JP5306321B2 - 反芻動物用餌補完用組成物及び反芻動物餌補完方法 - Google Patents
反芻動物用餌補完用組成物及び反芻動物餌補完方法 Download PDFInfo
- Publication number
- JP5306321B2 JP5306321B2 JP2010503097A JP2010503097A JP5306321B2 JP 5306321 B2 JP5306321 B2 JP 5306321B2 JP 2010503097 A JP2010503097 A JP 2010503097A JP 2010503097 A JP2010503097 A JP 2010503097A JP 5306321 B2 JP5306321 B2 JP 5306321B2
- Authority
- JP
- Japan
- Prior art keywords
- supplement
- essential amino
- rumen
- lysine
- amino 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 28
- 241000282849 Ruminantia Species 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 12
- 239000013589 supplement Substances 0.000 title claims description 11
- 239000003797 essential amino acid Substances 0.000 claims description 44
- 235000020776 essential amino acid Nutrition 0.000 claims description 44
- 210000004767 rumen Anatomy 0.000 claims description 44
- 239000004472 Lysine Substances 0.000 claims description 37
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 31
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 30
- 241001465754 Metazoa Species 0.000 claims description 25
- 150000001413 amino acids Chemical class 0.000 claims description 24
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical group CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims description 21
- 229930182817 methionine Chemical group 0.000 claims description 21
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 18
- 150000002466 imines Chemical class 0.000 claims description 17
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims description 10
- 235000013305 food Nutrition 0.000 claims description 9
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 9
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 6
- 235000005822 corn Nutrition 0.000 claims description 6
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 5
- 238000000855 fermentation Methods 0.000 claims description 5
- 230000004151 fermentation Effects 0.000 claims description 5
- 235000013339 cereals Nutrition 0.000 claims description 4
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims description 4
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 4
- 235000015872 dietary supplement Nutrition 0.000 claims description 4
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 4
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000005862 Whey Substances 0.000 claims description 3
- 102000007544 Whey Proteins Human genes 0.000 claims description 3
- 108010046377 Whey Proteins Proteins 0.000 claims description 3
- 239000012876 carrier material Substances 0.000 claims description 3
- 235000005911 diet Nutrition 0.000 claims description 3
- 239000000796 flavoring agent Substances 0.000 claims description 3
- 235000013312 flour Nutrition 0.000 claims description 3
- 235000013355 food flavoring agent Nutrition 0.000 claims description 3
- 230000037213 diet Effects 0.000 claims description 2
- 230000001502 supplementing effect Effects 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims 5
- 230000003000 nontoxic effect Effects 0.000 claims 5
- 241000209149 Zea Species 0.000 claims 2
- 239000006052 feed supplement Substances 0.000 claims 2
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 229960003646 lysine Drugs 0.000 description 35
- 229940024606 amino acid Drugs 0.000 description 22
- 235000001014 amino acid Nutrition 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229960002885 histidine Drugs 0.000 description 12
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 12
- 235000018102 proteins Nutrition 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 210000000936 intestine Anatomy 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 241000283690 Bos taurus Species 0.000 description 8
