CN106279304A - A kind of cinnamylaldehyde derivatives and application thereof - Google Patents

A kind of cinnamylaldehyde derivatives and application thereof Download PDF

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CN106279304A
CN106279304A CN201610706797.6A CN201610706797A CN106279304A CN 106279304 A CN106279304 A CN 106279304A CN 201610706797 A CN201610706797 A CN 201610706797A CN 106279304 A CN106279304 A CN 106279304A
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cinnamic aldehyde
cooh
application
derivant
alkyl
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史鲁秋
苏桂珍
刘文权
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Nanjing Huashi New Material Co Ltd
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Abstract

The present invention relates to a kind of good stability, the exsertile cinnamylaldehyde derivatives of property, and its application.Such structural formula of compound is: this derivant can be obtained through condensation reaction by the heterocyclic compound containing amino and cinnamic aldehyde.As the derivant of cinnamic aldehyde, except having the performances such as antibacterial anticorrosion, antiviral, also there is the feature such as high stable, gentleness, therefore can substitute cinnamic aldehyde and be widely used in the field product such as household chemicals, food, medicine, feedstuff.

Description

A kind of cinnamylaldehyde derivatives and application thereof
Technical field
The present invention relates to a kind of good stability, remarkably productive cinnamylaldehyde derivatives, particularly relate to this analog derivative in day With the application in chemicals, medicine, food and feedstuff.
Background technology
Cinnamic aldehyde (Cinnamaldehyde) is a kind of aldehydes organic compound, sticks thick liquid for yellow, exists in a large number In the plants such as Cortex Cinnamomi.In nature, naturally occurring cinnamic aldehyde is transconfiguration, and this molecule is to connect on an acrylic aldehyde Connect a phenyl, therefore can be considered as a kind of Propenal derivative, be that the chief active of Chinese medicine Cortex Cinnamomi volatile oil becomes Point.Cortex Cinnamomi is the dry bark of Lauraceae aiphyllium plant Cortex Cinnamomi, and it is mainly distributed on Guangdong, Guangxi, Yunnan and Fujian etc., its The Oleum Cinnamomi volume of production in middle Guangdong and Guangxi Provinces accounts for about the 80% of world wide production, also has on a small quantity in Sichuan, Guizhou, Hunan, Jiangxi, Zhejiang Cultivation.Cinnamic aldehyde is also naturally occurring in the plants essential oils such as hyacinth, Flos Rosae Rugosae, wide flower bud perfume.
Cinnamic aldehyde has two kinds of isomers of cis and trans, existing commercial cinnamic aldehyde cinnamic aldehyde that is the most natural or that synthesize, It it is all transisomer.
(trans) cinnamic aldehyde (cis) cinnamic aldehyde
The performances such as antibacterial, the anticorrosion of cinnamic aldehyde highlight, thus its application is widely.Tan Longfei, thank to little Mei etc. and respectively it is killed Bacterium sterilization antiseptic property is studied, and particularly has significant inhibitory activity to fungus, to escherichia coli, bacillus subtilis, gold Staphylococcus aureus, Staphylococcus albus, Typhoid and paratyphoid first bacillus, streptococcus pneumoniae, aerobacteria, Bacillus proteus, anthrax Bacillus, Salmonella enteritidis vibrio cholera etc. all have good inhibitory activity, and notable to gram positive bacteria bactericidal effect, Can be used for treating the multiple disease caused because antibacterial infects.
It is reported, cinnamic aldehyde has antiulcer, strengthens gastrointestinal movement, and its mechanism of action is due to ulcer activities factor Suppression and the reinforcement of defending factors, and suppress gastric mucosa current potential to reduce and to caused by mucosa.In addition, Cortex Cinnamomi Aldehyde can reduce enzymatic activity.Cinnamic aldehyde system armaticity stomach invigorating carminative, has the stimulation of mitigation to the intestines and stomach, can promote saliva and Gastric secretion, strengthens digestive function, releases gastrointestinal smooth muscular spasm, alleviates intestinal cramps pain.
Cinnamic aldehyde is known as safe and nontoxic material (21CFR 182.60), U.S.'s spices and extract by U.S. FDA Maker association (FEMA) is considered the food aroma constituent (FEMA, 1965) of safety non-toxic, and food additive joint specialist is entrusted It is safe (JECFA No.656) that member's meeting (JECFA) is also considered as cinnamic aldehyde as food additive.
Agricultural expert studies discovery, and cinnamic aldehyde, can be to dynamic in feed additive with its exclusive antibacterial and bactericidal action Thing nutrient digestion produces positive role.Research shows, cinnamic aldehyde can increase the secretion of animal bile, adds Cortex Cinnamomi in daily ration Aldehyde has been demonstrated to stimulate intestinal mucosa and the activity of pancreas digestive enzyme.There is scholar to add cinnamic aldehyde in daily ration of broiler, can change Kind feedstuff palatability, improves feed digestion utilization rate, promotes and improve growth of animal performance and animal product quality, it addition, Can effectively prevent feed spoilage corrupt, and extend the shelf lives of product.
Cinnamic aldehyde may be used for food and plays anti-corrosive fresh-keeping effect, Heilongjiang Bayi Agricultural Reclamation University's Foodstuffs Academy cinnamic aldehyde pair The antisepsis of meat products finds after carrying out parallel comparative study, and cinnamic aldehyde all has inhibitory action to different strain, to Aspergillus flavus Inhibitory action be especially apparent, under same dose, use cinnamic aldehyde make the food preservation phase extend about 1 week than potassium sorbate, What is more important, cinnamic aldehyde itself is as a kind of food spice, harmless to human body totally nontoxic, GB GB/T 2076- The allowing of 2011 regulations uses it as food additive, can be used for preparing meat, flavoring agent, oral care implement, chewing gum, Confection essence.
Cinnamic aldehyde better performances, application are extensive, but due to its reasons in structure, determine its have volatile, oxidizable, The features such as Odor stimulation, variable color, poorly water-soluble, have a strong impact on its application extensiveness and intensiveness, embody a concentrated expression of following some:
The most in atmosphere, easily it is oxidized to cinnamic acid and goes bad；
2. there is yellow or light green yellow, affect its application in formula, especially water white transparency system；
3. there is intense stimulus abnormal smells from the patient, there is peppery sense and have burning sensation；
4. there is dissolubility poor, be insoluble in water and glycerol, have a strong impact on compatibility and availability；
5. having highly volatile big, lasts is poor.
For overcome with present on shortcoming, scientific research personnel carries out derivant and parcel and processes, to improving it cinnamic aldehyde To light, heat, air equistability and reduction penetrating odor；By the parcel to cinnamic aldehyde, improve stability and dissolubility；Logical Cross formation nanoemulsions and microcapsule technology, improve storage stability.
Zhang Yuanyuan etc. carry out the synthesis of derivant to cinnamic aldehyde, the neighbour that has no irritating odor with cinnamic aldehyde as Material synthesis Nitro cinnamaldehyde, alpha-bromo-cinnamaldehyde and containing hydrophilic hydroxyl and the cinnamic aldehyde hydroxyl sulfoacid sodium of sulfonate functional groups, aobvious Work reduces odor problem, but owing to aldehyde radical still exists, its stability does not get a promotion, and introduced nitro, The group such as halogen, sulfonic group, and there is the features such as zest is big, toxicity is high, by-product is many in these groups, therefore this improvement is not There is bigger actual application value.
Qian Liangliang etc. carry out inclusion by beta-schardinger dextrin-to cinnamic aldehyde and improve its stability, and this clathrate is applied to product After, slowly discharging cinnamic aldehyde, and reach to play antibacterial effect at food surface, test proves have good mildew-resistant effect, Its safety Shelf-life can be improved.To some degree, improve stability and the dissolubility of cinnamic aldehyde, have bigger Progressive, but due to the intervention of macromole, the compatibility with system is poor, additionally along with release and the consumption of cinnamic aldehyde, effect Can progressively disappear, therefore its retention cycle is the most preferable, still has bigger room for improvement.
Cinnamic aldehyde, by microcapsule technology, is wrapped in microcapsule by Xie Fan etc., and its stability obtains certain raising, and Playing good control release action, result shows: in room temperature condition storage, and the retention rate of cinnamic aldehyde can be over time Extending and slowly decline, after 3 months, its retention rate still reaches 97%, shows that microcapsule cinnamic aldehyde is at room temperature stored stable.The method Similar to cyclodextrin processing method, microcapsule, to temperature, formula system existence and stability problem, affects its range of application.
More than study, the improvement that relatively direct use cinnamic aldehyde is the biggest, can solve in a way some or Railway Project, but all can not solve the problems such as oxidizable, water solublity, volatility, zest and color and luster simultaneously.
Summary of the invention
It is an object of the invention to provide a kind of good stability, remarkably productive cinnamylaldehyde derivatives；
Another object of the present invention is to the application providing this analog derivative in food；
Another object of the present invention is to the application providing this analog derivative in medicine；
The present invention also provides for a kind of for providing the application in household chemicals of this analog derivative；
Further object of the present invention is to provide the application at feedstuff of this analog derivative.
The technical solution used in the present invention is as follows:
A kind of cinnamylaldehyde derivatives, this derivant has a structure shown in formula I:
I
Wherein L can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH；
Wherein M can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH；
Wherein N can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH；
The wherein arbitrary integer of m=2～10；
Wherein X can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH、ph-CH=CH-CH=N-；
Wherein Y can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH、ph-CH=CH-CH=N-；
Wherein Z can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH、ph-CH=CH-CH=N-；
The wherein arbitrary integer of n=2～15.
Described alkyl be described alkyl can be straight chained alkyl or the substituted-phenyl of C3～C16, can be methyl, second Base, propyl group or butyl.
The preparation method of cinnamylaldehyde derivatives of the present invention, prepares with method with reference to prior art:
By the hexa-atomic oxa-ring containing amino with cinnamic aldehyde in a suitable solvent, condensation, use synthesis mode can be: solid phase Polishing, microwave catalysis method, ultrasonic；The method for purifying and separating used, including column chromatography and recrystallization method, it is thus achieved that mesh Mark compound.
Table 1 is parameter in the present invention this analog derivative parts of product information obtained and preparation reaction thereof:
Note: 1. α=-CH2OH, β=-OH, γ=ph-CH=CH-CH=N-, Δ=-COOH, ∑=-CH3；
Derivant of the present invention can be applied in household chemicals, medicine, food, feedstuff.
Beneficial effect produced by the present invention:
Derivant of the present invention, except retaining the characteristic of cinnamic aldehyde itself, such as antibacterial anticorrosion, antiviral, antitumor, the property such as fresh-keeping Can, also there is cinnamic aldehyde and do not have the advantage that and characteristic:
1) excellent stability, to better tolerance such as oxygen, light, heat, heavy metals；
2) non-volatility, will not run off by its active component because of volatilization so that activity reduces；
3) low irritant and sensitization；
4) good water solubility, will not affect the performance of product because of water solubility problems；
5) compatibility is good, it is simple to use in formula system；
6) derivant is white solid, the most tasteless；
7) this derivant antiseptic property relatively cinnamic aldehyde has promoted.
Owing to this series compound has as above these features, therefore, can be widely applied to household chemicals, food, medicine The product such as product, feedstuff.
Cinnamylaldehyde derivatives of the present invention can be widely used in household chemicals as preservative, can be used for washing Hair cream, shampoo, hair conditioner, setting agent, hair-waving and hair dye, suppurative mastitis, Cleansing Foam, bath oil, liquid soap, beauty soap, baby Soap, to skin and hair action temperature and, there is good bacteriostasis and sterilization performance, the rotten etc. of product can be prevented；Can be as anticorrosion Agent can be used for dental products, such as collutory, toothpaste, dentifrice, has sterilization, antibacterial, the function in nursing oral cavity；Should as preservative For cosmetic skin product, such as nursing astringent, emulsion, facial cream, gel, facial milk cleanser, sunscreen cream, hand cream etc.；Can conduct Anti-dandruff agent, as in hair care product, after with the addition of this analog derivative, can increase the affinity to hair, have protection The function of hair, has antisepsis and sterilization ability simultaneously, and derivant of the present invention is also used as synergetic effect additive, with tradition anti-dandruff agent Compounding use, can reduce the consumption of tradition district anti-dandruff agent, reduce the zest to skin, reduce sensitization probability.
Cinnamylaldehyde derivatives of the present invention can be used for food, as antifungus agent, prevents going mouldy of food, and this analog derivative is readily soluble Yu Shui, is widely used as Petaso, sausage, cake, the antistaling agent of cookies and moon cake, the antifungus agent of cake, adds suitably in moon cake This compounds of ratio, can make it keep delicate fragrance, fresh, storage life up to more than 4 weeks, add and can extend guarantor in cake Deposit phase 2～5 days, additionally can be applicable to strengthen baby food, old people food, instant food, functional food, butter, milk powder, refining The varieties of food items such as breast, margarine, vegetable oil, Petaso, sausage, chocolate, chewing gum.
Additionally cinnamylaldehyde derivatives of the present invention can be applied in medicine, antivirus action, infected by influenza can be played Show superpower inhibitory activity.
According to the cinnamylaldehyde derivatives of the present invention, there is good anti-mildew bactericidal action, make an addition in feedstuff, feedstuff can be made Preserve the most mouldy, invariant color or spoiled for a long time.
Detailed description of the invention
The preparation of embodiment 1 derivant (1a)
R:=CH-CH=CH-Ph
Under room temperature, by 7.8g cinnamic aldehyde (0.06mol) and 5.1g(0.01mol) compound a add be dried mortar in, grinding In alms bowl after mix homogeneously, quickly grind 20 minutes, then at the airtight preservation of room temperature 12 hours, after thin layer analysis monitoring reaction completes, add Enter 5.0ml ethanol (75%), grind 15 minutes, sucking filtration, absolute ethanol washing three times, after solid vacuum drying, obtain white powder Shape solid, yield 83%(is in terms of raw material a), fusing point 175 DEG C (decomposition).
The preparation of embodiment 2 derivant (1b)
R:=CH-CH=CH-Ph
Under room temperature, by 1.0g deionized water, it is anti-that 7.8g cinnamic aldehyde (0.06mol) and 5.0g(0.01mol) compound a add microwave Answer in device, in 60 DEG C of microwave radiations 10 minutes, be cooled to room temperature, after thin layer analysis monitoring reaction completes, add the anhydrous second of 7.5ml Alcohol, continues to grind 10 minutes, sucking filtration, absolute ethanol washing three times, after solid vacuum drying, obtains white powdery solids, yield 75%(is in terms of raw material b), fusing point 161 DEG C (decomposition).
The preparation of embodiment 3 derivant (1c)
Being prepared with reference to embodiment 2, by 1.5g water, 3.9g cinnamic aldehyde (0.03mol) and 5.1g(0.01mol) compound c add Enter reactor.After post processing, obtain white powdery solids, yield 69%.
The preparation of embodiment 4-7 derivant (1d-1f, 1i)
Being prepared with reference to embodiment 1, rate of charge is according to amino: cinnamic aldehyde=1:3(thing mass ratio) carry out and yield situation is shown in Table 1.
The preparation of embodiment 8-10 derivant (1g-1h, 1j)
The reaction condition provided according to table 1 by each material, feeds intake according to amino: cinnamic aldehyde=1:3(thing mass ratio) carry out, put into Ultrasonic reactor, yield is shown in Table 1.
Embodiment 11 derivant 1a-j solubility experiment
Derivant 1a-j sample is carried out respectively dissolubility measurement, result such as table 2 below:
As seen from the above table, after cinnamic aldehyde derivatization, dissolubility significantly promotes, and can well be dissolved in water and add to formula.
Embodiment 12 ambient stable Journal of Sex Research
Derivant 1a-j sample carries out stability study, and weighing 0.5g sample is in weighing botle respectively, is placed in 25 DEG C of calorstats In, place 6 months, periodically carry out HPLC content detection, the results are shown in Table 3:
Result shows, cinnamic aldehyde content is greatly reduced, and derivant the most significantly reduces.
Embodiment 13 acceleration for stabilization Journal of Sex Research
Derivant 1a-j sample is accelerated stability study, under the conditions of 48 DEG C, places 3 months, use HPLC to contain Amount detection, the results are shown in Table 4:
According to upper table 4, this series cinnamic aldehyde derivatization being accelerated study on the stability, result shows, each derivant is respectively provided with Well stability, it is the least that content reduces percentage ratio.
Embodiment 14 derivant 1a-j minimal inhibitory concentration (MIC) is measured
Derivant 1a-j carries out minimal inhibitory concentration detection (MIC) measure, use agar dilution to test, each derivant MIC detects data such as table 5 below:
From data in table, this analog derivative to golden staphylococcus, escherichia coli, bacillus pyocyaneus, Pseudomonas cepacia, white The rejection ability of color candidiasis, aspergillus niger, chlosma etc. is better than cinnamic aldehyde compared with cinnamic aldehyde.
Embodiment 15 moon-cake mildew-proof is tested
Mycete separates: take common PDA culture medium, carries out the separation of Superior fungus by GB GB5009.15 mycete yeast counting Identify.With serious pollution sample uses 10 dibbling methods, from the moon cake up-sampling that goes mouldy, is placed in 28 DEG C of incubators and cultivates.
The mycete mixing spore suspension 0.5mL(4 pieces of surface spray-paintings respectively of commercially available moon cake being separated to returns containing about 100/mL Receive mycotic spore), it is placed in plain polypropylene packaging bag (500mL), put into the RQA scraps of paper a piece of (every is loaded with respectively simultaneously The cinnamic aldehyde of 0mg, 20mg, 20mg 1b, 20mg 1j), sealing is placed on 28 DEG C of incubators and cultivates, perusal moon cake mildew feelings Condition, observes 20 days altogether, the results are shown in Table 6.
Result is visible, and the preservativity of cinnamylaldehyde derivatives is better than cinnamic aldehyde.
