CA2363680A1 - Sels de choline emettant peu d'odeurs - Google Patents
Sels de choline emettant peu d'odeurs Download PDFInfo
- Publication number
- CA2363680A1 CA2363680A1 CA002363680A CA2363680A CA2363680A1 CA 2363680 A1 CA2363680 A1 CA 2363680A1 CA 002363680 A CA002363680 A CA 002363680A CA 2363680 A CA2363680 A CA 2363680A CA 2363680 A1 CA2363680 A1 CA 2363680A1
- Authority
- CA
- Canada
- Prior art keywords
- choline
- choline salt
- tma
- salt
- odor
- 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.)
- Abandoned
Links
- 239000004381 Choline salt Substances 0.000 title claims abstract description 50
- 235000019417 choline salt Nutrition 0.000 title claims abstract description 49
- 150000003248 quinolines Chemical class 0.000 title claims abstract description 47
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 87
- 229960004874 choline bitartrate Drugs 0.000 claims description 13
- QWJSAWXRUVVRLH-UHFFFAOYSA-M choline bitartrate Chemical compound C[N+](C)(C)CCO.OC(=O)C(O)C(O)C([O-])=O QWJSAWXRUVVRLH-UHFFFAOYSA-M 0.000 claims description 13
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 6
- KZSXRDLXTFEHJM-UHFFFAOYSA-N 5-(trifluoromethyl)benzene-1,3-diamine Chemical compound NC1=CC(N)=CC(C(F)(F)F)=C1 KZSXRDLXTFEHJM-UHFFFAOYSA-N 0.000 claims description 6
- 235000019743 Choline chloride Nutrition 0.000 claims description 6
- 229960003178 choline chloride Drugs 0.000 claims description 6
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 6
- 239000004615 ingredient Substances 0.000 claims description 5
- 239000000047 product Substances 0.000 description 21
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical class C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 16
- 229960001231 choline Drugs 0.000 description 14
- 150000001412 amines Chemical class 0.000 description 9
- 238000000746 purification Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- -1 phosphatidylcholine Chemical class 0.000 description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 241000282412 Homo Species 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 235000002906 tartaric acid Nutrition 0.000 description 4
- 239000011975 tartaric acid Substances 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229940075419 choline hydroxide Drugs 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 150000003956 methylamines Chemical class 0.000 description 2
- 235000019629 palatability Nutrition 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- HVAUUPRFYPCOCA-AREMUKBSSA-N 2-O-acetyl-1-O-hexadecyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCOC[C@@H](OC(C)=O)COP([O-])(=O)OCC[N+](C)(C)C HVAUUPRFYPCOCA-AREMUKBSSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- 208000035985 Body Odor Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 108010003541 Platelet Activating Factor Proteins 0.000 description 1
- 206010040904 Skin odour abnormal Diseases 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 235000019728 animal nutrition Nutrition 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000020774 essential nutrients Nutrition 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 230000002440 hepatic effect Effects 0.000 description 1
- 235000006486 human diet Nutrition 0.000 description 1
- 230000004068 intracellular signaling Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 230000003212 lipotrophic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 230000005055 memory storage Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- ZMQNTPHELNFTRE-UHFFFAOYSA-N n,n-dimethylmethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound CN(C)C.OC(=O)CC(O)(C(O)=O)CC(O)=O ZMQNTPHELNFTRE-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 230000009131 signaling function Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- KYWVDGFGRYJLPE-UHFFFAOYSA-N trimethylazanium;acetate Chemical compound CN(C)C.CC(O)=O KYWVDGFGRYJLPE-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
La présente invention concerne un sel de choline émettant peu d'odeurs purifié jusqu'à ce que la concentration d'équilibre du triméthylamine dans l'atmosphère au-dessus du sel de choline soit inférieure à 0,2 parties par milliards.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12067099P | 1999-02-19 | 1999-02-19 | |
| US60/120,670 | 1999-02-19 | ||
| US50597000A | 2000-02-17 | 2000-02-17 | |
| PCT/US2000/004016 WO2000048986A2 (fr) | 1999-02-19 | 2000-02-17 | Sels de choline emettant peu d'odeurs |
| US09/505,970 | 2000-02-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2363680A1 true CA2363680A1 (fr) | 2000-08-24 |
Family
ID=26818627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002363680A Abandoned CA2363680A1 (fr) | 1999-02-19 | 2000-02-17 | Sels de choline emettant peu d'odeurs |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2002537281A (fr) |
| BR (1) | BR0008337A (fr) |
| CA (1) | CA2363680A1 (fr) |
| MX (1) | MXPA01008354A (fr) |
| WO (1) | WO2000048986A2 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108707082A (zh) * | 2018-07-10 | 2018-10-26 | 天津辰力工程设计有限公司 | 一种酒石酸氢胆碱制备方法 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8992898B2 (en) | 2010-04-17 | 2015-03-31 | Shannon Elizabeth Klingman | Antiperspirants and deodorants |
| WO2018002888A1 (fr) | 2016-06-29 | 2018-01-04 | Halo Life Science, Llc | Procédés de fabrication de sels de choline à faible odeur d'un composé organique |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1172920A1 (ru) * | 1983-02-15 | 1985-08-15 | Институт технической теплофизики АН УССР | Способ получени сыпучей формы порошкообразного холинхлорида |
| RO93559B1 (ro) * | 1986-03-29 | 1988-01-31 | îNTREPRINDEREA DE MEDICAMENTE "SINTOFARM" | Procedeu de obtinere a bitartratului de colina |
| RO111761B1 (ro) * | 1994-08-09 | 1997-01-30 | Sc Sicomed Sa | Procedeu de obținere a bitartratului de colină |
| JP3478893B2 (ja) * | 1995-02-10 | 2003-12-15 | 日本ヒドラジン工業株式会社 | 高純度コリンの製造方法 |
| JPH1150286A (ja) * | 1997-08-05 | 1999-02-23 | Nippon Hidorajin Kogyo Kk | 高純度有機カルボン酸・コリン塩及び高純度コリンの製造方法 |
-
2000
- 2000-02-17 JP JP2000599727A patent/JP2002537281A/ja active Pending
- 2000-02-17 MX MXPA01008354A patent/MXPA01008354A/es unknown
- 2000-02-17 CA CA002363680A patent/CA2363680A1/fr not_active Abandoned
- 2000-02-17 BR BR0008337-2A patent/BR0008337A/pt not_active IP Right Cessation
- 2000-02-17 WO PCT/US2000/004016 patent/WO2000048986A2/fr not_active Ceased
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108707082A (zh) * | 2018-07-10 | 2018-10-26 | 天津辰力工程设计有限公司 | 一种酒石酸氢胆碱制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002537281A (ja) | 2002-11-05 |
| WO2000048986A2 (fr) | 2000-08-24 |
| MXPA01008354A (es) | 2003-06-06 |
| WO2000048986A8 (fr) | 2001-04-05 |
| BR0008337A (pt) | 2002-02-26 |
| WO2000048986A3 (fr) | 2000-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |