DE1543474B1 - Zearalenol und Verfahren zu dessen Herstellung - Google Patents
Zearalenol und Verfahren zu dessen HerstellungInfo
- Publication number
- DE1543474B1 DE1543474B1 DE19661543474 DE1543474A DE1543474B1 DE 1543474 B1 DE1543474 B1 DE 1543474B1 DE 19661543474 DE19661543474 DE 19661543474 DE 1543474 A DE1543474 A DE 1543474A DE 1543474 B1 DE1543474 B1 DE 1543474B1
- Authority
- DE
- Germany
- Prior art keywords
- zearalenol
- weight
- formula
- parts
- diethylstilbestrol
- 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.)
- Pending
Links
- 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 13
- 238000000034 method Methods 0.000 title claims description 3
- 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 5
- 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 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 3
- 125000000468 ketone group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 7
- 229960000452 diethylstilbestrol Drugs 0.000 description 7
- 235000013372 meat Nutrition 0.000 description 6
- 230000001076 estrogenic effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000283903 Ovis aries Species 0.000 description 3
- 230000004584 weight gain Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 229940011871 estrogen Drugs 0.000 description 2
- 239000000262 estrogen Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- -1 methanol or ethanol Chemical compound 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-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
-
- 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
- A23K20/116—Heterocyclic compounds
- A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero atom
- A23K20/126—Lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US432848A US3239348A (en) | 1965-02-15 | 1965-02-15 | Estrogenic compounds and animal growth promoters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543474B1 true DE1543474B1 (de) | 1971-08-26 |
Family
ID=23717835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543474 Pending DE1543474B1 (de) | 1965-02-15 | 1966-02-01 | Zearalenol und Verfahren zu dessen Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3239348A (enExample) |
| BE (1) | BE675977A (enExample) |
| DE (1) | DE1543474B1 (enExample) |
| GB (1) | GB1107744A (enExample) |
| IL (1) | IL25093A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3453367A (en) * | 1966-06-29 | 1969-07-01 | Commercial Solvents Corp | Methods for treating inflammation with estrogenic compounds |
| US4690948A (en) * | 1986-12-01 | 1987-09-01 | International Minerals & Chemical Corp. | Halogenated resorcylic acid lactone derivatives |
| US4751239A (en) * | 1987-06-29 | 1988-06-14 | International Minerals & Chemical Corp. | 6' Carbonate esters of zearalanol and its derivatives |
| US4778821A (en) * | 1987-07-15 | 1988-10-18 | International Minerals & Chemical Corp. | Method for controlling helmintic parasites |
| US4902711A (en) * | 1988-01-19 | 1990-02-20 | Pitman-Moore, Inc. | 6' Carbamate esters of zearalanol and its derivatives |
| US4886899A (en) * | 1988-07-05 | 1989-12-12 | Pitman-Moore, Inc. | Housefly chemosterilants |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB783611A (en) * | 1954-06-30 | 1957-09-25 | Ici Ltd | Gibberellic acid and derivatives thereof |
-
1965
- 1965-02-15 US US432848A patent/US3239348A/en not_active Expired - Lifetime
-
1966
- 1966-02-01 GB GB4324/66A patent/GB1107744A/en not_active Expired
- 1966-02-01 IL IL25093A patent/IL25093A/xx unknown
- 1966-02-01 DE DE19661543474 patent/DE1543474B1/de active Pending
- 1966-02-02 BE BE675977D patent/BE675977A/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| US3239348A (en) | 1966-03-08 |
| BE675977A (enExample) | 1966-06-16 |
| IL25093A (en) | 1969-11-12 |
| GB1107744A (en) | 1968-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |