KR100548989B1 - 3-o-치환된-아스코르빈산의 제조방법 - Google Patents
3-o-치환된-아스코르빈산의 제조방법 Download PDFInfo
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- KR100548989B1 KR100548989B1 KR1020030022457A KR20030022457A KR100548989B1 KR 100548989 B1 KR100548989 B1 KR 100548989B1 KR 1020030022457 A KR1020030022457 A KR 1020030022457A KR 20030022457 A KR20030022457 A KR 20030022457A KR 100548989 B1 KR100548989 B1 KR 100548989B1
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- Prior art keywords
- acid
- ascorbic acid
- substituted
- alkyl
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- 229960005070 ascorbic acid Drugs 0.000 title claims abstract description 59
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 239000011668 ascorbic acid Substances 0.000 title description 31
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 81
- 239000002211 L-ascorbic acid Substances 0.000 claims abstract description 28
- 235000000069 L-ascorbic acid Nutrition 0.000 claims abstract description 28
- -1 3-O-substituted L-ascorbic acid Chemical class 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 150000001350 alkyl halides Chemical class 0.000 claims abstract description 6
- 238000000926 separation method Methods 0.000 claims abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- 150000000996 L-ascorbic acids Chemical class 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 2
- 235000019253 formic acid Nutrition 0.000 claims 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 2
- 229940071870 hydroiodic acid Drugs 0.000 claims 2
- 229910017604 nitric acid Inorganic materials 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 abstract description 8
- 125000006239 protecting group Chemical group 0.000 abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 239000003377 acid catalyst Substances 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 229940120145 3-o-ethylascorbic acid Drugs 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 239000011736 potassium bicarbonate Substances 0.000 description 3
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000007039 two-step reaction Methods 0.000 description 3
- 0 *C(*)(OC1)OC1C(C(O*)=C1O)OC1=O Chemical compound *C(*)(OC1)OC1C(C(O*)=C1O)OC1=O 0.000 description 2
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 2
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 2
- RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 2
- ZGSCRDSBTNQPMS-UJURSFKZSA-N 3-O-Ethylascorbic acid Chemical compound CCOC1=C(O)C(=O)O[C@@H]1[C@@H](O)CO ZGSCRDSBTNQPMS-UJURSFKZSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
- 206010014970 Ephelides Diseases 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 208000003351 Melanosis Diseases 0.000 description 1
- CIWBSHSKHKDKBQ-UHFFFAOYSA-N OCC(C(C(O)=C1O)OC1=O)O Chemical compound OCC(C(C(O)=C1O)OC1=O)O CIWBSHSKHKDKBQ-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 206010047623 Vitamin C deficiency Diseases 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 208000010233 scurvy Diseases 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E02—HYDRAULIC ENGINEERING; FOUNDATIONS; SOIL SHIFTING
- E02D—FOUNDATIONS; EXCAVATIONS; EMBANKMENTS; UNDERGROUND OR UNDERWATER STRUCTURES
- E02D31/00—Protective arrangements for foundations or foundation structures; Ground foundation measures for protecting the soil or the subsoil water, e.g. preventing or counteracting oil pollution
- E02D31/10—Protective arrangements for foundations or foundation structures; Ground foundation measures for protecting the soil or the subsoil water, e.g. preventing or counteracting oil pollution against soil pressure or hydraulic pressure
- E02D31/12—Protective arrangements for foundations or foundation structures; Ground foundation measures for protecting the soil or the subsoil water, e.g. preventing or counteracting oil pollution against soil pressure or hydraulic pressure against upward hydraulic pressure
-
- E—FIXED CONSTRUCTIONS
- E02—HYDRAULIC ENGINEERING; FOUNDATIONS; SOIL SHIFTING
- E02D—FOUNDATIONS; EXCAVATIONS; EMBANKMENTS; UNDERGROUND OR UNDERWATER STRUCTURES
- E02D2300/00—Materials
- E02D2300/0004—Synthetics
- E02D2300/0006—Plastics
- E02D2300/0015—HDPE
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Hydrology & Water Resources (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Mining & Mineral Resources (AREA)
- Paleontology (AREA)
- Civil Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Structural Engineering (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
Abstract
Description
Claims (8)
- 삭제
- 삭제
- 삭제
- 3-o-치환된 L-아스코르빈산을 제조하기 위한 중간체로서 사용되는 3-o-치환된 5,6-하이드록시그룹이 보호된(5,6-hydroxy protected group) L-아스코르빈산을 제조하는 방법에 있어서,하기 반응식 1의 L-아스코르빈산 및 L-아스코르빈산의 5번 빛 6번 위치의 하이드록시기를 보호하는 R1R2CO 또는 R1R2C(OR3)(OR4)에서 선택되는 화합물을 염산, 브롬화수소산, 요오드화수소산, 질산, 인산에서 선택되는 1종이상의 무기산 또는 포름산, 트리플르오르 아세트산, p-톨루엔술포닉산, 메탄술포닉산으로 이루어진 군으로부터 선택되는 1종이상의 유기산 및 디메틸 설폭사이드, 디메틸포름아미드, 메틸피롤리돈, 디메틸아세트아마이드, 아세토나이트릴에서 선택되는 1종이상의 유기용매 존재하에 반응시켜, 5,6-하이드록시그룹이 보호된 L-아스코르빈산을 제조하고,별도의 분리단계 없이 연속적으로 K2CO3를 투입한 후, C1 ~ C25의 알킬할라이드 또는 알케닐할라이드와 반응시켜 3-o-치환시킨 5,6-하이드록시그룹이 보호된 L-아스코르빈산을 1단계로 제조하는 제조방법.[반응식 1](상기 R1 ~ R4 및 R' , R"는 C1 ~ C7의 알킬 또는 알케닐기이고, R은 C1 ~ C25의 알킬, 알케닐, 카르보닐기이다.)
- 삭제
- 삭제
- 삭제
- 3-o-치환된 L-아스코르빈산의 제조방법에 있어서,1) L-아스코르빈산 및 L-아스코르빈산의 5번 및 6번 위치의 하이드록시기를 보호하는 R1R2CO 또는 R1R2C(OR3)(OR4)에서 선택되는 화합물을 염산, 브롬화수소산, 요오드화수소산, 질산, 인산에서 선택되는 1종이상의 무기산 또는 포름산, 트리플르오르 아세트산, p-톨루엔술포닉산, 메탄술포닉산으로 이루어진 군으로부터 선택되는 1종이상의 유기산 및 디메틸 설폭사이드, 디메틸포름아미드, 메틸피롤리돈, 디메틸아세트아마이드, 아세토나이트릴에서 선택되는 1종이상의 유기용매 존재 하에 반응시켜 5,6-하이드록시그룹 보호된 L-아스코르빈산을 제조하는 단계;2) 상기 1)단계 후 연속적으로 K2CO3의 존재 하에 C1 ~ C25의 알킬할라이드 또는 알케닐할라이드와 반응시켜 3-o-치환된 5,6-하이드록시그룹이 보호된 L-아스코르빈산을 제조하는 단계; 및3) 3-o-치환된 5,6-하이드록시그룹이 보호된 L-아스코르빈산을 염산 존재하에 물 및 에탄올의 혼합용매에서 반응시켜 3-o-치환된 L-아스코르빈산을 제조하는 단계;로 구성되는 3-o-치환된 L-아스코르빈산의 제조방법.[반응식](상기 R1 ~ R4 및 R' , R"는 C1 ~ C7의 알킬 또는 알케닐기이고, R은 C1 ~ C25의 알킬, 알케닐, 카르보닐기이다.)
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100974608B1 (ko) | 2007-04-18 | 2010-08-09 | 니폰 하이폭스 라보레토리즈 인코포레이티드 | 3-o-알킬-5,6-o-(1-메틸에틸리덴)-l-아스코르빈산의제조방법 및 5,6-o-(1-메틸에틸리덴)-l-아스코르빈산의제조방법 |
KR101119027B1 (ko) * | 2009-05-07 | 2012-03-14 | (주)코스몰 | 아스코르빈산 유도체의 제조방법 |
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KR100761959B1 (ko) | 2006-10-12 | 2007-10-04 | (주)코스몰 | 결정성 3-o-치환된 아스코르빈산의 제조방법 |
KR102325062B1 (ko) * | 2021-08-15 | 2021-11-11 | (주)삼양정밀화학 | 3-o-알킬-아스코르빈산의 제조방법 |
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Publication number | Priority date | Publication date | Assignee | Title |
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KR100974608B1 (ko) | 2007-04-18 | 2010-08-09 | 니폰 하이폭스 라보레토리즈 인코포레이티드 | 3-o-알킬-5,6-o-(1-메틸에틸리덴)-l-아스코르빈산의제조방법 및 5,6-o-(1-메틸에틸리덴)-l-아스코르빈산의제조방법 |
KR101119027B1 (ko) * | 2009-05-07 | 2012-03-14 | (주)코스몰 | 아스코르빈산 유도체의 제조방법 |
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