CN112473181A - Method for removing odor of biological extract - Google Patents
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Abstract
The invention provides a method for removing the peculiar smell of a biological extract. The method comprises the following steps: the first step is as follows: dissolving the biological extract with a certain volume of solvent to obtain a biological extract solution; the second step is that: and (3) performing deodorization treatment on the biological extract solution obtained in the first step by using a multifunctional silica gel solid acid adsorbent and a multifunctional silica gel adsorbent solid base adsorbent respectively. The multifunctional silica gel solid acid and solid base adsorbent are used together, and can adsorb complex and various peculiar smell components, so that the effect of fundamentally eliminating peculiar smell is achieved, the sensory property of the extract is improved, the loss of nutrition of the extract is reduced, and the safety of the extract as food is ensured.
Description
Technical Field
The invention relates to a method for removing the peculiar smell of a biological extract.
Background
The biological extracts are mainly divided into plant extracts and animal extracts. The plant extract is a product formed by taking plants (including tissues, fruits and the like) as raw materials and directionally obtaining and concentrating one or more active ingredients in the plants through a physical and chemical extraction and separation process without changing the effective ingredient polarity. The animal extract is prepared by taking an animal body, part of animal body tissues or viscera as raw materials, extracting by mild biological enzymolysis or decocting, then concentrating, and spray drying to obtain the meat extract, is a new industry corresponding to plant extracts, and is generally called as biochemical products and biochemical raw material medicines in the past. The main classes of the compounds are amino acids, peptides, proteins, enzymes and coenzymes, polysaccharides, lipids, nucleic acids and derivatives thereof.
The biological extract has been deeply applied to various fields of life of people, can be used as a raw material or an auxiliary material, and is widely applied to downstream industries such as food and beverage, medicines, health care products, cosmetics and the like. With the improvement of life quality, people put forward higher requirements on biological extracts and products thereof, and under the premise that some basic conditions reach the standard, for example, the heavy metal content must meet the national standard, and the requirements on the quality (such as color, smell and the like) of the biological extracts and the products thereof are higher and higher. Products with peculiar smell directly affect the acceptance degree of consumers, so that the peculiar smell removal is an essential step in the industries of food, beverage, medicine, health care products, cosmetics and the like.
The method for removing the peculiar smell of the biological extract mainly comprises the methods of reduced pressure and high temperature distillation or adding chemical reagents and the like. The main problems of reduced pressure and high temperature distillation are that the process is complicated, the required time is long, the energy consumption is high, the nutrient structure of the aquatic organism extract is damaged, and even toxic substances are generated; the addition of some chemical agents limits the application range of the processed biological extract; and because the original substances generating the peculiar smell are not fundamentally eliminated by a plurality of methods, the peculiar smell reappears in the storage process of the product, and the like. Chinese patent (publication No. CN108913352A) discloses a deaminized low-fishy-smell krill oil and a preparation method thereof, and mentions that the odor of the krill oil is reduced by resin adsorption, but only part of the single fishy-smell substances are used. The main components of the peculiar smell generated by the biological extract are complex and various, and no report is found for removing the complex and various peculiar smell components at present.
The multifunctional silica gel solid acid and solid base adsorbent are used together, and can adsorb complex and various peculiar smell components, so that the effect of fundamentally eliminating peculiar smell is achieved, the sensory property of the extract is improved, the loss of nutrition of the extract is reduced, and the safety of the extract as food is ensured.
Disclosure of Invention
The invention aims to provide a method for removing the peculiar smell of a biological extract. It can achieve the effect of fundamentally eliminating peculiar smell.
The technical scheme provided by the invention for solving the technical problems is as follows:
a method for deodorizing a biological extract is provided, comprising the steps of:
the first step is as follows: dissolving the biological extract with a certain volume of solvent to obtain a biological extract solution;
the second step is that: and (3) performing deodorization treatment on the biological extract solution obtained in the first step by using a multifunctional silica gel solid acid adsorbent and a multifunctional silica gel adsorbent solid base adsorbent respectively.
According to the scheme, the general formula of the multifunctional silica gel solid acid adsorbent is as follows:
[(O3/2)Si(CH2)xT]a[Si(O4/2)]b[(CH2)uWSi(O3/2)]c[VSi(O3/2)]d III
t is selected from P (═ O) (OM)2，P(＝O)H(OM)；S(CH2)3SO3M；COOM。
M is H, alkali metal, alkaline earth metal. Wherein x is an integer from 2 to 12; u is an integer from 2 to 12; w is SH or S (CH)2)vSH, v are integers from 2 to 6; v is selected from C1-22Alkyl radical, C1-22Alkyl aryl, C2-20Alkyl sulfide radical, C1-12Alkyl radical, C2-20Alkylene thioether alkyl, C2-20-Alkyl thioether aryl, C2-20-an alkylene thioether aryl group; a, b, c, d are integers, and a + c + d: the ratio of b is between 0.000001 and 100, both a and b are always present, and when either c or d or both are greater than zero, the ratio of c + d to a + b is between 0.000001 and 100.
The general formula of the multifunctional silica gel solid base adsorbent is as follows:
[(O3/2)Si(CH2)xT]a[Si(O4/2)]b[(CH2)uWSi(O3/2)]c[VSi(O3/2)]d IV
t is selected from S (CH)2)yNH(CH2CH2NH)zH,-NH(CH2CH2NH)zH; a compound of the general formula II.
R0Is hydrogen, C1-22An alkyl or aryl group; n is an integer from 1 to 100; l is1Is an anion including, but not limited to, halides, nitrates, sulfates, carbonates, phosphates, chromates, potassium permanganate, sodium borohydride, substituted borohydrides such as cyano-substituted borohydrides; wherein x is an integer from 2 to 12; y is an integer from 3 to 12; z is an integer from 0 to 100; u is an integer from 2 to 12; w is SH or S (CH)2)vSH, v are integers from 2 to 6; v is selected from C1-22Alkyl radical, C1-22Alkyl aryl, C2-20Alkyl sulfide radical, C1-12Alkyl radical, C2-20Alkylene thioether alkyl, C2-20-Alkyl thioether aryl, C2-20-an alkylene thioether aryl group; a, b, c, d are integers, and a + c + d: the ratio of b is between 0.000001 and 100, both a and b are always present, and when either c or d or both are greater than zero, the ratio of c + d to a + b is between 0.000001 and 100.
According to the scheme, the solvent used in the first step is selected from ethyl acetate, acetone, ethanol and water, and the volume ratio of the mass of the biological extract to the solvent is 1: 1-100.
According to the scheme, the peculiar smell treatment in the second step and the third step is a slurry mode (stirring and filtering in a reaction kettle) or a fixed bed mode (chromatography columns are connected in series or in parallel for passing through the columns), the treatment time is 15min-48h, the treatment temperature is 20-100 ℃, and the volume ratio of the mass of the adsorbent to the volume of the biological extract solution is 0.1:0.1-100 g/mL. The slurry mode is that an adsorbent is added into a system, and the system is stirred, adsorbed and filtered; the fixed bed mode is as follows: the adsorbent is fixed on a fixed bed or an adsorption column, and then a system to be treated flows through a chromatographic column fixed with the adsorbent for adsorption treatment, and the chromatographic columns are connected in series or in parallel to pass through the column.
According to the scheme, the biological extract is plant (such as seaweed, kelp, houttuynia cordata and beans) extract, animal (such as chicken, duck, cattle, sheep, rabbit and seafood) extract and fungus (such as mushroom) extract.
According to the scheme, the plant extract comprises vegetable oil and vegetable protein; the animal extract comprises animal protein and protein peptide, animal oil (such as fish oil, alligator oil, shrimp oil, mussel oil, crab oil, oyster oil); the fungus extract comprises extract of mushroom (such as Agaricus campestris and Lentinus Edodes).
The above biological extract has peculiar smell of fishy smell and self-offensive smell, and has complex and various components, mainly including terpene compounds and their derivatives, amine compounds and their derivatives, pyridine compounds and their derivatives, aldehyde compounds and their derivatives, ketone compounds and their derivatives, and carboxylic acid compounds and their derivatives.
The invention has the beneficial effects that:
the method for removing the peculiar smell provided by the invention uses the multifunctional silica gel solid acid and the solid base adsorbent together, and can adsorb complex and various peculiar smell components, thereby achieving the effect of fundamentally removing the peculiar smell, improving the sensory property of the extract, reducing the loss of the nutrition of the extract and ensuring the safety of the extract as food.
Detailed Description
For the sake of understanding, the present invention will be described in detail below by way of specific examples. It is to be expressly understood that the description is illustrative only and is not intended as a definition of the limits of the invention. Many variations and modifications of the present invention will be apparent to those skilled in the art in light of the teachings of this specification.
