CA1091082A - Use of alkyl thiazoles as flavor additives - Google Patents
Use of alkyl thiazoles as flavor additivesInfo
- Publication number
- CA1091082A CA1091082A CA294,525A CA294525A CA1091082A CA 1091082 A CA1091082 A CA 1091082A CA 294525 A CA294525 A CA 294525A CA 1091082 A CA1091082 A CA 1091082A
- Authority
- CA
- Canada
- Prior art keywords
- flavor
- isopropyl
- thiazole
- alkyl
- parts
- 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
- 235000013355 food flavoring agent Nutrition 0.000 title abstract description 4
- -1 alkyl thiazoles Chemical class 0.000 title description 4
- OFLXNHNYPQPQKW-UHFFFAOYSA-N 2-isopropyl-4-methylthiazole Chemical compound CC(C)C1=NC(C)=CS1 OFLXNHNYPQPQKW-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000796 flavoring agent Substances 0.000 claims description 16
- 235000019634 flavors Nutrition 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 4
- 239000008369 fruit flavor Substances 0.000 abstract description 6
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract description 3
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 230000003116 impacting effect Effects 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000006040 Prunus persica var persica Nutrition 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 235000013399 edible fruits Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 244000144730 Amygdalus persica Species 0.000 description 5
- 240000000560 Citrus x paradisi Species 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- USVCRBGYQRVTNK-UHFFFAOYSA-N 1-Mercapto-2-propanone Chemical compound CC(=O)CS USVCRBGYQRVTNK-UHFFFAOYSA-N 0.000 description 2
- GDYKEHYOOVICQZ-UHFFFAOYSA-N 4,5-dimethyl-2-(1-methylethyl)thiazole Chemical compound CC(C)C1=NC(C)=C(C)S1 GDYKEHYOOVICQZ-UHFFFAOYSA-N 0.000 description 2
- RSSCOFSBIBEMBM-UHFFFAOYSA-N 4-methyl-2-propan-2-yl-2,5-dihydro-1,3-thiazole Chemical compound CC(C)C1SCC(C)=N1 RSSCOFSBIBEMBM-UHFFFAOYSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000019502 Orange oil Nutrition 0.000 description 2
- 240000005809 Prunus persica Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- YLYBTZIQSIBWLI-UHFFFAOYSA-N octyl acetate Chemical compound CCCCCCCCOC(C)=O YLYBTZIQSIBWLI-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- AYEGWZGUAQDVNB-UHFFFAOYSA-N 5-ethyl-4-methyl-2-(1-methylethyl)thiazole Chemical compound CCC=1SC(C(C)C)=NC=1C AYEGWZGUAQDVNB-UHFFFAOYSA-N 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 239000004097 EU approved flavor enhancer Substances 0.000 description 1
- 101000913968 Ipomoea purpurea Chalcone synthase C Proteins 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 101000907988 Petunia hybrida Chalcone-flavanone isomerase C Proteins 0.000 description 1
- 244000236580 Psidium pyriferum Species 0.000 description 1
- 240000001890 Ribes hudsonianum Species 0.000 description 1
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 1
- 235000001466 Ribes nigrum Nutrition 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000021554 flavoured beverage Nutrition 0.000 description 1
- 235000019264 food flavour enhancer Nutrition 0.000 description 1
- 235000021022 fresh fruits Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000014594 pastries Nutrition 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A23L27/2056—Heterocyclic compounds having at least two different hetero atoms, at least one being a nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/10—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Seasonings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Non-Alcoholic Beverages (AREA)
