DE775108T1 - Wasserlösliche organische salze von kreatin - Google Patents
Wasserlösliche organische salze von kreatinInfo
- Publication number
- DE775108T1 DE775108T1 DE0775108T DE95927700T DE775108T1 DE 775108 T1 DE775108 T1 DE 775108T1 DE 0775108 T DE0775108 T DE 0775108T DE 95927700 T DE95927700 T DE 95927700T DE 775108 T1 DE775108 T1 DE 775108T1
- Authority
- DE
- Germany
- Prior art keywords
- creatine
- salts according
- anion
- acid
- water
- 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.)
- Pending
Links
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 title claims abstract 15
- 150000003839 salts Chemical class 0.000 title claims abstract 7
- 229960003624 creatine Drugs 0.000 title claims abstract 5
- 239000006046 creatine Substances 0.000 title claims abstract 5
- 235000005911 diet Nutrition 0.000 claims abstract 2
- 230000000378 dietary effect Effects 0.000 claims abstract 2
- 150000001450 anions Chemical class 0.000 claims 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 239000012141 concentrate Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000004090 dissolution Methods 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 150000003628 tricarboxylic acids Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/265—Citric acid
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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
- A23L33/17—Amino acids, peptides or proteins
- A23L33/175—Amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/04—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton
- C07C279/14—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/145—Maleic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/255—Tartaric acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Polymers & Plastics (AREA)
- Mycology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Fodder In General (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- General Preparation And Processing Of Foods (AREA)
Claims (9)
1. Salze von Kreatin mit der allgemeinen Formel I:
^C N CH7COOH A© (I)
H2N CH3
pi
worin A das Anion einer Mono-, Di- oder Tricarbonsäure darstellt.
2. Kreatinsalze nach Anspruch 1, worin A das Anion von Zitronensäure ist.
3. Kreatinsalze nach Anspruch 1, worin Aü das Anion der Maleinsäure ist.
4. Kreatinsalze nach Anspruch 1, worin Aö das Anion der Fumarsäure ist.
5. Kreatinsalze nach Anspruch 1, worin A das Anion der Weinsäure ist.
25
6. Kreatinsalze nach Anspruch 1, worin A das Anion der Apfelsäure ist.
7. Verfahren zur Herstellung der Salze nach den Ansprüchen 1-6, umfassend:
a) das gleichzeitige -Auflösen von Kreatin und der organischen Säure in
Wasser;
2 DE/ EP O 775 1 O&idigr;&iacgr; i
b) Konzentrieren der Lösung bis zur vollständigen Kristallisation und Trocknen
des erhaltenen Produkts.
8. Verfahren zur Herstellung der Salze nach Anspruch 1-6 umfassend:
5
a) die Reaktion von Kreatin mit der organischen Säure in einem mit Wasser
nicht mischbaren Lösemittel bei einer Temperatur von Raumtemperatur bis 5O0C;
b) Filtrieren und Trocknen des erhaltenen Produkts.
9. Verwendung der Salze nach den Ansprüchen 1 - 6 als Zusatz in diätetischen
Zusammensetzungen und/oder Nahrungsmittelzusammensetzungen.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ITMI941693A IT1271687B (it) | 1994-08-04 | 1994-08-04 | Sali organici idrosolubili della creatina |
PCT/EP1995/002897 WO1996004240A1 (en) | 1994-08-04 | 1995-07-21 | Hydrosoluble organic salts of creatine |
Publications (1)
Publication Number | Publication Date |
---|---|
DE775108T1 true DE775108T1 (de) | 1998-03-12 |
Family
ID=11369443
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE0775108T Pending DE775108T1 (de) | 1994-08-04 | 1995-07-21 | Wasserlösliche organische salze von kreatin |
DE69506882T Expired - Fee Related DE69506882T2 (de) | 1994-08-04 | 1995-07-21 | Wasserlösliche organische salze von kreatin |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69506882T Expired - Fee Related DE69506882T2 (de) | 1994-08-04 | 1995-07-21 | Wasserlösliche organische salze von kreatin |
Country Status (8)
Country | Link |
---|---|
US (1) | US5973199A (de) |
EP (1) | EP0775108B1 (de) |
AT (1) | ATE174905T1 (de) |
CA (1) | CA2194218C (de) |
DE (2) | DE775108T1 (de) |
ES (1) | ES2107981T1 (de) |
IT (1) | IT1271687B (de) |
WO (1) | WO1996004240A1 (de) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9611356D0 (en) * | 1996-05-31 | 1996-08-07 | Howard Alan N | Improvements in or relating to compositions containing Creatine, and other ergogenic compounds |
US8128955B2 (en) | 1996-05-31 | 2012-03-06 | The Original Creatine Patent Company | Food compositions containing creatine |
US6168802B1 (en) | 1996-05-31 | 2001-01-02 | The Howard Foundation | Compositions containing creatine and aloe vera extract |
US6274161B1 (en) | 1996-05-31 | 2001-08-14 | The Howard Foundation | Compositions containing creatine in suspension |
US7150880B2 (en) | 1996-05-31 | 2006-12-19 | The Original Creatine Patent Co. Ltd. | Compositions containing creatine and creatinine and a methyl xanthine |
US6524611B2 (en) | 1996-05-31 | 2003-02-25 | The Howard Foundation | Compositions containing creatine and creatinine |
DE19653225A1 (de) * | 1996-12-20 | 1998-06-25 | Sueddeutsche Kalkstickstoff | Kreatin-pyruvate und Verfahren zu deren Herstellung |
TR199900470T2 (xx) * | 1996-12-20 | 1999-06-21 | Skw Trostberg Aktiengesellschaft | Kreatin piruvatlar ve bunlar� �retmek i�in bir y�ntem. |
DE19707694A1 (de) * | 1997-02-26 | 1998-08-27 | Sueddeutsche Kalkstickstoff | Kreatin-ascorbate und Verfahren zu deren Herstellung |
AU6726098A (en) * | 1997-02-26 | 1998-09-18 | Skw Trostberg Aktiengesellschaft | Creatine-ascorbates, production process |
US6211407B1 (en) | 2000-05-03 | 2001-04-03 | Pfanstiehl Laboratories, Inc. | Dicreatine citrate and tricreatine citrate and method of making same |
US6399661B1 (en) * | 2000-06-26 | 2002-06-04 | Jeffrey M. Golini | Oral creatine supplement and method for making same |
DE10065478C1 (de) * | 2000-12-28 | 2002-08-29 | Sueddeutsche Kalkstickstoff | Kreatin/Citronensäure-Verbindung, Verfahren zu ihrer Herstellung und Verwendung |
US20030013767A1 (en) * | 2001-07-13 | 2003-01-16 | Samuel Bessman | Method of treating weight loss using creatine |
DE10208568A1 (de) * | 2002-02-27 | 2003-09-18 | Degussa Bioactives Deutschland | Verbindung, enthaltend Kreatin, eine Säure-Komponente und/oder einen Komplex-Bildner |
US7301051B2 (en) * | 2002-12-18 | 2007-11-27 | Starmark Laboratories | Creatine salts and method of making same |
US7109373B2 (en) * | 2002-12-18 | 2006-09-19 | San Corporation | Creatine salts and method of making same |
US6838562B2 (en) * | 2003-04-01 | 2005-01-04 | Sal Abraham | Process for preparing a creatine heterocyclic acid salt and method of use |
US20080103202A1 (en) * | 2004-11-08 | 2008-05-01 | Chris Ferguson | Method of preparing creatine ester salts and uses thereof. |
US20060194877A1 (en) * | 2005-02-07 | 2006-08-31 | Gardiner Paul T | Creatine hydroxycitric acids salts and methods for their production and use in individuals |
DK1909601T3 (da) * | 2005-08-02 | 2013-08-26 | Alzchem Ag | Flydende formulering baseret på en guanidineddikesyrekomponent |
CA2642761A1 (en) * | 2006-02-23 | 2007-08-30 | Iomedix Sleep International Srl | Compositions and methods for the induction and maintenance of quality sleep |
US7329763B1 (en) | 2006-09-11 | 2008-02-12 | New Cell Formulations Ltd | Creatine pyroglutamic acid salts and methods for their production and use in individuals |
US20080153897A1 (en) * | 2006-09-11 | 2008-06-26 | New Cell Formulations Ltd. | Creatine pyroglutamic acid salts and methods for their production and use in individuals |
WO2008031184A1 (en) * | 2006-09-11 | 2008-03-20 | New Cell Formulations Ltd. | Creatine pyroglutamic acid salts and methods for their production and use in individuals |
CA2663141C (en) * | 2006-09-11 | 2010-02-09 | New Cell Formulations Ltd. | Creatine pyroglutamic acid salts and methods for their production and use in individuals |
US20090156648A1 (en) * | 2007-12-12 | 2009-06-18 | Iovate T. & P. Inc. | Preparations containing pyridoxine and alpha-hydroxyisocaproic acid (HICA) |
US8546369B2 (en) | 2008-05-30 | 2013-10-01 | Northern Innovations Holding Corp. | Salts of creatine imino sugar amides |
US20110123654A1 (en) * | 2008-06-06 | 2011-05-26 | Ralf Jaeger | Synergistic enhancement of cellular ergogenic nutrient uptake, like creatine or carnitine, with tarragon |
US8466198B2 (en) * | 2008-09-02 | 2013-06-18 | Bruce Kneller | Compositions comprising creatine salts and methods of use thereof |
US20090312419A1 (en) * | 2009-08-12 | 2009-12-17 | Kneller Bruce W | CREATINE -ßALANINATE: A NOVEL SALT FOR INCREASING ATHLETIC PERFORMANCE |
GB201801633D0 (en) * | 2018-02-01 | 2018-03-21 | Ogorman Edward | Sports supplements based on liquid creatine |
DE102022114966A1 (de) * | 2022-06-14 | 2023-12-14 | Alzchem Trostberg Gmbh | Wasserlösliches Kreatin-Agglomerat |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1967400A (en) * | 1930-03-27 | 1934-07-24 | Schering Kahlbaum Ag | Production of guanidino fatty acids |
JPS536204A (en) * | 1976-07-08 | 1978-01-20 | Kubota Ltd | Scum removing apparatus |
DE2945790C2 (de) * | 1978-11-20 | 1987-03-12 | Tanabe Seiyaku Co., Ltd., Osaka | Neutrales L-Ornithin-L-malat-dihydrat und neutrales L-Lysin-L-malat-monohydrat und Verfahren zu deren Herstellung |
US5091171B2 (en) * | 1986-12-23 | 1997-07-15 | Tristrata Inc | Amphoteric compositions and polymeric forms of alpha hydroxyacids and their therapeutic use |
DE4123248C2 (de) * | 1991-07-13 | 1996-03-07 | Degussa | Verfahren zur Herstellung von N-substituierten alpha-Aminosäuren und alpha-Aminosäure-Derivaten |
GB9215746D0 (en) * | 1992-07-24 | 1992-09-09 | Hultman Eric | A method of increasing creatine supply depot |
JP3213666B2 (ja) * | 1994-02-28 | 2001-10-02 | 治彦 末岡 | クレアチン飲料の製造方法 |
US5627172A (en) * | 1994-03-04 | 1997-05-06 | Natural Supplement Association, Incorporated | Method for reduction of serum blood lipids or lipoprotein fraction |
US5489589A (en) * | 1994-12-07 | 1996-02-06 | Bristol-Myers Squibb Company | Amino acid derivatives of paclitaxel |
-
1994
- 1994-08-04 IT ITMI941693A patent/IT1271687B/it active IP Right Grant
-
1995
- 1995-07-21 CA CA002194218A patent/CA2194218C/en not_active Expired - Lifetime
- 1995-07-21 DE DE0775108T patent/DE775108T1/de active Pending
- 1995-07-21 US US08/649,620 patent/US5973199A/en not_active Expired - Lifetime
- 1995-07-21 WO PCT/EP1995/002897 patent/WO1996004240A1/en active IP Right Grant
- 1995-07-21 EP EP95927700A patent/EP0775108B1/de not_active Expired - Lifetime
- 1995-07-21 DE DE69506882T patent/DE69506882T2/de not_active Expired - Fee Related
- 1995-07-21 ES ES95927700T patent/ES2107981T1/es active Pending
- 1995-07-21 AT AT95927700T patent/ATE174905T1/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
IT1271687B (it) | 1997-06-04 |
DE69506882D1 (de) | 1999-02-04 |
US5973199A (en) | 1999-10-26 |
CA2194218C (en) | 1999-01-12 |
ITMI941693A1 (it) | 1996-02-04 |
WO1996004240A1 (en) | 1996-02-15 |
ES2107981T1 (es) | 1997-12-16 |
EP0775108B1 (de) | 1998-12-23 |
ATE174905T1 (de) | 1999-01-15 |
ITMI941693A0 (it) | 1994-08-04 |
EP0775108A1 (de) | 1997-05-28 |
CA2194218A1 (en) | 1996-02-15 |
DE69506882T2 (de) | 1999-05-12 |
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