Example 1
Silica gel (37-500 μm,
20kg) and water (42L) were mixed with stirring at 100 ℃ and vinyltrimethoxysilane (16mol) was added and the reaction mixture was heated and stirred for 5 h. After cooling, the solid was filtered, washed thoroughly with water and dried to give a vinyl silica gel solid. A50L reactor was charged with phosphorous acid (3280g,40mol) and RO (10L) water with stirring, charged with the above vinyl silica gel (1.4-2.0mmol/g, 4.0kg,) and chargedTert-butyl hydroperoxide (40ml), stirring for 40min at room temperature, then heating, setting the oil bath at 130 deg.C, starting the addition of tert-butyl hydroperoxide at 8 ml/15 min when the temperature of the oil bath is reached and there is reflux of liquid, removing the liquid after cooling, adding water (30L) to the solid, stirring for 30min, and filtering. More water (30L) was added to the solid and the mixture was stirred for 30min and filtered. This procedure was repeated 3 more times and dried to give a fraction of formula I, wherein T is P (═ O) (OM)2M is H; x is 3; the integer c is 0 and the integer d is 0. [ Multifuntionalized silica gel solid acid adsorbent A]
Example 2
A50L reactor was charged with tetraethylenepentamine (6840g,36mol) and (CH)3O)3Si(CH2)3S(CH2)3Cl (24mol), stirring at 130 deg.C, heating for 5 hr, cooling to 70 deg.C, adding ethanol (5000mL), refluxing for 2 hr until the liquid becomes transparent, cooling, transferring to a 100L reactor, adding heptane (40.0L) and silica gel (16.0kg,37-500 μm,
) The temperature of the oil bath kettle is set at 130 ℃, when the temperature of the oil bath kettle reaches the set value, the collection of ethanol is started, and the whole process lasts for 3 hours. After 3-mercaptopropyltrimethoxysilane (3436mL,18mol) was added, heating was continued for 5 hours and cooling was carried out. The liquid was removed and the solid was stirred with water (100L) for 30min and filtered. More water (100L) was added to the solid and the mixture was stirred for 30min and filtered. This process was repeated 3 more times and dried to form a fraction of formula I wherein T is S (CH)2)yNH(CH2CH2NH)zH; x is 3; y is 3, z is 4; w is SH, u is 3, and d is 0. [ Multifuntionalized silica gel solid acid adsorbent B]
Example 3
Adding 250ml of absolute ethyl alcohol into 25g of kelp extract products, and fully stirring until the absolute ethyl alcohol is dissolved to obtain a solution A; adding 10g of the adsorbent in the example 1 into the solution A, stirring the mixture at 40 ℃ for 2h, filtering the mixture, washing the adsorbent with 50ml of absolute ethyl alcohol, repeating the operation for three times, mixing a washing solution with a filtrate, and carrying out rotary evaporation at 60 ℃ until the volume of the solution is 250ml to obtain a solution B; 10g of the adsorbent according to example 2 was added to the solution B obtained above, the mixture was stirred at 40 ℃ for 2 hours, then filtered, and the adsorbent was washed with 50ml of absolute ethanol, and the process was repeated three times, and the washing solution was mixed with the filtrate and rotary evaporated at 60 ℃ until ethanol was completely evaporated.
Example 4
Taking 25g of crude shrimp sauce product, adding 250ml of absolute ethyl alcohol, and fully stirring until the solution is dissolved to obtain solution A1; adding 12.5g of the adsorbent in example 1 into the solution A1, stirring for 4h at 25 ℃, filtering, washing the adsorbent with 50ml of absolute ethyl alcohol, repeating for three times, mixing the washing solution with the filtrate, and performing rotary evaporation at 60 ℃ until the volume of the solution is 250ml to obtain a solution B1; 12.5g of the adsorbent of example 2 was added to the solution B1, the mixture was stirred at 25 ℃ for 4 hours, filtered, washed with 50ml of absolute ethanol and repeated three times, and the washing solution and the filtrate were mixed and evaporated at 60 ℃ until ethanol was completely evaporated.
Example 5
Taking 100ml of the mushroom and yellow rice head extract, adding 10g of the adsorbent in the embodiment 1, stirring for 4h at 40 ℃, filtering, adding 10g of the adsorbent in the embodiment 2 into the filtrate, stirring for 4h at 25 ℃, and filtering to obtain the product.
Example 6
Detection of
The volatile gas in the kelp extract product in example 3 was analyzed by means of gas chromatography-mass spectrometry (GC-MS), and it was finally determined that the kelp volatile gas components contained alcohols, aldehydes, ketones, carboxylic acids, alkanes, alkenes and their derivatives, aromatics, esters, and the like. The main substances playing a role in the fishy smell are aldehydes and ketones.