- Storage Of Fruits Or Vegetables (AREA)
- Confectionery (AREA)
- Preparation Of Fruits And Vegetables (AREA)
- Grain Derivatives (AREA)
- Medicines Containing Plant Substances (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4021/77 | 1977-02-01 | ||
| GB4021/77A GB1557382A (en) | 1977-02-01 | 1977-02-01 | Use of alkyl thiayoles as flavour additives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1091082A true CA1091082A (en) | 1980-12-09 |
Family
ID=9769249
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA294,525A Expired CA1091082A (en) | 1977-02-01 | 1978-01-09 | Use of alkyl thiazoles as flavor additives |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS53118556A (enExample) |
| AU (1) | AU511483B2 (enExample) |
| BE (1) | BE863527A (enExample) |
| CA (1) | CA1091082A (enExample) |
| CH (1) | CH627053A5 (enExample) |
| DE (1) | DE2804077C2 (enExample) |
| FR (1) | FR2378457B1 (enExample) |
| GB (1) | GB1557382A (enExample) |
| IL (1) | IL53937A0 (enExample) |
| IT (1) | IT1093585B (enExample) |
| NL (1) | NL189744C (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2404987B1 (en) * | 2009-03-06 | 2014-06-11 | Shiseido Co., Ltd. | Fragrance compositions |
| CN104177307B (zh) * | 2014-09-02 | 2016-10-05 | 北京工商大学 | 一种制备2-取代-4-甲基-3-噻唑啉类化合物的方法 |
| US20210198603A1 (en) * | 2018-02-23 | 2021-07-01 | Ava Food Labs, Inc. | Alcoholic beverages produced from individual components |
| CN115974811A (zh) * | 2023-01-10 | 2023-04-18 | 滕州市天水生物科技有限公司 | 一种2-异丙基-4-甲基噻唑的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3660112A (en) * | 1969-11-07 | 1972-05-02 | Campbell Soup Co | 2-alkylthiazoles as tomato product flavor enhancers |
| US3876652A (en) * | 1970-11-09 | 1975-04-08 | Int Flavors & Fragrances Inc | Certain 5-alkoxy-4-isobutylthiazoles |
| US3769040A (en) * | 1970-11-09 | 1973-10-30 | Int Flavors & Fragrances Inc | Substituted thiazoles in flavoring processes and products produced thereby |
| CH548116A (de) * | 1973-02-15 | 1974-04-11 | Siemens Ag Albis | Richtantennenanordnung fuer ein radargeraet. |
-
1977
- 1977-02-01 GB GB4021/77A patent/GB1557382A/en not_active Expired
-
1978
- 1978-01-09 CA CA294,525A patent/CA1091082A/en not_active Expired
- 1978-01-13 FR FR7800898A patent/FR2378457B1/fr not_active Expired
- 1978-01-27 NL NLAANVRAGE7801036,A patent/NL189744C/xx not_active IP Right Cessation
- 1978-01-27 AU AU32801/78A patent/AU511483B2/en not_active Expired
- 1978-01-31 DE DE2804077A patent/DE2804077C2/de not_active Expired
- 1978-01-31 IT IT19841/78A patent/IT1093585B/it active
- 1978-01-31 IL IL53937A patent/IL53937A0/xx not_active IP Right Cessation
- 1978-01-31 CH CH101278A patent/CH627053A5/fr not_active IP Right Cessation
- 1978-02-01 BE BE2056654A patent/BE863527A/xx not_active IP Right Cessation
- 1978-02-01 JP JP1037678A patent/JPS53118556A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2804077C2 (de) | 1987-01-15 |
| NL189744C (nl) | 1993-07-16 |
| JPS53118556A (en) | 1978-10-17 |
| NL189744B (nl) | 1993-02-16 |
| IL53937A0 (en) | 1978-04-30 |
| JPS637744B2 (enExample) | 1988-02-18 |
| FR2378457A1 (fr) | 1978-08-25 |
| DE2804077A1 (de) | 1978-08-03 |
| IT7819841A0 (it) | 1978-01-31 |
| AU3280178A (en) | 1979-08-02 |
| FR2378457B1 (fr) | 1985-06-21 |
| NL7801036A (nl) | 1978-08-03 |
| AU511483B2 (en) | 1980-08-21 |
| IT1093585B (it) | 1985-07-19 |
| GB1557382A (en) | 1979-12-12 |
| BE863527A (nl) | 1978-08-01 |
| CH627053A5 (en) | 1981-12-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |