Flavoring substance for cigarettes, method for preparing flavoring substance and application thereof

A flavoring substance and technology for cigarettes, which is applied in the field of daily chemical industry, can solve the problems of decreased taste, small molecular weight, and large irritation, and achieve the effects of soft and transparent smoke, mellow aftertaste, and improved taste

Active Publication Date: 2017-07-28
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the relatively small molecular weight of commonly used tobacco flavors and fragrances, it is easy to volatilize and lose during daily use, especially when used under high temperature conditions, because it is easy to volatilize when heated at high temperature, and it is easy to cause a large amount of loss, resulting in its application in cigarettes. After fragrance, the fragrance stays for a short time, and problems such as uneven fragrance occur
Therefore, the present invention hopes to utilize the good thermal stability of glycoside flavor precursors, but it can be thermally decomposed to release aroma substances in a high-temperature environment at a certain temperature, so as to solve the problem of weakening the aroma of cigarette products due to harm reduction and tar reduction. Disadvantages such as decreased taste, increased miscellaneous gas and greater irritation

Method used

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  • Flavoring substance for cigarettes, method for preparing flavoring substance and application thereof
  • Flavoring substance for cigarettes, method for preparing flavoring substance and application thereof
  • Flavoring substance for cigarettes, method for preparing flavoring substance and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Preparation of Bromotetraisovaleryl Glucose Ester

[0020]

[0021] Put 0.5mol dry D-glucose into a 500mL round-bottom three-neck flask, add 300m methylene chloride to it, stir and mix evenly, add 3mol isovaleryl chloride and continue stirring for 0.5h, then add 3mol of pyridine dropwise, and continue the reaction for 6h , a brownish-yellow solution was obtained. Pour the reaction solution into a beaker filled with 250 mL of ice water, and stir for about 3 hours. The bottom layer of the beaker gradually becomes viscous, and white crystals gradually precipitate out. The upper liquid was removed, and the crystals were washed with cold water to collect the crystalline compound. The collected compound was dissolved in 300ml of dichloromethane, and the mass percent concentration of 150ml of HBr was added dropwise at 0°C as a 33% HBr acetic acid solution, after the addition was completed, it was raised to room temperature and reacted overnight, poured into a container con...

Embodiment 2

[0023] Preparation of 3-oxo-α-ionol-2,3,4,6-tetra-O-isovaleryl-β-D-glucopyranoside

[0024]

[0025] Bromotetraisovalerylglucose ester (3g, 5mmol), 3-oxo-α-ionol 5mmol were dissolved in a mixed solvent of 25ml toluene and 5ml ether, after adding Ag 2 CO 3 (3.32g, 12mmol) was stirred at reflux for 12.5 hours. The reaction mixture was washed with saturated NaHCO 3 aqueous solution. use CH 2 Cl 2 extraction. The extract was washed with brine and then with MgSO 4 dry. Removal of the solvent gave a residue which was subjected to column chromatography eluting with hexane-ether (2:1) to give the substrate in 80% yield. 1 H NMR (501MHz, CDCl 3 )δ5.77(S,1H),5.70(d,J=8.3Hz,1H),5.59(d,J=9.4Hz,1H),5.54~4.65(m,5H),4.31(d,J=12.5 ,2H),3.76(m,1H),2.80~2.86(m,3H),2,45~2.50(m,4H),2.14~2.27(m,8H),1.71(S,3H),1.31(d , J=8.3Hz, 3H), 0.96~1.2(m, 30H).

Embodiment 3

[0027] A formulation of electronic cigarette liquid containing 3-oxo-α-ionol-2,3,4,6-tetra-O-isovaleryl-β-D-glucopyranoside

[0028] The formula is prepared from the following components in mass percentage:

[0029]

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Abstract

The invention provides a flavoring substance for cigarettes. A structural formula of the flavoring substance is shown. The invention further provides a method for preparing the flavoring substance for the cigarettes. The method includes carrying out reaction by the aid of D-glucose and isovaleryl chloride under alkaline conditions to generate sugar ester; carrying out reaction on the sugar ester and HBr (hydrogen bromide) acetic acid solution to generate bromo-sugar ester; carrying out reaction on the bromo-sugar ester and 3-oxo-alpha-ionol under the catalytic effects of silver carbonate or silver oxide to generate the glycoside flavoring substance for the cigarettes. The flavoring substance and the method have the advantages that taste can be obviously improved, offensive odor of the cigarettes can be effectively concealed, flavor of the cigarettes can be increased, smoke is gentle and can volatile, aroma is exquisite, and aftertaste can be improved and is pure, mild and pleasant.

Description

technical field [0001] The invention belongs to the field of daily chemical industry and relates to a fragrance technology, in particular to a flavoring substance for cigarettes and its preparation method and application. Background technique [0002] With the development of society, people's requirements for health are getting higher and higher, which has led to more stringent and harsh regulations on "harm reduction and tar reduction" of cigarette products. While the requirements for cigarette "harm reduction and coke reduction" are becoming more and more stringent, it also leads to a great decline in the aroma quality of cigarettes. The aroma substances of cigarettes are greatly reduced, and the taste is also reduced. The application of tobacco flavors and fragrances in cigarettes emerged as the times require, and quickly gained widespread attention. However, due to the relatively small molecular weight of commonly used tobacco flavors and fragrances, it is easy to volat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/18C07H1/00A24B3/12A24B15/40
CPCA24B3/12A24B15/403C07H1/00C07H15/18
Inventor 任文博王伟刘清雷刘慧敏
Owner SHANGHAI INST OF TECH
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