CN112552271A - 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate and application thereof - Google Patents
2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate and application thereof Download PDFInfo
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- CN112552271A CN112552271A CN202011455666.8A CN202011455666A CN112552271A CN 112552271 A CN112552271 A CN 112552271A CN 202011455666 A CN202011455666 A CN 202011455666A CN 112552271 A CN112552271 A CN 112552271A
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- pyran
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
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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
- 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
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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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Tobacco Products (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention relates to 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate ester and application, the technical proposal takes 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone as raw material, and prepares 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate ester through esterification reaction, the compound has good storage stability and perfuming stability, when being added into cigarettes, the compound can release 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone and benzyl alcohol by cracking, not only can increase sweet and moist feeling of the oral cavity and improve the aftertaste comfort, but also can enrich the cigarette fragrance, improve the aroma quality of the cigarette and have potential application value.
Description
Technical Field
The invention belongs to the technical field of tobacco flavor synthesis, and particularly relates to 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate and application thereof as a flavor in cigarettes.
Background
In order to show the characteristic, substances such as saccharides, extractum, Maillard reactants and the like are usually used in Chinese style cigarette flavoring, mainly because the substances contain or can be cracked to generate volatile sweet substances such as pyrones, dehydrated saccharides and the like, but the sweet substance content is extremely low, so the cigarette sweet characteristic is not good.
2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is commonly present in cigarette smoke, Maillard reaction products, sugar cracking products and natural extractum. The 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone has better water solubility, presents prominent sweet taste in taste sense, is in obvious positive correlation with the sweet taste of smoke, can obviously improve the sweet return feeling of the smoke of the cigarette, and highlights the taste characteristics of the sweet taste and the moist taste of the cigarette. However, the stability of DDMP is poor, and the DDMP has not been applied as a tobacco fragrance raw material to date. Through literature and experimental research, 5-enol-type exposed hydroxyl is a main factor of deterioration of the compound, and the stability of the compound can be obviously improved by bonding 5-hydroxyl.
Disclosure of Invention
The invention aims to provide 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate and application thereof in cigarettes.
In order to achieve the purpose, the invention provides the following technical scheme:
a2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate ester, the structure is:
the preparation method of the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate comprises the following steps:
1) adding DDMP and an organic solvent into a reaction bottle, and cooling to-5 ℃ under the protection of nitrogen;
2) sequentially adding organic base and benzyl chloroformate at the temperature of the step 1), and heating to 20-30 ℃ for reacting for 4-8 h;
3) after the reaction is finished, washing the organic mixed solution by using a saturated sodium chloride solution, drying the organic mixed solution by using anhydrous sodium sulfate, evaporating the solvent under reduced pressure, and separating a crude product by using silica gel column chromatography to obtain the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate.
Further, the organic solvent in step 1) is one of dichloromethane, chloroform or acetonitrile.
Further, the base in the step 2) is one of triethylamine, pyridine or diisopropylethylamine.
Further, the mole ratio of DDMP, organic base and benzyl chloroformate is 1: (1-1.5): (1-2).
An application of 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate, and an application of any one of the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate in cigarettes.
Further, an alcohol solution of 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate is sprayed on the cut tobacco.
Further, the addition amount of the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate is 1-50 ppm of the mass of the cut tobacco.
The invention has the beneficial effects that:
the technical proposal takes 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone as raw material, preparing tobacco fragrance raw material 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate through reaction with benzyl chloroformate, the compound has good storage stability and flavoring stability, not only shows the effects of increasing sweet feeling of oral cavity and improving aftertaste comfort when being added into cigarettes, but also can enrich cigarette fragrance, improve cigarette fragrance quality and have potential application value.
Detailed Description
The technical solutions of the present invention are described in detail below by examples, and the following examples are only exemplary and can be used only for explaining and explaining the technical solutions of the present invention, but not construed as limiting the technical solutions of the present invention.
The compound is chemically stable, can release DDMP and benzyl alcohol during high-temperature pyrolysis, can increase the sweet taste of the oral cavity and improve the aftertaste comfort when added into cigarettes, wherein the benzyl alcohol can enrich the cigarette fragrance, improve the cigarette fragrance quality, and has potential application value.
Example 1
DDMP (2.88g,20mmol) is dissolved in 50mL of anhydrous dichloromethane, cooled to 0 ℃, added with triethylamine (2.42g,24mmol) and benzyl chloroformate (3.58g,21mmol) in sequence under the protection of nitrogen, and heated to 25 ℃ for reaction for 6 h. The reaction solution was washed with a saturated sodium chloride solution to separate an organic layer, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and the residue was purified by silica gel column chromatography to obtain 5.06g of a target 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate in 91.0% yield.
Example 2
DDMP (2.88g,20mmol) is dissolved in 50mL of anhydrous chloroform, cooled to 0 ℃, added with pyridine (1.90g,20mmol) and benzyl chloroformate (4.26g,25mmol) in sequence under the protection of nitrogen, and reacted for 6h after the addition is finished and the temperature is raised to 25 ℃. The reaction solution was washed with a saturated sodium chloride solution to separate an organic layer, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and the residue was purified by silica gel column chromatography to obtain 4.89g of a target 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate in 87.9% yield.
Example 3
DDMP (2.88g,20mmol) is dissolved in 50mL acetonitrile, cooled to 0 ℃, pyridine (2.28g,24mmol) and benzyl chloroformate (4.26g,25mmol) are added in sequence under nitrogen protection, and after the addition, the temperature is raised to 25 ℃ for reaction for 6 h. The reaction solution was washed with a saturated sodium chloride solution to separate an organic layer, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and the residue was purified by silica gel column chromatography to obtain 5.01g of a target 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate in 90.1% yield.
Example 4
DDMP (2.88g,20mmol) was dissolved in 50mL acetonitrile, cooled to 0 deg.C, diisopropylethylamine (3.10g,24mmol), benzyl chloroformate (4.26g,25mmol) were added in sequence under nitrogen, and the temperature was raised to 25 deg.C for 6 h. The reaction solution was washed with a saturated sodium chloride solution to separate an organic layer, dried over anhydrous sodium sulfate, evaporated to remove the solvent, and the residue was purified by silica gel column chromatography to obtain 4.41g of a target 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate in 90.1% yield.
Testing the performance of the spice: respectively weighing a certain amount of 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid benzyl alcohol ester (DDMP benzyl alcohol carbonate) and 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP), and diluting the solution into a 5% solution by using ethanol to prepare the raw material of the tobacco fragrance for later use. Weighing 100g of blank cigarette tobacco shreds without flavoring materials, evenly spreading the blank cigarette tobacco shreds in a clean tray, evenly spraying DDMP benzyl alcohol carbonate and DDMP solution on the tobacco shreds respectively to prepare flavored tobacco shreds with the DDMP benzyl alcohol carbonate and the DDMP solution having the specific gravity of 5ppm, 10ppm, 20ppm, 30ppm and 50ppm respectively, sealing and placing the flavored tobacco shreds for 4 hours, placing the flavored tobacco shreds in an oven at 50 ℃ for drying, humidifying the flavored tobacco shreds to standard moisture (12%) with distilled water, rolling the flavored tobacco shreds into standard cigarettes, balancing the moisture (the humidity is 60% +/-2%, and the temperature is 22 +/-1 ℃) for 48 hours, and then performing smoking evaluation. The control sample was a blank cigarette and the control sample was equilibrated for 48h under the same temperature and humidity conditions.
TABLE 1DDMP benzyl alcohol carbonate and DDMP perfuming smoke panel test results
As can be seen from Table 1: the DDMP benzyl alcohol carbonate and the DDMP have the characteristics of remarkably improving the 'back sweetness' of cigarette smoke, highlighting the 'sweet' and 'moist' taste characteristics of the cigarettes, improving and modifying the fragrance of the cigarettes, reducing the irritation, improving the smoking taste and enabling the residual taste to be clean and comfortable. Wherein, compared with DDMP, DDMP benzyl alcohol carbonic ester can also increase the fragrance and the fineness of the smoke, improve the fragrance quality of the cigarette, and has potential application value. When the amount of the DDMP benzyl alcohol carbonate exceeds 30ppm, the DDMP benzyl alcohol carbonate has sweet and greasy feeling and scorched smell, influences the fragrance quality of smoke, deteriorates the aftertaste and generates discomfort, and the recommended dosage is as follows: 10 to 30 ppm.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (8)
1. A 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid benzyl alcohol ester characterized by the structure:
2. the benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate according to claim 1, characterized in that it is prepared by a process comprising the steps of:
1) adding DDMP and an organic solvent into a reaction bottle, and cooling to-5 ℃ under the protection of nitrogen;
2) sequentially adding organic base and benzyl chloroformate at the temperature of the step 1), and heating to 20-30 ℃ for reacting for 4-8 h;
3) after the reaction is finished, washing the organic mixed solution by using a saturated sodium chloride solution, drying the organic mixed solution by using anhydrous sodium sulfate, evaporating the solvent under reduced pressure, and separating a crude product by using silica gel column chromatography to obtain the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate.
3. The benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate according to claim 2, wherein the organic solvent in step 1) is one of dichloromethane, trichloromethane, or acetonitrile.
4. The benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate according to claim 2, wherein the base in step 2) is one of triethylamine, pyridine or diisopropylethylamine.
5. The benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate according to claim 2, wherein the molar ratio of DDMP, organic base, and benzyl chloroformate is from 1: (1-1.5): (1-2).
6. Use of benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate, characterized in that the benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate according to any one of claims 1 to 5 is used in cigarettes.
7. Use of benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate according to claim 6, characterised in that an alcoholic solution of benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate is sprayed onto tobacco shreds.
8. The use of benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate according to claim 7, wherein the amount of benzyl 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate added is 1-50 ppm of the mass of the cut tobacco.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113603596A (en) * | 2021-08-05 | 2021-11-05 | 四川三联新材料有限公司 | Benzyl alcohol ambroxol carbonate latent aroma compound and preparation method and application thereof |
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