CN107586352A - A kind of preparation method with antitumor activity bagasse xylan gallic acid/ferulic acid ester - Google Patents
A kind of preparation method with antitumor activity bagasse xylan gallic acid/ferulic acid ester Download PDFInfo
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Abstract
The invention discloses a kind of preparation method with antitumor activity bagasse xylan gallic acid/ferulic acid ester.The triacetyl nutgall acyl chlorides that gallic acid is generated through acetylation, acyl chloride reaction first is esterifying agent, and bagasse xylan gallate is synthesized with bagasse xylan esterification in DMF organic solvent；Then the forulic acid for selecting high bioactivity chloride is second step esterifying agent, p-methyl benzenesulfonic acid is catalyst, secondary esterification is carried out with bagasse xylan gallate in acetone solvent, further bagasse xylan gallic acid/ferulic acid ester of the synthesis with antitumor activity.The product is filtered in sodium acid carbonate absolute ethyl alcohol saturated solution, washed, produces bagasse xylan double esterification derivative bagasse xylan gallic acid/ferulic acid ester of high substituted degree.Invention not only improves the bioactivity of xylan, while application of the xylan in fields such as medicine, biology and functional materials is also widened.
Description
Technical field
The invention belongs to technical field of fine, more particularly to a kind of antitumor activity bagasse xylan gallic acid/Ah
The preparation method of Wei's acid esters.
Background technology
In recent years, the development and utilization of renewable lignocellulose-like biomass resource obtains the very big concern of people, quilt
It is considered solve the effective way of fossil resources increasingly depleted and environmental problem.Wherein, hemicellulose is most abundant, most honest and clean on the earth
One of renewable resource of valency.And xylan is the main component of hemicellulose, but so far, xylan resource still without
To effective exploitation and utilization.How to be rationally the research of agricultural-forestry biomass resources effective utilization using with high-valued conversion xylan
Important directions.
Research shows, the activity against organisms that xylan esterification derivative can effectively improve xylan are for example antitumor, AntiHIV1 RT activity,
It is antiviral etc..Gallic acid monoesterified derivatives can be with induced tumor apoptosis, but it is independent of the cell cycle, but increases
Refinement intracellular H2O2Content, and and Ca2+Chelating, promotes DNA to be broken in nucleosome, so as to reach the work for killing cancer cell
With.If gallic acid activity against organisms group is introduced on the basis of bagasse xylan will further enhance the anti-of bagasse xylan
Tumor promotion, and to healthy cell not damaged.But bagasse xylan monoesterified derivatives still suffer from the defects of activity against organisms are low.
Forulic acid is the organic acid that pharmacological action is clear and definite, property is stable, toxicity is relatively low, possesses induction cancer cell decline effect, cell toxicant
The antitumor mechanisms such as effect, radiotherapy protective effect and Apoptosis.Using gallic acid and forulic acid to bagasse xylan
Double esterification modification is carried out, not only remains the original antitumor activity of gallic acid, while the biology for being also provided with forulic acid is special
Property.The introducing of two kinds of bio-active groups is expected to improve the original antitumor activity of bagasse xylan, for enhancing xylan
Medical value exploitation is significant.
The triacetyl nutgall acyl chlorides that gallic acid is generated through acetylation, acyl chloride reaction first is esterifying agent,
Esterification is carried out with bagasse xylan synthesize bagasse xylan gallic acid in N,N-dimethylformamide (DMA) organic solvent
Ester；Then the forulic acid for selecting high bioactivity chloride is second step esterifying agent, and p-methyl benzenesulfonic acid is catalyst, molten in acetone
Secondary esterification is carried out in agent with bagasse xylan gallate, further bagasse wood of the synthesis with antitumor activity is poly-
Sugared gallic acid/ferulic acid ester.Invention not only improves the bioactivity of xylan, while xylan is also widened and has cured
The application in the fields such as medicine, biology, functional material.
The content of the invention
The invention aims to by carrying out double esterification modification to bagasse xylan, lived with it is expected to improve its biology
Property, improve added value, widen application, there is provided a kind of preparation method of bagasse xylan gallic acid/ferulic acid ester.
The present invention's comprises the following steps that：
(1) 5~10g bagasse xylans are dried 24 hours to constant weight in 60 DEG C of vacuum constant temperature drying boxes, obtains butt sugarcane
Slag xylan.
(2) 15~25g gallic acids are added in 250mL four-hole boiling flask, and it is pure to add 13~22mL analyses thereto
Acetic anhydride and 11~16mL analysis pure pyridines, it is 5~25 DEG C to control ice bath temperature, stirs lower reaction 6~12 hours.
(3) reaction solution obtained by step (2) is transferred in 100mL beakers, stirring lower addition 20~40mL mass fractions is
20%~30% hydrochloric acid solution, white precipitate is separated out in beaker；White precipitate after filtering is distilled with 10~15mL and washed
Wash and 24 hours are dried in the vacuum constant temperature drying box for delivered to after precipitating 3 times 50 DEG C to constant weight, obtain triacetyl gallic acid.
(4) take triacetyl gallic acid obtained by 5~10g steps (3) to be added in 250mL four-hole boiling flask, add thereto
Enter 30~50mL and analyze pure hexamethylene and 0.1~0.5g analysis absolute dimethylformamide, be stirred at reflux 30 minutes, control reaction
Temperature is 60~80 DEG C, and 15~45mL is added dropwise under agitation and analyzes pure thionyl chloride, controls and was added dropwise in 20~30 minutes
Finish, continue stirring reaction after being added dropwise 2~4 hours.
(5) step (4) resulting material is poured into beaker, 40~60 is concentrated by evaporation under conditions of being 60~80 DEG C in temperature
Minute, light tan solid is obtained, the solid is placed in 50 DEG C of vacuum constant temperature drying box and dries 24 hours to constant weight, obtain triacetyl
Nutgall acyl chlorides.
(6) butt bagasse xylan obtained by weighing 3~8g steps (1) is added in 250mL four-hole boiling flasks, and adds 0.1
~0.3g p-methyl benzenesulfonic acid and 30~50mL analysis pure acetones, are stirred at reflux 30 minutes to obtain bagasse xylan suspension.
(7) triacetyl nutgall acyl chlorides obtained by weighing 2~4g steps (5) is added in reaction system obtained by step (6), is stirred
Mix down and be warming up to 30~55 DEG C, continue reaction 3~6 hours.
(8) step (7) resulting material is filtered, and it is pure anhydrous with 10~15mL distilled water and 5~10mL analyses successively respectively
Ethanol washing precipitation 2~3 times, obtains bagasse xylan triacetyl gallate.
(9) bagasse xylan triacetyl gallate obtained by step (8) is inserted into the anhydrous of 30~50mL sodium acid carbonates
10~30 minutes pH to solution are stirred in alcohol saturated solution, under normal temperature no longer to change.
(10) step (9) resulting material is filtered, and respectively with 50 DEG C of feeding after 10~15mL distillations water washing filter cake 3 times
24 hours are dried in vacuum constant temperature drying box to constant weight, obtains bagasse xylan gallate.
(11) 4~10g forulic acids are added in 250mL four-hole boiling flask, and is separately added into 13~22mL analyses thereto
Pure acetic anhydride and 11~16mL analyze pure pyridine, and it is 5~25 DEG C to control frozen water bath temperature, stir lower reaction 6~12 hours.
(12) reaction solution obtained by step (2) is transferred in 100mL beakers, stirs lower addition 20~40mL mass fractions
For 20%~30% hydrochloric acid solution, white precipitate is separated out.By white precipitate respectively with 10~15mL distillation water washings precipitation 3
Delivered to after secondary in 50 DEG C of vacuum constant temperature drying box and dry 24 hours to constant weight, obtain Acetyl-ferulic acid.
(13) take Acetyl-ferulic acid obtained by 5~10g steps (12) to be added in 250mL four-hole boiling flask, and add thereto
Enter 30~50mL and analyze pure hexamethylene and 0.1~0.3g analysis absolute dimethylformamide, stirred back under conditions of 60~80 DEG C
Stream 30 minutes, 20~40mL is added dropwise in stirring and analyzes pure thionyl chloride, controls and was added dropwise in 20~30 minutes, drips
Add and continue stirring reaction after finishing 2~4 hours.
(14) step (13) resulting material is poured into 100mL beakers, evaporated under conditions of being 60~80 DEG C in temperature dense
Contracting 30~50 minutes, obtains light tan solid, the solid is placed in 50 DEG C of vacuum constant temperature drying box and dries 24 hours to constant weight,
Obtain Acetylferuloyl Chloride.
(15) bagasse xylan gallate obtained by weighing 4~8g steps (10) is added in 250mL four-hole boiling flasks, and
0.1~0.3g p-methyl benzenesulfonic acid is added thereto, and 30~50mL analyzes pure DMF (DMA), stirs and match somebody with somebody
It is set to bagasse xylan gallate suspension.
(16) 2~5g Acetylferuloyl Chlorides are weighed to be added in the reaction system of step (15), stirs, is warming up to 40
~60 DEG C, react 3~6 hours.
(17) step (16) resulting material is filtered, and analyzes pure nothing with 10~15mL distilled water and 5~10mL successively respectively
Water-ethanol washing filter cake 2~3 times, obtains bagasse xylan gallic acid/Acetyl-ferulic acid ester.
(18) bagasse xylan gallic acid/Acetyl-ferulic acid ester obtained by step (17) is inserted into 30~50mL bicarbonates
10~20 minutes pH to solution are stirred in the absolute ethyl alcohol saturated solution of sodium, under normal temperature not change.
(19) step (18) resulting material is filtered, 50 DEG C are sent into after being precipitated 3 times with 10~15mL distillation water washings respectively
24 hours are dried in vacuum constant temperature drying box to constant weight, produces bagasse xylan gallic acid/ferulic acid ester.
(20) using the galloyl of gained bagasse xylan gallate in determination of acid-basetitration step (10)
Substitution value.Specific method and step are as follows：Accurately weigh 0.5g samples to be placed in 50mL conical flasks, add 10mL distilled water, shake
It is even, the phenolphthalein indicator that 2 drop mass fractions are 5% is added, the NaOH standard liquids for being 0.1mol/L with concentration are titrated to pale red
Color (will not fade) in 30 seconds.Add the NaOH standard liquids that 2.5mL concentration is 0.5mol/L into conical flask with pipette again,
Shake up, seal, shake saponification 4 hours at room temperature.The hydrochloric acid standard solution for being afterwards 0.5mol/L with concentration be titrated to it is colourless,
As titration end-point.The volume for the hydrochloric acid standard solution that record titration uses is V1.Under the same conditions, entered with bagasse xylan
Line blank titrates, the consumed HCl standard liquid volumes V of record0.Galloyl substitution value (DSC) calculating formula it is as follows：
In formula：
The mass fraction of the galloyl of w-bagasse xylan gallate, %；
V0- titration bagasse xylan consumption hydrochloric acid standard solution volume, Unit/mL；
V1The hydrochloric acid standard solution volume of-titration bagasse xylan gallate consumption, Unit/mL；
CHCl- hydrochloric acid standard solution concentration, unit mol/L；
The quality of m-bagasse xylan gallate sample, unit g；
M and 132-galloyl and bagasse xylan dehydration xylose units relative molecular mass.
(21) using the asafoetide acyl of bagasse xylan gallic acid/ferulic acid ester obtained by determination of acid-basetitration step (19)
Base substitution value.Specific method and step are as follows：Accurately weigh 0.5g samples to be placed in 50mL conical flasks, add 10mL distilled water,
Shake up, add the phenolphthalein indicator that 2 drop mass fractions are 5%, the NaOH standard liquids for being 0.1mol/L with concentration are titrated to shallow
Red (will not be faded in 30 seconds).It is molten to add the NaOH standards that 2.5mL concentration is 0.5mol/L into conical flask with pipette again
Liquid, shake up, seal.Saponification 4 hours is shaken at room temperature.The hydrochloric acid standard solution for being afterwards 0.5mol/L with concentration is titrated to nothing
Color, as titration end-point, the volume for the hydrochloric acid standard solution that record titration uses is V2.Under the same conditions, it is poly- with bagasse wood
Sugared gallate carries out blank titration, the consumed HCl standard liquid volumes V of record1.Asafoetide acyl substitution (DSC) meter
Formula is as follows：
In formula：
The mass fraction of the asafoetide acyl group of w-bagasse xylan gallic acid/ferulic acid ester, %；
V1- titration bagasse xylan gallate consumption hydrochloric acid standard solution volume, Unit/mL；
V2The hydrochloric acid standard solution volume of-titration bagasse xylan gallic acid/ferulic acid ester consumption, Unit/mL；
CHCl- hydrochloric acid standard solution concentration, unit mol/L；
The quality of m-bagasse xylan gallic acid/ferulic acid ester sample, unit g；
The relative molecular mass of M and 285-asafoetide acyl group and bagasse xylan gallate dewatering unit.
Brief description of the drawings
Fig. 1 schemes for former bagasse xylan IR.
Fig. 2 is bagasse xylan gallic acid/ferulic acid ester IR figures.
Fig. 3 schemes for former bagasse xylan SEM.
Fig. 4 is bagasse xylan gallic acid/ferulic acid ester SEM figures.
Fig. 5 schemes for former bagasse xylan TG-DTG.
Fig. 6 is bagasse xylan gallic acid/ferulic acid ester TG-DTG figures.
Embodiment
Embodiment：
(1) 6g bagasse xylans are dried to 24 hours in 60 DEG C of vacuum constant temperature drying boxes to constant weight, obtain butt bagasse wood
Glycan.
(2) 20g gallic acids are added in 250mL four-hole boiling flask, and add thereto 22mL analyze pure acetic anhydride and
15mL analyzes pure pyridine, and it is 5 DEG C to control ice bath temperature, stirs lower reaction 8 hours.
(3) reaction solution obtained by step (2) is transferred in 100mL beakers, it is 20% to stir the lower 35mL mass fractions that add
Hydrochloric acid solution, separate out white precipitate in beaker.Sent after white precipitate after filtering is precipitated 3 times with 15mL distillation water washings
24 hours are dried into 50 DEG C of vacuum constant temperature drying box to constant weight, obtains triacetyl gallic acid.
(4) take triacetyl gallic acid obtained by 8g steps (3) to be added in 250mL four-hole boiling flask, add thereto
40mL analyzes pure hexamethylene and 0.35g analysis absolute dimethylformamide, is stirred at reflux 30 minutes, and controlling reaction temperature is 75 DEG C,
30mL is added dropwise under agitation and analyzes pure thionyl chloride, controls and was added dropwise in 20 minutes, continue to stir after being added dropwise
Reaction 4 hours.
(5) step (4) resulting material is poured into beaker, is concentrated by evaporation 45 minutes, obtains under conditions of being 75 DEG C in temperature
Light tan solid, the solid is placed in 50 DEG C of vacuum constant temperature drying box and dries 24 hours to constant weight, obtain triacetyl nutgall
Acyl chlorides.
(6) butt bagasse xylan obtained by weighing 5g steps (1) is added in 250mL four-hole boiling flasks, and adds 0.15g pairs
Toluenesulfonic acid and 45mL analysis pure acetones, are stirred at reflux 30 minutes to obtain bagasse xylan suspension.
(7) triacetyl nutgall acyl chlorides obtained by weighing 4g steps (5) is added in reaction system obtained by step (6), stirring
Under be warming up to 50 DEG C, continue reaction 6 hours.
(8) step (7) resulting material is filtered, and analyzes pure absolute ethyl alcohol with 15mL distilled water and 10mL successively respectively and washs
Precipitation 3 times, obtains bagasse xylan triacetyl gallate.
(9) bagasse xylan triacetyl gallate obtained by step (8) is inserted to the absolute ethyl alcohol of 50mL sodium acid carbonates
15 minutes pH to solution are stirred in saturated solution, under normal temperature no longer to change.
(10) filter step (9) resulting material, and distilled with 15mL 50 DEG C true is sent into after water washing filter cake 3 times respectively
24 hours are dried in empty thermostatic drying chamber to constant weight, obtains bagasse xylan gallate.
(11) 10g forulic acids are added in 250mL four-hole boiling flask, and is separately added into 20mL thereto and analyzes pure acetic anhydride
Pure pyridine is analyzed with 13mL, it is 5 DEG C to control frozen water bath temperature, stirs lower reaction 6 hours.
(12) reaction solution obtained by step (2) is transferred in 100mL beakers, it is 25% to stir the lower 35mL mass fractions that add
Hydrochloric acid solution, separate out white precipitate.50 DEG C of vacuum is delivered to after white precipitate is precipitated 3 times with 15mL distillation water washings respectively
24 hours are dried in thermostatic drying chamber to constant weight, obtains Acetyl-ferulic acid.
(13) take Acetyl-ferulic acid obtained by 10g steps (12) to be added in 250mL four-hole boiling flask, and add thereto
35mL analyzes pure hexamethylene and 0.25g analysis absolute dimethylformamide, is stirred at reflux 30 minutes, is stirring under conditions of 60 DEG C
In 30mL be added dropwise analyze pure thionyl chloride, control and be added dropwise in 20 minutes, it is small to continue stirring reaction 3 after being added dropwise
When.
(14) step (13) resulting material is poured into 100mL beakers, 45 is concentrated by evaporation under conditions of being 75 DEG C in temperature
Minute, light tan solid is obtained, the solid is placed in 50 DEG C of vacuum constant temperature drying box and dries 24 hours to constant weight, obtain acetyl
Asafoetide acyl chlorides.
(15) bagasse xylan gallate obtained by weighing 5g steps (10) is added in 250mL four-hole boiling flasks, and to
0.15g p-methyl benzenesulfonic acid is wherein added, 40mL analyzes pure DMF (DMA), stirs and is configured to bagasse wood
Chitosan gallate suspension.
(16) 5g Acetylferuloyl Chlorides are weighed to be added in the reaction system of step (15), are stirred, are warming up to 50 DEG C,
Reaction 4 hours.
(17) step (16) resulting material is filtered, and analyzes pure absolute ethyl alcohol with 15mL distilled water and 10mL successively respectively and washes
Wash filter cake 3 times, obtain bagasse xylan gallic acid/Acetyl-ferulic acid ester.
(18) bagasse xylan gallic acid/Acetyl-ferulic acid ester obtained by step (17) is inserted to the nothing of 50mL sodium acid carbonates
15 minutes pH to solution are stirred in water-ethanol saturated solution, under normal temperature not change.
(19) step (18) resulting material is filtered, 50 DEG C of vacuum is sent into after being precipitated 3 times with 15mL distillation water washings respectively
24 hours are dried in thermostatic drying chamber to constant weight, produces product bagasse xylan gallic acid/ferulic acid ester.
(20) taking for the ester carbonyl group of bagasse xylan gallate obtained by determination of acid-basetitration step (10) is used
Dai Du is 0.64.
(21) using the ester carbonyl of gained bagasse xylan gallic acid/ferulic acid ester in determination of acid-basetitration step (19)
The substitution value of base is 0.71.
Analyzed through IR, in 3408.71cm-1The wide and strong peak formed for hydroxyl stretching vibration with hydrogen bond in glycan molecule,
3011.91cm-1For the C-H stretching vibration peaks of alkene in asafoetide acid molecule, 1689.89cm-1For C=C stretching vibration peaks,
856.27cm-1For C-H flexural vibrations peaks；1507.64cm-1For phenyl ring skeletal vibration characteristic peak, 1121.41cm-1For stretching for C-O
Contracting vibration peak, 1762.21cm-1Vibration peak, 895~870cm are absorbed for esters C=O-1Locate as the xylan of β-D glycosidic bond configurations
Molecular skeleton vibration peak.As can be seen that product of the xylan through over-churning is in 1762.1cm-1、1689.89cm-1、1507.64cm-1There is the infrared signature absorption peak of ester group, double bond, phenyl ring in place respectively, and correspondingly strengthens, and illustrates bagasse xylan gallic acid
There occurs esterification with forulic acid for ester.Product is analyzed through TG-DTG, shows bagasse xylan gallate at 0~100 DEG C
Mass loss close to 15%, and the mass loss of bagasse xylan gallic acid/ferulic acid ester is only 6%；Bagasse xylan
Gallate decomposed at 200~250 DEG C it is rapid, but decomposed at 250~400 DEG C it is slow, and bagasse xylan gallic acid/Ah
Wei's acid esters is divided into two stages in 200~400 DEG C of decomposition, 200~300 DEG C decompose it is rapid after slightly pause, 300~
400 DEG C are continued fast decoupled with other speed, illustrate that the introducing of ferulic changes the rhermal decomposition rate of bagasse xylan.
Product bagasse xylan gallic acid/asafoetide can be seen that in the decomposition rate of 0~100 DEG C and 200~400 DEG C according to product
The heat endurance of acid esters increases.
Claims (1)
- A kind of 1. preparation method of antitumor activity bagasse xylan gallic acid/ferulic acid ester, it is characterised in that specific steps For：（1）5 ~ 10g bagasse xylans are dried 24 hours to constant weight in 60 DEG C of vacuum constant temperature drying boxes, it is poly- to obtain butt bagasse wood Sugar；（2）15 ~ 25g gallic acids are added in 250mL four-hole boiling flask, and add 13 ~ 22mL thereto and analyze pure acetic anhydride Pure pyridine is analyzed with 11 ~ 16mL, it is 5 ~ 25 DEG C to control ice bath temperature, stirs lower reaction 6 ~ 12 hours；（3）By step（2）Gained reaction solution is transferred in 100mL beakers, stir it is lower add 20 ~ 40mL mass fractions be 20% ~ 30% hydrochloric acid solution, white precipitate is separated out in beaker；White precipitate after filtering 10 ~ 15mL distillation water washings are precipitated 3 times Deliver to afterwards in 50 DEG C of vacuum constant temperature drying box and dry 24 hours to constant weight, obtain triacetyl gallic acid；（4）Take 5 ~ 10g steps（3）Gained triacetyl gallic acid is added in 250mL four-hole boiling flask, thereto add 30 ~ 50mL analyzes pure hexamethylene and 0.1 ~ 0.5g analysis absolute dimethylformamides, is stirred at reflux 30 minutes, and controlling reaction temperature is 60 ~ 80 DEG C, 15 ~ 45mL is added dropwise under agitation and analyzes pure thionyl chloride, controls and was added dropwise in 20 ~ 30 minutes, is added dropwise Continue stirring reaction afterwards 2 ~ 4 hours；（5）By step（4）Resulting material is poured into beaker, is concentrated by evaporation 40 ~ 60 minutes under conditions of being 60 ~ 80 DEG C in temperature, Light tan solid is obtained, the solid is placed in 50 DEG C of vacuum constant temperature drying box and dries 24 hours to constant weight, obtained triacetyl and do not eat Sub- acyl chlorides；（6）Weigh 3 ~ 8g steps（1）Gained butt bagasse xylan is added in 250mL four-hole boiling flasks, and adds 0.1 ~ 0.3g P-methyl benzenesulfonic acid and 30 ~ 50mL analysis pure acetones, are stirred at reflux 30 minutes to obtain bagasse xylan suspension；（7）Weigh 2 ~ 4g steps（5）Gained triacetyl nutgall acyl chlorides is added to step（6）In gained reaction system, under stirring 30 ~ 55 DEG C are warming up to, continues reaction 3 ~ 6 hours；（8）Filter step（7）Resulting material, and analyze pure absolute ethyl alcohol with 10 ~ 15mL distilled water and 5 ~ 10mL successively respectively and wash Wash precipitation 2 ~ 3 times, obtain bagasse xylan triacetyl gallate；（9）By step（8）The absolute ethyl alcohol that gained bagasse xylan triacetyl gallate inserts 30 ~ 50mL sodium acid carbonates is satisfied 10 ~ 30 minutes pH to solution are stirred in solution, under normal temperature no longer to change；（10）Filter step（9）Resulting material, and distilled with 10 ~ 15mL 50 DEG C of vacuum is sent into after water washing filter cake 3 times respectively 24 hours are dried in thermostatic drying chamber to constant weight, obtains bagasse xylan gallate；（11）4 ~ 10g forulic acids are added in 250mL four-hole boiling flask, and be separately added into 13 ~ 22mL thereto and analyze pure acetic acid Acid anhydride and 11 ~ 16mL analysis pure pyridines, it is 5 ~ 25 DEG C to control frozen water bath temperature, stirs lower reaction 6 ~ 12 hours；（12）By step（2）Gained reaction solution is transferred in 100mL beakers, stir it is lower add 20 ~ 40mL mass fractions be 20% ~ 30% hydrochloric acid solution, separate out white precipitate；50 DEG C are delivered to after white precipitate is precipitated 3 times with 10 ~ 15mL distillation water washings respectively Vacuum constant temperature drying box in dry 24 hours to constant weight, obtain Acetyl-ferulic acid；（13）Take 5 ~ 10g steps（12）Gained Acetyl-ferulic acid is added in 250mL four-hole boiling flask, and thereto add 30 ~ 50mL analyzes pure hexamethylene and 0.1 ~ 0.3g analysis absolute dimethylformamide, is stirred at reflux under conditions of 60 ~ 80 DEG C 30 minutes, 20 ~ 40mL is added dropwise in stirring and analyzes pure thionyl chloride, controls and was added dropwise in 20 ~ 30 minutes, is added dropwise follow-up Continuous stirring reaction 2 ~ 4 hours；（14）By step（13）Resulting material is poured into 100mL beakers, temperature be 60 ~ 80 DEG C under conditions of be concentrated by evaporation 30 ~ 50 minutes, light tan solid is obtained, the solid is placed in 50 DEG C of vacuum constant temperature drying box and dries 24 hours to constant weight, obtain acetyl Asafoetide acyl chlorides；（15）Weigh 4 ~ 8g steps（10）Gained bagasse xylan gallate is added in 250mL four-hole boiling flasks, and to its Middle addition 0.1 ~ 0.3g p-methyl benzenesulfonic acid, 30 ~ 50mL analyze pure N, N-Dimethylformamide, stirring, it is poly- to be configured to bagasse wood Sugared gallate suspension；（16）Weigh 2 ~ 5g Acetylferuloyl Chlorides and be added to step（15）Reaction system in, stir, be warming up to 40 ~ 60 DEG C, react 3 ~ 6 hours；（17）Filter step（16）Resulting material, and analyze pure absolute ethyl alcohol with 10 ~ 15mL distilled water and 5 ~ 10mL successively respectively Wash filter cake 2 ~ 3 times, obtain bagasse xylan gallic acid/Acetyl-ferulic acid ester；（18）By step（17）Gained bagasse xylan gallic acid/Acetyl-ferulic acid ester inserts the nothing of 30 ~ 50mL sodium acid carbonates 10 ~ 20 minutes pH to solution are stirred in water-ethanol saturated solution, under normal temperature not change；（19）Filter step（18）Resulting material, it is permanent that 50 DEG C of vacuum is sent into after being precipitated 3 times with 10 ~ 15mL distillation water washings respectively 24 hours are dried in warm drying box to constant weight, produces bagasse xylan gallic acid/ferulic acid ester.
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| CN109320632A (en) * | 2018-10-21 | 2019-02-12 | 桂林理工大学 | A kind of synthetic method of bagasse xylan gallic acid trimesic acid double esterification derivative |
| CN109400736A (en) * | 2018-10-21 | 2019-03-01 | 桂林理工大学 | The synthetic method of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether |
| CN109400758A (en) * | 2018-10-21 | 2019-03-01 | 桂林理工大学 | A kind of synthetic method of bagasse xylan gallic acid dioctadecyl terephthalate derivative |
| CN109400735A (en) * | 2018-10-21 | 2019-03-01 | 桂林理工大学 | A kind of double esterification bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester synthetic method |
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| CN104448057A (en) * | 2014-12-17 | 2015-03-25 | 桂林理工大学 | Preparation method of nano-scale ferulic acid bagasse xylan ester |
| 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 |
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| CN109320632A (en) * | 2018-10-21 | 2019-02-12 | 桂林理工大学 | A kind of synthetic method of bagasse xylan gallic acid trimesic acid double esterification derivative |
| CN109400736A (en) * | 2018-10-21 | 2019-03-01 | 桂林理工大学 | The synthetic method of double esterification 3,4,5-trihydroxy benzoic acid base bagasse xylan benzoic ether |
| CN109400758A (en) * | 2018-10-21 | 2019-03-01 | 桂林理工大学 | A kind of synthetic method of bagasse xylan gallic acid dioctadecyl terephthalate derivative |
| CN109400735A (en) * | 2018-10-21 | 2019-03-01 | 桂林理工大学 | A kind of double esterification bagasse xylan-trihydroxybenzoic acid/isophthalic acid ester synthetic method |
| CN110713559A (en) * | 2019-10-22 | 2020-01-21 | 桂林理工大学 | Method for synthesizing active cinnamic acid/p-chlorobenzoic acid bagasse xylan diester |
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