CN112545046A - Composition capable of reducing free radical content in cigarette smoke and preparation method thereof - Google Patents
Composition capable of reducing free radical content in cigarette smoke and preparation method thereof Download PDFInfo
- Publication number
- CN112545046A CN112545046A CN202011470797.3A CN202011470797A CN112545046A CN 112545046 A CN112545046 A CN 112545046A CN 202011470797 A CN202011470797 A CN 202011470797A CN 112545046 A CN112545046 A CN 112545046A
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- Prior art keywords
- maillard reaction
- solid acid
- composition
- cigarette
- reaction intermediate
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Images
Classifications
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- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Manufacture Of Tobacco Products (AREA)
- Cigarettes, Filters, And Manufacturing Of Filters (AREA)
Abstract
The invention provides a composition capable of reducing the content of free radicals in cigarette smoke and a preparation method thereof, wherein the composition comprises a solid acid and a Maillard reaction intermediate, wherein the weight ratio of the solid acid to the Maillard reaction intermediate is 1: 5-1: 1000. further, the invention also provides a method for reducing the content of free radicals in cigarette smoke by using the composition, and a cigarette prepared from the composition. In the composition, the solid acid can catalyze the pyrolysis of the Maillard reaction intermediate, so that the Maillard reaction intermediate can release more antioxidant active substances at a lower temperature while increasing aroma, and has a certain promotion effect on reducing the content of free radicals in smoke.
Description
Technical Field
The invention belongs to the field of cigarettes, and particularly relates to a composition capable of reducing the content of free radicals in cigarette smoke, a preparation method of the composition and a method for reducing the content of free radicals in cigarette smoke by using the composition.
Background
The Maillard reaction is an important means for preparing thermal reaction type spices, and the complete Maillard reaction end product has rich flavor, but the flavor is quick to volatilize and not durable, and is easy to lose in the processing and storage processes. Maillard reaction intermediates are intermediates of Maillard reactions, which are mixtures of sugars and amino acids that undergo non-enzymatic browning when heated. The mixture contains very complicated components, and according to different browning degrees, the mixture contains micromolecular alpha-diketone and ester, heterocyclic derivatives (mainly furan rings and pyran rings) with complicated structures and browning products with high molecular weight. Maillard reaction intermediates are precursors of important aroma components, which generally do not have an aroma themselves, but can be converted and cleaved under heat to a variety of end product components of Maillard reactions. The type of flavour released is related to the sugars and amino acids used. The Maillard reaction intermediates prepared from different types of sugar and amino acid have different flavors. The difference in flavor is also related to the degree of Maillard reaction progress. The longer the reaction time, the more thorough the Maillard reaction proceeds and the flavor profile varies.
In daily life, active free radicals are generated in many cases. The active free radicals attack biological substances in human bodies, including unsaturated fatty acids, proteins, amino acids, DNA and the like, so that the mobility of cell membranes and the conformation of membrane proteins are changed, various diseases are directly or indirectly promoted, and health is harmed. Free radicals in the smoke produced by a cigarette are potentially harmful. The free radicals of the smoke comprise two kinds of solid-phase free radicals and gas-phase free radicals, the solid-phase free radicals have good stability and long service life, and the main components of the free radicals include quinone and semiquinone free radicals, partial polycyclic aromatic hydrocarbon free radicals, carbon and phosphorus free radicals and the like. The gas-phase free radicals mainly consist of alkyl free radicals and alkoxy free radicals, have high chemical reaction activity, can penetrate through the Cambridge filter sheet although the service life is short, and have potential hazard.
Maillard reactants and Maillard reaction intermediates are commonly used as a flavoring agent of cigarettes, but the capturing and annihilation effect of the Maillard reactants and the Maillard reaction intermediates on free radicals in smoke is not reported.
Disclosure of Invention
The invention aims to reduce the content of free radicals in cigarette smoke, and the inventor provides a composition capable of reducing the content of the free radicals in the cigarette smoke, wherein solid acid is adopted to catalyze the pyrolysis of a Maillard reaction intermediate, so that the Maillard reaction intermediate can release more antioxidant active substances (which can effectively reduce the content of the free radicals) at a lower temperature while flavoring, and has a certain promotion effect on reducing the content of the free radicals in the cigarette smoke.
Accordingly, in one aspect, the present invention provides a composition capable of reducing the content of free radicals in cigarette smoke, wherein the composition comprises a solid acid and a maillard reaction intermediate, wherein the weight ratio of the solid acid to the maillard reaction intermediate is 1: 5-1: 1000.
in one embodiment of the present invention, the solid acid is an oxide-based solid acid or a metal salt-based solid acid.
In one embodiment of the present invention, the oxide-based solid acid is selected from the group consisting of Al-based solid acids2O3-SiO2Mixed oxides based on Al2O3-B2O3Mixed oxides and based on ZrO2-MoO3One or more of the mixed oxides of (a).
In one embodiment of the present invention, the metal salt solid acid is selected from one or more of metal sulfate and metal phosphate.
In one embodiment of the present invention, the Maillard reaction intermediate is obtained by Maillard reaction of amino acid and saccharide at 50-200 deg.C.
In one embodiment of the present invention, the amino acid is selected from at least one of glycine, alanine, arginine, glutamic acid, leucine, and isoleucine.
In one embodiment of the present invention, the saccharide is selected from at least one of glucose, fructose, sucrose, lactose, mannose and galactose.
In another aspect, the present invention also provides a method of preparing a composition as described above, the method comprising: contacting the solid acid with the Maillard reaction intermediate.
In one embodiment of the invention, the contacting is carried out by triturating and mixing the solid acid and the solid maillard reaction intermediate; and/or by immersing the solid acid in a Maillard reaction intermediate solution.
In another aspect, the present invention also provides a method for reducing the content of free radicals in cigarette smoke, which comprises: the composition is added into the tobacco preparation of the cigarette, so that the free radical content in the smoke generated by the cigarette in use is reduced.
In another aspect, the invention also provides a cigarette, wherein the tobacco preparation used by the cigarette comprises the composition.
Compared with the prior art, the invention at least has the following beneficial technical effects:
(1) in the composition capable of reducing the content of free radicals in the cigarette smoke, the solid acid is used as a catalyst, so that the Maillard reaction intermediate is effectively thermally decomposed to release fragrance, and free radicals in released matters of the cigarette smoke are reduced to a certain extent, so that the composition has a harm reduction effect; (2) the composition capable of reducing the content of free radicals in the smoke of the cigarettes can be applied to the traditional cigarettes and can also be applied to the heating cigarettes; (3) the solid acid is cheap, easy to obtain and high in safety; and (4) the composition capable of reducing the content of free radicals in the cigarette smoke can be obtained by simply contacting, such as mixing or solution adsorption, the solid acid and the Maillard intermediate reactant, and the process is simple but has good effect.
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention and are incorporated in and constitute a part of this specification, illustrate embodiments of the invention and together with the description serve to explain the principles of the invention and not to limit the invention. In the drawings:
FIG. 1 shows DPPH radical scavenging rates of solid acid and alanine-glucose acid type Maillard reaction intermediate pyrolysis gas absorption liquid (300 ℃) in example 1; and is
FIG. 2 shows the DPPH radical scavenging rate of the solid acid and glycine-glucose base Maillard reaction intermediate pyrolysis gas absorption solution (300 ℃) in example 2.
Detailed Description
The following describes in detail specific embodiments of the present invention. It should be understood that the detailed description and specific examples, while indicating the present invention, are given by way of illustration and explanation only, not limitation.
The endpoints of the ranges and any values disclosed herein are not limited to the precise range or value, and such ranges or values should be understood to encompass values close to those ranges or values. For ranges of values, between the endpoints of each of the ranges and the individual points, and between the individual points may be combined with each other to give one or more new ranges of values, and these ranges of values should be considered as specifically disclosed herein.
Before describing the present invention in detail, it is to be understood that the terminology used herein is for the purpose of describing particular embodiments only, and is not intended to limit the scope of the present invention which will be limited only by the appended claims. For a more complete understanding of the invention described herein, the following terms are used, and their definitions are set forth below. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
In one aspect, the present invention provides a composition capable of reducing the content of free radicals in cigarette smoke, wherein the composition comprises a solid acid and a maillard reaction intermediate, wherein the weight ratio of the solid acid to the maillard reaction intermediate is 1: 5-1: 1000.
according to the invention, the weight ratio of the solid acid and the maillard reaction intermediates in the composition may be in the range of 1: 5-1: 1000, for example, the weight ratio of the solid acid to the maillard reaction intermediates may be 1: 10. 1: 20. 1: 50. 1: 100. 1: 200 or 1: 500, etc., but is not limited thereto. In a particular embodiment, the composition may consist only of the solid acid and the maillard reaction intermediates.
According to the present invention, the type of the solid acid is not particularly limited, and may be a common type of solid acid. For example, the solid acid may be a solid acid such as an oxide, a sulfide, a metal salt, a heteropoly acid, or the like. In a preferred embodiment of the present invention, the solid acid may be an oxide-based solid acid or a metal salt-based solid acid. Further, in a preferred embodiment of the present invention, the oxide-based solid acid may be selected from Al-based solid acids2O3-SiO2Mixed oxides based on Al2O3-B2O3Mixed oxides and based on ZrO2-MoO3One or more of the oxides of (a); the metal salt solid acid may be one or more selected from metal sulfate and metal phosphate. Further, the metal in the metal salt may be, for example, Fe, Al, Cu, or the like. Still further, the solid acid used in the present invention may more specifically be aNa2O:bAl2O3:cSiO2In the formula, can be a<0.1%, b/c ≈ 1/25 (or 1/10-1/30, for example), and may be generally obtained by firing alumina and silica at a certain molar ratio, wherein sodium oxide is an impurity, so that the content thereof is not controlled to be high.
According to the present invention, the term "maillard reaction", also known as non-enzymatic browning reaction, is a non-enzymatic browning reaction widely existing in the food industry, and is a reaction between a carbonyl compound (e.g. reducing saccharide) and an amino compound (e.g. amino acid and protein), which finally generates a brown or even black macromolecular substance melanoidin or melanoid through a complicated process, and is also known as carbonylamine reaction; the term "Maillard reaction intermediate" refers to an intermediate product during the Maillard reaction and can be obtained by carrying out an incomplete Maillard reaction from starting materials at a certain temperature.
Therefore, in a preferred embodiment of the present invention, the Maillard reaction intermediate can be obtained by carrying out Maillard reaction under 50-200 ℃ (e.g., 80 ℃, 100 ℃, 120 ℃, 150 ℃ or 180 ℃) from amino acids and saccharides (the molar ratio of the amino acids to the saccharides can be 1: 0.5-2, preferably 1: 1). Further, the maillard reaction can be carried out by a method well known to those skilled in the art, for example, by a basic method, i.e., catalyzing the above reaction with a basic catalyst, and adding an acidic reagent at the end of the reaction to adjust the pH to neutral; or may be carried out by an acidic method in which the above reaction is catalyzed with an acidic catalyst and an alkaline agent is added at the end of the reaction to adjust the pH to neutrality.
Still further, in a preferred embodiment of the present invention, the amino acid may be selected from at least one of glycine, alanine, arginine, glutamic acid, leucine, and isoleucine; the saccharide may be selected from at least one of glucose, fructose, sucrose, lactose, mannose and galactose. Based on the above-described selection of specific amino acids and saccharide species, it is understood that the Maillard reaction intermediates of the present invention can be obtained by Maillard reaction from any combination of the above-described amino acids and saccharides.
In another aspect, the present invention also provides a method of preparing a composition as described above, the method comprising: contacting the solid acid with the Maillard reaction intermediate.
In the production method provided by the present invention, the contacting of the solid acid and the maillard reaction intermediate may be performed by any means, and for example, may be performed in a state of being mixed in a solid phase, a liquid phase or a combination thereof. In a preferred embodiment of the present invention, the contacting may be carried out by triturating and mixing the solid acid and the solid maillard reaction intermediate; and/or may be performed by immersing the solid acid in a maillard reaction intermediate solution.
When the contacting is performed by mill-mixing the solid acid and the solid maillard reaction intermediate as described above, the mixing ratio of the solid acid and the solid maillard reaction intermediate may be 1: 5-1: 1000 (weight ratio). When the contacting is performed by immersing the solid acid in the maillard reaction intermediate solution as described above, the maillard reaction intermediate solution may be water, ethanol, propylene glycol, glycerol solution or a combination thereof having a concentration of 5 to 70% (by weight) of the maillard reaction intermediate, and the contacting may further comprise low temperature baking or air drying after the solid acid is immersed in the solution for 2 to 24 hours.
In another aspect, the present invention also provides a method for reducing the content of free radicals in cigarette smoke, which comprises: the composition is added into the tobacco preparation of the cigarette, so that the free radical content in the smoke generated by the cigarette in use is reduced.
In another aspect, the invention also provides a cigarette, wherein the tobacco preparation used by the cigarette comprises the composition.
According to the various methods for preparing the composition of the invention, the composition of the invention can be used for reducing the content of free radicals in the smoke of cigarettes or preparing cigarettes in different ways.
For example, when the cigarette is a heated cigarette, the solid composition of the invention can be uniformly mixed with tobacco powder to prepare a tobacco sheet, the tobacco sheet is wrapped by cigarette paper to form a tobacco section, and the tobacco section is connected with a cooling filter rod through tipping paper to form a low-temperature cigarette; the composition can be prepared into water, ethanol, propylene glycol, glycerol solution or a combination thereof, and then is uniformly mixed with tobacco powder to prepare tobacco sheet threads, the tobacco threads are wrapped by cigarette paper to form a tobacco section, and the tobacco section is connected with a cooling filter tip through tipping paper to form a low-temperature cigarette; the composition is prepared into water, ethanol, propylene glycol, glycerol solution or a combination thereof, and is uniformly applied to the surface of the tobacco sheet threads, the tobacco threads are wrapped by the cigarette paper to form a tobacco section, and the tobacco section is connected with a cooling filter tip through tipping paper to form a low-temperature cigarette; preparing the composition into a solution of water or ethanol or propylene glycol or glycerol, uniformly applying the solution on the surface of a tow to prepare a cooling filter rod, wrapping tobacco filaments by using cigarette paper to form a tobacco section, and connecting the tobacco section and the cooling filter rod through tipping paper to form a heated cigarette; the solid of the composition is uniformly applied to the silk bundle to prepare a cooling filter tip, the tobacco silk is wrapped by the cigarette paper to form a tobacco section, and the tobacco section is connected with the cooling filter tip through tipping paper to form a heating cigarette; and filling the composition solid in a cavity of the hollow section of the filter rod to prepare a cooling filter rod, wrapping tobacco filaments by cigarette paper to form a tobacco section, and connecting the tobacco section and the cooling filter rod through tipping paper to form a heating cigarette.
For another example, when the cigarette is a traditional cigarette, the composition of the invention can be prepared into a solution of water or ethanol or propylene glycol or glycerol, and the solution is uniformly applied to the surface of tobacco shreds, the tobacco shreds are wrapped by cigarette paper to form a tobacco section, and the tobacco section is connected with a filter rod through tipping paper to form a cigarette; the composition is prepared into a solution of water or ethanol or propylene glycol or glycerol, and is uniformly applied to the surface of cigarette paper, the cigarette paper wraps tobacco shreds to form a tobacco section, and the tobacco section is connected with a filter rod through tipping paper to form cigarette cigarettes; preparing the composition into a solution of water or ethanol or propylene glycol or glycerol, uniformly applying the solution on the surface of a tow to prepare a filter tip, wrapping tobacco shreds with cigarette paper to form a tobacco section, and connecting the tobacco section and the filter tip through tipping paper to form a cigarette; the solid of the composition is uniformly applied to the silk bundles to prepare the filter tip, the cigarette paper wraps the tobacco shreds to form a tobacco section, and the tobacco section is connected with the filter tip through tipping paper to form a cigarette.
The inventor of the invention finds that in the composition, the solid acid can catalyze the pyrolysis of the Maillard reaction intermediate, and the Maillard reaction intermediate can release more antioxidant active substances at a lower temperature (such as 200 ℃ or 300 ℃) while flavoring, so that the composition has a certain promotion effect on reducing the content of free radicals in smoke.
Hereinafter, the effects of the specific composition of the present invention will be described in detail by examples.
Examples
Example 1
Synthesis of acid method maillard reaction intermediate: glucose and alanine in a certain amount (1: 1 molar ratio) were reacted in 5% (ratio to the total weight of L-alanine and glucose) of malonic acid as a catalyst at 65 ℃ for 8h in four times (ratio to the total weight of L-alanine and glucose) of methanol. And after the reaction is completed, adding sodium hydroxide to neutralize the reaction product to be neutral, obtaining a Maillard reaction intermediate with the membrane molecular weight cut-off of 500-5000 by the obtained Maillard crude product through a membrane separator dialysis method, and then freeze-drying the Maillard reaction intermediate to remove the solvent or water in the Maillard reaction intermediate to obtain the solid Maillard intermediate.
To the Maillard reaction intermediate obtained as above, 10% by weight of a solid acid was added (the chemical composition of the solid acid used in the examples was represented by the molar ratio of the oxide: aNa)2O:bAl2O3:cSiO2In the formula a<0.1%, b/c 1/25) and mixed well.
Thermal cracking experiments were carried out at 200 deg.C, 300 deg.C and 400 deg.C for the pure Maillard reaction intermediate, and Maillard reaction intermediate + 10% solid acid, respectively. Lysis and analysis were performed using a CDS 5250T pyrolyser and Agilent 7890A-5975C GC gas chromatograph-Mass spectrometer. About 1mg of the sample was weighed and placed on quartz wool in a cracker tube, which was then placed on a cracker to be cracked. Cracking temperature rise procedure: the initial temperature was 50 ℃ and ramped up to the set pyrolysis temperature at 30 ℃/s for 5 s. The cracking atmosphere is helium, and the gas flow is as follows: 70mL/min, temperature of the cracker valve box: 280 ℃, transmission line temperature of the cracker: 280 ℃. GC-MS method: an elastic quartz capillary column; the stationary phase is 5% of phenyl-95% of methyl polysiloxane; the specification is [30m (length) × 0.25mm (inner diameter) × 0.25 μm (film thickness) ]; carrier gas flow, 1.0 mL/min; the split ratio is 100: 1; heating, wherein the initial temperature is 40 ℃, keeping for 3min, increasing to 240 ℃ at the speed of 10 ℃/min, increasing to 280 ℃ at the speed of 20 ℃/min, and keeping for 15 min; the mass spectrum transmission line temperature is 280 ℃; the ion source temperature is 230 ℃; the temperature of the quadrupole rods is 150 ℃; the mass scan range is 29-450 amu. The cleavage product results are shown in table 1 below:
TABLE 1 results of Py-GC/MS (90% N) of glucose-alanine Maillard reaction intermediates (acid method, molecular weight 500-5000kDa) in air atmosphere2+10％O2Atmosphere)
Table 1 shows the results of Py-GC/MS of glucose-alanine Maillard reaction intermediates (acid method, molecular weight 500-. It can be seen that the relative content of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one in the cracked gas increases upon addition of the solid acid, whereas 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one is a substance with a strong radical scavenging and antioxidant effect, as is well known to those skilled in the art.
The mixed sample is cracked in a tube furnace at 300 ℃, the current carrying cracked gas is carried in Ar atmosphere, and the absolute ethyl alcohol is used for absorbing, and the cracking time is 10 min. Taking 2mL of diluted cracked gas absorption liquid and 2mL of 0.1mmol/L DPPH ethanol solution, adding the diluted cracked gas absorption liquid and 2mL of 0.1mmol/L DPPH ethanol solution into the same test tube with a plug, shaking the solution uniformly, sealing and standing the solution at room temperature for 30min, taking a blank without adding a sample solution and taking the treatment without the composition as a control, measuring the absorbance at the wavelength of 517nm, and calculating the DPPH free radical scavenging rate by using the following formula:
clearance/% (a 0- (Ai-Aj))/a 0 × 100
In the formula: a0 is the absorbance of a DPPH solution without the addition of a composition according to the invention; ai is the absorbance of a DPPH solution after addition of a composition of the invention; and Aj is the absorbance of the composition of the invention, wherein a greater DPPH free radical clearance indicates greater antioxidant capacity.
