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Mono-pentose or hexose-(E)-3-(furan-2-yl) acrylic acid diester compound and preparation method and use thereof

A technology of diester acrylate and six-carbon monosaccharide, which is applied in the field of tobacco, can solve the problems of unsatisfactory moisture content and smoking comfort of finished cigarettes, enhanced dryness and irritation, and greater influence of tobacco. Conducive to the effects of smoking safety, comfortable and harmonious aroma, and easy promotion and application

Inactive Publication Date: 2013-01-30
CHINA TOBACCO CHUANYU IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the humectants used in the production of cigarettes in my country are mainly glycerin, propylene glycol, xylitol and other polyhydroxy substances, which mainly rely on their absorption of moisture in the environment to keep the shredded tobacco moist and play a moisturizing role, which belongs to one-way moisturizing Although this kind of humectant can maintain the moisture content of cut tobacco during processing and improve the processing resistance of cut tobacco, its effect of maintaining the moisture content of finished cigarettes and improving smoking comfort is not really satisfactory
In addition, since this type of polyhydric humectant has no moisture-proof effect, the moisture content of tobacco treated with this type of humectant is greatly affected by the ambient temperature and humidity, that is, in a dry environment, tobacco is easy to lose moisture and cause it to dry. The sensation and irritation are enhanced, and tobacco is easy to absorb moisture in a humid and warm environment, causing it to mold and deteriorate

Method used

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  • Mono-pentose or hexose-(E)-3-(furan-2-yl) acrylic acid diester compound and preparation method and use thereof
  • Mono-pentose or hexose-(E)-3-(furan-2-yl) acrylic acid diester compound and preparation method and use thereof
  • Mono-pentose or hexose-(E)-3-(furan-2-yl) acrylic acid diester compound and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Preparation of 3,6-di-[(2E)-3-(furan-2-yl)-2-acryloyl]-D-glucopyranosyl ester (compound I):

[0035] Add 16.58 g (0.12 mol) of (E)-3-(furan-2-yl)acrylic acid, 28.56 g (0.24 mol) of thionyl chloride and 200 ml of chloroform in sequence in the reaction flask, and heat up to 50-55°C to stir the reaction After 3 h, after the reaction, the solvent and excess thionyl chloride were distilled off under reduced pressure, the residue was dissolved in 100 ml of dichloromethane, and 9.7 g of D-glucosylmethyl glycoside which had been cooled to -5 ~ 0 °C was added dropwise (0.05 mol), triethylamine 20.2g (0.20 mol) andN , N - In 100 ml of dimethylformamide mixed solution, stirred at 15-30°C for 20 h, after the reaction, the solid was precipitated by filtration, the filtrate was evaporated under reduced pressure to remove the solvent, the residue was dissolved in 200 ml of dichloromethane, and 10% Hydrochloric acid aqueous solution 40 ml, stirred at room temperature for 2 h, the orga...

Embodiment 2

[0037] Preparation of 2,3-di-[(2E)-3-(furan-2-yl)-2-acryloyl]-D-glucopyranosyl ester (compound II):

[0038] The operation process is the same as in Example 1, except that thionyl chloride is replaced with phosphorus trichloride, and triethylamine is replaced with pyridine, N , N -Dimethylformamide is replaced by ethyl acetate, and D-glucose methyl glycoside is replaced by 4,6-O-isopropylidene-D-glucose methyl glycoside to obtain 2,3-di-[(2E)- 3-(Furan-2-yl)-2-acryloyl]-D-glucopyranosyl ester, yield 64.5%; HR-TOFMS (+Q) m / z : 421.1156 ( [C 20 h 20 o 10 +H] + Calculated value: 421.1153 ).

Embodiment 3

[0040] Preparation of 2,3-bis-[(2E)-3-(furan-2-yl)-2-acryloyl]-D-galactopyranose ester (compound III):

[0041] Operation process is the same as embodiment 1, just uses thionyl chloride a -Chloro- N,N,2 -Trimethyl allylamine is replaced, triethylamine is replaced by pyridine, N , N -Dimethylformamide is replaced by tetrahydrofuran, and D-glucosylmethyl glycoside is replaced by 4,6-O-isopropylidene-D-galactosylmethyl glycoside to obtain 2,3-di-[(2E)-3 -(furan-2-yl)-2-acryloyl]-D-galactopyranose ester, yield 71.8%; HR-TOFMS (+Q) m / z : 421.1145 ( [C 20 h 20 o 10 +H] + Calculated value: 421.1153 ).

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Abstract

The invention discloses a mono-pentose or hexose-(E)-3-(furan-2-yl) acrylic acid diester compound and a preparation method and use thereof, and relates to a monose diester tobacco humectant. According to the invention, a novel mono-pentose or hexose-(E)-3-(furan-2-yl) acrylic acid diester compound shown as formula (1) is prepared by chemical synthesis method, and humidification, moisture-proof and fragment slow-releasing effects of the compound used as tobacco humectant are tested. The test results show that such monose (E)-3-(furan-2-yl) acrylic acid diester compounds have humidification, moisture-proof and fragment slow-releasing effects for tobacco and become novel tobacco humectants having bidirectional humidification and fragment slow-releasing effect; (1) in the formula (1), R represents a residue of mono-pentose or mono-hexose, and two (E)-3-(furan-2-yl) acryloyls can be positioned at any two possible locations of the mono-pentose or mono-hexose.

Description

technical field [0001] The invention belongs to the field of tobacco technology, and relates to a class of monosaccharide diester tobacco humectants, in particular to five-carbon or six-carbon monosaccharide-(E)-3-(furan-2-yl)acrylic acid diester compounds, its Preparation method and use. Background technique [0002] The moisture retention performance of cigarettes is closely related to the quality of cigarettes, and the research on flavor enhancement and moisture retention technology will be one of the main directions of scientific and technological research and technological innovation in my country's tobacco industry in the next few years. At present, the humectants used in the production of cigarettes in my country are mainly glycerin, propylene glycol, xylitol and other polyhydroxy substances, which mainly rely on their absorption of moisture in the environment to keep the shredded tobacco moist and play a moisturizing role, which belongs to one-way moisturizing Althou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/04C07H1/00A24B15/40
Inventor 戴亚沈怡周容孙玉峰李东亮汪长国马扩彦
Owner CHINA TOBACCO CHUANYU IND
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