CN109485751A - A kind of synthetic method of 3,4,5-trihydroxy benzoic acid base bagasse xylan phthalic acid ester - Google Patents
A kind of synthetic method of 3,4,5-trihydroxy benzoic acid base bagasse xylan phthalic acid ester Download PDFInfo
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- CN109485751A CN109485751A CN201811225988.6A CN201811225988A CN109485751A CN 109485751 A CN109485751 A CN 109485751A CN 201811225988 A CN201811225988 A CN 201811225988A CN 109485751 A CN109485751 A CN 109485751A
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- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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Abstract
The invention discloses a kind of synthetic methods of 3,4,5-trihydroxy benzoic acid base bagasse xylan phthalic acid ester.Using bagasse xylan as primary raw material,N,N‑Dimethylformamide is reaction dissolvent, and triethylamine is catalyst, and bagasse xylan phthalic acid ester is synthesized with phthalic anhydride.It in pyridine solvent, is successively reacted with acetic anhydride and hydrochloric acid with trihydroxybenzoic acid, synthesizes triacetyl chlorobenzoyl chloride.Then using acetone as reaction dissolvent, by bagasse xylan phthalic acid ester and triacetyl chlorobenzoyl chloride under phosphomolybdic acid catalytic action, double esterification derivative Gallic Acid base bagasse xylan phthalic acid ester is synthesized through second step esterification.Condition of the present invention is easily controllable, and product bioactivity is significantly improved compared with reactant, has broader practice space in terms of medicine, food, the potential using value with higher in antiviral, AntiHIV1 RT activity field.
Description
Technical field
The present invention relates to high-molecular biologic material fields, and in particular to a kind of Gallic Acid base bagasse wood
The synthetic method of glycan phthalic acid ester.
Background technique
Bagasse xylan is a kind of stabilization, hemicellulose that is nontoxic and having the functions such as stimulation Culture in vitro, is had
Good development and application prospect, usually expands the application range of xylan by chemical modification, and esterification is that xylan is common
One of method of modifying.Double esterification reaction can introduce two kinds of new functional groups in xylan main body, more fully utilize
Two active lateral groups of xylan, significantly increase the bioactivity of xylan.
Esterification about groups such as bagasse xylan ester and sulfuric acid, phosphoric acid, sulfonic acid has had corresponding research, ester
Changing product has apparent HIV-resistant activity.The present invention by bagasse xylan and 3,4,5-trihydroxy benzoic acid, phthalic acid into
Two step esterification of row, can make full use of the anti-inflammatory of two kinds of esterified groups, antibacterial and HIV-resistant activity.By introducing acidic groups
Group can be enhanced the biocompatibility of xylan, product medicine, in terms of be with a wide range of applications.
For the present invention using bagasse xylan as primary raw material, n,N-Dimethylformamide is reaction dissolvent, and triethylamine is catalysis
Agent synthesizes bagasse xylan phthalic acid ester with phthalic anhydride.In pyridine solvent, with trihydroxybenzoic acid
It is successively reacted with acetic anhydride and hydrochloric acid, synthesizes triacetyl chlorobenzoyl chloride.Then using acetone as reaction dissolvent, by bagasse xylan neighbour
Phthalic acid ester and triacetyl chlorobenzoyl chloride synthesize double esterification derivative under phosphomolybdic acid catalytic action, through second step esterification
3,4,5-trihydroxy benzoic acid base bagasse xylan phthalic acid ester.
Summary of the invention
The purpose of the present invention is improving the HIV-resistant activity of bagasse xylan, a kind of Gallic Acid base is provided
The synthetic method of bagasse xylan phthalic acid ester.
Specific steps of the invention are as follows:
(1) 6~8g bagasse xylan is 24 hours dry in 50 DEG C of vacuum drying ovens, it is poly- to obtain butt bagasse wood
Sugar.
(2) gained butt bagasse xylan in 4~6g step (1) is weighed to be added in 250mL four-hole boiling flask, addition 20~
35mL analyzes pure n,N-Dimethylformamide (DMF), is added with stirring 1~2mL and analyzes pure triethylamine, continues stirring 30 minutes,
It is warming up to 80 DEG C.
(3) successively by 3~6g phthalic anhydride, 10~20mL analyzes pure DMF and is added in 50mL beaker, pours into after dissolution
In constant pressure funnel.The solution is added drop-wise in step (2) reaction system under stirring, control time for adding at 2~3 hours,
The reaction was continued 5 hours after being added dropwise.
(4) will be filtered after the cooling of reaction solution obtained by step (3), respectively with 10~15mL dehydrated alcohol, analyze pure acetone and
Deionized water washing, then filter to obtain filter cake.Filter cake is placed in 50 DEG C of vacuum drying oven dry 24 hours to get bagasse wood
Glycan phthalic acid ester.
(5) 8~10g Gallic Acid is weighed to be added in the 250mL four-hole boiling flask with reflux condenser,
13~22mL is added and analyzes pure acetic anhydride and 11~16mL analysis pure pyridine, control reaction temperature is 20~25 DEG C, anti-under stirring
It answers 8~12 hours.The continuous hydrochloric acid solution that 20~40mL mass fraction is added and is 20%~30% of lower system relaying is stirred, obtains 3,4,
5- triacetyl benzoic acid crude product.
(6) gained crude product in step (5) is filtered, and filter cake is placed in 100mL beaker, with 10~15mL's
Deionized water washing is precipitated and is filtered, and after being repeated 3 times, filter cake is placed in drying 24 hours in 50 DEG C of vacuum drying oven,
Obtain 3,4,5- triacetyl benzoic acid.
(7) it weighs 3,4,5- triacetyl benzoic acid obtained by 5~10g step (6) to be added in 250mL four-hole boiling flask, be added
30~50mL analyzes pure hexamethylene and 1~2mL analyzes pure DMF, and after mixing evenly, system is warming up to 60~80 DEG C, stirs lower drop
15~45mL is added to analyze pure thionyl chloride, control is added dropwise in 20~30 minutes, continue to be stirred to react 2 after being added dropwise~
4 hours, obtain the thick mixed liquor of triacetyl chlorobenzoyl chloride.
(8) reaction solution obtained by step (7) being poured into and carries out rotary evaporation in flask, control bath temperature is 50~60 DEG C,
Evaporation 20~60 minutes.Evaporation remaining solid is placed in drying 24 hours in 50 DEG C of thermostatic drying chamber, obtains 3,4,5- triacetyls
Chlorobenzoyl chloride.
(9) the resulting bagasse xylan phthalic acid ester of 5~10g step (4) is weighed, 3,4 obtained by 5~9g step (8),
5- triacetyl chlorobenzoyl chloride, is added in the four-hole boiling flask of 250mL, add 35~60mL analysis pure acetone and 0.05~
0.2g phosphomolybdic acid, system are warming up to 60~80 DEG C, stir lower reaction 3~8 hours.
(10) reaction solution obtained by step (9) is filtered, filter cake is in 100mL beaker every time with 10~15mL sodium bicarbonate
Alcohol saturated solution washing is precipitated and is filtered, and after being repeated 3 times, filter cake is put into surface plate, and it is dry to be placed in 50 DEG C of constant-temperature vacuums
24 hours are dried in case to get product Gallic Acid base bagasse xylan phthalic acid ester.
(11) carboxylic esterification degree of substitution, operation side are carried out using determination of acid-basetitration bagasse xylan double esterification derivative
Method is as follows: the Product samples of precise about 0.5g are put into 250mL conical flask, and 5mL deionized water is added, then instills several
Drip phenolphthalein indicator.The sodium hydroxide solution of 2.5mL 0.5mol/L is added, shakes up.Concussion saponification 1 hour at 20 DEG C.With
10mL deionized water rinses the inner wall of plug and conical flask, then be titrated to 0.5mol/L hydrochloric acid standard solution it is colourless, as eventually
Point.The volume V of record consumption hydrochloric acid standard solution1.Under the same conditions, blank drop is carried out with the bagasse xylan before esterification
It is fixed, record consumption hydrochloric acid standard solution volume V0.The calculation formula of carboxylic esterification degree of substitution (DS) is as follows:
In formula: Wc --- contain the mass fraction of ester carbonyl group, % in double esterification bagasse xylan；
V0--- titration bagasse xylan uses HCI standard solution volume, Unit/mL；
V1--- HCl standard solution volume used in titration mark product, Unit/mL；
CHCl--- the concentration of HCl, unit mol/L；
M --- sample quality, unit g；
M --- acyl group is dehydrated the relative molecular mass of xylose units, unit g/mol；
132 --- the relative molecular mass of bagasse xylan dewatering unit, unit g/mol；
DS --- ester carbonyl group degree of substitution.
The present invention has disubstituted 3,4,5-trihydroxy benzoic acid base bagasse wood poly- by the synthesis of secondary esterification
The introducing of sugared phthalic acid ester, two kinds of active groups enhances the antiviral activity of bagasse xylan, in terms of have
There is higher potential using value.
Detailed description of the invention
Fig. 1 is the SEM photograph of former bagasse xylan.
Fig. 2 is the SEM photograph of 3,4,5-trihydroxy benzoic acid base bagasse xylan isophthalic acid ester.
Fig. 3 is the IR figure of former bagasse xylan.
Fig. 4 is that the IR of 3,4,5-trihydroxy benzoic acid base bagasse xylan isophthalic acid ester schemes.
Fig. 5 is the XRD diagram of former bagasse xylan.
Fig. 6 is the XRD diagram of 3,4,5-trihydroxy benzoic acid base bagasse xylan isophthalic acid ester.
Fig. 7 is TG the and DTG curve of former bagasse xylan.
Fig. 8 is TG the and DTG curve of 3,4,5-trihydroxy benzoic acid base bagasse xylan isophthalic acid ester.
Specific embodiment
Embodiment:
(1) 8g bagasse xylan is 24 hours dry in 50 DEG C of vacuum drying ovens, obtain butt bagasse xylan.
(2) it weighs gained butt bagasse xylan in 5g step (1) to be added in 250mL four-hole boiling flask, 25mL analysis is added
Pure n,N-Dimethylformamide (DMF) is added with stirring 1mL and analyzes pure triethylamine, continues stirring 30 minutes, be warming up to 80 DEG C.
(3) successively by 5g phthalic anhydride, 15mL analyzes pure DMF and is added in 50mL beaker, and constant pressure drop is poured into after dissolution
In liquid funnel.The solution is added drop-wise in step (2) reaction system under stirring, time for adding is controlled at 2~3 hours, drips
The reaction was continued 5 hours after finishing.
(4) will be filtered after the cooling of reaction solution obtained by step (3), respectively with 15mL dehydrated alcohol, analysis pure acetone and go from
Sub- water washing, then filter to obtain filter cake.Filter cake is placed in 50 DEG C of vacuum drying oven dry 24 hours to get bagasse xylan
Phthalic acid ester.
(5) it weighs 8g Gallic Acid to be added in the 250mL four-hole boiling flask with reflux condenser, be added
15mL analyzes pure acetic anhydride and 12mL analyzes pure pyridine, and control reaction temperature is 25 DEG C, stirs lower reaction 8 hours.Stir lower body
The hydrochloric acid solution that 20mL mass fraction is 25% is continuously added in system, obtains 3,4,5- triacetyl benzoic acid crude products.
(6) gained crude product in step (5) is filtered, and filter cake is placed in 100mL beaker, with 15mL go from
Sub- water washing is precipitated and is filtered, and after being repeated 3 times, filter cake is placed in drying 24 hours in 50 DEG C of vacuum drying oven, obtains 3,
4,5- triacetyl benzoic acid.
(7) it weighs 3,4,5- triacetyl benzoic acid obtained by 8g step (6) to be added in 250mL four-hole boiling flask, 35mL is added
It analyzes pure hexamethylene and 1mL analyzes pure DMF, after mixing evenly, system is warming up to 65 DEG C, stirs lower dropwise addition 25mL and analyzes pure dichloro
Sulfoxide, control are added dropwise in 30 minutes, continue to be stirred to react 3 hours after being added dropwise, obtain triacetyl chlorobenzoyl chloride and slightly mix
Close liquid.
(8) reaction solution obtained by step (7) is poured into and carries out rotary evaporation in flask, control bath temperature is 50 DEG C, evaporation
30 minutes.Evaporation remaining solid is placed in drying 24 hours in 50 DEG C of thermostatic drying chamber, obtains 3,4,5- triacetyl chlorobenzoyl chlorides.
(9) the resulting bagasse xylan phthalic acid ester of 8g step (4), 3,4,5-, tri- second obtained by 8g step (8) are weighed
Acyl chlorobenzoyl chloride, is added in the four-hole boiling flask of 250mL, adds the analysis pure acetone and 0.15g phosphomolybdic acid of 50mL, system liter
Temperature stirs lower reaction 4 hours to 70 DEG C.
(10) reaction solution obtained by step (9) is filtered, filter cake uses the ethyl alcohol of 15mL sodium bicarbonate every time in 100mL beaker
Saturated solution washing is precipitated and is filtered, and after being repeated 3 times, filter cake is put into surface plate, is placed in 50 DEG C of vacuum drying ovens
Dry 24 hours to get product Gallic Acid base bagasse xylan phthalic acid ester.
(11) esterification of the acid-base titration to 3,4,5-trihydroxy benzoic acid base bagasse xylan phthalic acid ester is used
Degree is measured, and measures DS=0.57.
Product is analyzed through IR it is found that in 3000~3700cm-1Section log glycan and double activated 3,4,5- trihydroxy benzene first
Acidic group bagasse xylan phthalic acid ester has a stronger eigen vibration peak, belongs to O-H stretching vibration peak.Compare bagasse
The XRD diagram of xylan and the XRD diagram and diffraction of double activated 3,4,5-trihydroxy benzoic acid base bagasse xylan phthalic acid ester
Data learn, the angles of diffraction of double esterification derivative products 9.1 °, 12.3 °, 13.4 °, 19.7 °, 20.5 °, 21.8 °, 24.2 °,
The characteristic diffraction peak of 27.2 °, 28.9 °, 32.3 ° etc. appearance is obvious, and the more former bagasse xylan of intensity is high.Especially 12.3 °,
Spike at 20.5 ° and 28.9 ° is remarkably reinforced, and total peak area increased, and illustrates xylan derivative after chemical modification
The systematicness of molecules align is more orderly, and crystallinity also increases, and crystal region increased significantly than log glycan, illustrates log
A degree of variation has occurred in the structure of glycan.According to thermogravimetric analysis, from TG and the DTG comparison of product and former bagasse xylan
Figure illustrates the heat of double esterification product it is found that be all varied in the decomposition rate in second, third stage, the ratio of mass loss
Stability is improved.
Claims (1)
1. a kind of synthetic method of Gallic Acid base bagasse xylan phthalic acid ester, it is characterised in that specific
Step are as follows:
(1) 6 ~ 8g bagasse xylan is 24 hours dry in 50 DEG C of vacuum drying ovens, obtain butt bagasse xylan；
(2) it weighs gained butt bagasse xylan in 4 ~ 6g step (1) to be added in 250mL four-hole boiling flask, 20 ~ 35mL analysis is added
It is pureN,N-Dimethylformamide is added with stirring 1 ~ 2mL and analyzes pure triethylamine, continues stirring 30 minutes, be warming up to 80 DEG C；
(3) successively by 3 ~ 6g phthalic anhydride, 10 ~ 20mL analysis is pureN,N-Dimethylformamide is added in 50mL beaker, molten
It is poured into constant pressure funnel after solution；The solution is added drop-wise in step (2) reaction system under stirring, control time for adding 2 ~
3 hours, the reaction was continued 5 hours after being added dropwise；
(4) it will be filtered after the cooling of reaction solution obtained by step (3), respectively with 10 ~ 15mL dehydrated alcohol, analysis pure acetone and deionization
Water washing, then filter to obtain filter cake；Filter cake is placed in 50 DEG C of vacuum drying oven dry 24 hours to get bagasse xylan neighbour
Phthalic acid ester；
(5) it weighs 8 ~ 10g Gallic Acid to be added in the 250mL four-hole boiling flask with reflux condenser, is added 13
~ 22mL analyzes pure acetic anhydride and 11 ~ 16mL analyzes pure pyridine, and control reaction temperature is 20 ~ 25 DEG C, and it is small to stir lower reaction 8 ~ 12
When；The continuous hydrochloric acid solution that 20 ~ 40mL mass fraction is added and is 20% ~ 30% of lower system relaying is stirred, 3,4,5- triacetyl benzene first are obtained
Sour crude product；
(6) gained crude product in step (5) is filtered, and filter cake is placed in 100mL beaker, with 10 ~ 15mL go from
Sub- water washing is precipitated and is filtered, and after being repeated 3 times, filter cake is placed in drying 24 hours in 50 DEG C of vacuum drying oven, obtains 3,
4,5- triacetyl benzoic acid；
(7) 3,4,5- triacetyl benzoic acid obtained by 5 ~ 10g step (6) is weighed to be added in 250mL four-hole boiling flask, addition 30 ~
50mL analyzes pure hexamethylene and 1 ~ 2mL analyzes pure DMF, and after mixing evenly, system is warming up to 60 ~ 80 DEG C, stir it is lower be added dropwise 15 ~
45mL analyzes pure thionyl chloride, and control is added dropwise in 20 ~ 30 minutes, continues to be stirred to react 2 ~ 4 hours after being added dropwise, obtain
The thick mixed liquor of triacetyl chlorobenzoyl chloride；
(8) reaction solution obtained by step (7) is poured into and carries out rotary evaporation in flask, control bath temperature is 50 ~ 60 DEG C, evaporation 20
~ 60 minutes；Evaporation remaining solid is placed in drying 24 hours in 50 DEG C of thermostatic drying chamber, obtains 3,4,5- triacetyl benzoyls
Chlorine；
(9) the resulting bagasse xylan phthalic acid ester of 5 ~ 10g step (4), 3,4,5- tri- obtained by 5 ~ 9 g steps (8) are weighed
Acetyl chlorobenzoyl chloride, is added in the four-hole boiling flask of 250mL, adds the analysis pure acetone and 0.05 ~ 0.2g phosphorus molybdenum of 35 ~ 60mL
Acid, system are warming up to 60 ~ 80 DEG C, stir lower reaction 3 ~ 8 hours；
(10) reaction solution obtained by step (9) is filtered, filter cake is in 100mL beaker every time with the ethyl alcohol of 10 ~ 15mL sodium bicarbonate
Saturated solution washing is precipitated and is filtered, and after being repeated 3 times, filter cake is put into surface plate, is placed in 50 DEG C of vacuum drying ovens
Dry 24 hours to get product Gallic Acid base bagasse xylan phthalic acid ester.
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| CN201811225988.6A CN109485751A (en) | 2018-10-21 | 2018-10-21 | A kind of synthetic method of 3,4,5-trihydroxy benzoic acid base bagasse xylan phthalic acid ester |
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| CN201811225988.6A CN109485751A (en) | 2018-10-21 | 2018-10-21 | A kind of synthetic method of 3,4,5-trihydroxy benzoic acid base bagasse xylan phthalic acid ester |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104530263A (en) * | 2014-12-17 | 2015-04-22 | 桂林理工大学 | Preparation method of gallic acid-bagasse xylan ester |
| 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 |
| CN104628882A (en) * | 2015-03-08 | 2015-05-20 | 桂林理工大学 | Synthetic method of sulfo bagasse xylan phthalate |
| CN107722142A (en) * | 2017-10-01 | 2018-02-23 | 桂林理工大学 | A kind of synthetic method of HIV-resistant activity sulfonic group bagasse xylan to ferrocene benzoic ether |
-
2018
- 2018-10-21 CN CN201811225988.6A patent/CN109485751A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104530263A (en) * | 2014-12-17 | 2015-04-22 | 桂林理工大学 | Preparation method of gallic acid-bagasse xylan ester |
| 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 |
| CN104628882A (en) * | 2015-03-08 | 2015-05-20 | 桂林理工大学 | Synthetic method of sulfo bagasse xylan phthalate |
| CN107722142A (en) * | 2017-10-01 | 2018-02-23 | 桂林理工大学 | A kind of synthetic method of HIV-resistant activity sulfonic group bagasse xylan to ferrocene benzoic ether |
Non-Patent Citations (1)
| Title |
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| 李和平等: ""双活性磺酸基蔗渣木聚糖邻苯二甲酸酯的合成与表征"", 《化学反应工程与工艺》 * |
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