CN110063359A - A kind of preparation method and application of biology crude antistaling agent - Google Patents
A kind of preparation method and application of biology crude antistaling agent Download PDFInfo
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- CN110063359A CN110063359A CN201910312357.6A CN201910312357A CN110063359A CN 110063359 A CN110063359 A CN 110063359A CN 201910312357 A CN201910312357 A CN 201910312357A CN 110063359 A CN110063359 A CN 110063359A
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- China
- Prior art keywords
- antistaling agent
- octyl gallate
- preparation
- crude antistaling
- cyclodextrin
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- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 47
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims abstract description 33
- 238000003860 storage Methods 0.000 claims abstract description 32
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims abstract description 22
- NRPKURNSADTHLJ-UHFFFAOYSA-N octyl gallate Chemical compound CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1 NRPKURNSADTHLJ-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000000574 octyl gallate Substances 0.000 claims abstract description 21
- 235000010387 octyl gallate Nutrition 0.000 claims abstract description 21
- 241000881711 Acipenser sturio Species 0.000 claims abstract description 20
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 239000001116 FEMA 4028 Substances 0.000 claims abstract description 14
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims abstract description 14
- 229960004853 betadex Drugs 0.000 claims abstract description 14
- 238000002844 melting Methods 0.000 claims abstract description 13
- 230000008018 melting Effects 0.000 claims abstract description 13
- 238000006911 enzymatic reaction Methods 0.000 claims abstract description 8
- 238000005538 encapsulation Methods 0.000 claims abstract 2
- 239000000047 product Substances 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 9
- 238000004108 freeze drying Methods 0.000 claims description 9
- 235000019441 ethanol Nutrition 0.000 claims description 7
- 238000013019 agitation Methods 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 4
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 3
- 229960004373 acetylcholine Drugs 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- LEXBBZCFWJNTGC-UHFFFAOYSA-N gallicin Natural products C1CC(=C)C(O)CCC(C)=CC2OC(=O)C(C)C21 LEXBBZCFWJNTGC-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 238000005809 transesterification reaction Methods 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 239000012043 crude product Substances 0.000 claims description 2
- 230000006837 decompression Effects 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000706 filtrate Substances 0.000 claims 1
- 230000008595 infiltration Effects 0.000 claims 1
- 238000001764 infiltration Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 8
- 235000013305 food Nutrition 0.000 abstract description 4
- 230000003385 bacteriostatic effect Effects 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- 230000009967 tasteless effect Effects 0.000 abstract 1
- 102000002322 Egg Proteins Human genes 0.000 description 13
- 108010000912 Egg Proteins Proteins 0.000 description 13
- 210000004681 ovum Anatomy 0.000 description 13
- 241000251468 Actinopterygii Species 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- 210000001672 ovary Anatomy 0.000 description 8
- 238000011156 evaluation Methods 0.000 description 6
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- 238000002386 leaching Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 230000026109 gonad development Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 230000002045 lasting effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 230000002335 preservative effect Effects 0.000 description 4
- 238000003672 processing method Methods 0.000 description 4
- 238000005057 refrigeration Methods 0.000 description 4
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 4
- 238000007789 sealing Methods 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 238000004659 sterilization and disinfection Methods 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- -1 cyclic oligosaccharides Chemical class 0.000 description 3
- 229960000935 dehydrated alcohol Drugs 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 229940074391 gallic acid Drugs 0.000 description 3
- 235000004515 gallic acid Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004367 Lipase Substances 0.000 description 2
- 102000004882 Lipase Human genes 0.000 description 2
- 108090001060 Lipase Proteins 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 2
- 235000019421 lipase Nutrition 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000019640 taste Nutrition 0.000 description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 108010025880 Cyclomaltodextrin glucanotransferase Proteins 0.000 description 1
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- SBNFWQZLDJGRLK-UHFFFAOYSA-N phenothrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 SBNFWQZLDJGRLK-UHFFFAOYSA-N 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVING, e.g. BY CANNING, MEAT, FISH, EGGS, FRUIT, VEGETABLES, EDIBLE SEEDS; CHEMICAL RIPENING OF FRUIT OR VEGETABLES; THE PRESERVED, RIPENED, OR CANNED PRODUCTS
- A23B4/00—General methods for preserving meat, sausages, fish or fish products
- A23B4/14—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12
- A23B4/18—Preserving with chemicals not covered by groups A23B4/02 or A23B4/12 in the form of liquids or solids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Meat, Egg Or Seafood Products (AREA)
Abstract
The invention discloses a kind of octyl gallate/beta-cyclodextrin encapsulation object crude antistaling agent, it according to molar ratio is that 1:1 carries out encapsulating preparation that wherein octyl gallate, which is by the enzymatic method preparation in depth congruent melting solvent, octyl gallate and beta-cyclodextrin,.Meanwhile also disclose its application in sturgeon caviar is fresh-keeping, efficiently solve the problems, such as caviar storage, present in transportational process it is putrid and deteriorated.For the present invention as crude antistaling agent, component is green safe, tasteless nontoxic, edible, improves the water solubility and bacteriostatic activity of octyl gallate, expand octyl gallate as antistaling agent field of food application range.
Description
Technical field
The present invention relates to the fresh-keeping octyl gallate of food antiseptic/beta-cyclodextrin supermolecule biology crude antistaling agent, tools
Saying for body is a kind of bacteriostatic agent, be specifically for use in preservation of fishery, the especially storage of sturgeon roe jam products with it is fresh-keeping.
Background technique
Caviar (Caviar), also known as caviar, usually sturgeon fish-egg after slight salt marsh made of.Yin Qifeng
The nutritional ingredients such as rich EPA, DHA, EPA and DHA and 3 polyunsaturated fatty acid of ω are usually compared to " black soft gold ".Fish
Luxury goods of the sub- sauce as international market, in recent years in the consumption market also further expansion in China.In addition, caviar exists
The application of health care product and cosmetic field also has been to be concerned by more and more people.
The fresh-keeping of caviar is major issue in production and transport and storage.Prevent at present frequently with a large amount of salt
Corruption, fresh-keeping effect is poor and has a poor flavour, therefore can be applied to the exploitation of the fresh-keeping safe and efficient antiseptics for natural food of caviar
It is received significant attention with application.Octyl gallate (GAC8) is used as antioxidant from natural food, and research finds it in antibacterial side
Face significant effect, but its poor water solubility limits the application in aquatic products field.
Cyclodextrin is that a series of cyclic oligosaccharides caused by amylose are acted on as cyclodextrin glycosyltransferase
General name, common cyclodextrin mainly has 3 kinds, and beta-cyclodextrin (β-CD), alpha-cyclodextrin, gamma-cyclodextrin contain 6,7 and 8 respectively
A glucose unit.It is in " truncated cones " shape in cyclodextrin molecular external form, one end is big, and one end is small, the hydroxyl of glucose unit
Positioned at two edges of truncated cones, and the hydrogen atom on C3 and C5 is located at the internal cavities of truncated cones, therefore cyclodextrin has
The special construction and property of " inner cavity is hydrophobic, and outer wall is hydrophilic " facilitate the dissolubility for improving substance.Wherein beta-cyclodextrin molecule because
Crystal property is well easy to purify, low in cost, is most widely used in similar product at present.
Ionic liquid is more high-performance bio catalysis reaction medium, especially the new function ion of developmental research in recent years
Liquid.The enzymic catalytic reaction in non-aqueous media had both may be implemented in it, realized the safety of solvent-free system, and can be improved anti-
Rate is answered, yield is promoted, realizes the concept of Green Chemistry.
This seminar is fresh-keeping further to prepare GAC8/ β-CD using the GAC8 that the enzymatic method in depth congruent melting solvent obtains
Agent ensure that the safety of this antistaling agent from source.GAC8/ β-CD antistaling agent colorless and odorless, it is highly-safe, both solved
The problem of GAC8 poorly water-soluble, and improve bacteriostatic activity.The appearance and quality of caviar, and energy are neither influenced during storage
Effectively inhibit harmful microbe growth, provides a kind of more efficient, more good caviar antistaling agent.
Summary of the invention
According to prior art shortcoming, the object of the present invention is to provide a kind of biological crude antistaling agents of sturgeon caviar
GAC8/ β-CD, this antistaling agent is using health, safety, and corrosion-resistanting fresh-keeping effect is excellent, and antibacterial is widely used.
To achieve the above object, technical program of the present invention lies in:
A kind of preparation method of octyl gallate/beta-cyclodextrin supermolecule biology crude antistaling agent, comprising the following steps:
S1. octyl gallate is prepared by the enzymatic method in depth congruent melting solvent；
S2. beta-cyclodextrin is mixed with octyl gallate, using the mixed solution of second alcohol and water as solvent, obtains water
Dissolubility octyl gallate/beta-cyclodextrin super molecule inclusion compound.
Preferably, the biological crude antistaling agent exists in the form of solid powder, GAC8 described in solid and β-
CD molar ratio is 1:(0.5~1.5).
Preferably, in step S2,
In deionized water, β-CD is added, magnetic agitation is to being completely dissolved at room temperature.Then by GAC8 ethanol solution
It is slowly dropped in the β-CD aqueous solution previously prepared, it is lasting to stir.- 4 DEG C of refrigerator 48h are placed, and white form of solid object is precipitated, mistake
Filter.After -20 DEG C of refrigerator cold-storages are stayed overnight, freeze-drying.
Preferably, the stirring condition are as follows: 60 DEG C, 48h.
Preferably, the freeze-drying condition are as follows: -45 DEG C, for 24 hours.
The present invention also provides a kind of using the method for preparing GAC8 by the enzymatic method in depth congruent melting solvent, including with
Lower step:
Acetylcholine is mixed with two hydrogen bond donor urea and glycerol (1:1:1), at 80 DEG C, 2h is stirred, is made transparent
Liquid is depth congruent melting solvent, wherein water content is 10% (w/w) in depth congruent melting solvent.It is sharp in depth congruent melting solvent
Gallicin and the transesterification rear formation gallic acid of octanol (molar ratio 1:6) are catalyzed with lipase (Novo 435,10mg)
Monooctyl ester crude product, recycle chromatographic column be further purified, collect product phase, decompression remove solvent, obtain GAC8 sterling (> 98%,
HPLC)。
The present invention also provides the biological crude antistaling agents that above-mentioned preparation method obtains.
Invention further provides application of the biological crude antistaling agent described in one kind in sturgeon caviar is fresh-keeping.
Wherein, the aqueous solution that the biological crude antistaling agent is formed is sprayed on roe surface when application, is stirred, leaching
Profit, then carries out being packaged to be finished product.
Compared with the existing technology, beneficial effects of the present invention:
GAC8 has extensive fungistatic effect, nontoxic edible, can effectively extend the storage period of product, mention for consumer
For more good product.Octyl gallate is molten using depth congruent melting using pure natural product gallic acid as raw material in the present invention
Enzymatic method preparation in agent, green safe, by-product is few.But GAC8 poor water solubility, it is limited in preservation of fishery
In application.Using the encapsulating effect of β-CD cavity, the water solubility of GAC8 is improved, while also having and increasing the excellent of bacteriostatic activity
Gesture.
Detailed description of the invention
Fig. 1 compares column diagram with the GAC8 yield that control group 1 obtains for case study on implementation 1 of the present invention.
Fig. 2 is the clump count change curve for the sturgeon caviar that the embodiment of the present invention 2~5 and control group 2 obtain.
Fig. 3 is the radar map that 6 sensory evaluation of case study on implementation of the present invention obtains.
Specific embodiment
Below in conjunction with specific embodiment, the present invention will be further described.
Embodiment 1
Described is as follows the step of preparing GAC8 by the enzymatic method in depth congruent melting solvent:
Acetylcholine is mixed with two hydrogen bond donor urea and glycerol (mole 1:1:1), at 80 DEG C, stirs 2h, system
Obtaining thick transparency liquid is that depth is total to solvent.Wherein, water accounts for 10% (w/w) in the ratio of deep congruent melting solvent.It is molten at this
In agent, lipase (Novo 435,10mg) is catalyzed gallicin and octanol (molar ratio 1:1.5) generation transesterification is anti-
It answers, carries out silica gel column chromatography using the mobile phase of petroleum ether and ethyl acetate volume ratio 6:1, the product of preparation is GAC8.It obtains
The esterification yied obtained is shown in Fig. 1.
