CN106279454B - A kind of physical property method of modifying of soluble soybean polysaccharide - Google Patents
A kind of physical property method of modifying of soluble soybean polysaccharide Download PDFInfo
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- CN106279454B CN106279454B CN201510293241.4A CN201510293241A CN106279454B CN 106279454 B CN106279454 B CN 106279454B CN 201510293241 A CN201510293241 A CN 201510293241A CN 106279454 B CN106279454 B CN 106279454B
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Abstract
The invention discloses a kind of soluble soybean polysaccharide physical property method of modifying, belong to agricultural byproducts processing field.Chemical action particularly occurs using octenyl succinic acid anhydride and soybean polyoses and obtains the reaction technology of the novel soybean polysaccharide with hydrophilic-hydrophobic amphipathic characteristic.First with hexametaphosphate as crosslinking agent by soluble soybean polysaccharide cross-linked esterification, then hydrophobic modification reaction is carried out to crosslinking soybean polyoses using octenyl succinic acid anhydride (OSA) under the conditions of pH8.0-8.5, it will obtain octenyl succinic acid anhydride-soybean polyoses ester (OSA-SSPS) crude product to extract by ethyl acetate, and crush and get product after rotary evaporation and freeze-drying or spray drying.Soybean polyoses after appropriate physical property modification have hydrophilic and hydrophobic two kinds of surface naturies simultaneously, are more suitable for playing the stability property of steric hindrance effect.The present invention can further widen its application range, be widely used in food, cosmetics, weaving, papermaking, in pharmaceuticals industry.
Description
Technical field
The invention discloses a kind of soluble soybean polysaccharide physical property method of modifying, particularly to soluble soybean polysaccharide into
Row cross-linked esterification molecular modification, and chemical action occurs using octenyl succinic acid anhydride and soybean polyoses and obtains ocentyl succinic
Acid anhydride-soybean polyoses ester (OSA-SSPS) reaction technology.Belong to agricultural byproducts processing field.
Background technique
Soluble soy protein (Soybean soluble polysaccharides, SSPS) is mentioned from soybean bean dregs
A kind of dietary fiber for the solubility taken out has a variety of application functions, can be used as emulsifier, dispersing agent, stabilizer etc..
In dairy products, it is one that the steric hindrance effect that soluble soybean polysaccharide relies primarily on the formation of polysaccharide side chain, which makes protein stabilization,
The sour milk beverage stabilizer of kind low viscosity.In recent years, soybean polyoses in acidic milk drink using more and more, with dairy products
In it is other commonly improve the stabilizer of stability to increase viscosity and compare, using soluble soybean polysaccharide as the cream of stabilizer
Beverage mouthfeel is salubrious, flavor is natural, viscosity is low.
Acidic dairy prod industry currently on the market has become mature, by years of researches and production practices, in protein
0.4% pectin is added as stabilizer in the acidic dairy prod that content is 1% and has become a kind of usage of trade, because 0.4%
Pectin can stable acidic milk beverage well.But pectin dealing in recent years is well sold and in short supply, supply falls short of demand, price continuous rise,
The profit margin of businessman is also smaller and smaller.The challenge of this industry faces innovation.The commercialization of soluble soybean polysaccharide at present
Product, the ability for stablizing lactoprotein particle in the acidic dairy prod that protein content is 1% are not satisfactory；In addition, in emulsus
In liquid system, the soluble soybean polysaccharide of commercially produced product cannot be formed as stabilizer stablizes O/W emulsion system well.
In terms of soluble soybean polysaccharide modification, there is the research being modified using extruding, extruding, enzyme process etc. to fiber both at home and abroad, change
It has been apt to the functional characteristic of soybean polyoses.
The steric hindrance that soluble soybean polysaccharide relies primarily on tral sugar side chains acts on to realize its functional stabilizer
Use value, but soybean polyoses molecular weight is smaller, and chain length is shorter, and steric hindrance effect is limited, passes through esterification and crosslinking reaction modifying
Soybean polyoses increase its side chain, steric hindrance effect enhancing, to improve its emulsion stability；Ocentyl succinic simultaneously
The existing hydrophobic chain alkyl of acid anhydride (OSA), and have the good hydrophily anhydride group of reactivity.It is double that many scholars are based on it
The property of parent's property is made octenyl succinic starch ester through esterification with cornstarch, tapioca, potato starch etc., makes
Obtaining product has hydrophilic and hydrophobic property, is a kind of peace used by the major country approval of the U.S., Europe and the Asian-Pacific area
The high edible emulsifing thickener of full property, is widely used in the industries such as food, medicine, cosmetics, chemical industry.Therefore, the present invention is logical
It crosses cross-linked esterification reaction and OSA suitably modifies soluble soybean polysaccharide, well solved soluble soybean polysaccharide and be applied to
The problems such as placing the suspended matter, sediment or layering of generation in acidic milk drink for a long time, the soybean polyoses after physical property modification are simultaneously
With hydrophilic and hydrophobic two kinds of surface naturies, it is more suitable for playing the stable essence of steric hindrance effect；By to soybean polyoses point
The modification of sub- side chain reinforces the effect of its steric hindrance, then can be further improved its dispersion stabilization.The technology can be opened up further
Its wide application range, be widely used in food, cosmetics, weaving, papermaking, in pharmaceuticals industry.Cost of material used in the present invention is low
Honest and clean, reagent and method safety, economical, practical, industrialized production is simple and easy to control, and product, which has, preferably stablizes lactoprotein grain
The ability of son.
Summary of the invention
The present invention solves that soluble soybean polysaccharide molecular weight is smaller, and chain length is shorter, and steric hindrance effect is limited, stablizes cream
The problem of albumen particle ability difference, proposes a kind of soluble soybean polysaccharide physical property method of modifying.
Technical solution provided by the invention, a kind of soluble soybean polysaccharide physical property method of modifying: to soluble soybean polysaccharide
Cross-linked esterification molecular modification is carried out, and chemical action occurs using octenyl succinic acid anhydride and soybean polyoses and obtains octenyl succinic
Acid anhydrides-soybean polyoses ester (OSA-SSPS) reaction technology.Specific step is as follows:
(1) cross-linked esterification reacts: soluble soybean polysaccharide is modulated into the solution that concentration is mass fraction 5-10% with water,
The hexametaphosphate for accounting for soybean polyoses quality 5%-10% is added as crosslinking agent, the hydrochloric acid that concentration is 5% mass fraction is added
Solution adjusts pH to 5.0-5.5, stirs 0.5-1h at 20-30 DEG C.
(2) hydrophobic modification reacts: the crosslinking soybean polyoses solution of step (1) being placed in 35-40 DEG C of water-bath, and spiral shell
Rotation stirring under conditions of be added concentration be 5% mass fraction sodium hydroxide solution, make range of the pH 8.0~8.5, then by
Octenyl succinic acid anhydride (OSA) 5-25ml is added dropwise in drop.It is the sodium hydroxide solution of 5% mass fraction with concentration in reaction process
The pH of control reaction system is maintained between 8.0~8.5, reacts 30-60min.It is the hydrochloric acid solution of 5% mass fraction with concentration
The pH for adjusting solution is 5.5-6.5, and rotary evaporation in vacuo concentration obtains octenyl succinic acid anhydride-soybean polyoses ester (OSA-
SSPS) crude product.
(3) ethyl acetate is handled: three times with isometric ethyl acetate extraction, rotary evaporation removes remaining acetic acid second
It crushes and gets product after ester, freeze-drying or spray drying.
Wherein, step (1) the cross-linked esterification reaction condition are as follows: it is quality that soluble soybean polysaccharide, which is modulated into concentration with water,
The solution of number 10% is added and accounts for the hexametaphosphate of soybean polyoses quality 6% as crosslinking agent, adjusting pH to 5.0, at 25 DEG C
Stir 0.5-1h.
Wherein, step (2) the hydrophobic modification reaction condition are as follows: by the crosslinking soybean polyoses solution of step (1) in 35-40
Under the conditions of DEG C, auger is added dropwise octenyl succinic acid anhydride (OSA) 15ml dropwise, reacts 45min, in reaction process, uses concentration
PH for the sodium hydroxide solution control reaction system of 5% mass fraction is maintained between 8.0~8.5.It is with concentration after reaction
The hydrochloric acid solution of 5% mass fraction adjusts pH 6.0, and rotary evaporation in vacuo concentration obtains octenyl succinic acid anhydride-soybean polyoses
Ester (OSA-SSPS) crude product.
Wherein, hexametaphosphate described in step (1) is calgon.
It is 0.0059-0.0206 with OSA-SSPS degree of substitution prepared by the method for the present invention.
Beneficial effects of the present invention: the method for the present invention, which has been put forward for the first time, first carries out cross-linked esterification point to soluble soybean polysaccharide
Son modification further occurs chemical action using octenyl succinic acid anhydride and soybean polyoses and obtains octenyl succinic acid anhydride-greatly
The reaction technology of beans polysaccharide esters (OSA-SSPS), applied in the production of soluble soybean polysaccharide.By cross-linked esterification react with
And OSA suitably modify after soluble soybean polysaccharide, soybean polyoses have hydrophilic and hydrophobic two kinds of surface naturies simultaneously, are more suitable for
Play steric hindrance effect stablizes essence；By the modification to soybean polyoses molecular side chain, the effect of its steric hindrance is strengthened,
It then can be further improved its dispersion stabilization.The technology can further widen its application range, be widely used in food, makeup
Product, weaving, papermaking, in pharmaceuticals industry.Low in raw material price used in the present invention, reagent and method safety, economic, practicability
By force, industrialized production is simple and easy to control, it is easy to accomplish.
Specific embodiment
Embodiment 1
Material:
Soluble soybean polysaccharide (SSPS) derives from Fujian Wei Bo Food Co., Ltd.
Soluble soybean polysaccharide is modulated into the solution that concentration is mass fraction 5% with water, addition accounts for soybean polyoses quality
5% hexametaphosphate adjusts as crosslinking agent and stirs 0.5h at 5.0,25 DEG C of pH value of solution；Crosslinking soybean polyoses solution is put afterwards
It is placed in 35 DEG C of water-baths, range of the pH 8.0~8.5 is adjusted under conditions of auger, octenyl amber is then added dropwise dropwise
Amber acid anhydrides (OSA) 5ml, in being dripped in 30min, in reaction process between maintenance system pH 8.0~8.5.It uses after the reaction was completed
Adjustment system pH is 5.5 immediately, and rotary evaporation in vacuo concentration obtains octenyl succinic acid anhydride-soybean polyoses ester (OSA-SSPS)
Crude product.Three times with isometric ethyl acetate extraction, rotary evaporation removes remaining ethyl acetate, crushes after freeze-drying to obtain the final product
Finished product.After measured, degree of substitution 0.0059.
Embodiment 2
Soluble soybean polysaccharide is modulated into the solution that concentration is mass fraction 10% with water, addition accounts for soybean polyoses quality
8% hexametaphosphate adjusts as crosslinking agent and stirs 1h at 5.2,20 DEG C of pH value of solution；Crosslinking soybean polyoses solution is placed afterwards
PH is adjusted in 40 DEG C of water-baths, under conditions of auger in 8.0~8.5 range, and octenyl succinic is then added dropwise dropwise
Acid anhydrides (OSA) 25ml, in being dripped in 60min, in reaction process between maintenance system pH 8.0~8.5.It uses after the reaction was completed
Adjustment system pH is 6.0 immediately, and rotary evaporation in vacuo concentration obtains octenyl succinic acid anhydride-soybean polyoses ester (OSA-SSPS)
Crude product.Three times with isometric ethyl acetate extraction, rotary evaporation removes remaining ethyl acetate, crushes after spray drying to obtain the final product
Finished product.After measured, degree of substitution 0.0206.
Embodiment 3
Soluble soybean polysaccharide is modulated into the solution that concentration is mass fraction 8% with water, addition accounts for soybean polyoses quality
6% hexametaphosphate adjusts as crosslinking agent and stirs 45min at 5.5,30 DEG C of pH value of solution；It will be crosslinked soybean polyoses solution afterwards
It is placed in 37 DEG C of water-baths, pH is adjusted under conditions of auger in 8.0~8.5 range, octenyl is then added dropwise dropwise
Succinic anhydride (OSA) 15ml, in being dripped in 45min, in reaction process between maintenance system pH 8.0~8.5.Reaction is completed
It is afterwards 6.5 with adjustment system pH immediately, rotary evaporation in vacuo concentration obtains octenyl succinic acid anhydride-soybean polyoses ester (OSA-
SSPS) crude product.Three times with isometric ethyl acetate extraction, rotary evaporation removes remaining ethyl acetate, powder after freeze-drying
It is broken to get product.After measured, degree of substitution 0.0083.
Embodiment 4
Soluble soybean polysaccharide is modulated into the solution that concentration is mass fraction 6% with water, addition accounts for soybean polyoses quality
10% hexametaphosphate adjusts as crosslinking agent and stirs 0.5h at 5.0,30 DEG C of pH value of solution；It will be crosslinked soybean polyoses solution afterwards
It is placed in 40 DEG C of water-baths, pH is adjusted under conditions of auger in 8.0~8.5 range, octenyl is then added dropwise dropwise
Succinic anhydride (OSA) 20ml, in being dripped in 45min, in reaction process between maintenance system pH 8.0~8.5.Reaction is completed
It is afterwards 6.0 with adjustment system pH immediately, rotary evaporation in vacuo concentration obtains octenyl succinic acid anhydride-soybean polyoses ester (OSA-
SSPS) crude product.Three times with isometric ethyl acetate extraction, rotary evaporation removes remaining ethyl acetate, powder after spray drying
It is broken to get product.After measured, degree of substitution 0.0125.
Claims (4)
1. a kind of physical property method of modifying of soluble soybean polysaccharide, it is characterised in that: carry out cross-linked ester to soluble soybean polysaccharide
Chemoattractant molecule modification, and chemical action occurs using octenyl succinic acid anhydride and soybean polyoses and obtains octenyl succinic acid anhydride-soybean
The reaction technology of polysaccharide esters (OSA-SSPS), the specific steps are as follows:
(1) cross-linked esterification reacts: soluble soybean polysaccharide being modulated into the solution that concentration is mass fraction 5-10% with water, is added
The hexametaphosphate of soybean polyoses quality 5%-10% is accounted for as crosslinking agent, the hydrochloric acid solution that concentration is 5% mass fraction is added
PH to 5.0-5.5 is adjusted, stirs 0.5-1h at 20-30 DEG C；
(2) hydrophobic modification reacts: the crosslinking soybean polyoses solution of step (1) being placed in 35-40 DEG C of water-bath, and spiral is stirred
The sodium hydroxide solution that concentration is 5% mass fraction is added under conditions of mixing, makes pH in 8.0~8.5 range, then drips dropwise
Add octenyl succinic acid anhydride (OSA) 5-25ml；In reaction process, controlled with the sodium hydroxide solution that concentration is 5% mass fraction
The pH of reaction system is maintained between 8.0~8.5, reacts 30-60min；It is adjusted with the hydrochloric acid solution that concentration is 5% mass fraction
The pH of solution is 5.5-6.5, and it is thick to obtain octenyl succinic acid anhydride-soybean polyoses ester (OSA-SSPS) for rotary evaporation in vacuo concentration
Product；
(3) ethyl acetate is handled: three times with isometric ethyl acetate extraction, rotary evaporation removes remaining ethyl acetate, cold
It crushes and gets product after dry or spray drying is lyophilized.
2. the physical property method of modifying of a kind of soluble soybean polysaccharide according to claim 1, it is characterised in that: step (1) institute
State cross-linked esterification reaction condition are as follows: soluble soybean polysaccharide is modulated into the solution that concentration is mass fraction 10% with water, and addition accounts for
The hexametaphosphate of soybean polyoses quality 6% adjusts pH to 5.0, stirs 0.5-1h at 25 DEG C as crosslinking agent.
3. the physical property method of modifying of a kind of soluble soybean polysaccharide according to claim 1, it is characterised in that: step (2) institute
State hydrophobic modification reaction condition are as follows: by the crosslinking soybean polyoses solution of step (1) under the conditions of 35-40 DEG C, auger is dropwise
Octenyl succinic acid anhydride (OSA) 15ml is added dropwise, reacts 45min, is the hydroxide of 5% mass fraction with concentration in reaction process
The pH of sodium solution control reaction system is maintained between 8.0~8.5；It is the hydrochloric acid solution of 5% mass fraction that concentration is used after reaction
PH 6.0 is adjusted, rotary evaporation in vacuo concentration obtains octenyl succinic acid anhydride-soybean polyoses ester (OSA-SSPS) crude product.
4. the physical property method of modifying of a kind of soluble soybean polysaccharide according to claim 1, it is characterised in that: step (1) institute
The hexametaphosphate stated is calgon.
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| CN107296125A (en) * | 2017-05-31 | 2017-10-27 | 北京佑众全椒制药有限公司 | It is a kind of to reduce the preparation method of blood fat chrysanthemum beverage |
| CN107232353A (en) * | 2017-05-31 | 2017-10-10 | 北京佑众全椒制药有限公司 | A kind of preparation method of clearing heat and detoxicating chrysanthemum beverage |
| CN107535621B (en) * | 2017-07-19 | 2020-09-22 | 华南理工大学 | Soluble soybean polysaccharide-based orange oil powder and preparation method thereof |
| CN108477304A (en) * | 2018-03-13 | 2018-09-04 | 重庆拜月食品科技有限公司 | Liquid milk stabilizer and its application in liquid milk pasteurize |
| CN108323569A (en) * | 2018-03-13 | 2018-07-27 | 重庆拜月食品科技有限公司 | Pasteurize goat milk and its manufacture craft |
| CN109354699A (en) * | 2018-08-01 | 2019-02-19 | 华南理工大学 | A kind of emulsion oil-in-water and preparation method thereof based on esterification soybean polyoses |
| CN111303308A (en) * | 2019-12-16 | 2020-06-19 | 福建省泉州市味博食品有限公司 | Production process of soluble soybean polysaccharide for rice and flour products |
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| CN103626888A (en) * | 2013-12-10 | 2014-03-12 | 苏州大学 | Glucomannan succinate preparation method |
| CN104395347A (en) * | 2012-06-21 | 2015-03-04 | 不二制油株式会社 | Polysaccharide succinic acid derivative ester of leguminous seed and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104395347A (en) * | 2012-06-21 | 2015-03-04 | 不二制油株式会社 | Polysaccharide succinic acid derivative ester of leguminous seed and preparation method thereof |
| CN103626888A (en) * | 2013-12-10 | 2014-03-12 | 苏州大学 | Glucomannan succinate preparation method |
Non-Patent Citations (1)
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