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
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 COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- 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)
- Preparation Of Fruits And Vegetables (AREA)
- Storage Of Fruits Or Vegetables (AREA)
- Confectionery (AREA)
- Grain Derivatives (AREA)
- Non-Alcoholic Beverages (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Fats And Perfumes (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
ALKYL THIAZOLES AS FLAVOR ADDITIVES
Abstract of the Disclosure 2-Isopropyl-4methyl thiazole has been found useful in impacting or enhancing fruit flavors to foodstuffs.
Abstract of the Disclosure 2-Isopropyl-4methyl thiazole has been found useful in impacting or enhancing fruit flavors to foodstuffs.
Description
~icneL Case 3 "- l(J910~:
This invention relates to the use of a specific alkyl thiazole as a flavor additive to impart a fruit flavor to an otherwise non-$ruity, edible material or to enhance a fruit flavor which is already present in a foodstuff.
The compound o~ this invention is 2-isopropyl-4-methyl thiazole having the formula CH -C - N
3 ~
H - C C-CH-CH
, \ / I
The thiazole useful in the present invention is not per se novel. Thus, 2-isopropyl-4,5-dimethyl thiazole and
This invention relates to the use of a specific alkyl thiazole as a flavor additive to impart a fruit flavor to an otherwise non-$ruity, edible material or to enhance a fruit flavor which is already present in a foodstuff.
The compound o~ this invention is 2-isopropyl-4-methyl thiazole having the formula CH -C - N
3 ~
H - C C-CH-CH
, \ / I
The thiazole useful in the present invention is not per se novel. Thus, 2-isopropyl-4,5-dimethyl thiazole and
2-isopropyl-4-methyl-5-ethyl thiazole have been found in potatoes.
The 2-isopropyl-4-methyl thiazole has been identified in roast meat extract. Additionally, U.S. patent 3,769,040, Swiss patent 548,166 and-German D.T. ~,262,471 have shown various other alkyl thiazoles as additives for beverages such as coffee and cocoa, meat products, soup, vegetable and cereals. They are even said to be useful as flavor addltives for tobacco. U.S. patent
The 2-isopropyl-4-methyl thiazole has been identified in roast meat extract. Additionally, U.S. patent 3,769,040, Swiss patent 548,166 and-German D.T. ~,262,471 have shown various other alkyl thiazoles as additives for beverages such as coffee and cocoa, meat products, soup, vegetable and cereals. They are even said to be useful as flavor addltives for tobacco. U.S. patent
3,660,112 teaches that 2-alkyl thiazoles (3 carbon alkyl and up) are useful as tomato flavor enhancers.
In accordance with this invention it has been found that the addition of 2-isopropy-4-methyl thiazole causes significant and highly desirable improvement or enhancement o~ fruit flavors, and in particular, peach flavor. This additive is also use~ul for the enhancement of grape, guave, black currant, grapefruit and other fruit and berry flavors.
The amount o~ 2-isopropyl-4-methyl thiazole added to a foodstuff need be only the amount sufficient to impart or enhance `l~ the desired fruit flavor. Small amounts are effective, though , the amount can be varied over a wide range depending upon the flavor strength sought. The use o~ too great an amount is, of course, economically undesirable and in some cases can unbalance - 2 - ~
~ .. .
.` 10910~
the ~lavor and aroma, thus leading to less than optimum results.
Generally, the amount will be between about 0.0001 to about 5~ by weight based on the foodstuff being flavored.
The novel flavoring agent of this invention can be em-ployed to enhance the fruit tlavor ot various foodstuffs such as, e.g., fruit juices or fruit flavored beverages, puddings, pastries and ice cream. It can also be employed to enhance the fresh fruit effect of canned and frozen fruits such as, in particular, canned peaches.
It is very surprising to find that this compound, not known to be present in fruits naturally, but known to be present in materials having flavors totally different from fruits, could be used to enhance fruit flavors.
Although the alkyl thiazole employed in this invention is naturally occurring and can be isolated from its natural environ-ment, it is normally more convenient to prepare it synthetically.
This is accomplished by known methods, e.g., 2-isopropyl-4-methyl thiazole can be prepared by reacting mercaptoacetone with iso-butyraldehyde in the presence of ammonia followed by oxidation of the resulting thiazolidine to the thiazole.
Example 1 A. Preparation of 2,5-DihYdro-2-isopropyl-4-methyl Thiazole A solution of ~00 g. (5.0 moles) of sodium hydroxide in 800 ml. of water was charged to a four-nec~ed 3000 ml. round-bottomed flask provided with a mechanical stirrer, dropping funnel, thermometer, gas inlet tube and gas outlet tube. The ; flask was cooIed to 0C. At that temperature the solution was saturated with hydrogen sulfide and subsequently 416 G. (4.5 moles) of chloroacetone was added in a slow current over ~0 minutes. After the addition, stirring was continued for 2 hours. The li~uid layer was decanted and to the crude solid mercaptoacetone ~dimer) was added 1000 ml. of water and 302 g.
- lV911)t~;~
(4.2 moles) oL isobutyraldehyde. Gaseous a~monia was introduced into the mixture for about 8 hours. During this time, the reac-tion temperature was allowed to reach 60-70C. At the end of the reaction, the temperature was about 25C. The oily layer was separated and the water layer was extracted twice with 500 ml.
of water and dried over anhydrous sodium sulfate. The title compound (460 g.) was distilled at 70-72C. at 12 mm. Hg.
refractive index at 20 1.4948.
B. Preparation of 2-Isopropyl-4-methyl Thiazole A solution of 43 9. of para-chloranil in 2500 ml. ot absolute benzene was charged to a four-necked 4000 ml. round-bottomed flask provided with a mechanical stirrer, dropping funnel, thermometer and reflux condenser. The mixture was heated to reflux temperature and at that temperature, 250 g. (1.75 moles) of 2,5-dihydro-2-isopropyl-4-methyl thiazole was added over a 30 minute period. After the addition, the mixture was refluxed for 3 hours. The cooled reaction mixture was poured into 2500 ml. of a 5% sodium hydroxide solution. The organic layer was separated and the water layer was extracted 3 times Z0 with 500 ml. of benzene. The combined extracts were washed with 300 ml. of a 5~ sodium hydroxide solution and dried over anhydrous sodium sulfate. The title compound (197 g.) was distilled at 56-57C.- at 12 mm. Hg., refractive index at 20 ~ 1,4989.
-I Example 2 . f ' f ' Grapefruit Flavor Grapefruit flavor 60 parts Ethyl butyrate 8 parts Ethyl acetate 4 parts Lemon oi] 8 parts Orange oil 8 parts Ethyl alcohol 12 parts 1091(~H;~
When about 0.05 to 0.5 part o~ 2-isopropyl-4-methyl thiazole is added to the above grapefruit flavor, a well-roùnded, more juicy and peel-like flavor is obtained. When this flavor is added to a 15~ sugar solution in water, a good tasting, peely, juicy grapefruit taste is obtained.
Example 3 Peach Flavor delta-Decalactone 5.0 parts Ethyl acetate 50.0 parts Orange oil 2.5 parts Linalool 2.5 parts Octyl acetate 2.5 parts Caproic acid 2.5 parts Ethyl alcohol 35.0 parts i When 0.05 to 0.4 part of 2-isopropyl-4-methyl thiazole is added to the above peach flavor, a peach skin note is imparted and a generally nice fresh peach flavor is obtained. A 15~ sugar solution containing 0.25% of the flavor, which includes the 2-isopropyl-4-methyl thiazole, was made and tested. A fresh, well rounded peach taste was obtained.
In accordance with this invention it has been found that the addition of 2-isopropy-4-methyl thiazole causes significant and highly desirable improvement or enhancement o~ fruit flavors, and in particular, peach flavor. This additive is also use~ul for the enhancement of grape, guave, black currant, grapefruit and other fruit and berry flavors.
The amount o~ 2-isopropyl-4-methyl thiazole added to a foodstuff need be only the amount sufficient to impart or enhance `l~ the desired fruit flavor. Small amounts are effective, though , the amount can be varied over a wide range depending upon the flavor strength sought. The use o~ too great an amount is, of course, economically undesirable and in some cases can unbalance - 2 - ~
~ .. .
.` 10910~
the ~lavor and aroma, thus leading to less than optimum results.
Generally, the amount will be between about 0.0001 to about 5~ by weight based on the foodstuff being flavored.
The novel flavoring agent of this invention can be em-ployed to enhance the fruit tlavor ot various foodstuffs such as, e.g., fruit juices or fruit flavored beverages, puddings, pastries and ice cream. It can also be employed to enhance the fresh fruit effect of canned and frozen fruits such as, in particular, canned peaches.
It is very surprising to find that this compound, not known to be present in fruits naturally, but known to be present in materials having flavors totally different from fruits, could be used to enhance fruit flavors.
Although the alkyl thiazole employed in this invention is naturally occurring and can be isolated from its natural environ-ment, it is normally more convenient to prepare it synthetically.
This is accomplished by known methods, e.g., 2-isopropyl-4-methyl thiazole can be prepared by reacting mercaptoacetone with iso-butyraldehyde in the presence of ammonia followed by oxidation of the resulting thiazolidine to the thiazole.
Example 1 A. Preparation of 2,5-DihYdro-2-isopropyl-4-methyl Thiazole A solution of ~00 g. (5.0 moles) of sodium hydroxide in 800 ml. of water was charged to a four-nec~ed 3000 ml. round-bottomed flask provided with a mechanical stirrer, dropping funnel, thermometer, gas inlet tube and gas outlet tube. The ; flask was cooIed to 0C. At that temperature the solution was saturated with hydrogen sulfide and subsequently 416 G. (4.5 moles) of chloroacetone was added in a slow current over ~0 minutes. After the addition, stirring was continued for 2 hours. The li~uid layer was decanted and to the crude solid mercaptoacetone ~dimer) was added 1000 ml. of water and 302 g.
- lV911)t~;~
(4.2 moles) oL isobutyraldehyde. Gaseous a~monia was introduced into the mixture for about 8 hours. During this time, the reac-tion temperature was allowed to reach 60-70C. At the end of the reaction, the temperature was about 25C. The oily layer was separated and the water layer was extracted twice with 500 ml.
of water and dried over anhydrous sodium sulfate. The title compound (460 g.) was distilled at 70-72C. at 12 mm. Hg.
refractive index at 20 1.4948.
B. Preparation of 2-Isopropyl-4-methyl Thiazole A solution of 43 9. of para-chloranil in 2500 ml. ot absolute benzene was charged to a four-necked 4000 ml. round-bottomed flask provided with a mechanical stirrer, dropping funnel, thermometer and reflux condenser. The mixture was heated to reflux temperature and at that temperature, 250 g. (1.75 moles) of 2,5-dihydro-2-isopropyl-4-methyl thiazole was added over a 30 minute period. After the addition, the mixture was refluxed for 3 hours. The cooled reaction mixture was poured into 2500 ml. of a 5% sodium hydroxide solution. The organic layer was separated and the water layer was extracted 3 times Z0 with 500 ml. of benzene. The combined extracts were washed with 300 ml. of a 5~ sodium hydroxide solution and dried over anhydrous sodium sulfate. The title compound (197 g.) was distilled at 56-57C.- at 12 mm. Hg., refractive index at 20 ~ 1,4989.
-I Example 2 . f ' f ' Grapefruit Flavor Grapefruit flavor 60 parts Ethyl butyrate 8 parts Ethyl acetate 4 parts Lemon oi] 8 parts Orange oil 8 parts Ethyl alcohol 12 parts 1091(~H;~
When about 0.05 to 0.5 part o~ 2-isopropyl-4-methyl thiazole is added to the above grapefruit flavor, a well-roùnded, more juicy and peel-like flavor is obtained. When this flavor is added to a 15~ sugar solution in water, a good tasting, peely, juicy grapefruit taste is obtained.
Example 3 Peach Flavor delta-Decalactone 5.0 parts Ethyl acetate 50.0 parts Orange oil 2.5 parts Linalool 2.5 parts Octyl acetate 2.5 parts Caproic acid 2.5 parts Ethyl alcohol 35.0 parts i When 0.05 to 0.4 part of 2-isopropyl-4-methyl thiazole is added to the above peach flavor, a peach skin note is imparted and a generally nice fresh peach flavor is obtained. A 15~ sugar solution containing 0.25% of the flavor, which includes the 2-isopropyl-4-methyl thiazole, was made and tested. A fresh, well rounded peach taste was obtained.
Claims (2)
1. A flavoring composition comprising, in combination with other organoleptically active components, an amount effective to impart or enhance a fruity flavor of 2-isopropyl-4-methyl thiazole.
2. A foodstuff to which has been added about .0001 to 5% based on the total weight of said foodstuff of 2-isopropyl-4-methyl thiazole.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4021/77A GB1557382A (en) | 1977-02-01 | 1977-02-01 | Use of alkyl thiayoles as flavour additives |
| GB4021/77 | 1977-02-01 |
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 (en) |
| AU (1) | AU511483B2 (en) |
| BE (1) | BE863527A (en) |
| CA (1) | CA1091082A (en) |
| CH (1) | CH627053A5 (en) |
| DE (1) | DE2804077C2 (en) |
| FR (1) | FR2378457B1 (en) |
| GB (1) | GB1557382A (en) |
| IL (1) | IL53937A0 (en) |
| IT (1) | IT1093585B (en) |
| NL (1) | NL189744C (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102341488B (en) | 2009-03-06 | 2013-08-14 | 株式会社资生堂 | Fragrance compositions |
| CN104177307B (en) * | 2014-09-02 | 2016-10-05 | 北京工商大学 | A kind of method preparing 2-replacement-4-methyl-3-Thiazoling type compound |
| AU2019223096A1 (en) * | 2018-02-23 | 2020-09-17 | Ava Food Labs, Inc. | Alcoholic beverages produced from individual components |
| CN115974811A (en) * | 2023-01-10 | 2023-04-18 | 滕州市天水生物科技有限公司 | Preparation method of 2-isopropyl-4-methylthiazole |
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 |
| US3769040A (en) * | 1970-11-09 | 1973-10-30 | Int Flavors & Fragrances Inc | Substituted thiazoles in flavoring processes and products produced thereby |
| US3876652A (en) * | 1970-11-09 | 1975-04-08 | Int Flavors & Fragrances Inc | Certain 5-alkoxy-4-isobutylthiazoles |
| CH548116A (en) * | 1973-02-15 | 1974-04-11 | Siemens Ag Albis | DIRECTIONAL ANTENNA ARRANGEMENT FOR A RADAR UNIT. |
-
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/en not_active Expired
- 1978-01-27 AU AU32801/78A patent/AU511483B2/en not_active Expired
- 1978-01-27 NL NLAANVRAGE7801036,A patent/NL189744C/en not_active IP Right Cessation
- 1978-01-31 IL IL53937A patent/IL53937A0/en not_active IP Right Cessation
- 1978-01-31 DE DE2804077A patent/DE2804077C2/en not_active Expired
- 1978-01-31 CH CH101278A patent/CH627053A5/en not_active IP Right Cessation
- 1978-01-31 IT IT19841/78A patent/IT1093585B/en active
- 1978-02-01 BE BE2056654A patent/BE863527A/en not_active IP Right Cessation
- 1978-02-01 JP JP1037678A patent/JPS53118556A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS53118556A (en) | 1978-10-17 |
| AU3280178A (en) | 1979-08-02 |
| DE2804077C2 (en) | 1987-01-15 |
| DE2804077A1 (en) | 1978-08-03 |
| NL7801036A (en) | 1978-08-03 |
| NL189744B (en) | 1993-02-16 |
| AU511483B2 (en) | 1980-08-21 |
| NL189744C (en) | 1993-07-16 |
| FR2378457B1 (en) | 1985-06-21 |
| CH627053A5 (en) | 1981-12-31 |
| GB1557382A (en) | 1979-12-12 |
| IT7819841A0 (en) | 1978-01-31 |
| FR2378457A1 (en) | 1978-08-25 |
| IL53937A0 (en) | 1978-04-30 |
| JPS637744B2 (en) | 1988-02-18 |
| BE863527A (en) | 1978-08-01 |
| IT1093585B (en) | 1985-07-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |