KR100876509B1 - 산화 방호 효과가 높은 용매를 사용한 환원형 보효소q10의 제조 방법 - Google Patents
산화 방호 효과가 높은 용매를 사용한 환원형 보효소q10의 제조 방법 Download PDFInfo
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- KR100876509B1 KR100876509B1 KR1020047000449A KR20047000449A KR100876509B1 KR 100876509 B1 KR100876509 B1 KR 100876509B1 KR 1020047000449 A KR1020047000449 A KR 1020047000449A KR 20047000449 A KR20047000449 A KR 20047000449A KR 100876509 B1 KR100876509 B1 KR 100876509B1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/46—Use of additives, e.g. for stabilisation
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/814—Enzyme separation or purification
- Y10S435/816—Enzyme separation or purification by solubility
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Abstract
Description
R | ||
실시예 2 | 헵탄 헥산 톨루엔 클로로포름 아세트산에틸 메틸tert-부틸에테르 테트라히드로피란 | 99.1/0.9 98.7/1.3 98.8/1.2 98.9/1.1 98.9/1.1 98.6/1,4 98.5/1.5 |
비교예 1 | 메틸이소부틸케톤 디메틸포름아미드 N-메틸-피롤리돈 결정 | 69.2/30.8 31.0/69.0 67.3/32.7 95.9/4.1 |
용매 | R | |
실시예 3 | 헵탄 아세트산에틸 아세토니트릴 | 96.7/3.3 96.4/3.6 96.0/4.0 |
비교예 2 | 메틸이소부틸케톤 | 46.1/53.9 |
용매 | R |
헵탄 헥산 아세트산에틸 메틸tert-부틸에테르 톨루엔 클로로포름 | 99.5/0.5 99.3/0.7 99.4/0.6 99.2/0.8 99.4/0.6 99.3/0.7 |
Claims (54)
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- 환원형 보효소 Q10을 탄화수소류, 지방산 에스테르류, 에테르류 및 니트릴류로부터 선택되는 적어도 1종을 용매로서 사용하여 결정화하는 것을 특징으로 하는 환원형 보효소 Q10의 결정화 방법.
- 제15항에 있어서, 지방족 탄화수소를 용매로서 사용하는 결정화 방법.
- 제16항에 있어서, 지방족 탄화수소가 비환상 지방족 탄화수소인 결정화 방법.
- 제16항에 있어서, 지방족 탄화수소가 펜탄류, 헥산류, 헵탄류 및 옥탄류로부터 선택되는 적어도 1종인 결정화 방법.
- 제15항 내지 제18항 중 어느 한 항에 있어서, 불순물을 모액에서 제거하는 결정화 방법.
- 제19항에 있어서, 제거되는 불순물이 환원형 보효소 Q9, 환원형 보효소 Q8, 및 환원형 보효소 Q7로부터 선택되는 적어도 1종인 결정화 방법.
- 제15항 내지 제18항 중 어느 한 항에 있어서, 환원형 보효소 Q10의 결정화는 냉각 결정화, 또는 냉각 결정화에 다른 결정화법을 조합하여 행하는 결정화 방법.
- 제21항에 있어서, 결정화시의 냉각 온도가 20 ℃ 이하인 결정화 방법.
- 제15항 내지 제18항 중 어느 한 항에 있어서, 결정화 농도가 결정화 종료 시의 결정화 용매의 중량에 대한 환원형 보효소 Q10의 중량으로서 15 w/w% 이하인 결정화 방법.
- 제15항 내지 제18항 중 어느 한 항에 있어서, 결정화가 단위 용적당 교반 소요 동력으로서 0.O1 kW/m3 이상의 강제 유동하에서 실시되는 결정화 방법.
- 제15항 내지 제18항 중 어느 한 항에 있어서, 결정화에 있어서 결정핵을 첨가하는 결정화 방법.
- 제15항 내지 제18항 중 어느 한 항에 있어서, 탈산소 분위기하에서 실시하는 결정화 방법.
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- 삭제
- 삭제
- 환원형 보효소 Q10/산화형 보효소 Q10의 중량비가 96/4 이상인 환원형 보효소 Q10 결정.
- 산화형 보효소 Q10을 환원하여 환원형 보효소 Q10을 합성하는 방법에 있어서, 헥산을 제외한 탄화수소류, 지방산 에스테르류, 에테르류 및 니트릴류로부터 선택되는 적어도 1종을 용매로서 이용하는 것을 특징으로 하는 환원형 보효소 Q10의 제조 방법.
- 제37항에 있어서, 용매로서 지방산 에스테르류 및 니트릴류로부터 선택되는 적어도 1종을 사용하는 제조 방법.
- 제37항 또는 제38항에 있어서, 환원을 탈산소 분위기하에서 행하는 제조 방법.
- 산화형 보효소 Q10을 환원하여 환원형 보효소 Q10을 합성하는 방법에 있어서, 탈산소 분위기하에서 탄화수소류 및(또는) 에테르류를 용매로서 사용하는 것을 특징으로 하는 환원형 보효소 Q10의 제조 방법.
- 제40항에 있어서, 용매로서 탄화수소류를 사용하는 제조 방법.
- 제41항에 있어서, 용매로서 헵탄류를 사용하는 제조 방법.
- 제40항에 있어서, 용매로서 에테르류를 사용하는 제조 방법.
- 제37항 또는 제40항에 있어서, 환원제로서 수소화 금속 화합물, 철, 또는 아연을 사용하는 제조 방법.
- 제37항 또는 제40항에 있어서, 환원제로서 차아황산류를 사용하고, 물 공존하에서 환원을 행하는 제조 방법.
- 제45항에 있어서, 환원을 pH 3 내지 7에서 행하는 제조 방법.
- 제45항에 있어서, 차아황산류의 사용량이 산화형 보효소 Q10과 동일 중량 이하인 제조 방법.
- 제37항 또는 제40항에 있어서, 환원제로서 아스코르빈산류를 사용하여 실시하는 제조 방법.
- 제48항에 있어서, 용매로서 테트라히드로푸란, 디옥산 및 아세토니트릴로부터 선택되는 적어도 1종을 사용하는 것을 특징으로 하는 제조 방법.
- 제48항에 있어서, 아스코르빈산류의 사용량이 산화형 보효소 Q10에 대하여 1 배몰 이상인 제조 방법.
- 제48항에 있어서, 염기성 물질 또는 아황산수소염의 공존하에서 환원을 행하는 제조 방법.
- 제37항 또는 제40항에 있어서, 환원 반응 후, 생성된 환원형 보효소 Q10을 함유하는 유기상을 채취하고, 이 유기상을 세척하는 제조 방법.
- 제15항에 있어서, 결정화에 사용하는 환원형 보효소 Q10은 제37항 또는 제40항에 기재된 방법에 의해 얻어진 것인 결정화 방법.
- 제15항에 있어서, 제37항 또는 제40항에 기재된 방법으로 얻어진 환원 반응액, 또는 이 반응액으로부터 환원형 보효소 Q10을 포함하는 유기상을 채취하여 얻어진 용액으로부터 환원형 보효소 Q10을 결정화하는 결정화 방법.
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JPJP-P-2001-00214471 | 2001-07-13 | ||
JP2001214471 | 2001-07-13 | ||
JPJP-P-2002-00114854 | 2002-04-17 | ||
JP2002114854 | 2002-04-17 | ||
PCT/JP2002/007143 WO2003006408A1 (en) | 2001-07-13 | 2002-07-15 | Method of producing reduced coenzyme q10 using solvent with high oxidation-protective effect |
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KR100876509B1 true KR100876509B1 (ko) | 2008-12-31 |
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EP (4) | EP1415969A4 (ko) |
JP (1) | JP4057523B2 (ko) |
KR (1) | KR100876509B1 (ko) |
CN (3) | CN1527807A (ko) |
AU (1) | AU2002318843B2 (ko) |
CA (1) | CA2453158C (ko) |
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TWI305547B (en) | 2001-12-27 | 2009-01-21 | Kaneka Corp | Processes for producing coenzyme q10 |
US7358402B2 (en) | 2003-09-10 | 2008-04-15 | Kaneka Corporation | Reduced coenzyme Q10 crystal with excellent stability and composition containing said reduced coenzyme Q10 crystal |
CN100534968C (zh) * | 2003-09-10 | 2009-09-02 | 株式会社钟化 | 稳定性优异的还原型辅酶q10 结晶及含有还原型辅酶q10结晶的组合物 |
US20060147542A1 (en) * | 2004-12-24 | 2006-07-06 | Tadao Ono | Solid preparation containing reduced coenzyme Q10 and method for producing the same |
US8067217B2 (en) | 2004-12-28 | 2011-11-29 | Kaneka Corporation | Method for preserving reduced coenzyme Q10 |
EP1870095A4 (en) * | 2005-03-29 | 2010-10-13 | Kaneka Corp | COMPOSITION FOR INCREASING ANTI-OXIDATION ACTIVITY IN BLOOD |
JP4469772B2 (ja) * | 2005-09-15 | 2010-05-26 | 株式会社資生堂 | コエンザイムq10高負荷細胞の作製方法、コエンザイムq10高負荷細胞増殖添加剤及びコエンザイムq10高負荷培地 |
US8506956B2 (en) | 2005-10-31 | 2013-08-13 | Kaneka Corporation | Method for stabilizing reduced coenzyme Q10 |
WO2007126086A1 (ja) | 2006-04-28 | 2007-11-08 | Kaneka Corporation | 還元型補酵素q10の精製方法 |
AU2007244232B2 (en) | 2006-04-28 | 2012-07-19 | Kaneka Corporation | Method for stabilization of reduced coenzyme Q10 |
JP5286086B2 (ja) * | 2006-09-08 | 2013-09-11 | 株式会社カネカ | 還元型補酵素q10及びリゾレシチンを含有する組成物 |
WO2009044852A1 (ja) * | 2007-10-05 | 2009-04-09 | Kaneka Corporation | 還元型補酵素q10の製造方法 |
US8063254B2 (en) | 2007-10-30 | 2011-11-22 | Kaneka Corporation | Method for production of reduced coenzyme Q10 using water-containing organic solvent |
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JP4855551B2 (ja) * | 2009-10-16 | 2012-01-18 | 株式会社カネカ | 還元型補酵素q10の製造方法、安定化方法及びそれを含有する組成物 |
EP2563164B1 (en) | 2010-03-23 | 2016-06-29 | Virun, Inc. | Nanoemulsion including sucrose fatty acid ester |
JP5546935B2 (ja) * | 2010-04-20 | 2014-07-09 | 株式会社カネカ | 還元型補酵素q10含有組成物及びその製法方法 |
US8741373B2 (en) | 2010-06-21 | 2014-06-03 | Virun, Inc. | Compositions containing non-polar compounds |
EP2725004B1 (en) | 2011-06-24 | 2018-02-28 | Kaneka Corporation | Reduced coenzyme q10 crystal having excellent stability |
SG11201404640YA (en) | 2012-02-10 | 2014-09-26 | Virun Inc | Beverage compositions containing non-polar compounds |
JP2013224272A (ja) * | 2012-04-20 | 2013-10-31 | Idemitsu Kosan Co Ltd | 1−アダマンタノールの製造方法 |
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JPWO2003006408A1 (ja) | 2004-10-28 |
CN101774996B (zh) | 2015-02-11 |
CN101906026A (zh) | 2010-12-08 |
US20040215040A1 (en) | 2004-10-28 |
CA2453158C (en) | 2011-05-24 |
KR20040017293A (ko) | 2004-02-26 |
WO2003006408A1 (en) | 2003-01-23 |
TWI310029B (ko) | 2009-05-21 |
CA2453158A1 (en) | 2003-01-23 |
CN1527807A (zh) | 2004-09-08 |
EP1415969A4 (en) | 2005-04-27 |
EP3321248A3 (en) | 2018-06-06 |
US7145044B2 (en) | 2006-12-05 |
AU2002318843A2 (en) | 2003-01-29 |
CN101774996A (zh) | 2010-07-14 |
EP2402303A3 (en) | 2012-04-25 |
EP2402303A2 (en) | 2012-01-04 |
JP4057523B2 (ja) | 2008-03-05 |
EP2228360A1 (en) | 2010-09-15 |
AU2002318843B2 (en) | 2008-10-30 |
EP1415969A1 (en) | 2004-05-06 |
EP3321248A2 (en) | 2018-05-16 |
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