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Preparation of neohesperidin dihydrochalcone

A technology for the enzymatic hydrolysis of hesperidin dihydrochalcone and hesperidin dihydrochalcone, which is applied to the preparation of sugar derivatives, chemical instruments and methods, sugar derivatives, etc., which can solve the problem of high cost and achieve step-by-step Simple, low production cost, simple refining steps

Inactive Publication Date: 2018-01-19
LIANYUAN KANGLU BIOLOGICAL TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention provides a preparation method of new methyl hesperidin dihydrochalcone to solve the technical problem of using neohesperidin as raw material and high cost in the synthesis of new methyl hesperidin dihydrochalcone

Method used

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  • Preparation of neohesperidin dihydrochalcone
  • Preparation of neohesperidin dihydrochalcone
  • Preparation of neohesperidin dihydrochalcone

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preparation example Construction

[0035] The preferred embodiment of the present invention provides a kind of preparation method of new methyl hesperidin dihydrochalcone, comprising the following steps:

[0036] Hesperidin is hydrogenated to synthesize hesperidin dihydrochalcone.

[0037] Hesperetin dihydrochalcone is enzymatically hydrolyzed to produce hesperetin dihydrochalcone.

[0038] React hesperetin dihydrochalcone with neohesperidose or its analogues to obtain neomethylhesperidin dihydrochalcone.

[0039] The synthetic route is as follows:

[0040]

[0041] Hesperidin is hydrogenated to synthesize hesperidin dihydrochalcone, which can be reduced under the condition of stannous chloride, oxalic acid, potassium borohydride, sodium borohydride as reducing agent, or under the condition of protective gas and catalyst Next, direct hydrogen reduction. Hesperetin dihydrochalcone is converted into hesperetin dihydrochalcone by enzymatic hydrolysis reaction, which has obvious advantages compared with addin...

Embodiment 1

[0060] Hesperidin 98% 5kg, dissolve with 50L concentration of 10% sodium hydroxide solution, feed nitrogen as protective gas, catalyst Pd / C dosage is 500g, feed hydrogen under normal temperature and pressure, stir while adding, reaction time For 8 hours, the stirring speed is 800 / r·min-1. After the reaction, recover the catalyst, adjust the pH to 6, add 1 kg of activated carbon, stir for 1.5 hours, filter, and place the filtrate at 4°C for 12 hours to crystallize, recrystallize the coarse crystals with water, and dry to obtain hesperidin dihydrochar Ketone 4.9kg, content 98.5%, stir hesperidin dihydrochalcone with 50 times the amount of water evenly, add hesperidinase 50g, heat to 50 degrees, keep warm for 24h, filter and dry to obtain hesperetin dihydrochalcone Ketone 2.4kg, content 98.6%, stir hesperetin dihydrochalcone with 50 times the amount of water, add 2.5kg new hesperidose, 50g galactosyltransferase, react at 60 degrees for 24h, pass cooling water to stir and analyze ...

Embodiment 2

[0062] Hesperidin 98% 5kg is dissolved in 5% sodium hydroxide solution with 50L concentration, feeds nitrogen as protective gas, catalyst skeleton nickel consumption is 1000g, feeds hydrogen under normal temperature and pressure, stirs while adding, and the reaction time is For 12 hours, the stirring speed was 1000 / r·min-1. After the reaction is over, recover the catalyst, adjust the pH to 5.5, add 500g of activated carbon, stir for 2 hours, filter, put the filtrate at 8°C for 15 hours to crystallize, recrystallize the coarse crystals with water, and dry to obtain hesperidin dihydrochar Ketone 4.5kg, content 98.3%, stir hesperidin dihydrochalcone with 60 times the amount of water evenly, add hesperidinase 60g, heat to 55 degrees, keep warm for 24h, filter and dry to obtain hesperetin dihydrochalcone Ketone 2.2kg, content 98.4%, stir hesperetin dihydrochalcone with 60 times the amount of water, add 2.2kg new hesperidose, 60g glucotransferase, react at 65 degrees for 24 hours, p...

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Abstract

The invention discloses a preparation method of neohesperidin dihydrochalcone. The method comprises the steps of: subjecting hesperidin to hydrogenation synthesis of hesperidin dihydrochalcone, conducting enzymolysis on the hesperidin dihydrochalcone to generate hesperetin dihydrochalcone, and reacting the hesperetin dihydrochalcone with neohesperidose or analogue thereof to obtain the neohesperidin dihydrochalcone. The preparation method of neohesperidin dihydrochalcone adopts hesperidin as the raw material, substantial hesperidin exists in most citrus fruits, the extraction and refining steps are simple, and the price is only 1 / 10 that of neohesperidin. The method provided by the invention for the first time utilizes hesperidin for hydrogenation synthesis of hesperidin dihydrochalcone, then performs enzymolysis to produce hesperetin dihydrochalcone, and then carries out contact reaction with neohesperidose to obtain neohesperidin dihydrochalcone. The synthesis method has the advantages of simple steps and low raw material price, thus greatly reducing the production cost.

Description

technical field [0001] The invention relates to the field of food additive synthesis, in particular to a preparation method of new methyl hesperidin dihydrochalcone. Background technique [0002] In recent years, neomethyl hesperidin dihydrochalcone (NHDC) has become one of the most attractive sweeteners. As early as 1963, Horowitz discovered that it has a strong sweetness, which is about 100% compared with sucrose. 1500-1800 times higher, with a refreshing taste and long-lasting aftertaste, without the unpleasant feeling of saccharin or stevia after use. What's even more commendable is that NHDC has an excellent taste-improving effect, coupled with its characteristics of a slightly later sweetness and a longer duration. Variety, can be used in the food industry. Therefore, NHDC is used as a unique additive in combination with other sweeteners to improve, enhance and overall improve the taste of food and beverages, and has an excellent effect of shielding bitterness. This...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00C12P7/26
Inventor 肖业成魏有何
Owner LIANYUAN KANGLU BIOLOGICAL TECH CO LTD
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