WO2022126958A1 - Composition capable of reducing free radical levels in cigarette smoke and preparation method therefor - Google Patents
Composition capable of reducing free radical levels in cigarette smoke and preparation method therefor Download PDFInfo
- Publication number
- WO2022126958A1 WO2022126958A1 PCT/CN2021/089834 CN2021089834W WO2022126958A1 WO 2022126958 A1 WO2022126958 A1 WO 2022126958A1 CN 2021089834 W CN2021089834 W CN 2021089834W WO 2022126958 A1 WO2022126958 A1 WO 2022126958A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- solid acid
- maillard reaction
- composition
- cigarette
- reaction intermediate
- Prior art date
Links
- 235000019504 cigarettes Nutrition 0.000 title claims abstract description 82
- 239000000203 mixture Substances 0.000 title claims abstract description 59
- 150000003254 radicals Chemical class 0.000 title claims abstract description 36
- 239000000779 smoke Substances 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title abstract description 7
- 239000011973 solid acid Substances 0.000 claims abstract description 61
- 239000007806 chemical reaction intermediate Substances 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 29
- 241000208125 Nicotiana Species 0.000 claims description 65
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 229940024606 amino acid Drugs 0.000 claims description 12
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- 150000001413 amino acids Chemical class 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 10
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 10
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- 239000007787 solid Substances 0.000 claims description 10
- 150000001720 carbohydrates Chemical class 0.000 claims description 8
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- 239000000126 substance Substances 0.000 claims description 8
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- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 6
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- 238000002156 mixing Methods 0.000 claims description 6
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- 238000009472 formulation Methods 0.000 claims description 4
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- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 3
- 239000004475 Arginine Substances 0.000 claims description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 3
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- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 3
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 3
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 3
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- 235000009697 arginine Nutrition 0.000 claims description 3
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- 239000004220 glutamic acid Substances 0.000 claims description 3
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- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims 2
- 238000000197 pyrolysis Methods 0.000 abstract description 14
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- 239000013543 active substance Substances 0.000 abstract description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
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- VOLMSPGWNYJHQQ-UHFFFAOYSA-N 3,5-dihydroxy-6-methyl-2,3-dihydropyran-4-one Chemical compound CC1=C(O)C(=O)C(O)CO1 VOLMSPGWNYJHQQ-UHFFFAOYSA-N 0.000 description 4
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- MGJZITXUQXWAKY-UHFFFAOYSA-N diphenyl-(2,4,6-trinitrophenyl)iminoazanium Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1N=[N+](C=1C=CC=CC=1)C1=CC=CC=C1 MGJZITXUQXWAKY-UHFFFAOYSA-N 0.000 description 4
- HHEAADYXPMHMCT-UHFFFAOYSA-N dpph Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1[N]N(C=1C=CC=CC=1)C1=CC=CC=C1 HHEAADYXPMHMCT-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 230000007760 free radical scavenging Effects 0.000 description 4
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- 230000008569 process Effects 0.000 description 4
- 238000000045 pyrolysis gas chromatography Methods 0.000 description 4
- BCWAYSFBQDPDIG-BTVCFUMJSA-N 2-aminoacetic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound NCC(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O BCWAYSFBQDPDIG-BTVCFUMJSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
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- 235000000346 sugar Nutrition 0.000 description 3
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- NQVYSWKKOWIMDD-LGDQNDJISA-N (2s)-2-aminopropanoic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound C[C@H](N)C(O)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O NQVYSWKKOWIMDD-LGDQNDJISA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
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- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 2
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
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- 230000002292 Radical scavenging effect Effects 0.000 description 2
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- 238000003786 synthesis reaction Methods 0.000 description 2
- OCZVHBZNPVABKX-UHFFFAOYSA-N 1,1-diphenyl-2-(2,4,6-trinitrophenyl)hydrazine;ethanol Chemical compound CCO.[O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1NN(C=1C=CC=CC=1)C1=CC=CC=C1 OCZVHBZNPVABKX-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical group C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- 108010005094 Advanced Glycation End Products Proteins 0.000 description 1
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- 230000005526 G1 to G0 transition Effects 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B3/00—Preparing tobacco in the factory
- A24B3/12—Steaming, curing, or flavouring tobacco
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D1/00—Cigars; Cigarettes
- A24D1/002—Cigars; Cigarettes with additives, e.g. for flavouring
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D1/00—Cigars; Cigarettes
- A24D1/04—Cigars; Cigarettes with mouthpieces or filter-tips
- A24D1/042—Cigars; Cigarettes with mouthpieces or filter-tips with mouthpieces
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D1/00—Cigars; Cigarettes
- A24D1/20—Cigarettes specially adapted for simulated smoking devices
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/04—Tobacco smoke filters characterised by their shape or structure
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/06—Use of materials for tobacco smoke filters
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
- A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
- A24D3/17—Filters specially adapted for simulated smoking devices
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
Definitions
- the invention belongs to the field of cigarettes, and more particularly, relates to a composition capable of reducing the content of free radicals in cigarette smoke, a preparation method thereof, and a method for reducing the content of free radicals in cigarette smoke by using the composition.
- the Maillard reaction is an important method for the preparation of heat-reactive flavors.
- the final product of the complete Maillard reaction has a rich flavor, but these flavors volatilize quickly, are not persistent, and are easily lost during processing and storage.
- Maillard reaction intermediates are intermediates of Maillard reactions, which are mixtures produced by non-enzymatic browning of sugars and amino acids when heated. The components in the mixture are very complex. Depending on the degree of browning, there are both small molecular ⁇ -diketones, esters, and heterocyclic derivatives with complex structures (mainly furan and pyran rings), as well as high molecular weight. the browning product.
- Maillard reaction intermediates are the precursors of important aroma components, which generally do not have aromas themselves, but can be converted and cracked into various final product components of Maillard reactions under heating conditions. The type of aroma released is related to the sugars and amino acids used. Maillard reaction intermediates prepared from different types of sugars and amino acids have different aromas. Fragrance differences are also related to the degree of Maillard reaction progress. The longer the reaction time, the more thorough the Maillard reaction, and the different types of fragrance.
- Active free radicals In daily life, active free radicals are generated in many occasions. Active free radicals attack biological substances in the human body, including unsaturated fatty acids, proteins, amino acids and DNA, etc., which change the fluidity of cell membranes and the conformation of membrane proteins, directly or indirectly promote the occurrence of various diseases and endanger health. Free radicals in cigarette smoke are potentially harmful. Flue gas free radicals include solid-phase free radicals and gas-phase free radicals. Solid-phase free radicals have good stability and long life. The main components are quinone and semiquinone free radicals and some polycyclic aromatic hydrocarbon free radicals, carbon and phosphorus free radicals. Base et al. Gas-phase free radicals are mainly composed of alkyl radicals and alkoxy radicals, and have high chemical reactivity. Although they have a short lifespan, they can still penetrate the Cambridge filter, which is potentially harmful.
- Maillard reactants and Maillard reaction intermediates are often used as flavoring agents for cigarettes, but their capture and annihilation effects on free radicals in smoke have not been reported.
- the purpose of the present invention is to reduce the content of free radicals in cigarette smoke.
- the inventor provides a composition capable of reducing the content of free radicals in cigarette smoke, wherein solid acid is used to catalyze the Maillard reaction intermediate
- the pyrolysis of the Maillard reaction intermediate can release more antioxidant active substances (which can effectively reduce the free radical content) at a lower temperature while the Maillard reaction intermediate is flavored, which is beneficial to reducing the free radical content in the flue gas. have a certain promotion effect.
- the present invention provides a composition capable of reducing the content of free radicals in cigarette smoke, characterized in that the composition comprises a solid acid and a Maillard reaction intermediate, wherein the solid acid and Maillard The weight ratio of German reaction intermediates is 1:5-1:1000.
- the solid acid is an oxide-based solid acid or a metal salt-based solid acid.
- the oxide-based solid acid is selected from the group consisting of Al2O3-SiO2-based mixed oxides, Al2O3-B2O3-based mixed oxides, and ZrO2-MoO3-based mixed oxides one or more of the mixed oxides.
- the metal salt solid acid is selected from one or more of metal sulfates and metal phosphates.
- the Maillard reaction intermediate is obtained by performing Maillard reaction between amino acids and carbohydrates at a temperature of 50-200°C.
- the amino acid is selected from at least one of glycine, alanine, arginine, glutamic acid, leucine and isoleucine.
- the carbohydrate substance is selected from at least one of glucose, fructose, sucrose, lactose, mannose and galactose.
- the present invention also provides a method for preparing the above-mentioned composition, the method comprising: contacting the solid acid and the Maillard reaction intermediate.
- the contacting is performed by grinding and mixing the solid acid and the solid Maillard reaction intermediate; and/or by immersing the solid acid in the Maillard reaction intermediate solution.
- the present invention also provides a method for reducing the content of free radicals in cigarette smoke, comprising: adding the above-mentioned composition to the tobacco preparation of the cigarette, so that the cigarette generates The free radical content in the flue gas is reduced.
- the present invention also provides a cigarette, the tobacco formulation used in the cigarette comprises the above-mentioned composition.
- the present invention has at least the following beneficial technical effects:
- the solid acid is used as a catalyst to effectively thermally decompose the Maillard reaction intermediate to release aroma, and simultaneously reduce the release of cigarette smoke to a certain extent.
- the composition of the present invention capable of reducing the content of free radicals in cigarette smoke can be applied to both traditional cigarettes and heated cigarettes; (3) the solid acid is cheap , easy to obtain, high safety; and (4) the composition of the present invention capable of reducing the content of free radicals in cigarette smoke can be obtained by simply contacting the solid acid and the Maillard intermediate reactant, such as mixing or solution adsorption , the process is simple but the effect is good.
- Figure 1 shows the DPPH radical scavenging rate of solid acid and alanine-gluconic acid Maillard reaction intermediate cracked gas absorption liquid (300°C) in Example 1;
- FIG. 2 shows the DPPH radical scavenging rate of solid acid and glycine-glucose basic Maillard reaction intermediate cracked gas absorption liquid (300° C.) in Example 2.
- the present invention provides a composition capable of reducing the content of free radicals in cigarette smoke, characterized in that the composition comprises a solid acid and a Maillard reaction intermediate, wherein the solid acid and Maillard reaction are The weight ratio of the intermediate is 1:5-1:1000.
- the weight ratio of the solid acid and the Maillard reaction intermediate in the composition can be further selected in the range of 1:5-1:1000, for example, the weight of the solid acid and the Maillard reaction intermediate
- the ratio may be 1:10, 1:20, 1:50, 1:100, 1:200, or 1:500, etc., but is not limited thereto.
- the composition may consist solely of the solid acid and the Maillard reaction intermediate.
- the type of solid acid is not particularly limited, and it can be a common type of solid acid.
- the solid acid may be a solid acid such as oxides, sulfides, metal salts, or heteropolyacids.
- the solid acid may be an oxide-based solid acid or a metal salt-based solid acid.
- the oxide-based solid acid may be selected from Al2O3-SiO2-based mixed oxides, Al2O3-B2O3-based mixed oxides, and ZrO2-MoO3-based oxides One or more of these;
- the metal salt solid acid can be selected from one or more of metal sulfates and metal phosphates.
- the metal in the metal salt can be, for example, Fe, Al, Cu, or the like.
- the solid acid used in the present invention can be more specifically aNa2O:bAl2O3:cSiO2, where a ⁇ 0.1%, b/c ⁇ 1/25 (or for example 1/10-1/30 etc.), generally can be fired from alumina and silicon oxide in a certain molar ratio, in which sodium oxide is an impurity, so control its content is not high.
- the term “Maillard reaction”, also known as non-enzymatic browning reaction, is a kind of non-enzymatic browning widely existing in the food industry. ), after a complicated process, a brown or even black macromolecular substance like melanin or pseudomelanin is finally formed, so it is also called carbonylamine reaction; and the term “Maillard reaction intermediate” refers to the reaction in Maillard. It is an intermediate product in the German reaction process, and can be obtained from the incomplete Maillard reaction of raw materials at a certain temperature.
- the Maillard reaction intermediate can be composed of amino acids and carbohydrates (the molar ratio of the two can be 1:0.5-2, preferably 1:1) between 50- It is obtained by carrying out Maillard reaction under the conditions of 200°C (for example, 80°C, 100°C, 120°C, 150°C or 180°C, etc.).
- the Maillard reaction can be carried out by a method well known to those skilled in the art, for example, it can be carried out by an alkaline method, that is, an alkaline catalyst is used to catalyze the above reaction, and an acidic reagent is added at the end of the reaction to adjust the pH to medium or can be carried out by an acidic method, that is, an acidic catalyst is used to catalyze the above reaction, and an alkaline reagent is added at the end of the reaction to adjust the pH to neutrality.
- an alkaline method that is, an alkaline catalyst is used to catalyze the above reaction
- an acidic reagent is added at the end of the reaction to adjust the pH to neutrality.
- the amino acid can be selected from at least one of glycine, alanine, arginine, glutamic acid, leucine and isoleucine;
- the carbohydrate substance may be selected from at least one of glucose, fructose, sucrose, lactose, mannose and galactose.
- the present invention also provides a method for preparing the above-mentioned composition, the method comprising: contacting the solid acid and the Maillard reaction intermediate.
- the contact of the solid acid and the Maillard reaction intermediate can be carried out in any manner, for example, they can be mixed in a solid phase, a liquid phase or a combination thereof.
- the contacting may be performed by grinding and mixing the solid acid and the solid Maillard reaction intermediate; and/or may be performed by immersing the solid acid in the Maillard reaction intermediate solution.
- the mixing ratio of the solid acid and the solid Maillard reaction intermediate can be 1:5-1:1000 ( weight ratio).
- the Maillard reaction intermediate solution may be a Maillard reaction intermediate solution at a concentration of 5-70% by weight. water, ethanol, propylene glycol, glycerol solution or a combination thereof of the intermediate, and the contacting may further include low temperature baking or air drying after the solid acid is immersed in the solution for 2-24 hours.
- the present invention also provides a method for reducing the content of free radicals in cigarette smoke, comprising: adding the above-mentioned composition to the tobacco preparation of the cigarette, so that the cigarette generates The free radical content in the flue gas is reduced.
- the present invention also provides a cigarette, the tobacco formulation used in the cigarette comprises the above-mentioned composition.
- composition of the present invention According to the above-mentioned various methods for preparing the composition of the present invention, correspondingly different methods can also be adopted in the process of using the composition of the present invention to reduce the content of free radicals in cigarette smoke or to prepare cigarettes.
- the solid composition of the present invention can be uniformly mixed with tobacco powder to prepare shredded tobacco sheet, cigarette paper wraps the shredded tobacco to form a tobacco segment, and the tobacco segment and the cooling tip rod pass through tipping paper connected to form low-temperature cigarette cigarettes;
- the composition of the present invention can be formulated into water, ethanol, propylene glycol, glycerin solution or a combination thereof, and then evenly mixed with tobacco powder to prepare shredded tobacco sheet, and cigarette paper wraps the shredded tobacco to form Tobacco segment, the tobacco segment and the cooling tip rod are connected by tipping paper to form a low-temperature cigarette;
- the composition of the present invention is prepared into water, ethanol, propylene glycol, glycerin solution or a combination thereof, and uniformly applied to the surface of the tobacco sheet , the cigarette paper wraps the tobacco shreds to form tobacco segments, and the tobacco segments and the cooling tip rod are connected by tipping paper to form low-temperature cigarette cigarettes;
- the composition of the present invention can be formulated into a solution of water or ethanol or propylene glycol or glycerol, which is uniformly applied to the surface of the cut tobacco, and the cut tobacco is wrapped with cigarette paper to form a tobacco segment, and the tobacco segment is combined with the tobacco segment.
- the mouth sticks are connected by tipping paper to form cigarette cigarettes;
- the composition of the present invention is prepared into a solution of water or ethanol or propylene glycol or glycerol, and is uniformly applied to the surface of the cigarette paper, and the cigarette paper wraps the shredded tobacco to form a tobacco segment, and the tobacco segment It is connected with the tip stick through tipping paper to form a cigarette;
- the composition of the present invention is formulated into a solution of water or ethanol or propylene glycol or glycerol, which is uniformly applied on the surface of the tow to prepare a tip stick, and the cigarette paper wraps the shredded tobacco to form Tobacco segment, the tobacco segment and the mouth stick are connected by tipping paper to form cigarette cigarettes;
- the solid composition of the present invention is uniformly applied to the tow to prepare the mouth stick, the cigarette paper wraps the cut tobacco to form the tobacco segment, the tobacco segment and the mouth stick Connected by tipping paper to form cigarettes.
- the inventors have found through research that, in the composition of the present invention, the solid acid can catalyze the pyrolysis of the Maillard reaction intermediate. or 300 °C), more antioxidant active substances are released, which has a certain promoting effect on reducing the content of free radicals in the flue gas.
- the pure Maillard reaction intermediate and the Maillard reaction intermediate + 10% solid acid were subjected to thermal cracking experiments with cracking temperatures of 200°C, 300°C and 400°C, respectively.
- the pyrolysis atmosphere is helium gas, the gas flow rate: 70 mL/min, the temperature of the valve box of the pyrolysis apparatus: 280 °C, and the temperature of the transmission line of the pyrolysis apparatus: 280 °C.
- GC-MS method elastic quartz capillary column; stationary phase is 5% phenyl-95% methyl polysiloxane; specification is [30m (length) ⁇ 0.25 mm (inner diameter) ⁇ 0.25 ⁇ m (film thickness)]; Air flow, 1.0mL/min; split ratio, 100:1; heating program, initial temperature 40°C, hold for 3min, rise to 240°C at a rate of 10°C/min, and then rise to 280°C at a rate of 20°C/min , maintained for 15min; mass spectrometry transmission line temperature 280 °C; ion source temperature 230 °C; quadrupole temperature 150 °C; mass scanning range 29-450amu.
- Table 1 The results of the cleavage products are shown in Table 1 below:
- Table 1 shows the Py-GC/MS results of the glucose-alanine Maillard reaction intermediate (acid method, molecular weight 500-5000 kDa) under air atmosphere. It can be seen that after the addition of solid acid, the relative content of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one in the cracked gas increases, and as shown in the art It is well known to persons that 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one is a substance with strong free radical scavenging effect and antioxidant effect.
- the mixed samples were cracked at 300°C in a tube furnace, the cracking gas was carried in an Ar atmosphere, and absorbed with anhydrous ethanol, and the cracking time was 10 min.
- the sample solution without the addition of the sample solution is blank, and the treatment without the composition of the present invention is the control.
- measure the absorbance at a wavelength of 517 nm and use the following formula to calculate the DPPH free radical scavenging rate:
- A0 is the absorbance of the DPPH solution without adding the composition of the present invention
- Ai is the absorbance of the DPPH solution after adding the composition of the present invention
- Aj is the absorbance of the composition of the present invention, wherein the larger the DPPH free radical scavenging rate is The stronger the antioxidant capacity.
- the mixed sample is prepared into an ethanol solution, which is uniformly applied to the surface of the tow (the weight ratio to the tow is 1:400) to prepare a mouthpiece, and the shredded tobacco is wrapped with cigarette paper to form a tobacco segment. It is connected with the tip stick through tipping paper to form a cigarette, and the evaluation results show that the roasted aroma is obvious;
- the mixed sample is prepared into an ethanol solution, which is evenly applied to the surface of the cut tobacco (the weight ratio to the cut tobacco is 1:1000 ), the cigarette paper wraps the cut tobacco to form the tobacco segment, and the tobacco segment and the mouth stick are connected by tipping paper to form the cigarette.
- Synthesis of basic famaillard intermediate mix L-glycine and glucose in a 1:1 molar ratio, add 4 times the amount of ethylene glycol solvent (ratio to the total weight of L-glycine and glucose), and add 10% (ratio to the total weight of L-glycine and glucose) NaOH catalyst, reacted at 130°C for 6 hours. Then add 2.5 times the amount (the ratio to the total weight of L-glycine and glucose) in deionized water to dissolve, and then adjust the pH to neutrality with 1.0mol/L HCl solution, and the obtained crude Maillard product passes through the membrane separator.
- a Maillard reaction intermediate with a membrane molecular weight cut-off of 500-5000 is obtained by dialysis, and then freeze-dried to remove the solvent or moisture therein, thereby obtaining a solid Maillard intermediate.
- Table 2 shows the Py-GC/MS results of the glucose-glycine Maillard reaction intermediate (basic method, molecular weight 500-5000 kDa) under air atmosphere. It can be seen that after adding the solid acid, the relative content of 5-Hydroxymethylfurfural in the cracked gas increases, and as is well known to those skilled in the art, 5-Hydroxymethylfurfural has strong free radical scavenging effect and resistance to oxidizing substances.
- the mixed sample solids and tobacco powder are uniformly mixed according to the mass ratio of 1:600 to prepare shredded tobacco sheets, cigarette paper wraps the shredded tobacco sheets to form tobacco segments, and the tobacco segments and cooling nozzle rods pass through tipping
- the paper is connected to form a heated cigarette, and the smoking evaluation results show that the aroma of roasted and roasted sweet is obvious and the aroma is full.
- the mixed sample is prepared into an ethanol solution, which is uniformly applied to the surface of the cut tobacco (the ratio to the mass of the cut tobacco is 1:800).
- the paper is connected to form a cigarette, and the evaluation results show that the characteristic roasted aroma and roasted sweet aroma are obvious, and the aroma is rich, full and harmonious.
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Abstract
A composition capable of reducing free radical levels in cigarette smoke and a preparation method therefor. The composition contains a solid acid and a Maillard reaction intermediate, the weight ratio of the solid acid to the Maillard reaction intermediate being 1:5-1:1000. Also provided are a method for using the composition to reduce free radical levels in cigarette smoke, and a cigarette produced using the composition. In the composition, the solid acid can catalyze the pyrolysis of the Maillard reaction intermediate, thereby releasing more antioxidant active substances at a low temperature while producing pleasant scent by the Maillard reaction intermediate, and facilitating reduction of the free radical levels in smoke.
Description
本发明属于卷烟领域，更具体地，涉及一种能够降低卷烟烟气中自由基含量的组合物及其制备方法，以及使用该组合物降低卷烟烟气中自由基含量的方法。The invention belongs to the field of cigarettes, and more particularly, relates to a composition capable of reducing the content of free radicals in cigarette smoke, a preparation method thereof, and a method for reducing the content of free radicals in cigarette smoke by using the composition.
美拉德反应是热反应类香料制备的重要手段，完整的美拉德反应终产物风味浓郁，但是这些香味挥发快、不持久、加工和储存过程中很容易散失。美拉德反应中间体是美拉德反应的中间产物，是由如糖类和氨基酸在受热时发生非酶棕化产生的混合物。混合物内含成分非常复杂，根据棕色化程度的不同，既有小分子的α-双酮，酯类，也有结构复杂的杂环衍生物(主要为呋喃环和吡喃环)，还包括高分子量的褐化产物。美拉德反应中间体是重要的致香成分的前体物，其本身一般不具备香气，但是在受热条件下能够转化和裂解成多种美拉德反应的终产物成分。释放的香味类型和所用的糖和氨基酸相关。不同类型的糖和氨基酸制备的美拉德反应中间体，香味有差异。香味差异也和美拉德反应进行程度有关。反应时间越长，美拉德反应进行越彻底，香味类型也不一样。The Maillard reaction is an important method for the preparation of heat-reactive flavors. The final product of the complete Maillard reaction has a rich flavor, but these flavors volatilize quickly, are not persistent, and are easily lost during processing and storage. Maillard reaction intermediates are intermediates of Maillard reactions, which are mixtures produced by non-enzymatic browning of sugars and amino acids when heated. The components in the mixture are very complex. Depending on the degree of browning, there are both small molecular α-diketones, esters, and heterocyclic derivatives with complex structures (mainly furan and pyran rings), as well as high molecular weight. the browning product. Maillard reaction intermediates are the precursors of important aroma components, which generally do not have aromas themselves, but can be converted and cracked into various final product components of Maillard reactions under heating conditions. The type of aroma released is related to the sugars and amino acids used. Maillard reaction intermediates prepared from different types of sugars and amino acids have different aromas. Fragrance differences are also related to the degree of Maillard reaction progress. The longer the reaction time, the more thorough the Maillard reaction, and the different types of fragrance.
在日常生活中，很多场合会产生活性自由基。活性自由基攻击人体内的生物物质，包括不饱和脂肪酸、蛋白质、氨基酸和DNA等，使细胞膜的流动性和膜蛋白的构象发生变化，直接或间接促进各种疾病的发生，危害健康。卷烟产生的烟气中的自由基具有潜在的危害性。烟气自由基包括固相自由基和气相自由基两种，固相自由基稳定性好，寿命较长，主要成分为醌和半醌类自由基及部分多环芳烃自由基、碳和磷自由基等。气相自由基主要由烷基自由基和烷氧基自由基组成，化学反应活性高，虽然寿命较短，但还是能够穿透剑桥滤片，具有潜在的危害性。In daily life, active free radicals are generated in many occasions. Active free radicals attack biological substances in the human body, including unsaturated fatty acids, proteins, amino acids and DNA, etc., which change the fluidity of cell membranes and the conformation of membrane proteins, directly or indirectly promote the occurrence of various diseases and endanger health. Free radicals in cigarette smoke are potentially harmful. Flue gas free radicals include solid-phase free radicals and gas-phase free radicals. Solid-phase free radicals have good stability and long life. The main components are quinone and semiquinone free radicals and some polycyclic aromatic hydrocarbon free radicals, carbon and phosphorus free radicals. Base et al. Gas-phase free radicals are mainly composed of alkyl radicals and alkoxy radicals, and have high chemical reactivity. Although they have a short lifespan, they can still penetrate the Cambridge filter, which is potentially harmful.
美拉德反应物和美拉德反应中间体常用作卷烟的致香剂，但其对烟气中自由基的捕捉湮灭效应，还未见报道。Maillard reactants and Maillard reaction intermediates are often used as flavoring agents for cigarettes, but their capture and annihilation effects on free radicals in smoke have not been reported.
本发明的目的在于降低卷烟烟气中的自由基含量，本发明人为此目的，提供了一种能够降低卷烟烟气中自由基含量的组合物，其中采用固体酸来催化美拉德反应中间体的热解，在美拉德反应中间体增香的同时，可以在较低温度下，释放较多的抗氧化活性物质(其可有效降低自由基含量)，对降低烟气中的自由基含量具有一定的促进作用。The purpose of the present invention is to reduce the content of free radicals in cigarette smoke. For this purpose, the inventor provides a composition capable of reducing the content of free radicals in cigarette smoke, wherein solid acid is used to catalyze the Maillard reaction intermediate The pyrolysis of the Maillard reaction intermediate can release more antioxidant active substances (which can effectively reduce the free radical content) at a lower temperature while the Maillard reaction intermediate is flavored, which is beneficial to reducing the free radical content in the flue gas. have a certain promotion effect.
因此，在一方面，本发明提供了一种能够降低卷烟烟气中自由基含量的组合物，其特征在于，所述组合物包含固体酸和美拉德反应中间体，其中所述固体酸和美拉德反应中间体的重量比为1：5-1：1000。Therefore, in one aspect, the present invention provides a composition capable of reducing the content of free radicals in cigarette smoke, characterized in that the composition comprises a solid acid and a Maillard reaction intermediate, wherein the solid acid and Maillard The weight ratio of German reaction intermediates is 1:5-1:1000.
在本发明的一个实施方式中，所述固体酸为氧化物类固体酸或金属盐类固体酸。In one embodiment of the present invention, the solid acid is an oxide-based solid acid or a metal salt-based solid acid.
在本发明的一个实施方式中，所述氧化物类固体酸选自基于Al 2O 3-SiO 2的混合氧化物、基于Al 2O 3-B 2O 3的混合氧化物和基于ZrO 2-MoO 3的混合氧化物中的一种或多种。In one embodiment of the present invention, the oxide-based solid acid is selected from the group consisting of Al2O3-SiO2-based mixed oxides, Al2O3-B2O3-based mixed oxides, and ZrO2-MoO3-based mixed oxides one or more of the mixed oxides.
在本发明的一个实施方式中，所述金属盐类固体酸选自金属硫酸盐和金属磷酸盐中的一种或多种。In one embodiment of the present invention, the metal salt solid acid is selected from one or more of metal sulfates and metal phosphates.
在本发明的一个实施方式中，所述美拉德反应中间体由氨基酸和糖类物质在50-200℃的条件下进行美拉德反应得到。In one embodiment of the present invention, the Maillard reaction intermediate is obtained by performing Maillard reaction between amino acids and carbohydrates at a temperature of 50-200°C.
在本发明的一个实施方式中，所述氨基酸选自甘氨酸、丙氨酸、精氨酸、谷氨酸、亮氨酸和异亮氨酸中的至少一种。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.
在本发明的一个实施方式中，所述糖类物质选自葡萄糖、果糖、蔗糖、乳糖、甘露糖和半乳糖中的至少一种。In one embodiment of the present invention, the carbohydrate substance is selected from at least one of glucose, fructose, sucrose, lactose, mannose and galactose.
另一方面，本发明还提供了一种制备如上所述的组合物的方法，所述方法包括：将所述固体酸和所述美拉德反应中间体接触。In another aspect, the present invention also provides a method for preparing the above-mentioned composition, the method comprising: contacting the solid acid and the Maillard reaction intermediate.
在本发明的一个实施方式中，所述接触通过将固体酸和固态美拉德反应中间体研磨混合；和/或通过将固体酸浸渍在美拉德反应中间体溶液中来进行。In one embodiment of the present invention, the contacting is performed by grinding and mixing the solid acid and the solid Maillard reaction intermediate; and/or by immersing the solid acid in the Maillard reaction intermediate solution.
另一方面，本发明还提供了一种降低卷烟烟气中自由基含量的方法，其包括：在所述卷烟的烟草制剂中加入如上所述的组合物，使得所述卷烟在使用时所产生的烟气中的自由基含量降低。In another aspect, the present invention also provides a method for reducing the content of free radicals in cigarette smoke, comprising: adding the above-mentioned composition to the tobacco preparation of the cigarette, so that the cigarette generates The free radical content in the flue gas is reduced.
另一方面，本发明还提供了一种卷烟，其所使用的烟草制剂中包含如上所述的组合物。In another aspect, the present invention also provides a cigarette, the tobacco formulation used in the cigarette comprises the above-mentioned composition.
与现有技术相比，本发明至少具有以下的有益技术效果：Compared with the prior art, the present invention has at least the following beneficial technical effects:
(1)在本发明的能够降低卷烟烟气中自由基含量的组合物中，固体酸作为催化剂，使美拉德反应中间体有效的热分解释放出香气，同时一定程度上降低卷烟烟气释放物中的自由基，具有减害作用；(2)本发明的能够降低卷烟烟气中自由基含量的组合物既可以应用于传统卷烟，也可以应用于加热卷烟；(3)固体酸价格便宜，易于得到，安全性高；以及(4)本发明的能够降低卷烟烟气中自由基含量的组合物可以通过仅将固体酸和美拉德中间反应体进行简单的接触如混合或者溶液吸附而得到，工艺简单但效果好。(1) In the composition of the present invention capable of reducing the content of free radicals in cigarette smoke, the solid acid is used as a catalyst to effectively thermally decompose the Maillard reaction intermediate to release aroma, and simultaneously reduce the release of cigarette smoke to a certain extent. (2) the composition of the present invention capable of reducing the content of free radicals in cigarette smoke can be applied to both traditional cigarettes and heated cigarettes; (3) the solid acid is cheap , easy to obtain, high safety; and (4) the composition of the present invention capable of reducing the content of free radicals in cigarette smoke can be obtained by simply contacting the solid acid and the Maillard intermediate reactant, such as mixing or solution adsorption , the process is simple but the effect is good.
附图是用来提供对本发明的进一步理解，并且构成说明书的一部分，与下面的具体实施方式一起用于解释本发明，但并不构成对本发明的限制。在附图中：The accompanying drawings are used to provide a further understanding of the present invention, and constitute a part of the specification, and together with the following specific embodiments, are used to explain the present invention, but do not constitute a limitation to the present invention. In the attached image:
图1示出了实施例1中固体酸和丙氨酸-葡萄糖酸式美拉德反应中间体裂解气吸收液(300℃)的DPPH自由基清除率；并且Figure 1 shows the DPPH radical scavenging rate of solid acid and alanine-gluconic acid Maillard reaction intermediate cracked gas absorption liquid (300°C) in Example 1; and
图2示出了实施例2中固体酸和甘氨酸-葡萄糖碱式美拉德反应中间体裂解气吸收液(300℃)的DPPH自由基清除率。FIG. 2 shows the DPPH radical scavenging rate of solid acid and glycine-glucose basic Maillard reaction intermediate cracked gas absorption liquid (300° C.) in Example 2. FIG.
以下对本发明的具体实施方式进行详细说明。应当理解的是，此处所描述的具体实施方式仅用于说明和解释本发明，并不用于限制本发明。Specific embodiments of the present invention will be described in detail below. It should be understood that the specific embodiments described herein are only used to illustrate and explain the present invention, but not to limit the present invention.
在本文中所披露的范围的端点和任何值都不限于该精确的范围或值，这些范围或值应当理解为包含接近这些范围或值的值。对于数值范围来说，各个范围的端点值之间、各个范围的端点值和单独的点值之间，以及单独的点值之间可以彼此组合而得到一个或多个新的数值范围，这些数值范围应被视为在本文中具体公开。The endpoints of ranges and any values disclosed herein are not limited to the precise ranges or values, which are to be understood to encompass values proximate to those ranges or values. For ranges of values, the endpoints of each range, the endpoints of each range and the individual point values, and the individual point values can be combined with each other to yield one or more new ranges of values that Ranges should be considered as specifically disclosed herein.
在详细描述本发明前，应了解，在此使用的术语只在于描述特定的实施方式，而不希望限制本发明的范围，本发明的范围仅由所附权利要求书限定。为了更完全地了解在此描述的本发明，采用以下术语，它们的定义如下所示。除非另外定义，在此使用的所有技术和科学术语具有与本发明所属领域的普通技术人员所理解的相同的含义。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 invention, which is defined solely by the appended claims. For a more complete understanding of the invention described herein, the following terms are employed, the definitions of which are shown below. Unless otherwise defined, all technical and scientific terms used herein have the same meaning as understood by one of ordinary skill in the art to which this invention belongs.
在一方面，本发明提供了一种能够降低卷烟烟气中自由基含量的组合物，其特征在于，所述组合物包含固体酸和美拉德反应中间体，其中所述固体酸和美拉德反应中间体的重量比为1：5-1：1000。In one aspect, the present invention provides a composition capable of reducing the content of free radicals in cigarette smoke, characterized in that the composition comprises a solid acid and a Maillard reaction intermediate, wherein the solid acid and Maillard reaction are The weight ratio of the intermediate is 1:5-1:1000.
根据本发明，所述组合物中的固体酸和美拉德反应中间体的重量比可以在1：5-1：1000的范围内进一步选择，例如，所述固体酸和美拉德反应中间体的重量比可以为1：10、1：20、1：50、1：100、1：200或1：500等，但不限于此。在一个具体的实施方式中，所述组合物可以仅由固体酸和美拉德反应中间体组成。According to the present invention, the weight ratio of the solid acid and the Maillard reaction intermediate in the composition can be further selected in the range of 1:5-1:1000, for example, the weight of the solid acid and the Maillard reaction intermediate The ratio may be 1:10, 1:20, 1:50, 1:100, 1:200, or 1:500, etc., but is not limited thereto. In a specific embodiment, the composition may consist solely of the solid acid and the Maillard reaction intermediate.
根据本发明，对固体酸的种类没有特别的限制，可以为常见的固体酸种类。例如，所述固体酸可以为诸如氧化物类、硫化物、金属盐类或杂多酸类等的固体酸。在本发明的一个优选实施方式中，所述固体酸可以为氧化物类固体酸或金属盐类固体酸。进一步地，在本发明的一个优选实施方式中，所述氧化物类固体酸可以选自基于Al2 O3 -SiO2 的混合氧化物、基于Al2 O3 -B2 O3 的混合氧化物和基于ZrO2 -MoO3 的氧化物中的一种或多种；所述金属盐类固体酸可以选自金属硫酸盐和金属磷酸盐中的一种或多种。更进一步地，所述金属盐中的金属可以为例如Fe、Al或Cu等。更进一步地，本发明中所用的固体酸可以更具体地为aNa2 O:bAl2 O3 :cSiO2 ，式中可以为a<0.1％,b/c≈1/25(或例如1/10-1/30等)，一般可以由氧化铝和氧化硅按一定的摩尔比烧制而成，其中氧化钠是杂质，所以控制其含量不高。According to the present invention, the type of solid acid is not particularly limited, and it can be a common type of solid acid. For example, the solid acid may be a solid acid such as oxides, sulfides, metal salts, or heteropolyacids. 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 Al2O3-SiO2-based mixed oxides, Al2O3-B2O3-based mixed oxides, and ZrO2-MoO3-based oxides One or more of these; the metal salt solid acid can be selected from one or more of metal sulfates and metal phosphates. Further, the metal in the metal salt can be, for example, Fe, Al, Cu, or the like. Further, the solid acid used in the present invention can be more specifically aNa2O:bAl2O3:cSiO2, where a<0.1%, b/c≈1/25 (or for example 1/10-1/30 etc.), generally can be fired from alumina and silicon oxide in a certain molar ratio, in which sodium oxide is an impurity, so control its content is not high.
根据本发明，术语“美拉德反应”亦称非酶棕色化反应，是广泛存在于食品工业的一种非酶褐变，是羰基化合物(例如还原糖类)和氨基化合物(例如氨基酸和蛋白质)间的反应，经过复杂的历程最终生成棕色甚至是黑色的大分子物质类黑精或称拟黑素，故又称羰胺反应；而术语“美拉德反应中间体”是指在美拉德反应过程中的中间产物，并且可以由原材料在一定温度下进行不完全的美拉德反应来获得。According to the present invention, the term "Maillard reaction", also known as non-enzymatic browning reaction, is a kind of non-enzymatic browning widely existing in the food industry. ), after a complicated process, a brown or even black macromolecular substance like melanin or pseudomelanin is finally formed, so it is also called carbonylamine reaction; and the term "Maillard reaction intermediate" refers to the reaction in Maillard. It is an intermediate product in the German reaction process, and can be obtained from the incomplete Maillard reaction of raw materials at a certain temperature.
因此，在本发明的一个优选实施方式中，所述美拉德反应中间体可以由氨基酸和糖类物质(二者的摩尔比可以为1：0.5-2，优选为1：1)在50-200℃(例如80℃、100℃、120℃、150℃或180℃等)的条件下进行美拉德反应得到。进一步地，所述美拉德反应可以通过本领域技术人员熟知的方法进行，例如可以通过碱性法进行，即使用碱性催化剂催化上述反应，并在反应结束时加入酸性试剂以调整pH至中性；或可以通过酸性法进行，即使用酸性催化剂催化上述反应，并在反应结束时加入碱性试剂以调整pH至中性。Therefore, in a preferred embodiment of the present invention, the Maillard reaction intermediate can be composed of amino acids and carbohydrates (the molar ratio of the two can be 1:0.5-2, preferably 1:1) between 50- It is obtained by carrying out Maillard reaction under the conditions of 200°C (for example, 80°C, 100°C, 120°C, 150°C or 180°C, etc.). Further, the Maillard reaction can be carried out by a method well known to those skilled in the art, for example, it can be carried out by an alkaline method, that is, an alkaline catalyst is used to catalyze the above reaction, and an acidic reagent is added at the end of the reaction to adjust the pH to medium or can be carried out by an acidic method, that is, an acidic catalyst is used to catalyze the above reaction, and an alkaline reagent is added at the end of the reaction to adjust the pH to neutrality.
更进一步地，在本发明的一个优选实施方式中，所述氨基酸可以选自甘氨酸、丙氨酸、精氨酸、谷氨酸、亮氨酸和异亮氨酸中的至少一种；所述糖类物质可以选自葡萄糖、果糖、蔗糖、乳糖、甘露糖和半乳糖中的至少一种。基于上述可选择的具体氨基酸和糖类物质种类，可以理解，本发明的美拉德反应中间体可以由上述氨基酸和糖类物质的任意组合经美拉德反应得到。Further, in a preferred embodiment of the present invention, the amino acid can be selected from at least one of glycine, alanine, arginine, glutamic acid, leucine and isoleucine; the The carbohydrate substance may be selected from at least one of glucose, fructose, sucrose, lactose, mannose and galactose. Based on the above-mentioned selectable specific types of amino acids and saccharides, it can be understood that the Maillard reaction intermediate of the present invention can be obtained by the Maillard reaction of any combination of the above-mentioned amino acids and saccharides.
另一方面，本发明还提供了一种制备如上所述的组合物的方法，所述方法包括：将所述固体酸和所述美拉德反应中间体接触。In another aspect, the present invention also provides a method for preparing the above-mentioned composition, the method comprising: contacting the solid acid and the Maillard reaction intermediate.
在本发明提供的制备方法中，所述固体酸和所述美拉德反应中间体的接触可以通过任意方式进行，例如可以在以固相、液相或其组合来混合。在本发明的一个优选实施方式中，所述接触可以通过将固体酸和固态美拉德反应中间体研磨混合；和/或可以通过将固体酸浸渍在美拉德反应中间体溶液中来进行。In the preparation method provided by the present invention, the contact of the solid acid and the Maillard reaction intermediate can be carried out in any manner, for example, they can be mixed in a solid phase, a liquid phase or a combination thereof. In a preferred embodiment of the present invention, the contacting may be performed by grinding and mixing the solid acid and the solid Maillard reaction intermediate; and/or may be performed by immersing the solid acid in the Maillard reaction intermediate solution.
在所述接触如上所述通过将固体酸和固态美拉德反应中间体研磨混合来进行时，所述固体酸和固态美拉德反应中间体的混合比例可以为1：5-1：1000(重量比)。在所述接触如上所述通过将固体酸浸渍在美拉德反应中间体溶液中来进行时，所述美拉德反应中间体溶液可以为浓度为5-70％(重量比)美拉德反应中间体的水、乙醇、丙二醇、丙三醇溶液或其组合，并且所述接触还可进一步包括在固体酸浸渍于溶液中2-24小时后，进行低温烘烤或晾干。When the contacting is carried out by grinding and 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 can 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 a Maillard reaction intermediate solution at a concentration of 5-70% by weight. water, ethanol, propylene glycol, glycerol solution or a combination thereof of the intermediate, and the contacting may further include low temperature baking or air drying after the solid acid is immersed in the solution for 2-24 hours.
另一方面，本发明还提供了一种降低卷烟烟气中自由基含量的方法，其包括：在所述卷烟的烟草制剂中加入如上所述的组合物，使得所述卷烟在使用时所产生的烟气中的自由基含量降低。In another aspect, the present invention also provides a method for reducing the content of free radicals in cigarette smoke, comprising: adding the above-mentioned composition to the tobacco preparation of the cigarette, so that the cigarette generates The free radical content in the flue gas is reduced.
另一方面，本发明还提供了一种卷烟，其所使用的烟草制剂中包含如上所述的组合物。In another aspect, the present invention also provides a cigarette, the tobacco formulation used in the cigarette comprises the above-mentioned composition.
根据上述制备本发明的组合物的各种不同方法，在使用本发明的组合物降低卷烟烟气中自由基含量或制备卷烟的过程中也可以采取相应的不同方式。According to the above-mentioned various methods for preparing the composition of the present invention, correspondingly different methods can also be adopted in the process of using the composition of the present invention to reduce the content of free radicals in cigarette smoke or to prepare cigarettes.
例如，在所述卷烟为加热卷烟时，可以将本发明的组合物固体与烟草粉末均匀混合，制备成烟草薄片丝，卷烟纸包裹烟草丝形成烟草段，烟草段与降温嘴棒通过水松纸连接，形成低温卷烟烟支；可以将本发明的组合物配制成水、乙醇、丙二醇、丙三醇溶液或其组合，再与烟草粉末均匀混合，制备成烟草薄片丝，卷烟纸包裹烟草丝形成烟草段，烟草段与降温嘴棒通过水松纸连接，形成低温卷烟烟支；将本发明的组合物配制成水、乙醇、丙二醇、丙三醇溶液或其组合，均匀施加于烟草薄片丝表面，卷烟纸包裹烟草丝形成烟草段，烟草段与降温嘴棒通过水松纸连接，形成低温卷烟烟支；将本发明的组合物配制成水或乙醇或丙二醇或丙三醇的溶液，均匀施加于丝束表面，制备降温嘴棒，卷烟纸包裹烟草丝形成烟草段，烟草段与降温嘴棒通过水松纸连接，形成加热卷烟烟支；将本发明的组合物固体均匀施加于丝束中，制备降温嘴棒，卷烟纸包裹烟草丝形成烟草段，烟草段与降温嘴棒通过水松纸连接，形成加热卷烟烟支；以及将本发明的组合物固体填充于嘴棒中空段的空腔中，制备降温嘴棒，卷烟纸包裹烟草丝形成烟草段，烟草段与降温嘴棒通过水松纸连接，形成加热卷烟烟支。For example, when the cigarette is a heated cigarette, the solid composition of the present invention can be uniformly mixed with tobacco powder to prepare shredded tobacco sheet, cigarette paper wraps the shredded tobacco to form a tobacco segment, and the tobacco segment and the cooling tip rod pass through tipping paper connected to form low-temperature cigarette cigarettes; the composition of the present invention can be formulated into water, ethanol, propylene glycol, glycerin solution or a combination thereof, and then evenly mixed with tobacco powder to prepare shredded tobacco sheet, and cigarette paper wraps the shredded tobacco to form Tobacco segment, the tobacco segment and the cooling tip rod are connected by tipping paper to form a low-temperature cigarette; the composition of the present invention is prepared into water, ethanol, propylene glycol, glycerin solution or a combination thereof, and uniformly applied to the surface of the tobacco sheet , the cigarette paper wraps the tobacco shreds to form tobacco segments, and the tobacco segments and the cooling tip rod are connected by tipping paper to form low-temperature cigarette cigarettes; the composition of the present invention is prepared into a solution of water or ethanol or propylene glycol or glycerol, and uniformly applied On the surface of the tow, a cooling tip rod is prepared, cigarette paper wraps the tobacco shreds to form a tobacco segment, and the tobacco segment and the cooling tip rod are connected by tipping paper to form a heated cigarette; the solid composition of the present invention is uniformly applied to the tow , prepare a cooling tip stick, cigarette paper wraps tobacco shreds to form a tobacco segment, the tobacco segment and the cooling tip stick are connected by tipping paper to form a heated cigarette cigarette; and the composition of the present invention is solidly filled in the cavity of the hollow segment of the tip stick In the process, a cooling tip rod is prepared, cigarette paper wraps shredded tobacco to form a tobacco segment, and the tobacco segment and the cooling tip rod are connected by tipping paper to form a heated cigarette cigarette.
又例如，在所述卷烟为传统卷烟时，可以将本发明的组合物配制成水或乙醇或丙二醇或丙三醇的溶液，均匀施加于烟丝表面，卷烟纸包裹烟丝形成烟草段，烟草段与嘴棒通过水松纸连接，形成卷烟烟支；将本发明的组合物配制成水或乙醇或丙二醇或丙三醇的溶液，均匀施加于卷烟纸表面，卷烟纸包裹烟丝形成烟草段，烟草段与嘴棒通过水松纸连接，形成卷烟烟支；将本发明的组合物配制成水或乙醇或丙二醇或丙三醇的溶液，均匀施加于丝束表面，制备嘴棒，卷烟纸包裹烟丝形成烟草段，烟草段与嘴棒通过水松纸连接，形成卷烟烟支；将本发明的组合物固体均匀施加于丝束中，制备嘴棒，卷烟纸包裹烟丝形成烟草段，烟草段与嘴棒通过水松纸连接，形成卷烟烟支。For another example, when the cigarette is a traditional cigarette, the composition of the present invention can be formulated into a solution of water or ethanol or propylene glycol or glycerol, which is uniformly applied to the surface of the cut tobacco, and the cut tobacco is wrapped with cigarette paper to form a tobacco segment, and the tobacco segment is combined with the tobacco segment. The mouth sticks are connected by tipping paper to form cigarette cigarettes; the composition of the present invention is prepared into a solution of water or ethanol or propylene glycol or glycerol, and is uniformly applied to the surface of the cigarette paper, and the cigarette paper wraps the shredded tobacco to form a tobacco segment, and the tobacco segment It is connected with the tip stick through tipping paper to form a cigarette; the composition of the present invention is formulated into a solution of water or ethanol or propylene glycol or glycerol, which is uniformly applied on the surface of the tow to prepare a tip stick, and the cigarette paper wraps the shredded tobacco to form Tobacco segment, the tobacco segment and the mouth stick are connected by tipping paper to form cigarette cigarettes; the solid composition of the present invention is uniformly applied to the tow to prepare the mouth stick, the cigarette paper wraps the cut tobacco to form the tobacco segment, the tobacco segment and the mouth stick Connected by tipping paper to form cigarettes.
本发明人经过研究发现，在本发明的组合物中，固体酸可以催化美拉德反应中间体的热解，在美拉德反应中间体增香的同时，可以在较低温度(例如200℃或300℃)下，释放较多的抗氧化活性物质，对降低烟气中的自由基含量具有一定的促进作用。The inventors have found through research that, in the composition of the present invention, the solid acid can catalyze the pyrolysis of the Maillard reaction intermediate. or 300 °C), more antioxidant active substances are released, which has a certain promoting effect on reducing the content of free radicals in the flue gas.
以下，将通过实施例对本发明的特定组合物的效果进行详细描述。Hereinafter, the effects of the specific composition of the present invention will be described in detail by way of examples.
实施例1Example 1
酸性法美拉德反应中间体的合成：一定量的葡萄糖和丙氨酸(1：1摩尔比)，在5％(与L-丙氨酸和葡萄糖的总重量的比值)的丙二酸催化作用下，在四倍量(与L-丙氨酸和葡萄糖的总重量的比值)的甲醇中65℃反应8h。待反应完全后加入氢氧化钠中和成中性，得到的美拉德粗品经过膜分离机透析法获取膜截留分子量为500-5000的美拉德反应中间体，然后冷冻干燥，去除其中的溶剂或水分，从而得到固体美拉德中间体。Synthesis of acidic famaillard reaction intermediates: a certain amount of glucose and alanine (1:1 molar ratio), catalyzed by malonic acid at 5% (ratio to the total weight of L-alanine and glucose) Under the action, the reaction was carried out at 65°C for 8h in four times the amount of methanol (ratio to the total weight of L-alanine and glucose). After the reaction is completed, sodium hydroxide is added to neutralize it into neutrality, and the obtained Maillard crude product is subjected to a membrane separator dialysis method to obtain a Maillard reaction intermediate with a membrane molecular weight cut-off of 500-5000, and then freeze-dried to remove the solvent. or moisture to obtain a solid Maillard intermediate.
在如上制得的美拉德反应中间体中加入10％(重量比)的固体酸(实施例中使用的固体酸的化学组成用氧化物的摩尔比表示为：aNa2 O:bAl2 O3 :cSiO2 ，式中a<0.1％,b/c＝1/25)，并混合均匀。Add 10% (weight ratio) solid acid to the Maillard reaction intermediate prepared above (the chemical composition of the solid acid used in the examples is expressed as the molar ratio of oxides: aNa2 O:bAl2 O3 :cSiO2 , where a<0.1%, b/c=1/25), and mix well.
分别对纯的美拉德反应中间体、以及美拉德反应中间体+10％固体酸进行裂解温度为200℃、300℃和400℃的热裂解实验。采用CDS 5250T热解仪和Agilent
7890A-5975C气质联用仪进行裂解和分析。称取约1mg样品，置于裂解管中的石英棉上，然后将裂解管放入裂解仪上待裂解。裂解升温程序：初始温度50℃，以30℃/s升至设置热解温度，保持5s。裂解氛围为氦气，气体流量：70mL/min，裂解仪阀箱温度：280℃，裂解仪传输线温度：280℃。GC-MS方法：弹性石英毛细管柱；固定相为5％苯基-95％甲基聚硅氧烷；规格为[30m(长度)×0.25mm(内径)×0.25μm(膜厚)]；载气流量，1.0mL/min；分流比，100:1；升温程序，初始温度40℃，保持3min，以10℃/min的速率升至240℃，再以20℃/min的速率升至280℃，保持15min；质谱传输线温度280℃；离子源温度230℃；四极杆温度150℃；质量扫描范围29-450amu。裂解产物结果如下表1所示：The pure Maillard reaction intermediate and the Maillard reaction intermediate + 10% solid acid were subjected to thermal cracking experiments with cracking temperatures of 200°C, 300°C and 400°C, respectively. Using a CDS 5250T pyrolyzer and Agilent
7890A-5975C GC-MS for pyrolysis and analysis. Weigh about 1 mg of the sample, put it on the quartz wool in the lysis tube, and then put the lysis tube on the lysis instrument to be lysed. Pyrolysis heating program: the initial temperature was 50°C, and the temperature was raised to the set pyrolysis temperature at 30°C/s, and kept for 5s. The pyrolysis atmosphere is helium gas, the gas flow rate: 70 mL/min, the temperature of the valve box of the pyrolysis apparatus: 280 °C, and the temperature of the transmission line of the pyrolysis apparatus: 280 °C. GC-MS method: elastic quartz capillary column; stationary phase is 5% phenyl-95% methyl polysiloxane; specification is [30m (length) × 0.25 mm (inner diameter) × 0.25 μm (film thickness)]; Air flow, 1.0mL/min; split ratio, 100:1; heating program, initial temperature 40°C, hold for 3min, rise to 240°C at a rate of 10°C/min, and then rise to 280°C at a rate of 20°C/min , maintained for 15min; mass spectrometry transmission line temperature 280 ℃; ion source temperature 230 ℃; quadrupole temperature 150 ℃; mass scanning range 29-450amu. The results of the cleavage products are shown in Table 1 below:
表1葡萄糖-丙氨酸美拉德反应中间体(酸式法，分子量500-5000kDa)在空气气氛下的Py-GC/MS结果(90％N2 +10％O2 气氛)Table 1 Py-GC/MS results of glucose-alanine Maillard reaction intermediate (acid method, molecular weight 500-5000kDa) in air atmosphere (90%N2 +10%O2 atmosphere)
表1示出了葡萄糖-丙氨酸美拉德反应中间体(酸式法，分子量500-5000kDa)在空气气氛下的Py-GC/MS结果。可以看出，加入固体酸后，2,3-二氢-3,5-二羟基-6-甲基-4H-吡喃-4-酮在裂解气中的相对含量增加，而如本领域技术人员所熟知的，2,3-二氢-3,5-二羟基-6-甲基-4H-吡喃-4-酮是具有较强自由基清除作用和抗氧化作用的物质。Table 1 shows the Py-GC/MS results of the glucose-alanine Maillard reaction intermediate (acid method, molecular weight 500-5000 kDa) under air atmosphere. It can be seen that after the addition of solid acid, the relative content of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one in the cracked gas increases, and as shown in the art It is well known to persons that 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one is a substance with strong free radical scavenging effect and antioxidant effect.
混合后的样品在管式炉中300℃裂解，以Ar气氛载流裂解气，用无水乙醇吸收，裂解时间为10min。取稀释裂解气吸收液2mL，0.1mmol/L的DPPH乙醇溶液2mL，加入同一具塞试管中摇匀，于室温密闭静置30min，未加样品液为空白，无本发明组合物的处理为对照，于517nm波长处测定吸光度，并用下式计算DPPH自由基清除率：The mixed samples were cracked at 300°C in a tube furnace, the cracking gas was carried in an Ar atmosphere, and absorbed with anhydrous ethanol, and the cracking time was 10 min. Take 2 mL of diluted pyrolysis gas absorption solution and 2 mL of 0.1 mmol/L DPPH ethanol solution, add it to the same stopper test tube, shake well, and let it stand for 30 min in an airtight environment at room temperature. The sample solution without the addition of the sample solution is blank, and the treatment without the composition of the present invention is the control. , measure the absorbance at a wavelength of 517 nm, and use the following formula to calculate the DPPH free radical scavenging rate:
清除率/％＝(A0－(Ai－Aj))/A0×100Clearance rate/%=(A0-(Ai-Aj))/A0×100
在式中：A0为未加本发明组合物时DPPH溶液的吸光度；Ai为加本发明组合物后DPPH溶液的吸光度；并且Aj为本发明组合物的吸光度，其中DPPH自由基清除率越大则表明抗氧化能力越强。In the formula: A0 is the absorbance of the DPPH solution without adding the composition of the present invention; Ai is the absorbance of the DPPH solution after adding the composition of the present invention; and Aj is the absorbance of the composition of the present invention, wherein the larger the DPPH free radical scavenging rate is The stronger the antioxidant capacity.
结果如图1所示，300℃裂解时，加入固体酸后，裂解气吸收液对DPPH自由基的清除率明显提高。The results are shown in Figure 1. When the pyrolysis is carried out at 300 °C, the scavenging rate of the DPPH radical by the pyrolysis gas absorption liquid is significantly improved after the addition of solid acid.
在加热卷烟中的应用：将混合后的样品固体均匀施加于丝束中(与丝束的重量比为1：400)，制备降温嘴棒，卷烟纸包裹烟草丝形成烟草段，烟草段与降温嘴棒通过水松纸连接，形成加热卷烟烟支，评吸结果表明烘烤香香韵明显；另外将混合后的样品固体与烟草粉末按照重量比1：500均匀混合，制备成烟草薄片丝，卷烟纸包裹烟草薄片丝形成烟草段，烟草段与降温嘴棒通过水松纸连接，形成加热卷烟烟支，评吸结果表明烘烤香、烤甜香香韵明显，香气饱满。Application in heating cigarettes: uniformly apply the mixed sample solids to the tow (the weight ratio to the tow is 1:400), prepare a cooling tip rod, wrap the tobacco shreds with cigarette paper to form a tobacco segment, and the tobacco segment and cooling The mouth sticks are connected by tipping paper to form heated cigarettes, and the smoking evaluation results show that the roasted aroma is obvious; in addition, the mixed sample solids and tobacco powder are uniformly mixed according to the weight ratio of 1:500 to prepare tobacco flakes. The cigarette paper wraps the tobacco sheet to form the tobacco segment, and the tobacco segment and the cooling tip stick are connected by tipping paper to form a heated cigarette.
在传统卷烟中的应用：将混合后的样品配制成乙醇溶液，均匀施加于丝束表面(与丝束的重量比为1:400)，制备嘴棒，卷烟纸包裹烟丝形成烟草段，烟草段与嘴棒通过水松纸连接，形成卷烟烟支，评吸结果表明烘烤香香韵明显；将混合后的样品配制成乙醇溶液，均匀施加于烟丝表面(与烟丝的重量比为1：1000)，卷烟纸包裹烟丝形成烟草段，烟草段与嘴棒通过水松纸连接，形成卷烟烟支，评吸结果表明特征烘烤香、烤甜香香韵明显，香气浓郁饱满协调。Application in traditional cigarettes: The mixed sample is prepared into an ethanol solution, which is uniformly applied to the surface of the tow (the weight ratio to the tow is 1:400) to prepare a mouthpiece, and the shredded tobacco is wrapped with cigarette paper to form a tobacco segment. It is connected with the tip stick through tipping paper to form a cigarette, and the evaluation results show that the roasted aroma is obvious; the mixed sample is prepared into an ethanol solution, which is evenly applied to the surface of the cut tobacco (the weight ratio to the cut tobacco is 1:1000 ), the cigarette paper wraps the cut tobacco to form the tobacco segment, and the tobacco segment and the mouth stick are connected by tipping paper to form the cigarette.
实施例2Example 2
碱性法美拉德中间体的合成：将L-甘氨酸和葡萄糖按1：1摩尔比例混合，加入4倍量(与L-甘氨酸和葡萄糖的总重量的比值)的乙二醇溶剂，并加10％(与L-甘氨酸和葡萄糖的总重量的比值)的NaOH催化剂，130℃下反应6小时。然后再加入2.5倍量(与L-甘氨酸和葡萄糖的总重量的比值)的去离子水溶解，再用1.0mol/L的HCl溶液调整pH至中性，得到的美拉德粗品经过膜分离机透析法获取膜截留分子量为500-5000的美拉德反应中间体，然后冷冻干燥，去除其中的溶剂或水分，从而得到固体美拉德中间体。Synthesis of basic famaillard intermediate: mix L-glycine and glucose in a 1:1 molar ratio, add 4 times the amount of ethylene glycol solvent (ratio to the total weight of L-glycine and glucose), and add 10% (ratio to the total weight of L-glycine and glucose) NaOH catalyst, reacted at 130°C for 6 hours. Then add 2.5 times the amount (the ratio to the total weight of L-glycine and glucose) in deionized water to dissolve, and then adjust the pH to neutrality with 1.0mol/L HCl solution, and the obtained crude Maillard product passes through the membrane separator. A Maillard reaction intermediate with a membrane molecular weight cut-off of 500-5000 is obtained by dialysis, and then freeze-dried to remove the solvent or moisture therein, thereby obtaining a solid Maillard intermediate.
在如上制得的美拉德反应中间体中加入10％(重量比)的固体酸(与实施例1相同)，混合均匀。在与实施例1相同的条件下进行350℃和600℃的裂解实验。裂解产物结果如下表2所示：10% (weight ratio) of solid acid (same as Example 1) was added to the above-prepared Maillard reaction intermediate, and mixed uniformly. The cleavage experiments at 350°C and 600°C were carried out under the same conditions as in Example 1. The results of the cleavage products are shown in Table 2 below:
表2葡萄糖-甘氨酸美拉德反应中间体(碱式法，分子量500-5000kDa)在空气气氛下的Py-GC/MS结果Table 2 Py-GC/MS results of glucose-glycine Maillard reaction intermediates (basic method, molecular weight 500-5000kDa) under air atmosphere
表2示出了葡萄糖-甘氨酸美拉德反应中间体(碱式法，分子量500-5000kDa)在空气气氛下的Py-GC/MS结果。可以看出，加入固体酸后，5-羟甲基糠醛在裂解气中的相对含量增加，而如本领域技术人员所熟知的，5-羟甲基糠醛是具有较强自由基清除作用和抗氧化作用的物质。Table 2 shows the Py-GC/MS results of the glucose-glycine Maillard reaction intermediate (basic method, molecular weight 500-5000 kDa) under air atmosphere. It can be seen that after adding the solid acid, the relative content of 5-Hydroxymethylfurfural in the cracked gas increases, and as is well known to those skilled in the art, 5-Hydroxymethylfurfural has strong free radical scavenging effect and resistance to oxidizing substances.
以与实施例1相同的方法测试对DPPH自由基的清除效果。结果如图2所示，300℃裂解时，加入固体酸后，裂解气吸收液对DPPH自由基的清除率明显提高。The scavenging effect on DPPH radicals was tested in the same manner as in Example 1. The results are shown in Figure 2. When the pyrolysis is carried out at 300 °C, the scavenging rate of the DPPH radical by the pyrolysis gas absorption liquid is significantly improved after adding the solid acid.
在加热卷烟中的应用：将混合后的样品固体与烟草粉末按照质量比1：600均匀混合，制备成烟草薄片丝，卷烟纸包裹烟草薄片丝形成烟草段，烟草段与降温嘴棒通过水松纸连接，形成加热卷烟烟支，评吸结果表明烘烤香、烤甜香香韵明显，香气饱满。Application in heating cigarettes: The mixed sample solids and tobacco powder are uniformly mixed according to the mass ratio of 1:600 to prepare shredded tobacco sheets, cigarette paper wraps the shredded tobacco sheets to form tobacco segments, and the tobacco segments and cooling nozzle rods pass through tipping The paper is connected to form a heated cigarette, and the smoking evaluation results show that the aroma of roasted and roasted sweet is obvious and the aroma is full.
在传统卷烟中的应用：将混合后的样品配制成乙醇溶液，均匀施加于烟丝表面(与烟丝质量的比例为1:800)，卷烟纸包裹烟丝形成烟草段，烟草段与嘴棒通过水松纸连接，形成卷烟烟支，评吸结果表明特征烘烤香、烤甜香香韵明显，香气浓郁饱满协调。Application in traditional cigarettes: The mixed sample is prepared into an ethanol solution, which is uniformly applied to the surface of the cut tobacco (the ratio to the mass of the cut tobacco is 1:800). The paper is connected to form a cigarette, and the evaluation results show that the characteristic roasted aroma and roasted sweet aroma are obvious, and the aroma is rich, full and harmonious.
以上详细描述了本发明的优选实施方式，但是，本发明并不限于上述实施方式中的具体细节，在本发明的技术构思范围内，可以对本发明的技术方案进行多种简单变型，这些简单变型均属于本发明的保护范围。The preferred embodiments of the present invention are described in detail above, but the present invention is not limited to the specific details of the above-mentioned embodiments. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solutions of the present invention. These simple modifications All belong to the protection scope of the present invention.
另外需要说明的是，在上述具体实施方式中所描述的各个具体技术特征，在不矛盾的情况下，可以通过任何合适的方式进行组合，为了避免不必要的重复，本发明对各种可能的组合方式不再另行说明。In addition, it should be noted that the specific technical features described in the above-mentioned specific embodiments can be combined in any suitable manner unless they are inconsistent. In order to avoid unnecessary repetition, the present invention provides The combination method will not be specified otherwise.
此外，本发明的各种不同的实施方式之间也可以进行任意组合，只要其不违背本发明的思想，其同样应当视为本发明所公开的内容。In addition, the various embodiments of the present invention can also be combined arbitrarily, as long as they do not violate the spirit of the present invention, they should also be regarded as the contents disclosed in the present invention.
Claims (11)
- 一种能够降低卷烟烟气中自由基含量的组合物，其特征在于，所述组合物包含固体酸和美拉德反应中间体，其中所述固体酸和美拉德反应中间体的重量比为1：5-1：1000。A composition capable of reducing the content of free radicals in cigarette smoke, characterized in that 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.
- 根据权利要求1所述的组合物，其中，所述固体酸为氧化物类固体酸或金属盐类固体酸。The composition according to claim 1, wherein the solid acid is an oxide-based solid acid or a metal salt-based solid acid.
- 根据权利要求2所述的组合物，其中，所述氧化物类固体酸选自基于Al 2O 3-SiO 2的混合氧化物、基于Al 2O 3-B 2O 3的混合氧化物和基于ZrO 2-MoO 3的混合氧化物中的一种或多种。The composition of claim 2, wherein the oxide-based solid acid is selected from the group consisting of Al2O3-SiO2-based mixed oxides, Al2O3-B2O3-based mixed oxides, and ZrO2-based mixed oxides One or more of the mixed oxides of MoO3.
- 根据权利要求2所述的组合物，其中，所述金属盐类固体酸选自金属硫酸盐和金属磷酸盐中的一种或多种。The composition according to claim 2, wherein the metal salt solid acid is selected from one or more of metal sulfates and metal phosphates.
- 根据权利要求1所述的组合物，其中，所述美拉德反应中间体由氨基酸和糖类物质在50-200℃的条件下进行美拉德反应得到。The composition according to claim 1, wherein the Maillard reaction intermediate is obtained by performing Maillard reaction between amino acids and carbohydrates at a temperature of 50-200°C.
- 根据权利要求5所述的组合物，其中，所述氨基酸选自甘氨酸、丙氨酸、精氨酸、谷氨酸、亮氨酸和异亮氨酸中的至少一种。The composition of claim 5, wherein the amino acid is selected from at least one of glycine, alanine, arginine, glutamic acid, leucine and isoleucine.
- 根据权利要求5所述的组合物，其中，所述糖类物质选自葡萄糖、果糖、蔗糖、乳糖、甘露糖和半乳糖中的至少一种。The composition according to claim 5, wherein the carbohydrate substance is selected from at least one of glucose, fructose, sucrose, lactose, mannose and galactose.
- 一种制备根据权利要求1-7中任一项所述的组合物的方法，其包括：将所述固体酸和所述美拉德反应中间体接触。A method of preparing the composition of any one of claims 1-7, comprising: contacting the solid acid and the Maillard reaction intermediate.
- 根据权利要求8所述的方法，其中，所述接触通过将固体酸和固态美拉德反应中间体研磨混合；和/或通过将固体酸浸渍在美拉德反应中间体溶液中来进行。The method of claim 8, wherein the contacting is performed by grinding and mixing the solid acid and the solid Maillard reaction intermediate; and/or by immersing the solid acid in a solution of the Maillard reaction intermediate.
- 一种降低卷烟烟气中自由基含量的方法，其包括：在所述卷烟的烟草制剂中加入根据权利要求1-9中任一项所述的组合物，使得所述卷烟在使用时所产生的烟气中的自由基含量降低。A method for reducing the content of free radicals in cigarette smoke, comprising: adding the composition according to any one of claims 1 to 9 in the tobacco formulation of the cigarette, so that the cigarette generates a The free radical content in the flue gas is reduced.
- 一种卷烟，其所使用的烟草制剂中包含根据权利要求1-9中任一项所述的组合物。A cigarette comprising the composition according to any one of claims 1-9 in a tobacco formulation used.
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