JPS5814427B2 - Ｎ−モノヒドロキシメチル−又はｎ−ビスヒドロキシメチル−リジンのカルシウム塩の製法 - Google Patents
Ｎ−モノヒドロキシメチル−又はｎ−ビスヒドロキシメチル−リジンのカルシウム塩の製法Info
- Publication number
- JPS5814427B2 JPS5814427B2 JP51069649A JP6964976A JPS5814427B2 JP S5814427 B2 JPS5814427 B2 JP S5814427B2 JP 51069649 A JP51069649 A JP 51069649A JP 6964976 A JP6964976 A JP 6964976A JP S5814427 B2 JPS5814427 B2 JP S5814427B2
- Authority
- JP
- Japan
- Prior art keywords
- lysine
- calcium
- calcium salt
- monohydroxymethyl
- bishydroxymethyl
- 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
Links
- 159000000007 calcium salts Chemical class 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 4
- OFKKYYNKOOBOEL-YFKPBYRVSA-N (2S)-6-amino-2-(dihydroxymethylamino)hexanoic acid Chemical compound NCCCC[C@H](NC(O)O)C(O)=O OFKKYYNKOOBOEL-YFKPBYRVSA-N 0.000 title claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 56
- 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 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- HRTUATFMHZMKRU-LURJTMIESA-N (2s)-6-amino-2-(hydroxymethylamino)hexanoic acid Chemical compound NCCCC[C@@H](C(O)=O)NCO HRTUATFMHZMKRU-LURJTMIESA-N 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910001424 calcium ion Inorganic materials 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 29
- 235000018977 lysine Nutrition 0.000 description 23
- 241001465754 Metazoa Species 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- 229940043430 calcium compound Drugs 0.000 description 9
- 150000001674 calcium compounds Chemical class 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 235000001014 amino acid Nutrition 0.000 description 6
- 150000001413 amino acids Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BVHLGVCQOALMSV-JEDNCBNOSA-N L-lysine hydrochloride Chemical compound Cl.NCCCC[C@H](N)C(O)=O BVHLGVCQOALMSV-JEDNCBNOSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 4
- 239000000920 calcium hydroxide Substances 0.000 description 4
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 4
- 235000019766 L-Lysine Nutrition 0.000 description 3
- 241000282849 Ruminantia Species 0.000 description 3
- -1 monohydroxymethyl compound Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 241001494479 Pecora Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002668 lysine derivatives Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 210000004767 rumen Anatomy 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WUNWNURVJGOTHZ-YFKPBYRVSA-N (2s)-2-(hydroxymethylamino)-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)NCO WUNWNURVJGOTHZ-YFKPBYRVSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 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
- 241000282887 Suidae Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 210000003165 abomasum Anatomy 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical compound OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 150000002741 methionine derivatives Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005375 photometry Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S426/00—Food or edible material: processes, compositions, and products
- Y10S426/807—Poultry or ruminant feed
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Fodder In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Feed For Specific Animals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2526750A DE2526750C3 (de) | 1975-06-14 | 1975-06-14 | Calciumsalz von N-Monohydroxymethyl-L-lysin und Na, und Ne -Bishydroxymethyl-L-lysin, Verfahren zu deren Herstellung und deren Verwendung zur Supplementierung von Futter für Wiederkäuer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52221A JPS52221A (en) | 1977-01-05 |
| JPS5814427B2 true JPS5814427B2 (ja) | 1983-03-18 |
Family
ID=5949180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51069649A Expired JPS5814427B2 (ja) | 1975-06-14 | 1976-06-14 | Ｎ−モノヒドロキシメチル−又はｎ−ビスヒドロキシメチル−リジンのカルシウム塩の製法 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4073945A (enExample) |
| JP (1) | JPS5814427B2 (enExample) |
| AR (1) | AR207082A1 (enExample) |
| AT (1) | AT345778B (enExample) |
| AU (1) | AU500799B2 (enExample) |
| BE (1) | BE842900A (enExample) |
| BR (1) | BR7603679A (enExample) |
| CA (1) | CA1058635A (enExample) |
| CH (1) | CH602586A5 (enExample) |
| DE (1) | DE2526750C3 (enExample) |
| FR (1) | FR2314173A1 (enExample) |
| GB (1) | GB1546961A (enExample) |
| IL (1) | IL49638A (enExample) |
| MX (1) | MX3590E (enExample) |
| NL (1) | NL184041C (enExample) |
| SE (1) | SE416644B (enExample) |
| ZA (1) | ZA763405B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU182677B (en) * | 1980-10-08 | 1984-02-28 | Mta Koezponti Hivatala | Process for increasing the biological value of manures, liquids, organic wasters and/or soils |
| US5631031A (en) * | 1994-06-13 | 1997-05-20 | Meade; Thomas L. | Water-insoluble amino acid salt |
| JPH0850976A (ja) * | 1995-06-12 | 1996-02-20 | Omron Corp | 入出力リレー用ターミナル |
| KR102068016B1 (ko) * | 2017-07-14 | 2020-01-21 | 씨제이제일제당 주식회사 | 메티오닌-금속 킬레이트 및 이의 제조방법 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2833821A (en) * | 1954-10-07 | 1958-05-06 | Du Pont | Preparation of calcium lysinate |
-
1975
- 1975-06-14 DE DE2526750A patent/DE2526750C3/de not_active Expired
-
1976
- 1976-01-01 AR AR263418A patent/AR207082A1/es active
- 1976-05-11 FR FR7614027A patent/FR2314173A1/fr active Granted
- 1976-05-13 GB GB19664/76A patent/GB1546961A/en not_active Expired
- 1976-05-18 US US05/687,503 patent/US4073945A/en not_active Expired - Lifetime
- 1976-05-24 IL IL49638A patent/IL49638A/xx unknown
- 1976-06-02 CA CA253,939A patent/CA1058635A/en not_active Expired
- 1976-06-02 NL NLAANVRAGE7605951,A patent/NL184041C/xx not_active IP Right Cessation
- 1976-06-08 ZA ZA763405A patent/ZA763405B/xx unknown
- 1976-06-09 BR BR3679/76A patent/BR7603679A/pt unknown
- 1976-06-09 MX MX76285U patent/MX3590E/es unknown
- 1976-06-11 BE BE6045551A patent/BE842900A/xx not_active IP Right Cessation
- 1976-06-11 SE SE7606694A patent/SE416644B/xx unknown
- 1976-06-11 AU AU14817/76A patent/AU500799B2/en not_active Expired
- 1976-06-11 AT AT427376A patent/AT345778B/de active
- 1976-06-14 JP JP51069649A patent/JPS5814427B2/ja not_active Expired
- 1976-06-14 CH CH753876A patent/CH602586A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE7606694L (sv) | 1976-12-15 |
| NL184041C (nl) | 1989-04-03 |
| IL49638A (en) | 1978-10-31 |
| AT345778B (de) | 1978-10-10 |
| JPS52221A (en) | 1977-01-05 |
| BE842900A (fr) | 1976-12-13 |
| CH602586A5 (enExample) | 1978-07-31 |
| IL49638A0 (en) | 1976-07-30 |
| AU500799B2 (en) | 1979-05-31 |
| AU1481776A (en) | 1977-12-15 |
| FR2314173A1 (fr) | 1977-01-07 |
| BR7603679A (pt) | 1977-01-18 |
| DE2526750B2 (de) | 1979-03-08 |
| ATA427376A (de) | 1978-02-15 |
| US4073945A (en) | 1978-02-14 |
| CA1058635A (en) | 1979-07-17 |
| SE416644B (sv) | 1981-01-26 |
| DE2526750C3 (de) | 1979-10-25 |
| ZA763405B (en) | 1977-05-25 |
| MX3590E (es) | 1981-03-24 |
| AR207082A1 (es) | 1976-09-09 |
| NL7605951A (nl) | 1976-12-16 |
| FR2314173B1 (enExample) | 1980-03-07 |
| DE2526750A1 (de) | 1976-12-30 |
| GB1546961A (en) | 1979-06-06 |
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