CA2577437C - Acides gras a creatine - Google Patents
Acides gras a creatine Download PDFInfo
- Publication number
- CA2577437C CA2577437C CA002577437A CA2577437A CA2577437C CA 2577437 C CA2577437 C CA 2577437C CA 002577437 A CA002577437 A CA 002577437A CA 2577437 A CA2577437 A CA 2577437A CA 2577437 C CA2577437 C CA 2577437C
- Authority
- CA
- Canada
- Prior art keywords
- creatine
- acid
- fatty acid
- compound
- acetic acid
- 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.)
- Expired - Fee Related
Links
- 239000000194 fatty acid Substances 0.000 title abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 9
- 150000001336 alkenes Chemical group 0.000 claims description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 5
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 abstract description 167
- 229960003624 creatine Drugs 0.000 abstract description 77
- 239000006046 creatine Substances 0.000 abstract description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract description 57
- 150000004665 fatty acids Chemical class 0.000 abstract description 25
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 24
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 24
- 229930195729 fatty acid Natural products 0.000 abstract description 24
- 239000000203 mixture Substances 0.000 abstract description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 12
- -1 thionyl halide Chemical class 0.000 abstract description 11
- 150000001408 amides Chemical class 0.000 abstract description 8
- 230000000153 supplemental effect Effects 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 12
- 230000009469 supplementation Effects 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 10
- DRBBFCLWYRJSJZ-UHFFFAOYSA-N N-phosphocreatine Chemical compound OC(=O)CN(C)C(=N)NP(O)(O)=O DRBBFCLWYRJSJZ-UHFFFAOYSA-N 0.000 description 10
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- VKOBVWXKNCXXDE-UHFFFAOYSA-N ethyl stearic acid Natural products CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 8
- 210000003205 muscle Anatomy 0.000 description 7
- 150000004671 saturated fatty acids Chemical class 0.000 description 7
- 210000002027 skeletal muscle Anatomy 0.000 description 7
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 6
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
- 241000282414 Homo sapiens Species 0.000 description 6
- 150000001263 acyl chlorides Chemical class 0.000 description 6
- 150000001266 acyl halides Chemical class 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 229940109239 creatinine Drugs 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 6
- VZQFJZYVQNXVRY-FPLPWBNLSA-N (z)-hexadec-9-enoyl chloride Chemical compound CCCCCC\C=C/CCCCCCCC(Cl)=O VZQFJZYVQNXVRY-FPLPWBNLSA-N 0.000 description 5
- BPKZHCFXDPIIPY-UHFFFAOYSA-N 2-[(n'-dodecanoylcarbamimidoyl)-methylamino]acetic acid Chemical compound CCCCCCCCCCCC(=O)NC(=N)N(C)CC(O)=O BPKZHCFXDPIIPY-UHFFFAOYSA-N 0.000 description 5
- MEJYXFHCRXAUIL-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid;hydrate Chemical compound O.NC(=N)N(C)CC(O)=O MEJYXFHCRXAUIL-UHFFFAOYSA-N 0.000 description 5
- 235000021357 Behenic acid Nutrition 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 235000021314 Palmitic acid Nutrition 0.000 description 5
- 229940116226 behenic acid Drugs 0.000 description 5
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229960004826 creatine monohydrate Drugs 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- QTHQYNCAWSGBCE-UHFFFAOYSA-N docosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCC(Cl)=O QTHQYNCAWSGBCE-UHFFFAOYSA-N 0.000 description 5
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229960002446 octanoic acid Drugs 0.000 description 5
- VNVXHHXFIDRQDE-UHFFFAOYSA-N octanoyl bromide Chemical compound CCCCCCCC(Br)=O VNVXHHXFIDRQDE-UHFFFAOYSA-N 0.000 description 5
- 229950007002 phosphocreatine Drugs 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 150000001262 acyl bromides Chemical class 0.000 description 4
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- YRWYFHQUSMOHMG-UHFFFAOYSA-N hexadecanoyl bromide Chemical compound CCCCCCCCCCCCCCCC(Br)=O YRWYFHQUSMOHMG-UHFFFAOYSA-N 0.000 description 4
- AOHAPDDBNAPPIN-UHFFFAOYSA-N myristicinic acid Natural products COC1=CC(C(O)=O)=CC2=C1OCO2 AOHAPDDBNAPPIN-UHFFFAOYSA-N 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 4
- 210000001057 smooth muscle myoblast Anatomy 0.000 description 4
- CFNWHBTUJLORKH-UHFFFAOYSA-N 2-[(n'-hexadec-9-enoylcarbamimidoyl)-methylamino]acetic acid Chemical compound CCCCCCC=CCCCCCCCC(=O)N=C(N)N(C)CC(O)=O CFNWHBTUJLORKH-UHFFFAOYSA-N 0.000 description 3
- RMDOTNSAHHYINS-UHFFFAOYSA-N 2-[(n'-hexadecanoylcarbamimidoyl)-methylamino]acetic acid Chemical compound CCCCCCCCCCCCCCCC(=O)NC(=N)N(C)CC(O)=O RMDOTNSAHHYINS-UHFFFAOYSA-N 0.000 description 3
- ZIKAOZDEMKOWSX-UHFFFAOYSA-N 2-[methyl-(n'-octanoylcarbamimidoyl)amino]acetic acid Chemical compound CCCCCCCC(=O)NC(=N)N(C)CC(O)=O ZIKAOZDEMKOWSX-UHFFFAOYSA-N 0.000 description 3
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 3
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 235000005911 diet Nutrition 0.000 description 3
- KFEVDPWXEVUUMW-UHFFFAOYSA-N docosanoic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 KFEVDPWXEVUUMW-UHFFFAOYSA-N 0.000 description 3
- 235000004626 essential fatty acids Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 235000003441 saturated fatty acids Nutrition 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 3
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 101100180402 Caenorhabditis elegans jun-1 gene Proteins 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- 206010020880 Hypertrophy Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 235000021319 Palmitoleic acid Nutrition 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 235000021342 arachidonic acid Nutrition 0.000 description 2
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- 230000009286 beneficial effect Effects 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 2
- 229940090949 docosahexaenoic acid Drugs 0.000 description 2
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 2
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 2
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
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- 230000007246 mechanism Effects 0.000 description 2
- 230000037257 muscle growth Effects 0.000 description 2
- 230000003387 muscular Effects 0.000 description 2
- 210000001087 myotubule Anatomy 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
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- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- PXQPEWDEAKTCGB-UHFFFAOYSA-N orotic acid Chemical compound OC(=O)C1=CC(=O)NC(=O)N1 PXQPEWDEAKTCGB-UHFFFAOYSA-N 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 125000005471 saturated fatty acid group Chemical group 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 210000000130 stem cell Anatomy 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SJRRNWROGBKTKI-UHFFFAOYSA-N 2-[(n'-butanoylcarbamimidoyl)-methylamino]acetic acid Chemical compound CCCC(=O)NC(=N)N(C)CC(O)=O SJRRNWROGBKTKI-UHFFFAOYSA-N 0.000 description 1
- UYCYMUFPAYUXTI-UHFFFAOYSA-N 2-[(n'-decanoylcarbamimidoyl)-methylamino]acetic acid Chemical compound CCCCCCCCCC(=O)NC(=N)N(C)CC(O)=O UYCYMUFPAYUXTI-UHFFFAOYSA-N 0.000 description 1
- SICSYBKLVBIEDN-UHFFFAOYSA-N 2-[(n'-docos-13-enoylcarbamimidoyl)-methylamino]acetic acid Chemical compound CCCCCCCCC=CCCCCCCCCCCCC(=O)N=C(N)N(C)CC(O)=O SICSYBKLVBIEDN-UHFFFAOYSA-N 0.000 description 1
- KANZCRXSGHQJCI-UHFFFAOYSA-N 2-[(n'-docosanoylcarbamimidoyl)-methylamino]acetic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)NC(=N)N(C)CC(O)=O KANZCRXSGHQJCI-UHFFFAOYSA-N 0.000 description 1
- CEUMCMQMEJMRRC-UHFFFAOYSA-N 2-[(n'-hexanoylcarbamimidoyl)-methylamino]acetic acid Chemical compound CCCCCC(=O)NC(=N)N(C)CC(O)=O CEUMCMQMEJMRRC-UHFFFAOYSA-N 0.000 description 1
- MBCIKFWLYBALHF-UHFFFAOYSA-N 2-[(n'-icosanoylcarbamimidoyl)-methylamino]acetic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)NC(=N)N(C)CC(O)=O MBCIKFWLYBALHF-UHFFFAOYSA-N 0.000 description 1
- XXROLXMSJKODMC-JDPCYWKWSA-N 2-[[n'-[(4z,7z,10z,13z,16z,19z)-docosa-4,7,10,13,16,19-hexaenoyl]carbamimidoyl]-methylamino]acetic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NC(=N)N(C)CC(O)=O XXROLXMSJKODMC-JDPCYWKWSA-N 0.000 description 1
- DLNGCCQFGNSBOP-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid;2-oxopropanoic acid Chemical class CC(=O)C(O)=O.NC(=N)N(C)CC(O)=O DLNGCCQFGNSBOP-UHFFFAOYSA-N 0.000 description 1
- NCHTYQALNFERNI-UHFFFAOYSA-N 2-[methyl-(n'-octadecanoylcarbamimidoyl)amino]acetic acid Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC(=N)N(C)CC(O)=O NCHTYQALNFERNI-UHFFFAOYSA-N 0.000 description 1
- RDTRROBYZWHAEX-JPFHKJGASA-N 2-[methyl-[n'-[(6z,9z,12z)-octadeca-6,9,12-trienoyl]carbamimidoyl]amino]acetic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)NC(=N)N(C)CC(O)=O RDTRROBYZWHAEX-JPFHKJGASA-N 0.000 description 1
- GPQCJHBOSRSHSX-NQLNTKRDSA-N 2-[methyl-[n'-[(9z,12z)-octadeca-9,12-dienoyl]carbamimidoyl]amino]acetic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)NC(=N)N(C)CC(O)=O GPQCJHBOSRSHSX-NQLNTKRDSA-N 0.000 description 1
- PUVYVWJYQWUGNE-KHPPLWFESA-N 2-[methyl-[n'-[(z)-octadec-9-enoyl]carbamimidoyl]amino]acetic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NC(=N)N(C)CC(O)=O PUVYVWJYQWUGNE-KHPPLWFESA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028311 Muscle hypertrophy Diseases 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
- 208000026214 Skeletal muscle atrophy Diseases 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001345 alkine derivatives Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000030609 dephosphorylation Effects 0.000 description 1
- 238000006209 dephosphorylation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- UFIVEPVSAGBUSI-UHFFFAOYSA-N dihydroorotic acid Chemical class OC(=O)C1CC(=O)NC(=O)N1 UFIVEPVSAGBUSI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000002270 ergogenic effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- 230000012042 muscle hypertrophy Effects 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 229960005010 orotic acid Drugs 0.000 description 1
- 235000019629 palatability Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 229940076788 pyruvate Drugs 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000025185 skeletal muscle atrophy Effects 0.000 description 1
- 230000025175 skeletal muscle hypertrophy Effects 0.000 description 1
- 210000000419 skeletal muscle satellite cell Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 125000005314 unsaturated fatty acid group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/22—Y being a hydrogen or a carbon atom, e.g. benzoylguanidines
-
- 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
La présente invention décrit des composés produits à partir d'une molécule de créatine et d'une molécule d'acide gras. Les composés se présentent sous la forme d'associations créatine-acide gras reliées par une liaison amide, ou sous la forme de mélanges de tels composés obtenus en faisant réagir de la créatine ou des dérivés de la créatine avec un acide gras approprié en présence de dichlorométhane et de pyridine, un catalyseur, que l'on a auparavant fait réagir avec un halogénure de thionyle. L'administration de telles molécules fournit une quantité supplémentaire de créatine, en accroît la biodisponibilité, et confère les avantages inhérents à l'acide gras utilisé.
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002577437A CA2577437C (fr) | 2007-02-20 | 2007-02-20 | Acides gras a creatine |
CA 2622478 CA2622478A1 (fr) | 2007-02-20 | 2008-02-20 | Composes a base de creatine et d'acides gras |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002577437A CA2577437C (fr) | 2007-02-20 | 2007-02-20 | Acides gras a creatine |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2577437A1 CA2577437A1 (fr) | 2007-05-21 |
CA2577437C true CA2577437C (fr) | 2008-02-12 |
Family
ID=38066769
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002577437A Expired - Fee Related CA2577437C (fr) | 2007-02-20 | 2007-02-20 | Acides gras a creatine |
Country Status (1)
Country | Link |
---|---|
CA (1) | CA2577437C (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2007362563A1 (en) * | 2007-12-18 | 2009-06-25 | Northern Innovations And Formulations Corp. | Creatinol-fatty acid esters |
-
2007
- 2007-02-20 CA CA002577437A patent/CA2577437C/fr not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CA2577437A1 (fr) | 2007-05-21 |
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Legal Events
Date | Code | Title | Description |
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EEER | Examination request | ||
MKLA | Lapsed |
Effective date: 20220221 |
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MKLA | Lapsed |
Effective date: 20220221 |