CN116333008A - Preparation method of rebaudioside E - Google Patents
Preparation method of rebaudioside E Download PDFInfo
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- CN116333008A CN116333008A CN202310240304.4A CN202310240304A CN116333008A CN 116333008 A CN116333008 A CN 116333008A CN 202310240304 A CN202310240304 A CN 202310240304A CN 116333008 A CN116333008 A CN 116333008A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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Abstract
The invention belongs to the technical field of sweetener preparation, and discloses a preparation method of rebaudioside E, which comprises the steps of dissolving stevioside raw materials in 90-99% of V/V methanol, stirring and dissolving, stirring and crystallizing at 10-40 ℃, adding the obtained crystals into 90-99% of V/V methanol, heating and stirring and refluxing, collecting filtered insoluble crystals, drying, adding the insoluble crystals into 50-70% of V/V methanol or ethanol, heating and stirring to slightly muddy, cooling and crystallizing, collecting and drying filtered mother liquor, adding into 40-70% of V/V methanol or ethanol, heating and stirring to slightly muddy, cooling and crystallizing, filtering and collecting crystals, and recrystallizing the crystals, filtering and drying to obtain a rebaudioside E finished product. The invention improves the purity of the rebaudioside E from 5-10% to the content of more than 95%, improves the development and utilization value of low-content stevioside, has simple process operation steps, is beneficial to the industrialized production of the rebaudioside E in the stevioside, and has safe and environment-friendly process.
Description
Technical Field
The invention belongs to the technical field of sweetener preparation, and particularly relates to a preparation method of rebaudioside E.
Background
Stevioside is a natural sweetener extracted from stevia rebaudiana Bertoni of Compositae, has the functional characteristics of high sweetness and low calorie, and has the sweetness 100-300 times that of sucrose and the calorie of only 1/300 of that of sucrose. Is praised as a third sugar source in the world, and is a natural sucrose substitute with use value and health requirement besides sugarcane and beet. At present, stevioside is widely applied to the industries of foods, beverages, medicines, wine brewing, daily chemical industry and the like.
Rebaudioside E is an isomer of rebaudioside a, of similar polarity, and not readily separable. Since rebaudioside E is present in stevia in small amounts, its research and use is inadequate. In the prior art, chinese patent application publication No. CN114794444 a describes obtaining a rebaudioside E-containing composition from stevia rebaudiana that yields leaves with higher rebaudioside E content by means of breeding, wherein a formulation with a relatively higher rebaudioside E content has a significant positive impact on the sweetness profile in the beverage. The chinese patent of application publication No. CN109750072a describes a method for preparing rebaudioside E by enzymatic method, which uses lick chrysanthemum glycoside as raw material and sucrose as substrate, and synthesizes stevioside rebaudioside E by the action of UDP-glycosyltransferase. However, both of the above patents are not directed to a specific purification method of rebaudioside E, and the content of rebaudioside E in the steviol glycoside composition is low, so that how to extract rebaudioside E from the steviol glycoside composition in high quality is an urgent problem to be solved.
The invention comprises the following steps:
the technical problems to be solved by the invention are as follows: provides a preparation method of rebaudioside E, overcomes the defects in the prior art, prepares a finished product with high rebaudioside E content by taking stevioside as a raw material through a separation and purification method of crystallization and recrystallization in different alcohol solutions, and meets the market demand.
In order to solve the technical problems, the technical scheme of the invention is as follows:
a method for preparing rebaudioside E, comprising the steps of:
a. dissolving stevioside raw material in 90-99% V/V methanol, stirring and dissolving at 60-120 rpm under normal temperature; stirring and crystallizing at 10-40 ℃ and 60-120 rpm, filtering, and drying the filter cake at 75-105 ℃ to obtain stevioside crystal;
b. adding the stevioside crystal obtained in the step a into 90-99% V/V methanol, stirring at 60-120 rpm, heating to 65-100 ℃ for reflux, filtering while hot, collecting the insoluble crystals, and drying at 75-105 ℃;
c. adding the insoluble crystals obtained in the step b into 50-70% V/V methanol or ethanol, heating to 70-85 ℃, stirring at 60-120 rpm until the mixture is slightly muddy, cooling to 20-40 ℃ for crystallization, filtering, collecting crystallization mother liquor, and drying;
d. c, adding the product obtained in the step c into 40-70% V/V methanol or ethanol, heating to 70-85 ℃, stirring at 60-120 rpm until the mixture is slightly muddy, cooling to 30-50 ℃ for crystallization, and filtering and collecting crystals to obtain a crude rebaudioside E product;
e. recrystallizing the crude rebaudioside E product obtained in the step d, filtering, and drying at 75-105 ℃ to obtain a rebaudioside E finished product.
Preferably, the stevioside raw material in the step a is stevioside with the stevioside total glycoside of 50-70% (the national food safety risk assessment center jecfa2019 standard) and the rebaudioside E content of 5-10%.
Preferably, in the step a, the solvent multiple is 2-6 BV of the weight of stevioside raw material, and the crystallization time is 16-48 h.
Further, in the step a, the solvent is 95-99% V/V methanol, the multiple of the solvent is 3-5 BV, the solvent is stirred and dissolved at 80-100 rpm, the crystallization temperature is 20-30 ℃, the solvent is stirred at 80-100 rpm, and the crystallization time is 24-48 h.
Preferably, in the step b, the solvent multiple is 4-10 BV of the weight of stevioside crystal, and the heating reflux time is 20-60 min.
Further, in the step b, the solvent is 90-99% V/V methanol, the solvent multiple is 6-10 BV, the stirring speed is 80-100 rpm, the heating reflux temperature is 75-85 ℃, and the reflux time is 20-30 min.
Preferably, in the step c, the solvent multiple is 2-6 BV of the weight of the insoluble crystals, and the crystallization time is 6-24 h.
Further, in the step c, the solvent is 60-70% V/V ethanol, the solvent multiple is 4-6 BV, the solvent is heated to 70-80 ℃, stirred at 80-100 rpm until the solvent is slightly muddy, cooled to 30-40 ℃ and crystallized, and the crystallization time is 12-24 hours.
Preferably, the solvent multiple in the step d is 4-8 BV of the weight of the product in the step c, and the crystallization time is 6-12 h.
Further, in the step d, the solvent is 50-70% V/V methanol, the multiple of the solvent is 4-6 BV, the solvent is heated to 70-80 ℃, stirred at 80-100 rpm, the crystallization temperature is 40-50 ℃, and the crystallization time is 6-8 h.
Preferably, the solvent used in the recrystallization in the step E is 40-60% V/V methanol or ethanol, the solvent multiple is 4-10 BV of the weight of the crude rebaudioside E product, the solvent is heated to 70-90 ℃, and the solvent is stirred at 60-120 rpm until the solvent is completely dissolved, the crystallization temperature is 40-60 ℃, and the crystallization time is 4-8 h.
Further, in the step E, the solvent used for recrystallization is 40-50% V/V methanol, the solvent multiple is 4-8 BV of the weight of the crude rebaudioside E product, the solvent is heated to 70-80 ℃, stirred at 80-100 rpm until the solvent is completely dissolved, the crystallization temperature is 40-50 ℃, and the crystallization time is 4-6 h.
The principle of the invention is as follows:
utilizing the low solubility of the rebaudioside E in the high-concentration alcohol solvent, and primarily purifying the rebaudioside E by stirring and crystallizing the high-concentration alcohol solvent at normal temperature; due to the crystalline purified rebaudioside E content, it will exhibit lower solubility in hot high-concentration alcohol solvents, with elevated temperatures resulting in increased solubility of other substances, while rebaudioside E will have low solubility in hot high-concentration alcohol solvents due to low solubility; therefore, by utilizing the solubility difference in the way of heating reflux, other soluble impurities and other glycosides are dissolved in the hot alcohol solvent, while the property that most of rebaudioside E is insoluble in the high-concentration alcohol solvent is further separated, and insoluble solid matters are further purified by the way of low-alcohol crystallization and recrystallization.
Due to the adoption of the technical scheme, the invention has the beneficial effects that:
the invention provides a preparation method of rebaudioside E, which takes stevioside enriched by resin in stevioside extract as a raw material, adopts a separation and purification method of crystallization and recrystallization, improves the purity of the rebaudioside E from 5-10% to the content of more than 95%, and improves the development and utilization value of low-content stevioside. And the process has simple operation steps, is favorable for the industrial production of the rebaudioside E in the stevioside, and is safe and environment-friendly.
Detailed Description
The technical scheme of the invention is further described below by combining examples:
example 1:
a. 100g of stevioside (64.5% of total glycosides, 8.8% of rebaudioside E, 14.3% of rebaudioside D, 2.9% of rebaudioside M, 19.3% of rebaudioside A and 4.9% of stevioside) is taken and added into 90% methanol with a solvent multiple of 2.0BV, stirred and dissolved at 60rpm, after complete dissolution, the temperature is reduced to 10 ℃ for crystallization, the rotation speed is 120rpm, the crystallization time is 16h, the filtration is carried out through filter paper, a filter cake is collected, and the filter cake is dried at 105 ℃, the dry weight of the obtained crystal is 43.5g, wherein the rebaudioside E accounts for 15.7%.
b. C, adding the crystalline substance obtained in the step a into 90% methanol solvent with the solvent multiple of 4.0BV, heating at 65 ℃, stirring at 60rpm, and refluxing for 60min; filtering with filter paper to obtain reflux insoluble crystal, and drying at 105deg.C to obtain crystal 13.8g, wherein rebaudioside E accounts for 36.2%.
c. And c, adding the crystals obtained in the step b into 50% ethanol with the solvent multiple of 2.0BV, heating to 70 ℃, stirring at 60rpm, dissolving to be slightly muddy, cooling to 20 ℃, preserving heat for crystallization for 6.0h, filtering to obtain a crystallization mother liquor by the method of the step a, and drying the mother liquor to obtain 5.4g, wherein the rebaudioside E accounts for 69.2%.
d. C, adding 40% methanol with the solvent multiple of 4.0BV into the crystal obtained in the step c, heating to 70 ℃, stirring at 60rpm, dissolving to be slightly muddy, continuously stirring, slowly cooling to 30 ℃, preserving heat for crystallization, and filtering and drying in the step a for 6.0h to obtain 3.4g of crystal, wherein the rebaudioside E accounts for 85.8%.
e. Taking the crystal obtained in the step d, adding 40% methanol with the solvent multiple of 4.0BV, heating to 70 ℃, stirring at 60rpm, dissolving to be slightly muddy, continuously stirring, slowly cooling to 40 ℃, preserving heat for crystallization, and filtering and drying in the step a for 4.0h to obtain 2.4g of crystal, wherein the purity of rebaudioside E is 97.6%.
Example 2:
a. 100g of stevioside (64.5% of total glycosides, 8.8% of rebaudioside E, 14.3% of rebaudioside D, 2.9% of rebaudioside M, 19.3% of rebaudioside A and 4.9% of stevioside) was added to 99% methanol with a solvent multiple of 6BV, stirred and dissolved at 120rpm, and completely dissolved, and crystallized at 40 ℃ with a rotation speed of 60rpm for 48 hours, filtered through filter paper, and the filter cake was collected, and dried at 75 ℃ to obtain a crystal dry weight of 41.1g, wherein rebaudioside E accounts for 18.2%.
b. C, adding the crystalline substance obtained in the step a into 99% methanol solvent with the solvent multiple of 10BV, heating at 100 ℃, stirring at 120rpm, and refluxing for 20min; filtering with filter paper to obtain reflux insoluble crystal, and drying at 75deg.C to obtain crystal weight of 14.3g, wherein rebaudioside E accounts for 40.5%.
c. And c, adding the crystals obtained in the step b into 70% ethanol with the solvent multiple of 6BV, heating to 85 ℃, stirring at 120rpm, dissolving to be slightly muddy, cooling to 60 ℃, preserving heat for crystallization, and carrying out crystallization for 24 hours, wherein the crystallization mother liquor is obtained by filtering in the step a method, and the total weight of the mother liquor is 7.7g after drying, wherein the rebaudioside E accounts for 59.1%.
d. C, adding 70% methanol with the solvent multiple of 8BV into the crystal obtained in the step c, heating to 85 ℃, stirring at 120rpm, dissolving to be slightly muddy, continuously stirring, slowly cooling to 50 ℃, preserving heat for crystallization, and filtering and drying for 12h, wherein the rebaudioside E accounts for 78.6% of the crystal obtained in the step a, and the crystal is 4.8 g.
e. And d, adding 60% methanol with the solvent multiple of 10BV into the crystal obtained in the step d, heating to 90 ℃, stirring at 120rpm, dissolving to be slightly muddy, continuously stirring, slowly cooling to 60 ℃, preserving heat for crystallization, and filtering and drying for 8 hours, wherein the purity of the rebaudioside E is 92.3%, so as to obtain 3.2g of the crystal.
Example 3:
a. 100g of stevioside (64.5% of total glycosides, 8.8% of rebaudioside E, 14.3% of rebaudioside D, 2.9% of rebaudioside M, 19.3% of rebaudioside A and 4.9% of stevioside) is taken and added into 95% methanol with a solvent multiple of 4BV, stirred and dissolved at 90rpm, after complete dissolution, the temperature is reduced to 25 ℃ for crystallization, the rotation speed is 90rpm, the crystallization time is 24h, the filtration is carried out through filter paper, a filter cake is collected, and the dry weight of the obtained crystal is 40.2g at 100 ℃, wherein the rebaudioside E accounts for 18%.
b. C, adding the crystalline substance obtained in the step a into 98% methanol solvent with the solvent multiple of 6BV, heating at 80 ℃, stirring at 90rpm, and refluxing for 30min; filtering with filter paper to obtain reflux insoluble crystal, and drying at 100deg.C to obtain crystal weight 15.3g, wherein rebaudioside E accounts for 39.5%.
c. And c, adding the crystals obtained in the step b into 60% ethanol with the solvent multiple of 4BV, heating to 80 ℃, stirring at 80rpm, dissolving to be slightly muddy, cooling to 30 ℃, preserving heat for crystallization, and carrying out crystallization for 12 hours, wherein the crystallization mother liquor is obtained by filtering in the step a method, and the total amount of 8.4g is obtained after the mother liquor is dried, wherein the rebaudioside E accounts for 61.5%.
d. C, adding 50% methanol with the solvent multiple of 4BV into the crystal obtained in the step c, heating to 80 ℃, stirring at 80rpm, dissolving to be slightly muddy, continuously stirring, slowly cooling to 40 ℃ and preserving heat for crystallization, wherein the crystallization time is 12h, filtering and drying the crystal in the step a to obtain 5.2g of crystal, and the rebaudioside E accounts for 81.1%.
e. And d, adding 50% methanol with the solvent multiple of 8BV into the crystal obtained in the step d, heating to 80 ℃, stirring at 80rpm, dissolving to be slightly muddy, continuously stirring, slowly cooling to 50 ℃, preserving heat for crystallization, and filtering and drying for 6 hours, wherein 3.5g of crystal is obtained, and the purity of rebaudioside E is 96.3%.
Example 4:
step a, step b are the same as in example 3, step c is:
c. and c, adding the crystals obtained in the step b into 70% methanol with the solvent multiple of 4BV, heating to 80 ℃, stirring at 80rpm, dissolving to be slightly muddy, cooling to 30 ℃ and preserving heat for crystallization for 12 hours, filtering to obtain a crystallization mother liquor by the step a, and drying the mother liquor to obtain 9g, wherein the rebaudioside E accounts for 53.6%.
Step d, step E are the same as embodiment 3, and the resulting crystals weigh 4.2 grams, with a rebaudioside E purity of 88.6%.
Example 5:
step a, step b, step c are the same as in example 3, step d is:
d. c, adding 50% ethanol with the solvent multiple of 4BV into the crystal obtained in the step c, heating to 80 ℃, stirring at 80rpm, dissolving to be slightly muddy, continuously stirring, slowly cooling to 40 ℃ and preserving heat for crystallization, wherein the crystallization time is 12h, filtering and drying the crystal in the step a to obtain 6.3g of crystal, and the rebaudioside E accounts for 76.1%.
Step E is the same as embodiment 3, and the resulting crystals weigh 4.8 grams, with rebaudioside E purity 85.2%.
Example 6:
step a, step b, step c, step d are the same as in example 3, step e is:
e. and d, adding 50% ethanol with the solvent multiple of 4BV into the crystal obtained in the step d, heating to 85 ℃, stirring at 80rpm, dissolving to be slightly muddy, continuously stirring, slowly cooling to 50 ℃, preserving heat for crystallization, and filtering and drying for 8 hours, wherein 3.9g of crystal is obtained, and the purity of rebaudioside E is 90.7%.
Analysis of results:
from analysis of the data obtained in embodiments 1-6, it can be seen that embodiment 3 of the present invention is optimal, and the resulting end product rebaudioside E purity is 96.3%, although not as high as embodiment 1 (97.6%), but in much higher yields than embodiment 1 (3.5 g VS 2.4 g), so embodiment 3 is more cost-effective; the fourth to sixth embodiments are examination of the solvent in the crystallization process, and the solvent is replaced with methyl and ethanol to be dissolved, which has a certain effect of improving the content of rebaudioside E, but is lower than the amount of improvement of the content of rebaudioside E in the corresponding embodiments 1 to 3.
It is to be understood that these examples are illustrative of the present invention and are not intended to limit the scope of the present invention. Further, it is understood that various changes and modifications may be made by those skilled in the art after reading the teachings of the present invention, and such equivalents are intended to fall within the scope of the claims appended hereto.
Claims (10)
1. A method for preparing rebaudioside E, comprising the steps of:
a. dissolving stevioside raw material in 90-99% V/V methanol, stirring and dissolving at 60-120 rpm under normal temperature; stirring and crystallizing at 10-40 ℃ and 60-120 rpm, filtering, and drying the filter cake at 75-105 ℃ to obtain stevioside crystal;
b. adding the stevioside crystal obtained in the step a into 90-99% V/V methanol, stirring at 60-120 rpm, heating to 65-100 ℃ for reflux, filtering while hot, collecting the insoluble crystals, and drying at 75-105 ℃;
c. adding the insoluble crystals obtained in the step b into 50-70% V/V methanol or ethanol, heating to 70-85 ℃, stirring at 60-120 rpm until the insoluble crystals are slightly muddy, cooling to 20-40 ℃ for crystallization, filtering, collecting crystallization mother liquor, and drying;
d. c, adding the product obtained in the step c into 40-70% V/V methanol or ethanol, heating to 70-85 ℃, stirring at 60-120 rpm until the mixture is slightly muddy, cooling to 30-50 ℃ for crystallization, and filtering and collecting crystals to obtain a crude rebaudioside E product;
e. recrystallizing the crude rebaudioside E product obtained in the step d, filtering, and drying at 75-105 ℃ to obtain a rebaudioside E finished product.
2. The method for preparing rebaudioside E according to claim 1, wherein: the stevioside raw material in the step a is stevioside with 50-70% of stevioside total glycoside and 5-10% of rebaudioside E.
3. The method for preparing rebaudioside E according to claim 1, wherein: the solvent multiple in the step a is 2-6 BV of the weight of stevioside raw material, and the crystallization time is 16-48 h.
4. The method for preparing rebaudioside E according to claim 1, wherein: and b, the solvent multiple in the step is 4-10 BV of the weight of stevioside crystal, and the heating reflux time is 20-60 min.
5. The method for preparing rebaudioside E according to claim 1, wherein: and c, the solvent multiple in the step is 2-6 BV of the weight of the insoluble crystals, and the crystallization time is 6-24 h.
6. The method for preparing rebaudioside E according to claim 5, wherein: the solvent in the step c is 60-70% V/V ethanol.
7. The method for preparing rebaudioside E according to claim 1, wherein: and in the step d, the solvent multiple is 4-8 BV of the weight of the product in the step c, and the crystallization time is 6-12 h.
8. The method for preparing rebaudioside E according to claim 7, wherein: the solvent in the step d is 50-70% V/V methanol.
9. The method for preparing rebaudioside E according to claim 1, wherein: and E, the solvent used for recrystallization is 40-60% V/V methanol or ethanol, the solvent multiple is 4-10 BV of the weight of the crude rebaudioside E product, the solvent is heated to 70-90 ℃, and the solvent is stirred at 60-120 rpm until the solvent is completely dissolved, the crystallization temperature is 40-60 ℃, and the crystallization time is 4-8 h.
10. The method for preparing rebaudioside E according to claim 9, wherein: the solvent used for recrystallization in the step e is 40-50% V/V methanol.
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