CA1050815A - FLAVORING COMPOSITIONS CONTAINING DIALKYL-.alpha.,.beta.-DIACYL SUCCINATES - Google Patents
FLAVORING COMPOSITIONS CONTAINING DIALKYL-.alpha.,.beta.-DIACYL SUCCINATESInfo
- Publication number
- CA1050815A CA1050815A CA257,709A CA257709A CA1050815A CA 1050815 A CA1050815 A CA 1050815A CA 257709 A CA257709 A CA 257709A CA 1050815 A CA1050815 A CA 1050815A
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- flavor
- beta
- alpha
- succinate
- diacyl
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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
- A24B15/32—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by acyclic compounds
-
- 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
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2026—Hydroxy compounds
-
- 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
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
- A23L27/2028—Carboxy compounds
-
- 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
- A23L27/203—Alicyclic compounds
-
- 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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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Seasonings (AREA)
- Manufacture Of Tobacco Products (AREA)
- Confectionery (AREA)
- Fats And Perfumes (AREA)
Abstract
FLAVORING COMPOSITIONS CONTAINING
DIALKYL-.alpha.,.beta.-DIACYL SUCCINATES
ABSTRACT
The flavor compositions of this invention include certain dialkyl-.alpha.,.beta.-diacyl succinates which significantly enhance the flavor component or components of flavor com-positions. For example, butterscotch flavors are materially improved in smoothness, and certain fruit flavors are given greater richness and ripeness.
DIALKYL-.alpha.,.beta.-DIACYL SUCCINATES
ABSTRACT
The flavor compositions of this invention include certain dialkyl-.alpha.,.beta.-diacyl succinates which significantly enhance the flavor component or components of flavor com-positions. For example, butterscotch flavors are materially improved in smoothness, and certain fruit flavors are given greater richness and ripeness.
Description
lOS~ 5 This invention relates to ~lavor compo~itions and mora par-ticularly to flavor compositions containing certain dialkyl; ~J ~
diacyl succinate3. . ::
Ik i~ well known that synthetic flavor enhancere such a~ ;
Maltol, Ethyl MaltolJ and 4-hydroxy-2,5-dime~hyl-3(2H~-furanone are ~
useful a~ flavor enhancers. ~owever, ~uch flavor enhancers are very~ :
expen~ive and increase the cost of products in which they are used~
In accordance with this invention, dialkyl-a,~-diacyl ~ucci-nate~ are added to 1avor component~ to impart significantly en~
hanced ~lavors to a wide variety of flavor componente. For example, butterscotch flavors are materially improved in smoothness. Straw-berry flavor~ are given a striking freshness. Banana ~lavor~ are rounded out to give the ~lavor of a ripe banana. When added to smoking tobacco or ~ynthetic tobacco, the re~ulting p:eoduct i8 in-~rea~ed in sweetnsss, the ta~te of the smoke is ~o~tened and the flow o~ saliva i8 increa~ed, which le~sens dryxle~s of the mouth ' ' ' , ~)5~
during smoking. W~en addad to cough syrup~ contai~ing ~heophyl-line, tha flavor enhancers of this invention cover up the bittar tasto. ~he~e flavor enhancer~ can also be used to replace part of the sugar content of a wide variety of sweetened beverage~ and food~, producing excellant flavor at lower cost.
The dialkyl~ diacyl succinates employad in tha ~lavor com-po~ition~ o~ thi~ ~nv~ntion have ~he ~ormula~
O O
Rl ~~ O--R2 R2 ~ ~,~ Rl Il 11 .
O 0, in which Rl i~ a straig~t or ~ranched chain al~yl having les~
~ or cyclhe~<yl L ~ than 6 carbon atom ~ and ~2 is a ~traight or branched chain alkyl having le88 than 7 carbon atoms, cyclopentyl or cyclohexyl.