As shown in FIG. 1, the removal rate of DPPH free radicals by the absorption liquid of the pyrolysis gas is obviously improved after solid acid is added during the pyrolysis at 300 ℃.
The application in heating cigarettes comprises the following steps: uniformly applying the mixed sample solid in a tow (the weight ratio of the sample solid to the tow is 1:400) to prepare a cooling filter rod, wrapping tobacco filaments with cigarette paper to form a tobacco section, connecting the tobacco section and the cooling filter rod through tipping paper to form a heated cigarette, and evaluating smoking results show that the baked aroma is obvious; and mixing the mixed sample solid with tobacco powder according to the weight ratio of 1: 500, preparing tobacco thin slices, wrapping the tobacco thin slices with cigarette paper to form tobacco sections, connecting the tobacco sections with a cooling filter tip through tipping paper to form a heated cigarette, and evaluating smoking results show that the tobacco is obvious in baking aroma and baked sweet aroma and full in aroma.
The application in the traditional cigarette is as follows: preparing the mixed sample into an ethanol solution, uniformly applying the ethanol solution on the surface of a tow (the weight ratio of the ethanol solution to the tow is 1:400), preparing a filter tip, wrapping tobacco shreds with cigarette paper to form a tobacco section, connecting the tobacco section and the filter tip through tipping paper to form a cigarette, and evaluating smoking results show that the roasted aroma and fragrance are obvious; preparing the mixed sample into an ethanol solution, uniformly applying the ethanol solution on the surface of the tobacco shreds (the weight ratio of the ethanol solution to the tobacco shreds is 1: 1000), wrapping the tobacco shreds with cigarette paper to form a tobacco section, connecting the tobacco section and a filter rod through tipping paper to form a cigarette, and evaluating smoking results show that the cigarette has obvious characteristic baking aroma and baking sweet aroma and has rich and full and harmonious aroma.
Example 2
Synthesis of alkaline maillard intermediates: mixing L-glycine and glucose according to the proportion of 1: 1 molar ratio, adding 4 times (the ratio of the total weight of the L-glycine and the glucose) of glycol solvent, adding 10 percent (the ratio of the total weight of the L-glycine and the glucose) of NaOH catalyst, and reacting for 6 hours at 130 ℃. Then adding 2.5 times (the ratio of the total weight of the L-glycine and the glucose) of deionized water for dissolving, adjusting the pH value to be neutral by using 1.0mol/L HCl solution, obtaining a Maillard reaction intermediate with the membrane molecular weight cut-off of 500-5000 by using the obtained Maillard crude product through a membrane separator dialysis method, and then freezing and drying to remove the solvent or water in the Maillard reaction intermediate, thereby obtaining the solid Maillard intermediate.
To the Maillard reaction intermediate obtained as above, 10 wt% of a solid acid (same as in example 1) was added and mixed uniformly. The cleavage experiments at 350 ℃ and 600 ℃ were carried out under the same conditions as in example 1. The cleavage product results are shown in table 2 below:
TABLE 2 results of Py-GC/MS of glucose-glycine Maillard reaction intermediates (basic method, molecular weight 500-
Table 2 shows Py-GC/MS results of glucose-glycine Maillard reaction intermediates (basic method, molecular weight 500-. It can be seen that the relative content of 5-hydroxymethylfurfural in the pyrolysis gas increases after the addition of the solid acid, whereas 5-hydroxymethylfurfural is a substance having a strong radical scavenging effect and an anti-oxidation effect, as is well known to those skilled in the art.
The effect of scavenging DPPH radicals was tested in the same manner as in example 1. As shown in FIG. 2, the removal rate of DPPH free radicals by the absorption solution of the pyrolysis gas is obviously improved after the solid acid is added during the pyrolysis at 300 ℃.
The application in heating cigarettes comprises the following steps: mixing the mixed sample solid with tobacco powder according to a mass ratio of 1: 600, preparing tobacco thin slices, wrapping the tobacco thin slices with cigarette paper to form tobacco sections, connecting the tobacco sections with a cooling filter rod through tipping paper to form a heated cigarette, and evaluating smoking results show that the tobacco thin slices are obvious in baking aroma and baked sweet aroma and full in aroma.
The application in the traditional cigarette is as follows: preparing the mixed sample into an ethanol solution, uniformly applying the ethanol solution on the surface of tobacco shreds (the mass ratio of the ethanol solution to the tobacco shreds is 1:800), wrapping the tobacco shreds with cigarette paper to form a tobacco section, connecting the tobacco section and a filter rod through tipping paper to form a cigarette, and evaluating smoking results show that the cigarette has obvious characteristic baking aroma and baking sweet aroma and has rich and full and harmonious aroma.
The preferred embodiments of the present invention have been described in detail, however, the present invention is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solution of the present invention within the technical idea of the present invention, and these simple modifications are within the protective scope of the present invention.
It should be noted that the various technical features described in the above embodiments can be combined in any suitable manner without contradiction, and the invention is not described in any way for the possible combinations in order to avoid unnecessary repetition.
In addition, any combination of the various embodiments of the present invention is also possible, and the same should be considered as the disclosure of the present invention as long as it does not depart from the spirit of the present invention.
Claims (11)
1. A composition capable of reducing the free radical content of cigarette smoke, wherein the composition comprises a solid acid and a maillard reaction intermediate, wherein the weight ratio of the solid acid to the maillard reaction intermediate is 1: 5-1: 1000.
2. the composition according to claim 1, wherein the solid acid is an oxide-based solid acid or a metal salt-based solid acid.
3. The composition according to claim 2, wherein the oxide-based solid acid is selected from Al-based2O3-SiO2Mixed oxides based on Al2O3-B2O3Mixed oxides and based on ZrO2-MoO3One or more of the mixed oxides of (a).
4. The composition according to claim 2, wherein the metal salt solid acid is selected from one or more of metal sulfate and metal phosphate.
5. The composition as claimed in claim 1, wherein the Maillard reaction intermediate is obtained by Maillard reaction of amino acid and saccharide at 50-200 deg.C.
6. The composition of claim 5, wherein the amino acid is selected from at least one of glycine, alanine, arginine, glutamic acid, leucine, and isoleucine.
7. The composition of claim 5, wherein the saccharide is selected from at least one of glucose, fructose, sucrose, lactose, mannose and galactose.
8. A method of making the composition of any one of claims 1-7, comprising: contacting the solid acid with the Maillard reaction intermediate.
9. The process of claim 8, wherein the contacting is by triturating and mixing a solid acid and a solid maillard reaction intermediate; and/or by immersing the solid acid in a Maillard reaction intermediate solution.
10. A method of reducing the free radical content of cigarette smoke comprising: the addition of a composition according to any one of claims 1-9 to the tobacco formulation of said cigarette results in a reduction of the free radical content in the smoke produced by said cigarette in use.
11. A cigarette using a tobacco formulation comprising a composition according to any one of claims 1 to 9.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6048404A (en) * | 1998-05-07 | 2000-04-11 | R.J. Reynolds Tobacco Company | Tobacco flavoring components of enhanced aromatic content and method of providing same |
| CN101397313A (en) * | 2007-09-27 | 2009-04-01 | 武汉烟草(集团)有限公司 | Maillard reaction intermediate, preparation method and use thereof |
| WO2009081214A1 (en) * | 2007-12-20 | 2009-07-02 | Szoelloesi Peter | Specific, highly effective cigarette filter |
| CN101704850A (en) * | 2009-10-21 | 2010-05-12 | 安徽中烟工业公司 | Method for separating and extracting compound of Amadori of Maillard reaction midbody |
| CN102766119A (en) * | 2012-08-14 | 2012-11-07 | 中国科学技术大学 | Method for preparing 5-methylfurfural |
| CN104194938A (en) * | 2014-09-15 | 2014-12-10 | 中国烟草总公司郑州烟草研究院 | Preparation method of maillard reaction flavor for cigarette |
| CN106520368A (en) * | 2016-11-18 | 2017-03-22 | 湖北中烟工业有限责任公司 | Formula of Amadori reactive flavor, preparation method of Amadori reactive flavor and use of Amadori reactive flavor |
| CN107692299A (en) * | 2017-10-31 | 2018-02-16 | 浙江中烟工业有限责任公司 | It is a kind of that there is the thermal response intermediate flavouring essence for tobacco and its preparation and application that baking is fragrant and nut is fragrant |
| CN108576923A (en) * | 2018-05-16 | 2018-09-28 | 中国烟草总公司郑州烟草研究院 | A kind of quick-fried pearl cigarette of bilayer response type |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11412775B2 (en) * | 2012-10-09 | 2022-08-16 | R.J. Reynolds Tobacco Company | Tobacco-derived composition |
| CN104017647A (en) * | 2014-06-13 | 2014-09-03 | 广西科技大学 | Method for preparing maillard reaction product of mango extract and application of product to cigarettes |
| CN104017648A (en) * | 2014-06-13 | 2014-09-03 | 广西科技大学 | Method for preparing maillard reaction product of longan extract and application of products to cigarettes |
| CN109222201B (en) * | 2018-09-07 | 2021-09-14 | 云南中烟工业有限责任公司 | Method for preparing baked fragrant reconstituted tobacco through targeted extraction |
| CN109259307B (en) * | 2018-09-13 | 2021-05-25 | 云南中烟工业有限责任公司 | Tobacco-baked fragrant type cigarette blasting bead capable of reducing free radicals of smoke and preparation method thereof |
| CN109259293B (en) * | 2018-09-13 | 2021-03-23 | 云南中烟工业有限责任公司 | Tea baking aroma reconstituted tobacco and preparation method and application thereof |
| CN109259308A (en) * | 2018-09-25 | 2019-01-25 | 云南中烟工业有限责任公司 | The coffee for reducing flue gas free-radical contents toasts cigarette with quick-fried pearl and preparation method thereof |
| CN111374341A (en) * | 2018-12-29 | 2020-07-07 | 贵州中烟工业有限责任公司 | Method for preparing Maillard reaction product by adopting red date extract, Maillard reaction product and application |
-
2020
- 2020-12-14 CN CN202011470797.3A patent/CN112545046A/en active Pending
-
2021
- 2021-04-26 WO PCT/CN2021/089834 patent/WO2022126958A1/en active Application Filing
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6048404A (en) * | 1998-05-07 | 2000-04-11 | R.J. Reynolds Tobacco Company | Tobacco flavoring components of enhanced aromatic content and method of providing same |
| CN101397313A (en) * | 2007-09-27 | 2009-04-01 | 武汉烟草(集团)有限公司 | Maillard reaction intermediate, preparation method and use thereof |
| WO2009081214A1 (en) * | 2007-12-20 | 2009-07-02 | Szoelloesi Peter | Specific, highly effective cigarette filter |
| CN101704850A (en) * | 2009-10-21 | 2010-05-12 | 安徽中烟工业公司 | Method for separating and extracting compound of Amadori of Maillard reaction midbody |
| CN102766119A (en) * | 2012-08-14 | 2012-11-07 | 中国科学技术大学 | Method for preparing 5-methylfurfural |
| CN104194938A (en) * | 2014-09-15 | 2014-12-10 | 中国烟草总公司郑州烟草研究院 | Preparation method of maillard reaction flavor for cigarette |
| CN106520368A (en) * | 2016-11-18 | 2017-03-22 | 湖北中烟工业有限责任公司 | Formula of Amadori reactive flavor, preparation method of Amadori reactive flavor and use of Amadori reactive flavor |
| CN107692299A (en) * | 2017-10-31 | 2018-02-16 | 浙江中烟工业有限责任公司 | It is a kind of that there is the thermal response intermediate flavouring essence for tobacco and its preparation and application that baking is fragrant and nut is fragrant |
| CN108576923A (en) * | 2018-05-16 | 2018-09-28 | 中国烟草总公司郑州烟草研究院 | A kind of quick-fried pearl cigarette of bilayer response type |
Non-Patent Citations (1)
| Title |
|---|
| 于洪全: "《功能材料》", 30 June 2014 * |
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