CA2905225C - Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate - Google Patents
Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate Download PDFInfo
- Publication number
- CA2905225C CA2905225C CA2905225A CA2905225A CA2905225C CA 2905225 C CA2905225 C CA 2905225C CA 2905225 A CA2905225 A CA 2905225A CA 2905225 A CA2905225 A CA 2905225A CA 2905225 C CA2905225 C CA 2905225C
- Authority
- CA
- Canada
- Prior art keywords
- hydroxybutyrate
- alcohol
- poly
- process according
- hydroxybutyl
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/18—Polyhydroxylic acyclic alcohols
- C07C31/20—Dihydroxylic alcohols
- C07C31/207—1,4-Butanediol; 1,3-Butanediol; 1,2-Butanediol; 2,3-Butanediol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/02—Preparation of carboxylic acid esters by interreacting ester groups, i.e. transesterification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/675—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids of saturated hydroxy-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/62—Carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361783167P | 2013-03-14 | 2013-03-14 | |
| US61/783,167 | 2013-03-14 | ||
| PCT/EP2014/055156 WO2014140308A1 (en) | 2013-03-14 | 2014-03-14 | Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2905225A1 CA2905225A1 (en) | 2014-09-18 |
| CA2905225C true CA2905225C (en) | 2021-05-04 |
Family
ID=50336299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2905225A Active CA2905225C (en) | 2013-03-14 | 2014-03-14 | Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US11566268B2 (https=) |
| EP (1) | EP2984066B1 (https=) |
| JP (1) | JP6110959B2 (https=) |
| KR (1) | KR102265842B1 (https=) |
| CN (1) | CN105246870A (https=) |
| AU (1) | AU2014230120B2 (https=) |
| BR (1) | BR112015023334B1 (https=) |
| CA (1) | CA2905225C (https=) |
| DK (1) | DK2984066T3 (https=) |
| ES (1) | ES2623368T3 (https=) |
| GB (1) | GB2515603B (https=) |
| SG (1) | SG11201507685UA (https=) |
| WO (1) | WO2014140308A1 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1648952B1 (en) | 2003-06-03 | 2018-03-07 | THE UNITED STATES GOVERNMENT as represented by THE DEPARTMENT OF HEALTH AND HUMAN SERVICES | Nutritional supplements and therapeutic compositions comprising (r)-3-hydroxybutyrate derivatives |
| EP2240017B1 (en) | 2008-01-04 | 2019-03-13 | Oxford University Innovation Limited | Ketone bodies and ketone body esters as blood lipid lowering agents |
| US8642654B2 (en) | 2009-04-16 | 2014-02-04 | Isis Innovation Limited | Hydroxybutyrate ester and medical use thereof |
| GB201002983D0 (en) | 2010-02-22 | 2010-04-07 | Tdeltas Ltd | Nutritinal composition |
| DK2914251T3 (da) | 2012-11-05 | 2019-11-04 | Us Health | Ketonlegemer til beskyttelse af væv mod beskadigelse som følge af ioniseringsstråling |
| GB201304467D0 (en) | 2013-03-12 | 2013-04-24 | Tdeltas Ltd | Compound for use in protecting skin |
| GB2515603B (en) | 2013-03-14 | 2015-10-14 | Isis Innovation | Process for producing (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate |
| US9249378B2 (en) | 2013-08-02 | 2016-02-02 | Eastman Chemical Company | Aqueous cleaning compositions having enhanced properties |
| US9388114B2 (en) | 2013-08-02 | 2016-07-12 | Eastman Chemical Company | Compositions including an alkyl 3-hydroxybutyrate |
| US9255059B2 (en) | 2013-08-02 | 2016-02-09 | Eastman Chemical Company | Method for producing an alkyl 3-hydroxybutyrate |
| US9163202B2 (en) | 2013-08-02 | 2015-10-20 | Eastman Chemical Company | Aqueous cleaning compositions including an alkyl 3-hydroxybutyrate |
| EP3400100B1 (en) * | 2016-01-06 | 2020-09-23 | Archer Daniels Midland Company | Process for producing 1,3-butanediol and for optionally further producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate |
| WO2017213999A1 (en) | 2016-06-07 | 2017-12-14 | The J. David Gladstone Institutes | Medium chain fatty acid esters of beta-hydroxybutyrate and butanediol and compositions and methods for using same |
| US20180057846A1 (en) | 2016-08-30 | 2018-03-01 | KetoneAid Inc. | Partially buffered free acid and/or ketone blend for rapid onset ketosis and metabolic therapy |
| GB201710229D0 (en) | 2017-06-27 | 2017-08-09 | Tdeltas Ltd | Compounds for new use |
| WO2019018683A1 (en) | 2017-07-21 | 2019-01-24 | Buck Institute For Research On Aging | BETA-HYDROXYBUTYRATE AND BUTANEDIOL ENANTIOMERS AND METHODS OF USE THEREOF |
| US11760963B2 (en) | 2017-08-23 | 2023-09-19 | KetoneAid Inc. | Ketogenic beer and alcoholic beverage mixture containing non-racemic ethyl 3-hydroxybutyrate and/or 1,3 butanediol |
| GB201715654D0 (en) | 2017-09-27 | 2017-11-08 | Tdeltas Ltd | Method of treatment |
| JP7039940B2 (ja) * | 2017-11-09 | 2022-03-23 | トヨタ自動車株式会社 | 車両制御装置 |
| WO2019147503A1 (en) * | 2018-01-25 | 2019-08-01 | Buck Institute For Research On Aging | Synthesis of 3-hydroxybutyryl 3-hydroxybutyrate and related compounds |
| GB2575623B (en) | 2018-06-04 | 2022-10-26 | Tdeltas Ltd | 3-hydroxybutyrate esters for treating cancer cachexia |
| GB2577723A (en) | 2018-10-04 | 2020-04-08 | Tdeltas Ltd | Compounds for new use |
| EP3880649B1 (de) * | 2019-01-17 | 2023-03-15 | KetoLipix Therapeutics GmbH | Verfahren zur herstellung von polyolbasierten estern von hydroxycarbonsäuren |
| GB201918657D0 (en) | 2019-12-17 | 2020-01-29 | Tdeltas Ltd | Compounds for new use |
| US12396974B2 (en) | 2020-03-27 | 2025-08-26 | KetoneAid | Ketone ester as a therapeutic treatment of Covid-19 and related viral infections |
| CN113045416B (zh) * | 2021-03-23 | 2023-08-18 | 南京纽邦生物科技有限公司 | 一种(r)-3-羟基丁酰-(r)-3-羟基丁酯的制备方法 |
| EP4363599A1 (en) | 2021-06-28 | 2024-05-08 | PHB Industrial S.A. | Methods to produce therapeutic formulations comprising hydroxybutirate and hydroxyvalerate, therapeutic formulations and uses thereof |
| WO2025143117A1 (ja) * | 2023-12-28 | 2025-07-03 | 株式会社カネカ | バイオマス由来ヒドロキシアルカン酸エステルの製造方法 |
| CN119019245A (zh) * | 2024-08-16 | 2024-11-26 | 上海康鑫化工有限公司 | 医药级3-羟基丁酸钠的制备方法 |
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| US9895331B2 (en) | 2012-07-23 | 2018-02-20 | The University Of Tokyo | Prophylactic and/or therapeutic agent for radiation damage |
| DK2914251T3 (da) | 2012-11-05 | 2019-11-04 | Us Health | Ketonlegemer til beskyttelse af væv mod beskadigelse som følge af ioniseringsstråling |
| GB201304467D0 (en) * | 2013-03-12 | 2013-04-24 | Tdeltas Ltd | Compound for use in protecting skin |
| GB2515603B (en) | 2013-03-14 | 2015-10-14 | Isis Innovation | Process for producing (R)-3-Hydroxybutyl (R)-3-Hydroxybutyrate |
| CA2902603C (en) | 2013-03-19 | 2021-03-02 | University Of South Florida | Compositions and methods for producing elevated and sustained ketosis |
| GB201314127D0 (en) | 2013-08-07 | 2013-09-18 | Tdeltas Ltd | Ketone body and ketone body ester for reducing muscle breakdown |
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|---|---|
| ES2623368T3 (es) | 2017-07-11 |
| JP6110959B2 (ja) | 2017-04-05 |
| US20140308719A1 (en) | 2014-10-16 |
| HK1205100A1 (zh) | 2015-12-11 |
| US20230295672A1 (en) | 2023-09-21 |
| DK2984066T3 (en) | 2017-05-08 |
| GB201404577D0 (en) | 2014-04-30 |
| SG11201507685UA (en) | 2015-10-29 |
| BR112015023334A2 (pt) | 2017-07-18 |
| CA2905225A1 (en) | 2014-09-18 |
| EP2984066B1 (en) | 2017-02-01 |
| GB2515603B (en) | 2015-10-14 |
| BR112015023334B1 (pt) | 2021-05-18 |
| EP2984066A1 (en) | 2016-02-17 |
| CN105246870A (zh) | 2016-01-13 |
| AU2014230120A1 (en) | 2015-10-08 |
| JP2016511278A (ja) | 2016-04-14 |
| US11566268B2 (en) | 2023-01-31 |
| WO2014140308A1 (en) | 2014-09-18 |
| AU2014230120B2 (en) | 2018-06-21 |
| KR102265842B1 (ko) | 2021-06-15 |
| GB2515603A (en) | 2014-12-31 |
| KR20160005687A (ko) | 2016-01-15 |
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