NO122312B - - Google Patents
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- Publication number
- NO122312B NO122312B NO2202/68A NO220268A NO122312B NO 122312 B NO122312 B NO 122312B NO 2202/68 A NO2202/68 A NO 2202/68A NO 220268 A NO220268 A NO 220268A NO 122312 B NO122312 B NO 122312B
- Authority
- NO
- Norway
- Prior art keywords
- zearalanol
- mixture
- melting
- solution
- diastereoisomers
- Prior art date
Links
- 238000002844 melting Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 26
- FPQFYIAXQDXNOR-QDKLYSGJSA-N alpha-Zearalenol Chemical compound O=C1O[C@@H](C)CCC[C@H](O)CCC\C=C\C2=CC(O)=CC(O)=C21 FPQFYIAXQDXNOR-QDKLYSGJSA-N 0.000 claims description 24
- 229960002300 zeranol Drugs 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 230000008018 melting Effects 0.000 claims description 20
- 239000013078 crystal Substances 0.000 claims description 14
- 229960000583 acetic acid Drugs 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000012362 glacial acetic acid Substances 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 7
- 238000001816 cooling Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 14
- 239000000463 material Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- APJDQUGPCJRQRJ-LBPRGKRZSA-N Zearalanone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCCCCC2=CC(O)=CC(O)=C21 APJDQUGPCJRQRJ-LBPRGKRZSA-N 0.000 description 3
- APJDQUGPCJRQRJ-UHFFFAOYSA-N Zearalanone Natural products O=C1OC(C)CCCC(=O)CCCCCC2=CC(O)=CC(O)=C21 APJDQUGPCJRQRJ-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229940106582 estrogenic substances Drugs 0.000 description 1
- JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- MBMQEIFVQACCCH-UHFFFAOYSA-N trans-Zearalenon Natural products O=C1OC(C)CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-UHFFFAOYSA-N 0.000 description 1
- MBMQEIFVQACCCH-QBODLPLBSA-N zearalenone Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C\C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-QBODLPLBSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US64381967A | 1967-06-06 | 1967-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122312B true NO122312B (xx) | 1971-06-14 |
Family
ID=24582349
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2202/68A NO122312B (xx) | 1967-06-06 | 1968-06-05 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3574235A (xx) |
| JP (1) | JPS524556B1 (xx) |
| AT (1) | AT282839B (xx) |
| BE (1) | BE716142A (xx) |
| CH (1) | CH498790A (xx) |
| DE (1) | DE1768561B1 (xx) |
| DK (1) | DK121608B (xx) |
| ES (1) | ES354916A1 (xx) |
| FR (1) | FR1568526A (xx) |
| GB (1) | GB1190152A (xx) |
| IE (1) | IE32061B1 (xx) |
| IL (1) | IL29915A (xx) |
| NL (1) | NL6807789A (xx) |
| NO (1) | NO122312B (xx) |
| SE (1) | SE352629B (xx) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4052414A (en) * | 1971-03-01 | 1977-10-04 | Imc Chemical Group, Inc. | Cis-zearalanone, cis-zearalenol, and cis-zearalene |
| US3687982A (en) * | 1971-03-09 | 1972-08-29 | Commercial Solvents Corp | Separation of mixed diastereoisomers of zearalanol |
| JPS5465944U (xx) * | 1977-10-19 | 1979-05-10 | ||
| JPS5957663U (ja) * | 1982-10-08 | 1984-04-14 | 森 友睦 | 浄化カバ− |
| FR2571372B1 (fr) * | 1984-07-25 | 1987-05-22 | Panmedica Sa | Procede de separation des diastereoisomeres du zearalanol |
| US5593978A (en) * | 1993-12-15 | 1997-01-14 | Mallinckrodt Veterinary, Inc. | Growth promoting composition for fish and method of using the same |
| AU2009344073B2 (en) | 2009-04-09 | 2013-06-27 | Intervet International B.V. | A process for manufacturing Zeranol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239345A (en) * | 1965-02-15 | 1966-03-08 | Estrogenic compounds and animal growth promoters |
-
1967
- 1967-06-06 US US643819A patent/US3574235A/en not_active Expired - Lifetime
-
1968
- 1968-04-30 IL IL29915A patent/IL29915A/en unknown
- 1968-05-08 GB GB21712/68A patent/GB1190152A/en not_active Expired
- 1968-05-13 IE IE560/68A patent/IE32061B1/xx unknown
- 1968-05-22 CH CH758868A patent/CH498790A/de not_active IP Right Cessation
- 1968-05-29 DE DE19681768561 patent/DE1768561B1/de active Pending
- 1968-05-30 ES ES354916A patent/ES354916A1/es not_active Expired
- 1968-06-04 JP JP43037807A patent/JPS524556B1/ja active Pending
- 1968-06-04 NL NL6807789A patent/NL6807789A/xx unknown
- 1968-06-05 NO NO2202/68A patent/NO122312B/no unknown
- 1968-06-05 BE BE716142D patent/BE716142A/xx not_active IP Right Cessation
- 1968-06-05 AT AT537068A patent/AT282839B/de not_active IP Right Cessation
- 1968-06-05 FR FR1568526D patent/FR1568526A/fr not_active Expired
- 1968-06-06 DK DK264868AA patent/DK121608B/da not_active IP Right Cessation
- 1968-06-07 SE SE07708/68A patent/SE352629B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR1568526A (xx) | 1969-05-23 |
| ES354916A1 (es) | 1969-11-16 |
| IL29915A0 (en) | 1968-06-20 |
| GB1190152A (en) | 1970-04-29 |
| CH498790A (de) | 1970-11-15 |
| US3574235A (en) | 1971-04-06 |
| DE1768561B1 (de) | 1972-02-03 |
| BE716142A (xx) | 1968-11-04 |
| AT282839B (de) | 1970-07-10 |
| NL6807789A (xx) | 1968-12-09 |
| JPS524556B1 (xx) | 1977-02-04 |
| IE32061B1 (en) | 1973-04-04 |
| IE32061L (en) | 1968-12-06 |
| IL29915A (en) | 1972-02-29 |
| SE352629B (xx) | 1973-01-08 |
| DK121608B (da) | 1971-11-08 |
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