CN115381094B - Low-odor water-soluble copper chlorophyll and preparation method and application thereof - Google Patents

Low-odor water-soluble copper chlorophyll and preparation method and application thereof Download PDF

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CN115381094B
CN115381094B CN202210995058.9A CN202210995058A CN115381094B CN 115381094 B CN115381094 B CN 115381094B CN 202210995058 A CN202210995058 A CN 202210995058A CN 115381094 B CN115381094 B CN 115381094B
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low
odor
copper chlorophyll
chlorophyll
water
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CN115381094A (en
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李宏龙
徐小松
金子恒
李林正
郭玉莲
章文晋
於春峰
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HENAN ZHONGDA BIOLOGICAL ENGINEERING CO LTD
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HENAN ZHONGDA BIOLOGICAL ENGINEERING CO LTD
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    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
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    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/20—Removal of unwanted matter, e.g. deodorisation or detoxification
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    • A61K31/00—Medicinal preparations containing organic active ingredients
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    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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    • A61K31/409—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having four such rings, e.g. porphine derivatives, bilirubin, biliverdine
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Abstract

The invention belongs to the technical field of natural product preparation, and particularly relates to low-odor water-soluble copper chlorophyll and a preparation method and application thereof. The invention adopts paste-like chlorophyll copper as raw material, and respectively carries out deodorization treatment, colloid solution emulsification treatment and secondary microcapsule embedding drying treatment, does not adopt strong alkali saponification or sodium modification operation, has safer and more concise process route, and the obtained low-odor water-soluble chlorophyll copper has good water solubility, is not easy to precipitate in a solution with pH value of 2-4.0, has good stability and low odor, and is not easy to 'bleed' when jelly and jam products are applied.

Description

Low-odor water-soluble copper chlorophyll and preparation method and application thereof
Technical Field
The invention belongs to the technical field of natural product preparation, and particularly relates to low-odor water-soluble copper chlorophyll and a preparation method and application thereof.
Background
Copper chlorophyll, which is a metalloporphyrin, has higher stability than chlorophyll. Meanwhile, based on the special structure of the copper chlorophyll and the chelated nutrient elements in the derivatives thereof, the copper chlorophyll has high application value in foods, medicines and cosmetics. The copper chlorophyll and sodium salt thereof can be widely applied to food such as cream, candy, baking, beverage, fruit wine, jelly, can and the like as a food colorant, and are mainly used for coloring or improving natural green of the food, and improving the product value. The research proves that the copper chlorophyll and the sodium salt thereof have good health effects of eliminating inflammation, protecting liver and the like, and therefore, the copper chlorophyll and the sodium salt thereof can be applied to daily chemical products such as toothpaste, facial cleanser, bath foam and the like. In addition, copper chlorophyll and sodium salt thereof are also used in the medical field as an important raw material for the treatment of hepatitis, stomach diseases and duodenal ulcer.
At present, most of copper chlorophyll and sodium salt thereof in the market take silkworm excrement as raw materials, and the obtained product inevitably contains protein, fat, degradation products thereof and other components in faeces of silkworms, so that obvious bad smell or peculiar smell exists, and the application of the copper chlorophyll and sodium salt thereof in the end product is seriously influenced. In the existing production process, in order to realize the water solubility of the chlorophyll copper, basically, sodium hydroxide is added for saponification or sodium treatment, and the obtained product has good water solubility, but is easy to generate precipitation in a solution with the pH value less than 4.0, has poor light and heat stability, and is easy to generate the problem of bleeding when being applied to jelly and jam. And the sodium hydroxide used in the process is strong alkali, so that the safety risk exists in the production process, and the problems of long process route, high cost and the like in the subsequent purification and other operations are solved.
Disclosure of Invention
In order to overcome the defects and disadvantages of long process route, high cost, poor light and heat stability, odor or peculiar smell and the like of the chlorophyll copper in the prior art, the primary aim of the invention is to provide a preparation method of low-odor water-soluble chlorophyll copper.
The invention also aims to provide the low-odor water-soluble copper chlorophyll prepared by the preparation method, which has good water solubility, is not easy to precipitate in an acidic solution with the pH value of 2.0-4.0, has good stability and low odor (peculiar smell), and is not easy to 'bleed' when being applied.
It is a further object of the present invention to provide the use of the low odor water soluble copper chlorophyll described above.
The aim of the invention is achieved by the following technical scheme:
a preparation method of low-odor water-soluble copper chlorophyll comprises the following steps:
(1) Deodorizing: cleaning pasty copper chlorophyll with alcohol solution containing phosphate or disodium ethylenediamine tetraacetate under stirring, and performing solid-liquid separation to obtain alcohol solution and precipitate;
(2) Concentrating: evaporating and removing residual alcohols in the sediment prepared in the step (1) under a vacuum state to obtain low-odor refined copper chlorophyll ointment;
(3) Dilution: adding vegetable oil to dilute the low-odor refined copper chlorophyll ointment prepared in the step (2) to obtain a low-odor copper chlorophyll raw material, wherein the raw material has good fluidity;
(4) Emulsifying and homogenizing: mixing the low-odor chlorophyll copper raw material prepared in the step (3) with a wall material colloid solution, and then carrying out vacuum high-speed emulsification and ultra-high pressure homogenization to obtain low-odor water-soluble chlorophyll copper emulsion;
(5) Secondary microencapsulation: spraying and granulating the low-odor water-soluble copper chlorophyll emulsion prepared in the step (4), and spraying a coating material in the spraying and granulating process for secondary embedding; finally, drying to obtain low-odor water-soluble copper chlorophyll;
the pasty copper chlorophyll in the step (1) is prepared by taking silkworm excrement as a raw material, and the color value of the pasty copper chlorophyll is preferably E70-80;
the phosphate in the step (1) is preferably at least one of sodium hexametaphosphate, sodium polyphosphate, sodium pyrophosphate and sodium tripolyphosphate;
the mass percentage of the phosphate or disodium ethylenediamine tetraacetate in the alcohol solution in the step (1) is preferably 0.01-5%;
the mass percentage of the phosphate or disodium ethylenediamine tetraacetate in the alcohol solution in the step (1) is more preferably 0.15-0.3%;
the alcohol solution in the step (1) is preferably at least one of ethanol, isopropanol and n-butanol;
the volume percentage of the alcohols in the alcohol solution in the step (1) is preferably 75-100%, and more preferably 90-95%;
the cleaning conditions described in step (1) are preferably: stirring at 30-50 deg.c for 15-90 min; the cleaning times are 1 to 5 times;
the specific steps of the cleaning in the step (1) are as follows:
heating paste copper chlorophyll in water bath at 30-50 deg.c for 30-60 min, and adding alcohol solution while maintaining temperature; adding phosphate or disodium ethylenediamine tetraacetate, and stirring for 15-90 min under the heat preservation condition;
the mass ratio of the alcohol solution to the pasty copper chlorophyll in the step (1) is preferably (2-6): 1, a step of;
the solid-liquid separation in the step (1) can be performed by centrifugation or filtration;
the centrifugation can be one of a butterfly type centrifuge, a tripod type centrifuge, a horizontal screw type centrifuge and a tubular type centrifuge;
the alcohol liquid after the solid-liquid separation in the step (1) can be further concentrated under reduced pressure for recycling;
the evaporation conditions described in step (2) are preferably: the vacuum evaporation temperature is 50-90 ℃, and the vacuum degree is-0.08 MPa to-0.1 MPa;
the vegetable oil in the step (3) is preferably at least one of soybean salad oil, sunflower seed oil, corn oil, safflower seed oil, tea seed oil and cotton seed oil;
the mass ratio of the vegetable oil in the step (3) to the pasty copper chlorophyll in the step (1) is preferably (0.1-10): 1, a step of;
the mass ratio of the vegetable oil in the step (3) to the paste-like copper chlorophyll in the step (1) is further preferably (0.1 to 1): 1, a step of;
the wall material colloid in the step (4) is preferably at least one of sodium starch octenyl succinate, hydroxypropyl starch, acetate starch, carboxymethyl starch, phosphate starch, microporous starch, resistant dextrin, acacia, dasheen, xanthan gum, pullulan, fucan, trehalose and lactose;
the mass percentage of the wall material colloid in the wall material colloid solution in the step (4) is 5-75%;
the wall material colloid solution in the step (4) preferably further comprises at least one of a filler and a natural antioxidant;
the filler is at least one of maltodextrin, microcrystalline cellulose, corn syrup, white sugar, lactitol, erythritol, maltitol, sorbitol, alpha-cyclodextrin, beta-cyclodextrin and gamma-cyclodextrin;
the mass percentage of the filler in the wall material colloid solution is 5-75%;
the natural antioxidant is at least one of Vitamin C (VC), sodium iso-vitamin C (sodium iso-VC), tea polyphenol, quercetin, enzymolysis isoquercitrin, rutin, epigallocatechin gallate (EGCG) and Vitamin E (VE);
the mass percentage of the natural antioxidant in the wall material colloid solution is 0.01-1%;
the mass ratio of the solute to the core material in the wall material colloid solution in the step (4) is preferably (1:1) - (1:0.1);
the conditions of vacuum high-speed emulsification in the step (4) are preferably as follows: the pressure is-0.05 to-0.1 Mpa, and the temperature is 10 to 70 ℃; wherein the temperature is more preferably 25 to 50 ℃;
the pressure of the ultrahigh pressure homogenization in the step (4) is preferably 60-200 Mpa, more preferably 70-180 Mpa;
the coating material in the step (5) is preferably at least one of starch and maltodextrin;
the DE value of the maltodextrin is preferably 5-20;
the coating material in the step (5) accounts for 10-30% of the final product;
the conditions for spray granulation described in step (5) are preferably: the air inlet temperature is 160-200 ℃, the air outlet temperature is 70-100 ℃, and the bottom air temperature is 70-90 ℃;
the low-odor water-soluble copper chlorophyll is prepared by the preparation method;
the low-odor water-soluble copper chlorophyll is applied to foods, cosmetics and medicines;
the principle of the invention is as follows:
according to the invention, alcohol substances such as ethanol and isopropanol are used for dissolving peculiar smell components (mainly small molecular substances such as fatty acid degradation products, protein degradation products and the like) in pasty copper chlorophyll, and phosphate or disodium ethylenediamine tetraacetate and the like are used as chelating agents to fix the copper chlorophyll, so that the process loss in the deodorization process is reduced. And then adopting colloid such as Arabic gum and modified starch as wall materials, preparing the chlorophyll copper into nano emulsion by the processes of emulsification, homogenization and the like, and finally coating starch, maltodextrin and the like in the spray granulation process to obtain the low-odor water-soluble chlorophyll copper microcapsule product with good water solubility.
Compared with the prior art, the invention has the following beneficial effects:
(1) The invention uses paste-like chlorophyll copper as raw material, after deodorization and purification, adopts colloid solution to emulsify and homogenize, then uses maltodextrin and starch as coating material to make secondary embedding.
(2) The invention adopts the alcohol solution containing phosphate or disodium ethylenediamine tetraacetate to refine, can effectively remove small molecular degradation products such as fatty acid degradation products, protein degradation products and the like in the chlorophyll copper raw material, and remarkably reduces bad odor and peculiar smell in the final product, thereby obviously improving the application effect of the chlorophyll copper in the final product.
(3) The invention adopts colloid solution to emulsify copper chlorophyll, and coating materials such as starch, maltodextrin and the like are used for secondary embedding and drying, so that the obtained product has good water solubility, can obviously improve the light stability and the heat stability of the product, has good stability in acidic solution with pH value of 2.0-4.0, and is not easy to generate precipitation.
(4) The low-odor water-soluble copper chlorophyll product prepared by the method is far higher in stability than the prior art product when being applied to jelly and jam products, and is not easy to cause bleeding and other problems.
Drawings
FIG. 1 is a graph showing the bleeding of the low odor water-soluble copper chlorophyll from example 1 in use with a commercially available sodium copper chlorophyll salt jelly.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but embodiments of the present invention are not limited thereto.
The paste copper chlorophyll, which is a raw material in the examples, is commercially available, and is prepared from silkworm excrement.
Example 1
(1) Deodorizing: 2000g of pasty copper chlorophyll with the color value of E70 is weighed and added into a reaction kettle with a stirrer, warm water with the temperature of 45-50 ℃ is introduced into an interlayer of the reaction kettle for cyclic heating for 45min, 8000g of ethanol with the volume percent of 95% is added when materials are in a better flowing state, and the materials are stirred uniformly; slowly adding 200g of sodium hexametaphosphate solution with the mass percent of 10%, and continuously preserving heat and stirring for 40min; separating supernatant and precipitate with a sedimentation type three-foot centrifuge (rotation speed 1500rpm, centrifugation 25 min), and completing the first cleaning; adding the collected precipitate into a reaction kettle, continuously adding 8000g of ethanol with the volume percentage of 95% and stirring uniformly, slowly adding 200g of sodium hexametaphosphate solution with the mass percentage of 10%, continuously preserving heat and stirring for 40min, and separating the supernatant and the precipitate by a sedimentation type tripodia centrifuge (the rotating speed is 1500rpm and the centrifuging is carried out for 20 min) to finish the second cleaning; repeating the cleaning for 4 times according to the operation;
(2) Concentrating: concentrating the supernatant (ethanol) collected in the step (1) under reduced pressure, and independently storing for recycling; after the sediment is collected, evaporating and removing residual ethanol until the residual ethanol content is less than or equal to 200ppm under the conditions of the temperature of 80+/-5 ℃ and the vacuum degree of-0.09 PMa, thereby obtaining 1250g of low-odor refined copper chlorophyll ointment with the color value of E126.2;
(3) Dilution: weighing 750g of non-transgenic soybean salad oil, heating to 70-75 ℃, adding the soybean salad oil into the low-odor refined copper chlorophyll ointment prepared in the step (2), and uniformly stirring to obtain 2000g of low-odor copper chlorophyll raw material with good fluidity, wherein the color value is E71;
(4) Emulsifying and homogenizing: weighing 110g of Arabic gum, 25g of hydroxypropyl starch, 40g of maltodextrin (DE 18), 23g of white sugar and 2g of tea polyphenol, and dissolving in 200g of deionized water to prepare a water-soluble wall material colloid solution with the wall material colloid mass percentage of 33.75%; weighing 200g of the low-odor chlorophyll copper raw material prepared in the step (3), mixing with the water-soluble wall material colloid solution, and emulsifying for 25min at a high speed under the conditions of the pressure of-0.08 MPa and the temperature of 45-50 ℃ until the emulsified feed liquid is uniformly dispersed; homogenizing the emulsified feed liquid under ultrahigh pressure of 135Mpa for 2 times to obtain stable low-odor water-soluble copper chlorophyll emulsion with test particle diameter D50 less than or equal to 500nm;
(5) Secondary microencapsulation: spraying granulation is carried out on the low-odor water-soluble copper chlorophyll emulsion prepared in the step (4), starch is sprayed in the spraying granulation process at the same time for secondary embedding, wherein the spraying granulation conditions are as follows: the air inlet temperature for drying is 160-190 ℃, the air outlet temperature is 70-90 ℃, the air bottom temperature is 70-85 ℃, and the starch dosage is 24% of the final product quality, thus obtaining the low-odor water-soluble copper chlorophyll.
Example 2
(1) Deodorizing: 2500g of pasty copper chlorophyll with the color value of E82 are weighed and added into a reaction kettle with a stirrer, warm water with the temperature of 45-50 ℃ is introduced into an interlayer of the reaction kettle for circularly heating for 60min, 8700g of 95 percent ethanol with the volume percent is added when materials are in a better flowing state, and the materials are stirred uniformly; slowly adding 230g of ethylene diamine tetraacetic acid disodium solution with the mass percent of 10%, and continuing to keep the temperature and stir for 50min; separating supernatant and precipitate with a sedimentation type three-foot centrifuge (rotational speed 1500r.pm, centrifuging for 25 min), and completing the first cleaning; adding the collected precipitate into a reaction kettle, continuously adding 8700g of ethanol with the volume percentage of 95% and stirring uniformly, slowly adding 230g of ethylene diamine tetraacetic acid disodium solution with the mass percentage of 10%, continuously preserving heat and stirring for 40min, and separating the supernatant and the precipitate by a sedimentation type tripodia centrifuge (the rotating speed is 1500rpm and the centrifuging speed is 20 min) to finish the second cleaning; repeating the washing for 3 times according to the operation;
(2) Concentrating: concentrating the supernatant (ethanol) collected in the step (1) under reduced pressure, and independently storing for recycling; collecting the precipitate, evaporating to remove residual ethanol to an ethanol residue of less than or equal to 200ppm at 80+ -5deg.C under vacuum degree of-0.09 PMa to obtain 1370g low odor refined copper chlorophyll ointment with color value of E152.6;
(3) Dilution: weighing 1000g of sunflower seed oil, heating to 75-80 ℃, adding the sunflower seed oil into the low-odor refined copper chlorophyll ointment prepared in the step (2), and uniformly stirring to obtain 2370g of low-odor copper chlorophyll raw material with good fluidity, wherein the color value is E86;
(4) Emulsifying and homogenizing: 135g of hydroxypropyl starch, 5g of pullulan, 70g of maltodextrin (DE 20), 25g of white sugar and 2g of tea polyphenol are weighed and dissolved in 200g of deionized water to prepare a water-soluble wall material colloid solution with the wall material weight percentage of 32.03%; weighing 200g of the low-odor chlorophyll copper raw material prepared in the step (3), mixing with the water-soluble wall material colloid solution, and vacuum emulsifying for 35min under the conditions of the pressure of-0.08 MPa and the temperature of 45-50 ℃ until the emulsified feed liquid is uniformly dispersed; and (3) carrying out ultrahigh pressure homogenization on the emulsified feed liquid for 2 times under the pressure of 145Mpa to obtain stable low-odor water-soluble copper chlorophyll emulsion, wherein the test particle size D50 is less than or equal to 500nm.
(5) Secondary microencapsulation: spraying granulation is carried out on the low-odor water-soluble copper chlorophyll emulsion prepared in the step (4), starch is sprayed in the spraying granulation process at the same time for secondary embedding, wherein the spraying granulation conditions are as follows: the air inlet temperature for drying is 160-190 ℃, the air outlet temperature is 70-90 ℃, the air bottom temperature is 70-85 ℃, and the starch dosage is 20% of the final product quality, thus obtaining the low-odor water-soluble copper chlorophyll.
Example 3
(1) Deodorizing: weighing 1500g of pasty copper chlorophyll with a color value of E78, adding the pasty copper chlorophyll into a reaction kettle with a stirrer, introducing warm water with a temperature of 35-40 ℃ into an interlayer of the reaction kettle, circularly heating for 45min, adding 6000g of n-butanol when materials are in a good flowing state, and uniformly stirring; slowly adding 170g of sodium pyrophosphate solution with the mass percent of 7%, and continuously preserving heat and stirring for 25min; separating supernatant and precipitate with a tube centrifuge (rotation speed 13000rpm, centrifugation 15 min), and completing the first cleaning; adding the collected precipitate into a reaction kettle, continuously adding 6000g of n-butanol, uniformly stirring, slowly adding 170g of sodium pyrophosphate solution with the mass percent of 7%, continuously preserving heat and stirring for 25min, and separating the supernatant and the precipitate by a tubular centrifuge (the rotating speed is 13000r.pm and the centrifuging is 15 min) again to finish the second cleaning; repeating the washing for 3 times according to the operation;
(2) Concentrating: concentrating the supernatant (n-butanol) collected in the step (1) under reduced pressure, and independently storing for recycling; collecting precipitate, evaporating to remove residual n-butanol to n-butanol residue of 300ppm or less at 87.5+ -2.5deg.C under vacuum degree of-0.09 PMa to obtain 876g low odor refined copper chlorophyll ointment with color value of E136.1;
(3) Dilution: weighing 624g of corn oil, heating to 65-70 ℃, adding the corn oil into the low-odor refined copper chlorophyll ointment prepared in the step (2), and uniformly stirring to obtain 1500g of low-odor copper chlorophyll raw material with good fluidity, wherein the color value is E78.8;
(4) Emulsifying and homogenizing: 15g of damascena, 100g of Arabic gum, 20g of gamma-cyclodextrin, 40g of maltodextrin (DE 10), 25g of trehalose and 2g of EGCG are weighed and dissolved in 220g of deionized water to prepare a water-soluble wall material colloid solution with 33.18% of wall material colloid mass percent; weighing 200g of the low-odor chlorophyll copper raw material prepared in the step (3), mixing with the water-soluble wall material colloid solution, and vacuum emulsifying for 40min under the conditions of the pressure of-0.08 MPa and the temperature of 45-50 ℃ until the emulsified feed liquid is uniformly dispersed; homogenizing the emulsified feed liquid under ultrahigh pressure of 130Mpa for 2 times to obtain stable low-odor water-soluble copper chlorophyll emulsion, and testing the particle size D50 to be less than or equal to 500nm;
(5) Secondary microencapsulation: spraying granulation is carried out on the low-odor water-soluble copper chlorophyll emulsion prepared in the step (4), and maltodextrin is sprayed in the spraying granulation process for secondary embedding, wherein the spraying granulation conditions are as follows: the inlet air temperature for drying is 160-190 ℃, the outlet air temperature is 70-90 ℃, the bottom air temperature is 70-85 ℃, and the maltodextrin dosage is 20% of the final product quality, thus obtaining the low-odor water-soluble copper chlorophyll.
Comparative example 1
The difference from example 1 is that: sodium hexametaphosphate was not added.
Comparative example 2
The difference from example 2 is that: disodium edetate was not added.
Comparative example 3
The difference from example 3 is that: sodium pyrophosphate was not added.
Effect examples
(1) Color value detection
(1) Precisely weighing 0.1g (accurate to 0.0001 g) of a sample to be measured into a small clean beaker of about 50ml, adding distilled water, carefully stirring with a glass rod, draining with the glass rod after the sample is completely dissolved, slowly transferring the sample into a 100ml volumetric flask (the volumetric flask is firstly rinsed with distilled water before transferring the sample), repeatedly rinsing the beaker with a small amount of distilled water until the sample is clean, injecting the rinsing liquid into the volumetric flask, and then fixing the volume to a scale with distilled water and shaking the volumetric flask uniformly.
(2) Accurately sucking 1ml of the diluent by a 1ml pipette, placing the diluent in a 100ml volumetric flask (the pipette is repeatedly rinsed with the diluent for at least 3 times, the volumetric flask is rinsed with a phosphate buffer solution with pH7.5, the volume of the volumetric flask is fixed to a scale by the phosphate buffer solution with pH7.5, and shaking the volumetric flask uniformly to obtain the test solution; wherein, the preparation of phosphate buffer solution with pH of 7.5: 21 parts of 0.15M disodium hydrogen phosphate (GB 1263-77 analytical grade) are mixed with 4 parts of 0.15M potassium dihydrogen phosphate (GB 1274-77 analytical grade).
(3) The absorbance A of the test solution was measured at 405nm in a spectrophotometer in a 1cm cuvette using pH7.5 phosphate buffer as a reference solution.
(4) Color value calculation:
wherein E: color value, a: absorbance at 405nm, m: sample mass g,100: dilution factor.
(2) Particle size detection
(1) Taking a proper amount of sample to be measured by using a sampling spoon, and putting the sample into a measuring cup;
(2) dripping a proper amount of dispersing agent into the measuring cup, and stirring the suspension by using a glass rod; after the sample is well mixed with the liquid, water is added, typically to a scale of 50 ml.
(3) Placing the measuring cup into an ultrasonic cleaner, enabling the liquid level in the cleaning tank to reach about 1/2 of the total height of the measuring cup, turning on a power supply, and vibrating for about 2min (the vibration time can be long or short according to specific samples; for samples which are easy to sink, the glass rod should be used for stirring the liquid in the cup while vibrating).
(4) And (3) measuring, namely completing the sample testing operation according to a prompting step of a laser particle size analyzer (European and American pearl sea).
TABLE 1 color value and particle size of Low odor Water-soluble copper chlorophyll prepared in examples 1 to 3
Examples Color value Particle size (D50)
Example 1 E30.2 482nm
Example 2 E35.3 368nm
Example 3 E35.6 428nm
(3) Detection of precipitation effect of pH value 3.0 solution
The low odor water-soluble copper chlorophyll prepared in examples 1 to 3 was prepared as a solution having a mass percentage of 0.2% and a pH of 3.0, and then left at room temperature to observe whether precipitation was generated in the solution.
The results show that: the acidic solution prepared by the low-odor water-soluble copper chlorophyll prepared in the examples 1-3 is placed for 4 days at normal temperature, and no precipitate is generated.
(4) Sodium copper chlorophyllin (GB 26406-2011) produced by the prior art in the market and manufactured by different manufacturers is taken as a comparison example, the water solubility, odor and pH value 3.0 solution precipitation effect are compared, the color bleeding condition is observed in the application of jelly, and the quality condition of products of different technologies is observed.
(1) Water solubility: the low odor water-soluble copper chlorophyll and the commercial sodium copper chlorophyll salts (control 1 and control 2) prepared in examples 1 to 3 were prepared as solutions with a mass percentage of 1%, respectively, and the water solubility was observed.
(2) The odor of the low odor water-soluble copper chlorophyll and the commercial sodium copper chlorophyll salts (control 1 and control 2) obtained in examples 1 to 3 were evaluated, respectively.
(3) precipitation effect of solution with pH value of 3.0: the specific method is the same as the above (3);
(4) "bleeding" condition in jelly applications:
(a) Mixing white sugar, citric acid, jelly powder and water in proportion, heating with small fire, stirring and decocting slowly while heating, and decocting to obtain a viscous state; adding pigment dissolved in advance (stirring while adding), stopping heating after stirring, pouring into a mold, and cooling to obtain jelly; the jelly comprises the following components in percentage by mass or in percentage by micrometer: 15% of white granulated sugar, 0.18% of citric acid, 0.55% of jelly powder, 84.27% of water and 0.5% of pigment (sodium copper chlorophyll of comparative example and low-odor water-soluble copper chlorophyll prepared in examples 1-3 are converted into the same pigment content);
(b) Preparing carbonated water (containing the following components in percentage by mass or thousandth of 10% of white sugar, 1.3% of citric acid and 0.35% of sodium citrate), boiling for 2min, and cooling to room temperature to obtain the sugar acid water;
(c) Mixing the jelly formed by cooling in the step (a) and the sugar acid water prepared in the step (b) according to the mass ratio of 1:1, shaking uniformly, sealing, standing in a room temperature environment, observing the color change condition of the upper solution, and recording.
The results are shown in Table 2, and compared with the control 1 and 2, the low-odor water-soluble copper chlorophyll prepared in examples 1-3 has good water solubility and no odor and peculiar smell, and the prepared acidic solution has no sediment after being placed for 4 days at normal temperature; control 1 and control 2 had good water solubility, but had significant odor and odor, and the prepared acidic solution had significant precipitation after standing for 4 days at normal temperature.
In addition, the low-odor water-soluble copper chlorophyll prepared in examples 1-3 has high stability when being applied to jelly products, is not easy to cause problems such as bleeding, and has obvious bleeding phenomenon when being applied to jelly products in comparison with comparison 1 and comparison 2. Among them, fig. 1 is a product display diagram of the application of example 1 and control 1 in jelly-like products, wherein example 1 has no "bleeding" phenomenon, and control 1 has a remarkable "bleeding" phenomenon.
TABLE 2 quality comparison of Low odor Water soluble copper chlorophyll with commercially available sodium copper chlorophyll salt prepared in examples 1-3
Water-solubility Odor of solution pH 3.0 precipitation effect of solution (4 days) "bleeding" condition
Example 1 +++++ / / /
Example 2 +++++ / / /
Example 3 +++++ / / /
Control 1 (commercially available) +++++ ++++ ++++ ++++
Control 2 (commercially available) +++++ +++ +++ +++
Note that: the "+" indicates the quality effect, and the more "+" indicates the "better water solubility", "more pronounced odor", "more precipitate amount", "more pronounced bleeding effect", respectively.
(5) The color values of the low odor purified copper chlorophyll ointments prepared in step (2) of examples 1 to 3 and comparative examples 1 to 3 were measured respectively, and the odors were evaluated.
The results are shown in Table 3, and the refined materials prepared in examples 1-3 have higher color values, which show that the phosphate or disodium ethylenediamine tetraacetate and the like are used as chelating agents, so that copper chlorophyll can be effectively fixed, and small molecular degradation products such as fatty acid degradation products, protein degradation products and the like in the copper chlorophyll raw material can be effectively removed, the process loss in the deodorization process is reduced, and the bad odor and peculiar smell in the products are reduced.
TABLE 3 evaluation of color value and odor of purified materials obtained in examples 1 to 3 and comparative examples 1 to 3
The above examples are preferred embodiments of the present invention, but the embodiments of the present invention are not limited to the above examples, and any other changes, modifications, substitutions, combinations, and simplifications that do not depart from the spirit and principle of the present invention should be made in the equivalent manner, and the embodiments are included in the protection scope of the present invention.

Claims (10)

1. The preparation method of the low-odor water-soluble copper chlorophyll is characterized by comprising the following steps of:
(1) Deodorizing: cleaning pasty copper chlorophyll with alcohol solution containing phosphate or disodium ethylenediamine tetraacetate under stirring, and performing solid-liquid separation to obtain alcohol solution and precipitate;
(2) Concentrating: evaporating and removing residual alcohols in the sediment prepared in the step (1) under a vacuum state to obtain low-odor refined copper chlorophyll ointment;
(3) Dilution: adding vegetable oil to dilute the low-odor refined copper chlorophyll ointment prepared in the step (2) to obtain a low-odor copper chlorophyll raw material, wherein the raw material has good fluidity;
(4) Emulsifying and homogenizing: mixing the low-odor chlorophyll copper raw material prepared in the step (3) with a wall material colloid solution, and then carrying out vacuum high-speed emulsification and ultra-high pressure homogenization to obtain low-odor water-soluble chlorophyll copper emulsion;
(5) Secondary microencapsulation: spraying and granulating the low-odor water-soluble copper chlorophyll emulsion prepared in the step (4), and spraying a coating material in the spraying and granulating process for secondary embedding; finally, drying to obtain low-odor water-soluble copper chlorophyll;
the volume percentage of alcohols in the alcohol solution in the step (1) is 75-100%.
2. The method for preparing low-odor water-soluble copper chlorophyll according to claim 1, characterized in that:
the phosphate in the step (1) is at least one of sodium hexametaphosphate, sodium polyphosphate, sodium pyrophosphate and sodium tripolyphosphate.
3. The method for preparing low-odor water-soluble copper chlorophyll according to claim 1, characterized in that:
the mass percentage of the phosphate or disodium ethylenediamine tetraacetate in the alcohol solution in the step (1) is 0.01-5%.
4. The method for preparing low-odor water-soluble copper chlorophyll according to claim 1, characterized in that:
the alcohol solution in the step (1) is at least one of ethanol, isopropanol and n-butanol.
5. The method for preparing low-odor water-soluble copper chlorophyll according to claim 1, characterized in that:
the cleaning conditions in the step (1) are as follows: stirring at the temperature of 30-50 ℃ for 15-90 min; the cleaning times are 1-5 times.
6. The method for preparing low-odor water-soluble copper chlorophyll according to claim 1, characterized in that:
the mass ratio of the alcohol solution to the pasty copper chlorophyll in the step (1) is (2-6): 1.
7. the method for preparing low-odor water-soluble copper chlorophyll according to claim 1, characterized in that:
the wall material colloid in the step (4) is at least one of sodium starch octenyl succinate, hydroxypropyl starch, acetate starch, carboxymethyl starch, phosphate starch, microporous starch, resistant dextrin, acacia, damascan, xanthan gum, pullulan, fucan, trehalose and lactose.
8. The method for preparing low-odor water-soluble copper chlorophyll according to claim 1, characterized in that:
the coating material in the step (5) is at least one of starch and maltodextrin.
9. A low odor water soluble copper chlorophyll characterized by being prepared by the preparation method of any one of claims 1-8.
10. Use of the low odor water soluble copper chlorophyll of claim 9 in foods, cosmetics, pharmaceuticals.
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