CN108191679A - A kind of synthetic method of biologically active bread mould inhibitor - Google Patents
A kind of synthetic method of biologically active bread mould inhibitor Download PDFInfo
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- CN108191679A CN108191679A CN201810138307.6A CN201810138307A CN108191679A CN 108191679 A CN108191679 A CN 108191679A CN 201810138307 A CN201810138307 A CN 201810138307A CN 108191679 A CN108191679 A CN 108191679A
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- mould inhibitor
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D15/00—Preserving finished, partly finished or par-baked bakery products; Improving
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
Abstract
The invention discloses a kind of synthetic methods of biologically active bread mould inhibitor, include the following steps：(1) synthesis of imine intermediate：Be added in reaction tube the para hydroxybenzene amine of 1 structure of formula, 2 structure of formula to hydroxy-benzyl alcohol, catalyst system and catalyzing and solvent, valve seal is closed in oxygenation, and reaction tube is put into stirring oil bath pan, and heating stirring reaction a period of time obtains the imine intermediate of 3 structure of formula；(2) synthesis of bread mould inhibitor：Reaction tube valve is opened in cooling, adds in the formic acid of formula 4, and reaction tube valve is threaded to communicate with air, and heating reaction removes solvent after reaction, purified to obtain the bread mould inhibitor of 5 structure of formula；The bioactivity of the mould inhibitor is good, effectively inhibits the Penicillium notatum for causing bread and going mouldy, green aspergillus, rhizopus, reddish brown mould and white mould bacterium.
Description
Technical field
The invention belongs to food technology fields, and in particular to a kind of synthesis side of biologically active bread mould inhibitor
Method.
Background technology
Bread is made and is heated and manufactured food with five cereals (being usually wheat class) milling, using wheat flour as main original
Material, with yeast, egg, grease, sugar, salt etc. for auxiliary material, adds water to be modulated into dough, through over-segmentation, forming, provocation, bakes, cools down
Etc. the bakery product that is process of processes；Bread water content is big, rich in nutrition content, is placed in storage and sales process very short
Time may can moldy metamorphism, it is made to lose edible value, causes to waste, bread, which goes mouldy, not only causes larger economic damage
It loses, and the health of people is seriously endangered after eating by mistake.
Invention content
The object of the present invention is to provide a kind of synthetic methods of biologically active bread mould inhibitor, effective to press down
It is good the Penicillium notatum for causing bread and going mouldy, green aspergillus, rhizopus, reddish brown mould and white mould bacterium, the bioactivity of the mould inhibitor have been made.
The purpose of the present invention can be achieved through the following technical solutions：
A kind of synthetic method of biologically active bread mould inhibitor, includes the following steps：
(1) synthesis of imine intermediate
Be added in reaction tube the para hydroxybenzene amine of 1 structure of formula, 2 structure of formula to hydroxy-benzyl alcohol, catalyst system and catalyzing and solvent,
Valve seal is closed in oxygenation, and reaction tube is put into stirring oil bath pan, and heating stirring reaction a period of time obtains 3 structure of formula
Imine intermediate；
(2) synthesis of bread mould inhibitor
Reaction tube valve is opened in cooling, adds in the formic acid of formula 4, reaction tube valve is threaded to communicate with air, heating is anti-
Should, solvent is removed after reaction, it is purified to obtain the bread mould inhibitor of 5 structure of formula；
Above-mentioned synthetic reaction is shown below：
Further, the catalyst system and catalyzing described in step (1) is using RuCl2(dmso)4For metallic catalyst, alkali selects methanol
Sodium, ligand are dinaphthalene hexichol phosphorus, and structural formula is as shown in Equation 6：
Further, the para hydroxybenzene amine described in step (1), to hydroxy-benzyl alcohol, metallic catalyst, ligand, alkali molar ratio
It is 1:3.5-5:0.01:0.03:0.05.
Further, the solvent described in step (1) is acetonitrile, and the addition of solvent is to react the 2-4% of pipe volume, oil bath
Temperature is 95-102 DEG C, reaction time 8-12h.
Further, the addition of the formic acid described in step (2) is 2 times of para hydroxybenzene amine.
Further, the heating reaction temperature described in step (2) is 77-82 DEG C, reaction time 2.5-4h.
Further, the purification step described in step (2) is：Crude product uses 95% ethyl alcohol recrystallization, then will crystallization
The crude product gone out uses column chromatography, with petroleum ether:Dichloromethane=10:The mixed solvent of 2-3 is eluent separating-purifying.
Further, the bioactivity of the bread mould inhibitor is measured using inhibition mycelial growth rate method, the mycelia
Culture medium prescription is：100-150 parts of pure water, 20-50 parts of bean sprout juice, 20-30 parts of starch, 3-6 parts of honey, 3-6 parts of agar, urine
0.5-2 parts plain, 10% 0.3-1 parts of biphosphate sodium water solution, 5% 0.3-0.6 parts of sodium bicarbonate aqueous solution.
Further, mycelial growth rate method is inhibited to measure bread mould inhibitor bioactivity to be as follows：
(1) preparation of culture medium：Water, bean sprout juice and starch are added in beaker, rear small fire is boiled and continues to heat 10min,
Agar is stirring evenly and then adding into, honey and urea are added in after agar is completely dissolved, remaining water is added after stirring evenly, is stirred
Stop heating after uniformly, when being cooled to 50 DEG C, add in the biphosphate sodium water solution of 0.6g 10%, the bicarbonate of 0.3g 5%
Sodium water solution adjusts pH value to 6.8-7.6, is then divided in glass dish, is sealed using sterile sealed membrane, using moist heat sterilization
Method keeps the temperature 20-25min at 130 DEG C, has obtained solid medium；
(2) mould inhibitor of preparation with dimethylformamide is dissolved, is configured to the mould proof solution of a concentration of 0.1-0.5mg/ml,
Penicillium notatum, green aspergillus, rhizopus, reddish brown mould and white mold species are seeded in respectively on different glass dish culture mediums, respectively
It is punched on culture medium, mould proof solution is injected in hole, 48-72h is cultivated at 40-45 DEG C, calculates each mycelial growth inhibition rate.
The mechanism of action of bread mould inhibitor is：When bread mould inhibitor and the cell membrane contact of microorganism, melt with cell membrane
Conjunction progresses into cell, and the phenolic hydroxyl group and tertiary amine group in bread mould inhibitor pass through to works such as organelle, protein, nucleic acid
The effect of matter makes cellular content, enzyme, protein, nucleic acid damage, inhibits the activity of various metabolic enzymes in fungal cell so as to press down
The breeding of bacterium and mould processed, reaches restraining and sterilizing bacteria purpose.
Beneficial effects of the present invention：
(1) bread mould inhibitor prepared by the present invention can effectively inhibit to cause Penicillium notatum, green aspergillus, head mold that bread goes mouldy
Bacterium, reddish brown mould and white mould bacterium are measured using mycelial growth rate method is inhibited through calculating Penicillium notatum mycelial growth inhibition rate
It is 73.5%, green aspergillus hyphae growth inhibition ratio is 76%, and rhizopus mycelial growth inhibition rate is 83.5%, reddish brown fungal hyphae life
Long inhibiting rate is 88%, and white mould bacterium mycelial growth inhibition rate is 82%；It follows that there is the mould inhibitor good biology to live
Property；
(2) synthetic method of bread mould inhibitor of the invention only needs one pot of two step that can synthesize, and simplifies synthesis step, first
First to hydroxy-benzyl alcohol under the action of ruthenium catalyst system and catalyzing, the hydrogen that metal catalyst system is captured on alcohol is oxidized by oxygen, and dehydrogenation is formed
The condensation dehydration of aldehyde intermediate and para hydroxybenzene amine form imine intermediate, imine intermediate by formic acid proton turn to imines from
Son, then formate ion shift a negative hydrogen to imines ion, generate secondary amine, while release carbon dioxide, secondary amine can be with the
Two molecule aldehyde intermediates are condensed again as imines ion, and are restored by formate ion, generate tertiary amine, combine by means of hydrogen reaction and
The principle of Eschweiler-Clarke reactions, the more green raw polyol of use is a kind of synthetic method of completely new tertiary amine.
Specific embodiment
The technical solution in the embodiment of the present invention will be clearly and completely described below, it is clear that described implementation
Example is only part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention, this field is common
All other embodiment that technical staff is obtained without creative efforts belongs to the model that the present invention protects
It encloses.
Embodiment 1
A kind of synthetic method of biologically active bread mould inhibitor, includes the following steps：
(1) synthesis of imine intermediate
In 200mL reaction tubes add in add in magneton, the para hydroxybenzene amine of 10mmol, 40mmol to hydroxy-benzyl alcohol,
The sodium methoxide of 0.5mmol, the ligand dinaphthalene hexichol phosphorus of 0.3mmol, the catalyst RuCl of 0.1mmol2(dmso)4, add in 5ml second
Valve seal is closed in nitrile, oxygenation, and reaction tube is put into stirring oil bath pan, and the temperature of oil bath is 100 DEG C, and the reaction time is
10h, heating stirring reaction is to get to the imine intermediate of 3 structure of formula；
(2) synthesis of bread mould inhibitor
50 DEG C are cooled to, reaction tube valve is opened, adds in 20mmol formic acid, it is 80 DEG C to be heated to temperature, will react pipe valve
Door is threaded to communicate with air, reacts 3h, removes solvent after reaction, using 95% ethyl alcohol recrystallization, will then crystallize out
Crude product using column chromatography, with petroleum ether:Dichloromethane=10:The mixed solvent of 2-3 for eluent separating-purifying to get
To the bread mould inhibitor of 5 structure of formula, yield 88%, purity 98.8%；
Above-mentioned synthetic reaction is shown below：
The nucleus magnetic hydrogen spectrum result of gained target product 5 is：1H NMR(400MHz,CDCl3):δ 7.23 (d, J=8.2Hz,
4H), 7.11 (d, J=7.6Hz, 2H), 6.92 (d, J=7.7Hz, 4H), 6.77 (d, J=7.2Hz, 2H), 5.58 (s, 3H),
4.11(s,4H)；
The mass spectral results of gained target product 5 are：HRMS m/z(ESI+)calcd for C20H19NO3([M]+),
321.14,found 321.376。
Embodiment 2
The biological activity determination of bread mould inhibitor prepared by embodiment 1：Using inhibition mycelial growth rate method：
(1) preparation of culture medium：
100g water, bean sprout juice 30g and starch 20g are added in beaker, rear small fire is boiled and continues to heat 10min, stirring is equal
5g agar is added in after even, 5g honey and 1g urea are added in after agar is completely dissolved, 50g water is added after stirring evenly, stirring is equal
Stop heating after even, when cooling down 50 DEG C, biphosphate sodium water solution, the sodium bicarbonate of 0.3g 5% for adding in 0.6g10% are water-soluble
Liquid adjusts pH value to 6.9, is then divided in glass dish, is sealed using sterile sealed membrane, using moist hear heat test, at 130 DEG C
25min is kept the temperature, has obtained solid medium；
(2) mould inhibitor of preparation with dimethylformamide is dissolved, is configured to the mould proof solution of a concentration of 0.5mg/ml, it will be green
Mould, green aspergillus, rhizopus, reddish brown mould and white mold species are seeded in respectively on different glass dish culture mediums, are being trained respectively
It supports and is punched on base, mould proof solution is injected in hole, cultivates 48h at 42 DEG C, calculating Penicillium notatum mycelial growth inhibition rate is
73.5%, green aspergillus hyphae growth inhibition ratio is 76%, and rhizopus mycelial growth inhibition rate is 83.5%, reddish brown fungal hyphae growth
Inhibiting rate is 88%, and white mould bacterium mycelial growth inhibition rate is 82%；It follows that the mould inhibitor has good bioactivity.
Embodiment 3
The biological activity determination of bread mould inhibitor prepared by embodiment 1：Using inhibition mycelial growth rate method：
(1) preparation of culture medium：
100g water, bean sprout juice 21g and starch 30g are added in beaker, rear small fire is boiled and continues to heat 10min, stirring is equal
3g agar is added in after even, 3g honey and 2g urea are added in after agar is completely dissolved, 20g water is added after stirring evenly, stirring is equal
Stop heating after even, when cooling down 50 DEG C, add in the biphosphate sodium water solution of 0.5g 10%, the sodium bicarbonate water of 0.5g 5%
Solution adjusts pH value to 7.1, is then divided in glass dish, is sealed using sterile sealed membrane, using moist hear heat test, 130
DEG C heat preservation 20min, obtained solid medium；
(2) mould inhibitor of preparation with dimethylformamide is dissolved, is configured to the mould proof solution of a concentration of 0.1mg/ml, it will be green
Mould, green aspergillus, rhizopus, reddish brown mould and white mold species are seeded in respectively on different glass dish culture mediums, are being trained respectively
It supports and is punched on base, mould proof solution is injected in hole, cultivates 50h at 40 DEG C, calculating Penicillium notatum mycelial growth inhibition rate is
70%, green aspergillus hyphae growth inhibition ratio is 72%, and rhizopus mycelial growth inhibition rate is 77%, reddish brown fungal hyphae growth inhibition
Rate is 85%, and white mould bacterium mycelial growth inhibition rate is 80%；It follows that the mould inhibitor has good bioactivity.
Embodiment 4
The biological activity determination of bread mould inhibitor prepared by embodiment 1：Using inhibition mycelial growth rate method：
Culture medium prescription is：100-150 parts of pure water, 20-50 parts of bean sprout juice, 20-30 parts of starch, 3-6 parts of honey, agar
3-6 parts, 0.5-2 parts of urea, 0.3-1 parts of the biphosphate sodium water solution of 0.01mol, 5% sodium bicarbonate aqueous solution 0.3-0.6
Part；
(1) preparation of culture medium：
100g water, bean sprout juice 50g and starch 30g are added in beaker, rear small fire is boiled and continues to heat 10min, stirring is equal
6g agar is added in after even, 6g honey and 0.5g urea are added in after agar is completely dissolved, 10g water is added after stirring evenly, is stirred
Stop heating after uniformly, when cooling down 50 DEG C, biphosphate sodium water solution, the sodium bicarbonate of 0.6g 5% for adding in 1g10% are water-soluble
Liquid adjusts pH value to 7.5, is then divided in glass dish, is sealed using sterile sealed membrane, using moist hear heat test, at 130 DEG C
22min is kept the temperature, has obtained solid medium；
(2) mould inhibitor of preparation with dimethylformamide is dissolved, is configured to the mould proof solution of a concentration of 0.3mg/ml, it will be green
Mould, green aspergillus, rhizopus, reddish brown mould and white mold species are seeded in respectively on different glass dish culture mediums, are being trained respectively
It supports and is punched on base, mould proof solution is injected in hole, cultivates 72h at 45 DEG C, calculating Penicillium notatum mycelial growth inhibition rate is
72%, green aspergillus hyphae growth inhibition ratio is 74%, and rhizopus mycelial growth inhibition rate is 82.5%, reddish brown fungal hyphae growth suppression
Rate processed is 86.5%, and white mould bacterium mycelial growth inhibition rate is 83%；It follows that the mould inhibitor has good bioactivity.
Above content is only the design example and explanation to the present invention, affiliated those skilled in the art
Various modifications or additions are done to described specific embodiment or are substituted in a similar way, without departing from invention
Design or surmount range defined in the claims, be within the scope of protection of the invention.
Claims (9)
1. a kind of synthetic method of biologically active bread mould inhibitor, it is characterised in that：Include the following steps：
(1) synthesis of imine intermediate
Be added in reaction tube the para hydroxybenzene amine of 1 structure of formula, 2 structure of formula to hydroxy-benzyl alcohol, catalyst system and catalyzing and solvent, fill
Oxygen closes valve seal, and reaction tube is put into stirring oil bath pan, and heating stirring reaction a period of time obtains 3 structure of formula
Imine intermediate；
(2) synthesis of bread mould inhibitor
Reaction tube valve is opened in cooling, adds in the formic acid of formula 4, and reaction tube valve is threaded to communicate with air, heating reaction, instead
Solvent is removed after answering, it is purified to obtain the bread mould inhibitor of 5 structure of formula；
Above-mentioned synthetic reaction is shown below：
2. a kind of synthetic method of biologically active bread mould inhibitor according to claim 1, it is characterised in that：Step
Suddenly the catalyst system and catalyzing described in (1) is using RuCl2(dmso)4For metallic catalyst, alkali selects sodium methoxide, and ligand is dinaphthalene hexichol
Phosphorus, structural formula are as shown in Equation 6：
3. a kind of synthetic method of biologically active bread mould inhibitor according to claim 1, it is characterised in that：Step
Suddenly the para hydroxybenzene amine described in (1), be 1 to the molar ratio of hydroxy-benzyl alcohol, metallic catalyst, ligand, alkali:3.5-5:0.01:
0.03:0.05。
4. a kind of synthetic method of biologically active bread mould inhibitor according to claim 1, it is characterised in that：Step
Suddenly the solvent described in (1) is acetonitrile, and the addition of solvent is to react the 2-4% of pipe volume, and the temperature of oil bath is 95-102 DEG C, instead
It is 8-12h between seasonable.
5. a kind of synthetic method of biologically active bread mould inhibitor according to claim 1, it is characterised in that：Step
Suddenly the addition of the formic acid described in (2) is 2 times of para hydroxybenzene amine.
6. a kind of synthetic method of biologically active bread mould inhibitor according to claim 1, it is characterised in that：Step
Suddenly the heating reaction temperature described in (2) is 77-82 DEG C, reaction time 2.5-4h.
7. a kind of synthetic method of biologically active bread mould inhibitor according to claim 1, it is characterised in that：Step
Suddenly the purification step described in (2) is：Crude product uses 95% ethyl alcohol recrystallization, and the crude product crystallized out then is used column layer
Analysis method, with petroleum ether:Dichloromethane=10:The mixed solvent of 2-3 is eluent separating-purifying.
8. a kind of synthetic method of biologically active bread mould inhibitor according to claim 1, it is characterised in that：It should
Using mycelial growth rate method is inhibited to measure, the culture medium prescription of the mycelia is the bioactivity of bread mould inhibitor：It is pure
100-150 parts of water, 20-50 parts of bean sprout juice, 20-30 parts of starch, 3-6 parts of honey, 3-6 parts of agar, 0.5-2 parts of urea, 10%
0.3-1 parts of biphosphate sodium water solution, 5% 0.3-0.6 parts of sodium bicarbonate aqueous solution.
9. a kind of synthetic method of biologically active bread mould inhibitor according to claim 8, it is characterised in that：Suppression
Mycelial growth rate method processed measures bread mould inhibitor bioactivity and is as follows：
(1) preparation of culture medium：Water, bean sprout juice and starch are added in beaker, rear small fire is boiled and continues to heat 10min, stirring
Agar is added in after uniformly, honey and urea are added in after agar is completely dissolved, remaining water is added after stirring evenly, is stirred evenly
Stop heating afterwards, when being cooled to 50 DEG C, add in the biphosphate sodium water solution of 0.6g 10%, the sodium bicarbonate water of 0.3g 5%
Solution adjustment pH value is then divided in glass dish to 6.8-7.6, using the sealing of sterile sealed membrane, using moist hear heat test,
130 DEG C of heat preservation 20-25min, have obtained solid medium；
(2) mould inhibitor of preparation with dimethylformamide is dissolved, is configured to the mould proof solution of a concentration of 0.1-0.5mg/ml, it will be green
Mould, green aspergillus, rhizopus, reddish brown mould and white mold species are seeded in respectively on different glass dish culture mediums, are being trained respectively
It supports and is punched on base, mould proof solution is injected in hole, 48-72h is cultivated at 40-45 DEG C, calculates each mycelial growth inhibition rate.
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| CN201810138307.6A CN108191679A (en) | 2018-02-10 | 2018-02-10 | A kind of synthetic method of biologically active bread mould inhibitor |
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| CN201810138307.6A CN108191679A (en) | 2018-02-10 | 2018-02-10 | A kind of synthetic method of biologically active bread mould inhibitor |
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| CN201810138307.6A Withdrawn CN108191679A (en) | 2018-02-10 | 2018-02-10 | A kind of synthetic method of biologically active bread mould inhibitor |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3779796A (en) * | 1970-07-24 | 1973-12-18 | Ueno Fine Chemical Ind | Sodium propionate coated with sorbitan higher fatty acid ester and process for its preparation |
| JPS50743B1 (en) * | 1969-10-18 | 1975-01-11 | ||
| CN103371216A (en) * | 2012-04-24 | 2013-10-30 | 西姆莱斯有限公司 | Metal-complexing aroma compounds for use in aroma stabilization |
-
2018
- 2018-02-10 CN CN201810138307.6A patent/CN108191679A/en not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50743B1 (en) * | 1969-10-18 | 1975-01-11 | ||
| US3779796A (en) * | 1970-07-24 | 1973-12-18 | Ueno Fine Chemical Ind | Sodium propionate coated with sorbitan higher fatty acid ester and process for its preparation |
| CN103371216A (en) * | 2012-04-24 | 2013-10-30 | 西姆莱斯有限公司 | Metal-complexing aroma compounds for use in aroma stabilization |
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Application publication date: 20180622 |
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