DE2335277C3 - Substituierte Furenidone, Verfahren zu deren Herstellung und deren Verwendung - Google Patents
Substituierte Furenidone, Verfahren zu deren Herstellung und deren VerwendungInfo
- Publication number
- DE2335277C3 DE2335277C3 DE2335277A DE2335277A DE2335277C3 DE 2335277 C3 DE2335277 C3 DE 2335277C3 DE 2335277 A DE2335277 A DE 2335277A DE 2335277 A DE2335277 A DE 2335277A DE 2335277 C3 DE2335277 C3 DE 2335277C3
- Authority
- DE
- Germany
- Prior art keywords
- furenidones
- substituted
- hydroxy
- singlet
- food
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims 3
- 150000001875 compounds Chemical class 0.000 claims description 19
- 235000013305 food Nutrition 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 7
- -1 methylfuryl Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000796 flavoring agent Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 235000019634 flavors Nutrition 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000002978 peroxides Chemical class 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- TXBANKNWILQCFG-UHFFFAOYSA-N 4-hydroxyfuran-3-one Chemical compound OC1=COCC1=O TXBANKNWILQCFG-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 12
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 10
- 230000009102 absorption Effects 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- 239000003925 fat Substances 0.000 description 9
- 235000019197 fats Nutrition 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 235000013310 margarine Nutrition 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000004952 Polyamide Substances 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 229920002647 polyamide Polymers 0.000 description 4
- 235000014347 soups Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000003264 margarine Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- VVGOCOMZRGWHPI-ARJAWSKDSA-N (z)-4-heptenal Chemical compound CC\C=C/CCC=O VVGOCOMZRGWHPI-ARJAWSKDSA-N 0.000 description 2
- HEBLFQHRAHRFNP-UHFFFAOYSA-N 4-hydroxy-2-(1-hydroxyethyl)-2,5-dimethylfuran-3-one Chemical compound CC(O)C1(C)OC(C)=C(O)C1=O HEBLFQHRAHRFNP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 description 1
- DSMRYCOTKWYTRF-UHFFFAOYSA-N 3-methylfuran-2-carbaldehyde Chemical compound CC=1C=COC=1C=O DSMRYCOTKWYTRF-UHFFFAOYSA-N 0.000 description 1
- UIBVNOKZULAKRC-UHFFFAOYSA-N 4-hydroxy-2-(2-hydroxypropan-2-yl)-2,5-dimethylfuran-3-one Chemical compound CC1=C(O)C(=O)C(C)(C(C)(C)O)O1 UIBVNOKZULAKRC-UHFFFAOYSA-N 0.000 description 1
- PIZJHVUCLPRODH-UHFFFAOYSA-N 4-hydroxy-2-[(1-hydroxycyclohexa-2,4-dien-1-yl)methyl]-2,5-dimethylfuran-3-one Chemical compound O1C(C)=C(O)C(=O)C1(C)CC1(O)C=CC=CC1 PIZJHVUCLPRODH-UHFFFAOYSA-N 0.000 description 1
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000009739 binding Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 235000008378 frozen soup Nutrition 0.000 description 1
- 235000015143 herbs and spices Nutrition 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- 239000004223 monosodium glutamate Substances 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 235000015927 pasta Nutrition 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 235000020995 raw meat Nutrition 0.000 description 1
- 235000015504 ready meals Nutrition 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/60—Two oxygen atoms, e.g. succinic anhydride
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT OF FLOUR OR DOUGH FOR BAKING, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L23/00—Soups; Sauces; Preparation or treatment thereof
- A23L23/10—Soup concentrates, e.g. powders or cakes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Seasonings (AREA)
- Fats And Perfumes (AREA)
- Furan Compounds (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3265372A GB1434194A (en) | 1972-07-12 | 1972-07-12 | Substituted furenidones and their use as flavouring agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2335277A1 DE2335277A1 (de) | 1974-01-31 |
| DE2335277B2 DE2335277B2 (de) | 1979-08-02 |
| DE2335277C3 true DE2335277C3 (de) | 1980-04-10 |
Family
ID=10341984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2335277A Expired DE2335277C3 (de) | 1972-07-12 | 1973-07-11 | Substituierte Furenidone, Verfahren zu deren Herstellung und deren Verwendung |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3950565A (enExample) |
| JP (1) | JPS541789B2 (enExample) |
| AT (1) | AT328842B (enExample) |
| AU (1) | AU472089B2 (enExample) |
| BE (1) | BE802277A (enExample) |
| CA (1) | CA1008869A (enExample) |
| CH (1) | CH587260A5 (enExample) |
| DE (1) | DE2335277C3 (enExample) |
| FR (1) | FR2192101B1 (enExample) |
| GB (1) | GB1434194A (enExample) |
| IT (1) | IT1043864B (enExample) |
| NL (1) | NL161044C (enExample) |
| ZA (1) | ZA734623B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59144334A (ja) * | 1983-02-03 | 1984-08-18 | Nippon Electric Ind Co Ltd | 踏切しや断機用モ−タ |
| DE3866955D1 (de) * | 1987-05-14 | 1992-01-30 | Unilever Nv | Verwendung von diketonvorlaeufern in nahrungsmitteln. |
| EP0784936A1 (en) | 1996-01-17 | 1997-07-23 | Unilever Plc | Process for the preparation of a savoury flavour |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH486850A (de) * | 1964-12-31 | 1970-03-15 | Firmenich & Cie | Verwendung von Dihydrofuranderivaten als Geschmackstoffe |
| GB1224989A (en) * | 1967-09-22 | 1971-03-10 | Unilever Ltd | Meat flavoured products |
| GB1302525A (enExample) * | 1969-03-25 | 1973-01-10 |
-
1972
- 1972-07-12 GB GB3265372A patent/GB1434194A/en not_active Expired
-
1973
- 1973-07-10 AU AU57915/73A patent/AU472089B2/en not_active Expired
- 1973-07-11 DE DE2335277A patent/DE2335277C3/de not_active Expired
- 1973-07-11 FR FR7325490A patent/FR2192101B1/fr not_active Expired
- 1973-07-11 NL NL7309647.A patent/NL161044C/xx not_active IP Right Cessation
- 1973-07-11 IT IT69079/73A patent/IT1043864B/it active
- 1973-07-11 US US05/378,085 patent/US3950565A/en not_active Expired - Lifetime
- 1973-07-11 AT AT609973A patent/AT328842B/de not_active IP Right Cessation
- 1973-07-12 BE BE133422A patent/BE802277A/xx not_active IP Right Cessation
- 1973-07-12 CH CH1019673A patent/CH587260A5/xx not_active IP Right Cessation
- 1973-07-12 CA CA176,290A patent/CA1008869A/en not_active Expired
- 1973-07-12 JP JP7890173A patent/JPS541789B2/ja not_active Expired
- 1973-07-18 ZA ZA00734623A patent/ZA734623B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA734623B (en) | 1975-02-26 |
| NL161044B (nl) | 1979-08-15 |
| CA1008869A (en) | 1977-04-19 |
| BE802277A (fr) | 1974-01-14 |
| GB1434194A (en) | 1976-05-05 |
| US3950565A (en) | 1976-04-13 |
| AU5791573A (en) | 1975-01-16 |
| DE2335277A1 (de) | 1974-01-31 |
| CH587260A5 (enExample) | 1977-04-29 |
| NL7309647A (enExample) | 1974-01-15 |
| FR2192101B1 (enExample) | 1978-08-11 |
| JPS541789B2 (enExample) | 1979-01-29 |
| JPS4951263A (enExample) | 1974-05-18 |
| IT1043864B (it) | 1980-02-29 |
| AT328842B (de) | 1976-04-12 |
| NL161044C (nl) | 1980-01-15 |
| ATA609973A (de) | 1975-06-15 |
| DE2335277B2 (de) | 1979-08-02 |
| FR2192101A1 (enExample) | 1974-02-08 |
| AU472089B2 (en) | 1976-05-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: KOHLER, M., DIPL.-CHEM. DR.RER.NAT., 8000 MUENCHEN GLAESER, J., DIPL.-ING., PAT.-ANW., 2000 HAMBURG |
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| 8339 | Ceased/non-payment of the annual fee |