CN113735919A - Method for preparing naringin dihydrochalcone sweetener by adding hydrogen into pummelo peel extract and prepared naringin dihydrochalcone sweetener - Google Patents
Method for preparing naringin dihydrochalcone sweetener by adding hydrogen into pummelo peel extract and prepared naringin dihydrochalcone sweetener Download PDFInfo
- Publication number
- CN113735919A CN113735919A CN202111139307.6A CN202111139307A CN113735919A CN 113735919 A CN113735919 A CN 113735919A CN 202111139307 A CN202111139307 A CN 202111139307A CN 113735919 A CN113735919 A CN 113735919A
- Authority
- CN
- China
- Prior art keywords
- naringin
- pummelo peel
- naringin dihydrochalcone
- preparing
- extraction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000001183 FEMA 4495 Substances 0.000 title claims abstract description 67
- CWBZAESOUBENAP-QVNVHUMTSA-N Naringin dihydrochalcone Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C(O)C(C(=O)CCC=3C=CC(O)=CC=3)=C(O)C=2)O[C@H](CO)[C@@H](O)[C@@H]1O CWBZAESOUBENAP-QVNVHUMTSA-N 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 title claims abstract description 67
- 239000000284 extract Substances 0.000 title claims abstract description 58
- 235000001759 Citrus maxima Nutrition 0.000 title claims abstract description 57
- 244000276331 Citrus maxima Species 0.000 title claims abstract description 57
- 235000003599 food sweetener Nutrition 0.000 title claims abstract description 44
- 239000003765 sweetening agent Substances 0.000 title claims abstract description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 title claims description 12
- 239000001257 hydrogen Substances 0.000 title claims description 12
- 239000001606 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one Substances 0.000 claims abstract description 66
- DFPMSGMNTNDNHN-ZPHOTFPESA-N naringin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](OC=2C=C3O[C@@H](CC(=O)C3=C(O)C=2)C=2C=CC(O)=CC=2)O[C@H](CO)[C@@H](O)[C@@H]1O DFPMSGMNTNDNHN-ZPHOTFPESA-N 0.000 claims abstract description 66
- 229930019673 naringin Natural products 0.000 claims abstract description 66
- 229940052490 naringin Drugs 0.000 claims abstract description 66
- 239000002904 solvent Substances 0.000 claims abstract description 64
- 238000000605 extraction Methods 0.000 claims abstract description 63
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 61
- 230000005496 eutectics Effects 0.000 claims abstract description 57
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 25
- 238000007142 ring opening reaction Methods 0.000 claims abstract description 24
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims abstract description 15
- 235000019743 Choline chloride Nutrition 0.000 claims abstract description 15
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims abstract description 15
- 229960003178 choline chloride Drugs 0.000 claims abstract description 15
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 17
- 239000013078 crystal Substances 0.000 claims description 16
- 239000003513 alkali Substances 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 238000007710 freezing Methods 0.000 claims description 13
- 230000008014 freezing Effects 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 11
- 238000001694 spray drying Methods 0.000 claims description 11
- 239000006228 supernatant Substances 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 8
- 230000035484 reaction time Effects 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000004108 freeze drying Methods 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- IXVXIWLKOMVSFY-GOZPEMRWSA-N naringin chalcone Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C=C1O)=CC(O)=C1C(=O)\C=C\C1=CC=C(O)C=C1 IXVXIWLKOMVSFY-GOZPEMRWSA-N 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 238000005303 weighing Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 abstract description 34
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 235000021185 dessert Nutrition 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 230000000052 comparative effect Effects 0.000 description 18
- 239000012295 chemical reaction liquid Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 6
- 238000001514 detection method Methods 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000009776 industrial production Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- QGGZBXOADPVUPN-UHFFFAOYSA-N dihydrochalcone Chemical compound C=1C=CC=CC=1C(=O)CCC1=CC=CC=C1 QGGZBXOADPVUPN-UHFFFAOYSA-N 0.000 description 2
- PXLWOFBAEVGBOA-UHFFFAOYSA-N dihydrochalcone Natural products OC1C(O)C(O)C(CO)OC1C1=C(O)C=CC(C(=O)CC(O)C=2C=CC(O)=CC=2)=C1O PXLWOFBAEVGBOA-UHFFFAOYSA-N 0.000 description 2
- 229930003935 flavonoid Natural products 0.000 description 2
- 235000017173 flavonoids Nutrition 0.000 description 2
- 150000002215 flavonoids Chemical class 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 238000009210 therapy by ultrasound Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical group OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 239000001329 FEMA 3811 Substances 0.000 description 1
- YALCGCHVWZLREG-UHFFFAOYSA-N Hesperetin-dihydrochalkon-glucosid Natural products C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1OC1C(O)C(O)C(O)C(CO)O1 YALCGCHVWZLREG-UHFFFAOYSA-N 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000006189 buccal tablet Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 150000002214 flavonoid derivatives Chemical class 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013611 frozen food Nutrition 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 235000015094 jam Nutrition 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ITVGXXMINPYUHD-CUVHLRMHSA-N neohesperidin dihydrochalcone Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C(C(=C1)O)=C(O)C=C1O[C@H]1[C@H](O[C@H]2[C@@H]([C@H](O)[C@@H](O)[C@H](C)O2)O)[C@@H](O)[C@H](O)[C@@H](CO)O1 ITVGXXMINPYUHD-CUVHLRMHSA-N 0.000 description 1
- 229940089953 neohesperidin dihydrochalcone Drugs 0.000 description 1
- 235000010434 neohesperidine DC Nutrition 0.000 description 1
- 235000019520 non-alcoholic beverage Nutrition 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 235000019640 taste Nutrition 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Classifications
-
- 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
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- 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
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application relates to the technical field of dessert preparation, and particularly discloses a method for preparing a naringin dihydrochalcone sweetener by hydrogenating an exocarpium citri grandis extract and the prepared naringin dihydrochalcone sweetener, wherein the method comprises the following steps: extraction: extracting naringin from the crushed pummelo peel by using a eutectic solvent to obtain a naringin extracting solution; ring opening and hydrogenation are carried out to obtain naringin dihydrochalcone; wherein, the adopted eutectic solvent is selected from the following components in a molar ratio of 1: (1-1.5): (0.5-1) choline chloride, acetic acid and polyhydric alcohol; the naringin dihydrochalcone sweetener disclosed in the application is prepared by the method, the application has the advantages that the naringin dihydrochalcone sweetener is extracted from pummelo peel and prepared, the extraction rate is higher, and the industrialized production is facilitated.
Description
Technical Field
The application relates to the technical field of sweetener preparation, in particular to a method for preparing a naringin dihydrochalcone sweetener by hydrogenating an exocarpium citri grandis extract and the prepared naringin dihydrochalcone sweetener.
Background
In recent years, dihydrochalcone sweeteners have become one of the most attractive sweeteners, and include neohesperidin dihydrochalcone, naringin dihydrochalcone, and hesperetin dihydrochalcone-4' - β -D-glucoside. Wherein naringin dihydrochalcone is a flavonoid derivative obtained by hydrogenating naringin extracted from natural citrus plant as a novel sweetener.
Compared with sucrose, the sweetness of naringin dihydrochalcone is 700 times that of sucrose, has the characteristics of high sweetness, low calorific value, no toxicity, safety and the like, and can be applied to food, medicine and daily chemical industry. And because the taste is fresh and cool, the aftertaste is lasting, and the product has special faint scent, has excellent effect of shielding bitter taste, and is particularly suitable for dairy products, fat and grease, frozen foods, processed vegetables, jelly, jam, alcohol-free beverages, chewing gum, toothpaste and buccal tablets.
Researches find that pummelo peel contains rich active ingredients such as polysaccharides, volatile oils and flavonoids, wherein the main ingredient of the flavonoids is naringin which accounts for more than 80% of the total flavone content, so that extraction and preparation of the naringin dihydrochalcone sweetener from the pummelo peel has important exploration significance. However, currently, few researches and descriptions are related, and the naringin extracted from pummelo peel mainly adopts organic solvents such as ethanol, acetone and the like, but the extraction rate is low, so that a new method for extracting pummelo peel and preparing the naringin dihydrochalcone sweetener is needed.
Disclosure of Invention
In order to extract and prepare the naringin dihydrochalcone sweetener from pummelo peel, the extraction rate is higher, and the industrial production is facilitated, the application provides a method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract and the prepared naringin dihydrochalcone sweetener.
In a first aspect, the method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract adopts the following technical scheme:
a method for preparing naringin dihydrochalcone sweetener by hydrogenating pummelo peel extract comprises the following steps:
extraction: extracting naringin from the crushed pummelo peel by using a eutectic solvent to obtain a naringin extracting solution;
ring opening and hydrogenation: performing ring opening on naringin by adopting an alkali substance to obtain naringin chalcone, and then hydrogenating the obtained naringin chalcone to obtain naringin dihydrochalcone;
wherein, the feed-liquid ratio of the crushed pummelo peel and the eutectic solvent in the extraction step is 1 (15-20), and the molar ratio of the adopted eutectic solvent is 1: (1-1.5): (0.5-1) choline chloride, acetic acid and polyhydric alcohol.
Through adopting above-mentioned technical scheme, the method that this application provided at first extracts and obtains naringin from pummelo peel smashing thing, then the ring-opening, hydrogenation finally obtains naringin dihydrochalcone sweetener, pummelo peel smashing thing adopts the eutectic solvent of specific proportion system to extract in this application, the applicant finds that it compares in traditional organic solvent and extracts, the extraction rate is higher, and easy operation is more favorable to the industrial production, and eutectic solvent is as novel green solvent moreover, adopt eutectic solvent to extract more green environmental protection.
Optionally, the eutectic solvent is prepared by the following method:
weighing choline chloride, acetic acid and polyalcohol at a molar ratio, heating at 70-80 deg.C, stirring for 1.5-2 hr to obtain transparent and uniform solvent.
Optionally, in the extraction step, the deep-eutectic solvent extraction of naringin from the crushed pummelo peel is carried out under the ultrasonic condition, and the ultrasonic power is 80-100 w.
By adopting the technical scheme, the extraction of the deep eutectic solvent is assisted by ultrasonic treatment in the application, the extraction time and the extraction temperature are obviously shortened, the naringin extraction yield is higher, and the industrialized production is more favorably realized.
Optionally, in the extraction step, the extraction time is 60-80min, and the extraction temperature is 30-40 ℃.
By adopting the technical scheme, when the extraction time and the extraction temperature parameters are adopted, the extraction rate of naringin is better, the extraction temperature is low, and the extraction time is short.
Optionally, the polyol is selected from any one of ethylene glycol, glycerol, butanediol and 1, 6-hexanediol, and more preferably 1, 6-hexanediol.
Optionally, the extracting step further comprises: centrifuging naringin extract obtained by extraction with eutectic solvent at the rotating speed of 2000-4000r/min, taking supernatant, concentrating to obtain extract with the relative density of 1.1-1.2 at 60 ℃, spray drying, adding water into the extract for crystallization, filtering to obtain crystals, filtering and drying the crystals to obtain naringin.
Optionally, the cooling specifically comprises: and cooling the extract after spray drying, wherein the cooling operation comprises the following specific steps: the specific operation of cooling after spray drying is as follows: pre-freezing at (-25) ° C to (-10) ° C for 3-4h, and freeze-drying under the following conditions: freezing for 22-24h at (-30) - (-20) deg.C under vacuum degree of 10Pa, cooling, and crystallizing with water.
By adopting the technical scheme, the applicant finds that the operations of pre-freezing and freezing after the extract is spray-dried can have a certain regulation and control effect on the pores of the substances in the extract, and the naringin yield is higher after the crystal is separated out after the extract is frozen.
Optionally, the ring opening and hydrogenation operations are as follows: dissolving the prepared naringin in alkali liquor, opening the ring, adding a palladium-carbon catalyst, introducing hydrogen for hydrogenation reaction, filtering, adjusting the filtrate to be neutral, standing for 40-48h, filtering, and taking out crystals to obtain a naringin dihydrochalcone crude product;
and dissolving the crude naringin dihydrochalcone product by using ethanol, adding active carbon into the dissolved solution for decoloring, filtering, cooling and crystallizing, filtering to obtain crystals, and drying in vacuum to obtain the naringin dihydrochalcone.
By adopting the technical scheme, firstly, naringin is subjected to ring opening in alkali liquor, then hydrogenation reduction is carried out to obtain dihydrochalcone, then filtration crystallization is carried out, and then decoloration treatment is carried out to obtain a high-purity naringin dihydrochalcone finished product.
Optionally, the hydrogenation reaction parameters are as follows: the hydrogenation reaction temperature is 50-60 deg.C, the reaction time is 4-8h, the hydrogen pressure is 0.5-2.0Mpa, and the pH of the reaction solution is 12-13.
By adopting the technical scheme, the yield of the naringin dihydrochalcone obtained under the reaction conditions is higher, and especially the pH value of the reaction liquid is set, probably because the pH value of the reaction liquid is too low, the solubility of naringin in the reaction liquid is lower, the reaction cannot be completely carried out, the pH value is too high, and the glycosidic bond on the naringin is broken, so that the yield is lower.
In a second aspect, the application provides a naringin dihydrochalcone sweetener prepared by the method, and the following technical scheme is adopted:
a naringin dihydrochalcone sweetener obtained by the method is provided.
In summary, the present application has the following beneficial effects:
1. the naringin in the method is extracted from the crushed pummelo peel by adopting the eutectic solvent with a specific proportion system, compared with the traditional organic solvent extraction, the naringin has higher extraction rate, is simple to operate and more beneficial to industrial production, and the eutectic solvent is used as a novel green solvent, so that the extraction by adopting the eutectic solvent is more green and environment-friendly;
2. according to the application, the extraction of the eutectic solvent is assisted by ultrasonic treatment, so that the extraction time and the extraction temperature are obviously shortened, the naringin extraction yield is higher, and the industrial production is more favorably realized;
3. the operation of prefreezing and freezing is carried out again to the extract spray drying that obtains among the naringin extraction process of this application, probably has certain regulation and control effect to the interior matter hole of extract, freezes the back and adds crystal and separates out, and the naringin yield that obtains is higher.
Detailed Description
The present application is further described in detail with reference to the following examples, which are specifically illustrated by the following: the following examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer, and the starting materials used in the following examples are available from ordinary commercial sources unless otherwise specified.
The crushed pummelo peel can be obtained by slicing and crushing common pummelo peel plants in the field after softening, or can be obtained by directly obtaining common commercially available pummelo peel raw powder, and the crushed pummelo peel in the following embodiments is obtained by crushing softened slices, and the softening parameters are as follows: steaming exocarpium Citri Grandis with water vapor at 60 deg.C for 1 hr, slicing to 4mm thickness, and pulverizing to obtain exocarpium Citri Grandis powder with particle size of 100 mesh.
Preparation example of eutectic solvent
Preparation example 1
A preparation method of a eutectic solvent comprises the following steps:
mixing choline chloride, acetic acid and ethylene glycol according to the weight ratio of 1: 1: weighing at a molar ratio of 0.5, heating in a water bath at 70 deg.C, and stirring for 2 hr to obtain transparent and uniform solvent.
Preparation example 2
A preparation method of a eutectic solvent comprises the following steps:
mixing choline chloride, acetic acid and 1, 6-hexanediol in a ratio of 1: 1.2: weighing at a molar ratio of 0.8, heating in a water bath at 75 deg.C, and stirring for 1.5 hr to obtain transparent and uniform solvent.
Preparation example 3
A preparation method of a eutectic solvent comprises the following steps:
mixing choline chloride, acetic acid and glycerol according to the weight ratio of 1: 1.5: 1, heating in a water bath kettle at 80 ℃, and stirring for 1.5 hours to obtain a transparent and uniform solvent.
Preparation example 4
A method for preparing a eutectic solvent according to the method of preparation example 2, except that choline chloride, acetic acid and glycerin are mixed in the ratio of 1: 1.5: 1 by mole ratio.
Preparation example 5
A method for preparing a eutectic solvent was performed as in preparation example 2, except that an equimolar amount of 1, 6-hexanediol was replaced with butanediol.
Comparative preparation example 1
A method for preparing a eutectic solvent was performed according to the method of preparation example 2, except that butanediol was not added to the raw materials, and the molar ratio of choline chloride to acetic acid was the same as that of preparation example 2.
Comparative preparation example 2
A method for preparing a eutectic solvent was carried out according to the method of preparation example 2, except that acetic acid was not added to the raw materials, and the molar ratio of choline chloride to acetic acid was the same as that of preparation example 2.
Comparative preparation example 3
A method for preparing a eutectic solvent according to the method of preparation example 2, except that acetic acid is equivalently replaced with malic acid.
Comparative preparation example 4
A method for preparing a eutectic solvent according to the method of preparation example 2, except that acetic acid was replaced with citric acid in equal amounts.
Comparative preparation example 5
A method for preparing a eutectic solvent according to the method of preparation example 2, except that acetic acid was equivalently replaced with thiourea.
Comparative preparation example 6
A method for preparing a eutectic solvent was performed as in preparation example 2, except that acetic acid was replaced with urea in equal amounts.
Example 1
A method for preparing naringin dihydrochalcone sweetener by hydrogenating pummelo peel extract comprises the following steps:
s1 extraction:
s1-1: taking 10g of crushed pummelo peel, and extracting naringin from the crushed pummelo peel by using the eutectic solvent prepared in preparation example 1 to obtain a naringin extracting solution, wherein the material-liquid ratio of the crushed pummelo peel to the eutectic solvent is 1:15, the extraction time is 60min, and the extraction temperature is 40 ℃;
s1-2: centrifuging naringin extract obtained by extraction with eutectic solvent at 2000r/min, collecting supernatant, concentrating the supernatant to obtain extract with relative density of 1.1 at 60 deg.C, spray drying the extract, prefreezing the dried product at (-25) deg.C for 4 hr, and freeze drying under the following conditions: freezing for 22h at (-30) deg.C under vacuum degree of 10Pa, adding water into the cooled product system for crystallization at a volume ratio of extract to water of 1:3, and filtering and drying to obtain naringin;
ring opening and hydrogenation of S2:
s2-1: dissolving the prepared naringin in sodium hydroxide alkali liquor, and carrying out ring-opening reaction, wherein the mass ratio of the naringin to the sodium hydroxide is 3: 1, dissolving sodium hydroxide in water to obtain a sodium hydroxide alkali liquor, and controlling the pH value of the alkali liquor to be 12; the ring-opening reaction temperature is 40 ℃, the ring-opening reaction time is 90min, and the ring-opening reaction is carried out at the rotating speed of 500 r/min;
s2-2: then adjusting the pH value of the reaction liquid to 12, adding a palladium-carbon catalyst into the reaction liquid, wherein the dosage of the catalyst is 3 wt% of the naringin, introducing hydrogen to carry out hydrogenation reaction, wherein the pressure of the hydrogen is 0.5Mpa, the hydrogenation reaction temperature is 50 ℃, and the reaction time is 8 hours;
s2-3: then filtering the reaction liquid after hydrogenation reaction, adjusting the filtrate to be neutral, standing for 40h, filtering out crystals to obtain a naringin dihydrochalcone crude product;
s2-4: and then dissolving the obtained crude naringin dihydrochalcone product in 15 wt% ethanol with the mass of 6 times, adding activated carbon into the dissolved solution, wherein the added mass of the activated carbon is 3 wt% of the reaction solution, decoloring for 20min, filtering, cooling and crystallizing, filtering to obtain crystals, and drying in vacuum to obtain the finished naringin dihydrochalcone product.
Example 2
A method for preparing naringin dihydrochalcone sweetener by hydrogenating pummelo peel extract comprises the following steps:
s1 extraction:
s1-1: taking 10g of crushed pummelo peel, and extracting naringin from the crushed pummelo peel by using the eutectic solvent prepared in the preparation example 2 to obtain a naringin extracting solution, wherein the material-liquid ratio of the crushed pummelo peel to the eutectic solvent is 1:18, the extraction time is 70min, and the extraction temperature is 35 ℃;
s1-2: centrifuging naringin extract obtained by extraction with eutectic solvent at 3000r/min, collecting supernatant, concentrating the supernatant into extract with relative density of 1.1-1.2 at 60 deg.C, spray drying, pre-freezing the dried product at (-15) deg.C for 3.5 hr, and freeze drying under the conditions of: freezing for 23h at (-25) deg.C under vacuum degree of 10Pa, adding water into the cooled product system for crystallization at a volume ratio of extract to water of 1:4, and filtering and drying to obtain naringin;
ring opening and hydrogenation of S2:
s2-1: dissolving the prepared naringin in sodium hydroxide alkali liquor, and carrying out ring-opening reaction, wherein the mass ratio of the naringin to the sodium hydroxide is 3: 1.5, dissolving sodium hydroxide in water to obtain a sodium hydroxide alkali liquor, and controlling the pH value of the alkali liquor to be 13; the ring-opening reaction temperature is 40 ℃, the ring-opening reaction time is 70min, and the ring-opening reaction is carried out at the rotating speed of 400 r/min;
s2-2: then adjusting the pH value of the reaction liquid to 13, adding a palladium-carbon catalyst into the reaction liquid, wherein the dosage of the catalyst is 5 wt% of the naringin, introducing hydrogen to carry out hydrogenation reaction, wherein the hydrogen pressure is 1.0Mpa, the hydrogenation reaction temperature is 55 ℃, and the reaction time is 6 hours;
s2-3: then filtering the reaction liquid after hydrogenation reaction, adjusting the filtrate to be neutral, standing for 42h, filtering out crystals to obtain a naringin dihydrochalcone crude product;
s2-4: and then dissolving the obtained crude naringin dihydrochalcone product in 15 wt% ethanol with the mass of 6 times, adding activated carbon into the dissolved solution, wherein the added mass of the activated carbon is 4 wt% of the reaction solution, decoloring for 25min, filtering, cooling and crystallizing, filtering to obtain crystals, and drying in vacuum to obtain the finished naringin dihydrochalcone product.
Example 3
A method for preparing naringin dihydrochalcone sweetener by hydrogenating pummelo peel extract comprises the following steps:
s1 extraction:
s1-1: taking 10g of crushed pummelo peel, and extracting naringin from the crushed pummelo peel by using the eutectic solvent prepared in preparation example 3 to obtain a naringin extracting solution, wherein the material-liquid ratio of the crushed pummelo peel to the eutectic solvent is 1:20, the extraction time is 80min, and the extraction temperature is 30 ℃;
s1-2: centrifuging naringin extract obtained by extraction with eutectic solvent at rotation speed of 4000r/min, collecting supernatant, concentrating the supernatant to obtain extract with relative density of 1.2 at 60 deg.C, spray drying, prefreezing the dried product at (-10) deg.C for 3 hr, and freeze drying under the following conditions: freezing for 24h at (-20) deg.C under vacuum degree of 10Pa, adding water into the cooled product system for crystallization at a volume ratio of extract to water of 1:4, and filtering and drying to obtain naringin;
ring opening and hydrogenation of S2:
s2-1: dissolving the prepared naringin in sodium hydroxide alkali liquor, and carrying out ring-opening reaction, wherein the mass ratio of the naringin to the sodium hydroxide is 3: 2, dissolving sodium hydroxide in water to obtain a sodium hydroxide alkali liquor, and controlling the pH value of the alkali liquor to be 13; the ring-opening reaction temperature is 45 ℃, the ring-opening reaction time is 60min, and the ring-opening reaction is carried out at the rotating speed of 500 r/min;
s2-2: then adjusting the pH value of the reaction liquid to 13, adding a palladium-carbon catalyst into the reaction liquid, wherein the dosage of the catalyst is 7 wt% of the naringin, introducing hydrogen to carry out hydrogenation reaction, wherein the hydrogen pressure is 2.0Mpa, the hydrogenation reaction temperature is 60 ℃, and the reaction time is 4 hours;
s2-3: then filtering the reaction liquid after hydrogenation reaction, adjusting the filtrate to be neutral, standing for 48h, filtering and taking crystals to obtain a naringin dihydrochalcone crude product;
s2-4: and then dissolving the obtained crude naringin dihydrochalcone product in 15 wt% ethanol with the mass of 6 times, adding active carbon into the dissolved solution, wherein the mass of the active carbon is 5 wt% of that of the reaction solution, decoloring for 30min, filtering, cooling and crystallizing, filtering to obtain crystals, and drying in vacuum to obtain the finished naringin dihydrochalcone product.
Example 4
A method for preparing a naringin dihydrochalcone sweetener by hydrogenating an exocarpium Citri Grandis extract is carried out according to the method in the example 2, except that:
in the step S1-1, the extraction of naringin in the crushed pummelo peel by the eutectic solvent is carried out under the ultrasonic condition, and the ultrasonic power is 80 w.
Namely: the specific operation of S1-1 is as follows: taking 10g of crushed pummelo peel, adding the eutectic solvent prepared in the preparation example 2, wherein the material-liquid ratio of the crushed pummelo peel to the eutectic solvent is 1:18, and putting the pummelo peel into an ultrasonic instrument, wherein the ultrasonic power is 80w, and the temperature is 35 ℃. The extraction time is 70 min.
Example 5
A method for preparing a naringin dihydrochalcone sweetener by hydrogenating an exocarpium Citri Grandis extract is carried out according to the method in the example 4, except that:
in the step S1-1, the extraction of naringin in the crushed pummelo peel by the eutectic solvent is carried out under the ultrasonic condition, and the ultrasonic power is 100 w.
Example 6
A method for preparing a naringin dihydrochalcone sweetener by hydrogenating an exocarpium Citri Grandis extract is carried out according to the method in the example 5, except that:
in the step S1-2, directly freezing at (-25) DEG C for 23h after spray drying, then adding water into a cooled product system for crystallization, wherein the volume ratio of the extract to the water is 1:4, the crystallization is completed under the refrigeration condition of 4 ℃, and after the crystallization is completed, filtering and drying are carried out to obtain the naringin.
Example 7
A method for preparing a naringin dihydrochalcone sweetener by hydrogenating an exocarpium Citri Grandis extract is carried out according to the method in the example 5, except that:
s1-2, concentrating the supernatant to obtain an extract, directly adding water into the extract for crystallization to obtain the pummelo peel glucoside, wherein the volume ratio of the extract to the water is 1:4, the crystallization is finished under the refrigeration condition of 4 ℃, and the pummelo peel glucoside is obtained after the crystallization is finished and the filtration and drying are carried out.
Examples 8 to 11
A method for preparing naringin dihydrochalcone sweetener by hydrogenating pummelo peel extract is carried out according to the method in the embodiment 5, wherein the difference is that the eutectic solvents adopted in the step S1-1 are the eutectic solvents respectively adopted in the preparation examples 1 and 3-5.
Comparative example
Comparative examples 1 to 6
A method for preparing naringin dihydrochalcone sweetener by hydrogenating pummelo peel extract is carried out according to the method in example 5, except that the eutectic solvent used in the step S1-1 is the eutectic solvent used in the comparative preparation examples 1-6.
Comparative example 7
A method for preparing naringin dihydrochalcone sweetener by hydrogenating pummelo peel extract is carried out according to the method in example 5, except that in step S1-1, the eutectic solvent is equivalently replaced by 40 vol% ethanol.
Performance detection
Measuring the naringin content of the supernatant obtained after centrifugation in the step S1-2 in the above examples and comparative examples by HPLC, then dissolving the naringin finally obtained in the step S1-2 in an ethanol solution with the volume concentration of 40%, wherein the addition amount of the ethanol solution is the same as that of the low eutectic solvent in the step S1-1, and then measuring the naringin content (wt%) by HPLC; the naringin dihydrochalcone yield finally obtained in the step S2-4 was detected, and the detection results are shown in table 1 below.
Table 1:
in addition, the purity of naringin obtained in the step S1 and naringin dihydrochalcone obtained in the step S2 in the above examples and comparative examples are tested, and the purity of naringin obtained in the examples of the present application is more than 95.5%, while the purity of naringin in comparative examples 1 to 6 is 94.5 to 95.8%, and the purity of naringin in comparative example 7 is 95.3%. The purity of the naringin dihydrochalcone in the step S2 of the embodiment and the comparative example reaches more than 99.5 percent.
By combining the detection results in the table 1, it can be seen that the naringin in the pummelo peel is extracted by using the eutectic solvent with a specific proportion system, the naringin content in the supernatant obtained after extraction is high, and the extraction rate of the naringin is high, and referring to the detection results of the example 2 and the examples 4-5, it can be seen that the extraction rate is better compared with the extraction by using the eutectic solvent in combination with ultrasonic auxiliary extraction; referring to the detection results of the embodiment 5 and the embodiments 6 and 7, it can be seen that when the extract is made into powder, pre-freezing and freeze-drying are adopted after concentration, compared with the method of directly adding water into the extract for crystallization, the loss in the process of obtaining the powder is lower, and the yield of the finally obtained naringin dihydrochalcone is also obviously improved; referring to the test results of example 5 and examples 8-11, it can be seen that when the eutectic solvent is selected from choline chloride, acetic acid and 1, 6-hexanediol, the extraction efficiency is better, and in combination with the test results of comparative examples 1 and 2, it can be seen that when the eutectic solvent is used to extract naringin from exocarpium Citri Grandis, the extraction effect of choline chloride, acetic acid and 1, 6-hexanediol is better than the extraction effect of choline chloride and acetic acid or choline chloride and 1, 6-hexanediol, and referring to the test results of comparative examples 3-6, it can be seen that when acetic acid is replaced by other organic acids, the extraction effect is still worse, when acetic acid is replaced by other organic matters such as thiourea, and referring to the test results of example 5 and comparative example 7, it can be seen that when the eutectic solvent is used in this application, compared to the conventional extraction with organic solvents such as ethanol, the method has better extraction rate.
The present embodiment is only for explaining the present application, and it is not limited to the present application, and those skilled in the art can make modifications of the present embodiment without inventive contribution as needed after reading the present specification, but all of them are protected by patent law within the scope of the claims of the present application.
Claims (10)
1. A method for preparing a naringin dihydrochalcone sweetener by hydrogenating an exocarpium citri grandis extract is characterized by comprising the following steps:
extraction: extracting naringin from the crushed pummelo peel by using a eutectic solvent to obtain a naringin extracting solution;
ring opening and hydrogenation: performing ring opening on naringin by adopting an alkali substance to obtain naringin chalcone, and then hydrogenating the obtained naringin chalcone to obtain naringin dihydrochalcone;
wherein, the feed-liquid ratio of the crushed pummelo peel and the eutectic solvent in the extraction step is 1 (15-20), and the molar ratio of the adopted eutectic solvent is 1: (1-1.5): (0.5-1) choline chloride, acetic acid and polyhydric alcohol.
2. The method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract according to the claim 1, wherein the method comprises the following steps: the eutectic solvent is prepared by the following method:
weighing choline chloride, acetic acid and polyalcohol at a molar ratio, heating at 70-80 deg.C, stirring for 1.5-2 hr to obtain transparent and uniform solvent.
3. The method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract according to the claim 1, wherein the method comprises the following steps: the extraction of naringin in the crushed pummelo peel by the eutectic solvent is carried out under the ultrasonic condition, and the ultrasonic power is 80-100 w.
4. The method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract according to the claim 3, wherein the method comprises the following steps: in the extraction step, the extraction time is 60-80min, and the extraction temperature is 30-40 ℃.
5. The method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract according to the claim 1, wherein the method comprises the following steps: therefore, the polyhydric alcohol is selected from any one of ethylene glycol, glycerol, butanediol and 1, 6-hexanediol.
6. The method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract according to the claim 1, wherein the method comprises the following steps: the extraction step further comprises: centrifuging naringin extract obtained by extraction with eutectic solvent at the rotating speed of 2000-4000r/min, taking supernatant, concentrating to obtain extract with the relative density of 1.1-1.2 at 60 ℃, spray drying, adding water into the extract for crystallization, filtering to obtain crystals, filtering and drying the crystals to obtain naringin.
7. The method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract according to the claim 6, wherein the method comprises the following steps: and cooling the extract after spray drying, wherein the cooling operation comprises the following specific steps: the specific operation of cooling after spray drying is as follows: pre-freezing at (-25) ° C to (-10) ° C for 3-4h, and freeze-drying under the following conditions: freezing for 22-24h at (-30) - (-20) deg.C under vacuum degree of 10Pa, cooling, and crystallizing with water.
8. The method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract according to the claim 1, wherein the method comprises the following steps: the ring opening and hydrogenation operations are as follows: dissolving the prepared naringin in alkali liquor, opening the ring, adding a palladium-carbon catalyst, introducing hydrogen for hydrogenation reaction, filtering, adjusting the filtrate to be neutral, standing for 40-48h, filtering, and taking out crystals to obtain a naringin dihydrochalcone crude product;
and dissolving the crude naringin dihydrochalcone product by using ethanol, adding active carbon into the dissolved solution for decoloring, filtering, cooling and crystallizing, filtering to obtain crystals, and drying in vacuum to obtain the naringin dihydrochalcone.
9. The method for preparing the naringin dihydrochalcone sweetener by hydrogenating the pummelo peel extract according to the claim 8, wherein the pummelo peel extract comprises the following steps: the hydrogenation reaction parameters are as follows: the hydrogenation reaction temperature is 50-60 deg.C, the reaction time is 4-8h, the hydrogen pressure is 0.5-2.0Mpa, and the pH of the reaction solution is 12-13.
10. Naringin dihydrochalcone sweetener obtainable by applying the method according to any of the claims 1 to 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111139307.6A CN113735919B (en) | 2021-09-28 | 2021-09-28 | Method for preparing naringin dihydrochalcone sweetener by adding hydrogen into pummelo peel extract and prepared naringin dihydrochalcone sweetener |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111139307.6A CN113735919B (en) | 2021-09-28 | 2021-09-28 | Method for preparing naringin dihydrochalcone sweetener by adding hydrogen into pummelo peel extract and prepared naringin dihydrochalcone sweetener |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN113735919A true CN113735919A (en) | 2021-12-03 |
| CN113735919B CN113735919B (en) | 2023-03-31 |
Family
ID=78741450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111139307.6A Active CN113735919B (en) | 2021-09-28 | 2021-09-28 | Method for preparing naringin dihydrochalcone sweetener by adding hydrogen into pummelo peel extract and prepared naringin dihydrochalcone sweetener |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113735919B (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105481916A (en) * | 2014-09-15 | 2016-04-13 | 闻永举 | Preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis |
| CN106749442A (en) * | 2016-12-08 | 2017-05-31 | 河西学院 | A kind of method of benzyl carbinol glycosides in Salt treatment eutectic solvent extraction saline cistanche |
| CN107628959A (en) * | 2017-10-31 | 2018-01-26 | 河北师范大学 | Choline eutectic solvent, preparation method and the application in trollflower flavone c-glycoside is extracted |
| CN109879917A (en) * | 2019-03-26 | 2019-06-14 | 华中农业大学 | A kind of method that Exocarpium Citri Grandis extract adds hydrogen to prepare aurantiin dihydrochalcone sweetener |
-
2021
- 2021-09-28 CN CN202111139307.6A patent/CN113735919B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105481916A (en) * | 2014-09-15 | 2016-04-13 | 闻永举 | Preparation method of flavone aglycone or monoglycoside from aluminum-salt-flavonoid-glycoside complex through hydrolysis |
| CN106749442A (en) * | 2016-12-08 | 2017-05-31 | 河西学院 | A kind of method of benzyl carbinol glycosides in Salt treatment eutectic solvent extraction saline cistanche |
| CN107628959A (en) * | 2017-10-31 | 2018-01-26 | 河北师范大学 | Choline eutectic solvent, preparation method and the application in trollflower flavone c-glycoside is extracted |
| CN109879917A (en) * | 2019-03-26 | 2019-06-14 | 华中农业大学 | A kind of method that Exocarpium Citri Grandis extract adds hydrogen to prepare aurantiin dihydrochalcone sweetener |
Non-Patent Citations (2)
| Title |
|---|
| 刘丹宁 等: ""超声波辅助低共熔溶剂提取枳实中芸香柚皮苷、柚皮苷和橙皮苷"", 《中药材》 * |
| 李杰 等: ""低共熔溶剂提取枳实中黄酮类成分的工艺研究"", 《应用化工》 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN113735919B (en) | 2023-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6014640B2 (en) | Rebaudioside A derivative product and production method | |
| JP5364894B2 (en) | Carotenoid composition containing modified acacia gum | |
| EP1262543B1 (en) | Alpha-amylase activity inhibitors | |
| CN108777992A (en) | Highly dissoluble steviol glycoside | |
| CN107404911A (en) | Rebaudiodside A M biosynthesis production and recovery method | |
| US10368570B2 (en) | Food ingredients from stevia rebaudiana | |
| BR112018000550B1 (en) | Method for preparing a steviol glycoside composition | |
| CN111418852A (en) | Method for preparing plantain seed husk water-soluble fiber powder by compound enzyme method | |
| EP3736280A1 (en) | Sweetener composition and preparation method and use thereof | |
| US3751270A (en) | Sugar compositions containing aglyconic dihydrochalcones | |
| CN108220366A (en) | Hesperetin dihydrochalcone -7-O- glucoside bioanalysis synthesis technologies | |
| JP2008500037A (en) | Functional food and method for producing the same | |
| CN113735919B (en) | Method for preparing naringin dihydrochalcone sweetener by adding hydrogen into pummelo peel extract and prepared naringin dihydrochalcone sweetener | |
| JP2004018376A (en) | alpha-GLUCOSIDASE INHIBITOR | |
| CN110777173B (en) | Method for preparing momordica grosvenori amino acid by using momordica grosvenori centrifugal waste residues | |
| KR101788783B1 (en) | Berry jam including sorghum syrup and apple concentrate and manufacturing method thereof | |
| CN111187328A (en) | Method for preparing mogrol | |
| CN114031655B (en) | Crystallization method of stevioside | |
| CN115894732A (en) | Wolfberry polysaccharide extraction method based on aqueous two-phase solvent system | |
| US9994606B2 (en) | Process for the purification of Rebaudioside A and compositions thereof | |
| CN110484577B (en) | Method for extracting and preparing mannose from dragon fruit stems | |
| ES2688836T3 (en) | Enzymatic modification of sweet blackberry leaves | |
| CN109938068B (en) | Method for reducing middle-advanced glycosylation end products of cookies | |
| KR102219193B1 (en) | A composition improving quality of taste comprising allulose | |
| WO2022110519A1 (en) | Compound sweetener for improving lasting sweetness of siraitia grosvenorii extract, and preparation method therefor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |