CN106905207B - A kind of low temperature synthesizes-depressurizes the method that azeotropic dehydration coupling technology prepares Maillard reaction intermediate - Google Patents
A kind of low temperature synthesizes-depressurizes the method that azeotropic dehydration coupling technology prepares Maillard reaction intermediate Download PDFInfo
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- CN106905207B CN106905207B CN201710022237.3A CN201710022237A CN106905207B CN 106905207 B CN106905207 B CN 106905207B CN 201710022237 A CN201710022237 A CN 201710022237A CN 106905207 B CN106905207 B CN 106905207B
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- C07—ORGANIC CHEMISTRY
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- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
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- C—CHEMISTRY; METALLURGY
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- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
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Abstract
The invention discloses a kind of low temperature to synthesize-depressurize the method that azeotropic dehydration coupling technology efficiently prepares Maillard reaction intermediate, the heating of the aqueous solution of amino acid and reduced sugar is reduced rapidly air pressure at that same temperature after a certain period of time to be dehydrated to 40mbar or less, restore system to normal temperature and pressure when flowing out to no fraction, food-grade ethanol is added into gained siccative, it is evaporated under reduced pressure after being sufficiently mixed, obtains Maillard reaction intermediate solid product.Compared with traditional methanol is heated to reflux and prepares the method for intermediate, technology disclosed in this invention greatly reduces production cost, and meet green, science, sustainable Industrial Design Idea, and transformation rate is higher among gained Maillard reaction and has stronger edible safety, can be used as food additives and directly applies in food.Compared with water phase alternating temperature Maillard reaction technology, the conversion ratio of intermediate is improved 370.0% by technology disclosed in this invention, has stronger innovative and significant progress.
Description
Technical field
The invention belongs to food additives manufacture fields, are related to Maillard reaction technology, specially in low temperature synthesis-decompression
The method that azeotropic dehydration coupling technology prepares Maillard reaction intermediate.
Background technique
Maillard reaction is the nonenzymatic browning reaction being widely present in food processing and storage, directly affects food
Flavor, flavour, color and the nutritive value of product are the important research contents in Food Chemistry field.Maillard reaction technology is one
The newer flavors and fragrances production application technology of item, has in tobacco essence and food flavor especially meat flavoring and widely answers
With.
In the Maillard reaction primary stage, addition is carried out between the carbonyl and amino of reduced sugar, addition product rapid dehydration turns
Become schiff bases, then be cyclized the glycosyl amine for forming corresponding N- and replacing, aldose is transformed into through Amadori rearrangement reactivity
1- amino -1- deoxidation -2- ketose；Ketose is then transformed into the 2- amino -2- deoxidation -1- aldehyde for having reactivity through Heyns rearrangement
Sugar.Primary Maillard reaction does not generate fragrance, does not also cause brown stain, but its product is extremely important fixedness fragrance precursor
Object.Compared to the final product after complete reaction, these Maillard reaction intermediates will not be straight after being added in food or tobacco
Connect the intensification for causing color and strong fragrance, but can crack as wind during burning and sucking in the deep processing of food and tobacco
Taste substance release comes out, therefore has the fragrant stability of good cause, shows wide application prospect.
In current prior art, the preparation of Amadori rearrangement product (ARP) or Heyns rearrangement product (HRP) is mainly adopted
It is prepared with methanol eddy method.Methanol height is inflammable, explosive, and has certain toxicity, nervous system and blood system to human body
System influences maximum, even the steam of methanol can also cause the damage of human respiratory tract's mucous membrane and eyesight.With methanol as solvent plus
Heat reflux prepares the safety that ARP and HRP do not have production, and production cost and Environmental costs are very high, are unfavorable for ARP's and HRP
Industrialized production, therefore have a kind of inexpensive, free of contamination novel green method substitution prior art to appear.Two-stage alternating temperature
Although Maillard reaction realizes the water phase preparation of Maillard reaction intermediate, but the conversion ratio of intermediate need to be improved,
There are more schiff bases (glycosyl amine) not to be fully converted to ARP or HRP in product.Therefore it is needed during aqueous phase reactions
Moisture is removed, to promote conversion of the schiff bases in water phase (glycosyl amine) to ARP or HRP, intermediate transformation rate is improved, realizes that beauty is drawn
The safe and efficient preparation of moral reaction intermediate.
Summary of the invention
Against the shortcomings and deficiencies of the above prior art, the present invention provides a kind of low temperature to synthesize-depressurize azeotropic dehydration coupling
The method that connection technology prepares Maillard reaction intermediate.Using water as solvent, amino acid and sugar are heated under certain condition and sent out
Raw Maillard reaction.Schiff bases dehydration occurs after synthesis under normal pressure during decompression dehydration, promotes the height of ARP or HRP
Effect conversion, is azeotroped off moisture remaining in siccative using food-grade ethanol and water after the reaction was completed, and tentatively divided
From purifying, ARP or HRP is obtained.
The purpose of the present invention is achieved through the following technical solutions:
A kind of low temperature synthesizes-depressurizes the method that azeotropic dehydration coupling technology prepares Maillard reaction intermediate, and feature exists
In comprising the following steps that:
(1) a certain amount of amino acid and reduced sugar are taken, water is added to form solution, adjusting pH value of solution to 7~8, when heating one section
Between Maillard reaction occurs；
(2) it reduces reaction system air pressure to be dehydrated to 40mbar or less, system vacuum degree is reduced to 0 to when flowing out without fraction,
It is simultaneously stopped heating, obtains siccative；
(3) a certain amount of food-grade ethanol is added into siccative obtained by step (2), siccative and food-grade ethanol is filled
Divide stirring, obtain mixture, be evaporated under reduced pressure, removes food-grade ethanol and residual moisture, obtain siccative；
(4) a certain amount of food-grade ethanol is added into siccative obtained by step (3), siccative and food-grade ethanol is filled
Divide mixing, is filtered under diminished pressure, obtains clear filtrate, filtrate decompression is evaporated, obtain siccative again；
(5) treatment process 1-5 times of step (4) is repeated to siccative obtained by step (4), finally depressurizes gained clear filtrate
Evaporation, obtains the solid product of ARP or HRP.
Preferably, in step (1), used amino acid is lysine, alanine, aspartic acid, cysteine, egg ammonia
One kind of salt or combinations thereof of the sour and described amino acid；Used reduced sugar is xylose, arabinose, glucose, fructose
One kind or combinations thereof.
Preferably, in step (1), when the parts by weight of the reduced sugar used are 10, the parts by weight of used amino acid
For 2-20, the parts by weight of water are 100-800.
Preferably, in step (1), heating temperature is 70-100 DEG C, and the Maillard reaction time is 20-180min.
Preferably, in step (3), used ethyl alcohol is dry food grade ethyl alcohol；The weight of the water used in step (1)
When amount part is 10, the parts by weight of food-grade ethanol used in step (3) are 5-20.
Preferably, in step (3) and step (4), the temperature of the reduction vaporization is 20-40 DEG C, vacuum degree 0.02-
0.06MPa。
Low temperature of the invention synthesizes-depressurizes that azeotropic dehydration coupling technology prepares ARP or the method for HRP has compared with prior art
There is following remarkable advantage:
(1) ARP and HRP is usually heated to reflux synthesis in anhydrous methanol at present, and using with irritation, combustibility
Organic acid as catalyst, these preparation methods often generate toxic pollutant, there is biggish safety in actual production
Hidden danger, while higher cost, it is difficult to realize industrialized production, therefore the preparation of Maillard reaction intermediate only rests on theory and grinds
Study carefully the stage.Water phase low-temperature fabrication of the present invention then can be achieved water phase and prepare Maillard reaction intermediate, and select
Processing aid is only food-grade ethanol, reduces the accounting cost, safety cost and Environmental costs of production, and technology is full
Foot green, science, sustainable Industrial Design Idea, and edible safety with higher, can be used as food additives
It directly applies in food or cigarette product.
(2) in the technology that traditional organic solvent reflux prepares ARP or HRP, the reaction time is 4-8 hours, and this hair
The bright aqueous phase preparation method need to only react 20-180min and can be obtained the ARP or HRP of higher conversion, greatly shorten anti-
Between seasonable, production cost is reduced, it is with higher innovative and advanced.
(3) Maillard reaction temperature is usually at 100 DEG C -150 DEG C in flavors and fragrances industry at present, to obtain more flavor
Substance.Under this reaction condition, Maillard reaction rate is fast, and side reaction is more, and reaction mechanism is complicated, among Maillard reaction
Body is not easy to be enriched with, and conversion ratio is extremely low, is unfavorable for the production preparation of ARP and HRP.Low temperature synthesis-decompression disclosed in this invention is total
Boiling dehydration coupling technology reduces the reaction temperature of traditional Maillard reaction, realizes the controllability of reaction process.
(4) it is anti-with two-stage alternating temperature Mei Lade that low temperature disclosed in this invention, which synthesizes-depressurize azeotropic dehydration coupling technology,
Based on answering technology, the new technology that azeotropic dehydration is formed is depressurized during low-temp reaction.With alternating temperature Maillard reaction technology phase
Than the conversion ratio of intermediate greatly improved in the technology of the present invention, has very strong innovative and significant progress.
(5) purification technique of existing ARP or HRP is based on ion-exchange chromatography, silica gel column chromatography, the operation of these methods
Cumbersome, higher cost and there are biggish security risks.And the purification process of ARP of the present invention or HRP is the precipitation method, benefit
It can be separated with other impurities with the good dissolubility of ARP or HRP in ethanol.It is easy to operate, low in cost, it is with higher
Industrial application value.
(6) method of water phase low temperature preparation Maillard reaction intermediate is with the processing technology of existing Maillard reaction essence
Based on technological innovation, the parameters such as used reactive mode, pH value regulative mode and dehydration temperaturre all with existing work
Skill is consistent, and the technology of water phase low temperature preparation ARP or HRP of the present invention can directly apply to practical life under the conditions of low cost
It produces, there is stronger practical application value.
Detailed description of the invention
Fig. 1 is xylose-methionine system ARP sample total ion chromatogram
Fig. 2 is xylose-methionine system ARP sample mass spectrogram
Fig. 3 is xylose-cysteine system ARP sample total ion chromatogram
Fig. 4 is xylose-cysteine system ARP sample mass spectrogram
Specific embodiment
For a better understanding of the present invention, the content of invention is furtherd elucidate below with reference to embodiment, but of the invention interior
Appearance is not limited solely to the following examples.
Embodiment 1
20kg methionine and 40kg xylose are taken, 800kg water is added to form solution, adjusts pH value of solution to 7.5,80 DEG C of heated at constant temperature
Maillard reaction occurs, system air pressure is reduced rapidly after 80min and is dehydrated to 40mbar or less, to (15min) when being flowed out without fraction
System vacuum degree is reduced to 0, is simultaneously stopped heating, obtains siccative, thereto be added 400kg food-grade ethanol, by siccative with
Food-grade ethanol is evaporated under reduced pressure under the conditions of 30 DEG C after being sufficiently mixed, and is removed food-grade ethanol and residual moisture, is obtained
To siccative.Siccative and food-grade ethanol are sufficiently mixed, are filtered under diminished pressure, clear filtrate, repeated evaporation, the step of mixing are obtained
Suddenly, finally gained clear filtrate is evaporated under reduced pressure, obtains intermediate solid product.
Obtained solid is dissolved in after water and is analyzed it by high performance liquid chromatography tandem mass spectrum analytical technology, is obtained total
Ion stream chromatogram and mass spectrogram (shown in such as Fig. 1, Fig. 2).
Embodiment 2
8kg cysteine and 20kg xylose are taken, 800kg water is added to form solution, pH value of solution to 7.5,90 DEG C of constant temperature is adjusted and adds
Maillard reaction occurs for heat, and system air pressure is reduced rapidly after 70min and is dehydrated to 40mbar or less, to when flowing out without fraction
System vacuum degree is reduced to 0 by (15min), is simultaneously stopped heating, obtains siccative, and the food-grade ethanol of 400kg is added thereto, will
Siccative is evaporated under reduced pressure under the conditions of 30 DEG C after being sufficiently mixed with food-grade ethanol, removes food-grade ethanol and residual water
Point, obtain siccative.Siccative and food-grade ethanol are sufficiently mixed, are filtered under diminished pressure, clear filtrate is obtained, repeated evaporation is mixed
The step of conjunction, finally gained clear filtrate was evaporated under reduced pressure, and obtained intermediate solid product.
Obtained solid is dissolved in after water and is analyzed it by high performance liquid chromatography tandem mass spectrum analytical technology, is obtained total
Ion stream chromatogram and mass spectrogram (shown in such as Fig. 3, Fig. 4).
Embodiment 3
15kg alanine and 30kg fructose are taken, 700kg water is added to form solution, adjusts pH value of solution to 7.4,90 DEG C of heated at constant temperature
Maillard reaction occurs, system air pressure is reduced rapidly after 100min and is dehydrated to 40mbar or less, to (13min) when being flowed out without fraction
System vacuum degree is reduced to 0, is simultaneously stopped heating, obtains siccative, thereto be added 700kg food-grade ethanol, by siccative with
Food-grade ethanol is evaporated under reduced pressure under the conditions of 30 DEG C after being sufficiently mixed, and is removed food-grade ethanol and residual moisture, is obtained
To siccative.Siccative and food-grade ethanol are sufficiently mixed, are filtered under diminished pressure, clear filtrate, repeated evaporation, the step of mixing are obtained
Suddenly, finally gained clear filtrate is evaporated under reduced pressure, obtains intermediate solid product.
Embodiment 4
10kg glycine and 20kg galactolipin are taken, 800kg water is added to form solution, pH value of solution to 8.0,90 DEG C of constant temperature is adjusted and adds
Maillard reaction occurs for heat, and system air pressure is reduced rapidly after 90min and is dehydrated to 40mbar or less, to when flowing out without fraction
System vacuum degree is reduced to 0 by (15min), is simultaneously stopped heating, obtains siccative, and the food-grade ethanol of 800kg is added thereto, will
Siccative is evaporated under reduced pressure under the conditions of 30 DEG C after being sufficiently mixed with food-grade ethanol, removes food-grade ethanol and residual water
Point, obtain siccative.Siccative and food-grade ethanol are sufficiently mixed, are filtered under diminished pressure, clear filtrate is obtained, repeated evaporation is mixed
The step of conjunction, finally gained clear filtrate was evaporated under reduced pressure, and obtained intermediate solid product.
Comparative example
According to the method that two-stage alternating temperature Maillard reaction water phase prepares ARP, 20kg methionine and 40kg xylose are taken, is added
800kg water forms solution, and adjusting pH value of solution to 7.5 is placed in Maillard reaction bottle, and first 80 DEG C of reaction different times add half Guang
Propylhomoserin, then temperature is improved to 120 DEG C of pyroreaction 120min, measure suction of the alternating temperature maillard reaction product at wavelength 420nm
Luminosity determines the corresponding low-temp reaction condition (reaction time 95min) of the most shallow sample of color.(80 DEG C) under the reaction conditions
Maillard reaction occurs for heated at constant temperature, stops heating after 95min, measures methionine-xylose system by high performance liquid chromatography
Transformation rate is 11.45% among Maillard reaction.
According to fig. 2 mass spectrogram fragment ion information it is found that fragment ion be molecular ion be dehydrated or decarboxylation formed, push away
Break its molecular ion peak MH+It is 282, the relative molecular mass of the substance is 281, molecular formula C10H19O6NS is xylose-egg ammonia
The ARP of acid system.
According to the fragment ion information of Fig. 4 mass spectrogram it is found that fragment ion is that molecular ion is dehydrated or decarboxylation is formed, push away
Break its molecular ion peak MH+It is 254, the relative molecular mass of the substance is 253, molecular formula C8H15O6NS is-half Guang of xylose
The ARP of propylhomoserin system.
Maillard reaction intermediate prepared by comparative example and embodiment 1 is divided respectively by high performance liquid chromatography
Analysis, the intermediate transformation rate of comparative example preparation is 11.45%, and measuring 1 conversion ratio of embodiment is 53.82%, more existing water
Phase Maillard reaction method improves 370.0%, it was demonstrated that the method for water phase low temperature preparation Maillard reaction intermediate of the present invention has
It is higher innovative and advanced.
The water that the experiment of above-described embodiment uses is distilled water, and sugar and amino acid use food-grade, remaining chemical reagent is equal
Pure to analyze, it is chromatographically pure that chemical reagent used is tested in High Performance Liquid Chromatography/Mass Spectrometry analysis.High Performance Liquid Chromatography/Mass Spectrometry inspection
Survey condition are as follows: the splitter for analysis is C18Reversed performance liquid chromatographic column, the mobile phase used are ultrapure water and acetonitrile, into
Gradient elution, flow velocity 0.3mL/min are carried out with mobile phase after sample, column temperature is 45 DEG C.The ionic means that mass spectral analysis selects for
ESI+, capillary voltage 3.5kV, orifice potential 20V, ion source temperature are 100 DEG C, and desolvation temperature is 400 DEG C, are taken off
Solvent stream speed is 700L/h, and taper hole air-flow velocity is 50L/h, and collision energy is 6V, and detector voltage is 1800V.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent substitution, improvement and etc. done be should be included within the scope of the present invention.
Claims (5)
1. a kind of low temperature synthesizes-depressurizes the method that azeotropic dehydration coupling technology prepares Maillard reaction intermediate, which is characterized in that
It comprises the following steps that:
(1) a certain amount of amino acid and reduced sugar are taken, water is added to form solution, adjusts pH value of solution to 7-8, heating a period of time is sent out
Raw Maillard reaction；Heating temperature is 70-100 DEG C, and the Maillard reaction time is 20-180min；
(2) it reduces reaction system air pressure to be dehydrated to 40mbar or less, system vacuum degree is reduced to 0 to when flowing out without fraction, simultaneously
Stop heating, obtains siccative；
(3) a certain amount of food-grade ethanol is added into siccative obtained by step (2), siccative and food-grade ethanol is carried out abundant
Stirring, obtains mixture, is evaporated under reduced pressure, and removes food-grade ethanol and residual moisture, obtains siccative；
(4) a certain amount of food-grade ethanol is added into siccative obtained by step (3), siccative and food-grade ethanol is carried out abundant
Mixing, is filtered under diminished pressure, obtains clear filtrate, filtrate decompression is evaporated, obtain siccative again；
(5) treatment process 1-5 times of step (4) is repeated to siccative obtained by step (4), and finally gained clear filtrate is depressurized and is steamed
Hair, obtains the solid product of ARP and/or HRP.
2. according to the method described in claim 1, it is characterized by: used amino acid is lysine, third in step (1)
Propylhomoserin, aspartic acid, cysteine, methionine and one kind of salt of the amino acid or combinations thereof；Used reduced sugar is
One of xylose, arabinose, glucose, fructose or combinations thereof.
3. according to the method described in claim 1, it is characterized by: in step (1), when the parts by weight of the reduced sugar used are 10
When, the parts by weight of used amino acid are 2-20, and the parts by weight of water are 100-800.
4. according to the method described in claim 1, it is characterized by: used ethyl alcohol is dry food grade second in step (3)
Alcohol；When the parts by weight of the water used in step (1) are 10, the parts by weight of food-grade ethanol used in step (3) are 5-
20。
5. according to the method described in claim 1, it is characterized by: in step (3) and step (4), the temperature of the reduction vaporization
Degree is 20-40 DEG C, vacuum degree 0-0.06MPa.
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| CN110710668B (en) * | 2019-10-18 | 2023-05-12 | 江南大学 | Method for improving yield of Amadori rearrangement product based on mechanism of inhibiting degradation of Amadori rearrangement product by adding deoxysugar ketone to tea polyphenol |
| CN113788866B (en) * | 2021-09-14 | 2023-09-26 | 江南大学 | Method for preparing Maillard intermediate by spray drying-vacuum drying |
| CN113735934B (en) * | 2021-09-14 | 2023-08-08 | 江南大学 | Method for selectively preparing peptide Maillard reaction intermediate and glycopeptide cross-link |
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| GB836694A (en) * | 1955-04-07 | 1960-06-09 | Unilever Ltd | Flavouring substances and their preparation |
| US3231472A (en) * | 1961-03-10 | 1966-01-25 | Kolmar Laboratories | Method of increasing water-absorbing ability of human skin and composition therefor |
| GB1514910A (en) * | 1974-07-02 | 1978-06-21 | Unilever Ltd | Amadori compounds and their use to flavour foods |
| US4592917A (en) * | 1984-04-16 | 1986-06-03 | Nestec S.A. | Chicken flavorants and processes for preparing them |
| PL171319B1 (en) * | 1992-03-03 | 1997-04-30 | Torf Ets | Method of obtaining a composition suitable for pharmaceutical and/or cosmetical use |
| EP1252825A1 (en) * | 2001-04-25 | 2002-10-30 | Société des Produits Nestlé S.A. | Flavouring compositions |
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