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Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof

A technology of ionol and diester carbonate, which is applied in the field of tobacco, can solve the problems of loss of fragrance, uneven release of fragrance, easy loss, etc., and achieve the effects of slowing down changes, comfortable and harmonious fragrance, and slowing down volatilization

Inactive Publication Date: 2014-05-07
CHINA TOBACCO CHUANYU IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, most of the flavoring agents used in cigarette flavoring are compounds with low molecular weight, low boiling point, and strong volatility, which have disadvantages such as easy loss during high-temperature processing, easy volatilization and loss of flavor during storage, and uneven flavor release during smoking.

Method used

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  • Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof
  • Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof
  • Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: Synthesis of chloroformic acid-β-ionyl ester

[0036] Add 2000ml CH to the reaction flask 2 Cl 2 and bis(trichloromethyl)carbonate 129g (0.44mol), stirred at room temperature until the solid was completely dissolved, put the reaction bottle in an ice-salt bath, cooled to -10°C, added β-ionol 1.28mol, completely dissolved Finally, add 200ml of pyridine dropwise, control the drop rate, and keep the temperature of the reaction solution at 0-5°C. After dropping, the reaction solution is naturally warmed to room temperature, and the reaction is stirred overnight to obtain the dichloroformic acid-β-ionyl dichloride The methane solution can be used in the next step reaction without purification, and the yield is quantitative.

Embodiment 2

[0037] Embodiment 2: Synthesis of chloroformic acid-β-ionyl ester

[0038]The operation process is the same as in Example 1, except that bis(trichloromethyl) carbonate is replaced with trichloromethyl chloroformate, pyridine is replaced with sodium bicarbonate, CH 2 Cl 2 Substitute toluene to obtain a toluene solution of chloroformic acid-β-ionyl ester, which can be used in the next reaction without purification, and the yield is quantitative.

Embodiment 3

[0039] Example 3: Preparation of 3,6-two-O-β-ionol carbonyl-D-glucopyranose carbonate (Compound I)

[0040]

[0041] Take 0.15 mol of the chloroformic acid-β-ionol ester dichloromethane solution prepared in Example 1, and add dropwise 9.7 g (0.05 mol) of D-glucosylmethyl glycoside and 20.2 g of triethylamine that have been cooled to -5 to 0°C. g (0.20mol) and 100ml of dichloromethane, stirred at room temperature for 12h, after the reaction, the solid was filtered out, the filtrate was evaporated under reduced pressure to remove the solvent, the residue was dissolved in 200ml of dichloromethane, and 40ml of 20% hydrochloric acid aqueous solution was added. , stirred at room temperature for 2h, the organic layer was washed successively with 50ml of saturated aqueous sodium carbonate solution and 50ml of saturated brine, and the obtained dichloromethane solution was washed with anhydrous Na 2 SO 4 Dry, filter, evaporate dichloromethane under reduced pressure, and purify the r...

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PUM

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Abstract

The invention relates to cigarette humectants and discloses a monosaccharide beta-ionol carbonate diester compound, and also discloses a preparation method of the compound and an application of the compound in the cigarette humectant, wherein the moisture retention effect, the moistureproof effect, the slow-release spice effect of the compound as the cigarette humectant are tested. Based on the test, the monosaccharide beta-ionol carbonate diester compound has the moisture retention capability on the cigarettes and has the functions of increasing redolence, uniformly releasing the redolence and improving the sensory quality of the cigarettes. In FORMULA shown in the description, O-R-O represents residue of C5 monosaccharide or C6 monosaccharide; and two beta-ionol carbonate ester structural units are arranged at any two proper positions of the C5 or C6 monosaccharide.

Description

technical field [0001] The invention belongs to the technical field of tobacco, and relates to a class of monosaccharide ester cigarette humectants, in particular to monosaccharide β-ionol carbonate diester compounds, a preparation method thereof and its use as a moisturizing agent with moisturizing properties and flavor-increasing and slow-release spices The application of new cigarette humectants. Background technique [0002] Flavor and moisturization are closely related to cigarette quality. "Tobacco Industry "Eleventh Five-Year" Science and Technology Plan" and "Tobacco Industry Medium- and Long-Term Science and Technology Development Plan (2006-2020)" clearly pointed out that the research on technology of increasing flavor and moisturizing is the main direction of technology research and innovation in the industry in the next few years one. [0003] An ideal humectant should have both physical moisturizing and sensory moisturizing functions. Physical moisturizing me...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/12C07H1/00A24B15/34
Inventor 戴亚沈怡邓勇孙玉峰桑志培
Owner CHINA TOBACCO CHUANYU IND
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