CN103113438A - Method for extracting hesperidin and orange peel uranidin from orange peel - Google Patents
Method for extracting hesperidin and orange peel uranidin from orange peel Download PDFInfo
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- CN103113438A CN103113438A CN2013100361058A CN201310036105A CN103113438A CN 103113438 A CN103113438 A CN 103113438A CN 2013100361058 A CN2013100361058 A CN 2013100361058A CN 201310036105 A CN201310036105 A CN 201310036105A CN 103113438 A CN103113438 A CN 103113438A
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- QUQPHWDTPGMPEX-UHFFFAOYSA-N Hesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(COC4C(C(O)C(O)C(C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-UHFFFAOYSA-N 0.000 title claims abstract description 43
- QUQPHWDTPGMPEX-QJBIFVCTSA-N hesperidin Chemical compound C1=C(O)C(OC)=CC=C1[C@H]1OC2=CC(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]4[C@@H]([C@H](O)[C@@H](O)[C@H](C)O4)O)O3)O)=CC(O)=C2C(=O)C1 QUQPHWDTPGMPEX-QJBIFVCTSA-N 0.000 title claims abstract description 43
- 238000000034 method Methods 0.000 title claims abstract description 26
- ARGKVCXINMKCAZ-UHFFFAOYSA-N neohesperidine Natural products C1=C(O)C(OC)=CC=C1C1OC2=CC(OC3C(C(O)C(O)C(CO)O3)OC3C(C(O)C(O)C(C)O3)O)=CC(O)=C2C(=O)C1 ARGKVCXINMKCAZ-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000001100 (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one Substances 0.000 title claims abstract description 20
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Landscapes
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention provides a process technology for simultaneously extracting hesperidin and orange peel uranidin from orange peel. The process technology comprises the following steps of: refluxing and extracting the dried orange peel by acid alcohol, filtering, concentrating, neutralizing, re-filtering, adding alkali to dissolve filter residues, neutralizing and crystallizing to obtain an orange peel glycoside pure product; and adding alcohol to the filtrate to extract the orange peel glycoside pure product, and concentrating and drying the extracted orange peel glycoside pure product to obtain the orange peel uranidin product. The method is simple to operate, capable of greatly reducing the production cost of the hesperidin and orange peel uranidin and capable of simplifying the production process.
Description
Affiliated technical field
Belong to the Separation of Natural Products technical field, relate to the comprehensive utilization of the medicinal plants such as a kind of citrus peel, more specifically to a kind of Technology of extracting simultaneously Hesperidin and Yellow Pigment in Tangerine Peel from tangerine peel.
Background technology
China's oranges and tangerines resource and output Jun Ju third place in the world, output reaches 1,078 ten thousand tons, and all there is cultivation all parts of the country.Present most of tangerine meat is utilized, and a large amount of tangerine peel all goes out of use, and the Chinese medicine orange peel is otherwise known as.Also available fresh orange peel enters dish, herbal cuisine, can add orange peel during the cooking except the gas of the smelling of fish or mutton.In orange peel, main component is Hesperidin, and the flavonoid compound that coexists in orange peel with Hesperidin also has neohesperidin, citrus xanthosine, Yellow Pigment in Tangerine Peel, auranetin, also has in addition neutral lactone amaroid vitamin P and volatilization wet goods composition.Flavor is arduous, and is warm in nature nontoxic, and the effect of activating QI to eliminate phlegm is arranged, and can be used as medicine.These pharmacologically actives are given the credit to the compositions such as Yellow Pigment in Tangerine Peel in tangerine peel, Hesperidin, thereby in the research tangerine peel, the extractive technique of these two kinds of compositions is significant.
Yellow Pigment in Tangerine Peel has another name called Yellow Pigment from Tangerine Peel, peel of Citrus reticulata Blanco pigment, naringin.Orange peel is yellow or orange, wherein is rich in orange-yellow carotenoid.Had now found that 20 multiple types carotene in Pigment of Orange Peel, existed mainly with oxygenatedchemicals, as zeaxanthin diepoxide, yellowish matter, epoxy pearl xanthin, zeaxanthin, corpus luteum system etc., the nontoxic and easily collecting of tangerine peel is the fine raw material that extracts yellow pigment.Orange peel not only can extract pigment, and can extract volatile oil, pectin, realizes the comprehensive utilization of tangerine peel, is a kind of natural resource of worth exploitation.
Hesperidin has another name called hesperidine, hesperidin, belongs to the natural flavone compounds, and its sterling is white needle-like crystals or pale yellow powder, and bitter is warm in nature, molecular formula C
28H
34O
15Molecular weight 610.57, fusing point 258-262 ℃, be dissolved in hardly cold water, but larger solubleness is arranged in ethanol or hot water, dissolve in pyridine, glycerine, acetic acid or dilute alkaline soln, be insoluble in chloroform, acetone, ether or benzene, with iron trichloride, metallic salt reaction solution or generation precipitation, be red-purple with hydrochloric acid-magnesium powder reaction.
Hesperidin is very extensive in distributed in nature, mainly is present in pulse family, white birch, Labiatae, Papilionaceae, Rutaceae, citrus plant body.The effects such as Hesperidin has good biological activity, has the oxidation of lipotropism matter and removes oxyradical, and anti-inflammatory, antiviral, antibiotic strengthens capillary vessel toughness, shortens the bleeding time, and anticancer is active and delay senility.Hesperidin has the osmotic pressure of keeping, and strengthens capillary vessel toughness, shortens the bleeding time, reduce the effects such as cholesterol, being used for clinically the assisting therapy of cardiovascular system diseases, can cultivating the multiple medicine that prevents arteriosclerosis and myocardial infarction, is one of main raw material of patent medicine " Maitong ".Can be used as natural antioxidants in foodstuffs industry.Also can be used for cosmetic industry.The Hesperidin major part is present in the waste of citrus processing, in pericarp, fruit capsule, and the content of Hesperidin the highest (endocarp 30%-50%, in tangerine peel, core, pulp 30%-50%, exocarp 10%-20%) in ripe pericarp and tissue wherein.In juice and tangerine capsule, content hangs down 1%-5%.
Publication number is that the Chinese patent of CN01106994 discloses a kind of method of extracting the medicinal raw material synephrine from traditional Chinese medicine citrus aurantium, the method is to use the water extraction dried immature fruit of citron orange, extracting solution is through concentrated, alcohol precipitation, recovery ethanol, sand filtration, then go up cationic resin column, first rinse with suitable quantity of water, use certain density ammoniacal liquor wash-out, the ammoniacal liquor elutriant is through concentrated direct crystallization again, and recrystallization namely gets synephrine.Present method has the advantages such as operating process is simple, production cost is low.
Publication number is that the Chinese patent of CN102276669A discloses the preparation method who extracts hesperidine from the dried immature fruit of citron orange, and comprise the following steps: (1) prepares raw material is that dried immature fruit of citron orange fine powder is poured in extractor; (2) the configuration alkaline solution is made after immersion treatment emptying liquid stirring again to material in tank; (3) the configuration alkaline solution is done thermal treatment to material in tank; (4) the configuration alkaline solution is made for the first time after percolation treatment emptying liquid stirring again to material in tank; (5) the configuration alkaline solution is made for the second time after percolation treatment emptying liquid stirring again to material in tank; (6) pump into extracting solution and extract hesperidine; (7) the hesperidine crystallization of isolating; (8) to hesperidine crystallization be filtered dry, drying and processing.
Publication number is that the Chinese patent of CN102050855A discloses a kind of method of comprehensively extracting synephrine and hesperidine from immature bitter orange raw material, the wasting of resources that can't cause two kinds of product comprehensive exploitations to overcome prior art, and the optimization extraction step reduces production costs, and promotes operability.After raw material pulverizing, adopt alkali organic solvent to extract; United extraction liquid is concentrated into proportion 1.05, filters the filtrate decolouring; Filtrate is transferred to neutrality, filter to get the Hesperidin product, yield 25%, content 95%; The mother liquor that filtration obtains is adjusted to strong basicity, adopts the mixed organic solvents extraction, is concentrated into certain volume and adds little polar solvent crystallization, and product yield is 1.2%, and synephrine content is 98%.The present invention has realized immature bitter orange raw material is taken full advantage of, and design technology is produced synephrine and two kinds of products of hesperidine simultaneously, greatly reduces production cost; Overall leaching process is optimized more, has shortened technical process, saves production cost.
Publication number is that the Chinese patent of CN102526295A discloses a kind of method that fully utilizes dried orange peel, with dried orange peel 40 crushed after being dried, adopt Subcritical Water Extraction technology stepless control temperature and pressure, according to descending water-soluble polysaccharide (5MPa, 150-180 ℃), flavones and phenols (5MPa, 120-140 ℃), triterpenes (5MPa, 100-110 ℃) and essential oil (5MPa, the 70-90 ℃) composition that obtains respectively in dried orange peel of polarity, yield is respectively 5.1-7.6%, 0.8-1.5%, 0.4-1.1%, 3.0-3.2%.Essential oil can be used for making essence and flavoring agent, and triterpene, flavones and phenols and water-soluble polysaccharide composition can be used for further separation and purification and obtain pharmaceutically acceptable composition, and after extracting, remaining dregs part can be in order to make sweetend roll etc.This invention makes the opposed polarity composition of dried orange peel resource obtain simultaneously application, has effectively improved the quality of product and the comprehensive utilization ratio of resource.
Chen Yu has reported that in " extraction of Yellow Pigment from Tangerine Peel and stability " document take 95 % ethanol as extraction agent, solid-liquid ratio is 1: 8(g/mL), extract 6 h under 60 ℃, its extraction effect is better, but its pigment content is not high.Yellow Pigment from Tangerine Peel is more stable under acid and weak basic condition, and common food additive, oxygenant, reductive agent are not obvious to its stability influence, and stronger resistance to oxidation reducing power is arranged.
Li Youji has reported that in " Yellow Pigment from Tangerine Peel Study on extraction " document it is 1 at 65 ℃, solid-liquid ratio that orange peel adopts dehydrated alcohol: 8(g/mL), pH is 5. 0 times lixiviate 5h, obtain its extracting solution, filter to get filtrate, repeat once, merging filtrate, centrifugal removal of impurities gets supernatant liquor, concentrate to get thick yellow pigment, refining finished product through vacuum-drying again.
Jia Changying has reported take 70% ethanol as extraction agent in " Extraction Technology of Yellow Pigment from Orange Peel research " document, adopts the solid-liquid ratio of 1: 8 (g/mL), and dipping is 3 times under the dipping temperature of 50 ℃, and each 5h needs 15h altogether; Adopt soxhlet extraction, with extraction solvent and the solid-liquid ratio identical with pickling process, under 95 ℃ of bath temperatures, only need backflow 2h just can reach the extraction effect of pickling process, shortened extraction time significantly.Practical problems in its commercial process is not considered in extraction for Yellow Pigment in Tangerine Peel, and high temperature is too large to the demand of energy consumption, and the ethanol of high density is too high to the requirement of extraction equipment, also easily blasts, and is larger to the risk of pollution of environment.Also have report to adopt microwave extracting to carry out the extraction of Yellow Pigment in Tangerine Peel, but microwave extracting equipment can't carry out suitability for industrialized production at present.
Yellow Pigment in Tangerine Peel content in dried orange peel is the highest, and Hesperidin also has certain content in dried orange peel, draws materials conveniently, and is widely distributed, low price.Present disclosed documents and materials fail its effective constituent in leaching process is carried out comprehensive development and utilization, thereby dried orange peel is carried out comprehensive deep processing mean a great, and explore and extract simultaneously orange yellow pigment and Hesperidin from dried orange peel, and its meaning is quite long-range.
Summary of the invention
The technical solution used in the present invention comprises: dry dried orange peel later through with acid alcohol refluxing extraction, filtration, concentrate, neutralize, refilter, filter residue adds alkali dissolution, neutralization, crystallization make the hesperidine sterling.Filtrate adds alcohol extraction, makes the Yellow Pigment in Tangerine Peel sterling after concentrate drying.
Therefore, the invention provides a kind of method of extracting Yellow Pigment in Tangerine Peel and hesperidine from tangerine peel, step comprises:
(1) pulverize dry dried orange peel, and with dried orange peel, 45% aqueous ethanolic solution by weight (kg)/volume ratio (L)=1:3-5 mix, 40 ℃ of refluxing extraction;
(2) after ceramic membrane filter once removed the gred, filtrate was evaporated to the 1/5-1/8 of original volume;
(3) concentrated solution is regulated pH to 7 left and right with the 0.01mol/L hydrochloric acid soln, more than standing 5h, once obtain filter residue through ceramic membrane filter.
(4) filter residue is dissolved with 0.001mol/LNaOH solution, filter residue and 0.001mol/LNaOH solution is (kg)/volume ratio (L)=1:3-4 by weight;
(5) after ceramic membrane filter once removed the gred, filtrate was evaporated to the 1/5-1/8 of original volume, regulated pH to 7 left and right with the 0.01mol/L aqueous hydrochloric acid, more than standing 5h, obtained the Hesperidin sterling through ceramic membrane filter.
(6) with (3) filtrate that obtains of step, the ethyl acetate extraction with 2-3 times of volume discards ethyl acetate layer, and will not contain ethyl acetate layer and carry out concentrating under reduced pressure at 40 ℃, until obtain dry thing, is the Yellow Pigment in Tangerine Peel sterling.
In one embodiment, 45% aqueous ethanolic solution described in step (1) wherein contains 45% ethanol, the aqueous solution of 0.001mol/LNaOH.
Technique effect
1, in the inventive method, raw material, equipment used is common common raw material, equipment, has avoided in the commercial process having reduced widely its production cost for the dependence of expensive raw materials, instrument.
2, mandarin orange planting is easy, and output is high, price is low, convenient sources, and follow-up resource is secure.
3, use dried orange peel as extracting raw material, both greatly improved the utilising efficiency of dried orange peel, improved again the added value of dried orange peel.
4, the inventive method is simple to operate, has greatly reduced the production cost of Yellow Pigment in Tangerine Peel and hesperidine, has simplified its production process.
5, the present invention's reagent used is chemical reagent nontoxic, cheap, volume production, can utilize ripe reagent to reclaim routine techniques in whole process, has greatly reduced to the environmental emission waste.
Tool is stopped embodiment
Below, the present invention will be further detailed with embodiment, but it is not limited to any one or the similar example of these embodiment.
Embodiment 1
(1) select that in the dried immature fruit of citron orange, hesperidine content 5.14%, will take 100kg below dried immature fruit of citron orange crushed after being dried to 10 order, add the aqueous solution that contains 0.001mol/LNaOH, 45% ethanol of 400L to mix, 40 ℃ of refluxing extraction; (2) after ceramic membrane filter once removed the gred, filtrate was evaporated to 60L; (3) concentrated solution is regulated pH to 7 left and right with the 0.01mol/L hydrochloric acid soln, more than standing 5h, once obtain filter residue 13.4kg through ceramic membrane filter; (4) the NaOH solution of filter residue with the 0.001mol/L of 35L is dissolved; (5) after ceramic membrane filter once removed the gred, filtrate was evaporated to 6L, regulated pH to 7 left and right with the 0.01mol/L aqueous hydrochloric acid, more than standing 5h, obtained hesperidine sterling 3.85kg through ceramic membrane filter; (6) with (3) filtrate that obtains of step, the ethyl acetate extraction with 3 times of volumes discards ethyl acetate layer, and will not contain ethyl acetate layer and carry out concentrating under reduced pressure at 40 ℃, until obtain dry thing, is Yellow Pigment in Tangerine Peel sterling 2.45kg.Test set is the Agilent1100 high performance liquid chromatograph, chromatographic column is Hypersil ODS (250mm * 4.6mm, 5 μ), the testing conditions of hesperidine: moving phase is water: acetonitrile: acetic acid solution (80:16:4, V/V), detection wavelength are that 280nm, flow velocity are that l ml/min, sample size are 20 μ L; The spectrophotometry colorimetric detection condition of Yellow Pigment in Tangerine Peel: solubilising reagent is that ethanol, detection wavelength are 370nm.The purity of hesperidine sample is 95.54%, the purity of Yellow Pigment in Tangerine Peel sample is 97.25%.
Embodiment 2
(1) select that in the dried immature fruit of citron orange, hesperidine content 5.14%, will take 200kg below dried immature fruit of citron orange crushed after being dried to 10 order, add the aqueous solution that contains 0.001mol/LNaOH, 45% ethanol of 800L to mix, 40 ℃ of refluxing extraction; (2) after ceramic membrane filter once removed the gred, filtrate was evaporated to 100L; (3) concentrated solution is regulated pH to 7 left and right with the 0.01mol/L hydrochloric acid soln, more than standing 5h, once obtain filter residue 28.1kg through ceramic membrane filter; (4) the NaOH solution of filter residue with the 0.001mol/L of 60L is dissolved; (5) after ceramic membrane filter once removed the gred, filtrate was evaporated to 13L, regulated pH to 7 left and right with the 0.01mol/L aqueous hydrochloric acid, more than standing 5h, obtained hesperidine sterling 7.87kg through ceramic membrane filter; (6) with (3) filtrate that obtains of step, the ethyl acetate extraction with 2.5 times of volumes discards ethyl acetate layer, and will not contain ethyl acetate layer and carry out concentrating under reduced pressure at 40 ℃, until obtain dry thing, is Yellow Pigment in Tangerine Peel sterling 4.96kg.Detection method by embodiment 1 detects hesperidine and Yellow Pigment in Tangerine Peel sample, and the purity of hesperidine sample is 96.25%, the purity of Yellow Pigment in Tangerine Peel sample is 97.62%.
Embodiment 3
(1) select that in the dried immature fruit of citron orange, hesperidine content 5.14%, will take 400kg below dried immature fruit of citron orange crushed after being dried to 10 order, add the aqueous solution that contains 0.001mol/LNaOH, 45% ethanol of 1400L to mix, 40 ℃ of refluxing extraction; (2) after ceramic membrane filter once removed the gred, filtrate was evaporated to 200L; (3) concentrated solution is regulated pH to 7 left and right with the 0.01mol/L hydrochloric acid soln, more than standing 5h, once obtain filter residue 54.5kg through ceramic membrane filter; (4) the NaOH solution of filter residue with the 0.001mol/L of 120L is dissolved; (5) after ceramic membrane filter once removed the gred, filtrate was evaporated to 20L, regulated pH to 7 left and right with the 0.01mol/L aqueous hydrochloric acid, more than standing 5h, obtained hesperidine sterling 15.78kg through ceramic membrane filter; (6) with (3) filtrate that obtains of step, the ethyl acetate extraction with 3 times of volumes discards ethyl acetate layer, and will not contain ethyl acetate layer and carry out concentrating under reduced pressure at 40 ℃, until obtain dry thing, is Yellow Pigment in Tangerine Peel sterling 9.94kg.Detection method by embodiment 1 detects hesperidine and Yellow Pigment in Tangerine Peel sample, and the purity of hesperidine sample is 98.36%, the purity of Yellow Pigment in Tangerine Peel sample is 97.29%.
Claims (3)
1. the invention provides a kind of method of extracting Yellow Pigment in Tangerine Peel and hesperidine from tangerine peel, step comprises:
(1) pulverize dry dried orange peel, and with dried orange peel, aqueous ethanolic solution by weight (kg)/volume ratio (L)=1:3-5 mix, 40 ℃ of refluxing extraction;
(2) after ceramic membrane filter once removed the gred, filtrate was evaporated to the 1/5-1/8 of original volume;
(3) concentrated solution is regulated pH to 7 left and right with the 0.01mol/L hydrochloric acid soln, more than standing 5h, once obtain filter residue through ceramic membrane filter;
(4) filter residue is dissolved with 0.001mol/LNaOH solution, filter residue and 0.001mol/LNaOH solution is (kg)/volume ratio (L)=1:3-4 by weight;
(5) after ceramic membrane filter once removed the gred, filtrate was evaporated to the 1/5-1/8 of original volume, regulated pH to 7 left and right with the 0.01mol/L aqueous hydrochloric acid, more than standing 5h, obtained the Hesperidin sterling through ceramic membrane filter;
(6) with (3) filtrate that obtains of step, the ethyl acetate extraction with 2-3 times of volume discards ethyl acetate layer, and will not contain ethyl acetate layer and carry out concentrating under reduced pressure at 40 ℃, until obtain dry thing, is the Yellow Pigment in Tangerine Peel sterling.
2. according to claim 1 method, aqueous ethanolic solution described in step (1) wherein contains 45% ethanol, the aqueous solution of 0.001mol/LNaOH.
3. according to claim 1 method, filter described in step (2), (3), (5), refers to adopt the ceramic membrane filter of 0.2 μ m pore size once.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483403A (en) * | 2013-09-24 | 2014-01-01 | 重庆主流生物工程有限公司 | Circulating extraction method for extracting and purifying hesperidin from orange residues |
| CN104402952A (en) * | 2014-12-15 | 2015-03-11 | 晨光生物科技集团股份有限公司 | Method for extracting mandarin oil and hesperidin from orange peel |
| CN104403357A (en) * | 2014-10-29 | 2015-03-11 | 宁波广源纺织品有限公司 | Orange peel vegetable dye extraction method |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150038A (en) * | 1977-05-16 | 1979-04-17 | Dynapol | Conversion of hesperidin into hesperetin |
| WO2000032062A1 (en) * | 1998-12-02 | 2000-06-08 | Adumim Chemicals Ltd. | A method for selectively obtaining antioxidant rich extracts from citrus fruits |
| EP1157701A1 (en) * | 1999-12-23 | 2001-11-28 | ASAC Compania de Biotecnologia E Investigacion, S.A. | Method for obtaining olive leaf extracts and applications thereof |
| CN101265283A (en) * | 2008-04-22 | 2008-09-17 | 复旦大学 | Method for extracting hesperidin and naringin |
| CN101643489A (en) * | 2009-05-26 | 2010-02-10 | 苏州派腾生物医药科技有限公司 | Process for preparing hesperidin |
| CN101704867A (en) * | 2009-11-03 | 2010-05-12 | 国家***第三海洋研究所 | Method for preparing naringin or hesperidin |
| CN101747394A (en) * | 2009-12-31 | 2010-06-23 | 浙江工业大学 | Method for extracting hesperidin from tangerine peel |
-
2013
- 2013-01-30 CN CN201310036105.8A patent/CN103113438B/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150038A (en) * | 1977-05-16 | 1979-04-17 | Dynapol | Conversion of hesperidin into hesperetin |
| WO2000032062A1 (en) * | 1998-12-02 | 2000-06-08 | Adumim Chemicals Ltd. | A method for selectively obtaining antioxidant rich extracts from citrus fruits |
| EP1157701A1 (en) * | 1999-12-23 | 2001-11-28 | ASAC Compania de Biotecnologia E Investigacion, S.A. | Method for obtaining olive leaf extracts and applications thereof |
| CN101265283A (en) * | 2008-04-22 | 2008-09-17 | 复旦大学 | Method for extracting hesperidin and naringin |
| CN101643489A (en) * | 2009-05-26 | 2010-02-10 | 苏州派腾生物医药科技有限公司 | Process for preparing hesperidin |
| CN101704867A (en) * | 2009-11-03 | 2010-05-12 | 国家***第三海洋研究所 | Method for preparing naringin or hesperidin |
| CN101747394A (en) * | 2009-12-31 | 2010-06-23 | 浙江工业大学 | Method for extracting hesperidin from tangerine peel |
Non-Patent Citations (1)
| Title |
|---|
| 贾长英，等: "桔皮黄色素提取工艺研究", 《化工技术与开发》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103483403A (en) * | 2013-09-24 | 2014-01-01 | 重庆主流生物工程有限公司 | Circulating extraction method for extracting and purifying hesperidin from orange residues |
| CN103483403B (en) * | 2013-09-24 | 2016-03-09 | 重庆主流生物工程有限公司 | A kind of circulation extracting method of hesperidine of purifying from tangerine slag |
| CN104403357A (en) * | 2014-10-29 | 2015-03-11 | 宁波广源纺织品有限公司 | Orange peel vegetable dye extraction method |
| CN104402952A (en) * | 2014-12-15 | 2015-03-11 | 晨光生物科技集团股份有限公司 | Method for extracting mandarin oil and hesperidin from orange peel |
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