DE2111606C3 - Verfahren zur Herstellung eines Diasteroisomerengemisches von Zearalanol - Google Patents
Verfahren zur Herstellung eines Diasteroisomerengemisches von ZearalanolInfo
- Publication number
- DE2111606C3 DE2111606C3 DE2111606A DE2111606A DE2111606C3 DE 2111606 C3 DE2111606 C3 DE 2111606C3 DE 2111606 A DE2111606 A DE 2111606A DE 2111606 A DE2111606 A DE 2111606A DE 2111606 C3 DE2111606 C3 DE 2111606C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- melting
- diastereoisomers
- mixture
- zearalanol
- 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
- 239000000203 mixture Substances 0.000 title claims description 17
- 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 title claims description 11
- 229960002300 zeranol Drugs 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 238000002844 melting Methods 0.000 claims description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 9
- MBMQEIFVQACCCH-UHFFFAOYSA-N trans-Zearalenon Natural products O=C1OC(C)CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 9
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000003054 catalyst Substances 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
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 238000006722 reduction reaction Methods 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 230000008018 melting Effects 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- MWFRFJUAYHVDJP-UHFFFAOYSA-N C(CC)O.CC(C)O.C(CC)O Chemical compound C(CC)O.CC(C)O.C(CC)O MWFRFJUAYHVDJP-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application 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
- OCLXJTCGWSSVOE-UHFFFAOYSA-N ethanol etoh Chemical compound CCO.CCO OCLXJTCGWSSVOE-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 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)
- Fodder In General (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2526570A | 1970-04-02 | 1970-04-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2111606A1 DE2111606A1 (de) | 1971-10-21 |
| DE2111606B2 DE2111606B2 (de) | 1981-01-29 |
| DE2111606C3 true DE2111606C3 (de) | 1982-01-07 |
Family
ID=21825011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2111606A Expired DE2111606C3 (de) | 1970-04-02 | 1971-03-11 | Verfahren zur Herstellung eines Diasteroisomerengemisches von Zearalanol |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3697548A (en:Method) |
| JP (1) | JPS4921152B1 (en:Method) |
| AT (1) | AT310767B (en:Method) |
| AU (1) | AU490537B2 (en:Method) |
| BE (1) | BE765130A (en:Method) |
| CH (1) | CH554329A (en:Method) |
| DE (1) | DE2111606C3 (en:Method) |
| DK (1) | DK128076B (en:Method) |
| FR (1) | FR2092489A5 (en:Method) |
| GB (1) | GB1298316A (en:Method) |
| IL (1) | IL36349A (en:Method) |
| NL (1) | NL161447C (en:Method) |
| SE (1) | SE359540B (en:Method) |
| ZA (1) | ZA711329B (en:Method) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3818044A (en) * | 1972-01-17 | 1974-06-18 | Commercial Solvents Corp | Preparation of zearalanone or of racemic mixtures of zearalanol diamers |
| US3808233A (en) * | 1972-09-26 | 1974-04-30 | Commercial Solvents Corp | Zearalenone reduction |
| JPS6071191U (ja) * | 1983-10-24 | 1985-05-20 | 富士通テン株式会社 | 印刷配線基板の接続構造 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3239345A (en) * | 1965-02-15 | 1966-03-08 | Estrogenic compounds and animal growth promoters | |
| NL131475C (en:Method) * | 1965-02-15 |
-
1970
- 1970-04-02 US US25265A patent/US3697548A/en not_active Expired - Lifetime
-
1971
- 1971-03-02 ZA ZA711329A patent/ZA711329B/xx unknown
- 1971-03-04 IL IL36349A patent/IL36349A/en unknown
- 1971-03-11 DE DE2111606A patent/DE2111606C3/de not_active Expired
- 1971-03-19 CH CH405271A patent/CH554329A/xx not_active IP Right Cessation
- 1971-03-24 AT AT254071A patent/AT310767B/de not_active IP Right Cessation
- 1971-03-25 FR FR7110556A patent/FR2092489A5/fr not_active Expired
- 1971-03-29 NL NL7104198.A patent/NL161447C/xx not_active IP Right Cessation
- 1971-03-30 JP JP46018450A patent/JPS4921152B1/ja active Pending
- 1971-03-31 DK DK154471AA patent/DK128076B/da unknown
- 1971-04-01 BE BE765130A patent/BE765130A/xx not_active IP Right Cessation
- 1971-04-01 SE SE04259/71A patent/SE359540B/xx unknown
- 1971-04-19 GB GB23143/71A patent/GB1298316A/en not_active Expired
-
1975
- 1975-10-20 AU AU85868/75A patent/AU490537B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2111606A1 (de) | 1971-10-21 |
| NL7104198A (en:Method) | 1971-10-05 |
| ZA711329B (en) | 1971-12-29 |
| AT310767B (de) | 1973-10-10 |
| IL36349A0 (en) | 1971-05-26 |
| SE359540B (en:Method) | 1973-09-03 |
| BE765130A (fr) | 1971-08-30 |
| DE2111606B2 (de) | 1981-01-29 |
| US3697548A (en) | 1972-10-10 |
| IL36349A (en) | 1973-07-30 |
| JPS4921152B1 (en:Method) | 1974-05-30 |
| GB1298316A (en) | 1972-11-29 |
| NL161447B (nl) | 1979-09-17 |
| AU490537B2 (en) | 1975-12-18 |
| FR2092489A5 (en:Method) | 1972-01-21 |
| NL161447C (nl) | 1980-02-15 |
| CH554329A (de) | 1974-09-30 |
| DK128076B (da) | 1974-02-25 |
| AU8586875A (en) | 1975-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) |