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Sesquiterpenoids in tobacco and preparing method and application thereof

A technology for sesquiterpenes and compounds, which is applied in the separation/purification of carbonyl compounds, tobacco, tobacco treatment and other directions, can solve the problems of unsatisfactory smoking comfort of finished cigarettes and no relevant reports, and improve the smoking quality of cigarettes. , Soft cigarette smoke, novel structure effect

Active Publication Date: 2015-11-18
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, glycerin, propylene glycol, sorbitol and other polyhydroxy substances are mainly used as humectants in my country’s cigarette industry. The main purpose of humectants is to maintain the moisture content of shredded tobacco during processing and improve the processing resistance of shredded tobacco. However, it is not ideal for the smoking comfort of finished cigarettes. A sesquiterpene compound with the function of improving the smoking quality of cigarettes has been obtained through separation. This compound has not been reported so far. There is no relevant report on the quality of suction

Method used

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  • Sesquiterpenoids in tobacco and preparing method and application thereof
  • Sesquiterpenoids in tobacco and preparing method and application thereof
  • Sesquiterpenoids in tobacco and preparing method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] A sesquiterpenoid C 15 h 20 o 2 The preparation method specifically comprises the following steps:

[0032] (1) Preparation of tobacco extract extract: use tobacco leaves as raw material, pulverize or cut the tobacco leaves into small sections, soak and extract the tobacco leaves 4 times with the first solvent, each time for 54 hours, combine the extracts, filter and concentrate to obtain The tobacco extract extract; wherein the first solvent is a mixture of an organic solvent selected from methanol, ethanol or acetone and water, when the first solvent is a mixture of methanol or ethanol and water, wherein methanol or ethanol Accounting for 95wt% of the first solvent, when the first solvent is a mixture of acetone and water, wherein acetone accounts for 70wt% of the first solvent; and the first solvent:tobacco=3:5, weight ratio;

[0033] (2) Silica gel column chromatography: after dissolving the second solvent selected from pure methanol, pure ethanol or pure acetone w...

Embodiment 2

[0037] The tobacco samples used were from Yuxi, Yunnan, and the variety was Yuxi K326. Sampling 2.0 kg of tobacco leaves and pulverizing them, extracting 5 times with 95% methanol for 24 hours each time, combining the extracts, filtering, and concentrating under reduced pressure to obtain 105 g of tobacco extract extract. After dissolving the above-mentioned tobacco extract extract with pure methanol of 2.0 weight multiples, mix the sample with 100 mesh thick silica gel of 120g, then mix with 0.6kg of 160 mesh silica gel and carry out silica gel column chromatography with a volume ratio of 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2 chloroform-acetone gradient elution, TLC monitoring Merge the same fractions to get 8 fractions , wherein the chloroform-acetone eluted part with a volume ratio of 8:2 was separated by Agilent 1100 semi-preparative high performance liquid chromatography, with 55% methanol as mobile phase, ZorbaxSB-C18 (21.2×250mm, 5μm) preparative column It is the sta...

Embodiment 3

[0040] The tobacco samples used were from Dali, Yunnan, and the variety was Yunyan 200. Sampling 3.5 kg of tobacco leaves and chopping them up, extracting 4 times with 95% ethanol for 48 hours each time, combining the extracts, filtering, and concentrating under reduced pressure to obtain 250 g of tobacco extract extract. The above-mentioned tobacco extract extract is dissolved with its 2.0 weight times of pure methanol and mixed with 250g of 80 mesh thick silica gel, then mixed with 1.2kg of 200 mesh silica gel and then packed into a column for silica gel column chromatography, with a volume ratio of 1:0, 20:1, 9:1, 8:2, 7:3, 6:4, 1:1, 1:2 chloroform-acetone gradient elution, TLC monitoring Merge the same fractions to get 8 fractions , wherein the chloroform-acetone eluted part with a volume ratio of 8:2 was separated by Agilent 1100 semi-preparative high performance liquid chromatography, with 55% methanol as mobile phase, ZorbaxSB-C18 (21.2×250mm, 5μm) preparative column I...

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Abstract

The invention discloses sesquiterpenoids novel in structure. The sesquiterpenoids is named as (2R, 3S)-2,3-dihydro-3-hydroxyl-6-isopropyl-2,5,7-trimethyl indene-1-ketone, the molecular formula is C15H20O2, and the sesquiterpenoids has the structure shown in the specification. The invention further discloses preparing method and application of the sesquiterpenoids. It is identified by the experiment that the sesquiterpenoids has the function of improving the smoke quality of cigarettes. Meanwhile, the sesquiterpenoids is matched with humectants according to a proper proportion, the well physical and sense organ moistening functions on the cigarettes are achieved, and the sesquiterpenoids has the effects of softening the smoke of the cigarettes, improving the mellow and full feeling of the smoke of the cigarettes and comfort and making the smoke of the cigarettes being fragrant. Please see the structural formula in the specification.

Description

technical field [0001] The invention belongs to the technical field of tobacco chemistry, in particular to a sesquiterpene compound extracted from tobacco for the first time. At the same time, the invention also relates to the preparation method of the compound and its use in improving the smoking quality of cigarettes. Background technique [0002] Tobacco is the plant with the most complex chemical composition in the world, and its secondary metabolites are very rich. After decades of research, more than 3,000 monomeric chemical substances have been identified from tobacco, and many components have not yet been identified. come out. Although smoking is widely recognized as harmful to health, tobacco still has a strong appeal to thousands of consumers. In addition to the addictive properties of nicotine, the rich flavor substances in tobacco also play an important role. [0003] Sesquiterpenes are natural terpenoids with 15 carbon atoms in the molecule. Sesquiterpenoids ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/747C07C45/78C07C45/79A24B15/34
CPCA24B15/34C07C45/78C07C45/79C07C49/747
Inventor 刘春波张天栋申钦鹏赵伟周博赵英良张凤梅何沛司晓喜王晋杨光宇刘志华苏钟璧缪明明陈永宽
Owner CHINA TOBACCO YUNNAN IND
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