CA1062269A - Flavoring compositions containing alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylates - Google Patents
Flavoring compositions containing alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylatesInfo
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- CA1062269A CA1062269A CA257,711A CA257711A CA1062269A CA 1062269 A CA1062269 A CA 1062269A CA 257711 A CA257711 A CA 257711A CA 1062269 A CA1062269 A CA 1062269A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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- 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
- A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
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- 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
- A23L27/29—Fruit flavours
-
- 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
- A23L27/30—Artificial sweetening agents
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
- A24B15/406—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms in a five-membered ring
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12G—WINE; PREPARATION THEREOF; ALCOHOLIC BEVERAGES; PREPARATION OF ALCOHOLIC BEVERAGES NOT PROVIDED FOR IN SUBCLASSES C12C OR C12H
- C12G3/00—Preparation of other alcoholic beverages
- C12G3/04—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs
- C12G3/06—Preparation of other alcoholic beverages by mixing, e.g. for preparation of liqueurs with flavouring ingredients
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- Food Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Toxicology (AREA)
- Wood Science & Technology (AREA)
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- Seasonings (AREA)
- Fats And Perfumes (AREA)
- Manufacture Of Tobacco Products (AREA)
- Furan Compounds (AREA)
- Confectionery (AREA)
Abstract
ABSTRACT
The flavor compositions of this invention include alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-s-alkyl-furan-4-carboxylates which significantly ?nhance the flavor component or components of flavor composition. For example, butter-scotch flavors are materially improved in smoothness and cer-tain fruit flavors are given greater richness and ripeness.
The flavor compositions of this invention include alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-s-alkyl-furan-4-carboxylates which significantly ?nhance the flavor component or components of flavor composition. For example, butter-scotch flavors are materially improved in smoothness and cer-tain fruit flavors are given greater richness and ripeness.
Description
~` 106ZZ69 Thi8 invention relates to flavor compo~itions and more par-ticularly to flavor compositions containing an alkyl-2,3-dihydro-3(1'hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate.
. . - .
It is well known that synthetic flavor enhancers such as Maltol, Ethyl Maltol, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone are useful as flavor enhancers. However, ~uch flavor enhancers are very expensive and increase the cost of pxoducts in which they are used.
In accordance with one feature of this invention, an alkyl-
. . - .
It is well known that synthetic flavor enhancers such as Maltol, Ethyl Maltol, and 4-hydroxy-2,5-dimethyl-3(2H)-furanone are useful as flavor enhancers. However, ~uch flavor enhancers are very expensive and increase the cost of pxoducts in which they are used.
In accordance with one feature of this invention, an alkyl-
2,3-dihydro-3(1'hydroxyalkylidene)-2-oxo-5-alkyl-~uran-4-carboxy-late is added to flavor components to impart a significantly en~
hanced flavor to a wide variety of flavor components. For exam-ple, butterscotch flavors are materially improved in smoothness.
Strawberry flavors are given a striking freshness. Banan~ flavors are rounded out to give the flavor of a ripe banana. When added to smoking tobacco or synthetic tobacco, the resulting product is increased in ~weetness, the taste of the smoke i~ softened and the -.
flow of saliva is increased, which lessens dryness of the mouth during smoking. When added to cough syrup containing theophyl-line, the flavor enhancer of this invention covers up the bitter taste. This flavor enhancer can also be used to replace part of the sugar content of a wide variety of sweetened beverages and foods, producing excellent flavor at lower cost.
Alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylates employed in the flavor compositions of this invention have the formula:
H
Rl O
., 0/
:.
in which Rl is a straight or branched chain alkyl having les~
than 6 carbon atoms, and R2 is a straight or branched chain alkyl having less than 7 carbon atoms, cyclopentyl or cyclo-hexyl.
Examples of Rl are methyl, ethyl, propyl, isopropyl, butyl, -isobutyl, amyl and isoamyl.
Examples of R2 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl or isohexyl.
Rl and R2 may be the same or different.
The alkyl-2,3-dihydro-3(1'hydroxyalkylidene)-2-oxo-5~alkyl-furan-4-carboxylates may be prepared by the general methods of Knorr, Ber. 1889, 22, 158.
