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Method for producing hexahydrolupulicone

A technology of hexahydrolupulone and lupulone, which is applied in chemical instruments and methods, preparation of organic compounds, separation/purification of carbonyl compounds, etc., can solve the problems of single product and high cost, achieve high product yield, Low production cost and improved purity

Inactive Publication Date: 2010-05-26
XINJIANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention aims to solve the disadvantages of single product and high cost in the production of tetrahydroisohumulone in the prior art that the existing lupulone is usually discarded as a by-product, and provides a new antibacterial and anti-oxidative The compound that is easy to preserve proposes the technical scheme of the present invention

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 1.1 Separation and purification of lupulone

[0022] Dissolve 100g of hop extract (including humulone content of 59.7% and lupulone content of 18.6%) in 50ml of alkaline ethanol aqueous solution (this solution contains 12.5g of KOH), dissolve and let stand for one hour, and separate Remove the insoluble matter in the extract. Dilute the separated alkaline ethanol aqueous solution containing humulone and lupulone with 450ml of distilled water to prepare a mixed solution of humulone and lupulone; then add CO 2 The gas is passed into the mixed solution of humulone and lupulone. When the pH value of the solution reaches about 8.5, the lupulone begins to crystallize out. Stop access to CO 2 , Continue to stir for 40-60 minutes, stand still, filter and separate 22.3 g of the crude lupulone from the solution. The crude lupulone is analyzed by HPLC and the content of lupulone is 75.9%. The crude lupulone was recrystallized once with n-hexane to obtain 16.8 g of the purified lupul...

Embodiment 2

[0028] Use a sterile dropper to suck the inoculum liquid into a sterile petri dish, inject about 15ml of sterilized melted nutrient agar medium, mix and cool and solidify into a plate containing bacteria, and use a small amount of the hexahydrolupulone sample to kill The bacteria’s ethanol is dissolved, and then the sterilized lye with a pH value of 11-13 is used to prepare four series of concentrations of 500ppm, 250ppm, 125ppm, 32ppm, respectively, and the diameter of the inhibition zone for different bacterial species at each concentration is measured. , Observe the antibacterial situation, determine the antibacterial effect and minimum inhibitory concentration.

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Abstract

A process for preparing hexahydrolupulone includes such steps as dissolving the extract of hop in the alkaline aqueous solution of alcohol, separating out humulone and lupulone, filling CO2 gas, separating coarse lupulone recrystallizing in n-hexane, dissolving in reactive medium, adding catalyst Pd / C, filling H2, hydroreacting, filtering, concentrating the filtrate, laying aside, cooling for crystallizing, filtering to obtain coarse hexahydrolupulone, and recrystallizing in n-hexane. It can be used in food for antiseptic, bacteria-suppressing and antioxidizing purposes.

Description

Technical field [0001] The present invention relates to a method for producing hexahydrolupulone. More specifically, the present invention relates to a method for producing hexahydrolupulone. 2 Method for preparing hexahydrolupulone from hop extract. Background technique [0002] When hop extract is used to produce tetrahydroisohumulone, lupulone is usually discarded as a by-product. For example, Chinese Patent Application No. 94100149.0, 200410073602.6, lupulone has very good antibacterial activity, but it is easily oxidized and difficult to store, and the hydrogenated product of lupulone, hexahydrolupulone, not only has very good chemical stability, And still retains very good antibacterial and antioxidant activities. Since the catalytic hydrogenation reaction of lupulone is extremely sensitive to the reaction conditions, the hydrogenation reaction is often accompanied by complicated hydrogenolysis reactions, resulting in a very low yield of hexahydrolupulone, so no commercial...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/78C07C45/62C07C49/743A23L3/00
Inventor 刘玉梅刘奎钫鲍永和陈德军刘玉英
Owner XINJIANG UNIVERSITY