JPS59166504A - ヒアルロン酸の製造法 - Google Patents
ヒアルロン酸の製造法Info
- Publication number
- JPS59166504A JPS59166504A JP3962483A JP3962483A JPS59166504A JP S59166504 A JPS59166504 A JP S59166504A JP 3962483 A JP3962483 A JP 3962483A JP 3962483 A JP3962483 A JP 3962483A JP S59166504 A JPS59166504 A JP S59166504A
- Authority
- JP
- Japan
- Prior art keywords
- filtrate
- solution
- added
- filtration
- hyaluronic acid
- 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
- 229920002674 hyaluronan Polymers 0.000 title claims description 37
- 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 title claims description 36
- 229960003160 hyaluronic acid Drugs 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 239000000706 filtrate Substances 0.000 claims abstract description 26
- 239000002244 precipitate Substances 0.000 claims abstract description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 14
- 102000004169 proteins and genes Human genes 0.000 claims abstract description 13
- 108090000623 proteins and genes Proteins 0.000 claims abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 12
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000284 extract Substances 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims abstract description 9
- 239000003957 anion exchange resin Substances 0.000 claims abstract description 7
- 239000011780 sodium chloride Substances 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 6
- 238000001914 filtration Methods 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 108091005804 Peptidases Proteins 0.000 claims description 16
- 239000004365 Protease Substances 0.000 claims description 16
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 15
- 238000000605 extraction Methods 0.000 claims description 14
- 241000287828 Gallus gallus Species 0.000 claims description 10
- 108010059712 Pronase Proteins 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 3
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 claims description 2
- YPHMISFOHDHNIV-FSZOTQKASA-N cycloheximide Chemical compound C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims 3
- 102000003425 Tyrosinase Human genes 0.000 claims 1
- 108060008724 Tyrosinase Proteins 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 229960001927 cetylpyridinium chloride Drugs 0.000 abstract description 8
- YMKDRGPMQRFJGP-UHFFFAOYSA-M cetylpyridinium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 YMKDRGPMQRFJGP-UHFFFAOYSA-M 0.000 abstract description 7
- 239000000047 product Substances 0.000 abstract description 5
- 210000001520 comb Anatomy 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 3
- 241000561734 Celosia cristata Species 0.000 abstract description 2
- 230000001376 precipitating effect Effects 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 210000003954 umbilical cord Anatomy 0.000 abstract 2
- 241000272496 Galliformes Species 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000003906 humectant Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 32
- 239000000243 solution Substances 0.000 description 29
- 239000000287 crude extract Substances 0.000 description 14
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229920002683 Glycosaminoglycan Polymers 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229960004319 trichloroacetic acid Drugs 0.000 description 6
- 238000012545 processing Methods 0.000 description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 102000016938 Catalase Human genes 0.000 description 3
- 108010053835 Catalase Proteins 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000003020 moisturizing effect Effects 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- SQDAZGGFXASXDW-UHFFFAOYSA-N 5-bromo-2-(trifluoromethoxy)pyridine Chemical compound FC(F)(F)OC1=CC=C(Br)C=N1 SQDAZGGFXASXDW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920001287 Chondroitin sulfate Polymers 0.000 description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229940059329 chondroitin sulfate Drugs 0.000 description 2
- 238000004925 denaturation Methods 0.000 description 2
- 230000036425 denaturation Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- 238000010257 thawing Methods 0.000 description 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 241000201841 Celosia Species 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 229910052776 Thorium Inorganic materials 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229920001284 acidic polysaccharide Polymers 0.000 description 1
- 150000004805 acidic polysaccharides Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000012812 general test Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940079889 pyrrolidonecarboxylic acid Drugs 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229950003937 tolonium Drugs 0.000 description 1
- HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
Landscapes
- Polysaccharides And Polysaccharide Derivatives (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3962483A JPS59166504A (ja) | 1983-03-10 | 1983-03-10 | ヒアルロン酸の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3962483A JPS59166504A (ja) | 1983-03-10 | 1983-03-10 | ヒアルロン酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59166504A true JPS59166504A (ja) | 1984-09-19 |
| JPS6254324B2 JPS6254324B2 (en, 2012) | 1987-11-14 |
Family
ID=12558254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3962483A Granted JPS59166504A (ja) | 1983-03-10 | 1983-03-10 | ヒアルロン酸の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59166504A (en, 2012) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63270701A (ja) * | 1987-04-30 | 1988-11-08 | Nippon Kayaku Co Ltd | ヒアルロン酸の精製法 |
| WO1989006243A1 (en) * | 1986-07-03 | 1989-07-13 | Kyowa Hakko Kogyo Co., Ltd. | Process for purifying hyaluronic acid |
| KR20020071772A (ko) * | 2001-03-06 | 2002-09-13 | (주)신스바이오 | 항균 활동성을 갖는 히알루론산의 제조방법 |
| ES2192960A1 (es) * | 2001-11-16 | 2003-10-16 | Consejo Superior Investigacion | Nuevo procedimiento de obtencion de acido hialuronico. |
| JP2008280430A (ja) * | 2007-05-10 | 2008-11-20 | Mitsubishi Rayon Co Ltd | ヒアルロン酸の製造方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0464615U (en, 2012) * | 1990-10-17 | 1992-06-03 | ||
| JP6675651B1 (ja) * | 2018-11-26 | 2020-04-01 | 株式会社ＦｉＮＣ Ｔｅｃｈｎｏｌｏｇｉｅｓ | 健康管理システム及びプログラム |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52105199A (en) * | 1976-03-01 | 1977-09-03 | Seikagaku Kogyo Co Ltd | Isolation of acidic polysaccharide |
-
1983
- 1983-03-10 JP JP3962483A patent/JPS59166504A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52105199A (en) * | 1976-03-01 | 1977-09-03 | Seikagaku Kogyo Co Ltd | Isolation of acidic polysaccharide |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989006243A1 (en) * | 1986-07-03 | 1989-07-13 | Kyowa Hakko Kogyo Co., Ltd. | Process for purifying hyaluronic acid |
| JPS63270701A (ja) * | 1987-04-30 | 1988-11-08 | Nippon Kayaku Co Ltd | ヒアルロン酸の精製法 |
| KR20020071772A (ko) * | 2001-03-06 | 2002-09-13 | (주)신스바이오 | 항균 활동성을 갖는 히알루론산의 제조방법 |
| ES2192960A1 (es) * | 2001-11-16 | 2003-10-16 | Consejo Superior Investigacion | Nuevo procedimiento de obtencion de acido hialuronico. |
| JP2008280430A (ja) * | 2007-05-10 | 2008-11-20 | Mitsubishi Rayon Co Ltd | ヒアルロン酸の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6254324B2 (en, 2012) | 1987-11-14 |
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