DE2528459B2 - Stereoisomere 3-eckige klammer auf (2-mercapto-1-methylpropyl-) thio eckige klammer zu -2-butanole, verfahren zu dessen herstellung und ihre verwendung - Google Patents
Stereoisomere 3-eckige klammer auf (2-mercapto-1-methylpropyl-) thio eckige klammer zu -2-butanole, verfahren zu dessen herstellung und ihre verwendungInfo
- Publication number
- DE2528459B2 DE2528459B2 DE19752528459 DE2528459A DE2528459B2 DE 2528459 B2 DE2528459 B2 DE 2528459B2 DE 19752528459 DE19752528459 DE 19752528459 DE 2528459 A DE2528459 A DE 2528459A DE 2528459 B2 DE2528459 B2 DE 2528459B2
- Authority
- DE
- Germany
- Prior art keywords
- mercapto
- thio
- methylpropyl
- butanol
- erythro
- 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.)
- Granted
Links
- -1 2-MERCAPTO-1-METHYLPROPYL- Chemical class 0.000 title description 10
- 238000000034 method Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 2
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical compound C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 title 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N 2-butanol Substances CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000001273 butane Substances 0.000 description 10
- 235000011194 food seasoning agent Nutrition 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 238000001030 gas--liquid chromatography Methods 0.000 description 8
- PHLKBLKTWMSFGF-UHFFFAOYSA-N 3-[(2-Mercapto-1-methylpropyl)thio]-2-butanol Chemical class CC(O)C(C)SC(C)C(C)S PHLKBLKTWMSFGF-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 241000234282 Allium Species 0.000 description 5
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 5
- 240000002234 Allium sativum Species 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 235000004611 garlic Nutrition 0.000 description 5
- 235000019640 taste Nutrition 0.000 description 5
- PQXKWPLDPFFDJP-ZXZARUISSA-N (2r,3s)-2,3-dimethyloxirane Chemical compound C[C@H]1O[C@H]1C PQXKWPLDPFFDJP-ZXZARUISSA-N 0.000 description 4
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 235000013351 cheese Nutrition 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 235000014347 soups Nutrition 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 206010013911 Dysgeusia Diseases 0.000 description 3
- 239000004278 EU approved seasoning Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000686 essence Substances 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 235000013372 meat Nutrition 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000025371 Taste disease Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 235000019656 metallic taste Nutrition 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- MJQWABQELVFQJL-UHFFFAOYSA-N 3-Mercapto-2-butanol Chemical compound CC(O)C(C)S MJQWABQELVFQJL-UHFFFAOYSA-N 0.000 description 1
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 description 1
- OUDFNZMQXZILJD-UHFFFAOYSA-N 5-methyl-2-furaldehyde Chemical compound CC1=CC=C(C=O)O1 OUDFNZMQXZILJD-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000000940 FEMA 2235 Substances 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000013614 black pepper Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 235000013409 condiments Nutrition 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229940029982 garlic powder Drugs 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229960001867 guaiacol Drugs 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 239000010501 lemon oil Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000021056 liquid food Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 235000019639 meaty taste Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- 239000001627 myristica fragrans houtt. fruit oil Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000012149 noodles Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001631 piper nigrum l. fruit oil black Substances 0.000 description 1
- 239000001931 piper nigrum l. white Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000021397 ready fried onions Nutrition 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 235000014438 salad dressings Nutrition 0.000 description 1
- 235000015067 sauces Nutrition 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000344 thiamine hydrochloride Drugs 0.000 description 1
- 235000019190 thiamine hydrochloride Nutrition 0.000 description 1
- 239000011747 thiamine hydrochloride Substances 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- DSXFPRKPFJRPIB-UHFFFAOYSA-N thiolan-3-one Chemical compound O=C1CCSC1 DSXFPRKPFJRPIB-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- A23L13/00—Meat products; Meat meal; Preparation or treatment thereof
- A23L13/40—Meat products; Meat meal; Preparation or treatment thereof containing additives
- A23L13/42—Additives other than enzymes or microorganisms in meat products or meat meals
- A23L13/426—Addition of proteins, carbohydrates or fibrous material from vegetable origin other than sugars or sugar alcohols
-
- 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
- A23L27/202—Aliphatic compounds
- A23L27/2022—Aliphatic compounds containing sulfur
-
- 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
- A23L27/206—Dairy flavours
-
- 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
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
-
- 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
- A23L27/60—Salad dressings; Mayonnaise; Ketchup
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Dairy Products (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US499898A US3907900A (en) | 1974-08-23 | 1974-08-23 | Stero configurations of 3((2-mercapto-1-methylpropyl)thio)-2-butanol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2528459A1 DE2528459A1 (de) | 1976-03-11 |
| DE2528459B2 true DE2528459B2 (de) | 1976-09-02 |
Family
ID=23987204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752528459 Granted DE2528459B2 (de) | 1974-08-23 | 1975-06-26 | Stereoisomere 3-eckige klammer auf (2-mercapto-1-methylpropyl-) thio eckige klammer zu -2-butanole, verfahren zu dessen herstellung und ihre verwendung |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3907900A (en, 2012) |
| JP (2) | JPS5151565A (en, 2012) |
| CH (1) | CH611276A5 (en, 2012) |
| DE (1) | DE2528459B2 (en, 2012) |
| FR (1) | FR2318866A1 (en, 2012) |
| GB (1) | GB1524836A (en, 2012) |
| NL (1) | NL7508231A (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3959509A (en) * | 1974-08-23 | 1976-05-25 | International Flavors & Fragrances Inc. | Flavoring foodstuffs using sulfur-containing compounds |
| US5514294A (en) * | 1994-11-22 | 1996-05-07 | Alliedsignal Inc. | Limonene and tetrahydrofurfuryl alcohol cleaning agent |
| RU2769674C1 (ru) * | 2021-09-20 | 2022-04-04 | Елена Викторовна Борисенко | Пищевой ароматизатор, придающий вкус и аромат концентрированного молока |
| CN114672023B (zh) * | 2022-03-03 | 2023-06-09 | 江苏环峰电工材料有限公司 | 一种柔性超支化水溶性聚酰亚胺树脂的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1411091A (fr) * | 1964-07-17 | 1965-09-17 | Rhone Poulenc Sa | Procédé de préparation d'aldéhydes et cétones alpha-éthyléniques |
| US3567782A (en) * | 1968-08-08 | 1971-03-02 | Phillips Petroleum Co | Hydroxy containing thiol sulfides |
| US3635736A (en) * | 1968-10-11 | 1972-01-18 | Monsanto Co | Flavoring food with a sugar dialkyl dithioacetal |
| US3686329A (en) * | 1969-11-25 | 1972-08-22 | Stauffer Chemical Co | Process for preparing organic thiols from polysulfides |
| US3653920A (en) * | 1970-06-18 | 1972-04-04 | Lever Brothers Ltd | Thia-alkanethiols as meat flavors |
| US3717682A (en) * | 1971-05-21 | 1973-02-20 | Hooker Chemical Corp | Process of preparing mercaptophenols |
-
1974
- 1974-08-23 US US499898A patent/US3907900A/en not_active Expired - Lifetime
-
1975
- 1975-06-26 DE DE19752528459 patent/DE2528459B2/de active Granted
- 1975-07-10 NL NL7508231A patent/NL7508231A/xx unknown
- 1975-07-11 FR FR7521817A patent/FR2318866A1/fr active Granted
- 1975-07-18 CH CH942775A patent/CH611276A5/xx not_active IP Right Cessation
- 1975-08-21 GB GB34709/75A patent/GB1524836A/en not_active Expired
- 1975-08-23 JP JP50102520A patent/JPS5151565A/ja active Granted
-
1977
- 1977-06-28 JP JP7706077A patent/JPS5344508A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5512013B2 (en, 2012) | 1980-03-29 |
| JPS5151565A (en) | 1976-05-07 |
| JPS5344508A (en) | 1978-04-21 |
| FR2318866A1 (fr) | 1977-02-18 |
| GB1524836A (en) | 1978-09-13 |
| FR2318866B1 (en, 2012) | 1978-02-24 |
| CH611276A5 (en, 2012) | 1979-05-31 |
| DE2528459A1 (de) | 1976-03-11 |
| US3907900A (en) | 1975-09-23 |
| JPS5248187B2 (en, 2012) | 1977-12-08 |
| NL7508231A (nl) | 1976-02-25 |
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