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Clathrate compound of anionic open-loop cucurbituril and vanillin spice as well as preparation method and application of clathrate compound

An anion ring-opening and vanillin technology, which is applied in the fields of tobacco, cosmetics, food and nutritional health products, flavors and fragrances, can solve the problems of poor water solubility and limit applications, and achieve improved controllable release performance, high purity, and broad application prospects Effect

Pending Publication Date: 2022-05-10
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the melon rings have a good rigid structure and stability, most of the melon rings have limited their applications due to their poor water solubility.

Method used

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  • Clathrate compound of anionic open-loop cucurbituril and vanillin spice as well as preparation method and application of clathrate compound
  • Clathrate compound of anionic open-loop cucurbituril and vanillin spice as well as preparation method and application of clathrate compound
  • Clathrate compound of anionic open-loop cucurbituril and vanillin spice as well as preparation method and application of clathrate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 1.453g (1mmol) anionic ring-opening cucurbita ring a (R=(CH 2 ) n SO 3 A, A=H, n=3) Dissolve the solid powder in 15ml, heat and stir at 30°C for 30min to dissolve completely, stop heating, let the solution cool to room temperature, and then directly add 0.332g (2mmol) of ethyl vanillin to Anion ring-opening melon ring a (R=(CH 2 ) n SO 3 A, A=H, n=3) in an aqueous solution, stirred vigorously at 25°C for 48 hours, filtered to remove insoluble matter, and the filtrate was freeze-dried to obtain the anion-opened melon ring a(R=(CH 2 ) n SO 3 A, A=H, n=3) and the target product of ethyl vanillin clathrate, the yield is 98%.

[0041] Such as figure 1 As shown, in the present embodiment, the comparative analysis figure of the proton nuclear magnetic resonance spectrum of the clathrate: (a) ring-opening melon ring a (R=(CH 2 ) n SO 3 A, A=H, n=3); (b) open ring melon ring a (R=(CH 2 ) n SO 3 A, A=H, n=3) inclusion complex with ethyl vanillin; (c) ethyl vanillin....

Embodiment 2

[0044] 1.341g (1mmol) anionic ring-opening cucurbit ring a (R=(CH 2 ) n SO 3 A, A=H, n=1) Dissolve the solid powder in 15ml, heat and stir at 60°C for 60min to dissolve completely, then stop heating, let the solution cool to room temperature, then dissolve 0.456g (3mmol) of vanillin in 5ml of ethanol Added to the open ring melon ring a (R=(CH 2 ) n SO 3 A, A=H, n=1) in an aqueous solution, stirred vigorously at 50°C for 72 hours, filtered to remove insoluble matter, and the filtrate was freeze-dried to obtain an anion-opened melon ring I (R=(CH 2 ) n SO 3 A, A=H, n=1) and the target product of vanillin clathrate, the yield is 97%.

[0045] Such as image 3 As shown, in this embodiment, the X-ray diffraction spectrum of the clathrate is compared and analyzed. (a) ring-opening melon ring a (R=(CH 2 ) n SO 3 A, A=H, n=1); (b) ring-opening melon ring a (R=(CH 2 ) n SO 3 A, A=H, n=1) inclusion complex with vanillin; (c) vanillin. After forming the clathrate, open th...

Embodiment 3

[0047] 1.541g (1mmol) anionic ring-opening cucurbit ring a (R=(CH 2 ) n SO 3 A, A=Na, n=3) Dissolve the solid powder in 15ml, heat and stir at 50°C for 45min to dissolve completely, then stop heating, let the solution cool to room temperature, and then directly add 0.830g (5mmol) of ethyl vanillin into Anion ring-opening melon ring a (R=(CH 2 ) n SO 3 A, A=Na, n=3) in an aqueous solution, stirred vigorously at 20°C for 36 hours, filtered to remove insoluble matter, and the filtrate was concentrated and dried under reduced pressure to obtain the anion-opened cucurbita ring a(R=(CH 2 ) n SO 3 A, A=Na, n=3) and the target product of ethyl vanillin clathrate, the yield is 98%.

[0048] Such as Figure 4 As shown, the thermal release analysis diagram of the clathrate in this embodiment. The clathrates are relatively stable at 25°C, and only a small amount of ethyl vanillin is released from the clathrate during the test; at 60°C, the thermal release efficiency of ethyl vani...

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PUM

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Abstract

The invention discloses a clathrate compound of anionic ring-opening cucurbituril and vanillin spice as well as a preparation method and application of the clathrate compound. According to the clathrate compound, the vanillin spice and the anionic ring-opening cucurbituril are subjected to clathration reaction. The preparation method comprises the following steps: adding anion open-loop cucurbituril solid powder into a reaction kettle, adding a proper amount of pure water into the reaction kettle, and heating and stirring until the anion open-loop cucurbituril solid powder is completely dissolved; after dissolving, stopping heating, cooling the solution to room temperature, directly adding vanillin perfume or adding the vanillin perfume into the aqueous solution of the anion open-loop cucurbituril after dissolving the vanillin perfume with an organic solvent, and stirring; and filtering, and drying the filtrate to obtain a target product of the inclusion compound of the anion open-loop cucurbituril and the vanillin spice. The clathrate compound of the anion open-loop cucurbituril and the vanillin spice prepared by the invention can obviously improve the thermal stability of the vanillin spice, can be applied to the fields of flavors and spices, tobaccos, cosmetics, foods, nutritional health-care products and the like, can realize slow release and controlled release of the vanillin spice, and is more stable and safer.

Description

technical field [0001] The invention relates to the technical fields of flavors and fragrances, tobacco, cosmetics, food and nutritional health products, in particular to a clathrate of anionic ring-splitting cucurbit rings and vanillin-like spices and its preparation method and application. Background technique [0002] Vanillin, also known as vanillin, has a chemical name of 3-methoxy-4-hydroxybenzaldehyde. It has a strong milky taste and is a broad-spectrum spice. It not only exists in natural vanilla and other plants, but also can be synthesized artificially. It is the most widely used spice in the world. It has a wide range of uses: in the food field, it is widely used in various flavored foods that need to increase the milk flavor, such as ice cream, chocolate, candy, cakes, etc., and can also be added to infant formula foods; in daily chemicals, it can be used Used in the deodorization of plastics, rubber and other industrial products; in the cosmetics industry, it c...

Claims

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Application Information

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IPC IPC(8): C07D487/22C07C47/575C07C45/00C11B9/00A61K8/49A61K8/33A24B15/38A24B15/30A23L27/10
CPCC07D487/22C07C47/575C07C45/00C11B9/0061A23L27/10A61K8/33A61K8/4946A24B15/385A24B15/301A23V2002/00
Inventor 殷沛沛杨波王保兴张舒清卢伟周桂园
Owner CHINA TOBACCO YUNNAN IND
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