CN109320632A - A kind of synthetic method of bagasse xylan gallic acid trimesic acid double esterification derivative - Google Patents
A kind of synthetic method of bagasse xylan gallic acid trimesic acid double esterification derivative Download PDFInfo
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Abstract
The invention discloses a kind of synthetic methods of bagasse xylan gallic acid trimesic acid double esterification derivative.Using bagasse xylan as raw material, n,N-Dimethylformamide is solvent, and ammonium persulfate is catalyst, carries out catalytic esterification with triacetyl Chinese gall acyl chlorides first and synthesizes bagasse xylan gallic acid ester；Again in n,N-Dimethylformamide solvent, in the presence of dehydrating agent N, N- dicyclohexylcarbodiimide, second step catalytic esterification is carried out with trimesic acid through cobalt naphthenate catalysis, synthesizes bagasse xylan gallic acid trimesic acid double esterification derivative.The bagasse xylan double esterification derivative has both the double activity of bagasse xylan gallic acid ester and bagasse xylan trimesic acid ester.Double activated bagasse xylan derivative by chemical modification HIV-resistant activity, anticoagulant active and in terms of tool have certain effect, in fields application values with higher such as medicine, food and fine chemistry industries.
Description
Technical field
The invention belongs to technical field of polymer materials, more particularly to a kind of bagasse xylan gallic acid trimesic acid
The synthetic method of double esterification derivative.
Background technique
Xylan in plant resources such as corncob, bagasse, cotton seed hulls, rice husk, straw, oil tea shell and birch content compared with
It is high.For the application range for expanding xylan, researcher carries out a variety of chemical methodes to xylan and is modified, and can not only overcome wood
The water-soluble poor defect of glycan itself, but also the original some chemical property of xylan and physiological activity can be enhanced, very
The property and bioactivity that xylan itself does not have can extremely be expanded.
The chemical modification of bagasse xylan occurs mainly in active C2, C3 hydroxyl position of comparison, structural modification method master
There are the methods of esterification, oxidation, etherificate, grafting and carboxy methylation.Studies have shown that xylan gallic acid ester have antibiotic property and
HIV-resistant activity, but a kind of activity against organisms group is only introduced in the xylan gallic acid ester of mono-esterification, make its activity against organisms
Ability is limited.There are also a large amount of unsubstituted hydroxyls in the structural unit of xylan gallic acid ester, if in synthesis xylan five
It is re-introduced into a kind of new active group on the basis of galate, will further improve its activity against organisms.Trimesic acid is
One kind is used to prepare fungicide, mould inhibitor, plasticizer and crosslinking agent, also be used to manufacture height containing there are three the organic acid of carboxyl
The fields such as molecular separation membrane, medicine intermediate.Trimesic acid group is introduced into xylan gallic acid ester, not only remains five
The original HIV-resistant activity of gall nut acid, while also having the biological nature of trimesic acid, so that its activity against organisms is improved,
It is widened in the application in the fields such as medicine, fine chemistry industry, environment.
For the present invention using bagasse xylan as primary raw material, n,N-Dimethylformamide (DMF) is solvent, and ammonium persulfate is to urge
Agent carries out catalytic esterification with the chloride product triacetyl Chinese gall acyl chlorides of gallic acid first and synthesizes bagasse xylan
Gallic acid ester；Again in n,N-Dimethylformamide solvent, in the presence of dehydrating agent N, N- dicyclohexylcarbodiimide, through cycloalkanes
Sour cobalt catalysis carries out second step catalytic esterification with trimesic acid, and synthesis bagasse xylan gallic acid trimesic acid is double
Esterification derivative.The bagasse xylan double esterification derivative has both bagasse xylan gallic acid ester and the equal benzene three of bagasse xylan
The double activity of formic acid esters.
Summary of the invention
The purpose of the invention is to improve the bioactivity of bagasse xylan and functional characteristic, expands application range, mention
It is double further to develop xylan for a kind of preparation method of bagasse xylan gallic acid trimesic acid double esterification derivative
Esterification class anti-AIDS class drug provides certain foundation and reference.
Specific steps of the invention are as follows:
(1) it weighs 10~15g gallic acid to be added in 250mL four-hole boiling flask, and it is pure that 15~20mL analysis is added thereto
Acetic anhydride and 12~15mL analyze pure pyridine, and control ice bath temperature is 10~25 DEG C, stir lower reaction 8~10 hours.It is added 22
The hydrochloric acid solution that~35mL mass fraction is 20%~30% stirs evenly and white precipitate triacetyl gallic acid crude product is precipitated.
(2) triacetyl gallic acid crude product obtained by step (1) is filtered, and sufficiently washs precipitating 3 with 10~15mL distilled water
It is filtered after secondary, filter cake send into 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains triacetyl gallic acid.
(3) it weighs triacetyl gallic acid obtained by 8~10g step (2) to be added in 250mL four-hole boiling flask, and adds thereto
Enter 30~45mL and analyze pure hexamethylene and the pure n,N-Dimethylformamide of 20~40mL analysis, is stirred at reflux 30~40 minutes.
(4) step (3) reaction system is warming up to 65~80 DEG C, starts 20~40mL of dropwise addition and analyzes pure thionyl chloride, control
System is added dropwise in 25~35 minutes, and the reaction was continued 2~4 hours.
(5) step (4) acquired solution is poured into Rotary Evaporators, 30~70 is concentrated by evaporation under conditions of 60~80 DEG C
Minute, obtain the solid of brownish red.It puts it into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to perseverance
Weight, obtains triacetyl Chinese gall acyl chlorides.
(6) triacetyl Chinese gall acyl chlorides obtained by 1.5~4.0g step (5) is weighed in 100mL beaker, and 20~35mL is added
Pure n,N-Dimethylformamide is analyzed, 35~40 DEG C are heated in water-bath, stirring and dissolving obtains triacetyl Chinese gall solution of acid chloride.It sets
It is spare in 100mL constant pressure funnel.
(7) 3~5g butt bagasse xylan is weighed in 250mL four-hole boiling flask, and 10~15mL is then added and analyzes pure N,
Dinethylformamide, 1~3g dehydrating agent N, N- dicyclohexylcarbodiimide, 0.03~0.6g catalyst ammonium persulfate, stirring
30 minutes.
(8) step (6) acquired solution is slowly added into system obtained by step (7)；It flows back under the conditions of 60 DEG C, continuously
Reaction 4 hours.
(9) step (8) resulting material is filtered, and respectively successively with the analysis of 10~20mL analysis pure acetone, 20~30mL
Pure dehydrated alcohol is respectively washed, is filtered 3 times, obtains filter cake.
(10) filter cake obtained by step (9) is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get three
Acetyl bagasse xylan gallic acid ester.
(11) bagasse xylan triacetyl gallic acid ester obtained by 4~6g step (10) is weighed in 40~60mL sodium bicarbonate
Dehydrated alcohol saturated solution in；It is stirred at room temperature, until pH of suspension is no longer changed.
(12) suspension obtained by step (11) is filtered, filter cake is distilled water washing 3 times with 15~20mL, is placed in 50 DEG C of vacuum
24 hours are dried in thermostatic drying chamber to constant weight to get bagasse xylan gallic acid ester.
(13) bagasse xylan gallic acid ester obtained by 3~5g step (12) is weighed to be placed in 250mL four-hole boiling flask, then according to
15~25mL of secondary addition analyzes pure n,N-Dimethylformamide, 1~3.5gN, N- dicyclohexylcarbodiimide and 0.02~0.15g
Catalyst cobalt naphthenate.
(14) 5~10g trimesic acid is weighed in 100mL beaker, and 20~30mL is added thereto and analyzes pure N, N-
Dimethylformamide is heated to 35~40 DEG C of stirring and dissolvings.
(15) step (14) acquired solution is placed in 100mL constant pressure funnel, and is slowly added into step (13) institute
In the system of obtaining, return stirring is carried out under conditions of 70~80 DEG C and is reacted 4 hours.It is cooled to room temperature, filter cake is filtered by vacuum to obtain.