Example~ of Rl are methyl, ethyl, propyl, i~opropyl, butyl, ieobutyl, am~l or isoamyl.
Bxamplee o R2 are methyl, ethylJ propyl, iaop~py.l, bukylO
~o~ut~l, amyl, isoam~lJ hexyl or ieohexyl.
Rl and ~2 may be the ~ame or differer~t.
When R2 ie ethyl or methyl, the ~uccinate is prepared by the method de~ribed by ~., S. ~ewman and ~. S. Cella~ ~L ~38, 3482 ~1973). When R2 is other than ethyl or methyl, and Rl i5 other than methyl, the procedure is the same except that the appropriate ~-ketoesters are used instead of the acetoacetic esters.
The flavor compcsitions of this i~vention comprise at least 0.0025% by weight of a dialkyl~ diacyl succinate. The total amou~t o dialkyl-a,~ diacyl succinate or succinates may vary .
~ 2 ---8~
within wid~ ranges such as 0.0001% to 30% by weight. More advan-tageously the range may be between 0.001% and 20% by weight of the flavor composition and preferably between 0.0025% and 5% by weight of the flavor composition~
Examples of flavor components of the flavor compositions of this invention are flavor mixtures per se such as pineapple, but~
terscotch, banana, and strawberry; foodstu~fs such as meats, pro-~ein ~ources, fruitsJ cereals and other comestible~; beverages such as soft drinks, wines, alcoholic drinks, carbonated beverages;
smoking tobacco; liquid medicaments such as cough syrups; and sugar ubstitutes in a wide range of edible or drinkable products.
A more comprehensivs understanding o~ this invention is obtained from the ~ollowing examples. Examples I and II show com-positions produced with two levels o~ concentration o~ the dialkyl-aJ~-diacyl succinate employed.
EXAMPLE I
PINEAPPLE FLAVOR COMPOSITIONS
Parts by Parts by ~ wei~ht_ 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 0O5 0~5 Oil orange 1~0 1.0 Maltol 2.0 2.0 Diethyl-a,~diacetyl succinats 20.0 2.5 Ethyl alcohol 95% 46.0 46.0 Propylene glycol 13.6 3 100 . O 100 . O
~ 3 " " ~ ' ' ~5~
EX~MPLE II
STRAWBERRY FLAVOR COMPOSITIO~JS
Parts by Parts by 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 3O0 3.0 Iso7~utyric acid 1,5 1.5 Diacetyl 0.2 0.2 Butyl phenyl acetate 0,4 0,4 Acetaldehyde S0% in ethanol 0.2 0.2 Benzyl dipropyl ketone 0.2 0.2
diacyl succinate3. . ::
Ik i~ well known that synthetic flavor enhancere such a~ ;
Maltol, Ethyl MaltolJ and 4-hydroxy-2,5-dime~hyl-3(2H~-furanone are ~
useful a~ flavor enhancers. ~owever, ~uch flavor enhancers are very~ :
expen~ive and increase the cost of products in which they are used~
In accordance with this invention, dialkyl-a,~-diacyl ~ucci-nate~ are added to 1avor component~ to impart significantly en~
hanced ~lavors to a wide variety of flavor componente. For example, butterscotch flavors are materially improved in smoothness. Straw-berry flavor~ are given a striking freshness. Banana ~lavor~ are rounded out to give the ~lavor of a ripe banana. When added to smoking tobacco or ~ynthetic tobacco, the re~ulting p:eoduct i8 in-~rea~ed in sweetnsss, the ta~te of the smoke is ~o~tened and the flow o~ saliva i8 increa~ed, which le~sens dryxle~s of the mouth ' ' ' , ~)5~
during smoking. W~en addad to cough syrup~ contai~ing ~heophyl-line, tha flavor enhancers of this invention cover up the bittar tasto. ~he~e flavor enhancer~ can also be used to replace part of the sugar content of a wide variety of sweetened beverage~ and food~, producing excellant flavor at lower cost.
The dialkyl~ diacyl succinates employad in tha ~lavor com-po~ition~ o~ thi~ ~nv~ntion have ~he ~ormula~
O O
Rl ~~ O--R2 R2 ~ ~,~ Rl Il 11 .
O 0, in which Rl i~ a straig~t or ~ranched chain al~yl having les~
~ or cyclhe~<yl L ~ than 6 carbon atom ~ and ~2 is a ~traight or branched chain alkyl having le88 than 7 carbon atoms, cyclopentyl or cyclohexyl.
Example~ of Rl are methyl, ethyl, propyl, i~opropyl, butyl, ieobutyl, am~l or isoamyl.
Bxamplee o R2 are methyl, ethylJ propyl, iaop~py.l, bukylO
~o~ut~l, amyl, isoam~lJ hexyl or ieohexyl.
Rl and ~2 may be the ~ame or differer~t.
When R2 ie ethyl or methyl, the ~uccinate is prepared by the method de~ribed by ~., S. ~ewman and ~. S. Cella~ ~L ~38, 3482 ~1973). When R2 is other than ethyl or methyl, and Rl i5 other than methyl, the procedure is the same except that the appropriate ~-ketoesters are used instead of the acetoacetic esters.
The flavor compcsitions of this i~vention comprise at least 0.0025% by weight of a dialkyl~ diacyl succinate. The total amou~t o dialkyl-a,~ diacyl succinate or succinates may vary .
~ 2 ---8~
within wid~ ranges such as 0.0001% to 30% by weight. More advan-tageously the range may be between 0.001% and 20% by weight of the flavor composition and preferably between 0.0025% and 5% by weight of the flavor composition~
Examples of flavor components of the flavor compositions of this invention are flavor mixtures per se such as pineapple, but~
terscotch, banana, and strawberry; foodstu~fs such as meats, pro-~ein ~ources, fruitsJ cereals and other comestible~; beverages such as soft drinks, wines, alcoholic drinks, carbonated beverages;
smoking tobacco; liquid medicaments such as cough syrups; and sugar ubstitutes in a wide range of edible or drinkable products.
A more comprehensivs understanding o~ this invention is obtained from the ~ollowing examples. Examples I and II show com-positions produced with two levels o~ concentration o~ the dialkyl-aJ~-diacyl succinate employed.
EXAMPLE I
PINEAPPLE FLAVOR COMPOSITIONS
Parts by Parts by ~ wei~ht_ 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 0O5 0~5 Oil orange 1~0 1.0 Maltol 2.0 2.0 Diethyl-a,~diacetyl succinats 20.0 2.5 Ethyl alcohol 95% 46.0 46.0 Propylene glycol 13.6 3 100 . O 100 . O
~ 3 " " ~ ' ' ~5~
EX~MPLE II
STRAWBERRY FLAVOR COMPOSITIO~JS
Parts by Parts by 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 3O0 3.0 Iso7~utyric acid 1,5 1.5 Diacetyl 0.2 0.2 Butyl phenyl acetate 0,4 0,4 Acetaldehyde S0% in ethanol 0.2 0.2 Benzyl dipropyl ketone 0.2 0.2
2-~eptanone 0.1 0.1 Ethyl methyl phenyl glycidate 2.4 2.4 Diethyl-a,~-diacetyl succinate 30.0 5.0 Propylene gly~ol 51.0 51.0 Benzyl alcohol - 25 00 100 . O100 . O
.
. .
'' , " -: ' iLS
EXAMPLE III
.
BUT~ERSCOTCH FL~OR COMPOSITIO~
Parts by ~Teiqht :-.
Diethyl-a,~-diacetyl succinate 1.0 Butyl butyrolactate 4,0 ~iacatyl 0.2 Ethyl oleate 2.0 Ethyl myristate 0,5 Vanillin 1.5 Acetoin 0.3 Phenyl ethanol . 0.2 Butyric acid 0.1 Ethyl oxyhydrate 0.1 Ethyl maltol 3.0 ~Decalactone 0,3 ~-~onalactone 0.1 Tincture foenugreek 0,4 ~ethyl cyclopenten-ol-one 0.1 Benzyl alcohol 26.0 Propylene glycol 100 . O
' ' ; ' ' _ 5 _ :
i . .
~5~8~5 ~::
EX~MPLE IV
~AN~N~ FLAVOR COMPOSITION
Parts by ~~ .
Iso amyl acetate 12.0 Iso amyl butyrate 10.0 Benzyl butyrate 3,0 I~o amyl iso valerate 2.0 Ethyl butyrate 3.0 Butyric acid 1.5 Oil lemon 2.5 Vanillin 2.0 Ethyl maltol 0,5 ~ Undecalactone 0,4 4-~p-Hydroxyphenyl~-2-butanone 0.1 Diethyl~ diacetyl succinate . 10.0 ~ .
Propylene glyco~ 53 o ~.
100.0 ~.
'. ~ `
, , - ' ~.
~ .
~' ' ' :
~l)S~ 5 EX~MPLE V
PINEAPPLE FLAVOR
Parts by Weight VA VB VC VD
Allyl Cyclohexane Propionate1.4 l. 4 1~ 4 1 r 4 -Geranyl Propionate O.5 0.5 0.5 0,5 Allyl Caproats 13.0 13.0 13.0 13.0 Ethyl Iso Valerate 1.0 1.0 1.0 1.0 ~ :
Ethyl Butyrate 1.0 1.0 lo0 1~0 Vanillin 0.5 0,5 0.5 0.5 Oil Orange 1.0 loO 1~0 1~0 Maltol 2.0 2 J O - -Diethyl~ Diacetyl Succinate20.0 2.5 20.0 2.5 Ethyl Alcohol 95% 46.0 46.0 46~0 46~0 Propylene Glycol 13.6 31.1 15.6 33.1 :~
100 . () 100 . O 100 . O100 . O
Formulas U~ and VB contain Maltol in addition to diethyl-a,~-diacetyl succinate, while Formulas VC and VD contain only diethyl-~ diace~yl succinate as a complete replacement for Maltol. q~e pineapple 1avor achieved by the use of Formula VC is comparabla .i not superior to the flavor o Formula ~, while the flavor achi.eved by the use of Formula VD is comparable if not superior to the flavor of VB. The replacsment proportion of Maltol by diethyl- :
a,~-diacetyl succinate is approximately one part by weight to one part by weight of the Maltol.
. , .
~S~83L~ ~
EXAMPLE VI
WINE FL~VOR COMPOSITION
~ he wine flavor composition is produced by initially a~ding 0~08 parts by weight of diethyl-a,~-diacetyl succinate to 99.92 parts by weight of natural wine flavor. Four liquid ounces of the wine concentrate are added to one gallon o~ wine.
A wine 1avor composition may also be produced by preparing a 1% by weight ethanol solution of diethyl-~ diacetyl succinate and then adding O.32 fluid ounces of the solution to 1 gallon of wine. This is equivalent to 25 parts per million.
EXAMPLE VII ~ ;
_BACCO FLAVOR CO~POSITION
A 1% ethanol solution of diethyl~a,~diacetyl succinate is sprayed on smoking tobacco at the rate of 4 ounces of solution per 100 pounds of tobacco. After the alcohol is allowed to evapo-rate, a tobacco flavor composition results.
To produce a flavored tobacco which also contains synthetic tobacco, the procedure for the production of tobacco flavor com~
position heretofore described in this Example is repeated except that instead of employing smoking tobacco only, synthetic tobacco such as csllulose fibers, for example~ the cellulose fibers sold by the Celanese chemical Company under the trademark "CYTREL" or the cellulose fibers sold by Imperial Chemical Corporation under the trademark "PO~YSTREP"~ is blended with the flavored tobacco in a ratio o~ approximately 1 to 1 by weight.
In a ~hird procedure, a 1% ethanol solution of die~hyl-a,~-~ 8 ..
~s~s diacetyl succinate is sprayed on synthetic tobacco, such ascellulose fibers, at the rate of 4 ounces of solution to 100 pounds of synthe~ic tobacco. After the alcohol i6 allowed to evaporate, a tobacco flavor synthetic composition results.
~ ny one of the above tobacco flavor compositions may be used in cigarettes, producing a striking improvement in flavor~
For the treatment of tobacco, it is desirable that the fla-vor enhancer be in solubilized form, such as in an ekhanol solu tion, as in the example of diethyl-a,~-diacetyl succinate.
EXAMPLE YIII
CARBON~TED SOFT DRINKS
A fruit flavor carbonated drink is produced by dissolving one ounce by weight o one of the flavor compositions such as described in Examples I or II in one gallon of sugar syrup.
one ounce of the resulting mixture is added to about five ounces of carbonated water to produce six ounces of carbonated beverage.
The flavor composition containing 2.5% by weight of diethyl ~
diacetyl succinate results in a level of 32 parts per million of the diethyl-a,~ diacetyl succinate flavor enhancer in the total carbonated drink produced.
In Examples I through IX~ dimethyl-a,~-diacetyl succinate may be utilized as the flavor enhancer in the same amounts indi-cated ~or dieth~ diacetyl succinate used in those Examples.
;
; g _ i~S~;)8~5 EXAMPLE IX
BUTTERSCOTCH FLA~OR COMPOSITION
Two butterscotch compositions each containing a different fla-vor enhancer in accordance with the teaching o~ tha invention were prepared. For comparison, another composition containing the ~ame ingredien~s but without either of the flavor enhancers used in A
and B was also prepared as a control. The formulas of the compo-si~ion-~ are as ollow~:
Parts by Part~ by Parts by Weight Weight Weight ~Control) ~A~ _ Butyl Butyrolactate 4.0 4O0 4.0 Diacetyl 0.2 0.2 0.2 Ethyl oleate 2.0 2.0 2.0 Ethyl Myristate 0.5 0,5 0.5 Vanillin 1.5 1.5 1.5 Acetyl Methyl Carbinol 0.3 0.3 0.3 Phenyl Ethyl A}cohol 0.2 0.2 0.2 Butyric Acid 0.1 0.1 0.1 ~thyl Propionate 0.1 0.1 0.1 Ethyl Maltol 3.0 3.0 3.0 :
~-Decalactone 0.3 0.3 0.3 ~-Nonalactone 0.1 0.1 0.1 Methyl Para-Tertiary Butyl Phenylacetate (in 1% alcohol) 0O1 0.1 0.1 ~.
Tinctuxe Foenugreek 0.4 0.4 0,4 cyclotene 0~1 0.1 0.1 Benzyl Alcohol 27.1 27.1 27.1 :
Propylene Glycol 60.0 57~0 57.0 Diethyl-a,~-Dipropionyl Succinate - - 3.0 Dicy~lohexyl-a,~-Dlacetyl Succinate - 3.0 _ 100.0 1~0,.0 100.0 . _ _ . .. ~ _ _ __ _ _ ___ .. , , . ., .. , ___ _ _ _.. . . .... . ., . .. __ _ _ ~ ~
~.~ . ', . .
, , .
Each of the butterscokch compositions containing the flavor enhancers (~) and (B) had an immeasurably supexior flavor over the control. The butterscotch compositions (~) and (B) had a batter butterscotch caramel flavor and an increased sweetness and mouth feel. Tha butter no es were al~o anhancedO
~, .
.
. .
'' , " -: ' iLS
EXAMPLE III
.
BUT~ERSCOTCH FL~OR COMPOSITIO~
Parts by ~Teiqht :-.
Diethyl-a,~-diacetyl succinate 1.0 Butyl butyrolactate 4,0 ~iacatyl 0.2 Ethyl oleate 2.0 Ethyl myristate 0,5 Vanillin 1.5 Acetoin 0.3 Phenyl ethanol . 0.2 Butyric acid 0.1 Ethyl oxyhydrate 0.1 Ethyl maltol 3.0 ~Decalactone 0,3 ~-~onalactone 0.1 Tincture foenugreek 0,4 ~ethyl cyclopenten-ol-one 0.1 Benzyl alcohol 26.0 Propylene glycol 100 . O
' ' ; ' ' _ 5 _ :
i . .
~5~8~5 ~::
EX~MPLE IV
~AN~N~ FLAVOR COMPOSITION
Parts by ~~ .
Iso amyl acetate 12.0 Iso amyl butyrate 10.0 Benzyl butyrate 3,0 I~o amyl iso valerate 2.0 Ethyl butyrate 3.0 Butyric acid 1.5 Oil lemon 2.5 Vanillin 2.0 Ethyl maltol 0,5 ~ Undecalactone 0,4 4-~p-Hydroxyphenyl~-2-butanone 0.1 Diethyl~ diacetyl succinate . 10.0 ~ .
Propylene glyco~ 53 o ~.
100.0 ~.
'. ~ `
, , - ' ~.
~ .
~' ' ' :
~l)S~ 5 EX~MPLE V
PINEAPPLE FLAVOR
Parts by Weight VA VB VC VD
Allyl Cyclohexane Propionate1.4 l. 4 1~ 4 1 r 4 -Geranyl Propionate O.5 0.5 0.5 0,5 Allyl Caproats 13.0 13.0 13.0 13.0 Ethyl Iso Valerate 1.0 1.0 1.0 1.0 ~ :
Ethyl Butyrate 1.0 1.0 lo0 1~0 Vanillin 0.5 0,5 0.5 0.5 Oil Orange 1.0 loO 1~0 1~0 Maltol 2.0 2 J O - -Diethyl~ Diacetyl Succinate20.0 2.5 20.0 2.5 Ethyl Alcohol 95% 46.0 46.0 46~0 46~0 Propylene Glycol 13.6 31.1 15.6 33.1 :~
100 . () 100 . O 100 . O100 . O
Formulas U~ and VB contain Maltol in addition to diethyl-a,~-diacetyl succinate, while Formulas VC and VD contain only diethyl-~ diace~yl succinate as a complete replacement for Maltol. q~e pineapple 1avor achieved by the use of Formula VC is comparabla .i not superior to the flavor o Formula ~, while the flavor achi.eved by the use of Formula VD is comparable if not superior to the flavor of VB. The replacsment proportion of Maltol by diethyl- :
a,~-diacetyl succinate is approximately one part by weight to one part by weight of the Maltol.
. , .
~S~83L~ ~
EXAMPLE VI
WINE FL~VOR COMPOSITION
~ he wine flavor composition is produced by initially a~ding 0~08 parts by weight of diethyl-a,~-diacetyl succinate to 99.92 parts by weight of natural wine flavor. Four liquid ounces of the wine concentrate are added to one gallon o~ wine.
A wine 1avor composition may also be produced by preparing a 1% by weight ethanol solution of diethyl-~ diacetyl succinate and then adding O.32 fluid ounces of the solution to 1 gallon of wine. This is equivalent to 25 parts per million.
EXAMPLE VII ~ ;
_BACCO FLAVOR CO~POSITION
A 1% ethanol solution of diethyl~a,~diacetyl succinate is sprayed on smoking tobacco at the rate of 4 ounces of solution per 100 pounds of tobacco. After the alcohol is allowed to evapo-rate, a tobacco flavor composition results.
To produce a flavored tobacco which also contains synthetic tobacco, the procedure for the production of tobacco flavor com~
position heretofore described in this Example is repeated except that instead of employing smoking tobacco only, synthetic tobacco such as csllulose fibers, for example~ the cellulose fibers sold by the Celanese chemical Company under the trademark "CYTREL" or the cellulose fibers sold by Imperial Chemical Corporation under the trademark "PO~YSTREP"~ is blended with the flavored tobacco in a ratio o~ approximately 1 to 1 by weight.
In a ~hird procedure, a 1% ethanol solution of die~hyl-a,~-~ 8 ..
~s~s diacetyl succinate is sprayed on synthetic tobacco, such ascellulose fibers, at the rate of 4 ounces of solution to 100 pounds of synthe~ic tobacco. After the alcohol i6 allowed to evaporate, a tobacco flavor synthetic composition results.
~ ny one of the above tobacco flavor compositions may be used in cigarettes, producing a striking improvement in flavor~
For the treatment of tobacco, it is desirable that the fla-vor enhancer be in solubilized form, such as in an ekhanol solu tion, as in the example of diethyl-a,~-diacetyl succinate.
EXAMPLE YIII
CARBON~TED SOFT DRINKS
A fruit flavor carbonated drink is produced by dissolving one ounce by weight o one of the flavor compositions such as described in Examples I or II in one gallon of sugar syrup.
one ounce of the resulting mixture is added to about five ounces of carbonated water to produce six ounces of carbonated beverage.
The flavor composition containing 2.5% by weight of diethyl ~
diacetyl succinate results in a level of 32 parts per million of the diethyl-a,~ diacetyl succinate flavor enhancer in the total carbonated drink produced.
In Examples I through IX~ dimethyl-a,~-diacetyl succinate may be utilized as the flavor enhancer in the same amounts indi-cated ~or dieth~ diacetyl succinate used in those Examples.
;
; g _ i~S~;)8~5 EXAMPLE IX
BUTTERSCOTCH FLA~OR COMPOSITION
Two butterscotch compositions each containing a different fla-vor enhancer in accordance with the teaching o~ tha invention were prepared. For comparison, another composition containing the ~ame ingredien~s but without either of the flavor enhancers used in A
and B was also prepared as a control. The formulas of the compo-si~ion-~ are as ollow~:
Parts by Part~ by Parts by Weight Weight Weight ~Control) ~A~ _ Butyl Butyrolactate 4.0 4O0 4.0 Diacetyl 0.2 0.2 0.2 Ethyl oleate 2.0 2.0 2.0 Ethyl Myristate 0.5 0,5 0.5 Vanillin 1.5 1.5 1.5 Acetyl Methyl Carbinol 0.3 0.3 0.3 Phenyl Ethyl A}cohol 0.2 0.2 0.2 Butyric Acid 0.1 0.1 0.1 ~thyl Propionate 0.1 0.1 0.1 Ethyl Maltol 3.0 3.0 3.0 :
~-Decalactone 0.3 0.3 0.3 ~-Nonalactone 0.1 0.1 0.1 Methyl Para-Tertiary Butyl Phenylacetate (in 1% alcohol) 0O1 0.1 0.1 ~.
Tinctuxe Foenugreek 0.4 0.4 0,4 cyclotene 0~1 0.1 0.1 Benzyl Alcohol 27.1 27.1 27.1 :
Propylene Glycol 60.0 57~0 57.0 Diethyl-a,~-Dipropionyl Succinate - - 3.0 Dicy~lohexyl-a,~-Dlacetyl Succinate - 3.0 _ 100.0 1~0,.0 100.0 . _ _ . .. ~ _ _ __ _ _ ___ .. , , . ., .. , ___ _ _ _.. . . .... . ., . .. __ _ _ ~ ~
~.~ . ', . .
, , .
Each of the butterscokch compositions containing the flavor enhancers (~) and (B) had an immeasurably supexior flavor over the control. The butterscotch compositions (~) and (B) had a batter butterscotch caramel flavor and an increased sweetness and mouth feel. Tha butter no es were al~o anhancedO
~, .
Claims (10)
1. A flavor composition comprising a flavor component or components and at least 0.0001% by weight of a dialkyl-.alpha.,.beta.-diacyl succinate having the formula:
in which R1 is a straight or branched chain alkyl having less than 6 carbon atoms or cyclohexyl and R2 is a straight or branched chain alkyl having less than 7 carbon atoms, cyclopentyl or cyclohexyl.
in which R1 is a straight or branched chain alkyl having less than 6 carbon atoms or cyclohexyl 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 dialkyl-.alpha.,.beta.-diacyl succinate is dimethyl-.alpha.,.beta.-diacetyl succinate.
3. A flavor composition of claim 1 in which the dialkyl-.alpha.,.beta.-diacyl succinate is diethyl-.alpha.,.beta.-diacetyl succi-nate.
4. A flavor composition of claim 1 in which the dialkyl-.alpha.,.beta.-diacyl succinate present is 0.0001% to 30% by weight of the composition.
5. A flavor composition of claim 1 in which the dialkyl-.alpha.,.beta.-diacyl succinate present is 0.001% to 20.% by weight of the composition.
6. A flavor composition of claim 1 in which the dialkyl-.alpha.,.beta.-diacyl succinate present is 0.0025% to 5% by weight of the composition.
7. A flavor composition of claim 1 in which a flavor component is smoking tobacco.
8. A flavor composition of claim 1 in which a flavor component is synthetic tobacco.
9. A flavor composition of claim 1 in which the dial-kyl-.alpha.,.beta.-diacyl succinate is diethyl-.alpha.,.beta.-dipropionyl succinate.
10. A flavor composition of claim 1 in which the dial-kyl-.alpha.,.beta.-diacyl succinate is dicyclohexyl-.alpha.,.beta.-diacetyl succinate.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60230175A | 1975-08-06 | 1975-08-06 | |
| US05/698,741 US4140134A (en) | 1975-08-06 | 1976-06-22 | Flavoring compositions containing dialkyl-α, β-diacyl succinates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1050815A true CA1050815A (en) | 1979-03-20 |
Family
ID=27084098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA257,709A Expired CA1050815A (en) | 1975-08-06 | 1976-07-23 | FLAVORING COMPOSITIONS CONTAINING DIALKYL-.alpha.,.beta.-DIACYL SUCCINATES |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5934107B2 (en) |
| BE (1) | BE870874A (en) |
| CA (1) | CA1050815A (en) |
| CH (1) | CH622686A5 (en) |
| DE (1) | DE2634510C2 (en) |
| GB (1) | GB1514090A (en) |
| NL (1) | NL7608660A (en) |
-
1976
- 1976-07-23 CA CA257,709A patent/CA1050815A/en not_active Expired
- 1976-07-29 GB GB31699/76A patent/GB1514090A/en not_active Expired
- 1976-07-31 DE DE2634510A patent/DE2634510C2/en not_active Expired
- 1976-08-03 JP JP51092743A patent/JPS5934107B2/en not_active Expired
- 1976-08-04 NL NL7608660A patent/NL7608660A/en not_active Application Discontinuation
- 1976-08-06 CH CH1010276A patent/CH622686A5/en not_active IP Right Cessation
-
1978
- 1978-09-29 BE BE2057319A patent/BE870874A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2634510A1 (en) | 1977-02-17 |
| DE2634510C2 (en) | 1985-10-24 |
| CH622686A5 (en) | 1981-04-30 |
| BE870874A (en) | 1979-01-15 |
| JPS5934107B2 (en) | 1984-08-20 |
| JPS5221372A (en) | 1977-02-17 |
| NL7608660A (en) | 1977-02-08 |
| GB1514090A (en) | 1978-06-14 |
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