ES2410357T3 - Heterociclos sustituidos con 2-metiltioetilo en calidad de aditivos para alimentos para animales - Google Patents
Heterociclos sustituidos con 2-metiltioetilo en calidad de aditivos para alimentos para animales Download PDFInfo
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- ES2410357T3 ES2410357T3 ES08865833T ES08865833T ES2410357T3 ES 2410357 T3 ES2410357 T3 ES 2410357T3 ES 08865833 T ES08865833 T ES 08865833T ES 08865833 T ES08865833 T ES 08865833T ES 2410357 T3 ES2410357 T3 ES 2410357T3
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- Prior art keywords
- compound
- acid
- methylthio
- formula
- ethyl
- Prior art date
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- 241001465754 Metazoa Species 0.000 title claims description 43
- -1 2-methylthioethyl Chemical group 0.000 title description 19
- 239000003674 animal food additive Substances 0.000 title description 5
- 125000000623 heterocyclic group Chemical group 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 47
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 claims description 36
- 238000002360 preparation method Methods 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- 241000282849 Ruminantia Species 0.000 claims description 13
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 claims description 11
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 241000251468 Actinopterygii Species 0.000 claims description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 8
- YAFPYSRADZDBFU-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)-1,3-oxazolidine-2,4-dione Chemical compound CSCCC1OC(=O)NC1=O YAFPYSRADZDBFU-UHFFFAOYSA-N 0.000 claims description 7
- 241000238424 Crustacea Species 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000002841 Lewis acid Substances 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 241000282887 Suidae Species 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 claims description 3
- 229910001623 magnesium bromide Inorganic materials 0.000 claims description 3
- 244000144977 poultry Species 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical group COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims description 2
- 229910000366 copper(II) sulfate Inorganic materials 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- ONFOSYPQQXJWGS-UHFFFAOYSA-N 2-hydroxy-4-(methylthio)butanoic acid Chemical compound CSCCC(O)C(O)=O ONFOSYPQQXJWGS-UHFFFAOYSA-N 0.000 description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 229960004452 methionine Drugs 0.000 description 34
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 33
- 229930182817 methionine Natural products 0.000 description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 239000000243 solution Substances 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- HLUFSGZOJZQPRX-UHFFFAOYSA-N 2,2-dimethyl-5-(2-methylsulfanylethyl)-1,3-dioxolan-4-one Chemical compound CSCCC1OC(C)(C)OC1=O HLUFSGZOJZQPRX-UHFFFAOYSA-N 0.000 description 17
- INTUDBWOILOBCE-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanamide Chemical compound CSCCC(O)C(N)=O INTUDBWOILOBCE-UHFFFAOYSA-N 0.000 description 17
- 210000001015 abdomen Anatomy 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- CTTWBUQGUOUQIT-UHFFFAOYSA-N 2,2-dimethyl-5-(2-methylsulfanylethyl)-1,3-oxazolidin-4-one Chemical compound CSCCC1OC(C)(C)NC1=O CTTWBUQGUOUQIT-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- YALHKEKUMDWQQW-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)-1,3-dioxolan-4-one Chemical compound CSCCC1OCOC1=O YALHKEKUMDWQQW-UHFFFAOYSA-N 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 11
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- 230000008901 benefit Effects 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- WWIXLTJRDZJIOK-UHFFFAOYSA-N 2-(2-methylsulfanylethyl)-1-oxa-4-azaspiro[4.5]decan-3-one Chemical compound N1C(=O)C(CCSC)OC11CCCCC1 WWIXLTJRDZJIOK-UHFFFAOYSA-N 0.000 description 9
- YOSPHIZGZLRVMR-UHFFFAOYSA-N 2-ethyl-2-methyl-5-(2-methylsulfanylethyl)-1,3-dioxolan-4-one Chemical compound CCC1(C)OC(CCSC)C(=O)O1 YOSPHIZGZLRVMR-UHFFFAOYSA-N 0.000 description 9
- AODCCOKATSAQOI-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)-2-phenyl-1,3-oxazolidin-4-one Chemical compound N1C(=O)C(CCSC)OC1C1=CC=CC=C1 AODCCOKATSAQOI-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- IGGRDSLFGFXYJP-UHFFFAOYSA-N 2-ethyl-2-methyl-5-(2-methylsulfanylethyl)-1,3-oxazolidin-4-one Chemical compound CCC1(C)NC(=O)C(CCSC)O1 IGGRDSLFGFXYJP-UHFFFAOYSA-N 0.000 description 8
- ZDQALIYDUIRZCA-UHFFFAOYSA-N 2-tert-butyl-5-(2-methylsulfanylethyl)-1,3-dioxolan-4-one Chemical compound CSCCC1OC(C(C)(C)C)OC1=O ZDQALIYDUIRZCA-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- OFTRFMYCRVMTMU-UHFFFAOYSA-N 5-(2-methylsulfanylethyl)-1,3-dioxolane-2,4-dione Chemical compound CSCCC1OC(=O)OC1=O OFTRFMYCRVMTMU-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- 159000000007 calcium salts Chemical class 0.000 description 6
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000011241 protective layer Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 230000004060 metabolic process Effects 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
- 239000008267 milk Substances 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- 210000000813 small intestine Anatomy 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- VWWOJJANXYSACS-UHFFFAOYSA-N 2-hydroxy-4-methylsulfanylbutanenitrile Chemical compound CSCCC(O)C#N VWWOJJANXYSACS-UHFFFAOYSA-N 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229930195722 L-methionine Natural products 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000007832 Na2SO4 Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 238000007171 acid catalysis Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 230000015556 catabolic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
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- 235000013365 dairy product Nutrition 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 2
- NDAURNKLMXSEBR-UHFFFAOYSA-N 2-hydroxy-6-methylsulfanylhexanoic acid Chemical compound CSCCCCC(O)C(O)=O NDAURNKLMXSEBR-UHFFFAOYSA-N 0.000 description 2
- DOLNLDKZJKDWLS-UHFFFAOYSA-N 2-hydroxypentanethioamide Chemical compound CCCC(O)C(N)=S DOLNLDKZJKDWLS-UHFFFAOYSA-N 0.000 description 2
- PICCHNWCTUUCAQ-UHFFFAOYSA-N 2-hydroxypentanethioic s-acid Chemical compound CCCC(O)C(O)=S PICCHNWCTUUCAQ-UHFFFAOYSA-N 0.000 description 2
- 244000144725 Amygdalus communis Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 235000003893 Prunus dulcis var amara Nutrition 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 235000010443 alginic acid Nutrition 0.000 description 2
- 229920000615 alginic acid Polymers 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
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- 235000014633 carbohydrates Nutrition 0.000 description 2
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- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- 150000002741 methionine derivatives Chemical class 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 238000009372 pisciculture Methods 0.000 description 2
- 235000013594 poultry meat Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
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- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
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- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
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- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
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- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007062199A DE102007062199A1 (de) | 2007-12-21 | 2007-12-21 | 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive |
| DE102007062199 | 2007-12-21 | ||
| PCT/EP2008/066525 WO2009080446A1 (de) | 2007-12-21 | 2008-12-01 | 2-methylthioethyl-substituierte heterocyclen als futtermitteladditive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2410357T3 true ES2410357T3 (es) | 2013-07-01 |
Family
ID=40378037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08865833T Active ES2410357T3 (es) | 2007-12-21 | 2008-12-01 | Heterociclos sustituidos con 2-metiltioetilo en calidad de aditivos para alimentos para animales |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8158186B2 (OSRAM) |
| EP (1) | EP2222654B1 (OSRAM) |
| JP (1) | JP5511679B2 (OSRAM) |
| CN (1) | CN101903363A (OSRAM) |
| AR (1) | AR069846A1 (OSRAM) |
| BR (1) | BRPI0821237A8 (OSRAM) |
| CA (1) | CA2710170C (OSRAM) |
| DE (1) | DE102007062199A1 (OSRAM) |
| ES (1) | ES2410357T3 (OSRAM) |
| RU (1) | RU2516833C2 (OSRAM) |
| WO (1) | WO2009080446A1 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007031917A1 (de) * | 2007-07-09 | 2009-01-15 | Evonik Degussa Gmbh | Verfahren zur Herstellung von Ketosäuren und deren Derivaten |
| DE102008042932A1 (de) | 2008-10-17 | 2010-04-22 | Evonik Degussa Gmbh | Herstellung und Verwendung von Methionylmethionin als Futtermitteladditiv für Fische und Krustentiere |
| DE102009002044A1 (de) * | 2009-03-31 | 2010-10-07 | Evonik Degussa Gmbh | Dipeptide als Futtermitteladditive |
| JP5355373B2 (ja) * | 2009-08-28 | 2013-11-27 | 株式会社日本触媒 | 熱可塑性樹脂組成物および光学フィルム |
| JP5914240B2 (ja) * | 2012-08-07 | 2016-05-11 | 株式会社トクヤマ | 多結晶シリコンの製造方法 |
| EP4615941A2 (en) * | 2022-11-11 | 2025-09-17 | Basf Se | Substituted 1,3-dioxolan-4-ones and 1,3-dioxan-4-ones as fragrance ingredients |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU162377B (OSRAM) * | 1970-05-27 | 1973-02-28 | ||
| JPS5249473B2 (OSRAM) * | 1972-08-09 | 1977-12-17 | ||
| DE2324591C2 (de) * | 1973-05-16 | 1985-12-12 | Basf Ag, 6700 Ludwigshafen | Oxazolidin-Derivate |
| US4524077A (en) * | 1983-11-14 | 1985-06-18 | Monsanto Company | Liquid 2-hydroxy-4-methylthiobutyric acid and process for the preparation thereof |
| SU1313410A1 (ru) * | 1985-04-02 | 1987-05-30 | Московская ветеринарная академия им.К.И.Скрябина | Способ откорма сельскохоз йственной птицы |
| GB9215665D0 (en) * | 1992-07-23 | 1992-09-09 | British Bio Technology | Compounds |
| US6017563A (en) | 1997-07-25 | 2000-01-25 | Novus International, Inc. | Process for optimizing milk production |
| FR2785773B1 (fr) * | 1998-11-13 | 2001-04-20 | Rhone Poulenc Nutrition Animal | Utilisation d'esters de methionine en nutrition animale |
| FR2791673B1 (fr) | 1999-04-02 | 2001-06-08 | Rhone Poulenc Animal Nutrition | Procede de preparation des esters de l'acide hydroxymethylthiobutyrique |
| WO2001058864A1 (en) | 2000-02-07 | 2001-08-16 | Rhone-Poulenc Animal Nutrition | Process for the preparation of 2-hydroxy-4-methylthio butyric acid esters |
| EP1358805A1 (en) | 2002-04-30 | 2003-11-05 | Aventis Animal Nutrition S.A. | Animal feed supplement |
| WO2004008874A1 (en) | 2002-07-19 | 2004-01-29 | Novus International, Inc. | Feed rations and methods of feeding growing ruminants |
| DE102006055470A1 (de) * | 2006-11-24 | 2008-05-29 | Evonik Degussa Gmbh | Ketomethioninketale und deren Derivate |
-
2007
- 2007-12-21 DE DE102007062199A patent/DE102007062199A1/de not_active Withdrawn
-
2008
- 2008-12-01 EP EP08865833A patent/EP2222654B1/de not_active Not-in-force
- 2008-12-01 JP JP2010538543A patent/JP5511679B2/ja active Active
- 2008-12-01 CN CN2008801222986A patent/CN101903363A/zh active Pending
- 2008-12-01 RU RU2010129556/04A patent/RU2516833C2/ru not_active IP Right Cessation
- 2008-12-01 CA CA2710170A patent/CA2710170C/en not_active Expired - Fee Related
- 2008-12-01 ES ES08865833T patent/ES2410357T3/es active Active
- 2008-12-01 WO PCT/EP2008/066525 patent/WO2009080446A1/de not_active Ceased
- 2008-12-01 BR BRPI0821237A patent/BRPI0821237A8/pt not_active IP Right Cessation
- 2008-12-19 AR ARP080105567A patent/AR069846A1/es unknown
- 2008-12-19 US US12/339,284 patent/US8158186B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP2222654B1 (de) | 2013-03-20 |
| JP5511679B2 (ja) | 2014-06-04 |
| US20090162474A1 (en) | 2009-06-25 |
| EP2222654A1 (de) | 2010-09-01 |
| WO2009080446A1 (de) | 2009-07-02 |
| CA2710170C (en) | 2016-03-22 |
| DE102007062199A1 (de) | 2009-06-25 |
| BRPI0821237A8 (pt) | 2016-11-08 |
| RU2010129556A (ru) | 2012-03-27 |
| JP2011509240A (ja) | 2011-03-24 |
| CN101903363A (zh) | 2010-12-01 |
| AR069846A1 (es) | 2010-02-24 |
| US8158186B2 (en) | 2012-04-17 |
| RU2516833C2 (ru) | 2014-05-20 |
| CA2710170A1 (en) | 2009-07-02 |
| BRPI0821237A2 (pt) | 2015-06-16 |
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