CN105693783B - The preparation method of gossypose is extracted in a kind of dregs of rice from cotton seed - Google Patents
The preparation method of gossypose is extracted in a kind of dregs of rice from cotton seed Download PDFInfo
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- CN105693783B CN105693783B CN201610043247.0A CN201610043247A CN105693783B CN 105693783 B CN105693783 B CN 105693783B CN 201610043247 A CN201610043247 A CN 201610043247A CN 105693783 B CN105693783 B CN 105693783B
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- cotton seed
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- gossypose
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- ethanol solution
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- 229920000742 Cotton Polymers 0.000 title claims abstract description 45
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose 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[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 title claims abstract description 36
- 235000007164 Oryza sativa Nutrition 0.000 title claims abstract description 30
- 235000009566 rice Nutrition 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 240000007594 Oryza sativa Species 0.000 title abstract 2
- 238000002425 crystallisation Methods 0.000 claims abstract description 15
- 230000008025 crystallization Effects 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 87
- 241000209094 Oryza Species 0.000 claims description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 13
- QBKSWRVVCFFDOT-UHFFFAOYSA-N gossypol Chemical compound CC(C)C1=C(O)C(O)=C(C=O)C2=C(O)C(C=3C(O)=C4C(C=O)=C(O)C(O)=C(C4=CC=3C)C(C)C)=C(C)C=C21 QBKSWRVVCFFDOT-UHFFFAOYSA-N 0.000 claims description 12
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 claims description 10
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- QHOPXUFELLHKAS-UHFFFAOYSA-N Thespesin Natural products CC(C)c1c(O)c(O)c2C(O)Oc3c(c(C)cc1c23)-c1c2OC(O)c3c(O)c(O)c(C(C)C)c(cc1C)c23 QHOPXUFELLHKAS-UHFFFAOYSA-N 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 229930000755 gossypol Natural products 0.000 claims description 6
- 229950005277 gossypol Drugs 0.000 claims description 6
- 238000005349 anion exchange Methods 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 238000010828 elution Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 22
- 239000011347 resin Substances 0.000 abstract description 4
- 229920005989 resin Polymers 0.000 abstract description 4
- 239000012535 impurity Substances 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 2
- 235000019441 ethanol Nutrition 0.000 description 30
- 239000003480 eluent Substances 0.000 description 6
- 235000012343 cottonseed oil Nutrition 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 244000298715 Actinidia chinensis Species 0.000 description 1
- 235000009434 Actinidia chinensis Nutrition 0.000 description 1
- 235000009436 Actinidia deliciosa Nutrition 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000186000 Bifidobacterium Species 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/06—Oligosaccharides, i.e. having three to five saccharide radicals attached to each other by glycosidic linkages
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention relates to the preparation methods that high-purity gossypose is extracted in a kind of dregs of rice from cotton seed.The method of the present invention step is simple, without repeatedly crystallization, avoids that crystallisation step is cumbersome, condition is stringent, lasts long disadvantage, and before the step of by that will crystallize, advances to resin separation, the content for greatly reducing impurity in product improves the purity of product, and yield is higher.
Description
Technical field
The present invention relates to the preparation methods of gossypose, more particularly, to the system for extracting gossypose in a kind of dregs of rice from cotton seed
Preparation Method.
Background technology
Gossypose（raffinose）It is a kind of trisaccharide most well-known in nature, is combined by galactolipin, fructose and glucose
It forms, also referred to as melitriose, other than being a kind of excellent Bifidobacterium proliferation factor, also has and inhibit the production of enteral corruption
Object improves bowel movement function, generates nutriment, enhancing immunity of organisms, resists the different physiological roles such as tumour.
Gossypose is widespread in nature, such as in many vegetables（Such as cabbage, beet）, fruit（As grape,
Kiwi berry etc.）, paddy（Wheat, oat etc.）All contain gossypose in varying numbers in the seed benevolence of some oil crops.China is every
For producing cotton seed oil, the remaining cotton seed dregs of rice are caused larger a large amount of cotton seeds of Nian Douyou by as feed or directly discarding
Waste.Thus, in recent years, the comprehensive utilizating research about the cotton seed dregs of rice gradually increases, and it is to cotton that gossypose is extracted from the cotton seed dregs of rice
The good method that the sub- dregs of rice are comprehensively utilized.
For example, CN101390583 discloses a kind of method for extracting gossypose in the dregs of rice from cotton seed, using the ethyl alcohol of 70-80%
Solution impregnates the cotton seed dregs of rice, and activated carbon decolorizing is added after extracting solution concentration, and seed raffinose, cooling knot is added in the concentrate after decoloration
Crystalline substance, the ethanol solution room temperature for adding 45-55% are stood still for crystals, and are recrystallized under the ethanol solution low temperature of 55-65%, then use 75-
85% ethanol solution room temperature crystallization, finally obtains gossypose.But overall procedure needs repeatedly crystallization, and program is more complicated, and wraps
It is impure.
Further for example, Dai Weidong et al. have studied extracted from the cotton seed dregs of rice ethanol solution concentration of gossypose, extraction temperature and
Influence of three factor of solid-liquid ratio to leaching rate show that best operating condition is：Extracting temperature is 55 DEG C, and extraction solid-liquid ratio is 1:
12, the leaching rate of concentration of alcohol 80%, gossypose is 90% or more.
But not only contain gossypose in the cotton seed dregs of rice, also include cottonseed protein and the virose gossypol constituents of tool, because
This, the characteristics of, hydrous ethanol isopolarity solvent soluble easily in water according only to gossypose is to use leaching of such solvent as gossypose
When extraction solvent, since cottonseed protein etc. can also be dissolved in the water so that the impurity in gossypose extracting solution is excessive, to gossypose
Purifying and crystallization cause difficulty.
For drawbacks described above and deficiency existing for the method for preparing gossypose in the prior art, the purpose of the present invention provides
One kind is simple for process, production efficiency is high, gossypose preparation method easy to operate.
Invention content
The present invention provides the preparation methods that gossypose is extracted in a kind of dregs of rice from cotton seed, include the following steps：
（1）With ethanol solution under the conditions of 30-40 DEG C soak extraction cotton seed dregs of rice 2-4 times, mixed extract；
（2）It filters and concentrated extracting solution, addition seed raffinose stand 12-24 hours and cotton seed sugar crystal are precipitated after stirring；
（3）The ethanol solution that envelope-bulk to weight ratio is 3-5 times is added in above-mentioned cotton seed sugar crystal, upper oh type anion is handed over
Resin is changed, with -75% ethyl alcohol of acetic acid（1:10）Solution elutes；
（4）Concentrate eluant, vacuum drying, obtains cotton seed sugar product.
Preferably, the ethanol solution in method is 70-80% ethanol solutions.
Preferably, room temperature need to be cooled to 10 DEG C and crystallized by the step (2).
Gossypose product purity made from the method for the present invention is 99.5% or more, and is substantially free of gossypol.
Compared with prior art, technical scheme of the present invention has the following advantages：The method of the present invention step is simple, without more
Secondary crystallization, avoids that crystallisation step is cumbersome, condition is stringent, lasts long disadvantage.The method of the present invention will advance to the step of crystallization
Before resin separation, good effect is obtained, the content of impurity in product is greatly reduced, improves the purity of product, and is obtained
Obtained higher yield.
Present inventor has carried out a large number of experiments, and experimental result provided below is used to show the preparation side of the present invention
The significant advantageous effect of method.Wherein, the method for gossypose and gossypol is method well known in the art in product, be may be used
HPLC methods etc..
Experiment material：The cotton seed dregs of rice, 75% ethyl alcohol, acetic acid, cotton seed sugar crystal, methanol, ether
The method of the present invention：According to the method for embodiment 1, raw material takes the 100g cotton seed dregs of rice.
Contrast method 1：The 100g cotton seed dregs of rice are taken, the soak extraction cotton seed dregs of rice 3 times under the conditions of 30-40 DEG C with 75% ethanol solution,
Mixed extract；Filter simultaneously concentrated extracting solution, upper oh type anion exchange resin, with -75% ethyl alcohol of acetic acid（1:10）Solution is washed
It is de-, collect eluent；It is transferred to crystallizing tank, seed raffinose is added, after stirring, 10 DEG C is cooled to, stands 12 hours and tied
It is brilliant；After crystallization is taken out in filtering, vacuum drying obtains cotton seed sugar product.
Contrast method 2：The 100g cotton seed dregs of rice are taken, the soak extraction cotton seed dregs of rice 3 times under the conditions of 30-40 DEG C with 75% ethanol solution,
Mixed extract；It filters and concentrated extracting solution, is transferred to crystallizing tank, seed raffinose is added, after stirring, be cooled to 10 DEG C, it is quiet
It sets 12 hours and is crystallized；After crystallization is taken out in filtering, 5 times of amount 80% ethanol solution dissolvings, upper oh type anion exchange tree is added
Fat is eluted with 75% ethanol solution, collects eluent, is dried in vacuo, is obtained cotton seed sugar product.
Contrast method 3：The 100g cotton seed dregs of rice are taken, the soak extraction cotton seed dregs of rice 3 times under the conditions of 30-40 DEG C with 75% ethanol solution,
Mixed extract；It filters and concentrated extracting solution, is transferred to crystallizing tank, seed raffinose is added, after stirring, be cooled to 10 DEG C, it is quiet
It sets 12 hours and is crystallized；After crystallization is taken out in filtering, 5 times of amount 80% ethanol solution dissolvings, upper oh type anion exchange tree is added
Fat, with -75% ethyl alcohol of 0.5% aqueous sodium carbonate（1:10）Solution elutes, and collects eluent, is dried in vacuo, obtains cotton seed sugar product.
Contrast method 4：The 100g cotton seed dregs of rice are taken, the soak extraction cotton seed dregs of rice 3 times under the conditions of 30-40 DEG C with 75% ethanol solution,
Mixed extract；It filters and concentrated extracting solution, is transferred to crystallizing tank, seed raffinose is added, after stirring, be cooled to 10 DEG C, it is quiet
It sets 12 hours and is crystallized；After crystallization is taken out in filtering, 5 times of amount 80% ethanol solution dissolvings, upper C18 resins, with acetic acid -75% is added
Ethanol solution（1:10）Elution, collects eluent, is dried in vacuo, obtains cotton seed sugar product.
Experimental result see the table below.
It can be seen that the method for the present invention obtains advantageous effect extremely outstanding, product purity is high, and method is simply easy
Row is conducive to industrialized production.
Specific implementation mode
The following specific embodiments are described below illustrates the present invention in more detail.
Embodiment 1
The 50kg cotton seed dregs of rice are taken, the soak extraction cotton seed dregs of rice 3 times under the conditions of 30-40 DEG C with 75% ethanol solution, mixing extraction
Liquid；Simultaneously concentrated extracting solution is filtered, crystallizing tank is transferred to, seed raffinose is added, after stirring, 10 DEG C is cooled to, stands 12 hours
It is crystallized；After crystallization is taken out in filtering, 5 times of amount 80% ethanol solution dissolvings are added, upper oh type anion exchange resin uses vinegar
Sour -75% ethyl alcohol（1:10）Solution elutes, and collects eluent, is dried in vacuo, obtains cotton seed sugar product.After testing, cotton seed sugar product is pure
For degree up to 99.8%, gossypol content is less than 10ppm.
Embodiment 2
The 50kg cotton seed dregs of rice are taken, the soak extraction cotton seed dregs of rice 2 times under the conditions of 30-40 DEG C with 80% ethanol solution, mixing extraction
Liquid；Simultaneously concentrated extracting solution is filtered, crystallizing tank is transferred to, seed raffinose is added, after stirring, 10 DEG C is cooled to, stands 18 hours
It is crystallized；After crystallization is taken out in filtering, 4 times of amount 80% ethanol solution dissolvings are added, upper oh type anion exchange resin uses vinegar
Sour -75% ethyl alcohol（1:10）Solution elutes, and collects eluent, is dried in vacuo, obtains cotton seed sugar product.After testing, cotton seed sugar product is pure
For degree up to 99.7%, gossypol content is less than 10ppm.
Claims (1)
1. extracting the preparation method of gossypose in a kind of dregs of rice from cotton seed, it is characterised in that comprise the steps of：
(1) 70-80% ethanol solutions soak extraction cotton seed dregs of rice 2-4 times, mixed extract under the conditions of 30-40 DEG C are used；
(2) filtering and concentrated extracting solution, be added seed raffinose, stand 12-24 hours after stirring, by room temperature be cooled to 10 DEG C into
Row crystallization, is precipitated cotton seed sugar crystal；
(3) ethanol solution that envelope-bulk to weight ratio is 3-5 times, upper oh type anion exchange tree are added in above-mentioned cotton seed sugar crystal
Fat, with 1:10-75% ethanol solution of acetic acid elution；
(4) concentrate eluant, vacuum drying obtain cotton seed sugar product, and gossypose product purity is 99.5% or more, and is substantially free of
Gossypol.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610043247.0A CN105693783B (en) | 2016-01-23 | 2016-01-23 | The preparation method of gossypose is extracted in a kind of dregs of rice from cotton seed |
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| CN201610043247.0A CN105693783B (en) | 2016-01-23 | 2016-01-23 | The preparation method of gossypose is extracted in a kind of dregs of rice from cotton seed |
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| CN105693783A CN105693783A (en) | 2016-06-22 |
| CN105693783B true CN105693783B (en) | 2018-10-23 |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1699388A (en) * | 2005-05-23 | 2005-11-23 | 青岛国风药业股份有限公司 | Raffinoses oligosaccharide with stachyose as main materials and method for preparing same |
| CN101263153A (en) * | 2005-08-30 | 2008-09-10 | 法马德医疗保险私人有限公司 | Process for production of chlorinated sucrose based on hydrophobic affinity chromatography |
| CN101390583A (en) * | 2007-09-17 | 2009-03-25 | 白心亮 | Method for extracting gossypose from cotton seed meal |
| CN102898486A (en) * | 2012-09-21 | 2013-01-30 | 晨光生物科技集团股份有限公司 | Comprehensive method for preparation of raffinose and gossypol from cottonseed meal |
| CN103724379A (en) * | 2013-12-31 | 2014-04-16 | 晨光生物科技集团股份有限公司 | Method for extracting raffinose from cottonseed meal dephenolization solution |
-
2016
- 2016-01-23 CN CN201610043247.0A patent/CN105693783B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1699388A (en) * | 2005-05-23 | 2005-11-23 | 青岛国风药业股份有限公司 | Raffinoses oligosaccharide with stachyose as main materials and method for preparing same |
| CN101263153A (en) * | 2005-08-30 | 2008-09-10 | 法马德医疗保险私人有限公司 | Process for production of chlorinated sucrose based on hydrophobic affinity chromatography |
| CN101390583A (en) * | 2007-09-17 | 2009-03-25 | 白心亮 | Method for extracting gossypose from cotton seed meal |
| CN102898486A (en) * | 2012-09-21 | 2013-01-30 | 晨光生物科技集团股份有限公司 | Comprehensive method for preparation of raffinose and gossypol from cottonseed meal |
| CN103724379A (en) * | 2013-12-31 | 2014-04-16 | 晨光生物科技集团股份有限公司 | Method for extracting raffinose from cottonseed meal dephenolization solution |
Non-Patent Citations (3)
| Title |
|---|
| Comparison of two HPLC systems and an enzymatic method for quantification of soybean sugars;Enzo Giannoccaro，等;《Food Chemistry》;20080101;第106卷(第1期);第324–330页 * |
| 寡糖色谱分离研究进展;傅青，等;《生命科学》;20110731;第23卷(第7期);第703-713页 * |
| 糖的高效阴离子交换色谱脉冲安培检测法分析;牟世芬，等;《色谱》;20090930;第27卷(第5期);第667-674页 * |
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Address after: 028400 no.0427, Dongjiao Industrial Park, Kailu Town, Kailu County, Tongliao City, Inner Mongolia Autonomous Region Patentee after: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Address before: 011517 Hohhot city Helingeer County Inner Mongolia Shengle economic Park Patentee before: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. |
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Denomination of invention: A method for extracting raffinose from cottonseed meal Effective date of registration: 20210222 Granted publication date: 20181023 Pledgee: Agricultural Bank of China Limited Helingeer County sub branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY Co.,Ltd. Registration number: Y2021150000016 |
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Date of cancellation: 20220321 Granted publication date: 20181023 Pledgee: Agricultural Bank of China Limited Helingeer County sub branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2021150000016 |
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Denomination of invention: A preparation method for extracting raffinose from cottonseed meal Effective date of registration: 20220330 Granted publication date: 20181023 Pledgee: Agricultural Bank of China Limited Helingeer County sub branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2022150000027 |
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Date of cancellation: 20230301 Granted publication date: 20181023 Pledgee: Agricultural Bank of China Limited Helingeer County sub branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2022150000027 |
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Denomination of invention: A preparation method for extracting raffinose from cottonseed meal Effective date of registration: 20230307 Granted publication date: 20181023 Pledgee: China Minsheng Banking Corp Hohhot branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2023150000031 |
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Date of cancellation: 20231031 Granted publication date: 20181023 Pledgee: China Minsheng Banking Corp Hohhot branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2023150000031 |
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Denomination of invention: A preparation method for extracting raffinose from cottonseed meal Effective date of registration: 20231101 Granted publication date: 20181023 Pledgee: China Minsheng Banking Corp Hohhot branch Pledgor: INNER MONGOLIA CHANGHUI BIOTECHNOLOGY CO.,LTD. Registration number: Y2023150000154 |