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Monosaccharide beta-ionol carbonic acid monoester compound, and preparation method and purpose

A technology of ionol ester and ionol, which is applied in the fields of monosaccharide beta-ionol carbonate monoester, monosaccharide ester cigarette moisturizing agent, 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: 2014-02-26
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 carbonic acid monoester compound, and preparation method and purpose
  • Monosaccharide beta-ionol carbonic acid monoester compound, and preparation method and purpose
  • Monosaccharide beta-ionol carbonic acid monoester compound, and preparation method and purpose

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1: Synthesis of chloroformic acid-β-ionyl ester

[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 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

[0044] Embodiment 2: Synthesis of chloroformic acid-β-ionyl ester

[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 chloroformic acid-β-ionyl ester, which can be used in the next reaction without purification, and the yield is quantitative.

Embodiment 3

[0046] Embodiment 3: Preparation of 3-O-β-ionol carbonyl-D-glucopyranosyl ester (compound I)

[0047]

[0048] Take 0.06 mol of the chloroformic acid-β-ionol ester 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 washed with 5% HCl aqueous solution 25ml , saturated 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-β-ionol carbonyl-D-glucose The crude pyranose ester was purified by silica gel column ch...

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Abstract

The invention discloses a monosaccharide beta-ionol carbonic acid monoester compound and preparation method of the compound, which relate to a cigarette humectant. In addition, the humidity preservation, damp-proof and spice slow release effects of the compound in the application as the cigarette humectant are also tested. Tests show that the monosaccharide beta-ionol carbonic acid monoester compound has the humidity preservation performance on the cigarette and has the effects of increasing the perfume quantity, realizing the uniform perfume release and improving the cigarette sensing quality. In a formula, O-R represents residues of C5 monosaccharide or C6 monosaccharide, and beta-ionol carbonyls are positioned in any possible positions of 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 monoester 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 ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H13/12C07H1/00C07C69/96C07C68/02A24B15/34
CPCY02P20/55
Inventor 戴亚沈怡邓勇孙玉峰桑志培
Owner CHINA TOBACCO CHUANYU IND
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