The flavor compositions of this invention comprise at least 0.0025% by w~ight of one or more alkyl-2,3-dihydro-3(1'hydroxy-alkylidene)-2-oxo-5-alkyl-furan-4-carboxylates. The amount of alkyl-2,3-dihydro-3(1'hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate may vary within wide ranges such as 0.0001% to 30%
lO~;Z269 by weight. More advantageously the range may be between 0.001%
and 20% by weight of the flavor composition and preferably be-tween 0.0025% and 5% by weight of the flavor composition.
Examples of flavor components of the flavor compositions of this invention are flavor mixtures E~ se such as pineapple, butterscotch, banana, and strawberry; food~tuffs such as meats, protein sources, fruits, cereals and other comestibles; beverages such as soft drinks, wines, alcoholic drinks, carbonated beve-rages; smoking tobacco; liquid medicaments such as cough syrups;
and sugar substitutes in a wide range of edible or drinkable products.
In accordance with another feature of this invention, cer-tain alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylates are new and novel. Such new and novel car-boxylates significantly enhance the flavor components of the com-positions of this invention. The new and novel carboxylates have the following formula:
~ 1 fH
~, .. , . ,. R2-0 /--~ Rl in which Rl iB a straight or branched chain alkyl having more than 1 and less than 6 carbon atoms, and R2 is a straight or branched chain alkyl having more than 1 and less than 7 carbon atoms, cyclopentyl or cyclohexyl.
Examples of Rl are ethyl, propyl, isopropyl, butyl, iso-- butyl, amyl and i~oamyl.
Examples of R2 are ethyl, propyl, isobutyl, amyl, hexyl and cyclopentyl.
Rl and R2 may be the same or different.
, :
~.
.. - ., The new and novel carboxylates may be produced by the general method of KnorrJ Ber. 1889, 22, 158.
A more comprehensive understanding of this invention i8 obtained from the following examples. Examples I and II show compo~itions produced with two levels of concentration of ethyl-2,3-dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate.
EXAMPLE I
PINEAPPLE FLAVOR COMPOSITION
Parts by Parts by Weight Weiqht Allyl Cyclohexane Propionate 1.4 1.4 Geranyl Propionate 0.5 0.5 Allyl Caproate 13.0 13.0 Ethyl Iso Valerate 1.0 1.0 Ethyl Butyrate 1.0 1.0 Vanillin 0.5 0.5 Oil Orange 1.0 1.0 Maltol 2.0 2.0 Ethyl-2,3-Dihydro-3(1'-Hydroxyethylidene)-2-Oxo-5-Methyl-Furan-4-Carboxylate 20.0 2.5 Ethyl Alcohol 95% 46.0 46.0 Propylene Glycol 13.6 31.1 100.0100.0 .
10622~9 EXAMPLE II
STR~WBERRY FLAVOR COMPOSI~ION
Parts by Parts by Weiqht Weiaht Methoxy Phenyl Butanone 1.0 1.0 Ethyl Butyrate 6.0 6.0 Ethyl Iso Valerate 2.0 2.0 Benzyl Butyrate 1.5 1.5 Benzyl Iso Valerate 0.5 ' 0.5 cis-3-Hexenol 3 0 3 0 Isobutyric Acid 1.5 1.5 Diacetyl 0.2 0.2 Butyl Phenylacetate 0.4 0.4 Acetaldehyde 50% in Ethanol 0.2 0.2 Benzyl Dipropyl K~tone 0.2 0.2 2-Heptanone 0.1 0.1 Ethyl Methyl Phenyl Glycidate 2.4 2.4 Ethyl-2,3-Dihydro-3(1'-Hydroxyethylidene)-2-Oxo-5-Methyl-Furan-4-Carboxylate 30.0 5.0 Propylene Glycol 51.0 51.0 Benzyl Alaohol ~ 25.0 100.0 1~0.0 .~
~ . .
_ 5 _ .
EX~MPLE III
BUTTERSCOTCH FLAVOR COMPOSITION
Parts by Weiqht Ethyl-2,3-Dihydro-3(1'Hydroxyethylidene)-2-Oxo--S-Methyl-Furan-4--Carboxylate ~ 1.0 Butyl Butyrolaetate 4.0 Diacetyl 0.2 Ethyl Oleate 2.0 Ethyl Myristate o,5 Vanillin 1.5 Aeetoin 0~3 Phenylethanol 0.2 Butyric Acid 0.1 Ethyl Qxyhydrate 0.1 Ethyl Maltol 3,0 ~-Decalactone 0,3 ~-Nonalaetone 0.1 Tincture Foenugreek 0.4 Methyl Cyelopentene-ol-one 0.1 Benzyl Aleohol 26.0 Propylene Glyeol 60.2 100.0 .
, . . ~ .
.
EX~MPLE_IV
BANANA FLAVOR COMPOSITION
Parts by Weiqht Iso Amyl Acetate 12.0 Iso Amyl Butyrate , ! 10 . O
Benzyl Butyrate 3.0 Iso Amyl Iso Valerate 2~0 Ethyl Butyrate 3.0 Butyric Acid 1.5 Oil Lemon 2.5 Vanillin 2.5 :
Ethyl Maltol 0.5 ~-Undecalactone 0.4 4-~p-Hydroxyphenyl)-2-Butanone 0.1 Ethyl-2,3-Dihydro-3(1'Hydroxyethylidene)-2-Oxo-5-Methyl-Furan-4-Carboxylate 10.0 Propylene Glycol 52.5 100 . O
.' ' "', ..., -EX~MP~ V
BUTTERSCOTCH FLAVOR
VA VB
Butyl Butyrolactate 4.0 4.0 Diacetyl 0.2 0.2 Ethyl Oleate 2.0 2.0 Ethyl Myri~tate 0.5 0 5 Vanillin 1.5 1.5 Acetyl Methyl Carbinol 0.3 0.3 Phenyl Ethyl Alcohol 0.2 0.2 Butyric Acid 0.1 0.1 Ethyl Oxyhydrate 0.1 0.1 Ethyl Maltol 3.0 Ethyl-2,3-Dihydro-3(1'Hydroxyethylidene)-2-Oxo-5-Methyl-Furan-4-Carboxylate 1.0 5.0 Q-Decalactone 0.3 0.3 ~-Nonalactone 0.1 0.1 Tincture Foenugreek 0.4 0.4 Methyl cyclopenten-ol-one 0.1 0.1 Benzyl Alcohol 26.0 26.0 Propylene Glycol 60.2 59.2 100 . O 100 . O
Formula U~ contains Ethyl Maltol in addition to ethyl-2,3-dihydro-3(1'hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate, while Formula VB contains only the carboxylate as a complete re-placement for Ethyl Maltol. The butterscotch flavor achieved by Formula VB i6 richer and smoother.
The replacement proportion of Ethyl Maltol by ethyl-2,3- -dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate i8 approximately one and one-half part~ by weight of the carboxy-late for one part by weight of Ethyl Maltol.
.
10~2Z69 EXAMPLE VI
WINE FL~VOR COMPOS ITION
The wine flavor composition is produced by initially adding 0.08 parts by weight of ethyl-2,3-dihydro-3(1 hydroxyethylidene)-~ 2-oxo-5-methyl-furan-4-carboxylate to 99.92 parts by weight of ; natural wine flavor. Four liquid ounces of the wine concentrate are added to one gallon of wine.
A wine flavor composition may al~o be produced by preparing a 1% by weight ethanol solution of ethyl-2,3-dihydro-3(1'-hydroxy-ethylidene)-2-oxo-5-methyl-furan-4-carboxylate and adding 0.32 fluid ounces of the solution to 1 gallon of wine. This i8 equi-valent to 25 parts per million.
EX~MPLE VII
`, TOBACCO FL~VOR COMPOSITION
A 1% ethanol solution of ethyl-2,3-dihydro-3(1'hydroxyethy-lidene)-2-oxo-5-methyl-furan-4-carboxylate is sprayed on smoking tobaeco at the rate of 4 ounces of solution per 100 pounds of tobaeco. After the alcohol is allowed to evaporate, a tobacco flavor composition results.
To produee a flavored tobaceo whieh also eontains synthetie tobaeeo, the procedure for the production of tobacco flavor com-position heretofore described in this Example is repeated except that instead of employing -moking tobacco only, synthetic tobacco such as cellulose fibers, for example, the cellulose fibers sold by the Celanese Chemical Company under the trademark "CYTREL" or ! the eellulose fibers sold by Imperial Chemical Corporation under -the trademark "POLYSTREP", is blended with the flavored tobaceo in a ratio of approximately 1 to 1 by weight.
In a third proeedure, a 1% etha~ol solution of ethyl-2,3- -dihydro-3~ hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate _ g _ . ' ', .: ~.' ' ' 106226g is sprayed on synthetic tobacco, such as cellulose fibers, at the rate of 4 ounces of solution to 100 pounds of synthetie tobacco. After the alcohol is allowed to evaporate, a tobaeeo flavor synthetic composition results.
Any one of the above tobacco flavor eompositions may be used in cigarettes, producing a striking improvement in flavor.
` Experiments were conducted with panatela cigars using ethyl-2,3-dihydro-3(1'-hydroxyisopentylidene)-2-oxo-5-isobutyl-furan-4-carboxylate as the flavor enhaneer in 95% ethanol at the rate of 1.5 ounces of enhaneer to 100 pounds of panatela eigars.
The aroma and flavor of the smoke were signifieantly improved.
';
EXAMPLE VIII
-~ CARBONATED SOFT DRINKS
., _ A fruit flavor earbonated soft drink is produeed by dissol-ving one ounee by weight of one of the flavor eompositions sueh 2` as deseribed in Examples I or II in one gallon of sugar syrup.
One ounee of the resulting mixture is added to about five ounees of earbonated water to produee six ounees of earbonated beverage.
`~ ' ' The flavor eompo~ition eontaining 2.5% by weight of ethyl-2,
hanced flavor to a wide variety of flavor components. For exam-ple, butterscotch flavors are materially improved in smoothness.
Strawberry flavors are given a striking freshness. Banan~ flavors are rounded out to give the flavor of a ripe banana. When added to smoking tobacco or synthetic tobacco, the resulting product is increased in ~weetness, the taste of the smoke i~ softened and the -.
flow of saliva is increased, which lessens dryness of the mouth during smoking. When added to cough syrup containing theophyl-line, the flavor enhancer of this invention covers up the bitter taste. This flavor enhancer can also be used to replace part of the sugar content of a wide variety of sweetened beverages and foods, producing excellent flavor at lower cost.
Alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylates employed in the flavor compositions of this invention have the formula:
H
Rl O
., 0/
:.
in which Rl is a straight or branched chain alkyl having les~
than 6 carbon atoms, and R2 is a straight or branched chain alkyl having less than 7 carbon atoms, cyclopentyl or cyclo-hexyl.
Examples of Rl are methyl, ethyl, propyl, isopropyl, butyl, -isobutyl, amyl and isoamyl.
Examples of R2 are methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, isoamyl, hexyl or isohexyl.
Rl and R2 may be the same or different.
The alkyl-2,3-dihydro-3(1'hydroxyalkylidene)-2-oxo-5~alkyl-furan-4-carboxylates may be prepared by the general methods of Knorr, Ber. 1889, 22, 158.
The flavor compositions of this invention comprise at least 0.0025% by w~ight of one or more alkyl-2,3-dihydro-3(1'hydroxy-alkylidene)-2-oxo-5-alkyl-furan-4-carboxylates. The amount of alkyl-2,3-dihydro-3(1'hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate may vary within wide ranges such as 0.0001% to 30%
lO~;Z269 by weight. More advantageously the range may be between 0.001%
and 20% by weight of the flavor composition and preferably be-tween 0.0025% and 5% by weight of the flavor composition.
Examples of flavor components of the flavor compositions of this invention are flavor mixtures E~ se such as pineapple, butterscotch, banana, and strawberry; food~tuffs such as meats, protein sources, fruits, cereals and other comestibles; beverages such as soft drinks, wines, alcoholic drinks, carbonated beve-rages; smoking tobacco; liquid medicaments such as cough syrups;
and sugar substitutes in a wide range of edible or drinkable products.
In accordance with another feature of this invention, cer-tain alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylates are new and novel. Such new and novel car-boxylates significantly enhance the flavor components of the com-positions of this invention. The new and novel carboxylates have the following formula:
~ 1 fH
~, .. , . ,. R2-0 /--~ Rl in which Rl iB a straight or branched chain alkyl having more than 1 and less than 6 carbon atoms, and R2 is a straight or branched chain alkyl having more than 1 and less than 7 carbon atoms, cyclopentyl or cyclohexyl.
Examples of Rl are ethyl, propyl, isopropyl, butyl, iso-- butyl, amyl and i~oamyl.
Examples of R2 are ethyl, propyl, isobutyl, amyl, hexyl and cyclopentyl.
Rl and R2 may be the same or different.
, :
~.
.. - ., The new and novel carboxylates may be produced by the general method of KnorrJ Ber. 1889, 22, 158.
A more comprehensive understanding of this invention i8 obtained from the following examples. Examples I and II show compo~itions produced with two levels of concentration of ethyl-2,3-dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate.
EXAMPLE I
PINEAPPLE FLAVOR COMPOSITION
Parts by Parts by Weight Weiqht Allyl Cyclohexane Propionate 1.4 1.4 Geranyl Propionate 0.5 0.5 Allyl Caproate 13.0 13.0 Ethyl Iso Valerate 1.0 1.0 Ethyl Butyrate 1.0 1.0 Vanillin 0.5 0.5 Oil Orange 1.0 1.0 Maltol 2.0 2.0 Ethyl-2,3-Dihydro-3(1'-Hydroxyethylidene)-2-Oxo-5-Methyl-Furan-4-Carboxylate 20.0 2.5 Ethyl Alcohol 95% 46.0 46.0 Propylene Glycol 13.6 31.1 100.0100.0 .
10622~9 EXAMPLE II
STR~WBERRY FLAVOR COMPOSI~ION
Parts by Parts by Weiqht Weiaht Methoxy Phenyl Butanone 1.0 1.0 Ethyl Butyrate 6.0 6.0 Ethyl Iso Valerate 2.0 2.0 Benzyl Butyrate 1.5 1.5 Benzyl Iso Valerate 0.5 ' 0.5 cis-3-Hexenol 3 0 3 0 Isobutyric Acid 1.5 1.5 Diacetyl 0.2 0.2 Butyl Phenylacetate 0.4 0.4 Acetaldehyde 50% in Ethanol 0.2 0.2 Benzyl Dipropyl K~tone 0.2 0.2 2-Heptanone 0.1 0.1 Ethyl Methyl Phenyl Glycidate 2.4 2.4 Ethyl-2,3-Dihydro-3(1'-Hydroxyethylidene)-2-Oxo-5-Methyl-Furan-4-Carboxylate 30.0 5.0 Propylene Glycol 51.0 51.0 Benzyl Alaohol ~ 25.0 100.0 1~0.0 .~
~ . .
_ 5 _ .
EX~MPLE III
BUTTERSCOTCH FLAVOR COMPOSITION
Parts by Weiqht Ethyl-2,3-Dihydro-3(1'Hydroxyethylidene)-2-Oxo--S-Methyl-Furan-4--Carboxylate ~ 1.0 Butyl Butyrolaetate 4.0 Diacetyl 0.2 Ethyl Oleate 2.0 Ethyl Myristate o,5 Vanillin 1.5 Aeetoin 0~3 Phenylethanol 0.2 Butyric Acid 0.1 Ethyl Qxyhydrate 0.1 Ethyl Maltol 3,0 ~-Decalactone 0,3 ~-Nonalaetone 0.1 Tincture Foenugreek 0.4 Methyl Cyelopentene-ol-one 0.1 Benzyl Aleohol 26.0 Propylene Glyeol 60.2 100.0 .
, . . ~ .
.
EX~MPLE_IV
BANANA FLAVOR COMPOSITION
Parts by Weiqht Iso Amyl Acetate 12.0 Iso Amyl Butyrate , ! 10 . O
Benzyl Butyrate 3.0 Iso Amyl Iso Valerate 2~0 Ethyl Butyrate 3.0 Butyric Acid 1.5 Oil Lemon 2.5 Vanillin 2.5 :
Ethyl Maltol 0.5 ~-Undecalactone 0.4 4-~p-Hydroxyphenyl)-2-Butanone 0.1 Ethyl-2,3-Dihydro-3(1'Hydroxyethylidene)-2-Oxo-5-Methyl-Furan-4-Carboxylate 10.0 Propylene Glycol 52.5 100 . O
.' ' "', ..., -EX~MP~ V
BUTTERSCOTCH FLAVOR
VA VB
Butyl Butyrolactate 4.0 4.0 Diacetyl 0.2 0.2 Ethyl Oleate 2.0 2.0 Ethyl Myri~tate 0.5 0 5 Vanillin 1.5 1.5 Acetyl Methyl Carbinol 0.3 0.3 Phenyl Ethyl Alcohol 0.2 0.2 Butyric Acid 0.1 0.1 Ethyl Oxyhydrate 0.1 0.1 Ethyl Maltol 3.0 Ethyl-2,3-Dihydro-3(1'Hydroxyethylidene)-2-Oxo-5-Methyl-Furan-4-Carboxylate 1.0 5.0 Q-Decalactone 0.3 0.3 ~-Nonalactone 0.1 0.1 Tincture Foenugreek 0.4 0.4 Methyl cyclopenten-ol-one 0.1 0.1 Benzyl Alcohol 26.0 26.0 Propylene Glycol 60.2 59.2 100 . O 100 . O
Formula U~ contains Ethyl Maltol in addition to ethyl-2,3-dihydro-3(1'hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate, while Formula VB contains only the carboxylate as a complete re-placement for Ethyl Maltol. The butterscotch flavor achieved by Formula VB i6 richer and smoother.
The replacement proportion of Ethyl Maltol by ethyl-2,3- -dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate i8 approximately one and one-half part~ by weight of the carboxy-late for one part by weight of Ethyl Maltol.
.
10~2Z69 EXAMPLE VI
WINE FL~VOR COMPOS ITION
The wine flavor composition is produced by initially adding 0.08 parts by weight of ethyl-2,3-dihydro-3(1 hydroxyethylidene)-~ 2-oxo-5-methyl-furan-4-carboxylate to 99.92 parts by weight of ; natural wine flavor. Four liquid ounces of the wine concentrate are added to one gallon of wine.
A wine flavor composition may al~o be produced by preparing a 1% by weight ethanol solution of ethyl-2,3-dihydro-3(1'-hydroxy-ethylidene)-2-oxo-5-methyl-furan-4-carboxylate and adding 0.32 fluid ounces of the solution to 1 gallon of wine. This i8 equi-valent to 25 parts per million.
EX~MPLE VII
`, TOBACCO FL~VOR COMPOSITION
A 1% ethanol solution of ethyl-2,3-dihydro-3(1'hydroxyethy-lidene)-2-oxo-5-methyl-furan-4-carboxylate is sprayed on smoking tobaeco at the rate of 4 ounces of solution per 100 pounds of tobaeco. After the alcohol is allowed to evaporate, a tobacco flavor composition results.
To produee a flavored tobaceo whieh also eontains synthetie tobaeeo, the procedure for the production of tobacco flavor com-position heretofore described in this Example is repeated except that instead of employing -moking tobacco only, synthetic tobacco such as cellulose fibers, for example, the cellulose fibers sold by the Celanese Chemical Company under the trademark "CYTREL" or ! the eellulose fibers sold by Imperial Chemical Corporation under -the trademark "POLYSTREP", is blended with the flavored tobaceo in a ratio of approximately 1 to 1 by weight.
In a third proeedure, a 1% etha~ol solution of ethyl-2,3- -dihydro-3~ hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate _ g _ . ' ', .: ~.' ' ' 106226g is sprayed on synthetic tobacco, such as cellulose fibers, at the rate of 4 ounces of solution to 100 pounds of synthetie tobacco. After the alcohol is allowed to evaporate, a tobaeeo flavor synthetic composition results.
Any one of the above tobacco flavor eompositions may be used in cigarettes, producing a striking improvement in flavor.
` Experiments were conducted with panatela cigars using ethyl-2,3-dihydro-3(1'-hydroxyisopentylidene)-2-oxo-5-isobutyl-furan-4-carboxylate as the flavor enhaneer in 95% ethanol at the rate of 1.5 ounces of enhaneer to 100 pounds of panatela eigars.
The aroma and flavor of the smoke were signifieantly improved.
';
EXAMPLE VIII
-~ CARBONATED SOFT DRINKS
., _ A fruit flavor earbonated soft drink is produeed by dissol-ving one ounee by weight of one of the flavor eompositions sueh 2` as deseribed in Examples I or II in one gallon of sugar syrup.
One ounee of the resulting mixture is added to about five ounees of earbonated water to produee six ounees of earbonated beverage.
`~ ' ' The flavor eompo~ition eontaining 2.5% by weight of ethyl-2,
3-dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-earboxylate results in a level of 32 parts per million of ethyl-2,3-dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-earboxylate flavor enhaneer in the total earbonated drink produeed.
, .
/
- - -- -- - _ _ lO~iZ26~
EX~MPLE IX
. _ BUTTERSCOTCH FLAVOR COMPOSITION
A butterscotch composition containing a flavor enhancer in accordance with the teaching of the invention was prepared.
For comparison, another composition containing the same ingre-dients but without the flavor enhancer was also prepared as a control. The formulas of the compositions are as follows:
Parts by Parts by Weight Wei~ht ~Control) Butyl Butyrolactate 4.0 4.0 Diacetyl 0.2 0.2 Ethyl Oleate 2.0 2.0 Ethyl Myristate 0.5 0 5 Vanillin 1.5 1.5 Acetyl Methyl Carbinol 0.3 0.3 Phenyl Ethyl Alcohol 0.2 0.2 Butyric Acid 0.1 0.1 ; Ethyl Propionate 0.1 0.1 Ethyl Maltol 3 0 3.0 ; ~-Decalactone 0 3 0.
onalactone 0.1 0.1 Methyl Para-Tertiary Butyl Phenylacetate (in 1% alcohol) 0.1 0.1 Tincture Foenugreek 0.4 0.4 ~ ;
Cyclotene 0.1 0.1 Benzyl Alcohol 27.1 27.1 -~
Propylene Glycol 60.0 57.0 ; Ethyl-2,3-Dihydro-3(1'-Hydroxypropylidene)-2-Oxo-5-Ethyl-Furan-4-Carboxylate - 3.0 ` 100.0100.0 The butterscotch composition containing the flavor enhancer had an immeasurably superior flavor over the control.
; - 11 -- . .,`
-:
, .
/
- - -- -- - _ _ lO~iZ26~
EX~MPLE IX
. _ BUTTERSCOTCH FLAVOR COMPOSITION
A butterscotch composition containing a flavor enhancer in accordance with the teaching of the invention was prepared.
For comparison, another composition containing the same ingre-dients but without the flavor enhancer was also prepared as a control. The formulas of the compositions are as follows:
Parts by Parts by Weight Wei~ht ~Control) Butyl Butyrolactate 4.0 4.0 Diacetyl 0.2 0.2 Ethyl Oleate 2.0 2.0 Ethyl Myristate 0.5 0 5 Vanillin 1.5 1.5 Acetyl Methyl Carbinol 0.3 0.3 Phenyl Ethyl Alcohol 0.2 0.2 Butyric Acid 0.1 0.1 ; Ethyl Propionate 0.1 0.1 Ethyl Maltol 3 0 3.0 ; ~-Decalactone 0 3 0.
onalactone 0.1 0.1 Methyl Para-Tertiary Butyl Phenylacetate (in 1% alcohol) 0.1 0.1 Tincture Foenugreek 0.4 0.4 ~ ;
Cyclotene 0.1 0.1 Benzyl Alcohol 27.1 27.1 -~
Propylene Glycol 60.0 57.0 ; Ethyl-2,3-Dihydro-3(1'-Hydroxypropylidene)-2-Oxo-5-Ethyl-Furan-4-Carboxylate - 3.0 ` 100.0100.0 The butterscotch composition containing the flavor enhancer had an immeasurably superior flavor over the control.
; - 11 -- . .,`
-:
Claims (15)
1. A flavoring composition comprising a flavor component or componente and at least 0.0001% by weight of an alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate having the fonmulas in which R1 is a straight or branched chain alkyl having less than 6 carbon atoms and R2 is a straight or branched chain alkyl having less than 7 carbon atoms, cyclopentyl or cyclohexyl.
2. A flavor composition of claim 1 in which the alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate is ethyl-2,3-dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate.
3. A flavor composition of claim 1 in which the alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxy-late is ethyl-2,3-dihydro-3(1'-hydroxypropylidene)-2-oxo-5-ethyl-furan-4-carboxylate.
4. A flavor composition of claim 1 in which the alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate is ethyl-2,3-dihydro-3(1'-hydroxyisopentylidene)-2-oxo-5-isobutyl-furan-4-carboxylate.
5. A flavor composition of claim 1 in which the alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate present is 0.0001% to 30% by weight of the composition.
6. A flavor composition of claim 5 in which the alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate ie ethyl-2,3-dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate.
7. A flavor composition of claim 1 in which the alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate present is 0.001% to 20% by weight of the composition.
8. A flavor composition of claim 7 in which the alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate is ethyl-2,3-dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate.
9. A flavor composition of claim 1 in which the alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate present is 0.0025% to 5% by weight of the composition.
10. A flavor composition of claim 9 in which the alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate is ethyl-2,3-dihydro-3(1'-hydroxyethylidene)-2-oxo-5-methyl-furan-4-carboxylate.
11. A flavor composition of claim 1 in which the flavor com-ponent is smoking tobacco.
12. A flavor composition of claim 1 in which the flavor com-ponent is synthetic tobacco.
13. An alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylate having the formula:
in which R1 is a straight or branched chain alkyl having more than 1 and less than 6 carbon atoms, and R2 is a straight or branched chain alkyl having more than 1 and less than 7 carbon atoms, cyclopentyl or cyclohexyl.
in which R1 is a straight or branched chain alkyl having more than 1 and less than 6 carbon atoms, and R2 is a straight or branched chain alkyl having more than 1 and less than 7 carbon atoms, cyclopentyl or cyclohexyl.
14. A compound of claim 13 in which R1 and R2 are ethyl.
15. A compound of claim 13 in which R1 is isobutyl and R2 is ethyl.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60148275A | 1975-08-04 | 1975-08-04 | |
| US05/698,742 US4109662A (en) | 1975-08-04 | 1976-06-22 | Flavoring compositions containing alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1062269A true CA1062269A (en) | 1979-09-11 |
Family
ID=27083870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA257,711A Expired CA1062269A (en) | 1975-08-04 | 1976-07-23 | Flavoring compositions containing alkyl-2,3-dihydro-3(1'-hydroxyalkylidene)-2-oxo-5-alkyl-furan-4-carboxylates |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5218866A (en) |
| BE (1) | BE870873Q (en) |
| CA (1) | CA1062269A (en) |
| CH (1) | CH622685A5 (en) |
| DE (1) | DE2634509C2 (en) |
| GB (1) | GB1510060A (en) |
| NL (1) | NL7608662A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4771318B2 (en) * | 2009-02-02 | 2011-09-14 | 株式会社吉野工業所 | Injection mold for hinge lid |
-
1976
- 1976-07-23 CA CA257,711A patent/CA1062269A/en not_active Expired
- 1976-07-29 GB GB31698/76A patent/GB1510060A/en not_active Expired
- 1976-07-31 DE DE2634509A patent/DE2634509C2/en not_active Expired
- 1976-08-03 JP JP51092742A patent/JPS5218866A/en active Granted
- 1976-08-04 NL NL7608662A patent/NL7608662A/en not_active Application Discontinuation
- 1976-08-04 CH CH997276A patent/CH622685A5/en not_active IP Right Cessation
-
1978
- 1978-09-29 BE BE2057318A patent/BE870873Q/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5218866A (en) | 1977-02-12 |
| BE870873Q (en) | 1979-01-15 |
| DE2634509A1 (en) | 1977-02-17 |
| JPS627194B2 (en) | 1987-02-16 |
| DE2634509C2 (en) | 1985-09-12 |
| NL7608662A (en) | 1977-02-08 |
| GB1510060A (en) | 1978-05-10 |
| CH622685A5 (en) | 1981-04-30 |
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