DE2108727B2 - Alkylidensulfoxide, verfahren zu deren herstellung und wuerzmittel - Google Patents
Alkylidensulfoxide, verfahren zu deren herstellung und wuerzmittelInfo
- Publication number
- DE2108727B2 DE2108727B2 DE19712108727 DE2108727A DE2108727B2 DE 2108727 B2 DE2108727 B2 DE 2108727B2 DE 19712108727 DE19712108727 DE 19712108727 DE 2108727 A DE2108727 A DE 2108727A DE 2108727 B2 DE2108727 B2 DE 2108727B2
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- sulfoxides
- chloride
- alkylidene
- tear
- 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.)
- Withdrawn
Links
- 239000000796 flavoring agent Substances 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims 3
- 235000013355 food flavoring agent Nutrition 0.000 title 1
- -1 Alkylidene sulfoxides Chemical class 0.000 claims description 31
- 241000234282 Allium Species 0.000 claims description 18
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims description 18
- 235000019640 taste Nutrition 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 16
- 235000019634 flavors Nutrition 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 240000006108 Allium ampeloprasum Species 0.000 claims description 7
- 235000005254 Allium ampeloprasum Nutrition 0.000 claims description 7
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 235000011194 food seasoning agent Nutrition 0.000 claims description 6
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 235000013305 food Nutrition 0.000 claims description 5
- 229940029284 trichlorofluoromethane Drugs 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 240000002234 Allium sativum Species 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 235000004611 garlic Nutrition 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000003973 alkyl amines Chemical group 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 229930195733 hydrocarbon Natural products 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 239000012429 reaction media Substances 0.000 claims 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- 125000001118 alkylidene group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 238000002474 experimental method Methods 0.000 claims 2
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims 2
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 claims 2
- 238000002955 isolation Methods 0.000 claims 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims 2
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 claims 1
- 241000272517 Anseriformes Species 0.000 claims 1
- BTYJOAGCBJQFNL-UHFFFAOYSA-N CO[S+]=S Chemical class CO[S+]=S BTYJOAGCBJQFNL-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 239000004201 L-cysteine Substances 0.000 claims 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 claims 1
- 101100400378 Mus musculus Marveld2 gene Proteins 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 239000006227 byproduct Substances 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 235000013409 condiments Nutrition 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 claims 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims 1
- 238000007323 disproportionation reaction Methods 0.000 claims 1
- 150000002019 disulfides Chemical class 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- 239000002085 irritant Substances 0.000 claims 1
- 231100000021 irritant Toxicity 0.000 claims 1
- 230000005923 long-lasting effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 230000035479 physiological effects, processes and functions Effects 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 230000035484 reaction time Effects 0.000 claims 1
- 230000002269 spontaneous effect Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 5
- 235000015278 beef Nutrition 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000012084 conversion product Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 235000013372 meat Nutrition 0.000 description 3
- 235000019645 odor Nutrition 0.000 description 3
- ILUVJGOKAOXNHT-UHFFFAOYSA-N propane-1-sulfinyl chloride Chemical compound CCCS(Cl)=O ILUVJGOKAOXNHT-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- GGNALUCSASGNCK-UHFFFAOYSA-N carbon dioxide;propan-2-ol Chemical compound O=C=O.CC(C)O GGNALUCSASGNCK-UHFFFAOYSA-N 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 239000005022 packaging material Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- WUCQRXWCJPCWTQ-NSCUHMNNSA-N (e)-pent-3-enal Chemical compound C\C=C\CC=O WUCQRXWCJPCWTQ-NSCUHMNNSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000001270 Allium sibiricum Nutrition 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 108010058846 Ovalbumin Proteins 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000013614 black pepper Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000012813 breadcrumbs Nutrition 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- AVFZJLJBOMRLNZ-UHFFFAOYSA-N hexane-1-sulfinyl chloride Chemical compound CCCCCCS(Cl)=O AVFZJLJBOMRLNZ-UHFFFAOYSA-N 0.000 description 1
- 235000008960 ketchup Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000021201 onion's soup Nutrition 0.000 description 1
- PRDGAWNUCKTNJV-UHFFFAOYSA-N oxo-prop-1-enyl-propoxy-sulfanylidene-$l^{6}-sulfane Chemical compound CCCOS(=O)(=S)C=CC PRDGAWNUCKTNJV-UHFFFAOYSA-N 0.000 description 1
- KSOOOPXMOBQZBP-UHFFFAOYSA-N oxo-propoxy-propyl-sulfanylidene-$l^{6}-sulfane Chemical compound CCCOS(=O)(=S)CCC KSOOOPXMOBQZBP-UHFFFAOYSA-N 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- WUCQRXWCJPCWTQ-UHFFFAOYSA-N trans-3-pentenal Natural products CC=CCC=O WUCQRXWCJPCWTQ-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 235000008939 whole milk Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/04—Thiosulfonates
-
- 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
- A23L27/201—Compounds of unspecified constitution characterised by the chemical reaction for their preparation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C325/00—Thioaldehydes; Thioketones; Thioquinones; Oxides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Seasonings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Bakery Products And Manufacturing Methods Therefor (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1381670A | 1970-02-24 | 1970-02-24 | |
| US10475871A | 1971-01-07 | 1971-01-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2108727A1 DE2108727A1 (de) | 1971-09-16 |
| DE2108727B2 true DE2108727B2 (de) | 1973-08-16 |
Family
ID=26685289
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712108727 Withdrawn DE2108727B2 (de) | 1970-02-24 | 1971-02-24 | Alkylidensulfoxide, verfahren zu deren herstellung und wuerzmittel |
| DE2166074*A Expired DE2166074C3 (de) | 1970-02-24 | 1971-02-24 | 07.01.71 USA 104758 Propylpropenylthiosulfonat dessen Herstellung und ein dieses enthaltendes Würzmittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2166074*A Expired DE2166074C3 (de) | 1970-02-24 | 1971-02-24 | 07.01.71 USA 104758 Propylpropenylthiosulfonat dessen Herstellung und ein dieses enthaltendes Würzmittel |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3751269A (enExample) |
| JP (1) | JPS5113129B2 (enExample) |
| BE (1) | BE763403A (enExample) |
| CA (1) | CA994368A (enExample) |
| CH (1) | CH525197A (enExample) |
| DE (2) | DE2108727B2 (enExample) |
| FR (1) | FR2078961A5 (enExample) |
| GB (2) | GB1313812A (enExample) |
| IT (1) | IT994010B (enExample) |
| NL (2) | NL146154B (enExample) |
| SE (1) | SE374645B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12428372B2 (en) | 2022-04-14 | 2025-09-30 | Saudi Arabian Oil Company | ODSO acid medium, ODSO acid mixture medium, and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3686323A (en) * | 1970-02-24 | 1972-08-22 | Int Flavors & Fragrances Inc | Thioalkanal-s-oxides |
-
1971
- 1971-01-07 US US00104758A patent/US3751269A/en not_active Expired - Lifetime
- 1971-02-09 CA CA104,917A patent/CA994368A/en not_active Expired
- 1971-02-22 CH CH249871A patent/CH525197A/fr not_active IP Right Cessation
- 1971-02-22 IT IT48561/71A patent/IT994010B/it active
- 1971-02-23 FR FR7106114A patent/FR2078961A5/fr not_active Expired
- 1971-02-23 NL NL717102409A patent/NL146154B/xx unknown
- 1971-02-24 DE DE19712108727 patent/DE2108727B2/de not_active Withdrawn
- 1971-02-24 SE SE7102362A patent/SE374645B/xx unknown
- 1971-02-24 BE BE763403A patent/BE763403A/xx unknown
- 1971-02-24 DE DE2166074*A patent/DE2166074C3/de not_active Expired
- 1971-04-19 GB GB2403871*A patent/GB1313812A/en not_active Expired
- 1971-09-16 GB GB4314172A patent/GB1313813A/en not_active Expired
-
1974
- 1974-12-06 NL NL7415955A patent/NL7415955A/xx not_active Application Discontinuation
-
1975
- 1975-03-12 JP JP50030002A patent/JPS5113129B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US3751269A (en) | 1973-08-07 |
| NL146154B (nl) | 1975-06-16 |
| DE2166074A1 (de) | 1972-10-19 |
| NL7102409A (enExample) | 1971-08-26 |
| IT994010B (it) | 1975-10-20 |
| FR2078961A5 (enExample) | 1971-11-05 |
| BE763403A (fr) | 1971-08-24 |
| CA994368A (en) | 1976-08-03 |
| DE2108727A1 (de) | 1971-09-16 |
| CH525197A (fr) | 1972-07-15 |
| GB1313813A (en) | 1973-04-18 |
| DE2166074C3 (de) | 1975-05-28 |
| DE2166074B2 (de) | 1974-08-15 |
| SE374645B (enExample) | 1975-03-17 |
| GB1313812A (en) | 1973-04-18 |
| JPS5113129B2 (enExample) | 1976-04-26 |
| NL7415955A (nl) | 1975-03-27 |
| JPS50135030A (enExample) | 1975-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BHJ | Nonpayment of the annual fee |