DE2159007C3 - Verfahren zur Herstellung von cis-Zearalenon oder cis-Zearalenol - Google Patents
Verfahren zur Herstellung von cis-Zearalenon oder cis-ZearalenolInfo
- Publication number
- DE2159007C3 DE2159007C3 DE2159007A DE2159007A DE2159007C3 DE 2159007 C3 DE2159007 C3 DE 2159007C3 DE 2159007 A DE2159007 A DE 2159007A DE 2159007 A DE2159007 A DE 2159007A DE 2159007 C3 DE2159007 C3 DE 2159007C3
- Authority
- DE
- Germany
- Prior art keywords
- cis
- zearalenol
- zearalenone
- trans
- solution
- 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
- 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 16
- 238000000034 method Methods 0.000 title claims description 12
- MBMQEIFVQACCCH-UHFFFAOYSA-N trans-Zearalenon Natural products O=C1OC(C)CCCC(=O)CCCC=CC2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-UHFFFAOYSA-N 0.000 title claims description 9
- MBMQEIFVQACCCH-MIBUCLJRSA-N (2z,11s)-15,17-dihydroxy-11-methyl-12-oxabicyclo[12.4.0]octadeca-1(14),2,15,17-tetraene-7,13-dione Chemical compound O=C1O[C@@H](C)CCCC(=O)CCC\C=C/C2=CC(O)=CC(O)=C21 MBMQEIFVQACCCH-MIBUCLJRSA-N 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- 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 6
- 239000011261 inert gas Substances 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 239000012298 atmosphere Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 238000006317 isomerization reaction Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000005388 borosilicate glass Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- UIAFKZKHHVMJGS-UHFFFAOYSA-N beta-resorcylic acid Natural products OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007697 cis-trans-isomerization reaction Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 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
- A23K20/184—Hormones
-
- 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)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Endocrinology (AREA)
- Health & Medical Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Fodder In General (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Moulds For Moulding Plastics Or The Like (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11983371A | 1971-03-01 | 1971-03-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2159007A1 DE2159007A1 (de) | 1972-09-07 |
| DE2159007B2 DE2159007B2 (de) | 1974-08-08 |
| DE2159007C3 true DE2159007C3 (de) | 1975-04-10 |
Family
ID=22386657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2159007A Expired DE2159007C3 (de) | 1971-03-01 | 1971-11-29 | Verfahren zur Herstellung von cis-Zearalenon oder cis-Zearalenol |
Country Status (17)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS53120870A (en) * | 1977-03-30 | 1978-10-21 | Tatsuo Murakami | Light decoradive unit |
| JPS60123906U (ja) * | 1984-01-28 | 1985-08-21 | 森村興産株式会社 | 照明装置 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE611630A (enrdf_load_stackoverflow) * | 1960-12-16 | |||
| US3551455A (en) * | 1967-09-13 | 1970-12-29 | Merck & Co Inc | Total synthesis of zearalenone |
-
1971
- 1971-09-21 CA CA123,344A patent/CA1028714A/en not_active Expired
- 1971-09-27 IL IL37800A patent/IL37800A/xx unknown
- 1971-09-27 AU AU33921/71A patent/AU453069B2/en not_active Expired
- 1971-09-28 ZA ZA716511A patent/ZA716511B/xx unknown
- 1971-10-18 CH CH1519871A patent/CH559744A5/xx not_active IP Right Cessation
- 1971-11-04 BR BR7371/71A patent/BR7107371D0/pt unknown
- 1971-11-12 JP JP46089982A patent/JPS4925273B1/ja active Pending
- 1971-11-22 NL NLAANVRAGE7116018,A patent/NL176941C/xx not_active IP Right Cessation
- 1971-11-23 FR FR7141798A patent/FR2128271B1/fr not_active Expired
- 1971-11-24 GB GB5453571A patent/GB1328037A/en not_active Expired
- 1971-11-25 IE IE1494/71A patent/IE35849B1/xx unknown
- 1971-11-25 NO NO4345/71A patent/NO133499C/no unknown
- 1971-11-29 DE DE2159007A patent/DE2159007C3/de not_active Expired
- 1971-11-30 AT AT1031371A patent/AT314747B/de not_active IP Right Cessation
- 1971-12-02 SE SE7115476A patent/SE386447B/xx unknown
- 1971-12-03 BE BE776194A patent/BE776194A/xx not_active IP Right Cessation
- 1971-12-10 DK DK604671AA patent/DK130792B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU453069B2 (en) | 1974-09-19 |
| NL7116018A (enrdf_load_stackoverflow) | 1972-09-05 |
| JPS4925273B1 (enrdf_load_stackoverflow) | 1974-06-28 |
| NO133499B (enrdf_load_stackoverflow) | 1976-02-02 |
| BR7107371D0 (pt) | 1973-02-20 |
| DK130792C (enrdf_load_stackoverflow) | 1975-09-15 |
| FR2128271A1 (enrdf_load_stackoverflow) | 1972-10-20 |
| ZA716511B (en) | 1972-06-28 |
| NL176941C (nl) | 1985-07-01 |
| CA1028714A (en) | 1978-03-28 |
| NO133499C (enrdf_load_stackoverflow) | 1976-05-12 |
| IL37800A (en) | 1974-10-22 |
| GB1328037A (en) | 1973-08-22 |
| DK130792B (da) | 1975-04-14 |
| AT314747B (de) | 1974-04-25 |
| CH559744A5 (enrdf_load_stackoverflow) | 1975-03-14 |
| BE776194A (fr) | 1972-04-04 |
| DE2159007B2 (de) | 1974-08-08 |
| IE35849B1 (en) | 1976-06-09 |
| AU3392171A (en) | 1973-04-05 |
| FR2128271B1 (enrdf_load_stackoverflow) | 1975-06-13 |
| NL176941B (nl) | 1985-02-01 |
| IL37800A0 (en) | 1971-11-29 |
| SE386447B (sv) | 1976-08-09 |
| IE35849L (en) | 1972-09-01 |
| DE2159007A1 (de) | 1972-09-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |