CN116715616A - Environment-friendly and efficient preparation method of sulforaphane - Google Patents
Environment-friendly and efficient preparation method of sulforaphane Download PDFInfo
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- CN116715616A CN116715616A CN202310106779.4A CN202310106779A CN116715616A CN 116715616 A CN116715616 A CN 116715616A CN 202310106779 A CN202310106779 A CN 202310106779A CN 116715616 A CN116715616 A CN 116715616A
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- sulforaphane
- friendly
- environment
- efficient
- extraction
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- SUVMJBTUFCVSAD-UHFFFAOYSA-N sulforaphane Chemical compound CS(=O)CCCCN=C=S SUVMJBTUFCVSAD-UHFFFAOYSA-N 0.000 title claims abstract description 90
- SUVMJBTUFCVSAD-JTQLQIEISA-N 4-Methylsulfinylbutyl isothiocyanate Natural products C[S@](=O)CCCCN=C=S SUVMJBTUFCVSAD-JTQLQIEISA-N 0.000 title claims abstract description 45
- 229960005559 sulforaphane Drugs 0.000 title claims abstract description 45
- 235000015487 sulforaphane Nutrition 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 21
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 claims abstract description 20
- 235000017647 Brassica oleracea var italica Nutrition 0.000 claims abstract description 20
- 240000003259 Brassica oleracea var. botrytis Species 0.000 claims abstract description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 238000000605 extraction Methods 0.000 claims description 27
- 239000002808 molecular sieve Substances 0.000 claims description 19
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 10
- 239000000706 filtrate Substances 0.000 claims description 9
- 238000005303 weighing Methods 0.000 claims description 9
- 239000000284 extract Substances 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 239000000401 methanolic extract Substances 0.000 claims description 6
- 239000000843 powder Substances 0.000 claims description 6
- 238000011068 loading method Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- 239000002002 slurry Substances 0.000 claims description 4
- 238000000227 grinding Methods 0.000 claims description 3
- 238000005360 mashing Methods 0.000 claims description 3
- 238000010298 pulverizing process Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 11
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 6
- 238000003912 environmental pollution Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 6
- 238000006297 dehydration reaction Methods 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 230000007613 environmental effect Effects 0.000 description 4
- 239000011148 porous material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- BYFGZMCJNACEKR-UHFFFAOYSA-N aluminium(i) oxide Chemical compound [Al]O[Al] BYFGZMCJNACEKR-UHFFFAOYSA-N 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000003809 water extraction Methods 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000337 buffer salt Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000000413 hydrolysate Substances 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/22—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The application discloses an environment-friendly and efficient preparation method of sulforaphane, which is a method for efficiently extracting sulforaphane from broccoli seeds, overcomes potential biosafety risks caused by using a large amount of organic reagents in the traditional production process and environmental pollution risks caused by the potential biosafety risks, and can realize industrialized production.
Description
Technical Field
The application relates to the field of chemical preparation, in particular to an environment-friendly and efficient preparation method of sulforaphane.
Background
Sulforaphane is an isothiocyanate and is one of compounds with remarkable anticancer activity in the nature world currently accepted. In 1992, the Talalay professor team of university of Hopkins in the United states discovered sulforaphane from broccoli, studied the cancer prevention and anti-cancer effects of sulforaphane, found that sulforaphane has an inhibitory effect on liver cancer, colon cancer, breast cancer, prostate cancer and the like, and induced Phase II enzyme to activate the generation of self-anticancer substances; in addition, the sulforaphane also has the effects of regulating immunity and resisting oxidation. But the chemical properties of the sulforaphane are unstable, the temperature, the pH value, the water and the air can influence the sulforaphane, the longer the production and processing time is, the more steps are, the lower the yield is, the demand of the current market for the high-purity sulforaphane is not large, and the efficient, rapid and gentle extraction of the sulforaphane has practical significance for improving the product yield and reducing the cost.
The molecular sieve is an artificially synthesized hydrated aluminosilicate with molecular screening function, and structurally has a plurality of pore channels with uniform pore diameters and orderly arranged holes, and the molecular sieve with different pore diameters separates molecules with different sizes and shapes. Molecular sieves with different pore diameters can be obtained according to different molecular ratios of SiO2 and Al2O 3. Molecular sieves with low silica to alumina ratios (e.g., type a, type X, etc.) have polar hydrophilicity and are commonly used for air drying and low water content ethanol and methanol production.
By consulting the prior domestic sulforaphane preparation patent technology, we find that the prior patent technology has a complex process route and needs a large amount of organic reagents such as dichloromethane, acetone and the like, so that the production cost is difficult to control, the biological safety risk and the environmental safety risk are high, and the actual industrialized production is difficult. For example, in the CN200710156140 patent, the hydrolysate after enzymolysis needs to be freeze-dried, an acetone reagent is used for extraction, and a large amount of organic waste liquid is generated when normal phase silica gel is used for purification, so that the cost cannot be controlled and the environmental risk is high; the CN201210414994 patent firstly uses absolute ethyl alcohol for extraction, and then uses macroporous resin and alumina column for purification and decolorization after concentration, the technological process is complex, the stability of the sulforaphane in ethanol water is poorer than that in methanol, a large amount of sulforaphane is degraded after long-time heating, and the final yield is not too high; in the CN201610718698 patent, the broccoli seeds are defatted first, then the enzymolysis process uses a buffer salt system, the enzymolysis is completed, 95% ethanol is added for extraction, water is added for dilution, then dichloromethane is used for extraction, and finally normal phase silica gel is used for purification, so that the whole process is complex, the cost control and the industrialized production are not facilitated, and the environment pollution is easily caused by the large-scale use of dichloromethane.
The current market demand for high-purity sulforaphane is not very large, most of the market demand is concentrated on the fact that the content of the sulforaphane is below 20%, and how to extract the sulforaphane by using a simple, quick, efficient and mild process is needed to solve the problem that industrialization and control cost of the sulforaphane are better accelerated.
Disclosure of Invention
The application aims to provide the preparation method of the sulforaphane, which has the advantages of tonifying qi, increasing gain, being rich in nutrition, good in taste, environment-friendly and efficient.
The above object is achieved by the following scheme:
the environment-friendly and efficient preparation method of the sulforaphane is characterized by comprising the following steps of:
(1) Pulverizing broccoli seeds, and extracting with water;
(2) After the extraction is finished, obtaining broccoli seed powder slurry, and then adding methanol into an extraction tank for extraction;
(3) Filtering after extraction is finished, and collecting methanol extract;
(4) Separating the methanol extract into a molecular sieve column, and collecting effluent;
(5) Concentrating the effluent liquid at low temperature under vacuum to obtain a sulforaphane extract;
the broccoli seed powder in the step (1): the ratio of water is 1:2-1:5.
The extraction temperature in the step (1) is 35-50 ℃;
the extraction time in the step (1) is 2-10h;
the proportion of the methanol added in the step (2) is 2-5 times of the volume of the broccoli seed powder slurry;
the extraction time of the step (2) is 0.5-2h;
the molecular sieve used in the step (4) is a 3A or 4A molecular sieve, and the dosage of the molecular sieve is 5-20 times of the weight of the methanol extract;
the concentration temperature in the step (5) is 45-65 ℃.
The environment-friendly and efficient preparation method of the sulforaphane is characterized by comprising the following steps of:
(1) Weighing broccoli seeds, mashing with a grinding bowl, adding water, mixing well, extracting at 35-50deg.C for 2-10h;
(2) Adding methanol into the extract, stirring thoroughly, suction filtering, and collecting filtrate;
(3) Weighing 3A or 4A molecular sieve, loading into an open chromatographic column, passing the filtrate through the column, collecting effluent, and repeatedly passing the effluent through the column for 3-4 times;
(4) Concentrating the effluent liquid under vacuum at 45-65 deg.C until no alcohol is present to obtain brown paste.
The beneficial effects of the application are as follows:
(1) The application creatively improves the dehydration process after water extraction of broccoli seeds and the extraction process of sulforaphane, abandons the freeze-drying, vacuum drying and salt drying dehydration process in the prior art, adopts a molecular sieve dehydration process, solves the problems of low efficiency, high energy consumption and high cost of freeze-drying and vacuum drying, solves the problem of a large amount of solid wastes generated in the salt dehydration process, realizes industrial continuous production, can repeatedly regenerate and use the molecular sieve, and remarkably reduces the production cost, the production efficiency and the environmental protection cost. The methanol is selected on the extraction solvent, organic reagents with relatively large toxicity such as acetone, methylene dichloride and the like are abandoned, the production cost is reduced, the biological risk and the environmental risk are also reduced, the quality of the final product is stable, and the current market demand is met.
(2) Compared with the prior art, the method has the advantages of simple and feasible process, low cost, easy standardization and industrialization, and the content of the finally obtained sulforaphane extract is stabilized at 30-40%. Meanwhile, the molecular sieve is creatively introduced, so that the problem of dehydration after water extraction of broccoli seeds is solved, the treatment environment is mild, the extraction reagent only uses methanol, and the methanol is a low-toxicity organic reagent and is widely applied to the plant extraction industry;
(3) The core of the application is innovation of the dehydration process after the enzymolysis of the broccoli seeds, solves the factor-water which has the greatest influence on the sulforaphane content in the subsequent production process, and simultaneously utilizes methanol as a solvent, so that a large amount of broccoli seed oil can be prevented from being introduced into the final product, and the high content and higher stability of the sulforaphane in the final product are ensured.
Detailed Description
Example 1
An environment-friendly and efficient preparation method of sulforaphane comprises the following steps:
(1) Weighing 100g of broccoli seeds, mashing with a grinding bowl, adding 300g of water, uniformly mixing, and extracting for 2 hours at 35 ℃;
(2) Adding 1500ml of methanol into the extract, stirring thoroughly, suction filtering, and collecting filtrate;
(3) Weighing 4kg of 4A molecular sieve, loading into an 80 x 600mm open chromatographic column, passing the filtrate through the column, collecting the effluent, controlling the flow rate at 3BV/h, and repeatedly passing the collected liquid through the column for 3 times;
(4) Concentrating the collected liquid in vacuum at 55 ℃ until no alcohol exists;
(5) Obtaining brown paste. The obtained product is detected by HPLC to have the sulforaphane content of 42.2 percent;
example 2
An environment-friendly and efficient preparation method of sulforaphane comprises the following steps:
(1) Weighing 1kg of broccoli seeds, pulverizing, adding 2kg of water, mixing well, stirring in water bath at 40deg.C for extraction
3h；
(2) After the extraction is finished, adding 25kg of methanol into the extract, fully and uniformly stirring, carrying out suction filtration, and collecting filtrate;
(3) Weighing 25kg of 4A molecular sieve, loading into 200 x 1000 open chromatographic column, passing the filtrate through the column, collecting effluent, controlling the flow rate at 3-5BV/h, and repeating the passing of the effluent through the column for 3 times;
(4) Collecting effluent liquid, vacuum concentrating at 60deg.C, removing ethanol to obtain brown extract-like substance,
obtaining the product. The obtained product has the sulforaphane content of 41.5 percent by HPLC detection.
Example 3
An environment-friendly and efficient preparation method of sulforaphane comprises the following steps:
(1) Weighing 5kg of broccoli seeds, and crushing by a high-speed crusher;
(2) Adding 7.5kg of water, mixing uniformly, heating and stirring to 37 ℃ for extraction for 4 hours, then heating to 45 ℃ and preserving heat for 1 hour;
(3) Adding 20kg of methanol after the extraction is finished, and stirring and extracting for 2 hours;
(4) Filtering with a filter bag, collecting the extractive solution, filtering with diatomite, and collecting the filtrate;
(5) Loading 100kg of 3A molecular sieve into a stainless steel chromatographic column system, starting an automatic liquid feeding system, controlling the flow rate to be 20L/hour, circularly feeding samples for 5 hours, and collecting effluent liquid;
(6) Concentrating the effluent by rotary steaming at 65deg.C until no alcohol is present, and obtaining 140g brown paste.
The content of the sulforaphane is 40.8 percent by HPLC detection;
the foregoing embodiments, while not particularly shown, are presented to facilitate an understanding of the principles and applications of the present application, and are not intended to provide a complete understanding of the principles and applications of the present application, as will be readily apparent to those of ordinary skill in the art, and are modified in light of the foregoing embodiments and without undue experimentation. Accordingly, modifications and improvements within the scope of the application may be made by those skilled in the art in view of the teachings of this application.
Claims (9)
1. The environment-friendly and efficient preparation method of the sulforaphane is characterized by comprising the following steps of:
(1) Pulverizing broccoli seeds, and extracting with water;
(2) After the extraction is finished, obtaining broccoli seed powder slurry, and then adding methanol into an extraction tank for extraction;
(3) Filtering after extraction is finished, and collecting methanol extract;
(4) Separating the methanol extract into a molecular sieve column, and collecting effluent;
(5) Concentrating the effluent liquid at low temperature under vacuum to obtain extract, and obtaining sulforaphane extract.
2. The method for preparing the environment-friendly and efficient sulforaphane in the application as claimed in claim 1, wherein the steps (1) are characterized in that the broccoli seed powder is prepared by: the ratio of water is 1:2-1:5.
3. The method for preparing the environment-friendly and efficient sulforaphane according to claim 1, wherein the extraction temperature in the step (1) is 35-50 ℃.
4. The method for preparing the sulforaphane in an environment-friendly and efficient way according to claim 1, wherein the extraction time in the step (1) is 2-10h.
5. The method for preparing the environment-friendly and efficient sulforaphane according to claim 1, wherein the proportion of methanol added in the step (2) is 2-5 times of the volume of broccoli seed powder slurry.
6. The method for preparing the sulforaphane in an environment-friendly and efficient way according to claim 1, wherein the extraction time of the step (2) is 0.5-2h.
7. The method for preparing the environment-friendly and efficient sulforaphane according to claim 1, wherein the molecular sieve used in the step (4) is 3A or 4A molecular sieve, and the dosage of the molecular sieve is 5-20 times of the weight of the methanol extract.
8. The method for preparing the environment-friendly and efficient sulforaphane according to claim 1, wherein the concentration temperature of the step (5) is 45-65 ℃.
9. The method for preparing the environment-friendly and efficient sulforaphane according to claim 1, which is characterized by comprising the following steps:
(1) Weighing broccoli seeds, mashing with a grinding bowl, adding water, mixing well, extracting at 35-50deg.C for 2-10h;
(2) Adding methanol into the extract, stirring thoroughly, suction filtering, and collecting filtrate;
(3) Weighing 3A or 4A molecular sieve, loading into an open chromatographic column, passing the filtrate through the column, collecting effluent, and repeatedly passing the effluent through the column for 3-4 times;
(4) Concentrating the effluent liquid under vacuum at 45-65 deg.C until no alcohol is present to obtain brown paste.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310106779.4A CN116715616A (en) | 2023-02-13 | 2023-02-13 | Environment-friendly and efficient preparation method of sulforaphane |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202310106779.4A CN116715616A (en) | 2023-02-13 | 2023-02-13 | Environment-friendly and efficient preparation method of sulforaphane |
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| Publication Number | Publication Date |
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| CN116715616A true CN116715616A (en) | 2023-09-08 |
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|---|---|---|---|
| CN202310106779.4A Pending CN116715616A (en) | 2023-02-13 | 2023-02-13 | Environment-friendly and efficient preparation method of sulforaphane |
Country Status (1)
| Country | Link |
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| CN (1) | CN116715616A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898341A (en) * | 2012-10-26 | 2013-01-30 | 贵州大学 | Extracting and purifying method of high-purity sulforaphane |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102898341A (en) * | 2012-10-26 | 2013-01-30 | 贵州大学 | Extracting and purifying method of high-purity sulforaphane |
Non-Patent Citations (1)
| Title |
|---|
| 孔凡华等: "高效液相色谱法测定十字花科蔬菜中萝卜硫素的含量", 食品与发酵工业, vol. 47, no. 8, pages 218 - 223 * |
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Application publication date: 20230908 |