CN104178345A - Preparation method of glucose/glutamic acid Maillard reaction flavor for cigarettes - Google Patents
Preparation method of glucose/glutamic acid Maillard reaction flavor for cigarettes Download PDFInfo
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Abstract
The invention relates to the technical field of flavors for cigarettes, and particularly discloses a preparation method of a glucose/glutamic acid Maillard reaction flavor for cigarettes, which is characterized in that by using glucose and glutamic acid as raw materials, the material ratio, reaction solvent, reaction time, reaction temperature and system pH are controlled, and the products are graded and separated to obtain the low-molecular-weight volatile product capable of effectively improving sensation quality of cigarettes and the high-molecular-weight product with the molecular weight of 3-6kD. The accurate control on the cigarette glucose/glutamic acid Maillard reaction process and the fine after-treatment on the products are performed to obtain the low-molecular volatile products with favorable cigarette perfuming effect and the high-molecular products, thereby implementing fine processing of glucose/glutamic acid Maillard reaction, and enhancing the application value of the reaction products in cigarette perfuming.
Description
Technical field
The present invention relates to tobacco aromatics using field, specifically a kind of method of utilizing glucose/L-glutamic acid Maillard reaction to prepare tobacco aromatics using.
Background technology
Maillard reaction is the browning reaction (Non-enzymatic browning) of the non-enzymatic catalysis that occurs between aminocompound and reducing sugar, reaction is through complicated course, the final mixture generating containing various small molecules and high molecular brown even black, wherein macromolecule product is also referred to as melanoid (Melanoidins).Maillard reaction can produce a large amount of aroma components, has been used to prepare all kinds of essence and flavoring agents, sweetener.Because no matter reaction is from reaction or product, all can regard as natural, these perfume bases are regarded as " natural " by internal authority mechanism, thereby its application Yi Guangshou various countries concern, become the study hotspot in the fields such as organic chemistry, food chemistry, flavor chemistry, foodstuffs industry, tobacco industry.
The impact of the reaction conditions that Liu Guozhen etc. have studied the synthetic fragrance-enhancing tobacco agent of L-glutamic acid and glucose response on product perfuming effect.Result shows, the glucose of mol ratio 1:2 and L-glutamic acid have good flavouring effect at 100 DEG C, the product that reacts 2h, and in reaction system, add a small amount of acetaldehyde, can promote the generation (Liu Guozhen of multiple volatility aroma component, Zhu Wei, Huanglong etc. the Maillard reaction of L-glutamic acid and glucose, tobacco science and technology, 2002,10:30-33).Impact (the Wei Mingjie of the reaction conditions that the Maillard reaction that Zhu Zhizhi etc. have studied fructose and proline(Pro) and Chinese date extract generates fragrance-enhancing tobacco agent on product perfuming effect, Zhang Hongtao, Zhu Zhizhi etc., fructose reacts and applied research in tobacco with the Maillard of proline(Pro), Anhui agronomy circular, 2009,15:26-28; Zhu Zhizhi, Liao Xincheng, Li Guangzhao etc., Maillard reaction and the applied research in tobacco thereof of Chinese date extract, Anhui agronomy circular, 2008,14:40-42).Sun Fengling etc. have prepared 18 kinds of single amino acids and the Maillard reaction product of glucose and the Maillard reaction product of aminoacids complex, protolysate and glucose, two groups of kilnitamins that are suitable for flue-cured tobacco perfuming are filtered out, and study the impact (Sun Fengling of reaction conditions on product fragrance characteristic, Cai Miaoyan, Li Bing, Maillard reaction and the effect of product in tobacco flavoring thereof, Guangdong chemical industry, 2005,1:26-29; Sun Fengling, Cai Miaoyan, Cai Jin etc., the impact research of the Maillard reaction product under differential responses condition on cigarette igniting and sucking quality, Chinese Tobacco Science, 2005,4:5-7).Shanghai Institute Of Technology is taking L-arabinose and amino acid as raw material, prepared colory flavouring essence for tobacco (CN201110305727.7[P] .2012-4-4) with microwave heating method; In Hubei, cigarette discloses a kind of sugar and amino acid of utilizing and has reacted the method (CN201310268308.X[P] .2013-9-18) of preparing tobacco aromatics using and regulation and control thereof; In Hubei, cigarette also discloses a kind of method of utilizing Radix Glycyrrhizae extractum, sugar and proline(Pro) reaction to prepare tobacco aromatics using (CN201310270107.3[P] .2013-9-25); In Guangdong, cigarette and South China Science & Engineering University disclose a kind of method of utilizing offal extract and amino acid and saccharide compound to prepare cigarette response class spices (CN201210443210.9[P] .2013-4-17); Company of RISESUN and Hongta Group disclose a kind of method of utilizing offal extract and other to be rich in carbohydrate and amino acid whose natural perfume extract preparation feedback type tobacco aromatics using (CN201110371446.1[P] .2012-6-20); Hongta Group and Tian Hong company adopt enzymolysis solution and the compounded amino acid-respons of compound Chinese herb extract, and by the reactant preparing by membrane separation technique according to molecular weight and the functional staging treating (CN201410013826.1[P] .2014-4-9) of carrying out.
In general, the preparation technology of tobacco aromatics using field Maillard reactant is relatively extensive at present, the tradition preparation method of " treating different things alike " and the use-patterns of " one pot of use " of adopting more.Because Maillard reaction product composition is very complicated, the product that traditional method obtains exists in the time of application that specific aim is strong, feature is outstanding to some extent, DeGrain and the defect such as quality is unstable.Therefore, be necessary, from reaction process control and product postprocessing two aspects, Maillard is reacted to the processing technology research that becomes more meticulous, exploitation high-quality Maillard spices, this is conducive to further improve the development of exploitation level of Maillard reaction product, further excavate the using value of Maillard reaction product in tobacco, enrich characteristic cigarette perfume material kind.
Summary of the invention
A kind of preparation method of glucose/L-glutamic acid Maillard reaction flavor for cigarette that object of the present invention provides based on above-mentioned present Research just, by the control of feed ratio, reaction solvent, reaction times, temperature of reaction, system pH and the fractional separation of product, obtain effectively improving the small molecules amount volatile products of cigarette organoleptic quality and the molecular weight macromole product at 3kD ~ 6kD.
The object of the invention is to be achieved through the following technical solutions:
A kind of preparation method of glucose/L-glutamic acid Maillard reaction flavor for cigarette, by glucose and L-glutamic acid 1:0.3 ~ 2 in molar ratio, feed intake and be incorporated in ethanol water mixed solvent, regulation system pH8 ~ 10, oil bath reacting by heating certain hour, after reaction finishes, reaction product is cooled to rapidly to room temperature, removes by filter insolubles, obtain head product; Adopt ethyl acetate to extract head product, extraction liquid is removed after organic solvent with rotary evaporation after anhydrous sodium sulfate drying, obtains small molecules amount volatile products.Or adopt rotary evaporation to remove after most of water the aqueous portion after ethyl acetate extraction, lyophilize, the solid product obtaining adopts gel permeation chromatographic column chromatography, according to molecular weight, product is carried out to fractional separation, detect convection current part by the uv-absorbing at 280nm, 360nm and 420nm place monitors simultaneously, according to the elution curve of 280 nm, 360 nm and the drafting of 420nm place uv-absorbing, collecting to wash out in earlier stage has strong absorption at 280 nm places but absorbs very weak stream part at 360 nm and 420nm; Collected stream part rotary evaporation is removed after most of water, after lyophilize, obtained target macromole product, its molecular weight is between 3kD ~ 6kD.
Described ethanol water mixed solvent, alcohol concn is 40 ~ 60%.
The mass percent of described glucose and L-glutamic acid total mass and ethanol water mixed solvent is 20 ~ 60%.
Adopt sodium bicarbonate, sodium hydroxide or potassium hydroxide to regulate pH.
Described Heating temperature is 100 ~ 120 DEG C, and be 2 ~ 8h heat-up time.
Described small molecules amount volatile products, are to adopt with the isopyknic ethyl acetate of head product to extract respectively after head product 3 times, merge organic phase, and rotary evaporation is removed and obtained after organic solvent, is 0.5 ~ 2.0% with respect to the productive rate of the total amount that should feed intake.
Described gel permeation chromatographic column chromatography, employing be Bio-gel P-6 gel post (2 ~ 6cm × 50 ~ 200cm), carry out wash-out as moving phase with ultrapure water, flow velocity is 0.2 ~ 1.0mL/min.In the time that coloring matter flow to column bottom, elutriant is collected with the speed of 3 ~ 10min/ pipe, while all outflow to coloring matter on post, wash-out finishes, draw sample elution curve according to 280nm, 360nm and 420nm place absorbancy, and then according to elution curve, collecting to wash out in earlier stage has strong absorption at 280 nm places but absorbs very weak object flow part at 360 nm and 420nm.
Described target macromole molecular weight of product is between 3kD ~ 6kD, and nitrogen element content 6.5% ~ 7.0% (can record by ultimate analysis
), be 30 ~ 60% with respect to the productive rate of column chromatography applied sample amount.
Small molecules amount volatile products of the present invention or macromole product are added in cigarette with certain proportion, can effectively enrich cigarette smoke note, improve fragrance matter, increase perfume quantity, reduce assorted gas and pungency, there is good tobacco flavoring effect.The addition of its small molecular amount volatile products is tobacco quality 0.001～0.01%, and addition manner, for being mixed with perfuming solution with dissolve with ethanol, is evenly sprayed onto in pipe tobacco; The addition of macromole product is 0.01～0.05% of tobacco quality, and addition manner, for being mixed with perfuming solution by water dissolution, is evenly sprayed onto in pipe tobacco.
For the preparation of glucose/L-glutamic acid Maillard reaction flavor for cigarette, advantage of the present invention is mainly:
(1) water Maillard reacts normally separately using water as reaction solvent, and the present invention is using ethanol water mixed liquid as solvent.In solvent, the introducing of ethanol can effectively promote the process of reaction, has effectively improved the growing amount of small molecules volatile products and target macromole product, and then improves the productive rate of target product.
(2) adopt gel filtration chromatography to carry out fractional separation to product, can effectively isolate the component with good perfuming cigarette effect, remove simultaneously perfuming cigarette is had to negative effect, have the strong component
absorbing at 360 nm and 420nm place.
(3) the small molecules amount volatile products that prepared by the present invention mainly contain 1-hydroxyl-2-acetone, 3-hydroxy-2-butanone, 1-hydroxy-2-butanone, 2,5-dimethyl-4-hydroxyl-3 (2H)-furanone, 2,3-dihydro-3,5-dihydroxyl-6-methyl-4H-pyrone, 3, the ketone compounds such as 5-dihydroxyl-2-methyl-4H-pyrone, 2-cyclopentenes-Isosorbide-5-Nitrae-diketone, 3-methyl cyclopentanedione; Pyrazine, 2-methylpyrazine, 2,5-dimethylpyrazine, 2, the pyrazine compounds such as 6-dimethylpyrazine and 2，3，5-trimethylpyrazine; The furfuran compounds such as 5 methyl furfural, furfuryl alcohol and 5-methyl furfuryl alcohol; The VFA compounds such as acetic acid, propionic acid and 4 hydroxybutyric acid.Wherein, it is fragrant and sweet that ketone compounds and furfuran compound can effectively strengthen Jiao of cigarette smoke, pyrazine compounds can be given the nutty of cigarette smoke feature and cure perfume (or spice), VFA compounds can regulate smoke behavior, improve flue gas comfortableness, therefore, prepared small molecules amount volatile products have good tobacco flavoring effect.
(3) the macromole product thermo-cracking that prepared by the present invention can generate pyrazine, 2-methylpyrazine, 2,5-dimethylpyrazine, 2, the pyrazine compounds such as 6-dimethylpyrazine and 2，3，5-trimethylpyrazine; The azoles such as pyrroles, 2-acetyl pyrrole; 1-hydroxyl-2-acetone, 2,5-dimethyl-4-hydroxyl-3 (2H)-furanone, 2,3-dihydro-3,5-dihydroxyl-6-methyl-4H-pyrone, 3, the ketone compounds such as 5-dihydroxyl-2-methyl-4H-pyrone, 2-cyclopentenes-Isosorbide-5-Nitrae-diketone, 3-methyl cyclopentanedione; The furfuran compounds such as 5 methyl furfural, furfuryl alcohol and 5-methyl furfuryl alcohol, Jiao that can strengthen cigarette smoke is fragrant and sweet, cure perfume (or spice) and nutty, has good tobacco flavoring effect.
In a word, the present invention is by the accurate control of glucose/L-glutamic acid Maillard reaction process and the aftertreatment that becomes more meticulous of product for cigarette, small molecules volatile products and the macromole product of good perfuming cigarette effect are obtained having, realize the processing that becomes more meticulous of glucose/L-glutamic acid Maillard reaction, improved the using value of reaction product in perfuming cigarette.
Embodiment
The present invention is described further below in conjunction with embodiment, but does not limit the present invention.
embodiment 1:
Take glucose 100mmol and L-glutamic acid 50mmol and be mixed in the aqueous ethanolic solution of 100mL 30%, regulation system pH9.0,105 DEG C of oil bath reacting by heating 3h, are cooled to rapidly room temperature by reaction product after reaction finishes, and remove by filter insolubles, obtain head product.Adopt 100mL × 3 ethyl acetate to extract head product, combining extraction liquid, and with after anhydrous sodium sulfate drying, rotary evaporation is removed organic solvent, obtains the small molecules volatile products 0.21g of brown paste, is 1.69% with respect to the productive rate of the total amount that feeds intake.
This product is mixed with to perfuming solution with dissolve with ethanol, is evenly sprayed onto on pipe tobacco by 0.005% of pipe tobacco weight, after baking, roll into cigarette.Smoking result shows, Jiao of flue gas is fragrant and sweet, it is fragrant outstanding to bake and bank up with earth, and fragrance matter is improved, and perfume quantity obviously increases, and assorted gas and pungency obviously reduce.
embodiment 2:
Taking glucose 100mmol and L-glutamic acid 100mmol is mixed in the aqueous ethanolic solution of 100mL 50%, regulation system pH9.0,105 DEG C of oil bath reacting by heating 6h, are cooled to rapidly room temperature by reaction product after reaction finishes, and remove by filter insolubles, obtain head product.Adopt 100mL × 3 ethyl acetate to extract head product, combining extraction liquid, and with after anhydrous sodium sulfate drying, rotary evaporation is removed organic solvent, obtains the small molecules volatile products 0.31g of brown paste, is 1.89% with respect to the productive rate of the total amount that feeds intake.
This product is mixed with to perfuming solution with dissolve with ethanol, is evenly sprayed onto on pipe tobacco by 0.005% of pipe tobacco weight, after baking, roll into cigarette.Smoking result shows, Jiao of flue gas is fragrant and sweet, it is fragrant outstanding to bake and bank up with earth, and fragrance matter is improved, and perfume quantity obviously increases, and assorted gas and pungency obviously reduce.
embodiment 3:
Take glucose 100mmol and L-glutamic acid 150mmol is mixed in the aqueous ethanolic solution of 100mL 50%
), regulation system pH9.0,105 DEG C of oil bath reacting by heating 6h, are cooled to rapidly room temperature by reaction product after reaction finishes, and remove by filter insolubles, obtain head product.After adopting 100mL × 3 ethyl acetate to extract head product, isolated aqueous portion adopts rotary evaporation to remove after most of water, and lyophilize, obtains solid head product 21.5g.
Get 1.0g solid head product, adopt the Bio-gel P-6 gel post of 2.5cm × 100cm to carry out gel permeation chromatographic column chromatographic separation, carry out wash-out with ultrapure water as moving phase, flow velocity is 0.5mL/min.In the time that coloring matter flow to column bottom, elutriant is collected with the speed of 5min/ pipe, while all outflow to coloring matter on post, wash-out finishes.Detecting convection current part by the uv-absorbing at 280nm, 360nm and 420nm place monitors, and draw sample elution curve according to 280nm, 360nm and 420nm place absorbancy, and then wash out and have strong absorption at 280 nm places early stage according to elution curve collection, but absorb very weak object flow part at 360 nm and 420nm.After collected stream part is merged, rotary evaporation is removed most of water, then lyophilize, obtains target macromole product 0.42g, is 42% with respect to the productive rate of column chromatography applied sample amount, and molecular weight is 3kD ~ 6kD.
This product is mixed with to perfuming solution by water dissolution, is evenly sprayed onto on pipe tobacco by 0.02% of pipe tobacco weight, after baking, roll into cigarette.Smoking result shows, Jiao of flue gas is fragrant and sweet, it is fragrant outstanding to bake and bank up with earth, and fragrance matter is improved, and perfume quantity obviously increases, and assorted gas and pungency obviously reduce.
Claims (7)
1. the preparation method of the Maillard of glucose/L-glutamic acid for a cigarette reaction flavor, it is characterized in that: by glucose and L-glutamic acid 1:0.3 ~ 2 in molar ratio, feed intake and be incorporated in ethanol water mixed solvent, regulation system pH8 ~ 10, oil bath reacting by heating certain hour, after reaction finishes, reaction product is cooled to rapidly to room temperature, removes by filter insolubles, obtain head product; Adopt ethyl acetate to extract head product, extraction liquid is removed after organic solvent with rotary evaporation after anhydrous sodium sulfate drying, obtains small molecules amount volatile products; Or adopt rotary evaporation to remove after most of water the aqueous portion after ethyl acetate extraction, lyophilize, the solid product obtaining adopts gel permeation chromatographic column chromatography, according to molecular weight, product is carried out to fractional separation, detect convection current part by the uv-absorbing at 280nm, 360nm and 420nm place monitors simultaneously, according to the elution curve of 280 nm, 360 nm and the drafting of 420nm place uv-absorbing, collecting to wash out in earlier stage has strong absorption at 280 nm places but absorbs very weak stream part at 360 nm and 420nm; Collected stream part rotary evaporation is removed after most of water, after lyophilize, obtained target macromole product, its molecular weight is between 3kD ~ 6kD.
2. the preparation method of glucose/L-glutamic acid Maillard reaction flavor for cigarette according to claim 1, is characterized in that: described ethanol water mixed solvent, alcohol concn is 40 ~ 60%.
3. the preparation method of glucose/L-glutamic acid Maillard reaction flavor for cigarette according to claim 1, is characterized in that: the mass percent of described glucose and L-glutamic acid total mass and ethanol water mixed solvent is 20 ~ 60%.
4. the preparation method of glucose/L-glutamic acid Maillard reaction flavor for cigarette according to claim 1, is characterized in that: adopt sodium bicarbonate, sodium hydroxide or potassium hydroxide to regulate pH.
5. the preparation method of glucose/L-glutamic acid Maillard reaction flavor for cigarette according to claim 1, is characterized in that: described Heating temperature is 100 ~ 120 DEG C, and be 2 ~ 8h heat-up time.
6. the preparation method of glucose/L-glutamic acid Maillard reaction flavor for cigarette according to claim 1, it is characterized in that: described small molecules amount volatile products, to adopt with the isopyknic ethyl acetate of head product to extract respectively after head product 3 times, merge organic phase, rotary evaporation is removed and is obtained after organic solvent, is 0.5 ~ 2.0% with respect to the productive rate of the total amount that should feed intake.
7. the preparation method of glucose/L-glutamic acid Maillard reaction flavor for cigarette according to claim 1, it is characterized in that: described gel permeation chromatographic column chromatography, what adopt is Bio-gel P-6 gel post (2 ~ 6cm × 50 ~ 200cm), carry out wash-out as moving phase with ultrapure water, flow velocity is 0.2 ~ 1.0mL/min; In the time that coloring matter flow to column bottom, elutriant is collected with the speed of 3 ~ 10min/ pipe, while all outflow to coloring matter on post, wash-out finishes, draw sample elution curve according to 280nm, 360nm and 420nm place absorbancy, and then according to elution curve, collecting to wash out in earlier stage has strong absorption at 280 nm places but absorbs very weak object flow part at 360 nm and 420nm.
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Cited By (4)
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| CN106539119A (en) * | 2017-01-12 | 2017-03-29 | 湖北中烟工业有限责任公司 | A kind of microwave handling method of burley tobaccos |
| CN106723315A (en) * | 2016-12-01 | 2017-05-31 | 华宝香精股份有限公司 | A kind of preparation method of electronic cigarette raw material |
| CN110862366A (en) * | 2019-11-07 | 2020-03-06 | 河南中烟工业有限责任公司 | Milk-flavor tobacco sweetener, preparation method and application in cigarettes |
| CN112931923A (en) * | 2021-02-02 | 2021-06-11 | 云南中烟工业有限责任公司 | Preparation method of specific molecular weight peptide Maillard intermediate and application of intermediate in tobacco flavor |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106723315A (en) * | 2016-12-01 | 2017-05-31 | 华宝香精股份有限公司 | A kind of preparation method of electronic cigarette raw material |
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| CN110862366A (en) * | 2019-11-07 | 2020-03-06 | 河南中烟工业有限责任公司 | Milk-flavor tobacco sweetener, preparation method and application in cigarettes |
| CN110862366B (en) * | 2019-11-07 | 2023-05-16 | 河南中烟工业有限责任公司 | Milk-flavored tobacco sweetener, preparation method and application thereof in cigarettes |
| CN112931923A (en) * | 2021-02-02 | 2021-06-11 | 云南中烟工业有限责任公司 | Preparation method of specific molecular weight peptide Maillard intermediate and application of intermediate in tobacco flavor |
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