Method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one

Abstract

The present invention discloses a method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP). The method involves contacting DDMP with at least one tertiary amine compound having the structural formula: #imgabs0#, wherein R1 is a methyl group, an ethyl group, or a phenyl group; and R2 is a phenyl group or hydrogen. The present invention provides a method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one. DDMP is almost completely degraded after 180 days of storage. However, after adding the tertiary amine compound, degradation is only 8% at most within 180 days. This method successfully addresses the issues of DDMP's poor stability, easy deterioration and damage, and its unsuitability for use as a sweet and fragrant raw material.

Description

Technical Field

[0001] The present invention relates to the technical field of tobacco flavorings, and in particular to a method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one. Background Art

[0002] 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is commonly found in cigarette smoke, Maillard reaction products, sugar cleavage products, and natural extracts. DDMP has good water solubility and a prominent sweetness, which is significantly positively correlated with the sweetness of cigarette smoke. It can significantly enhance the sweet aftertaste of cigarette smoke, highlighting the "sweet" and "mellow" taste characteristics of cigarettes. However, pure DDMP has poor stability and is easily degraded in air and solvents.

[0003] Currently published patents mainly improve the stability of DDMP by synthesizing stable DDMP ester precursor compounds. Through in-depth research, it was found that adding a certain amount of tertiary amine compounds to DDMP can achieve DDMP stability. Summary of the Invention

[0004] The technical problem to be solved by the present invention is to provide a method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, so as to solve the problem that DDMP has poor stability, is easily deteriorated and damaged, and cannot be used as a sweet and fragrant raw material.

[0005] The technical problem to be solved by the present invention is achieved through the following technical solutions:

[0006] A method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one is provided, wherein the stabilization method comprises contacting DDMP with at least one tertiary amine compound having the structural formula:

[0007]

[0008] Wherein, R1 is methyl, ethyl or phenyl; R2 is phenyl or hydrogen.

[0009] Preferably, the contact between the DDMP and the tertiary amine compound is carried out in the presence of a solvent.

[0010] Preferably, the solvent is any one of water, ethanol or propylene glycol.

[0011] Preferably, the molar ratio of the tertiary amine compound to the DDMP is (0.01-0.1):1.

[0012] Preferably, the temperature condition for contacting the tertiary amine compound with the DDMP is 10-40°C.

[0013] A stabilized sweet and fragrant raw material composition comprises a tertiary amine compound, DDMP and a solvent.

[0014] Preferably, the solvent is any one of water, ethanol or propylene glycol.

[0015] The invention discloses an application of a tertiary amine compound in improving the stability of DDMP.

[0016] Preferably, the tertiary amine compound has the structural formula:

[0017]

[0018] Wherein, R1 is methyl, ethyl or phenyl; R2 is phenyl or hydrogen.

[0019] The above technical solution of the present invention has the following beneficial effects:

[0020] The present invention provides a method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one. DDMP is almost completely degraded after 180 days of storage. However, after adding a tertiary amine compound, degradation is reduced to a maximum of 8% within 180 days. This method successfully addresses the problem of DDMP's poor stability, prone to deterioration and damage, and unsuitable use as a sweet and flavorful raw material. The stabilized sweet and flavorful raw material composition of the present application is more effective and stable. DETAILED DESCRIPTION

[0021] Various exemplary embodiments of the present invention will now be described in detail. It should be noted that the relative arrangement of components and steps, numerical expressions and numerical values ​​set forth in these embodiments do not limit the scope of the present invention unless otherwise specifically stated.

[0022] Example 1

[0023] 144 mg of DDMP (1.0 mmol) was dissolved in 100 mL of ethanol. The DDMP ethanol solution was divided equally into two groups, designated a control group and an experimental group. Tertiary amine compound I (0.05 mmol) was added to the experimental group, while the control group remained untreated. Both control and experimental solutions were maintained at 25°C. Gas chromatography was used to quantitatively analyze the DDMP content in both solutions over time. The control group showed nearly complete degradation after 180 days at 25°C, while the experimental group, after adding tertiary amine compound I, showed only 4% degradation over 180 days. The results are shown in Table 1.

[0024] Wherein, the structure of tertiary amine compound I is:

[0025]

[0026] Table 1

[0027]

[0028] Example 2

[0029] 144 mg of DDMP (1.0 mmol) was dissolved in 100 mL of water. The DDMP aqueous solution was divided equally into two groups, designated a control group and an experimental group. DDMP and tertiary amine compound II (0.005 mmol) were added to the experimental group, while the control group remained untreated. The control and experimental group solutions were then incubated at 30°C. Gas chromatography was used to quantitatively analyze the DDMP content in the two solutions over time. After 180 days at 30°C, the control group showed complete degradation of DDMP, while the experimental group, after adding tertiary amine compound II, showed only 8% degradation over 180 days. The results are shown in Table 2.

[0030] Among them, the structure of tertiary amine compound II is:

[0031]

[0032] Table 2

[0033]

[0034] Example 3

[0035] 144 mg of DDMP (1.0 mmol) was dissolved in 100 mL of propylene glycol. The DDMP-propylene glycol solution was divided equally into two groups, designated a control group and an experimental group. A tertiary amine compound III (0.025 mmol) was added to the experimental group, while the control group remained untreated. The control and experimental group solutions were then incubated at 40°C. Gas chromatography was used to quantitatively analyze the DDMP content in the two solutions over time. The control group showed nearly complete degradation after 180 days at 40°C, while the experimental group, after adding the tertiary amine compound, showed only 6% degradation over 180 days. The results are shown in Table 3.

[0036] Among them, the structure of tertiary amine compound III is:

[0037]

[0038] Table 3

[0039]

[0040] Although the present invention has been disclosed above by way of embodiments, they are not intended to limit the present invention. Any person skilled in the art may make various choices and modifications without departing from the spirit and scope of the present invention. Therefore, the scope of protection of the present invention is defined by the claims and their equivalents.

Claims

1. A method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, characterized in that: The stabilization method is to contact 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one with at least one tertiary amine compound, wherein the tertiary amine compound has the structural formula: ； Wherein, R1 is methyl, ethyl or phenyl; R2 is phenyl or hydrogen.

2. The method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one according to claim 1, characterized in that: The 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one and the tertiary amine compound are contacted in the presence of a solvent.

3. The method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one according to claim 2, characterized in that: The solvent is any one of water, ethanol or propylene glycol.

4. The method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one according to claim 2, characterized in that: The molar ratio of the tertiary amine compound to the 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one is (0.01-0.1):

1.

5. The method for stabilizing 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one according to claim 2, characterized in that: The temperature condition for contacting the tertiary amine compound with the 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one is 10-40°C.

6. A stabilized sweet and fragrant raw material composition, characterized in that The composition comprises 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, a tertiary amine compound and a solvent, wherein the structural formula of the tertiary amine compound is: ； Wherein, R1 is methyl, ethyl or phenyl; R2 is phenyl or hydrogen.

7. The stabilized sweet and fragrant raw material composition according to claim 6, characterized in that The solvent is any one of water, ethanol or propylene glycol.

8. Use of a tertiary amine compound in improving the stability of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one, wherein the tertiary amine compound has the structural formula: ； in, R1 is methyl, ethyl or phenyl; R2 is phenyl or hydrogen.

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