CN109400768A - A kind of synthetic method of bioactivity bagasse xylan -4- acetylamino cinnamate-g-AM/MMA - Google Patents
A kind of synthetic method of bioactivity bagasse xylan -4- acetylamino cinnamate-g-AM/MMA Download PDFInfo
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- CN109400768A CN109400768A CN201811225994.1A CN201811225994A CN109400768A CN 109400768 A CN109400768 A CN 109400768A CN 201811225994 A CN201811225994 A CN 201811225994A CN 109400768 A CN109400768 A CN 109400768A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F251/00—Macromolecular compounds obtained by polymerising monomers on to polysaccharides or derivatives thereof
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Abstract
The invention discloses the synthetic methods of bioactivity bagasse xylan 4- acetylamino cinnamate-g-AM/MMA a kind of.Using bagasse xylan as primary raw material, using acrylamide and methyl methacrylate as mixed grafting monomer,N,N’Methylene-bisacrylamide is crosslinking agent, and potassium peroxydisulfate and sodium hydrogensulfite are initiation system, synthesizing cross-linked type graft product bagasse xylan-g-AM/MMA；Again using 4- acetyl group cinnamic acid as esterifying agent,N,NDicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine are composite catalyst, have synthesized cross-linking type bagasse xylan -4- acetyl group cinnamate-g-AM/MMA through catalytic esterification in dichloromethane solvent.The present invention enhances the bioactivity of bagasse xylan, is with a wide range of applications in fields such as medicine, food, fine chemistry industries to the grafting of bagasse xylan, crosslinking, esterification three kinds of activity against organisms groups of composite modified introducing.
Description
Technical field
The present invention relates to technical field of polymer materials, especially a kind of bioactivity bagasse xylan -4- acetylamino
The synthetic method of cinnamate-g-AM/MMA.
Background technique
Due to the development of molecular biology, it is highly important that people gradually recognize that polysaccharide and its complex molecule have
The adjusting of biological function, polysaccharide and immune function, the transport of intercellular substance, Clinics and Practices of cancer etc. suffer from close
Relationship.Xylan wide spectrum biological activity is gradually recognized by people, is such as adjusted immunity of organism, is inhibited tumour, anti-aging, resists
The natural sex in the bioactivity such as bacterium is antiviral, unique activity and source has biggish answer in ensureing human health application
Use potentiality.But xylan bioactivity itself is lower, so it is generally necessary to the chemical modifications such as be esterified, be grafted to xylan,
To improve the bioactivity of xylan.
Weak to the intracorporal water environment specific aim of people because bagasse xylan solubility is lower, anticancer activity is difficult to give full play to.
Bagasse xylan can be improved by being grafted the monomers such as acrylamide (AM), methyl methacrylate (MMA) containing vinyl group
Solubility, stability and the bioavilability of molecule, enable bagasse xylan preferably to act on human body.In addition, in bagasse
On xylan pendant hydroxyl group introduce 4- acetylamino cinnamate group can by reduce mitogen-activated protein kinase (MAPK),
The effects of inhibiting nitricoxide synthase and removing free radical, influences apoptosis, invasion, transfer of tumour cell etc., to improve sugarcane
Anti-oxidant, the anti-tumor activity of slag xylan.
The present invention is using bagasse xylan as primary raw material, using acrylamide and methyl methacrylate as mixed grafting list
Body, N, N '-methylene-bisacrylamide are crosslinking agent, and potassium peroxydisulfate and sodium hydrogensulfite are initiation system, and synthesizing cross-linked type connects
Branch product bagasse xylan-g-AM/MMA；Again using 4- acetyl group cinnamic acid as esterifying agent, N, N- dicyclohexylcarbodiimide
(DCC) it is composite catalyst with 4-dimethylaminopyridine, has synthesized cross-linking type bagasse through catalytic esterification in dichloromethane solvent
Xylan -4- acetyl group cinnamate-g-AM/MMA.
Summary of the invention
The purpose of the present invention is the bioactivity such as anti-oxidant, antitumor of enhancing bagasse xylan, provide a kind of bagasse
The synthetic method of xylan -4- acetylamino cinnamate-g-AM/BA.
Specific steps of the invention are as follows:
(1) 5~10g bagasse xylan is placed in 60 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains butt
Bagasse xylan.
(2) it weighs butt bagasse xylan obtained by 3~6g step (1) and 250mL four-hole boiling flask is added, and 12 are added thereto
~20mL deionized water stirs 25~30 minutes at 40~50 DEG C.
(3) 0.2~0.5g potassium peroxydisulfate and 0.5g~0.8g sodium hydrogensulfite are successively weighed in 50mL beaker, and is added
15~20mL deionized water stirs evenly to obtain initiator mixed solution at 20~25 DEG C, spare.
(4) acrylamide (AM) of 1~2g and the pure methyl methacrylate of analysis (MMA) of 2~4g are weighed in 100mL
In flask, and 10~20mL deionized water, 0.1~0.3g N, N '-methylene-bisacrylamide and 1~1.5g technical grade is added
OP-10 is dispersed with stirring 1~1.5 hour to obtain mixed monomer solution using high-shear emulsion machine, pours into 100mL constant pressure funnel
In, it is spare.
(5) mixed monomer solution that a dropping step (4) is prepared into system obtained by step (2), adjusting temperature is 60~70
DEG C, control was added dropwise at 2~4 hours；After adding to the 1/2 of mixed monomer solution, 0.1~0.2g N, N '-methylene is added
Bisacrylamide.Meanwhile initiator solution obtained by step (3) is added portionwise, every 5~10 minutes 0.2~0.8mL of dropwise addition, drop
Add finish after the reaction was continued 3~5 hours.To which after reaction, material is cooled to room temperature.
(6) 30~40mL is added to step (5) resulting material to analyze pure acetone precipitating 30~40 minutes, filters and with 15
The washing of~20mL dehydrated alcohol filters 3 times, and filter cake is put into surface plate, and it is small to be placed in 50 DEG C of vacuum constant temperature drying boxes dry 24
Up to constant weight, intermediate product bagasse xylan-g-AM/MMA is obtained.
(7) bagasse xylan-g-AM/MMA obtained by 1~2g step (6) is successively weighed to be added in 250mL four-hole boiling flask,
Then 0.4~0.8g 4- acetylamino cinnamic acid, 0.5~2g N, N- dicyclohexylcarbodiimide (DCC), 0.1 are sequentially added
~0.4g 4-dimethylaminopyridine and 30~50mL analyze absolute dichloromethane, control reaction temperature at 60~80 DEG C, are stirred to react
6~9 hours.To which after reaction, material is cooled to room temperature.
(8) step (7) resulting material is filtered, and successively analyzes pure C with 10~15mL dehydrated alcohol and 5~10mL respectively
Ketone is respectively washed, is filtered 2~3 times.Filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to perseverance
Weight is to get product bagasse xylan -4- acetylamino cinnamate-g-AM/MMA.
(9) the carboxylic esterification degree of substitution of the bagasse xylan derivative obtained by determination of acid-basetitration step (8), operation side
Method is as follows: the Product samples of accurate weighing 0.50g are put into 250mL conical flask, and 5mL deionized water is added, and then instill three drops
Phenolphthalein indicator.The standard solution of the sodium hydroxide of 2.5mL 0.5mol/L is added, shakes up.Concussion saponification 1 hour at 25 DEG C.
The inner wall of plug, conical flask is rinsed with the deionized water of 10mL, then be titrated to 0.5mol/L hydrochloric acid standard solution it is colourless, as
Terminal.It records HCl and consumes volume V1.Under the same conditions, blank titration, record consumption are carried out with the bagasse xylan before esterification
HCl standard solution volume V0.Carboxylic esterification degree of substitution (DSC) calculation formula is as follows:
In formula:
W --- contain the mass fraction of ester carbonyl group, unit % in product；
V0--- titration bagasse xylan graft copolymerization derivative consumes hydrochloric acid standard solution volume, Unit/mL；
V1--- the hydrochloric acid standard solution volume of titration product consumption, Unit/mL；
CHCl--- hydrochloric acid standard solution concentration, unit moL/L；
The quality of M --- product, unit g；
The relative molecular mass of acyl group and bagasse xylan the dehydration xylose units of M and 132 --- carboxylate agent.
The present invention by grafting to bagasse xylan, be crosslinked, be esterified three kinds of activity against organisms groups of composite modified introducing,
The bioactivity of bagasse xylan is enhanced, is with a wide range of applications in fields such as medicine, food, fine chemistry industries.
Detailed description of the invention
Fig. 1 is the SEM photograph of former bagasse xylan
Fig. 2 is the SEM photograph of bagasse xylan -4- acetylamino cinnamic acid-g-AM/MMA
Fig. 3 is the IR figure of former bagasse xylan
The IR that Fig. 4 is bagasse xylan -4- acetylamino cinnamic acid-g-AM/MMA schemes
Fig. 5 is the XRD diagram of former bagasse xylan
Fig. 6 is the XRD diagram of bagasse xylan -4- acetylamino cinnamic acid-g-AM/MMA
Fig. 7 is TG the and DTG curve of former bagasse xylan
Fig. 8 is TG the and DTG curve of bagasse xylan -4- acetylamino cinnamic acid-g-AM/MMA
Specific embodiment
Embodiment:
(1) 10g bagasse xylan is placed in 60 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains butt bagasse
Xylan.
(2) it weighs butt bagasse xylan obtained by 6g step (1) and 250mL four-hole boiling flask is added, and 20mL is added thereto
Deionized water stirs 30 minutes at 50 DEG C.
(3) 0.5g potassium peroxydisulfate and 0.8g sodium hydrogensulfite are successively weighed in 50mL beaker, and 20mL deionization is added
Water stirs evenly to obtain initiator mixed solution at 25 DEG C, spare.
(4) acrylamide (AM) of 2g and the pure methyl methacrylate of analysis (MMA) of 4g are weighed in 100mL flask,
And 20mL deionized water, 0.3g N, N '-methylene-bisacrylamide and 1.5g technical grade OP-10 is added, using high shear cream
Change machine is dispersed with stirring 1.5 hours to obtain mixed monomer solution, pours into 100mL constant pressure funnel, spare.
(5) mixed monomer solution that a dropping step (4) is prepared into system obtained by step (2), adjusting temperature is 70 DEG C,
Control was added dropwise at 4 hours；After adding to the 1/2 of mixed monomer solution, 0.2g N, N '-methylene bisacrylamide acyl is added
Amine.Meanwhile initiator solution obtained by step (3) is added portionwise, every 6 minutes dropwises addition 0.5mL, it is added dropwise that the reaction was continued afterwards 5
Hour.To which after reaction, material is cooled to room temperature.
(6) 40mL is added to step (5) resulting material to analyze pure acetone precipitating 40 minutes, filters and with the anhydrous second of 20mL
Alcohol washing filters 3 times, and filter cake is put into surface plate, be placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains
Between product bagasse xylan-g-AM/MMA.
(7) it successively weighs bagasse xylan-g-AM/MMA obtained by 2g step (6) to be added in 250mL four-hole boiling flask, then
Sequentially add 0.8g 4- acetylamino cinnamic acid, 1.8g N, N- dicyclohexylcarbodiimide (DCC), 0.4g 4- dimethylamino
Pyridine and 50mL analyze absolute dichloromethane, control reaction temperature at 80 DEG C, are stirred to react 8 hours.To after reaction, by material
It is cooled to room temperature.
(8) step (7) resulting material is filtered, and successively each with 10~5mL dehydrated alcohol and 10mL analysis pure acetone respectively
Washing filters 3 times.Filter cake is put into surface plate, be placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get
Product bagasse xylan -4- acetylamino cinnamate-g-AM/MMA.
(9) it is carried out using esterification degree of the acid-base titration to bagasse xylan 4- acetylamino cinnamate-g-AM/MMA
Measurement, measuring DS is 0.582.
It is analyzed by the product bagasse xylan 4- acetylamino cinnamate-g-AM/MMA that embodiment synthesizes through IR,
1741.48cm-1There are the carbonyl C=O eigen vibration absorption peak of AM and ester bond, 1691.34cm-1Place is that amide stretching vibration absorbs
Peak, 1670.12cm-1It is carbon-carbon double bond stretching vibration absworption peak, 1592.98cm-1Place is phenyl ring skeleton stretching vibration absworption peak.
For sem analysis the result shows that after reaction, surface is uneven, has sheet packed structures, has obviously empty
Gap and damaged rill, it was demonstrated that sent out change by modified original structure surface.TG the and DTG curve for analyzing product, is arrived at 200 DEG C
250 DEG C of stages, mass loss reach up to 25%, mainly bagasse xylan 4- acetyl cinnamate-g-AM/MMA itself
Decomposition caused by, final product is significantly improved in 800 DEG C of Shi Yuyuan bagasse xylans compared to thermal stability.It can through XRD analysis
Know, product is that peak crystallization increases at 17.98 °, 19.36 °, 22.26 °, 24.84 °, 26.43 ° in 2 θ of powder, and peak type illustrates more by force
Crystalline content is more, and crystal region is complete.
Claims (1)
1. a kind of synthetic method of immunocompetence bagasse xylan 4- acetylamino cinnamate-g-AM/MMA, it is characterised in that
Specific steps are as follows:
(1) 5 ~ 10g bagasse xylan is placed in 60 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight, obtains butt bagasse wood
Glycan；
(2) it weighs butt bagasse xylan obtained by 3 ~ 6g step (1) and 250mL four-hole boiling flask is added, and 12 ~ 20mL is added thereto
Deionized water stirs 25 ~ 30 minutes at 40 ~ 50 DEG C；
(3) 0.2 ~ 0.5g potassium peroxydisulfate and 0.5g ~ 0.8g sodium hydrogensulfite are successively weighed in 50mL beaker, and addition 15 ~
20mL deionized water stirs evenly to obtain initiator mixed solution at 20 ~ 25 DEG C, spare；
(4) the pure methyl methacrylate of analysis of the acrylamide and 2 ~ 4g of 1 ~ 2g is weighed in 100mL flask, and addition 10 ~
20mL deionized water, 0.1 ~ 0.3g N,N’Methylene-bisacrylamide and 1 ~ 1.5g technical grade OP-10, using high-shear emulsifying
Machine is dispersed with stirring 1 ~ 1.5 hour to obtain mixed monomer solution, pours into 100mL constant pressure funnel, spare；
(5) mixed monomer solution that a dropping step (4) is prepared into system obtained by step (2), adjusting temperature is 60 ~ 70 DEG C, control
System was added dropwise at 2 ~ 4 hours；After adding to the 1/2 of mixed monomer solution, 0.1 ~ 0.2g is addedN,N’Methylene bisacrylamide
Amide；Meanwhile initiator solution obtained by step (3) is added portionwise, every 5 ~ 10 minutes 0.2 ~ 0.8mL of dropwise addition, after being added dropwise
The reaction was continued 3 ~ 5 hours；To which after reaction, material is cooled to room temperature；
(6) to step (5) resulting material be added 30 ~ 40mL analyze pure acetone precipitating 30 ~ 40 minutes, filter and with 15 ~ 20mL without
Water-ethanol washing filters 3 times, and filter cake is put into surface plate, is placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight,
Obtain intermediate product bagasse xylan-g-AM/MMA；
(7) bagasse xylan-g-AM/MMA obtained by 1 ~ 2g step (6) is successively weighed to be added in 250mL four-hole boiling flask, then according to
Secondary addition 0.4 ~ 0.8g 4- acetylamino cinnamic acid, 0.5 ~ 2gN,NDicyclohexylcarbodiimide (DCC), 0.1 ~ 0.4g 4-
Dimethylamino naphthyridine and 30 ~ 50mL analyze absolute dichloromethane, control reaction temperature at 60 ~ 80 DEG C, are stirred to react 6 ~ 9 hours；To
After reaction, material is cooled to room temperature；
(8) step (7) resulting material is filtered, and is successively respectively washed with 10 ~ 15mL dehydrated alcohol and 5 ~ 10mL analysis pure acetone respectively
It washs, filter 2 ~ 3 times；Filter cake is put into surface plate, be placed in 50 DEG C of vacuum constant temperature drying boxes dry 24 hours to constant weight to get
Bagasse xylan -4- acetylamino cinnamate-g-AM/MMA.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112175140A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active BX/SGPS quaternary graft copolymerization derivative |
| CN112175142A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of bagasse xylan bromopyruvate-g-AM/MA |
| CN112175141A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM |
| CN112239512A (en) * | 2020-09-06 | 2021-01-19 | 桂林理工大学 | Synthesis method of active bromine-containing bagasse xylan ester-g-AM |
| CN112250797A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Synthesis method of active bagasse xylan bromopyruvate-g-AM/MA/BzA |
| CN112250796A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112175140A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active BX/SGPS quaternary graft copolymerization derivative |
| CN112175142A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of bagasse xylan bromopyruvate-g-AM/MA |
| CN112175141A (en) * | 2020-09-06 | 2021-01-05 | 桂林理工大学 | Synthesis method of active cross-linked BX/SGPS nitro-p-methyl benzoate-g-AM |
| CN112239512A (en) * | 2020-09-06 | 2021-01-19 | 桂林理工大学 | Synthesis method of active bromine-containing bagasse xylan ester-g-AM |
| CN112250797A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Synthesis method of active bagasse xylan bromopyruvate-g-AM/MA/BzA |
| CN112250796A (en) * | 2020-09-06 | 2021-01-22 | 桂林理工大学 | Preparation method of BX/SGPS nitro-p-methyl benzoate-g-AM/MA |
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