The embodiment 16 application in Chinese herbal medicine beverage
Folium Mori, Fructus Phyllanthi each 10g and 0.1g Flos Chrysanthemi are added in 20g water, heating extraction, and it is concentrated into 2.0mL, add 0.5g Mel, 0.1g Herba Menthae, 0.01g compound 1a or 1e mix homogeneously, 100mL dissolved dilution, mix thoroughly and filter.
Observe sample muddiness or Precipitation situation, be shown in Table 7.
The embodiment 17 application in feed for pet
18.0g Saccharum Sinensis Roxb., 18.0g soy sauce, 2.0g chicken oil being added in 950.0g water, strong stirring becomes baste, standby.Distinguish again 550.0g Carnis Gallus domesticus is twisted into filling；Equivalent Rhizoma Solani tuber osi, Fructus Colocasiae Esculentae, Semen Pisi sativi (30.0g), 45.0g Radix Ipomoeae and 50.0g Radix Dauci Sativae mix and are cut into Granular (grain < 3mm), with 60.0g corn starch, 25.0g alginate jelly, 21.0g wheat flour, 16.0g Saccharum Sinensis Roxb., 15.0g compound dimension life Element powder, 12.0g Sal, 3.0g enzymic bloody powder, 1.2g foline, 1.5g compound 1i and the mixing of 80.0g water, stir and make filling Shape, is placed in dish steaming 20min, cooling, constant temperature 1.0h in 0～2 DEG C of ice-water bath, takes out the fritter being cut into about 20mm, can Preserve more than December to never degenerate.
The embodiment 18 application in milk product
By 10.0g high-fructose corn syrup, 9.0g dairy base, 0.29g lactoprotein, 0.19g pectin, 0.15g lactic acid, 0.035g compound 1d, 0.67mg eat magnesium oxide, add 100g pure water, mix homogeneously.
By thing pasteurize mixed above, and it is exposed to light 8 hours, and it is done ratio with being not added with 1d sample Relatively, appearance goes out it and has more preferable stability.
The embodiment 19 application in O/W type protective skin cream
It is heated separately to 65 ~ 70 DEG C by biphase, under stirring, aqueous phase is added in oil phase.Stirring cooling, adds spice at 40 DEG C.
The embodiment 20 application in moisturiser
A, B are separately heated to 70 ~ 75 DEG C, and after being then under agitation added in A by B, stirring, to 40 ~ 45 DEG C, adds C.Continue Continuous stirring 15 ~ 20 minutes, is cooled to room temperature packaging.
The embodiment 21 application in nourishing elastin
A, B phase being heated separately to 75 DEG C, B is added to A phase, emulsifying 3 minutes (7500rpm), then stirring is cooled to 45 DEG C, Add C phase, be uniformly mixed, discharging.
The embodiment 22 application in soap table facial milk cleanser
By A phase raw material, being heated with stirring to 80-85 DEG C, weigh B phase raw material, stirring adds to A phase, and temperature controls at 80-85 DEG C, continue stir about 30-60 minute, make saponification complete；Weighing C phase raw material again, stirring adds, and temperature controls at about 80 DEG C, When temperature is down to 50 DEG C, add D phase raw material, continue stirring, be cooled to room temperature, discharging.

Claims (7)

1. a cinnamylaldehyde derivatives, its structural formula shown in formula I:
I
Wherein L can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH；
Wherein M can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH；
Wherein N can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH；
The wherein arbitrary integer of m=2～10；
Wherein X can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH、ph-CH=CH-CH=N-；
Wherein Y can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH、ph-CH=CH-CH=N-；
Wherein Z can be-H, alkyl ,-OH ,-COOH ,-CH2COOH、-CH2OH、ph-CH=CH-CH=N-；
The wherein arbitrary integer of n=2～15.
Cinnamylaldehyde derivatives the most according to claim 1, described alkyl can be straight chained alkyl or the replacement of C3～C16 Phenyl.
Cinnamylaldehyde derivatives the most according to claim 1, it is characterised in that: described n is the arbitrary integer of 2～15, excellent Select 3-8.
4. the application in household chemicals of the cinnamylaldehyde derivatives described in claim 1.
5. the application in medicine of the cinnamylaldehyde derivatives described in claim 1.
6. the application in food of the cinnamylaldehyde derivatives described in claim 1.
7. the application in feedstuff of the cinnamylaldehyde derivatives described in claim 1.
CN201610706797.6A 2016-08-23 2016-08-23 A kind of cinnamylaldehyde derivatives and application thereof Pending CN106279304A (en)

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CN111110088A (en) * 2020-02-05 2020-05-08 青岛美莱雅生物科技有限公司 Preparation method and anti-corrosion process of konjak facial puff
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