CN108003254A - A kind of preparation method and application of phosphorylation carrageenan oligosaccharide - Google Patents
A kind of preparation method and application of phosphorylation carrageenan oligosaccharide Download PDFInfo
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- CN108003254A CN108003254A CN201711338977.4A CN201711338977A CN108003254A CN 108003254 A CN108003254 A CN 108003254A CN 201711338977 A CN201711338977 A CN 201711338977A CN 108003254 A CN108003254 A CN 108003254A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0036—Galactans; Derivatives thereof
- C08B37/0042—Carragenan or carragen, i.e. D-galactose and 3,6-anhydro-D-galactose, both partially sulfated, e.g. from red algae Chondrus crispus or Gigantia stellata; kappa-Carragenan; iota-Carragenan; lambda-Carragenan; Derivatives thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/36—Freezing; Subsequent thawing; Cooling
- A23L3/37—Freezing; Subsequent thawing; Cooling with addition of or treatment with chemicals
- A23L3/375—Freezing; Subsequent thawing; Cooling with addition of or treatment with chemicals with direct contact between the food and the chemical, e.g. liquid nitrogen, at cryogenic temperature
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/02—Phosphorylation
- C07H1/04—Introducing polyphosphoric acid radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/04—Phosphates; Phosphites; Polyphosphates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0003—General processes for their isolation or fractionation, e.g. purification or extraction from biomass
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- Food Science & Technology (AREA)
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- Polysaccharides And Polysaccharide Derivatives (AREA)
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Abstract
A kind of preparation method and application of phosphorylation carrageenan oligosaccharide, the preparation method are：1）The preparation of phosphorylation agent：By sodium tripolyphosphate and sodium trimetaphosphate mixture after mixing, then it is made into aqueous solution reagent；2）Carrageenan oligosaccharide is added in the prepared phosphorylation agent of the above, fully after dissolving, and adjusts mixed system pH value；3）Mixed system is placed in thermostatic control oscillator vibration after reacting 1-5 h and taken out；4）Into mixed system, 95% ethanol, 20-28h of alcohol precipitation in 4 DEG C of refrigerators is added；8-12min is centrifuged after alcohol precipitation, is dissolved in after taking precipitation in a small amount of distilled water, until can be completely dissolved；It is then transferred in bag filter, dialyses；5）After dialysis, mixed liquor is freeze-dried, obtains phosphorylation carrageenan oligosaccharide sample；The application is：By the synergistic protective effect of carrageenan oligosaccharide+phosphate radical, the freeze proof Water-saving effect of aquatic products is improved；Meanwhile compared to phosphate is used merely, the usage amount of relevant metal ions and phosphate radical can be greatly reduced.
Description
Technical field
The present invention relates to a kind of preparation method and application of phosphorylation carrageenan oligosaccharide, belong to the system of freeze proof water-retaining agent
Standby and applied technical field.
Background technology
Carragheen has stronger water-retaining property, can form protein micelle with protein aggregation, to reduce meat products boiling damage
Lose, so as to improve the stability of product, increase yield rate.Carrageenan oligosaccharide is the catabolite of carragheen, its molecular weight is smaller,
Dissolubility is good, and stability and security make moderate progress, while has the characteristics that sugariness is low, heat is small, in biomedicine field
Show tempting application prospect.
At present, before cold storage for frozen fish is fresh-keeping, phosphate immersion treatment generally is used to ensure the jelly of product
Collection matter；Phosphoric acid salt application cost is relatively low, but it can cause aquatic products bitter taste occur, and phosphorous aquatic products is eaten for a long time
Product, severe patient can cause human body P elements unbalance.
The content of the invention
It is an object of the invention to overcome the shortcomings of the prior art, and provide a kind of preparation method simply, reliably, energy
Freeze proof Water-saving effect is improved, the preparation of relevant metal ions and the phosphorylation carrageenan oligosaccharide of phosphate radical usage amount can be greatly reduced
Method and application.
The purpose of the present invention is by following technical solution to complete, a kind of preparation side of phosphorylation carrageenan oligosaccharide
Method, the preparation method include the following steps：
1）The preparation of phosphorylation agent：According to mass ratio it is 4-8 by sodium tripolyphosphate and sodium trimetaphosphate mixture:1 mixing is equal
After even, then mass concentration is made into as 7-10%（w/v）Aqueous solution reagent；
2）Carrageenan oligosaccharide is added in the prepared phosphorylation agent of the above, it is 1-5% to make its mixed mass concentration
（w/v）, fully after dissolving, it is 7.5-8.5 to adjust mixed system pH；
3）Mixed system is placed in thermostatic control oscillator vibration, 65-75 DEG C of water bath with thermostatic control concussions（Rotating speed）After reacting 1-5 h,
Take out；
4）Into mixed system, add 2-4 times of volumes 95% ethanol in 4 DEG C of refrigerators 20-28h of alcohol precipitation；4500 after alcohol precipitation-
5500r/min centrifuges 8-12min, is dissolved in after taking precipitation in a small amount of distilled water, until can be completely dissolved；It is then transferred to
Analyse in bag, dialyse, replace distilled water at regular intervals, to remove unreacted phosphate ion in mixed system；
5）Dialyse after 45-50h, mixed liquor is freeze-dried, obtain phosphorylation carrageenan oligosaccharide sample.
As preferred：The step 1）In：According to mass ratio it is 6 by sodium tripolyphosphate and sodium trimetaphosphate mixture:1
After mixing, then mass concentration is made into as 9%（w/v）, 200mL aqueous solution reagents；
The step 2）In, mixed mass concentration is 3%（w/v）, it is 8.0 to adjust mixed system pH；
The step 3）In, 70 DEG C of water bath with thermostatic control concussions（Rotating speed）After reacting 3h, take out；
The step 4）In, add 3 times of volumes 95% ethanol in 4 DEG C of refrigerators alcohol precipitation 24h；5000r/min is centrifuged after alcohol precipitation
10min；
The step 5）In, dialyse after 48h, mixed liquor is freeze-dried, obtain phosphorylation carrageenan oligosaccharide sample.
A kind of application of phosphorylation carrageenan oligosaccharide as described above, the phosphorylation carrageenan oligosaccharide are applied to chilled water
In the preprocessing process of product, by the synergistic protective effect of carrageenan oligosaccharide+phosphate radical, freeze proof Water-saving effect is improved；Meanwhile
Compared to phosphate is used merely, the usage amount of relevant metal ions and phosphate radical can be greatly reduced.
As preferred：The phosphorylation carrageenan oligosaccharide application is：
Phosphorylation carrageenan oligosaccharide is configured to 1-5% aqueous solution, it is 8.5-9.5 to adjust pH value；Freezing shrimp meat is immersed in phosphorus
It is acidified in carrageenan oligosaccharide solution, solution is 1 with peeled shrimp volume ratio：3-7, under the conditions of mixing slowly, at a temperature of 4 DEG C soak 8-
After 10h, it is quick-frozen after less than -15 DEG C cold storage to take out progress.
As preferred：The phosphorylation carrageenan oligosaccharide application is：It is water-soluble that phosphorylation carrageenan oligosaccharide is configured to 3%
Liquid, it is 9.0 to adjust pH value；Freezing shrimp meat is immersed in phosphorylation carrageenan oligosaccharide solution, solution is 1 with peeled shrimp volume ratio：
5, under the conditions of mixing slowly, after soaking 9h at a temperature of 4 DEG C, it is quick-frozen after -18 DEG C of cold storage to take out progress.
The main reason for phosphoric acid salt plays a role as freeze proof water-retaining agent includes：It is dense to improve system pH, increase ion
Degree and with metal ion chelant.Wherein, phosphate anion is in freeze proof water retention, the important function of performance；The present invention is with card
It is object to draw glue oligosaccharides, itself can show preferable freeze proof water retention, invention by carrageenan oligosaccharide by carrying out phosphorus
Acidifying, by the synergistic protective effect of carrageenan oligosaccharide+phosphate radical, improves freeze proof Water-saving effect；Meanwhile used compared to simple
Phosphate, can be greatly reduced the usage amount of relevant metal ions and phosphate radical.
The present invention has preparation method simple, reliable, can improve freeze proof Water-saving effect, relevant metal ions can be greatly reduced
And the features such as phosphate radical usage amount.
Embodiment
Below in conjunction with specific embodiment, the present invention will be described in detail：A kind of phosphorylation carragheen of the present invention
The preparation method of oligosaccharides, the preparation method include the following steps：
1）The preparation of phosphorylation agent：According to mass ratio it is 4-8 by sodium tripolyphosphate and sodium trimetaphosphate mixture:1 mixing is equal
After even, then mass concentration is made into as 7-10%（w/v）Aqueous solution reagent；
2）Carrageenan oligosaccharide is added in the prepared phosphorylation agent of the above, it is 1-5% to make its mixed mass concentration
（w/v）, fully after dissolving, it is 7.5-8.5 to adjust mixed system pH；
3）Mixed system is placed in thermostatic control oscillator vibration, 65-75 DEG C of water bath with thermostatic control concussions（Rotating speed）After reacting 1-5 h,
Take out；
4）Into mixed system, add 2-4 times of volumes 95% ethanol in 4 DEG C of refrigerators 20-28h of alcohol precipitation；4500 after alcohol precipitation-
5500r/min centrifuges 8-12min, is dissolved in after taking precipitation in a small amount of distilled water, until can be completely dissolved；It is then transferred to
Analyse in bag, dialyse, replace distilled water at regular intervals, to remove unreacted phosphate ion in mixed system；
5）Dialyse after 45-50h, mixed liquor is freeze-dried, obtain phosphorylation carrageenan oligosaccharide sample.
A kind of application of phosphorylation carrageenan oligosaccharide as described above, the phosphorylation carrageenan oligosaccharide are applied to chilled water
In the preprocessing process of product, by the synergistic protective effect of carrageenan oligosaccharide+phosphate radical, freeze proof Water-saving effect is improved；Meanwhile
Compared to phosphate is used merely, the usage amount of relevant metal ions and phosphate radical can be greatly reduced.
It is as further embodiment：The phosphorylation carrageenan oligosaccharide application is：
Phosphorylation carrageenan oligosaccharide is configured to 1-5% aqueous solution, it is 8.5-9.5 to adjust pH value；Freezing shrimp meat is immersed in phosphorus
It is acidified in carrageenan oligosaccharide solution, solution is 1 with peeled shrimp volume ratio：3-7, under the conditions of mixing slowly, at a temperature of 4 DEG C soak 8-
After 10h, it is quick-frozen after less than -15 DEG C cold storage to take out progress.
Embodiment 1：A kind of preparation method of phosphorylation carrageenan oligosaccharide of the present invention, the preparation method include
Following steps：
1）The preparation of phosphorylation agent：According to mass ratio it is 6 by sodium tripolyphosphate and sodium trimetaphosphate mixture:1 is uniformly mixed
Afterwards, then mass concentration is made into as 9%（w/v）, 200mL aqueous solution reagents；
2）Carrageenan oligosaccharide is added in the prepared phosphorylation agent of the above, it is 3% to make its mixed mass concentration（w/
v）, fully after dissolving, it is 8.0 to adjust mixed system pH；
3）Mixed system is placed in thermostatic control oscillator vibration, 70 DEG C of water bath with thermostatic control concussions（Rotating speed）After reacting 3h, take out；
4）Into mixed system, add 3 times of volumes 95% ethanol in 4 DEG C of refrigerators alcohol precipitation 24h；5000r/min is centrifuged after alcohol precipitation
10min, is dissolved in a small amount of distilled water after taking precipitation, until can be completely dissolved；It is then transferred in bag filter, dialyses,
Distilled water is replaced at regular intervals, to remove unreacted phosphate ion in mixed system；
5）Dialyse after 48h, mixed liquor is freeze-dried, obtain phosphorylation carrageenan oligosaccharide sample.
A kind of application of phosphorylation carrageenan oligosaccharide is：Phosphorylation carrageenan oligosaccharide is configured to 3% aqueous solution, adjusts pH
It is worth for 9.0；Freezing shrimp meat is immersed in phosphorylation carrageenan oligosaccharide solution, solution is 1 with peeled shrimp volume ratio：5, mix slowly
Under the conditions of, after soaking 9h at a temperature of 4 DEG C, it is quick-frozen after -18 DEG C of cold storage to take out progress.
Embodiment 2：A kind of preparation method of phosphorylation carrageenan oligosaccharide of the present invention, the preparation method include
Following steps：
1）The preparation of phosphorylation agent：According to mass ratio it is 4 by sodium tripolyphosphate and sodium trimetaphosphate mixture:1 is uniformly mixed
Afterwards, then mass concentration is made into as 7%（w/v）Aqueous solution reagent；
2）Carrageenan oligosaccharide is added in the prepared phosphorylation agent of the above, it is 1% to make its mixed mass concentration（w/
v）, fully after dissolving, it is 7.5 to adjust mixed system pH；
3）Mixed system is placed in thermostatic control oscillator vibration, 65 DEG C of water bath with thermostatic control concussions（Rotating speed）After reacting 1h, take out；
4）Into mixed system, add 2 times of volumes 95% ethanol in 4 DEG C of refrigerators alcohol precipitation 28h；4500r/min is centrifuged after alcohol precipitation
8min, is dissolved in a small amount of distilled water after taking precipitation, until can be completely dissolved；It is then transferred in bag filter, dialyses, often
Distilled water is replaced every a period of time, to remove unreacted phosphate ion in mixed system；
5）Dialyse after 45h, mixed liquor is freeze-dried, obtain phosphorylation carrageenan oligosaccharide sample.
