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Clathrate compound of hemicucurbit [6] uril and tobacco alkaloid as well as preparation method and application of clathrate compound

A technology of tobacco alkaloids and clathrates, applied in the fields of tobacco, flavors and fragrances, food and medicine, and cosmetics, to achieve the effects of overcoming instability and volatility, high safety, and simple and easy preparation methods

Pending Publication Date: 2022-02-18
KUNMING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The tobacco alkaloid inclusion compounds reported in these patents all use the method of microparticles, microcolloids, gels and C-type semi-cyclic open-ring cucurbituril to increase the sustained release of tobacco alkaloids, and utilize a class of flexible ring-shaped Molecule hemicucurbit[6]urea and tobacco alkaloid undergo inclusion reaction to form a kind of inclusion compound of hemicucurbit[6]urea and tobacco alkaloid, which has not been reported

Method used

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  • Clathrate compound of hemicucurbit [6] uril and tobacco alkaloid as well as preparation method and application of clathrate compound
  • Clathrate compound of hemicucurbit [6] uril and tobacco alkaloid as well as preparation method and application of clathrate compound
  • Clathrate compound of hemicucurbit [6] uril and tobacco alkaloid as well as preparation method and application of clathrate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: 1 mmol of half-gourd [6] is dissolved in 25 ml of distilled water, stirred at 20 ° C to dissolve, and 2 mmol of nicotine was added to a half-gourd [6] urea solution, at 30 ° C The mixture was stirred under conditions for 12 h. After filtration, the insoluble material was removed, and the water was concentrated under reduced pressure at 50 ° C, and the concentrate was 40 ° C to cep the dry and dry to prepher the half of the gourd [6] urea and nicotine, the yield was 96%; Nuclear magnetic resonance spectrum of nicotinic and half gourd [6] urea (R is H) complex ( 1 H NMR) See figure 2 ; By measurement figure 2 middle 1 The change of the H NMR spectrum is evaluated whether the nicotine is contained in the cavity of half a cucurbit [6] urea, the nicotine is formed before and after the mixture 1 H NMR chemical transpares in Table 1, nicotine / half gourd [6] urea coated compared to free nicotine, due to the shielding effect of hemodes [6] urea cavity, H-hhotoma H- 1, 5...

Embodiment 2

[0039] Example 2: 1 mmol of half a gourd [6] is dissolved in 25 ml of methanol, stirred at 20 ° C to dissolve, and 1.5 mmol of nomotic base is added to a half a gourd [6] urea solution, in The mixture was stirred at 20 ° C for 6 days, and the insoluble material was removed, and the methanol was concentrated under reduced pressure at 60 ° C, and the concentrate was evaporated, and the concentrate was concentrated. The yield is 90%. Numeromiometholic and Hurricane [6] urea (R is H) Nuclear magnetic resonance spectrum ( 1 H NMR) See Figure 7 By measuring Figure 7 middle 1 The change of the H NMR spectrum was evaluated whether the nicotin was included in the cavity of the half cucurbit [6] urea. Nicotine and Herrutum [6] urea form a compound before and after 1 H NMR chemical displacement is collected in Table 2; nicotine / half gourd [6] urea coated compared to free nicotine, due to a shielding effect of hemodes [6] urea cavity, H-hhotoma H- 1,5 protons have experienced 0.34 ppm of fi...

Embodiment 3

[0045] Example 3: Take 4 mmol of Halfeit [6] urea (R is C 6 Hide 12The dissolved in 25 ml of DMF, stirred at 20 ° C to dissolve, and 7 mmol of diene nicotine was added to a half a gourd [6] urea solution, stirred at 25 ° C for 23 h, and the DMF was concentrated under reduced pressure at 40 ° C. The concentrate-20 ° C is freeze dry, and the oxytoacid [6] urea and diene nicotine is prepared, and the yield is 97%.

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Abstract

The invention discloses a clathrate compound of hemicucurbit [6] uril and tobacco alkaloid, the clathrate compound contains the tobacco alkaloid and hemicucurbit [6] uril, the molar ratio of the tobacco alkaloid to the hemicucurbit [6] uril is (1-10): 1, the hemicucurbit [6] uril molecule has a hydrophobic cavity, so that the hemicucurbit [6] uril molecule and the tobacco alkaloid form good cavity matching; meanwhile, the electronegativity of the carbonyl group of the hemicucurbit [6] uril molecule interacts with the tobacco alkaloid, so that the binding property of the host and guest substances is enhanced, and the stability and the release property of the tobacco alkaloid can be regulated and controlled; the preparation method of the clathrate compound is simple and easy to implement, mild in condition and suitable for industrial production.

Description

Technical field [0001] The present invention relates to the field of flavor spices, tobacco, cosmetics, food and drugs. Specifically, the new system of tobacco alkaloids and its preparation methods and applications. Background technique [0002] Tobacco alkaloids, basic nitrogen-containing heterocyclic compounds in tobacco, is a group of tacibromatic products, including more than 50 substances, existing in more than 60 different kinds of tobacco, and some components are existing outside tobacco. Plant. Their individual components also exist in certain plants other than tobacco. Tobacco alkaloids mainly have two types of molecular structures, and one is a compound that binds to pyridine and hydrogenated pyrrole, such as nicotine (nicotine), demestinoid skein (nicobial), and demethyl dehydrogenate. Meshnamming), diene nicotin (nicobin), demethyl diene nicotine (Niki), etc .; the other is a compound that binds to pyridine or pyridine or hydrogenated pyridine, such as new smoke Base ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04C07D213/22C07D487/22C11B9/00A24B15/38A61K8/49A23L33/105
CPCC07D401/04C07D213/22C07D487/22C11B9/0092A24B15/38A24B15/283A61K8/4926A23L33/105
Inventor 杨波杜刚周佳伟张亚洲张舒清赵榆林
Owner KUNMING UNIV OF SCI & TECH
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