Reference examples 1
Gallic acid and octanol are made into solvent using methylene chloride (DCM) using traditional direct esterification, at 30 DEG C
Reaction prepares GAC8 for 24 hours.The esterification yied of acquisition is shown in Fig. 1.
Embodiment 2
A kind of biology crude antistaling agent, exists in the form of solid powder, component GAC8 and β-CD molar ratio in powder
For 1:1.5.
The preparation and application of the biology crude antistaling agent the following steps are included:
(1) in deionized water, β-CD is added, magnetic agitation is to being completely dissolved at room temperature.Then by GAC8 dehydrated alcohol
Solution is slowly dropped in the β-CD aqueous solution previously prepared, finally obtains mixture, lasting to stir.- 4 DEG C of refrigerator 48h are put
It sets, white form of solid object is precipitated, filtering.After -20 DEG C of refrigerator cold-storages are stayed overnight, freeze-drying.
(2) a kind of green preservative sprays sturgeon caviar and extends the processing method of its storage period, comprising the following steps:
(3) sorting: female sturgeon of the gonad development in 6~12 ages into the fourth phase is selected to take ovum, female sturgeon as parent population
The ovum diameter of fish is in 2~8mm or more.
(4) ovum, roe separation are taken: the parent population selected being put into temperature to impregnate 30~60min in 5~8 DEG C of ice water；Leaching
Ovary is taken out after bubble, and ovary is squeezed and obtains roe.
(5) it rinses: pouring into appropriate ice water, be gently agitated for roe, rinse repeatedly.
(6) select: drain well manually chooses impurity.
(7) antistaling agent is handled: after the roe weighing handled well, the aqueous solution of 1mg/mL antistaling agent being uniformly sprayed at fish
It on seed surface, stirs evenly, infiltrates 20~25min.
(8) packaging, finished product storage: different grades of roe is sub-packed in the storage tank of disinfection by different weight specification, sealing
Refrigeration, refrigerated storage temperature are -2~2 DEG C.
(9) above method products obtained therefrom storage period reaches for 3~June.
The clump count change curve of obtained product is shown in Fig. 2.
Embodiment 3
A kind of biology crude antistaling agent, exists in the form of solid powder, component GAC8 and β-CD molar ratio in powder
For 1:1.2
The preparation and application of the biology crude antistaling agent the following steps are included:
(1) in deionized water, β-CD is added, magnetic agitation is to being completely dissolved at room temperature.Then by GAC8 dehydrated alcohol
Solution is slowly dropped in the β-CD aqueous solution previously prepared, finally obtains mixture, lasting to stir.- 4 DEG C of refrigerator 48h are put
It sets, white form of solid object is precipitated, filtering.After -20 DEG C of refrigerator cold-storages are stayed overnight, freeze-drying.
(2) a kind of green preservative sprays sturgeon caviar and extends the processing method of its storage period, comprising the following steps:
(3) sorting: female sturgeon of the gonad development in 6~12 ages into the fourth phase is selected to take ovum, female sturgeon as parent population
The ovum diameter of fish is in 2~8mm or more.
(4) ovum, roe separation are taken: the parent population selected being put into temperature to impregnate 30~60min in 5~8 DEG C of ice water；Leaching
Ovary is taken out after bubble, and ovary is squeezed and obtains roe.
(5) it rinses: pouring into appropriate ice water, be gently agitated for roe, rinse repeatedly.
(6) select: drain well manually chooses impurity.
(7) antistaling agent is handled: after the roe weighing handled well, the aqueous solution of 1mg/mL antistaling agent being uniformly sprayed at fish
It on seed surface, stirs evenly, infiltrates 20~25min.
(8) packaging, finished product storage: different grades of roe is sub-packed in the storage tank of disinfection by different weight specification, sealing
Refrigeration, refrigerated storage temperature are -2~2 DEG C.
(9) above method products obtained therefrom storage period reaches 6~August.
The clump count change curve of obtained product is shown in Fig. 2.
Embodiment 4
A kind of biology crude antistaling agent, exists in the form of solid powder, component GAC8 and β-CD molar ratio in powder
For 1:1
The preparation and application of the biology crude antistaling agent the following steps are included:
(1) in deionized water, β-CD is added, magnetic agitation is to being completely dissolved at room temperature.Then by same molar
GAC8 ethanol solution is slowly dropped in the β-CD aqueous solution previously prepared, finally obtains equimolar mixture, persistently stir
It mixes.- 4 DEG C of refrigerator 48h are placed, and white form of solid object is precipitated, filtering.After -20 DEG C of refrigerator cold-storages are stayed overnight, freeze-drying.
(2) a kind of green preservative sprays sturgeon caviar and extends the processing method of its storage period, comprising the following steps:
(3) sorting: female sturgeon of the gonad development in 6~12 ages into the fourth phase is selected to take ovum, female sturgeon as parent population
The ovum diameter of fish is in 2~8mm or more.
(4) ovum, roe separation are taken: the parent population selected being put into temperature to impregnate 30~60min in 5~8 DEG C of ice water；Leaching
Ovary is taken out after bubble, and ovary is squeezed and obtains roe.
(5) it rinses: pouring into appropriate ice water, be gently agitated for roe, rinse repeatedly.
(6) select: drain well manually chooses impurity.
(7) antistaling agent is handled: after the roe weighing handled well, the aqueous solution of 1mg/mL antistaling agent being uniformly sprayed at fish
It on seed surface, stirs evenly, infiltrates 20~25min.
(8) packaging, finished product storage: different grades of roe is sub-packed in the storage tank of disinfection by different weight specification, sealing
Refrigeration, refrigerated storage temperature are -2~2 DEG C.
(9) above method products obtained therefrom storage period reaches June to September.
The clump count change curve of obtained product is shown in Fig. 2.
Embodiment 5
A kind of biology crude antistaling agent, exists in the form of solid powder, component GAC8 and β-CD molar ratio in powder
For 1:0.5
The preparation and application of the biology crude antistaling agent the following steps are included:
(1) in deionized water, β-CD is added, magnetic agitation is to being completely dissolved at room temperature.Then by GAC8 dehydrated alcohol
Solution is slowly dropped in the β-CD aqueous solution previously prepared, finally obtains mixture, lasting to stir.- 4 DEG C of refrigerator 48h are put
It sets, white form of solid object is precipitated, filtering.After -20 DEG C of refrigerator cold-storages are stayed overnight, freeze-drying.
(2) a kind of green preservative sprays sturgeon caviar and extends the processing method of its storage period, comprising the following steps:
(3) sorting: female sturgeon of the gonad development in 6~12 ages into the fourth phase is selected to take ovum, female sturgeon as parent population
The ovum diameter of fish is in 2~8mm or more.
(4) ovum, roe separation are taken: the parent population selected being put into temperature to impregnate 30~60min in 5~8 DEG C of ice water；Leaching
Ovary is taken out after bubble, and ovary is squeezed and obtains roe.
(5) it rinses: pouring into appropriate ice water, be gently agitated for roe, rinse repeatedly.
(6) select: drain well manually chooses impurity.
(7) antistaling agent is handled: after the roe weighing handled well, the aqueous solution of 1mg/mL antistaling agent being uniformly sprayed at fish
It on seed surface, stirs evenly, infiltrates 20~25min.
(8) packaging, finished product storage: different grades of roe is sub-packed in the storage tank of disinfection by different weight specification, sealing
Refrigeration, refrigerated storage temperature are -2~2 DEG C.
(9) above method products obtained therefrom storage period reaches 6~August.
The clump count change curve of obtained product is shown in Fig. 2.
Reference examples 2
The preparation method of reference embodiment 2, but the processing step without antistaling agent in step (7), are directly wrapped
Dress and storage.The clump count change curve of obtained product is shown in Fig. 2.
Embodiment 6
Sensory evaluation group is formed by 6 trained valuation officers, according to the standards of grading of design, is given a mark using scene
Principle, the smell evaporated with caviar, the taste tasted and the color observed, full grains degree and use spoon
Squeezing ovum grain and judging its elasticity is evaluation index, and indices full marks are 5 points, totally five samples, wherein antistaling agent is not added
Caviar is as a control group.Sensory evaluation total score is calculated by weighted statistical, and each index weights are 0.2.Evaluate environment temperature
Degree is 25 DEG C, everyone tastes twice for every portion of caviar, is individually carried out, is not exchanged mutually, and each sample by each valuation officer
It is all gargled with clear water before evaluation to exclude the influence of upper a sample.Obtained Analyses Methods for Sensory Evaluation Results is shown in Fig. 3.
Claims (9)
1. a kind of octyl gallate/beta-cyclodextrin supermolecule biology crude antistaling agent preparation method, which is characterized in that including
Following steps:
S1. octyl gallate is prepared by the enzymatic method in depth congruent melting solvent；
S2. beta-cyclodextrin is mixed with octyl gallate, using the mixed solution of second alcohol and water as solvent, obtains water solubility
Octyl gallate/beta-cyclodextrin super molecule inclusion compound.
2. the preparation method of biology crude antistaling agent according to claim 1, which is characterized in that the biology is natural to be protected
Exist in the form of solid powder after fresh dose of freeze-drying.
3. the preparation method of biology crude antistaling agent according to claim 1, which is characterized in that the octyl gallate
With beta-cyclodextrin according to molar ratio 1:(0.5~1.5) encapsulating.
4. according to the preparation method for the biological crude antistaling agent that claim 1 is stated, which is characterized in that the second alcohol and water mixing is molten
In liquid, the volume ratio of water and ethyl alcohol is 2:1.
5. according to the preparation method for the biological crude antistaling agent that claim 1 is stated, which is characterized in that pass through depth congruent melting in step S1
The step of enzymatic method in solvent prepares octyl gallate is as follows:
In depth congruent melting solvent prepared by acetylcholine and two hydrogen bond donor urea and glycerol, do not eaten using lipase-catalyzed
Octyl gallate crude product is formed after sub- acid methyl esters and octanol are transesterification, chromatographic column is recycled to be further purified, collects product
Phase, decompression remove solvent, obtain octyl gallate sterling；
The molar ratio of the gallicin and octanol is 1:6.
6. the preparation method of biology crude antistaling agent according to claim 1, which is characterized in that in step S2, encapsulation object
Preparation step it is as follows:
At room temperature, beta-cyclodextrin is dissolved in deionized water, magnetic agitation is to being completely dissolved；Again by the nothing of octyl gallate
Hydrous ethanol solution is slowly added dropwise into above-mentioned beta-cyclodextrin aqueous solution, after completion of dropwise addition, 60 DEG C, persistently stirs 48h；- 4 DEG C of refrigerators
Place 48h, until white form of solid object is precipitated, filtrate is collected in filtering, -20 DEG C of refrigerator cold-storages overnight after, after freeze-drying it is described
Biological crude antistaling agent；
The temperature of freeze-drying is -45 DEG C, and the time is for 24 hours.
7. a kind of biological crude antistaling agent that preparation method as described in any one of claims 1 to 6 obtains.
8. a kind of application of biological crude antistaling agent as claimed in claim 7 in sturgeon caviar is fresh-keeping.
9. application of the biology crude antistaling agent according to claim 8 in sturgeon caviar is fresh-keeping, which is characterized in that will
The aqueous solution that the biological crude antistaling agent is formed is sprayed on roe surface, is stirred, then infiltration is packaged to be into
Product.
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| CN113396965A (en) * | 2021-06-17 | 2021-09-17 | 浙江工商大学 | Nutritional nano biological composite preservative, preparation method thereof and application of preservative to preservation of Taihu whitebait |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113396964A (en) * | 2021-05-27 | 2021-09-17 | 浙江工商大学 | Efficient fresh-keeping nano spinning film mediated by octyl gallate and endogenous NO type cyclodextrin, and preparation method and application thereof |
| CN113396965A (en) * | 2021-06-17 | 2021-09-17 | 浙江工商大学 | Nutritional nano biological composite preservative, preparation method thereof and application of preservative to preservation of Taihu whitebait |
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