CN104193786A - Synthesis method of neohesperidin dihydrochalcone - Google Patents
Synthesis method of neohesperidin dihydrochalcone Download PDFInfo
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- CN104193786A CN104193786A CN201410381551.7A CN201410381551A CN104193786A CN 104193786 A CN104193786 A CN 104193786A CN 201410381551 A CN201410381551 A CN 201410381551A CN 104193786 A CN104193786 A CN 104193786A
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- neohesperidin dihydrochalcone
- neohesperidin
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- dihydrochalcone
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Abstract
The invention relates to a preparation method of neohesperidin dihydrochalcone. According to the preparation method, neohesperidin is adopted as a starting raw material, methanol and ethanol are adopted as reaction mediums and sodium borohydride and potassium borohydride are subjected to hydrogenation reduction and reacted under a heating condition to prepare the neohesperidin dihydrochalcone. The reparation method has the advantages of less environmental pollution, low production cost, good quality and high yield and is simple and easily operated and is suitable for industrial production.
Description
Technical field
The synthetic method that the present invention relates to a kind of neohesperidin dihydrochalcone, belongs to chemosynthesis technical field.
Background technology
Neohesperidin dihydrochalcone is the flavone derivative that the neohesperidin extracted from citrus natural phant forms through over hydrogenation, is a kind of functional sweetener with debitter and flavour improvement.
The sugariness of neohesperidin dihydrochalcone is 1500-1800 times of sucrose sweetness, and clean taste, and sweet taste is lasting.The glycosyl of neohesperidin dihydrochalcone can be hydrolyzed in vivo, and glycosyl can not participate in organism metabolism, and the having good stability of neohesperidin dihydrochalcone, toxicological harmless effect, so thereby also can be used as a kind of unique additives is used in conjunction with in improving food-drink flavor taste or acting on animal-feed and improves animal cultivation efficiency to strengthen animal appetite with other sweeting agents.
Therefore, neohesperidin dihydrochalcone is having wide practical use aspect the industries such as food, is below the preparation scheme of a class neohesperidin dihydrochalcone traditional technology:
(1) preparation of neohesperidin dihydrochalcone: by the sodium hydrate methanol solution of a certain amount of neohesperidin dihydrochalcone massfraction 30%, add again the palladium carbon of neohesperidin amount 20% as catalyzer, then under 30～90 DEG C of conditions of hydrogen pressure heating in water bath of 2.5Mpa, react 8～10 hours, then leaching reaction solution hydrochloric acid adjusts pH to neutral, place after 24～48 hours crystallizatioies, leach crystal, after being dried, obtain neohesperidin dihydrochalcone crude product;
(2) purifying of neohesperidin dihydrochalcone: Hesperidin dihydrochalcone crude product adds in hot water, add again after the gac continuous heating decolouring in 2 hours of crude product quality 10%, filtering gac while hot, then the cold filtrate crystallize out of putting, filter crystal after dry neohesperidin dihydrochalcone fine work.
This class technique alkali charge is larger, causes the unnecessary wasting of resources; Palladium catalyst carbon is expensive, has increased production cost; Hydrogen in reaction pressure is larger, except increasing technology difficulty, has also reduced security; When neohesperidin dihydrochalcone purifying, add activated carbon decolorizing, increased operation steps, also bring the risk of introducing impurity in operation.
Summary of the invention
The present invention adopts following technical scheme: taking neohesperidin as starting raw material, methanol/ethanol is made reaction medium, sodium borohydride POTASSIUM BOROHYDRIDE is made reduction hydrogenation, reaction preparation neohesperidin dihydrochalcone under heating condition, and the dry solvent of concentrating under reduced pressure obtains neohesperidin dihydrochalcone crude product.
As the further improvement of the embodiment of the present invention, described synthetic method further comprises the step of neohesperidin dihydrochalcone crude product being carried out to purifying, obtains neohesperidin dihydrochalcone fine work.
As the further improvement of the embodiment of the present invention, the step of described purifying comprises: neohesperidin dihydrochalcone crude product is joined and in methyl alcohol or ethanol, carries out repeatedly recrystallization.
As the further improvement of the embodiment of the present invention, described recrystallization methyl alcohol used, ethanol volume are: methyl alcohol, ethanol: neohesperidin dihydrochalcone crude product (V/W)=3; 1～8:1.
An aspect of of the present present invention, methyl alcohol, ethanol: raw material neohesperidin (V/W)=10:1～15:1.
Another aspect of the present invention, sodium borohydride, POTASSIUM BOROHYDRIDE consumption are 0.5～1 times of molar weights of neohesperidin.
One side more of the present invention, 40～60 DEG C of temperature of reaction.
The present invention possesses following advantage:
The present invention possesses following advantage:
1, neohesperidin dihydrochalcone synthesis technique described in invention has been abandoned traditional drawback of reacting under hydrogen condition of high voltage, makes the security of industrialized production obtain the change of matter, has reduced the requirement of processing unit simultaneously, reduces production costs.
2, invention solvent for use, Environmental Safety, and recyclable recycling have greatly reduced again production cost when reduction environmental toxicity economizes on resources.
3, sodium borohydride, potassium borohydride reduction hydrogenation for invention, more traditional noble metal catalyst is more cheap.
4, preparation technology's easy handling of neohesperidin dihydrochalcone in invention, mild condition, energy consumption is low.
5, in invention, neohesperidin dihydrochalcone later stage purification step is simple, prepares yield high, and quality is good.
Brief description of the drawings
fig. 1for the structural formula of neohesperidin dihydrochalcone.
Embodiment
The embodiment of the invention discloses a kind of synthetic method of neohesperidin dihydrochalcone.Those skilled in the art can use for reference content herein, suitably improve processing parameter and realize.Special needs to be pointed out is, all similar replacements and change apparent to those skilled in the artly, they are all deemed to be included in the present invention.Application of the present invention is described by preferred embodiment, and related personnel obviously can change application as herein described in content of the present invention, spirit and scope or suitably change and combination not departing from, and realizes and apply the technology of the present invention.
In order further to understand the present invention, below in conjunction with embodiment, the present invention is described in detail.
Embodiment 1:
(1) take 10g neohesperidin and be placed in the there-necked flask that configures thermometer, measure after 100mL methyl alcohol stirring and dissolving neohesperidin, taking 0.5g sodium borohydride adds in there-necked flask, at 45 DEG C of strict temperature controls, react 4～6h, TLC thin-layer chromatography is followed the tracks of reaction, after question response finishes, evaporated under reduced pressure solvent had both obtained neohesperidin dihydrochalcone crude product.
(2) get neohesperidin dihydrochalcone crude product 5g, add 25mL methyl alcohol, 50 DEG C of heated and stirred molten clear after ,-5～0 DEG C of crystallization leached crystallization after 4 hours, after recrystallization 1～2 time, draw crystal again, lyophilize crystal both neohesperidin dihydro be looked into diketone fine work.Shou Shuais≤and 90%, Chun Du≤98.1%.
The structural formula that the neohesperidin dihydro obtaining is looked into diketone as shown in Figure 1.
Embodiment 2:
(1) take 10g neohesperidin and be placed in the there-necked flask that configures thermometer, measure after 100mL ethanol stirring and dissolving neohesperidin, taking 0.5g sodium borohydride adds in there-necked flask, at 55 DEG C of strict temperature controls, react 4～6h, TLC thin-layer chromatography is followed the tracks of reaction, after question response finishes, evaporated under reduced pressure solvent had both obtained neohesperidin dihydrochalcone crude product.
(2) get neohesperidin dihydrochalcone crude product 5g, add 15mL ethanol, 60 DEG C of heated and stirred molten clear after ,-5～0 DEG C of crystallization leached crystallization after 4 hours, after recrystallization 1～2 time, draw crystal again, lyophilize crystal both neohesperidin dihydro be looked into diketone fine work.Shou Shuais≤and 89%, Chun Du≤97.6%.
Embodiment 3:
(1) take 50g neohesperidin and be placed in the there-necked flask that configures thermometer, measure after 500mL ethanol stirring and dissolving neohesperidin, taking 4.8g POTASSIUM BOROHYDRIDE adds in there-necked flask, at 55 DEG C of strict temperature controls, react 4～6h, TLC thin-layer chromatography is followed the tracks of reaction, after question response finishes, evaporated under reduced pressure solvent had both obtained neohesperidin dihydrochalcone crude product.
(2) get neohesperidin dihydrochalcone crude product 40g, add 200mL ethanol, 60 DEG C of heated and stirred molten clear after ,-5～0 DEG C of crystallization leached crystallization after 4 hours, after recrystallization 1～2 time, draw crystal again, lyophilize crystal both neohesperidin dihydro be looked into diketone fine work.Shou Shuais≤and 87%, Chun Du≤98.5%.
Claims (7)
1. the synthetic method of a neohesperidin dihydrochalcone, its special character is: taking neohesperidin as starting raw material, methyl alcohol, ethanol are made reaction medium, sodium borohydride, POTASSIUM BOROHYDRIDE are made reduction hydrogenation, reaction preparation neohesperidin dihydrochalcone under heating condition, the dry solvent of concentrating under reduced pressure obtains neohesperidin dihydrochalcone crude product.
2. the synthetic method of neohesperidin dihydrochalcone as claimed in claim 1, is characterized in that: described synthetic method further comprises the step of neohesperidin dihydrochalcone crude product being carried out to purifying, obtains neohesperidin dihydrochalcone fine work.
3. the synthetic method of neohesperidin dihydrochalcone as claimed in claim 2, is characterized in that: the step of described purifying comprises: neohesperidin dihydrochalcone crude product is joined and in methyl alcohol, ethanol, carries out repeatedly recrystallization.
4. the synthetic method of neohesperidin dihydrochalcone as claimed in claim 3, is characterized in that: described recrystallization methyl alcohol used, ethanol volume are: methyl alcohol, ethanol: neohesperidin dihydrochalcone crude product (V/W)=3; 1～8:1.
5. the synthetic method of neohesperidin dihydrochalcone as claimed in claim 1, is characterized in that: methyl alcohol, ethanol: raw material neohesperidin (V/W)=10:1～15:1.
6. the synthetic method of neohesperidin dihydrochalcone as claimed in claim 1, is characterized in that: described sodium borohydride, POTASSIUM BOROHYDRIDE consumption are 0.5～1 times of molar weights of neohesperidin.
7. the synthetic method of neohesperidin dihydrochalcone as claimed in claim 1, is characterized in that: 40～60 DEG C of temperature of reaction.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110498821A (en) * | 2019-08-22 | 2019-11-26 | 湖南省农产品加工研究所 | A method of synthesis neohesperidin dihydrochalcone |
Citations (4)
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|---|---|---|---|---|
| EP0598359A1 (en) * | 1992-11-12 | 1994-05-25 | Tanabe Seiyaku Co., Ltd. | Hypoglycemic dihydrochalcone derivatives |
| CN1305743A (en) * | 2000-12-27 | 2001-08-01 | 中国科学院广州化学研究所 | Process for synthesizing dihydrochalcone-type sweetening agent |
| KR20110088743A (en) * | 2010-01-29 | 2011-08-04 | 한국생명공학연구원 | A method of preparation of neohesperidin dihydrochalcone from citrus peel by using supercritical fluid extraction |
| CN103804439A (en) * | 2014-03-01 | 2014-05-21 | 张家港威胜生物医药有限公司 | Synthesis method for neohesperidin dihydrochalcone |
-
2014
- 2014-08-05 CN CN201410381551.7A patent/CN104193786A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0598359A1 (en) * | 1992-11-12 | 1994-05-25 | Tanabe Seiyaku Co., Ltd. | Hypoglycemic dihydrochalcone derivatives |
| CN1305743A (en) * | 2000-12-27 | 2001-08-01 | 中国科学院广州化学研究所 | Process for synthesizing dihydrochalcone-type sweetening agent |
| KR20110088743A (en) * | 2010-01-29 | 2011-08-04 | 한국생명공학연구원 | A method of preparation of neohesperidin dihydrochalcone from citrus peel by using supercritical fluid extraction |
| CN103804439A (en) * | 2014-03-01 | 2014-05-21 | 张家港威胜生物医药有限公司 | Synthesis method for neohesperidin dihydrochalcone |
Non-Patent Citations (4)
| Title |
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| 刘宇宏等: "硼氢化钠的性能与研究", 《企业科技与发展》 * |
| 戴利等: "活性硼氢化钠在有机合成中的应用", 《山东化工》 * |
| 温辉梁等: "新橙皮苷二氢查尔酮的研究进展", 《中国调味品》 * |
| 白银娟等: "硼氢化钠在有机合成中的研究进展", 《应用化学》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110498821A (en) * | 2019-08-22 | 2019-11-26 | 湖南省农产品加工研究所 | A method of synthesis neohesperidin dihydrochalcone |
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Application publication date: 20141210 |