Monosaccharide geraniol carbonate diester compound, preparation method and use thereof

A technology of carbonic diester and geraniol, which is applied in the field of monosaccharide ester cigarette moisturizing agent, new cigarette moisturizing agent, and monosaccharide geraniol carbonic diester compound, can solve the problem of uneven fragrance release, low molecular weight, Loss of aroma and other problems, to achieve the effect of comfortable and harmonious aroma, high safety, and slowing down changes

Inactive Publication Date: 2012-01-04
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 ha...

Method used

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  • Monosaccharide geraniol carbonate diester compound, preparation method and use thereof
  • Monosaccharide geraniol carbonate diester compound, preparation method and use thereof
  • Monosaccharide geraniol carbonate diester compound, preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the synthesis of geraniyl chloroformate

[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 1.28mol of geraniol, and dissolved completely , add 200ml of pyridine dropwise, control the rate of addition, and keep the temperature of the reaction solution at 0-5°C. After the dropwise completion, the reaction solution is naturally warmed to room temperature, stirred and reacted overnight, and the dichloromethane solution of geraniyl chloroformate is obtained. It can be used in the next reaction without purification, and the yield is quantitative.

Embodiment 2

[0037] Embodiment 2: the synthesis of geraniyl chloroformate

[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 geraniyl chloroformate, 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-geraniol carbonyl-D-glucopyranose carbonate (compound I)

[0040]

[0041] Get 0.15 mol of the geraniyl chloroformate dichloromethane solution prepared in Example 1, add dropwise 9.7 g (0.05 mol) of D-glucosylmethyl glycoside and 20.2 g of triethylamine ( 0.20mol) and dichloromethane 100ml mixed solution, stirred at room temperature for 12h, after the reaction was completed, the solid was filtered out, the filtrate was evaporated to remove the solvent under reduced pressure, the residue was dissolved in 200ml of dichloromethane, 40ml of 20% hydrochloric acid aqueous solution was added, and the After stirring 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 residue by silica gel column chromatog...

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PUM

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Abstract

The invention relates to a tobacco humectant, discloses a monosaccharide geraniol carbonate diester compound, and further discloses a preparation method for the monosaccharide geraniol carbonate diester compound. According to the present invention, the effects of humidity preserving, damp proofing, slow perfume releasing and sensory evaluation of the monosaccharide geraniol carbonate diester compound adopted as the tobacco humectant are tested. The test results show that: the monosaccharide geraniol carbonate diester compound provides the humidity preserving property for the tobacco, and has effects of aroma increasing, uniform aroma releasing and improvement of organoleptic quality of the tobacco. In the formula provided by the present invention, O-R-O represents a residue of five-carbon or six-carbon monosaccharide, the two geraniol carbonate structure units are positioned on any two possible locations of the five-carbon or six-carbon monosaccharide.

Description

technical field [0001] The invention belongs to the technical field of cigarettes, and relates to a class of monosaccharide ester cigarette humectants, in particular to monosaccharide geraniol carbonic acid diester compounds, their preparation method and their function of moisturizing and flavoring and slow-release spices Application of new cigarette moisturizer. Background technique [0002] Flavor and moisturization are closely related to cigarette quality. "Eleventh Five-Year Plan for Science and Technology of Cigarette Industry" and "Outline of Mid- and Long-term Science and Technology Development Plan for Cigarette Industry (2006-2020)" clearly point out that the research on flavor-enhancing and moisturizing technology is the main direction of technological research and technological 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 means m...

Claims

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Application Information

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IPC IPC(8): C07H13/12C07H1/00C07C69/96C07C68/02A24B15/30A24B15/32
Inventor 戴亚沈怡邓勇孙玉峰桑志培
Owner CHINA TOBACCO CHUANYU IND
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