CN105061610A - Carboxymethylated acanthopanax brachypus polysaccharide, synthesis and purification method and application of carboxymethylated acanthopanax brachypus polysaccharide serving as tobacco humectant - Google Patents
Carboxymethylated acanthopanax brachypus polysaccharide, synthesis and purification method and application of carboxymethylated acanthopanax brachypus polysaccharide serving as tobacco humectant Download PDFInfo
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- CN105061610A CN105061610A CN201510415590.9A CN201510415590A CN105061610A CN 105061610 A CN105061610 A CN 105061610A CN 201510415590 A CN201510415590 A CN 201510415590A CN 105061610 A CN105061610 A CN 105061610A
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- polysaccharide
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- eleutherococcus brachypus
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention relates to a synthesis and purification method of carboxymethylated acanthopanax brachypus polysaccharide. The method comprises steps as follows: acanthopanax brachypus polysaccharide and sodium hydroxide are added to a solvent and stirred to be dissolved, chloroacetic acid is added, the mixture is stirred at the temperature ranging from 60 DEG C to 80 DEG C and has a reaction for 3-5 h, a product is cooled, the pH (potential of hydrogen) value is adjusted to be neutral, ethanol precipitation and filtration are performed, precipitates are collected, the precipitates are dissolved with water and subjected to ethanol precipitation, dialysis and freeze drying, and carboxymethylated acanthopanax brachypus polysaccharide is obtained. A test proves that carboxymethylated acanthopanax brachypus polysaccharide has good physical and sensual moisture retention functions on cigarettes, irritation and offensive odor of the cigarettes can be reduced, mellowness and comfort of smoke of the cigarettes are improved, and carboxymethylated acanthopanax brachypus polysaccharide can serve as the high-performance tobacco humectant to be applied to the cigarettes.
Description
Technical field
The invention belongs to humectant technical field, be specifically related to a kind of carboxymethylation Eleutherococcus Brachypus polysaccharide, method for synthesizing and purifying and the application as tobacco humectant thereof.
Background technology
Current, mainly adopt the polyhydroxy substance such as propylene glycol, sorbyl alcohol as humectant in China's cigarette industry, the main purpose of this type of humectant is used to be to maintain the water ratio of pipe tobacco in the course of processing, improve the resist processing of pipe tobacco, but above-mentioned humectant is to the maintenance of finished cigarettes water ratio with to suck the improvement effect of comfort level unsatisfactory.
Polysaccharide is polymerized by a large amount of monose, and its a large amount of hydroxyl and water molecules form hydrogen bond, and itself just has stronger water-holding power, and polysaccharide is carried out carboxymethylation modification, not only can improve its solvability, and can improve its water-holding power further.At present, at home and abroad there is no the relevant report applied in cigarette as tobacco humectant by carboxymethylation Eleutherococcus Brachypus polysaccharide.
Summary of the invention
The object of the invention is to provide a kind of carboxymethylation Eleutherococcus Brachypus polysaccharide, method for synthesizing and purifying and the application as tobacco humectant thereof.
For achieving the above object, the present invention adopts following technical scheme:
A method for synthesizing and purifying for carboxymethylation Eleutherococcus Brachypus polysaccharide, it comprises the steps: Eleutherococcus Brachypus polysaccharide, sodium hydroxide to join stirring and dissolving in solvent, then adds Mono Chloro Acetic Acid, stirring reaction 3-5h under 60-80 DEG C of condition, cooling, adjust ph is extremely neutral, alcohol precipitation, filter, collecting precipitation, precipitates again through water dissolution, alcohol precipitation, dialysis, namely lyophilize obtains carboxymethylation Eleutherococcus Brachypus Crude polysaccharides.
Concrete, described solvent is that the glyoxaline ion liquid of 1-1.5:1 and water form by mass ratio; The adding proportion of each material is: Eleutherococcus Brachypus polysaccharide: sodium hydroxide: solvent: Mono Chloro Acetic Acid=10g:14-18g:120mL:16-17g.
Further preferably, by carboxymethylation Eleutherococcus Brachypus Crude polysaccharides chromatographic separation purifying twice, obtain refining carboxymethylation Eleutherococcus Brachypus polysaccharide; Twice separation and purification chromatography column used is respectively DEAE-32 cellulose column and SephadexG-200 gel column, and twice separation and purification elutriant used is respectively 0.4mol/LNaCl solution and 0.1mol/LNaCl solution.
Above-mentioned method for synthesizing and purifying is utilized to prepare the carboxymethylation Eleutherococcus Brachypus polysaccharide of gained.
Above-mentioned method for synthesizing and purifying is utilized to prepare the application of carboxymethylation Eleutherococcus Brachypus polysaccharide as tobacco humectant of gained.Preferably, carboxymethylation Eleutherococcus Brachypus polysaccharide adds before baking tabacco scrap, and its broiler diets is the 0.05-1.5 ‰ of pipe tobacco weight.
The present invention obtains carboxymethylation Eleutherococcus Brachypus polysaccharide by synthesis and purifying, and carried out the test of physics humid keeping performance and inherent sensory quality assessment, find that it has good physics and sense organ humectation effect to cigarette, and the pungency of cigarette and assorted gas can be reduced, improve mellow and full sense and the comfortableness of cigarette smoke, can apply in cigarette as a kind of tobacco humectant of excellent property, and determine its Optimum in cigarette.
Compared to the prior art, beneficial effect of the present invention:
1) in the building-up process of carboxymethylation Eleutherococcus Brachypus polysaccharide, solvent (mixed solution of ionic liquid and water 1-1.5:1) is utilized to have good solubility to polysaccharide, effectively improve the concentration of reaction raw materials in unit volume, laying the foundation for improving reaction yield further.
2) adopt Mierocrystalline cellulose and gel chromatography column chromatography for separation purifying twice, obtain highly purified refining carboxymethylation Eleutherococcus Brachypus polysaccharide, whole extraction purification process operation is easy, and raw material and the reagent of use are cheap and easy to get.
3) prove through test: carboxymethylation Eleutherococcus Brachypus polysaccharide of the present invention, to the humectation successful of tobacco product, therefore has significant industrial application value and wide popularizing application prospect.
Embodiment
The present invention is described further by the following examples, but protection scope of the present invention is not limited thereto.
test main agents used and instrument:
Ethanol, sodium hydroxide, acetic acid, phenol, sulfuric acid, sodium-chlor (Guangzhou Chemical Reagent Factory, analytical pure), 1-butyl-3-methylimidazolyl villaumite (Lanzhou chemical physics institute, analytical pure), DEAE-32 cellulose column and SephadexG200 gel (sigma company of the U.S.), experimental water is distilled water.
BS200SWE1 type electronic balance (sensibility reciprocal: 0.0001g, Beijing match Doris balance company limited); R-215 type Rotary Evaporators (BUCHI company of Switzerland); V-700 vacuum pump (BUCHI company of Switzerland); DLSB-20/60 DEG C of subcooling recycle pump (Shanghai Mei Qiang plant and instrument company limited); KDM type regulating temp. electrothermal cover (Shandong Hua Lu electric heating Instrument Ltd.); 85-2 type constant temperature blender with magnetic force (Shanghai Si Le instrument plant), ZK-82B type electric vacunm drying case (Shanghai Shen Guang instrument company limited), CHRIST Freeze Drying Equipment (BUCHI company of Switzerland), TSKGELG2000PW high productivity computing post (Sigma Co., USA), AgilentLC1100 type high performance liquid phase instrument and differential pulse polarograpll instrument (Agilent company of the U.S.).
In the present invention, Eleutherococcus Brachypus polysaccharide can buy common commercially available prod, also can adopt this area ordinary method preparation and obtain.Ionic liquid in embodiment is 1-butyl-3-methylimidazolyl villaumite.
Eleutherococcus Brachypus polysaccharide in following embodiment is adopted and is prepared with the following method and obtain: by the 300g that pulverized dry Eleutherococcus Brachypus 1800ml ether surname extraction 2h in order to except degrease, residue volatilizes.Residue after volatilizing uses 2L boiling water extraction 3 times again, merges the boiling water extraction liquid of 3 gained, and concentrated, centrifugal, get supernatant liquor, the dehydrated alcohol with supernatant liquor 3 times of volumes carries out alcohol precipitation, hold over night (12h), recentrifuge collecting precipitation thing.Throw out dissolves with distilled water with after ethanol, washing with acetone 3 times successively, then the papoid adding weight of precipitate 1 ‰ places 2h in 50 DEG C of water-baths, adopts Sevage method deproteination.Add 8g gac to be placed in 70 DEG C of water-baths and to heat 3h, cross and filter gac, concentrating under reduced pressure, load flowing water in dialysis tubing after naturally cooling and dialyse 48h in order to remove small molecular weight impurity, after dialysis terminates, after again adding dialysis, the dehydrated alcohol of polysaccharide soln volume 3 times amount carries out alcohol precipitation, hold over night (12h), be deposited in 70 DEG C of dry 11.79g Crude polysaccharides, yield is 3.93%.
After getting the dissolving of 2.0g Crude polysaccharides distilled water, by DEAE-Celluose gel chromatography column chromatography for separation (5.0 × 50cm), with 0.5mol/LNaCl solution for moving phase (i.e. elutriant), flow velocity is 2.5ml/min, adopt Phenol-sulphate acid method to develop the color to chromatographic solution, collect main chromatographic peak, freeze-drying.Then by freeze-drying gained solid 0.05mol/LNH
4hCO
3solubilize, by SephadexG200 gel chromatographic columns chromatographic separation (5.0 × 50cm) again, with 0.05mol/LNH
4hCO
3solution is moving phase (i.e. elutriant), and flow velocity is 2.0ml/min, adopts Phenol-sulphate acid method to develop the color to chromatographic solution, collects main chromatographic peak, freeze-drying, obtain 486mg and refine Eleutherococcus Brachypus polysaccharide solid, yield 24.3%, and LT1 sugar content is 95.3% after testing.
embodiment 1
A kind of method for synthesizing and purifying of carboxymethylation Eleutherococcus Brachypus polysaccharide, comprise the steps: in there-necked flask, add 16gNaOH, 120mL solvent (ionic liquid/water=1:1, mass ratio), stirred at ambient temperature is clarified to solution, add 10g and refine Eleutherococcus Brachypus polysaccharide vigorous stirring 20min to fully dissolving, then slowly add 16.2g Mono Chloro Acetic Acid, at 60 DEG C, stirring reaction 3h, is cooled to room temperature, dilute acetic acid adjust ph is 7, alcohol precipitation, filters, collecting precipitation.
Precipitation suitable quantity of water is dissolved, the ethanol alcohol precipitation of 3 times of volumes 95%, the centrifugal 20min of 4000r/m.Collecting precipitation again, and with dialysis tubing, flowing water dialysis is carried out to it.First to dialyse 24h with tap water, then use distill water dialysis 24h, last lyophilize obtains white byssaceous carboxymethylation Eleutherococcus Brachypus Crude polysaccharides.
Be dissolved in distilled water by carboxymethylation Eleutherococcus Brachypus Crude polysaccharides sample, be added in pretreated DEAE-32 Mierocrystalline cellulose chromatography column, with the NaCl solution gradient elution of 0.4mol/L, flow velocity is 0.5mL/min.5mL collected by every test tube, and phend-sulphuric acid detects, and collect each pipe sample containing polysaccharide, dialysis desalting, lyophilize, obtains polysaccharide fraction; With SephadexG-200 gel column, it is further purified, with the NaCl solution wash-out of 0.1mol/L, collects with Fraction Collector equally, each component is collected respectively after detection, namely obtain carboxymethylation Eleutherococcus Brachypus refinishing polyose product through flowing water dialysis, lyophilize, after measured, its substitution value is 0.60.
embodiment 2
A kind of method for synthesizing and purifying of carboxymethylation Eleutherococcus Brachypus polysaccharide, comprise the steps: in there-necked flask, add 16gNaOH, 120mL solvent (ionic liquid/water=1:1, mass ratio), stirred at ambient temperature is clarified to solution, add 10g and refine Eleutherococcus Brachypus polysaccharide vigorous stirring 20min to fully dissolving, then slowly add 17.0g Mono Chloro Acetic Acid, at 70 DEG C, stirring reaction 4h, is cooled to room temperature, dilute acetic acid adjust ph is 7, alcohol precipitation, filters, collecting precipitation.
Precipitation suitable quantity of water is dissolved, the ethanol alcohol precipitation of 3 times of volumes 95%, the centrifugal 20min of 4000r/m.Collecting precipitation again, and with dialysis tubing, flowing water dialysis is carried out to it.First to dialyse 24h with tap water, then use distill water dialysis 24h, last lyophilize obtains white byssaceous carboxymethylation Eleutherococcus Brachypus Crude polysaccharides.
Be dissolved in distilled water by carboxymethylation Eleutherococcus Brachypus Crude polysaccharides sample, be added in pretreated DEAE-32 Mierocrystalline cellulose chromatography column, with the NaCl solution gradient elution of 0.4mol/L, flow velocity is 0.5mL/min.5mL collected by every test tube, and phend-sulphuric acid detects, and collect each pipe sample containing polysaccharide, dialysis desalting, lyophilize, obtains polysaccharide fraction; With SephadexG-200 gel column, it is further purified, with the NaCl solution wash-out of 0.1mol/L, collects with Fraction Collector equally, each component is collected respectively after detection, namely obtain carboxymethylation Eleutherococcus Brachypus refinishing polyose product through flowing water dialysis, lyophilize, after measured, its substitution value is 0.65.
embodiment 3
A kind of method for synthesizing and purifying of carboxymethylation Eleutherococcus Brachypus polysaccharide, comprise the steps: in there-necked flask, add 16gNaOH, 120mL solvent (ionic liquid/water=1:1, mass ratio), stirred at ambient temperature solution is clarified, add 10g and refine Eleutherococcus Brachypus polysaccharide vigorous stirring 20min to fully dissolving, then slowly add 16.6g Mono Chloro Acetic Acid, at 80 DEG C, stirring reaction 5h, is cooled to room temperature, dilute acetic acid adjust ph is 7, alcohol precipitation, filters, collecting precipitation.
Precipitation suitable quantity of water is dissolved, the ethanol alcohol precipitation of 3 times of volumes 95%, the centrifugal 20min of 4000r/m.Collecting precipitation again, and with dialysis tubing, flowing water dialysis is carried out to it.First to dialyse 24h with tap water, then use distill water dialysis 24h, last lyophilize obtains white byssaceous carboxymethylation Eleutherococcus Brachypus Crude polysaccharides.
Be dissolved in distilled water by carboxymethylation Eleutherococcus Brachypus Crude polysaccharides sample, be added in pretreated DEAE-32 Mierocrystalline cellulose chromatography column, with the NaCl solution gradient elution of 0.4mol/L, flow velocity is 0.5mL/min.5mL collected by every test tube, and phend-sulphuric acid detects, and collect each pipe sample containing polysaccharide, dialysis desalting, lyophilize, obtains polysaccharide fraction; With SephadexG-200 gel column, it is further purified, with the NaCl solution wash-out of 0.1mol/L, collects with Fraction Collector equally, each component is collected respectively after detection, namely obtain carboxymethylation Eleutherococcus Brachypus refinishing polyose product through flowing water dialysis, lyophilize, after measured, its substitution value is 0.63.
application test: carboxymethylation Eleutherococcus Brachypus polysaccharide is as the applied research of tobacco humectant
For investigating carboxymethylation Eleutherococcus Brachypus polysaccharide to the physics humid keeping performance of cigarette, with Bright Yellow (Jin Mantang) blank cigarette shreds for carrier, gained carboxymethylation Eleutherococcus Brachypus refinishing polyose product prepared by embodiment 2 and carry out the research of physics humid keeping performance contrast test respectively with Eleutherococcus Brachypus polysaccharide, propylene glycol together with sorbyl alcohol, prepare the above-claimed cpd aqueous solution that massfraction is 5% respectively.First by 1500g mix blank cigarette shreds is placed in temperature 22 ± 1 DEG C, relative humidity 60 ± 2% environment balances 48h.Then equivalent takes five parts of pipe tobaccos, every part of 100g, and evenly apply the 4g above-claimed cpd aqueous solution respectively in pipe tobacco, contrasting blank sample is that pipe tobacco evenly applies 4g water.Then five parts of pipe tobaccos are placed in respectively 22 ± 1 DEG C, investigate it under the environment of relative humidity 40 ± 2% and separate wet process, and the change of instant water ratio is analyzed, investigate its physics humectation effect, the results are shown in Table 1.
Table 1 physics humectation effect comparison table
Test-results shows: the pipe tobacco of interpolation carboxymethylation Eleutherococcus Brachypus polysaccharide, Eleutherococcus Brachypus polysaccharide, propylene glycol and sorbyl alcohol four kinds of compounds is compared with blank pipe tobacco, moisture loss speed is slower, this is that hydrophilic radical hydroxyl contained by polyol can form hydrogen bond with water and be fettered by water, delay scattering and disappearing of moisture, improve the physics humid keeping performance of pipe tobacco; Wherein the physics humid keeping performance of carboxymethylation Eleutherococcus Brachypus polysaccharide is best, is secondly Eleutherococcus Brachypus polysaccharide and propylene glycol, is finally sorbyl alcohol.
2, sense organ humid keeping performance test
Make solvent with 20v% aqueous ethanolic solution, carboxymethylation Eleutherococcus Brachypus refinishing polyose product gained being prepared by embodiment 2 are made into the solution that massfraction is 1%.Get 0.100g, 0.500g, 1.000g, 5.000g, 10.000g, 15.000 and the above-mentioned solution containing carboxymethylation Eleutherococcus Brachypus polysaccharide of 20.000g respectively, then evenly spray is added in seven parts of blank cigarette shreds of not spiced 100g Bright Yellow respectively, roll, respectively pick out 100 same weight cigarette, be placed in temperature 22 DEG C ± 1 DEG C, the climatic chamber of humidity 60% ± 2% balances 48h, smoke panel test.Control sample is the blank cigarette of Bright Yellow, and control sample balances 48h equally under uniform temp, humidity condition.Smoking result is in table 2.
The carboxymethylation Eleutherococcus Brachypus polysaccharide smoking result of table 2 Different adding amount
Smoking result as can be seen from table 2: the Main Function of carboxymethylation Eleutherococcus Brachypus polysaccharide to cigarette shows as and make flue gas obviously become mellow and full, soft, comfortable taste promotes, and assorted gas and pungency reduce.When carboxymethylation Eleutherococcus Brachypus polysaccharide consumption is less, it is not clearly to the effect of cigarette; When its consumption reaches 2.0 ‰, there is the phenomenon of spine sense increase, concentration reduction; When its consumption is 1.0 ‰, sucking quality is best.Therefore, best results when adding 0.1g carboxymethylation Eleutherococcus Brachypus polysaccharide in 100g cigarette, namely optimum consumption is 1 ‰.Therefore, the Optimum of carboxymethylation Eleutherococcus Brachypus polysaccharide is 0.05-1.5 ‰.
Claims (6)
1. a method for synthesizing and purifying for carboxymethylation Eleutherococcus Brachypus polysaccharide, is characterized in that, comprises the steps: Eleutherococcus Brachypus polysaccharide, sodium hydroxide to join stirring and dissolving in solvent, then Mono Chloro Acetic Acid is added, stirring reaction 3-5h under 60-80 DEG C of condition, cooling, adjust ph is to neutral, alcohol precipitation, filters, collecting precipitation, precipitation is again through water dissolution, alcohol precipitation, dialysis, namely lyophilize obtains carboxymethylation Eleutherococcus Brachypus Crude polysaccharides.
2. the method for synthesizing and purifying of carboxymethylation Eleutherococcus Brachypus polysaccharide as claimed in claim 1, is characterized in that, described solvent is that the glyoxaline ion liquid of 1-1.5:1 and water form by mass ratio; The adding proportion of each material is: Eleutherococcus Brachypus polysaccharide: sodium hydroxide: solvent: Mono Chloro Acetic Acid=10g:14-18g:120mL:16-17g.
3. the method for synthesizing and purifying of carboxymethylation Eleutherococcus Brachypus polysaccharide as claimed in claim 1, is characterized in that, by carboxymethylation Eleutherococcus Brachypus Crude polysaccharides chromatographic separation purifying twice, obtains refining carboxymethylation Eleutherococcus Brachypus polysaccharide; Twice separation and purification chromatography column used is respectively DEAE-32 cellulose column and SephadexG-200 gel column, and twice separation and purification elutriant used is respectively 0.4mol/LNaCl solution and 0.1mol/LNaCl solution.
4. utilize the arbitrary described method for synthesizing and purifying of claim 1 to 3 to prepare the carboxymethylation Eleutherococcus Brachypus polysaccharide of gained.
5. carboxymethylation Eleutherococcus Brachypus polysaccharide described in claim 4 is as the application of tobacco humectant.
6. carboxymethylation Eleutherococcus Brachypus polysaccharide, as the application of tobacco humectant, is characterized in that as claimed in claim 5, and carboxymethylation Eleutherococcus Brachypus polysaccharide adds before baking tabacco scrap, and its broiler diets is the 0.05-1.5 ‰ of pipe tobacco weight.
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