Monosaccharide geraniol carbonate monoester compound and preparation method and application thereof

A technology of carbonic acid monoester and geraniol ester, which is applied in the fields of monosaccharide geraniol carbonate monoester compound, novel cigarette moisturizing agent, and monosaccharide ester cigarette moisturizing agent, and can solve the problem of uneven fragrance release and 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: 2012-01-11
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 geraniol carbonate monoester compound and preparation method and application thereof
  • Monosaccharide geraniol carbonate monoester compound and preparation method and application thereof
  • Monosaccharide geraniol carbonate monoester compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: the synthesis of geraniyl chloroformate

[0043] 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

[0044] Embodiment 2: the synthesis of geraniyl chloroformate

[0045] 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

[0046] Example 3: Preparation of 3-O-geraniol carbonyl-D-glucopyranosyl ester (compound I)

[0047]

[0048] Take 0.06 mol of the geraniyl chloroformate dichloromethane solution prepared in Example 1, and add dropwise to 1,2:5,6-di-O-isopropylidene-D- Glucofuranose 0.05mol, triethylamine 0.08mol and dichloromethane 100ml mixed solution, stirred at room temperature for 20h, after the reaction, the reaction solution was transferred to a separatory funnel, and the organic layer was sequentially saturated with 5% HCl aqueous solution 25ml, NaHCO 3 25ml of aqueous solution and 25ml of saturated NaCl aqueous solution, washed with anhydrous NaCl 2 SO 4 Dry, filter, evaporate the solvent under reduced pressure, add 50ml of 70% trifluoroacetic acid aqueous solution to the residue, stir and react at 15-25°C for 3h, evaporate the solvent under reduced pressure, and obtain 3-O-geraniolcarbonyl-D-glucopyridine The crude pyranose ester was purified by silica gel column chromatography ...

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PUM

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Abstract

The invention relates to a cigarette humectant, discloses a monosaccharide geraniol carbonate monoester compound, also discloses a preparation method of the compound, and tests the moisture retention, damp resistance and perfume sustained release effect of the compound as a cigarette humectant. Tests demonstrate that the monosaccharide geraniol carbonate monoester compound has moisture retention performance for tobacco, and has the effect of aroma increase, uniform aroma release, and cigarette sensory quality improvement. In the formula, O-R represent residues of five-carbon monosaccharide or six-carbon monosaccharide; geraniol carbonyl is located at any possible position of the five-carbon or 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 geraniol carbonate monoester 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. "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 means moisturizing, which refers to maintain...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/12C07H1/00C07C69/96C07C68/02A24B15/30A24B15/32
CPCY02P20/55
Inventor 戴亚沈怡邓勇孙玉峰桑志培
Owner CHINA TOBACCO CHUANYU IND
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