CN114806711B - Preparation method and application of perfume raw material based on 3-deoxyglucosone - Google Patents
Preparation method and application of perfume raw material based on 3-deoxyglucosone Download PDFInfo
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- 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
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- 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
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/305—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances of undetermined constitution characterised by their preparation
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- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
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- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
- A24B15/385—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom in a five-membered ring
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- 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
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
- A24B15/406—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms in a five-membered ring
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/08—Deoxysugars; Unsaturated sugars; Osones
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- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
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- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0092—Heterocyclic compounds containing only N as heteroatom
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Abstract
The invention discloses a preparation method and application of a perfume raw material based on 3-deoxyglucosone, comprising the following steps: 1) Reacting D-glucose, p-toluidine and benzoyl hydrazine in ethanol containing acetic acid to obtain 3-DG diphenyl hydrazone; 2) Hydrolyzing the 3-DG diphenyl hydrazone in the step 1) in an ethanol water solution containing acetic acid, and then reacting with benzaldehyde to finally generate a product 3-DG; 3) Reacting glucose, amino acid and 3-DG in an aqueous solution; 4) Stopping the reaction by ice water after the reaction of the step 3) is finished, and filtering to remove insoluble matters; 5) Adding an extractant into the filtered solution in the step 4), extracting for 5-8 times, and then combining the extracted filtrate; 6) Adding magnesium sulfate into the extracted filtrate to remove water in the filtrate, and then spin-drying the solvent by a rotary evaporator to recover a sample to obtain a fragrance raw material; the tobacco smoke quality improving agent is applied to single-material cigarettes, so that the aroma quality and the aroma quantity of the smoke are effectively improved, and the smoking quality of the tobacco leaves is improved.
Description
Technical Field
The invention relates to the technical field of Maillard reaction, in particular to a preparation method and application of a perfume raw material based on 3-deoxyglucosone.
Background
3-deoxyglucosone (3-DG) is an alpha-dicarbonyl compound, and is one of important active intermediates in Maillard reaction, and is widely used in the processes of food, tobacco and the like, such as processing, fermentation, storage and the like. It is a precursor of volatile fragrant substances such as furfural, pyrazine, pyrrole and the like in Maillard reaction. In the Maillard reaction, the formation route of 3-deoxyglucosone is as follows: nucleophilic addition of reducing sugar and amino acid to form Schiff base, which cyclizes to form N-glucosamine; then Amadori rearrangement reaction is carried out to generate Amadori compound. Wherein the Amadori compound undergoes 1, 2-enolization and deamination rearrangement under acidic conditions to form 3-deoxyglucosone. Since 3-deoxyglucosone is relatively reactive, it can then react with relatively instability: cyclizing to form 5-hydroxymethyl furfural or pyrrole substance, breaking 3, 4-carbon bond to form methylglyoxal and glyceraldehyde, condensing retro-aldol to form butanedione and glycolaldehyde, or performing Strecker degradation reaction to form Strecker aldehyde and aminoketone. The micromolecular aldehyde ketone furfural pyrrole substances generated by degradation finally form heterocyclic aromatic substances and macromolecular melanoidins in Maillard reaction. Thus, 3-deoxyglucosone is an important class of active intermediates in maillard reactions, which are key precursors for the formation of flavour materials, but the preparation and use of 3-deoxyglucosone-based flavour raw materials is lacking in practical applications.
The present invention provides a new solution to this problem.
Disclosure of Invention
In view of the above, the present invention aims to overcome the drawbacks of the prior art, and to provide a method for preparing a 3-deoxyglucosone-based perfume raw material and application thereof.
The technical scheme for solving the problems is as follows: a method for preparing a 3-deoxyglucosone-based fragrance raw material, comprising the following steps:
1) Reacting D-glucose, p-toluidine and benzoyl hydrazine in ethanol containing acetic acid to obtain 3-DG diphenyl hydrazone;
2) Hydrolyzing the 3-DG diphenyl hydrazone in the step 1) in an ethanol water solution containing acetic acid, and then reacting with benzaldehyde to finally generate a product 3-DG;
3) Reacting glucose, amino acid and 3-DG in water solution at 90-100deg.C for 40-50min;
4) Stopping the reaction by ice water after the reaction of the step 3) is finished, and filtering to remove insoluble matters;
5) Adding an extractant into the filtered solution in the step 4), extracting for 5-8 times, and then combining the extracted filtrate;
6) Adding magnesium sulfate into the extracted filtrate to remove water in the filtrate, and spin-drying the solvent by a rotary evaporator to recover a sample to obtain the perfume raw material.
Further, in the step 1), the molar ratio of D-glucose, p-toluidine and benzoyl hydrazine is 1:1:2.2.
Further, in the step 1), the volume ratio of acetic acid to ethanol is 1:18.
Further, the reaction time of the step 1) is 7 hours or more, and the reaction time of the step 2) is 3 hours or more.
Further, the molar ratio of 3-DG diphenylhydrazone to benzaldehyde in the step 2) is 1:3.
Further, in the step 2), the volume ratio of acetic acid, ethanol and water is 1:64:129.
Further, the extractant in the step 5) is ethyl acetate.
Further, after the reaction in the step 1), the reaction mixture is washed with methanol, diethyl ether and methanol three times or more in sequence.
Further, after the reaction in the step 2), adjusting the pH to be neutral by NaOH; washing with diethyl ether for more than 6 times; and (3) decoloring with active carbon.
Further, the application is the perfuming application of the prepared perfume raw material in tobacco.
Through the technical scheme, the invention has the beneficial effects that: according to the invention, the 3-DG active intermediate participates in a glucose/amino acid Maillard reaction system, so that a 3-deoxyglucosone-based perfume raw material is prepared, and the promotion of the variety and content of perfume substances is effectively promoted; the tobacco smoke flavor quality and the aroma quantity of the smoke can be effectively improved and the tobacco smoking quality can be improved by applying the tobacco smoke flavor quality and the aroma quantity of the smoke to single-material cigarettes.
Detailed Description
The foregoing and other features, aspects and advantages of the invention will become more apparent from the following detailed description of the embodiments.
Various exemplary embodiments of the invention are described below.
1. Preparation of 3-DG:
the first step is the preparation of 3-DG diphenyl hydrazone: d-glucose (10.0 g,55.5 mmol) and p-toluamide (5.95 g,55.5 mmol) were simultaneously added to a mixed solvent of ethanol (200 mL) and acetic acid (11 mL), and after reacting under reflux for 30min, benzoyl hydrazine (16.5 g,121.2 mmol) was added to the above mixture, followed by reacting under reflux for 7h. After the reaction, the reaction mixture was cooled to room temperature (25 ℃) under stirring, then the mixture was filtered to collect a cake, and the cake was washed with methanol (3×100 mL), diethyl ether (3×100 mL) and methanol (3×100 mL) in this order for 3 times, and finally the cake was dried to obtain a pale yellow target compound (19.8 g, yield 90%);
the material is infrared (KBr, v/cm) -1 ) The results were: 3375,3263,3066,2930,2868,1648, 1580,1538,1491,1448,1278,1188,1139,1082,961,695; the mass spectrum results were: [ M+Na ]] + ＝C 20 H 22 N 4 O 5 Na, theoretical 421.1488, found 421.1484; the nuclear magnetic resonance hydrogen spectrum result is% 1 H NMR,400MHz, deuterium-band DMSO): delta 8.19 (m, 1H, CNH), 7.89 (m, 4H, C 6 H 5 ),7.56(m,5H,C 6 H 5 ),6.18(m,2H,NH),5.07(m,1H,CH 2 ),4.55 (m,1H,CH 2 ),3.85(m,1H,CH 2 ),3.58(m,1H,CH 2 ),3.42(m,3H,OH),3.11(m, 1H,CH),2.92(m,1H,CH)。
The second step is the preparation of 3-DG: 3-DG diphenylhydrazone (10.0 g,25.1 mmol) and benzaldehyde (7.68 mL,75.3 mmol) were sequentially added to a mixed solvent of ethanol (200 mL), water (400 mL), and acetic acid (3.1 mL), and the reaction was heated under reflux for 3 hours, wherein the observed phenomenon was that the reactant was gradually dissolved as a pale yellow clear solution, and brown solid product formation was observed as the reaction proceeded. The reaction was stopped by TLC when all 3-DG diphenylhydrazone was reacted. After completion of the reaction, the reaction solution was cooled to room temperature (25 ℃), and the filtrate was obtained by filtration. The filtrate was concentrated to 100mL by rotary evaporator. After the pH of the filtrate was adjusted to neutrality with NaOH solution (1.0 mol/L), the filtrate was washed several times with diethyl ether (6X 100 mL). Adding activated carbon particles (10 g) into the filtrate to remove colored substances in the filtrate, standing for 10min, and filtering to remove the activated carbon particles in the filtrate; concentrating the obtained filtrate to 5mL by a rotary evaporator, and freeze-drying at low temperature to obtain brown powdery solid, thus obtaining the target compound 3-deoxyglucosone (2.0 g, yield 50%);
the material is infrared (KBr, v/cm) -1 ) The results were: 3411,2984,2934,2884,1578,1417, 1337,1045,1020,925,704,650,620; the mass spectrum results were: [ M+Na ]] + ＝C 6 H 10 O 5 Na, theoretical 185.0426, found 185.0430; the result of nuclear magnetic resonance hydrogen spectrum is% 1 H NMR,400MHz, deuterium-band DMSO): delta is 5.16-3.14 (m, 7H, CH) 2 OHCHOHCHOH),1.75(m, 2H,CH 2 )。
2. Effect of 3-DG on the aroma components of the glucose/amino acid maillard reaction system:
example 1: the amino acid being alanine
Reaction conditions: glucose (0.50 g,2.77 mmol), alanine (0.25 g,2.77 mmol) and 3-DG (0.025 g,0.154 mmol) are reacted in aqueous solution (8 ml) at a reaction temperature of 100 ℃ for 30min, after the reaction is finished, the reaction is stopped by ice water, insoluble substances are removed by filtration, extraction is carried out for 5 to 8 times by ethyl acetate, the filtrates are combined, anhydrous magnesium sulfate is added to remove the moisture in the filtrate, and finally the solvent is recovered for standby by spin drying by a rotary evaporator at 50 ℃.
The sample was analyzed by gas analysis:
gas analysis conditions: dissolving 0.1g of the sample in 1mL of methanol, filtering through a 0.22 mu m organic phase filter membrane, and performing GC-MS analysis;
gas chromatography conditions: HP-5MS fused silica capillary column (30 m.times.250 μm.times.0.25 μm); the temperature of the sample inlet is 300 ℃; the sample injection amount is 1 mu L; the carrier gas is high-purity helium (purity 99.9999%); the flow rate is 1mL/min; the temperature-raising program is as follows: the temperature of the sample inlet is 250 ℃; the column temperature is kept at 40 ℃ for 4min, and the column temperature is kept at 6 ℃/min to 100 ℃,4 ℃/min to 250 ℃ for 5min without diversion; the solvent was delayed for 3.5min.
Mass spectrometry conditions: electron bombardment ion source (EI), ion source temperature of 250 ℃, ionization energy of 70eV, transmission line temperature of 200 ℃, mass spectrum scanning range of 30-400amu;
and (3) data processing: qualitative analysis adopts gas quality work station NIST14 and Wiley spectrogram search, is characterized by matching degree higher than 85%, and is compared with the spectrogram analysis result in literature. Quantitative analysis was performed according to the internal standard method.
Results of gas analysis: see Table 1
TABLE 1 influence of the addition of 5%3-DG on the type and content of products of the glucose/alanine reaction system (ug/g)
Note that: "-means that the substance is not detected.
The results show that: compared with a glucose/alanine reaction system without 3-DG, the type and the content of the products of the reaction system with 3-DG are greatly improved, the types of the products are increased from 9 to 12, and the contents of furans, pyrones, esters and acid substances are greatly increased. The maximum increase in the content of pyrones is probably due to the fact that the intramolecular rearrangement of 3-deoxyglucurone in the Maillard reaction is the main route for the formation of pyrones, and thus the addition of this substance promotes the further accumulation of pyrones.
Example 2: the amino acid being glycine
Reaction conditions: as in example 1, glycine was used in an amount of 0.208g,2.77mmol.
Gas analysis conditions: as in example 1;
results of gas analysis: as shown in table 2.
TABLE 2 influence of the addition of 5%3-DG on the type and amount of products of the glucose/glycine reaction System (ug/g)
Note that: "-means that the substance is not detected.
The results show that: compared with a glucose/glycine reaction system without 3-DG, the reaction system with 3-DG has less variation of the types of products, but has a large improvement of the content of most products. Wherein the content of 4-hydroxy-2, 5-dimethyl-3 (2H) -furanone, 3, 5-dihydroxy-6-methyl-2H-4 (3H) -pyrone, 3-hydroxy-2-picoline and benzoic acid are greatly increased, and the substances have different fragrances to endow the novel fragrance type of a glucose/glycine/3-DG system.
Example 3: the amino acid being proline
Reaction conditions: as in example 1, proline was used in an amount of 0.318g,2.77mmol.
Gas analysis conditions: as in example 1;
results of gas analysis: as shown in table 3.
TABLE 3 influence of the addition of 5%3-DG on the type and content of products of the glucose/proline reaction system (ug/g)
Note that: "-means that the substance is not detected.
The results show that: compared with a glucose/proline reaction system without 3-DG, the variety of the products of the reaction system with 3-DG is obviously improved, and the variety number is increased from 5 to 14. Among the added substances, beta-dihydroionone has the fragrance of the costustoot flower fragrance and the fruit fragrance; 3-phenyl furan has an aromatic odor; 3, 4-dimethyl-3-hexen-2-one has the fragrance of stir-fried hazelnuts; the hexanol phenylacetate can be used in a soap essence formulation; it is known that the addition of 3-DG, a Maillard reactive intermediate, contributes to the generation of flavour components.
Example 4: the amino acid being phenylalanine
Reaction conditions: as in example 1, phenylalanine was used in an amount of 0.458g,2.77mmol.
Gas analysis conditions: as in example 1;
results of gas analysis: as shown in table 4.
TABLE 4 influence of the addition of 5%3-DG on the type and content of the products of the glucose/phenylalanine reaction system (ug/g)
Note that: "-means that the substance is not detected.
The results show that: compared with a glucose/phenylalanine reaction system without 3-DG, the type and the content of the products of the reaction system with 3-DG are greatly improved. The number of the products is increased from 14 to 16, and the contents of the fragrant substances 2-acetylpyrrole, benzaldehyde, phenylacetaldehyde, hexanol phenylacetate and the like are also greatly improved except for 3, 5-dihydroxyl-6-methyl-2H-4 (3H) -pyrone, so that the 3-DG active intermediate can participate in certain specific reactions of Maillard reaction to promote the increase of the contents of certain specific substances.
Example 5: the amino acid being glutamic acid
Reaction conditions: the same as in example 1, wherein glutamic acid was used in an amount of 0.408g,2.77mmol.
Gas analysis conditions: as in example 1;
results of gas analysis: as shown in table 5.
TABLE 5 influence of the addition of 5%3-DG on the type and content of the products of the glucose/glutamic acid reaction system (ug/g)
Note that: "-means that the substance is not detected.
The results show that: compared with a glucose/glutamic acid reaction system without 3-DG, the type and the content of the products of the reaction system with 3-DG are greatly improved. The variety of the products is increased from 7 to 12, and the flavor substances 2-acetylpyrrole, 3-hydroxy-2-methylpyridine, 3-hydroxybutyraldehyde, 5-hydroxymethylfurfural, benzoic acid and the like are greatly increased, so that the addition of 3-DG is further explained to be beneficial to the generation of the flavor substances in a glucose/amino acid Maillard reaction system.
3. 3 evaluation of aroma-adding evaluation of deoxyglucosone in tobacco shred
The specific operation steps are as follows: 1. Mu.L of a flavoring solution (flavoring amount 70 mg/kg) was injected into each blank cigarette by a cigarette flavoring injector. The reference cigarette is a blank cigarette injected with an equal amount of 50% ethanol solution. The flavored sample cigarettes and the reference cigarettes are respectively sealed and then are balanced for 48 hours in a constant temperature and humidity box with the temperature of (22+/-1) DEG and the relative humidity of (60+/-2). Sensory evaluation is carried out by referring to a YC/T497-2014 method, and the change of the aroma style index of the cigarette sample is recorded.
The evaluation results of the flavoring and sucking are shown in Table 6.
TABLE 6 evaluation of flavoring Effect of 3-DG at different concentrations in Single cigarettes
As can be seen from Table 6, the single-material cigarettes after 3-DG is added show burnt aroma, and the aroma, the aroma quality, the permeability, the smoke concentration and the like of the smoke are improved greatly.
While the invention has been described in connection with certain embodiments, it is not intended that the invention be limited thereto; for those skilled in the art to which the present invention pertains and the related art, on the premise of based on the technical scheme of the present invention, the expansion, the operation method and the data replacement should all fall within the protection scope of the present invention.
Claims (9)
1. A process for the preparation of a 3-deoxyglucosone-based fragrance raw material, characterized in that it comprises the following steps:
1) Reacting D-glucose, p-toluidine and benzoyl hydrazine in ethanol containing acetic acid to obtain 3-deoxyglucurolactone diphenyl hydrazone;
2) Hydrolyzing the 3-deoxyglucosone diphenyl hydrazone in the step 1) in an ethanol water solution containing acetic acid, and then reacting with benzaldehyde to finally generate a product 3-deoxyglucosone;
3) Reacting glucose, amino acid and 3-deoxyglucosone in water solution at 90-100deg.C for 40-50min;
4) Stopping the reaction by ice water after the reaction of the step 3) is finished, and filtering to remove insoluble matters;
5) Adding an extracting agent ethyl acetate into the filtered solution in the step 4), extracting for 5-8 times, and then combining the extracted filtrate;
6) Adding magnesium sulfate into the extracted filtrate to remove water in the filtrate, and spin-drying the solvent by a rotary evaporator to recover a sample to obtain the perfume raw material.
2. A process for the preparation of a 3-deoxyglucosone-based fragrance raw material according to claim 1, characterized in that: the molar ratio of D-glucose, p-toluidine and benzoyl hydrazine in the step 1) is 1:1:2.2.
3. A process for the preparation of a 3-deoxyglucosone-based fragrance raw material according to claim 2, characterized in that: the volume ratio of acetic acid to ethanol in the step 1) is 1:18.
4. A process for the preparation of a 3-deoxyglucosone-based fragrance raw material according to claim 3, characterized in that: the reaction time of the step 1) is more than 7 hours, and the reaction time of the step 2) is more than 3 hours.
5. A process for the preparation of a 3-deoxyglucosone-based fragrance raw material according to claim 1, characterized in that: the molar ratio of 3-deoxyglucurolactone diphenyl hydrazone to benzaldehyde in the step 2) is 1:3.
6. A process for the preparation of a 3-deoxyglucosone-based fragrance raw material as defined in claim 5, characterized in that: the volume ratio of acetic acid, ethanol and water in the step 2) is 1:64:129.
7. A process for the preparation of a 3-deoxyglucosone-based fragrance raw material as claimed in claim 6, characterized in that: and after the reaction in the step 1), washing with methanol, diethyl ether and methanol for more than three times in sequence.
8. A process for the preparation of a 3-deoxyglucosone-based fragrance raw material according to claim 1, characterized in that: after the reaction of the step 2), adjusting the pH value to be neutral by NaOH; washing with diethyl ether for more than 6 times; and (3) decoloring with active carbon.
9. Use of a fragrance raw material prepared by the preparation method according to claim 1, characterized in that: the application is the perfuming application of the prepared perfume raw material in tobacco.
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| DE19932494A1 (en) * | 1999-07-12 | 2001-01-18 | Haarmann & Reimer Gmbh | 4-alkanoyl-3-thazolines and their use as fragrances and flavorings |
| CN1594262A (en) * | 2004-07-04 | 2005-03-16 | 云南烟草科学研究院 | Synthesis method of additive for organic acid ammonium cigarette and its application in tobacco |
| JP4908296B2 (en) * | 2007-04-11 | 2012-04-04 | 山形県 | Processing method of sake |
| JP2010090062A (en) * | 2008-10-08 | 2010-04-22 | Sankyo:Kk | Soft capsule prevented from or suppressed in generation of disagreeable odor peculiar to gelatin |
| CN102100397B (en) * | 2010-12-22 | 2013-04-10 | 湖南中烟工业有限责任公司 | Flavoring essence for tobacco and preparation method thereof |
| CN106281687A (en) * | 2016-08-31 | 2017-01-04 | 四川中烟工业有限责任公司 | A kind of method that Fructus Vitis viniferae concentrate and aromatics beta amino acids prepare tobacco aromatics using |
| CN106190566A (en) * | 2016-08-31 | 2016-12-07 | 四川中烟工业有限责任公司 | A kind of method that Fructus Mali pumilae extract and aromatics beta amino acids prepare tobacco aromatics using |
| CN106244322A (en) * | 2016-08-31 | 2016-12-21 | 四川中烟工业有限责任公司 | A kind of method that Chinese date extract and aromatics beta amino acids prepare tobacco aromatics using |
| CN106723300A (en) * | 2016-12-08 | 2017-05-31 | 深圳市华加生物科技有限公司 | Electronics tobacco tar perfume base and electronics tobacco tar |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112980580A (en) * | 2021-03-11 | 2021-06-18 | 吉林烟草工业有限责任公司 | Maillard reaction spice and preparation method and application thereof |
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