Search

CN-122011060-A - Preparation method of high-purity neohesperidin dihydrochalcone crystal

CN122011060ACN 122011060 ACN122011060 ACN 122011060ACN-122011060-A

Abstract

The invention relates to a preparation method of a high-purity neohesperidin dihydrochalcone crystal, which comprises the following steps of dissolving neohesperidin in an alkaline solution, adding acid and an alcohol solvent for crystallization and purification to obtain the high-purity neohesperidin, generating neohesperidin dihydrochalcone in the presence of an alkaline solution, hydrogen, palladium carbon or Raney nickel, adjusting pH, adding alcohol as a mixed solvent, precipitating at normal temperature to obtain the high-purity neohesperidin dihydrochalcone, and recrystallizing with alcohol/methyl tertiary ether to obtain the neohesperidin dihydrochalcone crystal. The method solves the problem of low purity of neohesperidin dihydrochalcone in the prior art, and the obtained needle crystal of neohesperidin dihydrochalcone has high sweetness, long sweetness duration, high sweet abundance and long aftertaste.

Inventors

  • SONG XUE
  • YUAN JIARU
  • LI BIN
  • LI QIANGQIANG
  • WANG JUNJUN
  • ZHAN JIAN

Assignees

  • 安徽金禾合成材料研究院有限公司
  • 安徽金禾实业股份有限公司

Dates

Publication Date
20260512
Application Date
20251210

Claims (10)

  1. 1. S1, dissolving a neohesperidin raw material by using an alkaline solution, adding an acid and an alcohol solvent at room temperature after complete dissolution, crystallizing at low temperature, and performing suction filtration and drying to obtain the high-purity neohesperidin; S2, generating neohesperidin dihydrochalcone with high purity in the presence of alkali solution, hydrogen, palladium carbon or Raney nickel, adjusting pH to 3-6, adding alcohol as a mixed solvent, and precipitating at normal temperature to obtain the neohesperidin dihydrochalcone with high purity; S3, recrystallizing the high-purity neohesperidin dihydrochalcone with alcohol/methyl tertiary butyl ether to obtain a neohesperidin dihydrochalcone crystal.
  2. 2. The preparation method of the high-purity neohesperidin dihydrochalcone crystal according to claim 1, wherein the alkaline solution used for purifying the neohesperidin in the step S1 is a water solution of triethylamine, potassium carbonate, sodium hydroxide or potassium hydroxide, the concentration of the alkaline solution is 10-30%, and the mass ratio of the neohesperidin to the alkaline solution is 1:2-6.
  3. 3. The method for preparing high-purity neohesperidin dihydrochalcone crystals, according to claim 1, is characterized in that acid used for purifying neohesperidin in the step S1 is hydrochloric acid, sulfuric acid or phosphoric acid, and the molar ratio of the acid to an alkaline solution is 1:0.9-2.5.
  4. 4. The preparation method of the high-purity neohesperidin dihydrochalcone crystal is characterized in that an alcohol solvent used for purifying neohesperidin in step S1 is methanol, ethanol or isopropanol, and the mass ratio of the neohesperidin to the alcohol solvent is 1:4-10.
  5. 5. The preparation method of the high-purity neohesperidin dihydrochalcone crystal according to claim 1, wherein the step S2 is characterized in that neohesperidin is synthesized by a one-pot method, and an alkali solution is a sodium hydroxide or potassium hydroxide aqueous solution with a mass fraction of 5% -20%.
  6. 6. The preparation method of the high-purity neohesperidin dihydrochalcone crystal according to claim 1, wherein the mass ratio of palladium carbon or Raney nickel to neohesperidin in the step S2 is 1:5-20.
  7. 7. The preparation method of the high-purity neohesperidin dihydrochalcone crystal according to claim 1 is characterized in that the mass ratio of the high-purity neohesperidin to an alkali solution in the step S2 is 1:4-20.
  8. 8. The preparation method of the high-purity neohesperidin dihydrochalcone crystal according to claim 1, wherein the reaction temperature in the step S2 is 20-40 ℃, the pressure is 0.5-3.0 MPa, and the reaction time is 10-15 hours.
  9. 9. The method for preparing high-purity neohesperidin dihydrochalcone crystals according to claim 1, wherein the alcohol in the step S2 is methanol, ethanol or isopropanol.
  10. 10. The preparation method of the high-purity neohesperidin dihydrochalcone crystal according to claim 1, wherein in the step S3, alcohol is methanol, ethanol or isopropanol, and the mass ratio of the alcohol to methyl tertiary butyl ether is 1:0.5-1.5.

Description

Preparation method of high-purity neohesperidin dihydrochalcone crystal Technical Field The invention relates to the technical field of sweeteners, in particular to a preparation method of high-purity neohesperidin dihydrochalcone crystals. Background The neohesperidin dihydrochalcone is obtained by biological conversion or chemical treatment of natural components of citrus, i.e. neohesperidin or naringin, and is a green food additive. The sweetness of the sweet potato is 1500-1800 times of that of sucrose, the sweet potato is slow in sweetness, long in time, good in stability, nontoxic, high in metabolism speed, and good in synergistic effect when being used with sucralose, maltol and the like, has the seasoning effects of sweetening, flavoring and covering bitter taste, can improve the defects of bad sour taste, astringency, aftertaste and the like when being used in carbonated beverages, and can be used as a flavoring agent and a corrective. Has extremely small heat energy value and strong oxidation resistance, has the activities of anti-inflammatory, blood sugar and blood lipid reducing, liver protecting and the like, and has wide application value. Neohesperidin dihydro chalcone is one a sweetener with very high safety. The current method for preparing neohesperidin dihydrochalcone chalcone mainly comprises the steps of carrying out hydrogenation reduction on neohesperidin in an alkali aqueous solution through a catalyst to obtain neohesperidin dihydrochalcone. The catalyst plays an important role in the reaction, and palladium carbon and skeleton nickel can be used as the catalyst for the reaction, but the palladium carbon is superior to the skeleton nickel in catalytic effect, and the dosage and the use times of the catalyst directly influence the yield of neohesperidin dihydrochalcone. The kind of catalysts, temperature, pressure, solvents and processes for synthesizing neohesperidin dihydrochalcone are discussed in detail by Shore (New hesperidin dihydrochalcone Process research [ J ]. Guangdong chemical industry, 2014, 12 (12): 55-56.), [ Lei Jia (New hesperidin dihydrochalcone Synthesis Process optimization [ J ]. Food science, 2014, 12 (39): 278-280.), [ Xu Guobo (Process research for synthesizing neohesperidin dihydrochalcone at ambient temperature and pressure [ J ]. Beijing chemical chemistry, 2010, 5 (37): 111-114.) and the like. The preparation method of neohesperidin mainly comprises the preparation methods of natural extraction, synthesizing neohesperidin by naringin chemical method, biological fermentation and the like. The natural extracted neohesperidin mainly exists in plants such as bitter hovenia dulcis, hedera helix and the like, the content of the neohesperidin is gradually reduced along with the maturity of fruits, so that the neohesperidin is extracted from the young fruits, the neohesperidin accounts for 3% -5% of the weight of the fresh fruits of the young fruits, the bitter hovenia dulcis is perennial, the period of the full-grown plants is required to be reached within 3-5 years, and the product supply is not required. The chemical synthesis and biological fermentation of naringin involve conversion rate and purification processes during the reaction process, and naringin and other impurities exist. In the traditional process for preparing neohesperidin dihydrochalcone, the purity of the raw material of the neohesperidin is low, and process impurities generated in the synthesis process lead to the low purity of the product of neohesperidin dihydrochalcone, which is generally white powder. The impurities not only affect the crystal form of the neohesperidin dihydrochalcone, but also affect the sweet feel of the neohesperidin dihydrochalcone, and the aftertaste is obvious. Disclosure of Invention Aiming at the problems, the invention provides a preparation method of high-purity neohesperidin dihydrochalcone, a crystal form and sweet taste evaluation thereof, the method adopts the pretreatment of the neohesperidin and optimizes the selection of a neohesperidin dihydrochalcone crystallization solvent to synthesize the high-purity neohesperidin dihydrochalcone. And the obtained neohesperidin dihydrochalcone needle crystal has high sweetness, long sweetness duration, high sweet abundance and long aftertaste. In order to achieve the purpose, the invention adopts the following technical scheme that the method comprises the following steps: S1, dissolving a neohesperidin raw material by using an alkaline solution, adding an acid and an alcohol solvent at room temperature after complete dissolution, crystallizing at low temperature, and performing suction filtration and drying to obtain high-purity neohesperidin; S2, generating neohesperidin dihydrochalcone in the presence of alkali solution, hydrogen, palladium carbon or Raney nickel, adjusting pH to 3-6, adding alcohol as a mixed solvent, and precipitating at normal temperature to obtain high-purity neohesperidin dihydrochalcone; S3