CN110423291B - 一种速溶透明质酸钠制备方法 - Google Patents
一种速溶透明质酸钠制备方法 Download PDFInfo
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- CN110423291B CN110423291B CN201910841457.8A CN201910841457A CN110423291B CN 110423291 B CN110423291 B CN 110423291B CN 201910841457 A CN201910841457 A CN 201910841457A CN 110423291 B CN110423291 B CN 110423291B
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- sodium hyaluronate
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- chitosan
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- 229920002385 Sodium hyaluronate Polymers 0.000 title claims abstract description 148
- 229940010747 sodium hyaluronate Drugs 0.000 title claims abstract description 148
- YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 title claims abstract description 148
- 238000002360 preparation method Methods 0.000 title claims abstract description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 81
- 229920001661 Chitosan Polymers 0.000 claims abstract description 29
- 238000004108 freeze drying Methods 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 32
- 239000000047 product Substances 0.000 claims description 29
- 239000011259 mixed solution Substances 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 18
- 239000003960 organic solvent Substances 0.000 claims description 17
- 238000000855 fermentation Methods 0.000 claims description 16
- 230000004151 fermentation Effects 0.000 claims description 16
- 238000003381 deacetylation reaction Methods 0.000 claims description 13
- 239000007789 gas Substances 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 13
- 238000007710 freezing Methods 0.000 claims description 12
- 230000008014 freezing Effects 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims description 9
- 239000000706 filtrate Substances 0.000 claims description 8
- 239000008213 purified water Substances 0.000 claims description 8
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- 241000120569 Streptococcus equi subsp. zooepidemicus Species 0.000 claims description 4
- 238000004042 decolorization Methods 0.000 claims description 4
- 230000000593 degrading effect Effects 0.000 claims description 4
- 244000005700 microbiome Species 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 230000001954 sterilising effect Effects 0.000 claims description 4
- 238000004659 sterilization and disinfection Methods 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 230000005496 eutectics Effects 0.000 claims 2
- 230000000694 effects Effects 0.000 abstract description 5
- 230000002195 synergetic effect Effects 0.000 abstract description 2
- 230000000052 comparative effect Effects 0.000 description 29
- 235000019441 ethanol Nutrition 0.000 description 25
- 239000000843 powder Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 8
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000012752 auxiliary agent Substances 0.000 description 6
- 229920002674 hyaluronan Polymers 0.000 description 6
- 229960003160 hyaluronic acid Drugs 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000009777 vacuum freeze-drying Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 3
- WCDDVEOXEIYWFB-VXORFPGASA-N (2s,3s,4r,5r,6r)-3-[(2s,3r,5s,6r)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C(O)=O)O[C@@H](O)[C@H](O)[C@H]1O WCDDVEOXEIYWFB-VXORFPGASA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000010835 comparative analysis Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000635 electron micrograph Methods 0.000 description 2
- 238000012869 ethanol precipitation Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 229940014041 hyaluronate Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000003020 moisturizing effect Effects 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002335 preservative effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 1
- 229920002683 Glycosaminoglycan Polymers 0.000 description 1
- 108010040201 Polymyxins Proteins 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000021164 cell adhesion Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0063—Glycosaminoglycans or mucopolysaccharides, e.g. keratan sulfate; Derivatives thereof, e.g. fucoidan
- C08B37/0072—Hyaluronic acid, i.e. HA or hyaluronan; Derivatives thereof, e.g. crosslinked hyaluronic acid (hylan) or hyaluronates
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
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CN112120205A (zh) * | 2020-09-25 | 2020-12-25 | 山东华熙海御生物医药有限公司 | 酱油及其粉末、它们的制备方法以及用途 |
CN113512134B (zh) * | 2021-07-30 | 2022-05-20 | 梅晔生物医药股份有限公司 | 一种全分子量分布的透明质酸钠及其制备方法和应用 |
CN115737474B (zh) * | 2022-08-30 | 2023-11-10 | 江苏长泰药业股份有限公司 | 一种葡聚糖乳液的制备方法及包含葡聚糖乳液的组合物及其用途 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000061675A1 (en) * | 1999-04-08 | 2000-10-19 | Fidia Advanced Biopolymers S.R.L. | Three-dimensional structures containing hyaluronic acid derivatives obtained by the supercritical antisolvent technique |
CN1961037A (zh) * | 2004-05-27 | 2007-05-09 | 诺维信生物聚合物公司 | 干燥和团聚的透明质酸产品 |
CN103173507A (zh) * | 2011-12-23 | 2013-06-26 | 宁波林叶生物科技有限公司 | 一种利用细菌发酵生产透明质酸钠的生产工艺 |
WO2015018461A1 (fr) * | 2013-08-09 | 2015-02-12 | Genbiotech | Compositions therapeutiques comprenant d'acide hyaluronique |
KR20180119936A (ko) * | 2017-04-26 | 2018-11-05 | 주식회사 엘지생활건강 | 활성화 공정을 포함하는 아세틸화 히알루론산의 제조방법 |
CN108948377A (zh) * | 2017-05-18 | 2018-12-07 | 武汉大学 | 一种壳聚糖的快速溶解方法及其应用 |
CN109851822A (zh) * | 2018-12-07 | 2019-06-07 | 山东众山生物科技有限公司 | 一种速溶透明质酸钠的制备方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050272695A1 (en) * | 2004-05-27 | 2005-12-08 | Novozymes Biopolymer A/S | Fast dissolving dried hyaluronic acid product |
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- 2019-09-06 CN CN201910841457.8A patent/CN110423291B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000061675A1 (en) * | 1999-04-08 | 2000-10-19 | Fidia Advanced Biopolymers S.R.L. | Three-dimensional structures containing hyaluronic acid derivatives obtained by the supercritical antisolvent technique |
CN1961037A (zh) * | 2004-05-27 | 2007-05-09 | 诺维信生物聚合物公司 | 干燥和团聚的透明质酸产品 |
CN103173507A (zh) * | 2011-12-23 | 2013-06-26 | 宁波林叶生物科技有限公司 | 一种利用细菌发酵生产透明质酸钠的生产工艺 |
WO2015018461A1 (fr) * | 2013-08-09 | 2015-02-12 | Genbiotech | Compositions therapeutiques comprenant d'acide hyaluronique |
KR20180119936A (ko) * | 2017-04-26 | 2018-11-05 | 주식회사 엘지생활건강 | 활성화 공정을 포함하는 아세틸화 히알루론산의 제조방법 |
CN108948377A (zh) * | 2017-05-18 | 2018-12-07 | 武汉大学 | 一种壳聚糖的快速溶解方法及其应用 |
CN109851822A (zh) * | 2018-12-07 | 2019-06-07 | 山东众山生物科技有限公司 | 一种速溶透明质酸钠的制备方法 |
Non-Patent Citations (1)
Title |
---|
Flow field-flow fractionation and multiangle light scattering for ultrahigh molecular weight sodium hyaluronate characterization;Myeong Hee Moon;《J.Sep.Sci》;20101231;第3519-3529页 * |
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Address after: 273100 Lingcheng high tech Industrial Development Zone, Qufu City, Jining City, Shandong Province Patentee after: Shandong Baifu Furuida Pharmaceutical Co.,Ltd. Address before: 273100 Lingcheng high tech Industrial Development Zone, Qufu City, Jining City, Shandong Province Patentee before: Focus biomedical Co.,Ltd. |
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Denomination of invention: A method for preparing instant sodium hyaluronate Effective date of registration: 20230324 Granted publication date: 20200616 Pledgee: Qufu sub branch of Postal Savings Bank of China Ltd. Pledgor: Shandong Baifu Furuida Pharmaceutical Co.,Ltd. Registration number: Y2023980035847 |
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Effective date of registration: 20240829 Address after: 273100 Economic Development Zone of Qufu High Speed Railway New Area, Jining City, Shandong Province Patentee after: Shandong focus furida biological Co.,Ltd. Country or region after: China Address before: 273100 Lingcheng high tech Industrial Development Zone, Qufu City, Jining City, Shandong Province Patentee before: Shandong Baifu Furuida Pharmaceutical Co.,Ltd. Country or region before: China |