DE2166074C3 - 07.01.71 USA 104758 Propylpropenylthiosulfonat dessen Herstellung und ein dieses enthaltendes Würzmittel - Google Patents
07.01.71 USA 104758 Propylpropenylthiosulfonat dessen Herstellung und ein dieses enthaltendes WürzmittelInfo
- Publication number
- DE2166074C3 DE2166074C3 DE2166074*A DE2166074A DE2166074C3 DE 2166074 C3 DE2166074 C3 DE 2166074C3 DE 2166074 A DE2166074 A DE 2166074A DE 2166074 C3 DE2166074 C3 DE 2166074C3
- Authority
- DE
- Germany
- Prior art keywords
- propylpropenylthiosulfonate
- onion
- taste
- reaction
- usa
- 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
- PRDGAWNUCKTNJV-UHFFFAOYSA-N oxo-prop-1-enyl-propoxy-sulfanylidene-$l^{6}-sulfane Chemical compound CCCOS(=O)(=S)C=CC PRDGAWNUCKTNJV-UHFFFAOYSA-N 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 235000011194 food seasoning agent Nutrition 0.000 title description 10
- 235000002732 Allium cepa var. cepa Nutrition 0.000 claims description 19
- 239000000796 flavoring agent Substances 0.000 claims description 8
- 235000019634 flavors Nutrition 0.000 claims description 8
- 240000006108 Allium ampeloprasum Species 0.000 claims description 5
- 235000005254 Allium ampeloprasum Nutrition 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- AAPBYIVJOWCMGH-UHFFFAOYSA-N 1-(prop-1-enyldisulfanyl)propane Chemical compound CCCSSC=CC AAPBYIVJOWCMGH-UHFFFAOYSA-N 0.000 claims description 3
- 239000012429 reaction media Substances 0.000 claims description 3
- 235000013409 condiments Nutrition 0.000 claims description 2
- 244000291564 Allium cepa Species 0.000 claims 1
- 241000234282 Allium Species 0.000 description 18
- 235000019640 taste Nutrition 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- -1 alkylidene sulfoxides Chemical class 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 235000015278 beef Nutrition 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000012084 conversion product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004278 EU approved seasoning Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- 239000002085 irritant Substances 0.000 description 2
- 231100000021 irritant Toxicity 0.000 description 2
- 235000013372 meat Nutrition 0.000 description 2
- 235000021201 onion's soup Nutrition 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 240000002234 Allium sativum Species 0.000 description 1
- NWJNYRPZCCCBMQ-UHFFFAOYSA-N CCCC(OS(=O)=S)=CC Chemical compound CCCC(OS(=O)=S)=CC NWJNYRPZCCCBMQ-UHFFFAOYSA-N 0.000 description 1
- BTYJOAGCBJQFNL-UHFFFAOYSA-N CO[S+]=S Chemical class CO[S+]=S BTYJOAGCBJQFNL-UHFFFAOYSA-N 0.000 description 1
- 101100327917 Caenorhabditis elegans chup-1 gene Proteins 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- 206010013911 Dysgeusia Diseases 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000013361 beverage Nutrition 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 230000000504 effect on taste Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000005454 flavour additive Substances 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 235000004611 garlic Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000008960 ketchup Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000003921 oil Substances 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
- 150000002978 peroxides Chemical class 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 235000015504 ready meals Nutrition 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- JTNXQVCPQMQLHK-UHFFFAOYSA-N thioacetone Chemical compound CC(C)=S JTNXQVCPQMQLHK-UHFFFAOYSA-N 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 (3)
| Publication Number | Publication Date |
|---|---|
| DE2166074A1 DE2166074A1 (de) | 1972-10-19 |
| DE2166074B2 DE2166074B2 (de) | 1974-08-15 |
| DE2166074C3 true DE2166074C3 (de) | 1975-05-28 |
Family
ID=26685289
Family Applications (2)
| 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 |
| DE19712108727 Withdrawn DE2108727B2 (de) | 1970-02-24 | 1971-02-24 | Alkylidensulfoxide, verfahren zu deren herstellung und wuerzmittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712108727 Withdrawn DE2108727B2 (de) | 1970-02-24 | 1971-02-24 | Alkylidensulfoxide, verfahren zu deren herstellung und wuerzmittel |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3751269A (https=) |
| JP (1) | JPS5113129B2 (https=) |
| BE (1) | BE763403A (https=) |
| CA (1) | CA994368A (https=) |
| CH (1) | CH525197A (https=) |
| DE (2) | DE2166074C3 (https=) |
| FR (1) | FR2078961A5 (https=) |
| GB (2) | GB1313812A (https=) |
| IT (1) | IT994010B (https=) |
| NL (2) | NL146154B (https=) |
| SE (1) | SE374645B (https=) |
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 BE BE763403A patent/BE763403A/xx unknown
- 1971-02-24 DE DE2166074*A patent/DE2166074C3/de not_active Expired
- 1971-02-24 DE DE19712108727 patent/DE2108727B2/de not_active Withdrawn
- 1971-02-24 SE SE7102362A patent/SE374645B/xx unknown
- 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 |
|---|---|
| JPS5113129B2 (https=) | 1976-04-26 |
| CA994368A (en) | 1976-08-03 |
| NL7415955A (nl) | 1975-03-27 |
| IT994010B (it) | 1975-10-20 |
| BE763403A (fr) | 1971-08-24 |
| US3751269A (en) | 1973-08-07 |
| DE2108727B2 (de) | 1973-08-16 |
| DE2166074B2 (de) | 1974-08-15 |
| NL7102409A (https=) | 1971-08-26 |
| FR2078961A5 (https=) | 1971-11-05 |
| GB1313812A (en) | 1973-04-18 |
| JPS50135030A (https=) | 1975-10-25 |
| DE2166074A1 (de) | 1972-10-19 |
| GB1313813A (en) | 1973-04-18 |
| DE2108727A1 (de) | 1971-09-16 |
| SE374645B (https=) | 1975-03-17 |
| CH525197A (fr) | 1972-07-15 |
| NL146154B (nl) | 1975-06-16 |
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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 | ||
| EHJ | Ceased/non-payment of the annual fee |