(16) 10~20mL analysis pure acetone, 10~20mL is successively used to analyze pure dehydrated alcohol filter cake obtained by step (15)
Each washing filters 3 times.
(17) at room temperature, filter cake obtained by step (16) is added to the dehydrated alcohol saturated solution of 30~50mL sodium bicarbonate
In, it is stirred at room temperature, until pH of suspension is no longer changed.Continue successively with 15~20mL distilled water, 20~35mL points
It analyses pure dehydrated alcohol respectively to wash, filter 3 times, obtains bagasse xylan gallic acid trimesic acid double esterification derivative filter cake.
(18) filter cake step (17) obtained by is sent into 50 DEG C of vacuum constant temperature drying boxes to drying 24 hours to constant weight to get sugarcane
Slag xylan gallic acid trimesic acid double esterification derivative.
(19) carboxylate of determination of acid-basetitration bagasse xylan gallic acid trimesic acid double esterification derivative is used
Change degree of substitution, operating method is as follows: the Product samples of precise about 0.5g are placed in 250mL conical flask, be added 5mL go from
Then sub- water instills few drops of phenolphthalein indicators.The sodium hydroxide solution of 2.5mL 0.5mol/L is added, shakes up.It is shaken at 20 DEG C
Swing saponification 1 hour.The inner wall of plug and conical flask is rinsed with 10mL deionized water, then is titrated with 0.5mol/L hydrochloric acid standard solution
To colourless, as terminal.The volume V of record consumption hydrochloric acid standard solution1.Under the same conditions, poly- with the bagasse wood before esterification
Sugar carries out blank titration, 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；
The quality of m --- sample, 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 bagasse xylan gallic acid trimesic acid double esterification derivative synthesized using present invention process, process conditions
It is easily controllable, product bioactivity with higher, HIV-resistant activity.
Detailed description of the invention
Fig. 1 is the SEM photograph of bagasse xylan.
Fig. 2 is the SEM photograph of bagasse xylan gallic acid trimesic acid double esterification derivative.
Fig. 3 is original bagasse xylan IR figure.
Fig. 4 is that the IR of bagasse xylan gallic acid trimesic acid double esterification derivative schemes.
Fig. 5 is the XRD diagram of former bagasse xylan.
Fig. 6 is the XRD diagram of bagasse xylan gallic acid trimesic acid double esterification derivative.
Fig. 7 is TG the and DTG curve of former bagasse xylan.
Fig. 8 is TG the and DTG curve of bagasse xylan gallic acid trimesic acid double esterification derivative.
Specific embodiment
Embodiment:
(1) 10g gallic acid is weighed to be added in 250mL four-hole boiling flask, and be added thereto 20mL analyze pure acetic anhydride and
13mL analyzes pure pyridine, and control ice bath temperature is 20 DEG C, stirs lower reaction 8 hours.The salt that 22mL mass fraction is 20% is added
Acid solution stirs evenly and white precipitate triacetyl gallic acid crude product is precipitated.
(2) filter step (1) obtained by triacetyl gallic acid crude product, and with 10mL distilled water sufficiently wash precipitate 3 times after
It filters, filter cake send into 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains triacetyl gallic acid.
(3) it weighs triacetyl gallic acid obtained by 6g step (2) to be added in 250mL four-hole boiling flask, and is added thereto
30mL analyzes pure hexamethylene and 20mL analyzes pure n,N-Dimethylformamide, is stirred at reflux 40 minutes.
(4) step (3) reaction system is warming up to 65 DEG C, starts that the pure thionyl chloride of 20mL analysis is added dropwise, controls at 30 points
It is added dropwise in clock, the reaction was continued 2 hours.
(5) step (4) acquired solution is poured into Rotary Evaporators, is concentrated by evaporation 35 minutes, obtains under conditions of 60 DEG C
The solid of brownish red.It puts it into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains three second
Acyl Chinese gall acyl chlorides.