- 239000002262 Schiff base Substances 0.000 description 8
- 150000004753 Schiff bases Chemical class 0.000 description 8
- 235000013336 milk Nutrition 0.000 description 8
- 239000008267 milk Substances 0.000 description 8
- 210000004080 milk Anatomy 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 7
- 229960005337 lysine hydrochloride Drugs 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 244000005700 microbiome Species 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 5
- 239000003925 fat Substances 0.000 description 5
- -1 histidine imines Chemical class 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229960004452 methionine Drugs 0.000 description 5
- 230000000813 microbial effect Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000009469 supplementation Effects 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 230000000968 intestinal effect Effects 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 235000013365 dairy product Nutrition 0.000 description 3
- 230000029087 digestion Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 102000014171 Milk Proteins Human genes 0.000 description 2
- 108010011756 Milk Proteins Proteins 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000001055 chewing effect Effects 0.000 description 2
- 235000020940 control diet Nutrition 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000002183 duodenal effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 235000021243 milk fat Nutrition 0.000 description 2
- 235000021239 milk protein Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 2
- QZNNVYOVQUKYSC-JEDNCBNOSA-N (2s)-2-amino-3-(1h-imidazol-5-yl)propanoic acid;hydron;chloride Chemical compound Cl.OC(=O)[C@@H](N)CC1=CN=CN1 QZNNVYOVQUKYSC-JEDNCBNOSA-N 0.000 description 1
- CMXXUDSWGMGYLZ-XRIGFGBMSA-N (2s)-2-amino-3-(1h-imidazol-5-yl)propanoic acid;hydron;chloride;hydrate Chemical compound O.Cl.OC(=O)[C@@H](N)CC1=CN=CN1 CMXXUDSWGMGYLZ-XRIGFGBMSA-N 0.000 description 1
- YHOXMLBMBQHBKB-UHFFFAOYSA-N 2-amino-6-(octylideneamino)hexanoic acid Chemical compound CCCCCCCC=NCCCCC(N)C(O)=O YHOXMLBMBQHBKB-UHFFFAOYSA-N 0.000 description 1
- SQYAVWYBXVNUNZ-UHFFFAOYSA-N 2-amino-6-[(4-methoxyphenyl)methylideneamino]hexanoic acid Chemical compound COC1=CC=C(C=NCCCCC(N)C(O)=O)C=C1 SQYAVWYBXVNUNZ-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- HKXLAGBDJVHRQG-YFKPBYRVSA-N L-lysinamide Chemical class NCCCC[C@H](N)C(N)=O HKXLAGBDJVHRQG-YFKPBYRVSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 108010039491 Ricin Proteins 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000003935 benzaldehydes Chemical class 0.000 description 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229960003882 histidine monohydrochloride monohydrate Drugs 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 150000002668 lysine derivatives Chemical class 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 235000019624 protein content Nutrition 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229960002898 threonine Drugs 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/142—Amino acids; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/10—Feeding-stuffs specially adapted for particular animals for ruminants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Birds (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Nutrition Science (AREA)
- Fodder In General (AREA)
- Feed For Specific Animals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
リシンハイドロクロライド(4.8g、26.3ミリモル)を35mLの水に溶解した。NaOH(1g、26.3ミリモル)を前記溶解液に添加し、アイスバスで冷却した。この混合物に、ベンズアルデヒド(2.8g、26.3ミリモル)を添加し、約10分掛けて生成物を沈殿させた。混合物を濾過し、水洗した。得られた固体を乾燥し、約5.2gの白色固体を得た。
リシンハイドロクロライド(4.2g、23ミリモル)を30mLの水に溶解した。NaOH(0.91g、23ミリモル)を前記溶解液に添加し、アイスバスで冷却した。この混合物に、トランスーシンナムアルデヒド(3.0g、23ミリモル)を添加し、約10分掛けて生成物を沈殿させた。混合物を濾過し、水洗した。得られた固体を乾燥し、約4.9gの固体を得た。
リシンハイドロクロライド(2.2g、12ミリモル)を25mLの水に溶解した。NaOH(0.48g、12ミリモル)を前記溶解液に添加し、アイスバスで冷却した。この混合物に、4−メトキシベンズアルデヒド(1.6g、12ミリモル)を添加し、約10分掛けて生成物を沈殿させた。混合物を濾過し、水洗した。得られた固体を乾燥し、約2.6gの固体を得た。
リシンハイドロクロライド(2.7g、14.8ミリモル)を100mLの水に溶解した。NaOH(0.59g、14.8ミリモル)を前記溶解液に添加し、アイスバスで冷却した。この混合物に、オクチルアルデヒド(1.9g、14.8ミリモル)を添加し、約10分掛けて生成物を沈殿させた。沈殿物は、オイル状に凝集した。溶媒をデカントし、オイル状沈殿物を減圧乾燥した。オイル状物質2.5gが得られた。
処理期間:14日間
処理:1)コントロール
2)コントロール+N−ベンジリデンーL−リシンからのリシン40g
全ての牛に同じ基本量の餌を与えた。牛は2つの処理グループのいずれかに振り分けた。(1)コントロール及び(2)コントロール+N−ベンジリデンーL−リシン(TrTA)。牛が1日に53.0ポンドの乾燥物質を消費するごとに、40gのリシンを補給できるように、N−ベンジリデンーL−リシンを与えた。コントロールの餌ではリシンが不足した。コントロールの餌及びN−ベンジリデンーL−リシンを補給した餌の授乳に対する応答を表1に示す。「P」は確率値(P値)を示す。
メチオニン(2.2g、14.7ミリモル)を100mLのMeOHに溶解した。NaOH(0.59g、14.7ミリモル)を前記液に添加し、全てが溶解するまで攪拌した。これに、ベンズアルデヒド(1.9g、17.9ミリモル)を添加し、この混合物を約10分攪拌した。この混合物を減圧濃縮し、残渣をEtOHに添加した。この溶液から生成物を結晶化させた。これを乾燥して約1.5gの固体を得た。生成物は白色固体で、窒素の含有量を分析し、理論値と比較した。理論値は、窒素5.9%で、実測値は窒素5.9%であった。
ヒスチジンモノハイドロクロライド一水和物(5.3g、25.3ミリモル)を100mLのMeOHに溶解した。NaOH(2.0g、50ミリモル)を前記液に添加し、攪拌した。ヒスチジンは完全には溶解しなかったので、全てが溶解するまで水を加えた。この混合物に、ベンズアルデヒド(2.6g、25ミリモル)を添加し、この混合物を約10分攪拌した。この混合物を減圧濃縮し、残渣をEtOHに添加した。生成物を濾過し、EtOHで洗浄した。これを乾燥して約3.7gの白色固体を得た。
Claims (8)
- 前記非毒性のキャリアが、香味料である請求項1に記載した組成物。
- 前記非毒性のキャリアが、糖、発酵可溶分、供給穀物、軸付きとうもろこしの粉、乳清及び他のセルロース性キャリア物質から成る群から選択される請求項1又は2に記載した組成物。
- 前記餌補完として効果的な量が、1動物1日に、1gから50gのアミノ酸を補給するために十分な量である請求項1〜3のいずれか1項に記載した組成物。
- 前記必須アミノ酸のイミン誘導体を、香味料である非毒性のキャリアと混合することを更に含む請求項5に記載した方法。
- 前記非毒性のキャリアが、糖、発酵可溶分、供給穀物、軸付きとうもろこしの粉、乳清及び他のセルロース性キャリア物質から成る群から選択される請求項6に記載した方法。
- 前記餌補完として効果的な量が、1動物1日に、1gから50gのアミノ酸を補給するために十分な量である請求項5〜7のいずれか1項に記載した方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/734,028 | 2007-04-11 | ||
US11/734,028 US7704521B2 (en) | 2007-04-11 | 2007-04-11 | Rumen protected essential amino acids |
PCT/US2008/052607 WO2008127759A1 (en) | 2007-04-11 | 2008-01-31 | Rumen protected essential amino acids |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010523686A JP2010523686A (ja) | 2010-07-15 |
JP2010523686A5 JP2010523686A5 (ja) | 2013-02-14 |
JP5306321B2 true JP5306321B2 (ja) | 2013-10-02 |
Family
ID=39399318
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010503097A Active JP5306321B2 (ja) | 2007-04-11 | 2008-01-31 | 反芻動物用餌補完用組成物及び反芻動物餌補完方法 |
Country Status (9)
Country | Link |
---|---|
US (2) | US7704521B2 (ja) |
EP (1) | EP2131671A1 (ja) |
JP (1) | JP5306321B2 (ja) |
AR (1) | AR065561A1 (ja) |
CA (1) | CA2684427C (ja) |
CL (1) | CL2008000520A1 (ja) |
DE (1) | DE112008000811B4 (ja) |
MX (1) | MX2009010453A (ja) |
WO (1) | WO2008127759A1 (ja) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080255234A1 (en) * | 2007-04-11 | 2008-10-16 | Zinpro Corporation | Rumen protected lysine |
US7704521B2 (en) * | 2007-04-11 | 2010-04-27 | Zinpro Corporation | Rumen protected essential amino acids |
US9149057B2 (en) | 2011-03-01 | 2015-10-06 | Zinpro Corporation | Enhanced bioavailable iodine molecules |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1807604A1 (de) * | 1968-11-07 | 1970-06-11 | Diamalt Ag | Futtermittelzusatz |
GB1380274A (en) | 1971-10-01 | 1975-01-08 | Wyeth John & Brother Ltd | Amino acid derivatives |
CH591918A5 (ja) * | 1974-03-05 | 1977-10-14 | Nestle Sa | |
US4147873A (en) * | 1977-07-01 | 1979-04-03 | Merrell Toraude Et Compagnie | α-Vinyl derivatives of α-amino acids |
US5061815A (en) * | 1988-07-06 | 1991-10-29 | Zinpro Corporation | Metal lysine complexes and method for producing metal lysine complexes |
NL9201230A (nl) | 1992-07-09 | 1994-02-01 | Dsm Nv | Werkwijze voor de bereiding van optisch aktief methionineamide. |
ES2123119T3 (es) * | 1992-12-21 | 1999-01-01 | Ajinomoto Kk | Derivado de aminoacido y agente anti-oxigeno activo. |
KR100545460B1 (ko) | 1996-09-19 | 2006-01-24 | 아벤티스 파마슈티칼스 인크. | 매트릭스 금속 단백질 분해효소의 억제제로서 유용한 3-머캅토아세틸아미노-1,5-치환된-2-옥소-아제판 유도체 |
US5885610A (en) * | 1997-03-04 | 1999-03-23 | Zinpro Corporation | By-pass rumen product |
FR2785773B1 (fr) * | 1998-11-13 | 2001-04-20 | Rhone Poulenc Nutrition Animal | Utilisation d'esters de methionine en nutrition animale |
US6770640B1 (en) * | 1998-12-31 | 2004-08-03 | Aventis Pharmaceuticals Inc. | 1-Carboxymethyl-2-oxo-azepan derivatives useful as selective inhibitors of MMP-12 |
US6486193B2 (en) * | 1998-12-31 | 2002-11-26 | Aventis Pharmaceuticals Inc. | 3-substituted pyrrolidines useful as inhibitors of matrix metalloproteinases |
FR2863620B1 (fr) * | 2003-12-16 | 2007-05-25 | Roquette Freres | Utilisation d'au moins un cetose de 3 a 5 atomes de carbone comme substitut d'agents reticulants de proteines |
AU2005200875A1 (en) * | 2004-07-06 | 2006-02-02 | Agr Science & Technology Pty Ltd | Non-protein nitrogen stock feed |
US20080255234A1 (en) * | 2007-04-11 | 2008-10-16 | Zinpro Corporation | Rumen protected lysine |
US7704521B2 (en) | 2007-04-11 | 2010-04-27 | Zinpro Corporation | Rumen protected essential amino acids |
DE102008042932A1 (de) * | 2008-10-17 | 2010-04-22 | Evonik Degussa Gmbh | Herstellung und Verwendung von Methionylmethionin als Futtermitteladditiv für Fische und Krustentiere |
-
2007
- 2007-04-11 US US11/734,028 patent/US7704521B2/en active Active
-
2008
- 2008-01-31 MX MX2009010453A patent/MX2009010453A/es active IP Right Grant
- 2008-01-31 CA CA2684427A patent/CA2684427C/en active Active
- 2008-01-31 WO PCT/US2008/052607 patent/WO2008127759A1/en active Application Filing
- 2008-01-31 JP JP2010503097A patent/JP5306321B2/ja active Active
- 2008-01-31 DE DE112008000811.6T patent/DE112008000811B4/de active Active
- 2008-01-31 EP EP08728674A patent/EP2131671A1/en not_active Withdrawn
- 2008-02-20 CL CL200800520A patent/CL2008000520A1/es unknown
- 2008-02-29 AR ARP080100858A patent/AR065561A1/es unknown
-
2009
- 2009-05-19 US US12/468,161 patent/US7846471B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US7846471B2 (en) | 2010-12-07 |
DE112008000811T5 (de) | 2010-01-14 |
DE112008000811B4 (de) | 2014-10-16 |
US20090232960A1 (en) | 2009-09-17 |
CL2008000520A1 (es) | 2008-07-04 |
CA2684427A1 (en) | 2008-10-23 |
MX2009010453A (es) | 2009-10-19 |
JP2010523686A (ja) | 2010-07-15 |
WO2008127759A1 (en) | 2008-10-23 |
CA2684427C (en) | 2012-05-01 |
US20080255219A1 (en) | 2008-10-16 |
US7704521B2 (en) | 2010-04-27 |
AR065561A1 (es) | 2009-06-17 |
EP2131671A1 (en) | 2009-12-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6403697B2 (ja) | 飼料添加剤としてのジペプチド | |
JP6033254B2 (ja) | 魚類及び甲殻類用飼料添加剤としてのメチオニル−メチオニンの製造及び使用 | |
US5885610A (en) | By-pass rumen product | |
US20040137108A1 (en) | Composition for supplementing animals with solutions of essential metal amino acid complexes | |
JP5306321B2 (ja) | 反芻動物用餌補完用組成物及び反芻動物餌補完方法 | |
KR101548627B1 (ko) | 향상된 생체이용가능한 요오드 분자 | |
JP5269068B2 (ja) | 第一胃内で保護されたリシン | |
US10206415B2 (en) | Folic acid rumen by-pass method and composition | |
NZ614841B2 (en) | Enhanced bioavailable iodine molecules | |
FR2880017A1 (fr) | Procede d'obtention d'un engrais organo mineral |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20120925 |
|
A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20121220 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20130122 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20130419 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20130426 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20130516 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20130611 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20130625 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 Ref document number: 5306321 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |