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Monosaccharide alpha-ionol carbonic acid di-ester compound as well as preparation method and application thereof

A technology of carbonic diester and ionol, which is applied in the field of monosaccharide ester cigarette moisturizing agent, monosaccharide α-ionol carbonic diester compound and new cigarette moisturizing agent, and can solve the problem of loss of flavor, uneven flavor release, etc. Easy to lose and other problems, to achieve the effect of slowing down changes, comfortable and harmonious aroma, 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 alpha-ionol carbonic acid di-ester compound as well as preparation method and application thereof
  • Monosaccharide alpha-ionol carbonic acid di-ester compound as well as preparation method and application thereof
  • Monosaccharide alpha-ionol carbonic acid di-ester 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-α-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 solids were completely dissolved, put the reaction bottle in an ice-salt bath, cooled to -10°C, added α-ionol 1.28mol, completely After dissolving, add 200ml of pyridine dropwise, control the rate of addition, and keep the temperature of the reaction solution at 0-5°C. After dropping, the reaction solution is naturally warmed to room temperature, and stirred overnight to obtain dichloroformic acid-α-ionyl ester. Chloromethane 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-α-ionyl ester

[0038]The operation process is the same as in Example 1, except that bis(trichloromethyl)carbonate diester is replaced with trichloromethyl chloroformate, and pyridine is replaced with sodium bicarbonate, CH 2 Cl 2 Substitute toluene to obtain a toluene solution of chloroformic acid-α-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-di-O-α-ionol carbonyl-D-glucopyranose carbonate (Compound I)

[0040]

[0041] Take 0.15 mol of the chloroformic acid-α-ionol ester methylene chloride solution prepared in Example 1, and add dropwise 9.7 g (0.05 mol) of D-glucosylmethyl glycoside, 20.2 g of triethylamine, which has been cooled to -5 to 0° C. g (0.20mol) and dichloromethane 100ml mixed solution, stirred at room temperature for 13h, after the reaction, filtered out solid, the filtrate was evaporated to remove the solvent under reduced pressure, the residue was dissolved in 200ml of dichloromethane, and 40ml of 20% hydrochloric acid aqueous solution was added , stirred at room temperature for 1.5h, the organic layer was washed successively with saturated aqueous sodium carbonate solution 50ml and saturated brine 50ml, and the obtained dichloromethane solution was washed with anhydrous Na 2 SO 4 Dry, filter, dichloromethane is distilled off under reduced pressure, and the r...

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Abstract

The invention relates to a cigarette humectant and discloses a monosaccharide alpha-ionol carbonic acid di-ester compound, and a preparation method thereof, and humidity keeping, damp preventing and spice slowly releasing effects of the compound as the cigarette humectant are proved through tests. The tests show that the monosaccharide alpha-ionol carbonic acid di-ester compound has humidity keeping performance for cigarettes and has the functions of increasing the fragrance, uniformly releasing fragrance and improving the aesthetic quality of the cigarettes. In the formula shown in the description, O-R-O is a residue of five-carbon monosaccharide or six-carbon monosaccharide; and two alpha-ionol carbonic acid ester structural units are arranged on any two possible positions of the five-carbon monosaccharide or the six-carbon 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 α-ionol carbonate diester compounds, a preparation method thereof and its use as a moisturizing agent with moisturizing properties and flavor-enhancing 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 mea...

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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