CA2837695C - Reduced coenzyme q10 crystal having excellent stability - Google Patents
Reduced coenzyme q10 crystal having excellent stability Download PDFInfo
- Publication number
- CA2837695C CA2837695C CA2837695A CA2837695A CA2837695C CA 2837695 C CA2837695 C CA 2837695C CA 2837695 A CA2837695 A CA 2837695A CA 2837695 A CA2837695 A CA 2837695A CA 2837695 C CA2837695 C CA 2837695C
- Authority
- CA
- Canada
- Prior art keywords
- reduced coenzyme
- crystal
- coenzyme
- crystalline solid
- present
- 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
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- 239000013078 crystal Substances 0.000 title claims abstract description 240
- QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 title claims abstract description 206
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 239000000843 powder Substances 0.000 claims abstract description 10
- 239000007787 solid Substances 0.000 claims description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 43
- 238000002425 crystallisation Methods 0.000 claims description 34
- 230000008025 crystallization Effects 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 28
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- 238000010521 absorption reaction Methods 0.000 claims description 8
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 239000002537 cosmetic Substances 0.000 claims description 5
- 235000015097 nutrients Nutrition 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
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- 235000013402 health food Nutrition 0.000 claims description 4
- 238000012844 infrared spectroscopy analysis Methods 0.000 claims description 4
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- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 239000013589 supplement Substances 0.000 claims description 4
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- 229910002483 Cu Ka Inorganic materials 0.000 claims description 2
- 238000007707 calorimetry Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 abstract description 17
- 230000008018 melting Effects 0.000 abstract description 17
- 238000000113 differential scanning calorimetry Methods 0.000 abstract description 12
- 229910017488 Cu K Inorganic materials 0.000 abstract 1
- 229910017541 Cu-K Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 description 30
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/10—Separation; Purification; Stabilisation; Use of additives
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A23K20/10—Organic substances
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- A—HUMAN NECESSITIES
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- A23K20/10—Organic substances
- A23K20/111—Aromatic compounds
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
- A23L2/52—Adding ingredients
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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- A—HUMAN NECESSITIES
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/35—Ketones, e.g. benzophenone
- A61K8/355—Quinones
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- A—HUMAN NECESSITIES
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- 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
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- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
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- 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
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- C07C41/46—Use of additives, e.g. for stabilisation
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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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/577—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/28—Quinones containing groups having oxygen atoms singly bound to carbon atoms with monocyclic quinoid structure
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nutrition Science (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Crystallography & Structural Chemistry (AREA)
- Emergency Medicine (AREA)
- Birds (AREA)
- Mycology (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
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| JP2011141028 | 2011-06-24 | ||
| JP2011-141028 | 2011-06-24 | ||
| PCT/JP2012/065869 WO2012176842A1 (ja) | 2011-06-24 | 2012-06-21 | 安定性に優れた還元型補酵素ｑ１０結晶 |
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| CA2837695A1 CA2837695A1 (en) | 2012-12-27 |
| CA2837695C true CA2837695C (en) | 2019-12-31 |
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| EP3327007B1 (en) | 2015-07-24 | 2020-06-03 | Shenzhen Zhenxing Medical Technology Co., Ltd. | Orbit azine-fumarate, hydrate, crystal form and preparation method therefor |
| JP7348663B2 (ja) * | 2018-02-23 | 2023-09-21 | センター フォー インテリジェント リサーチ イン クリスタル エンジニアリング，エセ．エレ． | ユビキノールの共結晶及びそれらを含む組成物 |
| EP3845515B1 (en) * | 2018-08-30 | 2025-11-12 | Kaneka Corporation | Production method for crystal of reduced coenzyme q10 having excellent stability |
| CN113166017B (zh) * | 2018-09-28 | 2024-03-29 | 株式会社钟化 | 稳定性优异的还原型辅酶q10结晶的制造方法 |
| US11471426B2 (en) | 2019-10-16 | 2022-10-18 | American River Nutrition, Llc | Compositions comprising quinone and/or quinol and methods of preparations and use thereof |
| CN115087631B (zh) * | 2020-02-12 | 2024-05-14 | 株式会社钟化 | FormII型的还原型辅酶Q10结晶的制造方法 |
| CN113024362B (zh) | 2021-03-10 | 2022-02-15 | 中国科学院上海药物研究所 | 一种辅酶qh与烟酰胺的共晶及其制备方法和用途 |
| JP7739411B2 (ja) * | 2021-03-26 | 2025-09-16 | 株式会社カネカ | ＦｏｒｍＩＩ型の還元型補酵素Ｑ１０結晶又はその結晶性固体の製造方法及び晶析装置 |
| WO2022202213A1 (ja) * | 2021-03-26 | 2022-09-29 | 株式会社カネカ | ＦｏｒｍＩＩ型の還元型補酵素Ｑ１０結晶又はその結晶性固体の製造方法 |
| WO2022202214A1 (ja) * | 2021-03-26 | 2022-09-29 | 株式会社カネカ | ＦｏｒｍＩＩ型の還元型補酵素Ｑ１０結晶又はその結晶性固体の製造方法 |
| US20250059124A1 (en) | 2021-12-24 | 2025-02-20 | Kaneka Corporation | Method for storing reduced coenzyme q10 |
| WO2023120555A1 (ja) | 2021-12-24 | 2023-06-29 | 株式会社カネカ | 還元型補酵素ｑ１０の保存方法 |
| WO2023176878A1 (ja) * | 2022-03-17 | 2023-09-21 | 株式会社カネカ | 還元型補酵素Ｑ１０のＦｏｒｍＩＩ型結晶を含有する固体組成物の保存方法及び前記固体組成物を含有する梱包体 |
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| US20250195434A1 (en) | 2022-03-17 | 2025-06-19 | Kaneka Corporation | Method for preserving solid composition that contains form ii type crystals of reduced coenzyme q10, and packing that contains said solid composition |
| AU2024242859A1 (en) | 2023-03-30 | 2025-11-13 | Kaneka Corporation | Crystal and preparation of reduced coenzyme q10 |
| JPWO2024204380A1 (en:Method) * | 2023-03-30 | 2024-10-03 | ||
| CN117736076B (zh) * | 2023-12-19 | 2025-07-01 | 新开利安生物科技(海南)有限公司 | 一种还原型辅酶q10晶体及其制备方法 |
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| JP4577674B2 (ja) | 2000-03-03 | 2010-11-10 | リコーエレメックス株式会社 | 商品企画開発システム、商品企画開発方法および商品企画開発プログラムを記録したコンピュータ読み取り可能な記録媒体 |
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| AU2002318846B2 (en) | 2001-07-13 | 2008-06-12 | Kaneka Corporation | Method of crystallizing reduced coenzyme Q10 from aqueous solution |
| TWI235146B (en) | 2001-07-16 | 2005-07-01 | Kaneka Corp | Method of stabilizing reduced coenzyme q10 and method of acidic crystallization |
| TWI329510B (en) | 2001-10-10 | 2010-09-01 | Kaneka Corp | Method of stabilizing reduced coenzyme q10 |
| JP4579835B2 (ja) | 2003-01-10 | 2010-11-10 | 株式会社カネカ | 還元型補酵素ｑ１０の精製方法 |
| 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 |
| AU2004278194B2 (en) * | 2003-09-10 | 2009-12-03 | Kaneka Corporation | Reduced coenzyme Q10 crystal excelling in stability and composition containing reduced coenzyme Q10 crystal |
| US20090088574A1 (en) | 2005-12-21 | 2009-04-02 | Eisai R&D Management Co., Ltd. | Crystal of 1,2-dihydropyridine compound (type iv) |
| DE102009059343A1 (de) | 2009-12-31 | 2011-07-07 | Muhr und Bender KG, 57439 | Federelement als offenes Wellenband |
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- 2012-06-21 WO PCT/JP2012/065869 patent/WO2012176842A1/ja not_active Ceased
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- 2012-06-22 TW TW101122540A patent/TWI568718B/zh active
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|---|---|
| EP2725004A4 (en) | 2014-12-03 |
| KR101991143B1 (ko) | 2019-06-19 |
| TW201311635A (zh) | 2013-03-16 |
| BR112013032641B1 (pt) | 2018-10-30 |
| CN103635452B (zh) | 2017-03-15 |
| TWI568718B (zh) | 2017-02-01 |
| ES2668675T3 (es) | 2018-05-21 |
| CN103635452A (zh) | 2014-03-12 |
| US9388109B2 (en) | 2016-07-12 |
| US9556098B2 (en) | 2017-01-31 |
| CA2837695A1 (en) | 2012-12-27 |
| EP2725004A1 (en) | 2014-04-30 |
| US20140120073A1 (en) | 2014-05-01 |
| US20160289152A1 (en) | 2016-10-06 |
| JP5998135B2 (ja) | 2016-09-28 |
| AU2012274434B2 (en) | 2016-06-09 |
| JPWO2012176842A1 (ja) | 2015-02-23 |
| BR112013032641A2 (pt) | 2017-01-24 |
| EP2725004B1 (en) | 2018-02-28 |
| KR20140061350A (ko) | 2014-05-21 |
| DK2725004T3 (en) | 2018-04-16 |
| AU2012274434A1 (en) | 2014-01-09 |
| WO2012176842A1 (ja) | 2012-12-27 |
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