the lead acetate test paper stained with water into the vacuum bag by using tweezers every 1 day, and observing whether the test paper is discolored and the depth of the color.
After the treatment according to the above steps, the result of observing the color of the test paper is shown in Table 6. Table 6 shows that no hydrogen sulfide is generated in the first 3 days, a small amount of hydrogen sulfide is generated in 4-6 days, the concentration is kept in a certain range, the hydrogen sulfide concentration is increased in 7-10 days, but the color of the test paper does not become black, and the hydrogen sulfide inhibitor No. 2 can effectively inhibit the growth of microorganisms at 35 ℃ so as to achieve the effect of reducing the generation amount of the hydrogen sulfide, but the effect is not as good as that at 25 ℃ and 30 ℃.
Inhibition effect of hydrogen sulfide inhibitor No. 62 in 35 deg.C
Example 9:
a method for inhibiting hydrogen sulfide generation in the production of hot pickled mustard tuber effectively comprises the following steps:
(1) cleaning fresh green head vegetables;
(2) putting the cleaned preserved szechuan pickle raw material into a pickle tank, adding salt according to the proportion of 2-8% (preferably 4%) for pickling for 2-3 days to preferably obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% (preferably 0.5%) of a hydrogen sulfide inhibitor during pickling;
(3) fishing out the preserved szechuan pickle raw materials, and washing and desalting with a large amount of water;
(4) mixing the desalted preserved szechuan pickle raw materials with 0.1-0.2% (preferably 0.15%) of No. 3 hydrogen sulfide inhibitor, putting the mixture into a plastic film bag, vacuumizing, and sealing and fermenting for 10 days at 25 ℃; and (5) putting the lead acetate test paper stained with water into the vacuum bag by using tweezers every 1 day, and observing whether the test paper is discolored and the depth of the color.
After the treatment according to the above steps, the results of observing the color of the test paper are shown in Table 7. Table 7 shows that no hydrogen sulfide is generated in the first 4 days, a small amount of hydrogen sulfide is generated in 5-9 days, the concentration is kept in a certain range, the hydrogen sulfide concentration is increased in the 10 th day, but the color of the test paper is not darkened, and the hydrogen sulfide inhibitor No. 3 can effectively inhibit the growth of microorganisms at 25 ℃, so that the effect of reducing the generation amount of hydrogen sulfide is achieved, and the effect is between I and II.
Inhibition effect of hydrogen sulfide inhibitor No. 73 at 25 deg.C
Example 10:
a method for inhibiting hydrogen sulfide generation in the production of hot pickled mustard tuber effectively comprises the following steps:
(1) cleaning fresh green head vegetables;
(2) putting the cleaned preserved szechuan pickle raw material into a pickle tank, adding salt according to the proportion of 2-8% (preferably 4%) for pickling for 2-3 days to preferably obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% (preferably 0.5%) of a hydrogen sulfide inhibitor during pickling;
(3) fishing out the preserved szechuan pickle raw materials, and washing and desalting with a large amount of water;
(4) mixing the desalted preserved szechuan pickle raw materials with 0.1-0.2% (preferably 0.15%) of No. 3 hydrogen sulfide inhibitor, putting the mixture into a plastic film bag, vacuumizing, and sealing and fermenting for 10 days at the temperature of 30 ℃; and (5) putting the lead acetate test paper stained with water into the vacuum bag by using tweezers every 1 day, and observing whether the test paper is discolored and the depth of the color.
After the treatment according to the above steps, the result of observing the color of the test paper is shown in Table 8. Table 8 shows that no hydrogen sulfide is generated in the first 4 days, a small amount of hydrogen sulfide is generated in 5-7 days, the concentration is kept in a certain range, the hydrogen sulfide concentration is increased in 8-10 days, but the color of the test paper is not darkened, and the hydrogen sulfide inhibitor No. 3 can effectively inhibit the growth of microorganisms at 30 ℃, so that the effect of reducing the generation amount of hydrogen sulfide is achieved.
Inhibition effect of hydrogen sulfide inhibitor No. 83 in 30 deg.C
Example 11:
a method for inhibiting hydrogen sulfide generation in the production of hot pickled mustard tuber effectively comprises the following steps:
(1) cleaning fresh green head vegetables;
(2) putting the cleaned preserved szechuan pickle raw material into a pickle tank, adding salt according to the proportion of 2-8% (preferably 4%) for pickling for 2-3 days to preferably obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% (preferably 0.5%) of a hydrogen sulfide inhibitor during pickling;
(3) fishing out the preserved szechuan pickle raw materials, and washing and desalting with a large amount of water;
(4) mixing the desalted preserved szechuan pickle raw materials with 0.1-0.2% (preferably 0.15%) of No. 3 hydrogen sulfide inhibitor, putting the mixture into a plastic film bag, vacuumizing, and sealing and fermenting for 10 days at the temperature of 35 ℃; and (5) putting the lead acetate test paper stained with water into the vacuum bag by using tweezers every 1 day, and observing whether the test paper is discolored and the depth of the color.
After the treatment according to the above steps, the results of observing the color of the test paper are shown in Table 9. Table 9 shows that no hydrogen sulfide is generated in the first 3 days, a small amount of hydrogen sulfide is generated in 4-6 days, the concentration is kept in a certain range, the hydrogen sulfide concentration is increased in 7-8 days, the hydrogen sulfide concentration is continuously increased in 9-10 days, but the color of the test paper is not changed into black, which shows that the No. 3 hydrogen sulfide inhibitor can effectively inhibit the growth of microorganisms at 35 ℃, so that the effect of reducing the generation amount of the hydrogen sulfide is achieved, but the effect is not as good as that at 25 ℃ and 30 ℃.
Inhibition effect of hydrogen sulfide inhibitor No. 93 in 35 deg.C
Experiments show that the method for inhibiting the generation of hydrogen sulfide in the production of hot pickled mustard tuber can effectively inhibit the generation of hydrogen sulfide in the production process of hot pickled mustard tuber, and particularly, the hydrogen sulfide inhibiting effect is best when a No. 3 hydrogen sulfide inhibitor is adopted at the temperature of 25-30 ℃. The method can ensure the food safety of the preserved szechuan pickle while reducing the generation amount of the hydrogen sulfide, does not reduce the mouthfeel, has strong adaptability, and can be popularized and applied to other aspects in the field of food processing.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that the invention is not limited to the above-mentioned embodiments, and can be further modified without departing from the principle of the invention, and these modifications should also be regarded as the protection scope of the present invention.

Claims (8)

1. A method for inhibiting hydrogen sulfide generation in preserved szechuan pickle production is characterized by comprising the following steps:
s1, cleaning fresh green head vegetables to be used as a raw material of hot pickled mustard tuber;
s2, putting the cleaned preserved szechuan pickle raw materials into a pickle tank, adding salt for pickling for 2-3 days to obtain a preserved szechuan pickle semi-finished product, and adding 0.1-0.5% of hydrogen sulfide inhibitor during pickling;
s3, fishing out the pickled mustard tuber semi-finished product, and washing with water for desalting;
s4, adding 0.1-0.2% of hydrogen sulfide inhibitor into the desalted preserved szechuan pickle, mixing uniformly, putting into a plastic film bag, vacuumizing for storage, and sealing and fermenting at the set temperature of 25 ℃, 30 ℃ and 35 ℃ for 10 days to obtain a finished preserved szechuan pickle; during the fermentation process, selecting a part of the pickled mustard tuber in the fermentation for testing, and judging the generation amount of hydrogen sulfide;
the hydrogen sulfide inhibitor is a fructose derivative, the fructose derivative is a fructose derivative I ((3a 'R,4S,7a' R) -2,2,2',2' -tetramethyl dihydrospiro [1, 3-dioxolane-4, 6'- [1,3] dioxazolo [4,5-c ] pyran ] -7' (4'H) -one), a fructose derivative II ((3aR,6S,7aR) -2,2,2',2 '-tetramethyl-3' - (4-methylphenyl) dihydrospiro [1, 3-dioxazolo [4,5-c ] pyrano-6, 5'- [1,3] oxazolidine ] -7(4H) -one), a fructose derivative III ((3aR,6S,7aR) -3' - (4-ethylphenyl) -2, one or more of 2,2',2' -tetramethyl dihydro spiro [1, 3-dioxazo [4,5-c ] pyrano-6, 5' - [1,3] oxazolidine ] -7(4H) -ketone), and the structural formulas are respectively as follows:
the fructose derivative I, the fructose derivative II and the fructose derivative III are respectively prepared into a No. 1 hydrogen sulfide inhibitor, a No. 2 hydrogen sulfide inhibitor and a No. 3 hydrogen sulfide inhibitor with clear water.
2. The method as claimed in claim 1, wherein the salt is present in a ratio of 2-8% by mass in step S2.
3. The method of claim 1, wherein in step S4, 1 part of the preserved szechuan pickle is selected, the vacuumized plastic film bag is opened, the lead acetate test paper with water is inserted into the vacuum bag by tweezers every 1 day, the color change of the test paper is observed, and the amount of the hydrogen sulfide produced is determined according to the color depth of the test paper.
4. The method as claimed in claim 3, wherein in step S4, a graph of the hydrogen sulfide content during fermentation is plotted according to the color change of the test paper, and the hydrogen sulfide content during fermentation is determined according to the graph.
5. The method of claim 4, wherein in step S4, when the test paper color indicates that the hydrogen sulfide content is out of limits, the hydrogen sulfide inhibitor is added again to keep the hydrogen sulfide content within the safety standard.
6. The method as claimed in claim 1, wherein in step S4, when the test paper color indicates that the hydrogen sulfide content is out of limits, the hydrogen sulfide inhibitor is added again to keep the hydrogen sulfide content within the safety standard.
7. The method for inhibiting the generation of hydrogen sulfide in the production of hot pickled mustard tuber according to claim 1, wherein the method for synthesizing the No. 2 hydrogen sulfide inhibitor in the provided hydrogen sulfide inhibitors comprises the following steps:
(1) adding 167mmol of D-glucose and 224mmol of p-methylaniline into a mixed solution of 9mL of water and 3.0mmol of acetic acid, heating the mixed solution to 100 ℃ in an oil bath, stirring the mixed solution for 1 hour, and cooling the mixed solution to room temperature;
(2) adding 300mL of ethanol into the mixture for dilution, freezing at minus 25 ℃ for 24h, filtering, washing a filter cake by using a mixed solution of ethanol and ether with the volume ratio of 2:3 to obtain a white solid 1-p-toluidinyl-1-deoxy-D-fructose;
(3) to a solution of 72.0mmol of 1-p-toluidinyl-1-deoxy-D-fructose and 146.0mmol of trimethyl orthoformate in acetone at 0 ℃ was added 225.0mmol of H2SO4；
(4) Stirring at 0 deg.C for 2 hours with NH4OH termination, filtration and concentration to give a solid as CH2Cl2Dissolving and using Na2SO4Drying, filtering again and concentrating to about 50 mL;
(5) adding boiling 150mL of n-hexane into the solution, standing the mixture at room temperature for 1 hour, freezing at-25 ℃ for 2 hours, filtering, and washing with cooled n-hexane to obtain a white solid product, namely aminodiol;
(6) 25.0mmol of aminodiol 72.0mmol of triethylamine in CH2Cl2Dripping 31.0mmol 20% phosgene toluene solution into the solution at 0 ℃, stirring the solution for 6 hours at 0 ℃ after more than 30 minutes, adding 60mL 1mol/L NaOH, stirring for 5 minutes, and stopping the reaction;
(7) standing the solution for layering, and adding CH to the water layer2Cl2Extracting, mixing the organic phase with 1mol/L HCl and saturated NaHCO respectively3Washed with saturated brine and Na2SO4Drying, concentrating, and dissolving in 100mL methanol;
(8) adding solid 25.0mmol of K2CO3Stirring at room temperature for 30 min, concentrating, and adding CH2Cl2Dissolving, washing with water, and adding Na2SO4Drying, filtering and concentrating the solution to 30 mL;
(9) adding 90mL of boiling n-hexane, standing the mixed solution at room temperature for 1 hour, freezing at-25 ℃ for 1 hour, filtering, and washing with cold n-hexane to obtain white solid alcohol;
(10) adding CH of solid alcohol2Cl2Adding the milled 18.0g of 0.3nm molecular sieve, 30.0mmol of Pyridinium Dichromate (PDC) and 3 drops of acetic acid into the solution, and stirring at room temperature overnight;
(11) the mixture was passed through a celite pad, washed with ether, then passed through a short silica gel column, washed with ether, concentrated, and then washed with 15mL of CH2Cl2Dissolving;
(12) adding 60mL of boiling n-hexane, standing at room temperature for 3 hours, freezing at-25 ℃ for 2 hours, and filtering to obtain white solid ketone;
(13) the above product was purified by chromatography (developing solvent: v (n-hexane): v (ethyl acetate): 1) to give inhibitor No. 2 in 72% yield.
8. The method for inhibiting the generation of hydrogen sulfide in the production of hot pickled mustard tuber according to claim 1, wherein the method for synthesizing the No. 3 hydrogen sulfide inhibitor in the provided hydrogen sulfide inhibitors comprises the following steps:
(1) adding 167mmol of D-glucose and 224mmol of p-ethylaniline into a mixed solution of 9mL of water and 3.0mmol of acetic acid, heating the mixed solution to 100 ℃ in an oil bath, stirring the mixed solution for 1 hour, and cooling the mixed solution to room temperature;
(2) the mixture was diluted with 300mL of ethanol, frozen at-25 ℃ for 24 hours, filtered, and the filter cake was diluted with 2:3, washing with mixed solution of ethanol and diethyl ether to obtain white solid 1-p-ethylanilino-1-deoxy-D-fructose;
(3) to a solution of 72.0mmol of 1-p-ethylanilino-1-deoxy-D-fructose and 146.0mmol of trimethyl orthoformate in acetone at 0 ℃ was added 225.0mmol of H2SO4；
(4) Stirring at 0 deg.C for 2 hours with NH4OH termination, filtration and concentration to give a solid as CH2Cl2Dissolving and using Na2SO4Drying, filtering again and concentrating to about 50 mL;
(5) adding boiling 150mL of n-hexane into the solution, standing the mixture at room temperature for 1 hour, freezing at-25 ℃ for 2 hours, filtering, and washing with cooled n-hexane to obtain a white solid product, namely aminodiol;
(6) 25.0mmol of aminodiol 72.0mmol of triethylamine in CH2Cl2Dripping 31.0mmol of 20% phosgene toluene solution into the solution at 0 ℃, stirring the solution at 0 ℃ for 6 hours after more than 30 minutes, adding 60mL of 1mol/L NaOH, stirring for 5 minutes, and stopping the reaction;
(7) standing the solution for layering, and adding CH to the water layer2Cl2Extracting, mixing the organic phase with 1mol/LHCl and saturated NaHCO3Washed with saturated brine and Na2SO4Drying, concentrating, and dissolving in 100mL methanol;
(8) adding solid 25.0mmol of K2CO3Stirring at room temperature for 30 min, concentrating, and adding CH2Cl2Dissolving, washing with water, and adding Na2SO4Drying, filtering and concentrating the solution to 30 mL;
(9) adding 90mL of boiling n-hexane, standing the mixed solution at room temperature for 1 hour, freezing at-25 ℃ for 1 hour, filtering, and washing with cold n-hexane to obtain white solid alcohol;
(10) adding CH of solid alcohol2Cl2Adding the milled 18.0g of 0.3nm molecular sieve, 30.0mmol of Pyridinium Dichromate (PDC) and 3 drops of acetic acid into the solution, and stirring at room temperature overnight;
(11) the mixture was passed through a celite pad, washed with ether, then passed through a short silica gel column, washed with ether, concentrated and then washed with 15mL CH2Cl2Dissolving;
(12) adding 60mL of boiling n-hexane, standing at room temperature for 3 hours, freezing at-25 ℃ for 2 hours, and filtering to obtain white solid ketone;
(13) the above product was purified by chromatography (developing solvent: v (n-hexane): v (ethyl acetate): 1) to give inhibitor No. 3 in 65% yield.
CN201911042845.6A 2016-10-13 2016-10-13 Method for inhibiting hydrogen sulfide generation in hot pickled mustard tuber production Pending CN110584045A (en)

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