JP5714963B2 - キチン分解物の製造方法 - Google Patents
キチン分解物の製造方法 Download PDFInfo
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- JP5714963B2 JP5714963B2 JP2011087154A JP2011087154A JP5714963B2 JP 5714963 B2 JP5714963 B2 JP 5714963B2 JP 2011087154 A JP2011087154 A JP 2011087154A JP 2011087154 A JP2011087154 A JP 2011087154A JP 5714963 B2 JP5714963 B2 JP 5714963B2
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- chitin
- hours
- acetylglucosamine
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- degradation product
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- 229920002101 Chitin Polymers 0.000 title claims description 178
- 239000007857 degradation product Substances 0.000 title claims description 51
- 238000004519 manufacturing process Methods 0.000 title claims description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 86
- 238000006460 hydrolysis reaction Methods 0.000 claims description 60
- 230000035484 reaction time Effects 0.000 claims description 56
- 230000007062 hydrolysis Effects 0.000 claims description 53
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 229920001542 oligosaccharide Polymers 0.000 claims description 45
- 150000002482 oligosaccharides Chemical class 0.000 claims description 44
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- OVRNDRQMDRJTHS-UHFFFAOYSA-N N-acelyl-D-glucosamine Natural products CC(=O)NC1C(O)OC(CO)C(O)C1O OVRNDRQMDRJTHS-UHFFFAOYSA-N 0.000 description 69
- MBLBDJOUHNCFQT-LXGUWJNJSA-N N-acetylglucosamine Natural products CC(=O)N[C@@H](C=O)[C@@H](O)[C@H](O)[C@H](O)CO MBLBDJOUHNCFQT-LXGUWJNJSA-N 0.000 description 69
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 67
- 229950006780 n-acetylglucosamine Drugs 0.000 description 67
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 21
- 235000000346 sugar Nutrition 0.000 description 19
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 18
- 238000011033 desalting Methods 0.000 description 18
- 238000005342 ion exchange Methods 0.000 description 18
- 238000006386 neutralization reaction Methods 0.000 description 18
- 229960002442 glucosamine Drugs 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- 238000003381 deacetylation reaction Methods 0.000 description 14
- 239000012452 mother liquor Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 150000008163 sugars Chemical class 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 230000006196 deacetylation Effects 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- PLJAKLUDUPBLGD-VLWZLFBZSA-N N-acetyl-beta-D-glucosaminyl-(1->4)-N-acetyl-aldehydo-D-glucosamine Chemical compound CC(=O)N[C@@H](C=O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1NC(C)=O PLJAKLUDUPBLGD-VLWZLFBZSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 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 5
- 239000003729 cation exchange resin Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 241000238557 Decapoda Species 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002772 monosaccharides Chemical class 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 3
- 235000013325 dietary fiber Nutrition 0.000 description 3
- 150000002016 disaccharides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 150000004044 tetrasaccharides Chemical class 0.000 description 3
- 150000004043 trisaccharides Chemical class 0.000 description 3
- 241000238366 Cephalopoda Species 0.000 description 2
- 229920001661 Chitosan Polymers 0.000 description 2
- 241000238424 Crustacea Species 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- FZHXIRIBWMQPQF-UHFFFAOYSA-N Glc-NH2 Natural products O=CC(N)C(O)C(O)C(O)CO FZHXIRIBWMQPQF-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- OVRNDRQMDRJTHS-RTRLPJTCSA-N N-acetyl-D-glucosamine Chemical compound CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-RTRLPJTCSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000003957 anion exchange resin Substances 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000000909 electrodialysis Methods 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 102000012286 Chitinases Human genes 0.000 description 1
- 108010022172 Chitinases Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000000850 deacetylating effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 150000002301 glucosamine derivatives Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000003308 immunostimulating effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Images
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- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
Claims (4)
- 100cps以下の粘度で5mm以下に粉砕され水分率が10%以下のキチンと、35%の濃塩酸とだけを、撹拌機能を有し外部から調温できる濃塩酸の影響を受けない反応層に入れて密閉することによって、この濃塩酸の濃度を低下させることなく高い状態に保ちつつ反応温度5℃以上25℃以下にて加水分解する加水分解工程を有し、製造するキチン分解物の種類に応じて前記加水分解工程における反応時間を5時間以上96時間以下の範囲で設定することを特徴とするキチン分解物の製造方法。
- 前記濃塩酸は、前記キチンに対し3倍量以上12倍量以下であることを特徴とする請求項1に記載のキチン分解物の製造方法。
- 前記反応時間を5時間以上24時間以下に設定して、キチンオリゴ糖を含むキチン分解物を製造することを特徴とする請求項1又は2に記載のキチン分解物の製造方法。
- 前記反応時間を48時間以上96時間以下に設定して、Nアセチルグルコミサンを製造することを特徴とする請求項1乃至3にいずれかに記載のキチン分解物の製造方法。
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JP2011087154A JP5714963B2 (ja) | 2011-04-11 | 2011-04-11 | キチン分解物の製造方法 |
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JP2011087154A JP5714963B2 (ja) | 2011-04-11 | 2011-04-11 | キチン分解物の製造方法 |
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JP2012217396A JP2012217396A (ja) | 2012-11-12 |
JP5714963B2 true JP5714963B2 (ja) | 2015-05-07 |
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JPWO2022202296A1 (ja) | 2021-03-23 | 2022-09-29 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS61271296A (ja) * | 1985-05-28 | 1986-12-01 | Kyogyo Kumiai N F I | N−アセチルキトオリゴ糖の製造方法 |
JPS63273493A (ja) * | 1987-04-30 | 1988-11-10 | Kyogyo Kumiai N F I | N−アセチル−d−グルコサミンの製造法 |
JPH05230092A (ja) * | 1992-02-20 | 1993-09-07 | Snow Brand Milk Prod Co Ltd | N−アセチルグルコサミン結合オリゴ糖及びその製造方法 |
JPH11276189A (ja) * | 1998-03-30 | 1999-10-12 | Tottori Prefecture | 非晶質の水溶性部分脱アセチル化キチンを基質とする酵素によるオリゴ糖の製造方法 |
JP2000281696A (ja) * | 1999-03-29 | 2000-10-10 | Yaizu Suisankagaku Industry Co Ltd | 天然型n−アセチル−d−グルコサミンの製造法 |
JP2002088093A (ja) * | 2000-09-14 | 2002-03-27 | Eniwa Research Business Park Co Ltd | キチンオリゴ糖の製造方法 |
JP4588205B2 (ja) * | 2000-12-15 | 2010-11-24 | 日本水産株式会社 | キチンオリゴ糖製造方法 |
JP4105615B2 (ja) * | 2003-09-10 | 2008-06-25 | 焼津水産化学工業株式会社 | 乳飲料及び変形性関節症改善剤並びに乳飲料の製造方法 |
JP4276500B2 (ja) * | 2003-09-10 | 2009-06-10 | 焼津水産化学工業株式会社 | N−アセチルグルコサミンを含有する糖組成物の製造方法及び該方法を利用した飲食品の製造方法 |
JP4672994B2 (ja) * | 2004-03-31 | 2011-04-20 | 焼津水産化学工業株式会社 | キチン分解物の製造方法 |
JP4738856B2 (ja) * | 2005-03-23 | 2011-08-03 | 焼津水産化学工業株式会社 | N−アセチルグルコサミン含有組成物の製造方法 |
JP2006327979A (ja) * | 2005-05-25 | 2006-12-07 | Yaizu Suisankagaku Industry Co Ltd | 関節軟骨損傷治癒促進剤及び腱損傷治癒促進剤、並びにそれらを含有する飲食品 |
JP5320565B2 (ja) * | 2007-03-01 | 2013-10-23 | 独立行政法人国立高等専門学校機構 | キチン分解物の製造方法 |
JP5256509B2 (ja) * | 2008-01-18 | 2013-08-07 | 甲陽ケミカル株式会社 | N−アセチルグルコサミンの製造方法、並びにその用途 |
JP5426099B2 (ja) * | 2008-02-14 | 2014-02-26 | 南海化学株式会社 | 天然型n−アセチルグルコサミンの製造方法 |
JP5564205B2 (ja) * | 2009-06-05 | 2014-07-30 | 焼津水産化学工業株式会社 | 皮膚掻痒症改善剤 |
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