The relative content of main fishy smell volatile components in the kelp extract product before and after treatment is changed:
TABLE 1
| Volatile ingredient name | Relative content before deodorization% | The relative content after deodorization |
| Octanal | 3.87 | 0.43 |
| (trans) 2-octenal | 8.69 | Not detected out |
| Nonanal | 6.53 | 0.77 |
| Decanal | 2.92 | 0.36 |
| 1-hepten-3-ones | 7.87 | 0.28 |
| 1, 4-dien-3-ones | 6.49 | 0.22 |
As shown in table 1:
comparing the volatile components of the kelp extract product with the volatile components of the processed kelp extract product, the main fishy smell substances are reduced to very low content.
Example 7
The kelp extract product treated in example 3 was tested by actual use of monitoring personnel to evaluate the fishy smell removing effect
The test method comprises the following steps:
18 professionals were randomly selected as panelists, and the kelp extract preparation treated in example 3 was applied to the backs of hands of the panelists, followed by smelling the taste thereof and measuring by sensory measurement.
The fishy smell removing effect is evaluated according to 3 grades, wherein A is basically free of fishy smell B, C is very light in fishy smell and C is relatively strong in fishy smell.
| Evaluation item | A | B | C |
| Results | 17 | 1 | 0 |
The processed kelp extract product has no unpleasant fishy smell from smell.
Example 8
Detection of
The peculiar smell or fishy smell substances in the shrimp sauce obtained in example 4 were analyzed, and the volatile components before and after the treatment were compared, and as a result, the fishy smell substances in the shrimp sauce were found to be mainly trimethylamine, trimethylamine oxide, aldehydes and ketone organic components.
The phospholipid content, astaxanthin content, EPA content, DHA content, trimethylamine nitrogen oxide content and the relative aldehyde ketone content (GC-MS) in the volatile gas in the shrimp oil before and after the treatment were as follows:
TABLE 2
As shown in table 2:
compared with the analysis result of the volatile components of the prawn oil and the volatile components of the processed prawn oil, the loss rate of the nutrient components is not more than 10%, the content of main fishy smell components, namely amine, is reduced by more than 98%, and the relative content of aldehyde and ketone is reduced by more than 85%.
Example 9
The shrimp sauce treated in example 4 was tested to evaluate the deodorizing effect by monitoring the actual use of the persons.
The test method comprises the following steps:
18 professionals were randomly selected as panelists, and the shrimp sauce treated in example 4 was applied to the backs of hands of the panelists, followed by smelling the oil and measuring the oil by sensory perception.
The fishy smell removing effect is evaluated according to 3 grades, wherein A is basically no fishy smell B, light fishy smell C and strong fishy smell.
| Evaluation item | A | B | C |
| Results | 15 | 3 | 0 |
The processed shrimp sauce has no unpleasant fishy smell from smell.
Example 10
Detection of
The odor or fishy smell substances in the mushroom yellow rice head extracting solution in the example 5 are analyzed, and the volatile components before and after the treatment are compared, so that the fishy smell substances in the mushroom yellow rice head extracting solution are mainly furfural, nonanal, hexanal, 1-octen-3-one and 3-methyl butyraldehyde.
TABLE 3
As shown in table 3:
the analysis result of the volatile components in the mushroom yellow rice wine head extracting solution and the volatile components in the processed mushroom yellow rice wine head extracting solution is compared, so that the main fishy smell substances are reduced to very low content.
Example 11
The extract of the treated mushroom of example 5 was tested to evaluate the deodorizing effect by the actual use of the monitoring person.
The test method comprises the following steps:
18 professionals were randomly selected as panelists, and the panelists of the extract of the treated mushroom flavedo head of example 4 were applied to the backs of hands, allowed to smell the taste thereof, and measured by sensory evaluation.
The fishy smell removing effect is evaluated according to 3 grades, wherein A is basically no fishy smell B, light fishy smell C and strong fishy smell.
| Evaluation item | A | B | C |
| Results | 18 | 0 | 0 |
The processed mushroom and yellow rice head extract has no unpleasant fishy smell from smell.
The above examples are only for illustrating the technical idea and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the content of the present invention and implement the present invention, and not to limit the protection scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (8)
1. The method for removing the peculiar smell of the biological extract is characterized by comprising the following steps: the method comprises the following steps:
the first step is as follows: dissolving the biological extract with a certain volume of solvent to obtain a biological extract solution;
the second step is that: and (3) performing deodorization treatment on the biological extract solution obtained in the first step by using a multifunctional silica gel solid acid adsorbent and a multifunctional silica gel adsorbent solid base adsorbent respectively.
2. The method of claim 1, wherein: the general formula of the multifunctional silica gel solid acid adsorbent is as follows: [ (O)3/2)Si(CH2)xT]a[Si(O4/2)]b[(CH2)uWSi(O3/2)]c[VSi(O3/2)]d III，
T is selected from P (═ O) (OM)2，P(＝O)H(OM)；S(CH2)3SO3M；COOM，
M is H, alkali metal, alkaline earth metal. Wherein x is an integer from 2 to 12; u is an integer from 2 to 12; w is SH or S (CH)2)vSH, v are integers from 2 to 6; v is selected from C1-22Alkyl radical, C1-22Alkyl aryl, C2-20Alkyl sulfide radical, C1-12Alkyl radical, C2-20Alkylene thioether alkyl, C2-20-Alkyl thioether aryl, C2-20-an alkylene thioether aryl group; a, b, c, d are integers, and a + c + d: the ratio of b is between 0.000001 and 100, both a and b are always present, and when either c or d or both are greater than zero, the ratio of c + d to a + b is between 0.000001 and 100.
3. The method of claim 1, wherein: the general formula of the multifunctional silica gel solid base adsorbent is as follows: [ (O)3/2)Si(CH2)xT]a[Si(O4/2)]b[(CH2)uWSi(O3/2)]c[VSi(O3/2)]d IV，
T is selected from S (CH)2)yNH(CH2CH2NH)zH,-NH(CH2CH2NH)zH; a compound of the general formula II,
R0is hydrogen, C1-22An alkyl or aryl group; n is an integer from 1 to 100; l is1Is an anion including, but not limited to, halides, nitrates, sulfates, carbonates, phosphates, chromates, potassium permanganate, sodium borohydride, substituted borohydrides such as cyano-substituted borohydrides; wherein x is an integer from 2 to 12; y is an integer from 3 to 12; z is an integer from 0 to 100; u is an integer from 2 to 12; w is SH or S (CH)2)vSH, v are integers from 2 to 6; v is selected from C1-22Alkyl radical, C1-22Alkyl aryl, C2-20Alkyl sulfide radical, C1-12Alkyl radical, C2-20Alkylene thioether alkyl, C2-20-Alkyl thioether aryl, C2-20-an alkylene thioether aryl group; a, b, c, d are integers, and a + c + d: the ratio of b is between 0.000001 and 100, both a and b are always present, and when either c or d or both are greater than zero, the ratio of c + d to a + b is between 0.000001 and 100.
4. The method of claim 1, wherein: the solvent used in the first step is selected from ethyl acetate, acetone, ethanol and water; the volume ratio of the mass of the biological extract to the solvent is 1: 1-100.
5. The method of claim 1, wherein: in the second step and the third step, the peculiar smell treatment is in a slurry mode or a fixed bed mode, the treatment time is 15min-48h, the treatment temperature is 20-100 ℃, and the volume ratio of the mass of the adsorbent to the volume of the biological extract solution is 0.1:0.1-100 g/mL; the slurry mode is that an adsorbent is added into a biological extract solution system, and the mixture is stirred, adsorbed and filtered; the fixed bed mode is as follows: the adsorbent is fixed on a fixed bed or an adsorption column, and then a system to be treated flows through a chromatographic column fixed with the adsorbent for adsorption treatment, and the chromatographic columns are connected in series or in parallel to pass through the column.
6. The method of claim 1, wherein: the biological extract is plant extract, animal extract or fungus extract.
7. The method of claim 6, wherein: the plant extract is extracts of seaweed, kelp, houttuynia cordata and beans, the animal extract is extracts of chicken, duck, cattle, sheep, rabbit and seafood, and the fungus extract is an extract of mushroom.
8. The method of claim 6, wherein: the plant extract comprises vegetable oil and vegetable protein; the animal extract comprises animal protein and protein peptide, and animal oil, wherein the animal oil comprises fish oil, alligator oil, shrimp oil, mussel oil, crab oil, and oyster sauce; the fungus extract comprises a mushroom extract.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114653345A (en) * | 2022-05-24 | 2022-06-24 | 苏州硒诺唯新新材料科技有限公司 | Functional silica gel material and preparation method and application thereof |
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| CN111939875A (en) * | 2020-07-20 | 2020-11-17 | 杨南超 | Targeted silica gel material adsorbent and application thereof |
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| US4877765A (en) * | 1987-05-15 | 1989-10-31 | W. R. Grace & Co. | Adsorptive material for the removal of chlorophyll, color bodies and phospholipids from glyceride oils |
| US20060165737A1 (en) * | 2003-01-22 | 2006-07-27 | Christiane Richard-Elsner | Reducing the odor of oil components by means of adsorption with polymeric adsorbing agents |
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| CN114653345A (en) * | 2022-05-24 | 2022-06-24 | 苏州硒诺唯新新材料科技有限公司 | Functional silica gel material and preparation method and application thereof |
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