JP6893356B2 - シキミ酸の製造方法 - Google Patents
シキミ酸の製造方法 Download PDFInfo
- Publication number
- JP6893356B2 JP6893356B2 JP2017161507A JP2017161507A JP6893356B2 JP 6893356 B2 JP6893356 B2 JP 6893356B2 JP 2017161507 A JP2017161507 A JP 2017161507A JP 2017161507 A JP2017161507 A JP 2017161507A JP 6893356 B2 JP6893356 B2 JP 6893356B2
- Authority
- JP
- Japan
- Prior art keywords
- shikimic acid
- exchange resin
- enzyme
- acid
- extract
- 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.)
- Active
Links
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 title claims description 332
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 title claims description 332
- 239000000243 solution Substances 0.000 claims description 97
- 241000196324 Embryophyta Species 0.000 claims description 78
- 108090000790 Enzymes Proteins 0.000 claims description 70
- 102000004190 Enzymes Human genes 0.000 claims description 70
- 238000004519 manufacturing process Methods 0.000 claims description 67
- 238000000605 extraction Methods 0.000 claims description 54
- 239000007788 liquid Substances 0.000 claims description 52
- 239000002904 solvent Substances 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 46
- 239000003463 adsorbent Substances 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
- 239000003957 anion exchange resin Substances 0.000 claims description 40
- 230000002209 hydrophobic effect Effects 0.000 claims description 35
- 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 claims description 29
- 239000003456 ion exchange resin Substances 0.000 claims description 29
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 29
- 240000007232 Illicium verum Species 0.000 claims description 27
- 235000008227 Illicium verum Nutrition 0.000 claims description 26
- 238000000926 separation method Methods 0.000 claims description 18
- 238000004255 ion exchange chromatography Methods 0.000 claims description 11
- 239000003929 acidic solution Substances 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 238000010828 elution Methods 0.000 claims description 6
- 229940088598 enzyme Drugs 0.000 description 67
- 239000011347 resin Substances 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 15
- 239000000126 substance Substances 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- 239000002994 raw material Substances 0.000 description 14
- 239000012535 impurity Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 241000720991 Illicium Species 0.000 description 8
- 238000005349 anion exchange Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000010419 fine particle Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 210000002421 cell wall Anatomy 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 238000000108 ultra-filtration Methods 0.000 description 5
- 108010059892 Cellulase Proteins 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 108010059820 Polygalacturonase Proteins 0.000 description 4
- 101710184309 Probable sucrose-6-phosphate hydrolase Proteins 0.000 description 4
- 102400000472 Sucrase Human genes 0.000 description 4
- 101710112652 Sucrose-6-phosphate hydrolase Proteins 0.000 description 4
- 150000001720 carbohydrates Chemical class 0.000 description 4
- 229940106157 cellulase Drugs 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 230000000593 degrading effect Effects 0.000 description 4
- 108010093305 exopolygalacturonase Proteins 0.000 description 4
- 235000011073 invertase Nutrition 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 3
- 241000533845 Enterolobium cyclocarpum Species 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 229920006037 cross link polymer Polymers 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 239000002608 ionic liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101710121765 Endo-1,4-beta-xylanase Proteins 0.000 description 2
- 241000198061 Illicium henryi Species 0.000 description 2
- 108010014251 Muramidase Proteins 0.000 description 2
- 102000016943 Muramidase Human genes 0.000 description 2
- 108010062010 N-Acetylmuramoyl-L-alanine Amidase Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005341 cation exchange Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 235000011869 dried fruits Nutrition 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 229960000274 lysozyme Drugs 0.000 description 2
- 239000004325 lysozyme Substances 0.000 description 2
- 235000010335 lysozyme Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012466 permeate Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- 229920000875 Dissolving pulp Polymers 0.000 description 1
- 235000011201 Ginkgo Nutrition 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- 240000003157 Illicium floridanum Species 0.000 description 1
- 235000008226 Illicium floridanum Nutrition 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical group CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000383833 Pachyphyllum Species 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- -1 aromatic amino acids Chemical class 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002036 drum drying Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical group C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 230000010399 physical interaction Effects 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 150000003364 shikimic acids Chemical class 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/32—Unsaturated compounds containing hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2017161507A JP6893356B2 (ja) | 2017-08-24 | 2017-08-24 | シキミ酸の製造方法 |
| CN201880069241.8A CN111278799A (zh) | 2017-08-24 | 2018-08-23 | 莽草酸的制造方法 |
| PCT/JP2018/031182 WO2019039553A1 (fr) | 2017-08-24 | 2018-08-23 | Procédé de production d'acide shikimique |
| JP2021087724A JP7058891B2 (ja) | 2017-08-24 | 2021-05-25 | シキミ酸の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2017161507A JP6893356B2 (ja) | 2017-08-24 | 2017-08-24 | シキミ酸の製造方法 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021087724A Division JP7058891B2 (ja) | 2017-08-24 | 2021-05-25 | シキミ酸の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2019038771A JP2019038771A (ja) | 2019-03-14 |
| JP6893356B2 true JP6893356B2 (ja) | 2021-06-23 |
Family
ID=65438960
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017161507A Active JP6893356B2 (ja) | 2017-08-24 | 2017-08-24 | シキミ酸の製造方法 |
| JP2021087724A Active JP7058891B2 (ja) | 2017-08-24 | 2021-05-25 | シキミ酸の製造方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021087724A Active JP7058891B2 (ja) | 2017-08-24 | 2021-05-25 | シキミ酸の製造方法 |
Country Status (3)
| Country | Link |
|---|---|
| JP (2) | JP6893356B2 (fr) |
| CN (1) | CN111278799A (fr) |
| WO (1) | WO2019039553A1 (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111056941B (zh) * | 2019-12-26 | 2022-07-05 | 浙江康恩贝制药股份有限公司 | 一种利用银杏叶提取物层析废液制备高纯度莽草酸的方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1978422B (zh) * | 2005-12-08 | 2011-07-20 | 中国科学院上海药物研究所 | 莽草酸的分离纯化方法 |
| US20070149805A1 (en) * | 2005-12-23 | 2007-06-28 | Stephen F. Austin State University | Method for the extraction and purification of shikimic acid |
| US20070161818A1 (en) * | 2006-01-06 | 2007-07-12 | Shiyou Li | Processes for the extraction and purification of shikimic acid and the products of such processes |
| CN101318893B (zh) * | 2006-08-25 | 2011-07-20 | 江南大学 | 一种从八角中同时提取莽草酸和香精油的工艺 |
| CN100408541C (zh) * | 2006-09-29 | 2008-08-06 | 广西万山香料有限责任公司 | 从八角中提取分离莽草酸的方法 |
| CN101024609B (zh) * | 2007-03-30 | 2010-07-07 | 南京农业大学 | 一种莽草酸的生产工艺 |
| CN101391951A (zh) | 2007-09-18 | 2009-03-25 | 兴化格林生物制品有限公司 | 高纯度莽草酸的生产制备工艺 |
| CN101759557A (zh) * | 2009-11-20 | 2010-06-30 | 南京泽朗医药科技有限公司 | 一种莽草酸的制备方法 |
| JP5737751B2 (ja) * | 2011-03-09 | 2015-06-17 | 学校法人上智学院 | シキミ酸取得方法及びシキミ酸製造方法 |
| WO2014189357A1 (fr) * | 2013-05-21 | 2014-11-27 | Sime Darby Malaysia Berhad | Procédé d'extraction d'un composé phénolique |
| CN106278873A (zh) * | 2016-08-19 | 2017-01-04 | 广西甙元植物制品有限公司 | 一种从八角中提取分离莽草酸的生产工艺 |
-
2017
- 2017-08-24 JP JP2017161507A patent/JP6893356B2/ja active Active
-
2018
- 2018-08-23 CN CN201880069241.8A patent/CN111278799A/zh active Pending
- 2018-08-23 WO PCT/JP2018/031182 patent/WO2019039553A1/fr active Application Filing
-
2021
- 2021-05-25 JP JP2021087724A patent/JP7058891B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| JP7058891B2 (ja) | 2022-04-25 |
| CN111278799A (zh) | 2020-06-12 |
| JP2021121631A (ja) | 2021-08-26 |
| WO2019039553A1 (fr) | 2019-02-28 |
| JP2019038771A (ja) | 2019-03-14 |
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