JPH0567638B2 - - Google Patents
Info
- Publication number
- JPH0567638B2 JPH0567638B2 JP58111975A JP11197583A JPH0567638B2 JP H0567638 B2 JPH0567638 B2 JP H0567638B2 JP 58111975 A JP58111975 A JP 58111975A JP 11197583 A JP11197583 A JP 11197583A JP H0567638 B2 JPH0567638 B2 JP H0567638B2
- Authority
- JP
- Japan
- Prior art keywords
- adduct
- menadione
- thiamine
- bmv
- thiamine hydrochloride
- 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 - Lifetime
Links
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 claims description 57
- 235000012711 vitamin K3 Nutrition 0.000 claims description 27
- 239000011652 vitamin K3 Substances 0.000 claims description 27
- 229940041603 vitamin k 3 Drugs 0.000 claims description 27
- JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 claims description 23
- 239000011721 thiamine Substances 0.000 claims description 20
- 235000019157 thiamine Nutrition 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229960003495 thiamine Drugs 0.000 claims description 17
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 claims description 16
- 239000012867 bioactive agent Substances 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 230000001766 physiological effect Effects 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 26
- 229960000344 thiamine hydrochloride Drugs 0.000 description 25
- 239000011747 thiamine hydrochloride Substances 0.000 description 25
- 235000019190 thiamine hydrochloride Nutrition 0.000 description 24
- 229960004051 menadione sodium bisulfite Drugs 0.000 description 16
- XDPFHGWVCTXHDX-UHFFFAOYSA-M menadione sodium sulfonate Chemical compound [Na+].C1=CC=C2C(=O)C(C)(S([O-])(=O)=O)CC(=O)C2=C1 XDPFHGWVCTXHDX-UHFFFAOYSA-M 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 9
- 235000019743 Choline chloride Nutrition 0.000 description 9
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 9
- 229960003178 choline chloride Drugs 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 229940088594 vitamin Drugs 0.000 description 9
- 239000011782 vitamin Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 235000013619 trace mineral Nutrition 0.000 description 5
- 239000011573 trace mineral Substances 0.000 description 5
- 229930003231 vitamin Natural products 0.000 description 5
- 235000013343 vitamin Nutrition 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 150000003722 vitamin derivatives Chemical class 0.000 description 4
- -1 4-amino-2-methyl-5-pyrimidinyl-methyl Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000006069 physical mixture Substances 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- 230000001225 therapeutic effect Effects 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 2
- 241001465754 Metazoa Species 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 108010068370 Glutens Proteins 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
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003716 vitamin K3 derivatives Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D415/00—Heterocyclic compounds containing the thiamine skeleton
-
- 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
- A23K20/174—Vitamins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT22051/82A IT1159074B (it) | 1982-06-24 | 1982-06-24 | Composto di addizione fra menadione e tiamina a reciproca stabilizzazione |
| IT22051A/82 | 1982-06-24 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5925324A JPS5925324A (ja) | 1984-02-09 |
| JPH0567638B2 true JPH0567638B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-09-27 |
Family
ID=11190742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58111975A Granted JPS5925324A (ja) | 1982-06-24 | 1983-06-23 | メナジオンとチアミンとを相互に安定化するアダクト |
Country Status (11)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808602A (en) * | 1986-02-27 | 1989-02-28 | Heterochemical Corporation | Derivatives based upon pyrido-menadione adducts and use thereof as feed premixes |
| WO2017137530A1 (en) | 2016-02-12 | 2017-08-17 | Akzo Nobel Chemicals International B.V. | Process to prepare higher ethylene amines and ethylene amine derivatives |
| CN108602752B (zh) | 2016-02-12 | 2021-07-02 | 阿克苏诺贝尔化学品国际有限公司 | 制备高级亚乙基胺和亚乙基胺衍生物的方法 |
| EP3414221B1 (en) | 2016-02-12 | 2021-09-01 | Nouryon Chemicals International B.V. | Process to prepare higher ethylene amines and ethylene amine derivatives |
| EP3652154B1 (en) | 2017-07-10 | 2021-05-12 | Nouryon Chemicals International B.V. | Process to prepare ethylene amines and ethylene amine derivatives |
| WO2019011708A1 (en) | 2017-07-10 | 2019-01-17 | Akzo Nobel Chemicals International B.V. | PROCESS FOR THE PRODUCTION OF SUPERIOR ETHYLENEAMINES |
| TWI768076B (zh) | 2017-07-10 | 2022-06-21 | 荷蘭商安科智諾貝爾化學國際公司 | 製造直鏈及非直鏈伸乙基胺混合物之方法 |
| TWI762670B (zh) | 2017-07-10 | 2022-05-01 | 荷蘭商安科智諾貝爾化學國際公司 | 製備較高分子量伸乙基胺或其脲衍生物之方法 |
| CN107501254A (zh) * | 2017-08-15 | 2017-12-22 | 江西森泰药业有限公司 | 饲料添加剂维生素b1的制备工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB685667A (en) * | 1949-12-05 | 1953-01-07 | Bayer Ag | A sparingly soluble new vitamin b salt and foodstuffs enriched therewith |
| US3931152A (en) * | 1974-01-29 | 1976-01-06 | American Cyanamid Company | 2-(1,3-Diazacycloalkenyl)-2-hydrazones of substituted chalcones |
| US4006234A (en) * | 1974-12-18 | 1977-02-01 | American Cyanamid Company | Substituted 2-benzofuranyl propenones as anti-tubercular agents |
| JPS5231981A (en) * | 1975-08-18 | 1977-03-10 | Takeda Chem Ind Ltd | Microcapsule preparation method |
| GB2047739A (en) * | 1979-04-27 | 1980-12-03 | Roche Products Ltd | Nutrient medium |
-
1982
- 1982-06-24 IT IT22051/82A patent/IT1159074B/it active
-
1983
- 1983-06-18 AT AT83105975T patent/ATE25979T1/de not_active IP Right Cessation
- 1983-06-18 EP EP83105975A patent/EP0098995B1/en not_active Expired
- 1983-06-18 DE DE8383105975T patent/DE3370330D1/de not_active Expired
- 1983-06-21 IL IL69035A patent/IL69035A0/xx unknown
- 1983-06-22 US US06/506,847 patent/US4568745A/en not_active Expired - Fee Related
- 1983-06-23 JP JP58111975A patent/JPS5925324A/ja active Granted
- 1983-06-23 ES ES523528A patent/ES8507453A1/es not_active Expired
- 1983-06-24 AR AR293432A patent/AR230185A1/es active
- 1983-06-24 CA CA000431183A patent/CA1216794A/en not_active Expired
- 1983-06-24 IE IE1482/83A patent/IE55626B1/en not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS * |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0098995A1 (en) | 1984-01-25 |
| AR230185A1 (es) | 1984-03-01 |
| ES523528A0 (es) | 1985-10-01 |
| DE3370330D1 (en) | 1987-04-23 |
| ES8507453A1 (es) | 1985-10-01 |
| EP0098995B1 (en) | 1987-03-18 |
| JPS5925324A (ja) | 1984-02-09 |
| IT1159074B (it) | 1987-02-25 |
| CA1216794A (en) | 1987-01-20 |
| US4568745A (en) | 1986-02-04 |
| IL69035A0 (en) | 1983-10-31 |
| ATE25979T1 (de) | 1987-04-15 |
| IE831482L (en) | 1983-12-24 |
| IE55626B1 (en) | 1990-12-05 |
| IT8222051A0 (it) | 1982-06-24 |
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