CN107573505A - A kind of poly-D-lysine cinnamic acid compound, preparation method and its usage - Google Patents
A kind of poly-D-lysine cinnamic acid compound, preparation method and its usage Download PDFInfo
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- CN107573505A CN107573505A CN201710651883.6A CN201710651883A CN107573505A CN 107573505 A CN107573505 A CN 107573505A CN 201710651883 A CN201710651883 A CN 201710651883A CN 107573505 A CN107573505 A CN 107573505A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The present invention relates to a kind of poly-D-lysine cinnamic acid amides compound, preparation method and its usage.Preparation method is using curdlan as raw material, including following steps：(1) cinnamic acid is dissolved in weakly alkaline solution (pH=7~8), treats that cinnamic acid all dissolves, added 1 ethyl (3 dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate and stir 10~60min or so.(2) by the solution obtained by poly-D-lysine addition step 1,4 DEG C of 2~4h of reaction, 5~24h is then reacted at 20~25 DEG C.(3) pH value of solution that step (2) obtains is transferred to 5~8 with 1~3mol/L hydrochloric acid, then extracted in ethanol, obtained sediment is freeze-dried, and obtains poly-D-lysine cinnamic acid.The poly-D-lysine cinnamic acid that the present invention obtains, substitution value are 20 100%.The poly-D-lysine cinnamic acid good water solubility that the present invention obtains, there is broad-spectrum antibacterial and bactericidal property, there is bacteriostasis to colibacillus, staphylococcus, staphylococcus aureus, mould, there is good moisturizing permeance property.
Description
Technical field
The invention belongs to antiseptic and antibiotic agent field, and in particular to a kind of poly-D-lysine-cinnamic acid amides compound
Preparation method and its usage.
Background technology
As living standards of the people improve, the concept of health and green is increasingly by big well-established.Exploitation is efficient, peace
Entirely, wide spectrum, the natural anticorrosion antiseptic of stable performance are more and more interested to researchers.To the market of natural anticorrosion antiseptic
Demand is also inevitable growing.
Cinnamic acid is a kind of natural equivalent corrosion-resistanting perfume, to the bacterium that various food become sour can be caused to have the propagation of wide spectrum
Inhibition；It can effectively press down and kill saccharomycete, bacterium, mould, aflatoxin, Escherichia coli, gram-negative, positive bacillus；Especially
It is most strong to often causing the saccharomycete of food spoilage, mould to act on, and the distinctive flavor of cinnamic acid plays increasing to antistaling agent
The effect of fresh flavouring, after this product is edible, easily it is absorbed by the body, while catabolism is the material nontoxic to human body.
Epsilon-polylysine is but bad to the fungistatic effect of fungi as food antiseptic bacteriostatic agent.Chemical modification can be passed through
Introduce broad-spectrum antibacterial and antibacterial activity that cinnamate group improves epsilon-polylysine.Simultaneously because the introducing of cinnamate group, drop
The low cationic of poly-D-lysine, so as to reduce stimulation performance of the poly-D-lysine to skin.
The content of the invention
It is an object of the invention to provide a kind of poly-D-lysine-cinnamic acid compound and preparation method thereof, the party
Poly-D-lysine-cinnamic acid prepared by method is that the hydrogen partial on the amino of poly-D-lysine substitutes generation by cinnamic acid
Poly-D-lysine-cinnamic acid, its substitution value are 20~100%.Poly-D-lysine prepared by the present invention-cinnamic acid tool
There is the antibacterial and bactericidal property of wide spectrum, the preparation method reaction time of the invention is short, efficiency high, easy control of reaction conditions, behaviour
Make simply, agents useful for same is all green non-pollution, thus is with a wide range of applications.Poly-D-lysine concentration of aqueous solution poly
Lysine reduces positive charge due to introducing cinnamate group, reduces the excitant of poly-D-lysine, can be used as antibacterial
NMF is applied to household chemicals field.
Poly-D-lysine-cinnamic acid that the present invention obtains, has the advantage that：
1. reactant is food additives, agents useful for same is all green non-pollution, and poly-D-lysine-cinnamic acid belongs to edible
With the green product of property；
2. poly-D-lysine-cinnamic acid has the restraining and sterilizing bacteria performance of wide spectrum；
Poly-D-lysine-cinnamic acid made from 3., good water solubility, there is good performance of keeping humidity and permeance property, have
Good biodegradability, thus can apply in filed of daily-use chemical industry.
The present invention concrete technology step be：
Step 1：Take a certain amount of cinnamic acid to be dissolved in weakly alkaline solution (pH=7~8), treat that cinnamic acid all dissolves, add
Enter 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate and stir 10~60min or so.
Step 2：By in the solution obtained by a certain amount of poly-D-lysine addition step 1, -4 DEG C are reacted 2~4h, then
5~24h is reacted at 20~25 DEG C.
Step 3：The pH value of solution that step (2) obtains is transferred to 5~8 with 1~3mol/L hydrochloric acid, then carried in ethanol
Take, obtain
Figure of description
Fig. 1 is the infrared spectrogram of poly-D-lysine-cinnamic acid of the present invention.
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of poly-D-lysine-cinnamic acid of the present invention.
Fig. 3 is the antibacterial figure of poly-D-lysine-cinnamic acid of the present invention, and Fig. 3 (a) is Escherichia coli, and Fig. 3 (b) is
Staphylococcus.
Embodiment
Embodiment 1：(1) 1moL cinnamic acids are taken to be dissolved in 30mL NaHCO3In (0.3mol/L) solution, cinnamic acid whole is treated
Dissolving, add 2moL 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate and stir 20min or so；(2) will
In solution obtained by 1moL poly-D-lysine addition step 1, -4 DEG C of reaction 2h, then 24h is reacted at 25 DEG C；(3) use
The pH value of solution that step (2) obtains is transferred to 7 by 1mol/L hydrochloric acid, is then extracted in ethanol, and obtained sediment is freezed
Dry, obtain poly-D-lysine-cinnamic acid.
As can be seen from Figure 1 in 3261cm in figure-1For NH2, by 3062cm-1And 1529cm-1The presence of phenyl ring is may determine that,
1635cm-1For C=C and C=O overlap peak, illustrate successfully to synthesize poly-D-lysine-cinnamic acid.
As can be seen from Figure 2, δ is 3.77 proton peaks for belonging to H-1 in figure, and δ is 1.61 proton peaks for belonging to H-2, δ 1.26
Belong to H-3 proton peak, δ is 1.43 proton peaks for belonging to H-4, and δ is 3.11 proton peaks for belonging to H-5.δ is on 7.30 phenyl ring
H-9 corresponding to carbon；δ is 7.46, δ is 6.53 respectively H-6 and H-7 corresponding to double key carbon.
Integral area calculates substitution value from Fig. 2
Integral area calculate substitution value DS=[(H-6+H-7)/2/ (H-1)] × 100%=[(0.52+0.58)/2/1] ×
100%=55%.
Embodiment 2：(1) 1moL cinnamic acids are taken to be dissolved in 30mL NaHCO3In (0.3mol/L) solution, cinnamic acid whole is treated
Dissolving, add 0.5moL 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate and stir 20min or so；(2)
By in the solution obtained by 1moL poly-D-lysine addition step 1,0 DEG C of reaction 2h, then 24h is reacted at 25 DEG C；(3) use
The pH value of solution that step (2) obtains is transferred to 7 by 1mol/L hydrochloric acid, is then extracted in ethanol, and obtained sediment is freezed
Dry, obtain poly-D-lysine-cinnamic acid.
Embodiment 3：(1) take 1moL cinnamic acids to be dissolved in 20mL NaOH (0.3mol/L) solution, treat that cinnamic acid is all molten
Solution, add 0.5moL 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate and stir 20min or so；(2) will
In solution obtained by 1moL poly-D-lysine addition step 1,0 DEG C of reaction 2h, then 24h is reacted at 25 DEG C；(3) use
The pH value of solution that step (2) obtains is transferred to 7 by 1mol/L hydrochloric acid, is then extracted in ethanol, and obtained sediment is freezed
Dry, obtain poly-D-lysine-cinnamic acid.
Embodiment 4：(1) 0.5moL cinnamic acids are taken to be dissolved in 25mL NaHCO3In (0.3mol/L) solution, treat that cinnamic acid is complete
Portion dissolves, and adds 1moL 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate and stirs 20min or so；(2)
By in the solution obtained by 1moL poly-D-lysine addition step 1,0 DEG C of reaction 2h, then 24h is reacted at 25 DEG C；(3) use
The pH value of solution that step (2) obtains is transferred to 7 by 1mol/L hydrochloric acid, is then extracted in ethanol, and obtained sediment is freezed
Dry, obtain poly-D-lysine-cinnamic acid.
Embodiment 5：(1) 1moL cinnamic acids are taken to be dissolved in 18mL NaHCO3In (0.3mol/L) solution, cinnamic acid whole is treated
Dissolving, add 1.5moL 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate and stir 20min or so；(2)
By in the solution obtained by 1moL poly-D-lysine addition step 1, -3 DEG C of reaction 2h, then 20h is reacted at 25 DEG C；(3)
The pH value of solution that step (2) obtains is transferred to 7 with 1mol/L hydrochloric acid, then extracted in ethanol, obtained sediment carries out cold
It is lyophilized dry, obtain poly-D-lysine-cinnamic acid.
Embodiment 6：(1) take 1moL cinnamic acids to be dissolved in 20mL NaOH (0.3mol/L) solution, treat that cinnamic acid is all molten
Solution, add 1.5moL 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate and stir 20min or so；(2) will
In solution obtained by 1moL poly-D-lysine addition step 1, -2 DEG C of reaction 1h, then 20h is reacted at 23 DEG C；(3) use
The pH value of solution that step (2) obtains is transferred to 7 by 1mol/L hydrochloric acid, is then extracted in ethanol, and obtained sediment is freezed
Dry, obtain poly-D-lysine-cinnamic acid.
Embodiment 7：
Application Example
Poly-D-lysine-cinnamic acid that selection example 1 obtains, Antibacterial Activity is carried out to it：Using agar
Flat band method carries out qualitative antibacterial detection to poly-D-lysine-cinnamic acid, first by 100 microlitres of bacterial suspension even spreads
On agar plate, using Escherichia coli and staphylococcus to represent bacterium.The circular filter paper piece of the size such as sterilized is soaked
5min soaks filter paper in the aqueous solution of 10mL 1mg/mL poly-D-lysines-cinnamic acid, using deionized water as pair
According to, then with sterilizing tweezers filter paper is put on the agar plate for coating bacteria suspension, at 37 DEG C cultivate 24h after observe suppression
Bacterium circle, as shown in figure 3, finding out from Fig. 3 (a), poly-D-lysine-cinnamic acid has obvious bacteriostasis to Escherichia coli,
Find out from Fig. 3 (b), poly-D-lysine-cinnamic acid has obvious bacteriostasis to staphylococcus.
The foregoing is only a specific embodiment of the invention, but protection scope of the present invention is not limited thereto, any
Belong to those skilled in the art the invention discloses technical scope in, the change or replacement that can be readily available, all should
It is included within the scope of the present invention.Therefore, protection scope of the present invention should using scope of the claims as
It is accurate.
Claims (3)
1. a kind of preparation method of poly-D-lysine-cinnamic acid, it is characterised in that including following preparation process：
(1) cinnamic acid is dissolved in weakly alkaline solution (pH=7~8), treats that cinnamic acid all dissolves, add 1- ethyls-(3- diformazans
Base aminopropyl) phosphinylidyne diimmonium salt hydrochlorate (EDC) and 10~60min of stirring or so；
(2) by the solution obtained by poly-D-lysine (ε-PL) addition step (1), (- 4~0) DEG C reacts 2~4h, Ran Hou
5~24h is reacted at 20~25 DEG C.
Wherein, the alkali in step (1) in weakly alkaline solution, can be NaHCO3Or one kind in NaOH；Cinnamic acid in step (1)
Mol ratio with EDC is 1：(0.5~2)；The mol ratio of ε-PL and the cinnamic acid of (1) in step (2) are (0.5~2)：1：
(3) pH value of solution that step (2) obtains is transferred to 5~8 with 1~3mol/L hydrochloric acid, then extracts, obtain in ethanol
Sediment is freeze-dried, and obtains poly-D-lysine-cinnamic acid.
A kind of 2. preparation method of poly-D-lysine-cinnamic acid according to claim 1, it is characterised in that：The party
Poly-D-lysine-cinnamic acid that method is prepared, its molecular structural formula are：
Wherein, R substitution value is 20~100%.
A kind of 3. application of poly-D-lysine-cinnamic acid as described in claim 1, it is characterised in that the polylysine-
Cinnamic acid has bacteriostasis property, has bacteriostasis to colibacillus, staphylococcus, staphylococcus aureus, mould, tool
There are good performance of keeping humidity and permeance property, can apply in pharmacy, food, daily chemical product.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007230871A (en) * | 2006-02-27 | 2007-09-13 | Osaka Univ | Stimuli-responsive material |
| CN103298495A (en) * | 2010-05-27 | 2013-09-11 | 南洋理工大学 | Polymerizable composition for ophthalmic and medical use and antibacterial composition obtained by polymerizing same |
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- 2017-08-02 CN CN201710651883.6A patent/CN107573505A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007230871A (en) * | 2006-02-27 | 2007-09-13 | Osaka Univ | Stimuli-responsive material |
| CN103298495A (en) * | 2010-05-27 | 2013-09-11 | 南洋理工大学 | Polymerizable composition for ophthalmic and medical use and antibacterial composition obtained by polymerizing same |
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