CN102627701A - Preparation method of galloyl konjac glucomannan - Google Patents
Preparation method of galloyl konjac glucomannan Download PDFInfo
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- CN102627701A CN102627701A CN201210104196XA CN201210104196A CN102627701A CN 102627701 A CN102627701 A CN 102627701A CN 201210104196X A CN201210104196X A CN 201210104196XA CN 201210104196 A CN201210104196 A CN 201210104196A CN 102627701 A CN102627701 A CN 102627701A
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Abstract
The invention relates to a preparation method of galloyl konjac glucomannan. The preparation method comprises the following steps of: preparing triacetyl gallic acid; preparing triacetyl galloyl acryl chloride; preparing triacetyl galloyl konjac glucomannan; preparing the galloyl konjac glucomannan; and the like. According to the preparation method, the gallic acid is utilized to modify konjac glucomannan through esterification; and both the viscosity and the stability of hydrosol of the konjac glucomannan are obviously improved. The preparation method has the advantages of simplicity and convenience in process operation, high production efficiency, low equipment requirement and the like; the total yield can reach over 60 percent; large-scale production can be realized; and the preparation method has high economic and social value and broad application prospect.
Description
[technical field]
The invention belongs to chemical technology field.More specifically, the present invention relates to a kind of preparation method of Nutgalls acyl konjak glucomannan.
[background technology]
Konjak glucomannan (KGM) is a kind of vegetable polysaccharides, has good thickening property and unique gelling, at aspects such as food, chemical industry, weaving, medicine important purposes is arranged, but the poor stability of the KGM water-sol has limited it and used widely.
Gallic acid (3,4, the 5-trihydroxybenzoic acid) is the ubiquitous a kind of polyphenols of nature, can with hydroxyl generation esterification, generate gallate ester, have the radical of removing, anti-oxidant, effect such as suppress that plurality of enzymes is lived.Gallate ester can be applicable to inhibitor, biofuel and some the material antioxidative stabilizer and the inhibitor of grease or oil base food, aspects such as antitumor and cardiovascular medicament; Can also be grafted in the high molecular polymer, preparation has high performance material.
At present, also there is not the relevant report that konjak glucomannan is carried out modification with gallic acid.The inventor has accomplished the present invention through research.
[summary of the invention]
The preparation method who the purpose of this invention is to provide a kind of Nutgalls acyl konjak glucomannan.
The present invention realizes through following technical proposals.
The present invention relates to a kind of preparation method of Nutgalls acyl konjak glucomannan.
Nutgalls acyl konjak glucomannan preparation feedback process is following:
Each step of this preparation process will be described below:
(A) preparation triacetyl gallic acid, the compound 1 in the Nutgalls acyl konjak glucomannan preparation feedback.
Gallic acid, diacetyl oxide and anhydrous pyridine react 10～15h according to mol ratio 1: 2～6: 2～6 under the condition of 22～28 ℃ of temperature; Dilute with zero(ppm) water then; Then add concentrated hydrochloric acid and its solution is adjusted to pH 0.8～12 o'clock generates a kind of deposition, through filter separate after, the throw out that obtains is used cold water washing; Dry again to constant weight, obtain the triacetyl gallic acid of white powder like this.
Preferred gallic acid, diacetyl oxide and anhydrous pyridine react 11～13h according to mol ratio 1: 3～5: 3～5 under the condition of 24～26 ℃ of temperature.
In its reaction process, need to use the normally used whisking appliance of people slowly to stir, its stirring velocity is 20～40 commentaries on classics/min normally.
After reaction finished, its reaction soln need use the zero(ppm) water of 4～6 times of reaction soln volumes to dilute.Preferably, after dilution, add concentrated hydrochloric acid its solution is adjusted to pH 1.0.
With deposition occurring behind the concentrated hydrochloric acid adjusting pH, suction filtration obtains solids and uses the small amount of cold water washing, and its solids is dried to constant weight under the condition of 55～65 ℃ of temperature, gets the white powder product.Product carried out performance liquid chromatography (HPLC) analyze with hydrogen nuclear magnetic resonance (
1H-NMR) spectrum analysis (Fig. 1 and Fig. 2).
The efficient liquid phase chromatographic analysis condition
(B) preparation triacetyl Nutgalls acyl chlorides, the compound 2 in the Nutgalls acyl konjak glucomannan preparation feedback
The triacetyl gallic acid and the sulfur oxychloride of step (A) preparation react 2～6h according to mol ratio 1: 1～5 under the condition of 70～90 ℃ of temperature.Preferably, triacetyl gallic acid and sulfur oxychloride react 3～5h according to mol ratio 1: 2～4 under the condition of 75～85 ℃ of temperature.
Then, this reactant carries out underpressure distillation and removes remaining sulfur oxychloride, and the solid abrasive powdered that obtains is followed vacuum-drying 10～15h, obtains the product of white powder.
Preferably after the reaction of triacetyl gallic acid and sulfur oxychloride finished, this reactant carried out underpressure distillation under 50～70 ℃ condition, the pressed powder vacuum-drying 12～14h that obtains.The sample determination fusing point is 103～105 ℃ (literature value is 106～107 ℃), and the white powder product that shows gained is a triacetyl Nutgalls acyl chlorides.
In the present invention, employed vacuum distillation equipment and vacuum dryer all are product solds in the market, the vacuum distillation equipment sold of the inferior flourish company in Shanghai for example, the vacuum dryer that river in Zhejiang Province, Shanghai power company sells.
(C) preparation triacetyl Nutgalls acyl konjak glucomannan, the compound 3 in the Nutgalls acyl konjak glucomannan preparation feedback.
Konjak glucomannan (KGM) with the anhydrous pyridine solvent-swollen after; Be added in the triacetyl Nutgalls acyl chlorides that step (B) obtains; The mass ratio 1: 1～4 of konjak glucomannan and triacetyl Nutgalls acyl chlorides reacts 1.2～1.8h under the condition of 45～55 ℃ of temperature.Preferred triacetyl Nutgalls acyl chlorides and konjak glucomannan react 1.4～1.6h under the condition of 48～52 ℃ of its mass ratio 1: 2～3 and temperature.Then whole reaction system is cooled to room temperature, with the absolute ethyl alcohol dilution, the throw out that obtains is used absolute ethanol washing after separating, then be dried to constant weight, obtains triacetyl Nutgalls acyl konjak glucomannan again.
Preferably in the absolute ethyl alcohol dilution, need constantly stir, on reactor wall, not have dirt settling.The throw out that obtains is with absolute ethanol washing 2～4 times, drain many powdery products, then under the condition of 55～65 ℃ of temperature, dry to constant weight.The product that obtains is carried out IR spectroscopy, also measured the ir spectra (Fig. 3) of konjak glucomannan simultaneously.The IR spectroscopy condition is that sample and KBr are ground evenly back pressed disc method according to 1: 100 ratio, and scanning times is 32 times, and sweep limit is 4000～400cm
-1
The infrared spectrogram of konjak glucomannan is seen Fig. 3, and the infrared spectrogram of triacetyl Nutgalls acyl konjak glucomannan is seen Fig. 4.Infrared spectrogram through analysis 3 and Fig. 4 can be known, compare with the konjak glucomannan infrared spectrum, the infrared spectrogram of triacetyl Nutgalls acyl konjak glucomannan 1750,1160,1180cm
-1The place absorbs obviously, explains to have C=O and C-O key, and at 3600～3100cm
-1The place; The infrared spectrogram of triacetyl Nutgalls acyl konjak glucomannan is compared with the konjak glucomannan that does not carry out esterification; The peak type narrows down and absorption intensity diminishes; Explain that alcoholic extract hydroxyl group significantly reduces, esterification has taken place in the alcoholic extract hydroxyl group of triacetyl Nutgalls acyl chlorides and konjak glucomannan, has formed triacetyl Nutgalls acyl konjak glucomannan.Analytical results shows that described light brown powder shape product is a triacetyl Nutgalls acyl konjak glucomannan.
(D) preparation Nutgalls acyl konjak glucomannan, the compound 4 in the Nutgalls acyl konjak glucomannan preparation feedback.
According in mL saturated acetic acid sodium ethanol solution with in the ratio 20～60mL/g of g triacetyl Nutgalls acyl konjak glucomannan; Preferably; According in mL saturated acetic acid sodium ethanol solution be 30～50mL/g in the ratio of g triacetyl Nutgalls acyl konjak glucomannan; The triacetyl Nutgalls acyl konjak glucomannan of step (C) preparation is dissolved in the saturated acetic acid sodium ethanol solution, at room temperature stirs 0.8～1.2h, after separation and drying, obtain a kind of product.Carry out under the condition that preferred drying temperature is 55～65 ℃.
The product that then obtains has carried out IR spectroscopy (Fig. 5), and its IR spectroscopy condition such as foregoing condition are identical.Infrared spectrogram through analysis 5 can know that described product is a Nutgalls acyl konjak glucomannan.
To measure the water-sol viscosity and the stability of konjak glucomannan and Nutgalls acyl konjak glucomannan below.
Viscosity measurement: take by weighing konjak glucomannan (Nutgalls acyl konjak glucomannan) 1.5g and add boiling water 100mL, be stirred to thickness, place 24h, carry out viscosimetric analysis with NDJ-1 type viscometer.
The viscosimetric analysis result: konjak glucomannan viscosity is 0.3 * 10
-3Pas, Nutgalls acyl konjak glucomannan viscosity is 0.9 * 10
-3Pas.
4stability determination: (1%, w/v) lucifuge is placed under room temperature, observes the time that flocks occurs with the water-sol of sample.
Stability is measured the result: konjak glucomannan is 3 days, and Nutgalls acyl konjak glucomannan is 5 days.
The result knows by said determination, uses gallic acid through esterification konjak glucomannan to be carried out modification, all improves significantly for the water-sol viscosity and the stability of konjak glucomannan.Therefore, at food, chemical industry is weaved to it, and the application in the technical fields such as medicine has its important effect.
The present invention utilizes gallic acid to make the konjak glucomannan modification through esterification, all improves significantly for the water-sol viscosity and the stability of konjak glucomannan.The present invention has that technological operation is easy, and production efficiency is higher, and is low for equipment requirements, and total recovery can reach more than 60%.Can large-scale production, better economic social value and application prospects are arranged.
[description of drawings]
Fig. 1: triacetyl gallic acid (compound 1) HPLC analyzes collection of illustrative plates;
Fig. 2: triacetyl gallic acid (compound 1) hydrogen spectrum analysis collection of illustrative plates: 1HNMR (DMSO-d6) δ 2.29 (s, 6H), 2.32 (s, 3H), 7.74 (s, 2H), 13.39 (S, 1H);
Fig. 3: the infrared spectrogram of konjak glucomannan;
Fig. 4: triacetyl Nutgalls acyl konjak glucomannan infrared spectrum;
Fig. 5: Nutgalls acyl konjak glucomannan infrared spectrum.
[embodiment]
Can understand the present invention better through following embodiment.
Embodiment 1: preparation Nutgalls acyl konjak glucomannan
Implementation step is following:
(A) preparation triacetyl gallic acid
With gallic acid (30g, 0.177mol), acetic anhydride (67mL, 0.708mol), anhydrous pyridine (57mL; 0.708mol) add at 1: 4: 4 in the 1000mL round-bottomed flask (ice bath) with mol ratio, under the condition of 25 ℃ of temperature, slowly stir 12h, add 620mL water then; The i.e. water of 5 times of reaction volumes dilution then adds concentrated hydrochloric acid the pH value of its solution is adjusted to 1, after this occurs precipitating; Suction filtration, the solid that obtains is used the small amount of cold water washing, under the condition of 55～65 ℃ of temperature, dries to constant weight; Obtain 46.46g white powder solid, the method that adopts this specification sheets to describe identifies that its white powder solid is the triacetyl gallic acid.According to raw material consumption and its productive rate of product amount calculating is 87%, and measuring its fusing point according to conventional fusing point test method is 172～173 ℃.
(B) preparation triacetyl Nutgalls acyl chlorides
The triacetyl gallic acid 30g (0.10mol) of step (A) preparation is added in the round-bottomed flask (250mL) with sulfur oxychloride 21.96mL (0.30mol) (its mol ratio 1: 3); Stirring reaction 4h under the condition of 80 ℃ of temperature; Pressure reducing and steaming sulfur oxychloride under the condition of 60 ℃ of temperature then, the solid vacuum-drying 12h that obtains obtains 30.604g white powder solid; The method that adopts this specification sheets to describe identifies that its white powder solid is a triacetyl Nutgalls acyl chlorides.Raw material consumption and product amount according to this step are calculated, and its productive rate is 96%, and measuring its fusing point according to conventional fusing point test method is 103～105 ℃.
(C) preparation triacetyl Nutgalls acyl konjak glucomannan
In round-bottomed flask; Add 10g konjak glucomannan (KGM); Under the condition of 50 ℃ of temperature, add the 40mL anhydrous pyridine and carry out swelling 0.5h; In the presence of the anhydrous pyridine solvent, in 0.5h, divide 4 batches then and add the triacetyl Nutgalls acyl chlorides that 20g obtains in step (B), the mass ratio of its konjak glucomannan and triacetyl Nutgalls acyl chlorides is 1: 2, under this temperature, reacts 1.5h.Reaction is cooled to room temperature with whole reaction system after finishing.Add the dilution of 300mL absolute ethyl alcohol again, ceaselessly stir simultaneously, on reactor wall, do not have dirt settling, suction filtration.The throw out that obtains with 50mL absolute ethanol washing three times, is drained powdered after separating.Filter cake placed under 60 ℃ of the temperature be dried to constant weight, obtain the 24.6g product, the method that adopts this specification sheets to describe identifies that this product is a triacetyl Nutgalls acyl konjak glucomannan.Raw material consumption and product amount according to this step are calculated, and its productive rate is 82%.
(D) preparation Nutgalls acyl konjak glucomannan
The triacetyl Nutgalls acyl konjak glucomannan (10g) of step (C) the preparation ratio according to 40mL/g is dissolved in the ethanol solution of saturated acetic acid sodium; At room temperature stir 1h; Suction filtration is dry; Obtain the 9.2g product, the method that adopts this specification sheets to describe identifies that this product is a Nutgalls acyl konjak glucomannan.Raw material consumption and product amount according to this step are calculated, and its productive rate is 92%.
Calculate according to the raw material consumption of this embodiment use and the amount of product Nutgalls acyl konjak glucomannan, its total recovery is 63%.The method that adopts this specification sheets to describe has been measured the water-sol viscosity and the stability of the Nutgalls acyl konjak glucomannan of present embodiment preparation, and its result is respectively 0.9 * 10
-3Pas and 5 days.
Embodiment 2: preparation Nutgalls acyl konjak glucomannan
This embodiment is according to carrying out with embodiment 1 identical mode, just in step (A), the mol ratio of gallic acid, acetic anhydride and anhydrous pyridine is adjusted into 1: 2: 6; Step B) the triacetyl gallic acid for preparing and the mol ratio of sulfur oxychloride 1: 2; In step (C), the mass ratio of its konjak glucomannan and triacetyl Nutgalls acyl chlorides is 1: 4; In step (D), the triacetyl Nutgalls acyl konjak glucomannan of step (C) preparation is dissolved in the ethanol solution of saturated acetic acid sodium according to the ratio of 25mL/g.
Calculate according to the raw material consumption of this embodiment use and the amount of product Nutgalls acyl konjak glucomannan, its total recovery is 56%.The method that adopts this specification sheets to describe has been measured the water-sol viscosity and the stability of the Nutgalls acyl konjak glucomannan of present embodiment preparation, and its result is respectively 1.0 * 10
-3Pas and 5 days.
Embodiment 3: preparation Nutgalls acyl konjak glucomannan
This embodiment is according to carrying out with embodiment 1 identical mode, just in step (A), the mol ratio of gallic acid, acetic anhydride and anhydrous pyridine is adjusted into 1: 6: 2; The triacetyl gallic acid of step (B) preparation and the mol ratio of sulfur oxychloride 1: 5; In step (C), the mass ratio of its konjak glucomannan and triacetyl Nutgalls acyl chlorides is 1: 2; In step (D), the triacetyl Nutgalls acyl konjak glucomannan of step (C) preparation is dissolved in the ethanol solution of saturated acetic acid sodium according to the ratio of 60mL/g.
Calculate according to the raw material consumption of this embodiment use and the amount of product Nutgalls acyl konjak glucomannan, its total recovery is 62%.The method that adopts this specification sheets to describe has been measured the water-sol viscosity and the stability of the Nutgalls acyl konjak glucomannan of present embodiment preparation, and its result is respectively 0.7 * 10
-3Pas and 5 days.
Embodiment 4: preparation Nutgalls acyl konjak glucomannan
This embodiment is according to carrying out with embodiment 1 identical mode, just in step (A), the mol ratio of gallic acid, acetic anhydride and anhydrous pyridine is adjusted into 1: 3: 5; The triacetyl gallic acid of step (B) preparation and the mol ratio of sulfur oxychloride 1: 4; In step (C), the mass ratio of its konjak glucomannan and triacetyl Nutgalls acyl chlorides is 1: 3; In step (D), the triacetyl Nutgalls acyl konjak glucomannan of step (C) preparation is dissolved in the ethanol solution of saturated acetic acid sodium according to the ratio of 50mL/g.
Calculate according to the raw material consumption of this embodiment use and the amount of product Nutgalls acyl konjak glucomannan, its total recovery is 59%.The method of using this specification sheets to describe has been measured the water-sol viscosity and the stability of the Nutgalls acyl konjak glucomannan of present embodiment preparation, its result's difference 0.9 * 10
-3Pas and 5 days.
Claims (10)
1. the preparation method of a Nutgalls acyl konjak glucomannan is characterized in that this method comprises the steps:
A) preparation triacetyl gallic acid
Gallic acid, diacetyl oxide and anhydrous pyridine react 10～15h according to mol ratio 1: 2～6: 2～6 under the condition of 22～28 ℃ of temperature; Dilute with zero(ppm) water then; Then adding concentrated hydrochloric acid is adjusted to pH 0.8～12 with its solution and o'clock generates a kind of deposition; Use cold water washing through filtering the throw out that obtains after the separation, dry again, obtain the triacetyl gallic acid of white powder to constant weight.
B) preparation triacetyl Nutgalls acyl chlorides
Steps A) the triacetyl gallic acid and the sulfur oxychloride of preparation react 2～6h according to mol ratio 1: 1～5 under the condition of 70～90 ℃ of temperature; Remaining sulfur oxychloride is removed in underpressure distillation then; The solid abrasive powdered that obtains; Follow vacuum-drying 10～15h, obtain the triacetyl Nutgalls acyl chlorides of white powder.
C) preparation triacetyl Nutgalls acyl konjak glucomannan
The konjak glucomannan raw material with the anhydrous pyridine solvent-swollen after; In the presence of the anhydrous pyridine solvent, be added in step B then) the triacetyl Nutgalls acyl chlorides that obtains; The mass ratio 1: 1～4 of its konjak glucomannan and triacetyl Nutgalls acyl chlorides reacts 1.2～1.8h under the condition of 45～55 ℃ of temperature, then whole reaction system is cooled to room temperature; Dilute with absolute ethyl alcohol again; The throw out that obtains is used absolute ethanol washing after separating, then be dried to constant weight, obtains triacetyl Nutgalls acyl konjak glucomannan.
D) preparation Nutgalls acyl konjak glucomannan
According in mL saturated acetic acid sodium ethanol solution with in the ratio 20～60mL/g of g triacetyl Nutgalls acyl konjak glucomannan; With step C) preparation triacetyl Nutgalls acyl konjak glucomannan be dissolved in the saturated acetic acid sodium ethanol solution; At room temperature stir 0.8～1.2h, after separation and drying, obtain described Nutgalls acyl konjak glucomannan.
2. method according to claim 1 is characterized in that in steps A) in, gallic acid, diacetyl oxide and anhydrous pyridine react 11～13h according to mol ratio 1: 3～5: 3～5 under the condition of 24～26 ℃ of temperature.
3. method according to claim 1 is characterized in that in steps A) in, use the zero(ppm) water of 4～6 times of reaction soln volumes to dilute.
4. method according to claim 1 is characterized in that in steps A) in, dry to constant weight under the condition of 55～65 ℃ of temperature with the throw out of cold water washing.
5. method according to claim 1 is characterized in that at step B) in, triacetyl gallic acid and sulfur oxychloride react 3～5h according to mol ratio 1: 2～4 under the condition of 75～85 ℃ of temperature.
6. method according to claim 1; It is characterized in that at step B) in; After the reaction of triacetyl gallic acid and sulfur oxychloride finished, this reactant carried out underpressure distillation under 50～70 ℃ condition, and the pressed powder that obtains is dry 12～14h under 0.01～0.1MPa vacuum.
7. method according to claim 1 is characterized in that at step C) in, triacetyl Nutgalls acyl chlorides and konjak glucomannan react 1.4～1.6h under the condition of 48～52 ℃ of its mass ratio 1: 2～3 and temperature.
8. method according to claim 1 is characterized in that at step C) in, dry to constant weight under the condition of 55～65 ℃ of temperature with the throw out of absolute ethanol washing.
9. method according to claim 1 is characterized in that step D) in, according in mL saturated acetic acid sodium ethanol solution be 30～50mL/g in the ratio of g triacetyl Nutgalls acyl konjak glucomannan.
10. method according to claim 1 is characterized in that at step D) in, under the condition of 55～65 ℃ of temperature, carry out drying.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102936296A (en) * | 2012-12-06 | 2013-02-20 | 承德天创生物制品有限公司 | Preparation method for galloyl konjac glucomannan |
| CN104610469A (en) * | 2015-03-08 | 2015-05-13 | 桂林理工大学 | Synthesis method for anti-staphylococcus aureus double-activity gallic acid-sulfated bagasse xylan |
| CN107417806A (en) * | 2017-07-20 | 2017-12-01 | 河南科技学院 | A kind of preparation method of the gallic acid glucan oligimer with α glucosidase inhibitory actives |
| CN112048028A (en) * | 2020-09-24 | 2020-12-08 | 江南大学 | Light-stable modified curdlan antioxidant and preparation method and application thereof |
-
2012
- 2012-04-11 CN CN201210104196XA patent/CN102627701A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| 张佳琪等: "没食子酸对魔芋葡甘露聚糖的酯化改性研究", 《天然产物研究与开发》 * |
| 王文晟等: "没食子酸（TNC）对魔芋葡甘聚糖干法改性的研究", 《食品科学》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102936296A (en) * | 2012-12-06 | 2013-02-20 | 承德天创生物制品有限公司 | Preparation method for galloyl konjac glucomannan |
| CN102936296B (en) * | 2012-12-06 | 2014-12-10 | 承德天创生物制品有限公司 | Preparation method for galloyl konjac glucomannan |
| CN104610469A (en) * | 2015-03-08 | 2015-05-13 | 桂林理工大学 | Synthesis method for anti-staphylococcus aureus double-activity gallic acid-sulfated bagasse xylan |
| CN107417806A (en) * | 2017-07-20 | 2017-12-01 | 河南科技学院 | A kind of preparation method of the gallic acid glucan oligimer with α glucosidase inhibitory actives |
| CN112048028A (en) * | 2020-09-24 | 2020-12-08 | 江南大学 | Light-stable modified curdlan antioxidant and preparation method and application thereof |
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Application publication date: 20120808 |