A kind of application of phosphorylation carrageenan oligosaccharide as described above is：It is water-soluble that phosphorylation carrageenan oligosaccharide is configured to 1%
Liquid, it is 8.5 to adjust pH value；Freezing shrimp meat is immersed in phosphorylation carrageenan oligosaccharide solution, solution is 1 with peeled shrimp volume ratio：
3, under the conditions of mixing slowly, after soaking 8h at a temperature of 4 DEG C, it is quick-frozen after -15 DEG C of cold storage to take out progress.
Embodiment 3：A kind of preparation method of phosphorylation carrageenan oligosaccharide of the present invention, the preparation method include
Following steps：
1）The preparation of phosphorylation agent：According to mass ratio it is 8 by sodium tripolyphosphate and sodium trimetaphosphate mixture:1 is uniformly mixed
Afterwards, then mass concentration is made into as 10%（w/v）Aqueous solution reagent；
2）Carrageenan oligosaccharide is added in the prepared phosphorylation agent of the above, it is 5% to make its mixed mass concentration（w/
v）, fully after dissolving, it is 8.5 to adjust mixed system pH；
3）Mixed system is placed in thermostatic control oscillator vibration, 75 DEG C of water bath with thermostatic control concussions（Rotating speed）After reacting 5h, take out；
4）Into mixed system, add 4 times of volumes 95% ethanol in 4 DEG C of refrigerators alcohol precipitation 28h；5500r/min is centrifuged after alcohol precipitation
12min, is dissolved in a small amount of distilled water after taking precipitation, until can be completely dissolved；It is then transferred in bag filter, dialyses,
Distilled water is replaced at regular intervals, to remove unreacted phosphate ion in mixed system；
5）Dialyse after 50h, mixed liquor is freeze-dried, obtain phosphorylation carrageenan oligosaccharide sample.
A kind of application of phosphorylation carrageenan oligosaccharide as described above is：
Phosphorylation carrageenan oligosaccharide is configured to 5% aqueous solution, it is 9.5 to adjust pH value；Freezing shrimp meat is immersed in phosphorylation OK a karaoke club
In glue oligosaccharide solution, solution is 1 with peeled shrimp volume ratio：7, under the conditions of mixing slowly, after soaking 10h at a temperature of 4 DEG C, take out and carry out
It is quick-frozen after -20 DEG C of cold storage.
Claims (5)
1. a kind of preparation method of phosphorylation carrageenan oligosaccharide, it is characterised in that the preparation method includes the following steps：
1）The preparation of phosphorylation agent：According to mass ratio it is 4-8 by sodium tripolyphosphate and sodium trimetaphosphate mixture:1 mixing is equal
After even, then mass concentration is made into as 7-10%（w/v）Aqueous solution reagent；
2）Carrageenan oligosaccharide is added in the prepared phosphorylation agent of the above, it is 1-5% to make its mixed mass concentration
（w/v）, fully after dissolving, it is 7.5-8.5 to adjust mixed system pH；
3）Mixed system is placed in thermostatic control oscillator vibration, 65-75 DEG C of water bath with thermostatic control concussions（Rotating speed）After reacting 1-5 h,
Take out；
4）Into mixed system, add 2-4 times of volumes 95% ethanol in 4 DEG C of refrigerators 20-28h of alcohol precipitation；4500 after alcohol precipitation-
5500r/min centrifuges 8-12min, is dissolved in after taking precipitation in a small amount of distilled water, until can be completely dissolved；It is then transferred to
Analyse in bag, dialyse, replace distilled water at regular intervals, to remove unreacted phosphate ion in mixed system；
5）Dialyse after 45-50h, mixed liquor is freeze-dried, obtain phosphorylation carrageenan oligosaccharide sample.
2. the preparation method of phosphorylation carrageenan oligosaccharide according to claim 1, it is characterised in that：
The step 1）In：According to mass ratio it is 6 by sodium tripolyphosphate and sodium trimetaphosphate mixture:1 after mixing, then
Mass concentration is made into as 9%（w/v）, 200mL aqueous solution reagents；
The step 2）In, mixed mass concentration is 3%（w/v）, it is 8.0 to adjust mixed system pH；
The step 3）In, 70 DEG C of water bath with thermostatic control concussions（Rotating speed）After reacting 3h, take out；
The step 4）In, add 3 times of volumes 95% ethanol in 4 DEG C of refrigerators alcohol precipitation 24h；5000r/min is centrifuged after alcohol precipitation
10min；
The step 5）In, dialyse after 48h, mixed liquor is freeze-dried, obtain phosphorylation carrageenan oligosaccharide sample.
A kind of 3. application of phosphorylation carrageenan oligosaccharide as claimed in claim 1 or 2, it is characterised in that the phosphorylation OK a karaoke club
Glue oligosaccharides is applied in the preprocessing process of frozen fish, by the synergistic protective effect of carrageenan oligosaccharide+phosphate radical, improves
Freeze proof Water-saving effect；Meanwhile compared to phosphate is used merely, the use of relevant metal ions and phosphate radical can be greatly reduced
Amount.
4. the application of phosphorylation carrageenan oligosaccharide according to claim 3, it is characterised in that the phosphorylation carragheen
Oligosaccharides application is：
Phosphorylation carrageenan oligosaccharide is configured to 1-5% aqueous solution, it is 8.5-9.5 to adjust pH value；Freezing shrimp meat is immersed in phosphorus
It is acidified in carrageenan oligosaccharide solution, solution is 1 with peeled shrimp volume ratio：3-7, under the conditions of mixing slowly, at a temperature of 4 DEG C soak 8-
After 10h, it is quick-frozen after less than -15 DEG C cold storage to take out progress.
5. the application of phosphorylation carrageenan oligosaccharide according to claim 4, it is characterised in that the phosphorylation carragheen
Oligosaccharides application is：Phosphorylation carrageenan oligosaccharide is configured to 3% aqueous solution, it is 9.0 to adjust pH value；Freezing shrimp meat is immersed in phosphorus
It is acidified in carrageenan oligosaccharide solution, solution is 1 with peeled shrimp volume ratio：5, under the conditions of mixing slowly, after soaking 9h at a temperature of 4 DEG C,
It is quick-frozen after -18 DEG C of cold storage to take out progress.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109265572A (en) * | 2018-09-21 | 2019-01-25 | 湖南大学 | A kind of phosphorylation polyhydroxy high-molecular compound and its synthetic method |
| CN109438530A (en) * | 2018-12-01 | 2019-03-08 | 浙江海洋大学 | A kind of preparation method of phosphorylation maltose |
| CN109601598A (en) * | 2018-12-27 | 2019-04-12 | 青岛中信源食品科技有限公司 | A kind of without phosphorus squid water-retaining agent and its application |
| CN109619163A (en) * | 2018-12-01 | 2019-04-16 | 浙江海洋大学 | A kind of production method of seeweed polyphenol-carrageenan oligosaccharide compound |
| CN109651454A (en) * | 2018-12-01 | 2019-04-19 | 浙江海洋大学 | A kind of preparation method of phosphorylation cellobiose |
| CN113817020A (en) * | 2021-10-18 | 2021-12-21 | 浙江海洋大学 | Method for preparing protein from boiled red shrimp wastewater |
| CN114586831A (en) * | 2022-03-01 | 2022-06-07 | 福建农林大学 | Phosphorylated nano chitin antifreeze agent and preparation method thereof |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109265572A (en) * | 2018-09-21 | 2019-01-25 | 湖南大学 | A kind of phosphorylation polyhydroxy high-molecular compound and its synthetic method |
| CN109438530A (en) * | 2018-12-01 | 2019-03-08 | 浙江海洋大学 | A kind of preparation method of phosphorylation maltose |
| CN109619163A (en) * | 2018-12-01 | 2019-04-16 | 浙江海洋大学 | A kind of production method of seeweed polyphenol-carrageenan oligosaccharide compound |
| CN109651454A (en) * | 2018-12-01 | 2019-04-19 | 浙江海洋大学 | A kind of preparation method of phosphorylation cellobiose |
| CN109601598A (en) * | 2018-12-27 | 2019-04-12 | 青岛中信源食品科技有限公司 | A kind of without phosphorus squid water-retaining agent and its application |
| CN113817020A (en) * | 2021-10-18 | 2021-12-21 | 浙江海洋大学 | Method for preparing protein from boiled red shrimp wastewater |
| CN114586831A (en) * | 2022-03-01 | 2022-06-07 | 福建农林大学 | Phosphorylated nano chitin antifreeze agent and preparation method thereof |
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