(6) triacetyl Chinese gall acyl chlorides obtained by 2g step (5) is weighed in 100mL beaker, and 30mL is added and analyzes pure N, N-
Dimethylformamide is heated to 40 DEG C in water-bath, and stirring and dissolving obtains triacetyl Chinese gall solution of acid chloride.It is placed in 100mL constant pressure drop
It is spare in liquid funnel.
(7) 3g butt bagasse xylan is weighed in 250mL four-hole boiling flask, and 10mL is then added and analyzes pure N, N- dimethyl
Formamide, 1g dehydrating agent N, N- dicyclohexylcarbodiimide, 0.03g catalyst ammonium persulfate stir 30 minutes.
(8) step (6) acquired solution is slowly added into system obtained by step (7)；It flows back under the conditions of 60 DEG C, continuously
Reaction 4 hours.
(9) step (8) resulting material is filtered, and respectively successively with the pure anhydrous second of analysis of 10mL analysis pure acetone, 20mL
Alcohol is respectively washed, is filtered 3 times, obtains filter cake.
(10) filter cake obtained by step (9) is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get three
Acetyl bagasse xylan gallic acid ester.
(11) bagasse xylan triacetyl gallic acid ester obtained by 4g step (10) is weighed in the anhydrous of 40mL sodium bicarbonate
In alcohol saturated solution；It is stirred at room temperature, until pH of suspension is no longer changed.
(12) suspension obtained by step (11) is filtered, filter cake is distilled water washing 3 times with 20mL, is placed in 50 DEG C of vacuum constant temperatures
24 hours are dried in drying box to constant weight to get bagasse xylan gallic acid ester.
(13) it weighs bagasse xylan gallic acid ester obtained by 5g step (12) to be placed in 250mL four-hole boiling flask, then successively
20mL is added and analyzes pure n,N-Dimethylformamide, 3.5gN, N- dicyclohexylcarbodiimide and 0.15g catalyst cobalt naphthenate.
(14) 6g trimesic acid is weighed in 100mL beaker, and 25mL is added thereto and analyzes pure N, N- dimethyl methyl
Amide is heated to 35 DEG C of stirring and dissolvings.
(15) step (14) acquired solution is placed in 100mL constant pressure funnel, and is slowly added into step (13) institute
In the system of obtaining, return stirring is carried out under conditions of 70 DEG C and is reacted 4 hours.It is cooled to room temperature, filter cake is filtered by vacuum to obtain.
(16) successively respectively wash filter cake obtained by step (15) with 10mL analysis pure acetone, the pure dehydrated alcohol of 15mL analysis,
It filters 3 times.
(17) at room temperature, filter cake obtained by step (16) is added in the dehydrated alcohol saturated solution of 30mL sodium bicarbonate,
It is stirred at room temperature, until pH of suspension is no longer changed.Continue successively to analyze pure dehydrated alcohol with 15mL distilled water, 20mL
Each washing filters 3 times, obtains bagasse xylan gallic acid trimesic acid double esterification derivative filter cake.
(18) filter cake step (17) obtained by is sent into 50 DEG C of vacuum constant temperature drying boxes to drying 24 hours to constant weight to get sugarcane
Slag xylan gallic acid trimesic acid double esterification derivative.
(19) measurement of carboxylic esterification degree of substitution is carried out to step (18) products therefrom using the method for acid base titration, obtains its carboxylic
Esterification degree of substitution is 0.81.
Product is analyzed through IR, 1629.86cm-1For carboxyl absorption peak, 1043.30cm-1For the absorption peak of C-O-C key, still
The absorption peak of O-H angle vibration, 1399.14cm-1It is the deformation vibration peak of C-H, 896.57cm-1For the vibration of xylan molecular skeleton
Dynamic peak, 1733.06cm-1And 1250cm-1There is new absorption peak in place, and corresponding is ester carbonyl group and phenolic hydroxyl group,
1575.94cm-1And 1536.94cm-1Locate mostly two characteristic absorption peaks, illustrates the presence of phenyl ring skeleton.Through XRD analysis,
7.61 °, 16.78 °, 22.80 °, 26.68 °, 29.45 ° this there is the higher and relatively narrow diffraction maximum of peak value at five, also in many places
There is the obvious diffraction maximum relatively concentrated, illustrates that crystallinity is very high, crystalline content is more, and crystal region is more complete.It is analyzed again through TG-DTG
Show that bagasse xylan double esterification is modified, 4 stages, first stage quality can be roughly divided into compared to former bagasse xylan
Mass loss is 6.63%；Second stage mass loss rate between 200 DEG C~300 DEG C reaches 18.16%, compares bagasse xylan
Loss amount it is low；It is 9.82% in 300 DEG C~450 DEG C mass losses, mass change is little after 450 DEG C, illustrates that wood is poly- at this time
Sugared diester derivatives are basically completed decomposition.Sem analysis shows that bagasse xylan gallic acid trimesic acid double esterification is derivative
The surface of object is not very complete, and broken an ancient egg-shaped, holed wind instrument rill and gap occurs, and apparent variation also has occurred in structure, and thus explanation is anti-
Should after the structure of xylan received destruction, it may occur however that double esterification, apparent property are changed.
Claims (1)
1. a kind of synthetic method of bagasse xylan gallic acid trimesic acid double esterification derivative, it is characterised in that specific step
Suddenly are as follows:
(1) it weighs 10 ~ 15g gallic acid to be added in 250 mL four-hole boiling flasks, and 15 ~ 20 mL is added thereto and analyze pure acetic acid
Acid anhydride and 12 ~ 15mL analyze pure pyridine, and control ice bath temperature is 10 ~ 25 DEG C, stir lower reaction 8 ~ 10 hours；22 ~ 35mL matter is added
The hydrochloric acid solution that score is 20% ~ 30% is measured, stirs evenly and white precipitate triacetyl gallic acid crude product is precipitated；
(2) filter step (1) obtained by triacetyl gallic acid crude product, and with 10 ~ 15 mL distilled water sufficiently wash precipitate 3 times after
It filters, filter cake send into 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains triacetyl gallic acid；
(3) it weighs triacetyl gallic acid obtained by 8 ~ 10 g steps (2) to be added in 250 mL four-hole boiling flasks, and 30 is added thereto
~ 45 mL analyze pure hexamethylene and 20 ~ 40mL analyzes pure n,N-Dimethylformamide, are stirred at reflux 30 ~ 40 minutes；
(4) step (3) reaction system is warming up to 65 ~ 80 DEG C, starts 20 ~ 40mL of dropwise addition and analyze pure thionyl chloride, control 25 ~
It is added dropwise in 35 minutes, the reaction was continued 2 ~ 4 hours；
(5) step (4) acquired solution is poured into Rotary Evaporators, is concentrated by evaporation 30 ~ 70 minutes under conditions of 60 ~ 80 DEG C,
Obtain the solid of brownish red；It puts it into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains three
Acetyl Chinese gall acyl chlorides；
(6) triacetyl Chinese gall acyl chlorides obtained by 1.5 ~ 4.0g step (5) is weighed in 100 mL beakers, is added 20 ~ 35 mL points
Pure n,N-Dimethylformamide is analysed, 35 ~ 40 DEG C are heated in water-bath, stirring and dissolving obtains triacetyl Chinese gall solution of acid chloride；It is placed in
It is spare in 100mL constant pressure funnel；
(7) 3 ~ 5 g butt bagasse xylans are weighed in 250 mL four-hole boiling flasks, 10 ~ 15 mL are then added and analyze pure N, N- bis-
Methylformamide, 1 ~ 3 g dehydrating agent N, N- dicyclohexylcarbodiimide, 0.03 ~ 0.6 g catalyst ammonium persulfate stir 30 points
Clock；
(8) step (6) acquired solution is slowly added into system obtained by step (7)；It flows back under the conditions of 60 DEG C, successive reaction
4 hours；
(9) step (8) resulting material is filtered, and respectively successively with the pure nothing of analysis of 10 ~ 20 mL analysis pure acetone, 20 ~ 30 mL
Water-ethanol is respectively washed, is filtered 3 times, obtains filter cake；
(10) filter cake obtained by step (9) is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get triacetyl
Bagasse xylan gallic acid ester；
(11) bagasse xylan triacetyl gallic acid ester obtained by 4 ~ 6 g steps (10) is weighed in the nothing of 40 ~ 60mL sodium bicarbonate
In water-ethanol saturated solution；It is stirred at room temperature, until pH of suspension is no longer changed；
(12) suspension obtained by step (11) is filtered, filter cake is distilled water washing 3 times with 15 ~ 20mL, is placed in 50 DEG C of vacuum constant temperatures
24 hours are dried in drying box to constant weight to get bagasse xylan gallic acid ester；
(13) it weighs bagasse xylan gallic acid ester obtained by 3 ~ 5g step (12) to be placed in 250 mL four-hole boiling flasks, then successively adds
Enter 15 ~ 25 mL and analyzes pure n,N-Dimethylformamide, 1 ~ 3.5gN, N- dicyclohexylcarbodiimide and 0.02 ~ 0.15 g catalysis
Agent cobalt naphthenate；
(14) 5 ~ 10g trimesic acid is weighed in 100mL beaker, and 20 ~ 30mL is added thereto and analyzes pure N, N- dimethyl
Formamide is heated to 35 ~ 40 DEG C of stirring and dissolvings；
(15) step (14) acquired solution is placed in 100mL constant pressure funnel, and it is proper to be slowly added into step (13) institute
In system, return stirring is carried out under conditions of 70 ~ 80 DEG C and is reacted 4 hours；It is cooled to room temperature, filter cake is filtered by vacuum to obtain；
(16) filter cake obtained by step (15) is successively analyzed pure dehydrated alcohol and is respectively washed with 10 ~ 20 mL analysis pure acetone, 10 ~ 20 mL
It washs, filter 3 times；
(17) at room temperature, filter cake obtained by step (16) is added in the dehydrated alcohol saturated solution of 30 ~ 50mL sodium bicarbonate,
It stirs at room temperature, until pH of suspension is no longer changed；Continue successively pure anhydrous with 15 ~ 20mL distilled water, 20 ~ 35mL analysis
Ethyl alcohol is respectively washed, is filtered 3 times, obtains bagasse xylan gallic acid trimesic acid double esterification derivative filter cake；
(18) filter cake obtained by step (17) is sent into 50 DEG C of vacuum constant temperature drying boxes and dries 24 hours to constant weight to get bagasse wood
Glycan gallic acid trimesic acid double esterification derivative.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106519079A (en) * | 2016-10-26 | 2017-03-22 | 桂林理工大学 | Synthetic method of anti-HIV-activity sulfonyl bagasse xylan polyethylene terephthalate |
| CN106565857A (en) * | 2016-10-26 | 2017-04-19 | 桂林理工大学 | Method for synthesizing double-active sulfo bagasse xylan isophthalate |
| CN107540789A (en) * | 2017-09-15 | 2018-01-05 | 桂林理工大学 | Biologically active derivatives bagasse xylan cloves acid esters g AM synthetic method |
| CN107586352A (en) * | 2017-10-01 | 2018-01-16 | 桂林理工大学 | A kind of preparation method with antitumor activity bagasse xylan gallic acid/ferulic acid ester |
-
2018
- 2018-10-21 CN CN201811225987.1A patent/CN109320632A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106519079A (en) * | 2016-10-26 | 2017-03-22 | 桂林理工大学 | Synthetic method of anti-HIV-activity sulfonyl bagasse xylan polyethylene terephthalate |
| CN106565857A (en) * | 2016-10-26 | 2017-04-19 | 桂林理工大学 | Method for synthesizing double-active sulfo bagasse xylan isophthalate |
| CN107540789A (en) * | 2017-09-15 | 2018-01-05 | 桂林理工大学 | Biologically active derivatives bagasse xylan cloves acid esters g AM synthetic method |
| CN107586352A (en) * | 2017-10-01 | 2018-01-16 | 桂林理工大学 | A kind of preparation method with antitumor activity bagasse xylan gallic acid/ferulic acid ester |
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