DE2605286C2 - 3-furylalkyl sulfides and their use - Google Patents

Description

The invention relates to 3-FuryialkyIsulfide of the general formula

CHj

wherein Ri is a Ci- to Cs-alkyl group and R2 is hydrogen or represent the methyl group.

These compounds are suitable as seasonings for food.

Furan compounds that contain a sulfur residue in the 3-position are known and it is on theirs organoleptic properties pointed out. It has also been found that the compounds according to the invention are compared with the known ones with regard to the flavoring properties, in particular the taste effect Have advantages. This is enlivened by some comparative tests that have been carried out with products which are known from DE-OS 19 32 800, DE-AS 21 00 923 and DE-OS 20 03 525.

Prior art connections:

The 4,5-dihydro-2-methyl-3-furanthiol acetate of the formula

3 of DE-AS 21 00 923, namely: 100 mg of 4-hydroxy-2 ^ 5-dimethy! -3 (2 H) furanone, 0.5 ml of a 30% aqueous solution of sodium sulfide nonahydrate (Na ₂ S · 9 H ₂ O) and 9.5 ml of one with 0.1 M Sodium potassium monophosphate buffered solution was in a Parr bomb for 3 hours at one pressure Cooked by 24H bar

The well-known from DE-OS 20 03 525 2-methyl-3-furanthiol was prepared as follows: In an on - 8O ⁰ C A cooled and stirred mixture of diglycol dimethyl ether saturated with gaseous hydrochloric acid and 2-methyl-3-tetrahydrofuran was also evaporated to -8O ⁰ C cooled hydrogen sulfide and the reaction mixture was allowed to stand. Then was with

is sodium bicarbonate neutralized, treated with water and extracted quickly with methylene chloride. The organic solution thus obtained was dried and evaporated and the oil obtained is distilled at 80 ° fraction passed over to 83 ° C and 57 mm Hg

Chromatographies and 2-methyl-3-furanthioI isolated.

These known compounds were compared with the following compounds according to the invention:

(2-methyl-3-furyI) methyl sulfide;

(24-Dimethyl-3-furyl) propyl sulfide and

Isoamyl- (2-methyl-3-furyr) sulF! D. The following tables show the organoleptic properties of the comparison products:

JO table 1

Known connections

was prepared according to example A9 of DE-OS 19 32 800, namely: 3-chloro-3-acetylpropanol were with potassium acetate in a 1: 1.5 in. molar ratio Acetone refluxed for about 2 hours. After cooling, the reaction mixture became filtered, the filtrate evaporated and the residue dissolved in water. The solution was made with chloroform extracted, the combined extracts washed, dried, evaporated and the residue removed distilled

The reaction product of 4-hydroxy-2,5-dimethyl-24-dihydrofuranone- (3) with hydrogen sulfide - in a molar ratio of 3.9: 1.4 was prepared according to Example CIO of DE-OS 19 32 800. The reaction took place in Presence of water in an autoclave, the reaction mass being heated ^{to 100 ° C. for 2 hours.}

The reaction product from 4-hydroxy-2,5-dimethyl 3 (2 H) -furanone with sodium sulfide was according to Example Organoleptic tables Properties in water

4,5-dihydro-2-methyl-3-furanthiolacetate solution in undenatured Alcohol (example A9, DE-OS 19 32 800)

Reaction product of 4-hydroxy-2,5-dimethyl-3 (2H) furanone with H ₂ S at 1 atm. - produced as stated above (according to DE-OS 19 32 800. Example CIO)

Reaction product from 4-HydroKy-2,5-dimethyl-3 (2H) furanone with H ₂ S, prepared according to Example 3 (DE-AS 21 00 923)

At 0.05 ppm, neither taste nor aroma. At 0.2 ppm a sweet, an Warm onion-like taste with a tongue-biting effect.

At I ppm a sweet, somewhat reminiscent of roast beef, but unacceptably metallic Note, and the sulfur is not included harmoniously and does not carry to round off.

Well mixed, sweet character reminiscent of roast meat with a characteristic sulfur note of meat, well balanced with the other meat notes, however no liver nuance.

As has been found in several attempts the 2-methyl-3-furanthiol according to DE-OS 20 03 525 probably an aroma and flavor of roast meat, but without any aroma notes reminiscent of liver nor spice characteristics. Furthermore are the flavoring properties of this known compound are inferior to those of the compounds according to the invention and are also stored somewhat differently.

Table 2 Compounds According to the Invention

3-FuryIaJkyIsuldd

Example] after the connection has been established

Flavoring bowls

1. (2-Methyl-3-furyl) methyl sulfide 0.1 ppm

2. (2,5-Dimethyl-3-furyl) propylene sulfide 2 ppm

3. IsoamyI (2-raeJiyl-3-furyl) suIfid 0.5 ppm

Sweet, meat extract cereal-like wünj with Bouillon-like and nutty notes and a sweet, bouillon-like aroma.

Onion-like, sulphurous aroma and a pleasant meat-like, sulphurous taste.

Sweet, baked bread, meat-like aroma with boar-like nuances and green, sweet, yeast-like seasoning reminiscent of hydrolyzed vegetable protein with baked bread, hazelnut, liver, sulfur and Pecan-like nuances.

The investigations were carried out as follows:

The comparison compounds were first brought to a concentration of 1% with 95% undenatured ethyl alcohol. The test solutions were then with water to a concentration of 0.1 ppm, 0.5 ppm, 1 ppm and 5 ppm diluted

Each sample of the test solution egg * was taken from one Test group of at least four people examined for the aroma, taste and smell and then a decision was made about the organoleptic properties.

The 3-furylalkyl sulfides according to the invention can be prepared by the following process: (1) a 2-ene-1,4-dione of the formula

(2)

CHj

is intimately mixed with an alkanethiol of the formula RiSH and a substituted one or not substituted 2-thia-substituted 1,4-dione of the formula

CH ₃

educated;

(3) this 1,4-dione is cyclized to give a substituted one or unsubstituted 3-FuryIalkylsulfid der formula

^s \

R. CH,

where Ri and R2 are the groups given above. R2

v) can be hydrogen if in step (2) the 2-ene-2,4-dione with an alkanethiol of the formula RiSH in the presence of an organic base such as piperidine, pyridine, triethylamine, quinoline or «-picoline or a mixture thereof is mixed.

ι> Examples of such alkanethiols are: ethanethiol, 1-propanethiol, methanethiol, 1-pentanethiol, 2-pentanethiol, 2-propanethiol, 1-butanethiol, 2-butanethiol, 2-methyl-2-propanethiol, 2-methyl-2-propanethiol, 3-methyl-1-butanethiol, 2-methyl-1-butanethiol, 2-methyl-2- butanethiol and 2-methyl-3-butanethiol.

The reaction product is then purified, for example by appropriate extraction and distillation. The process steps are known from US Pat. Nos. 3,872 and 3,873,731

r, 3-Furylalkylsulfide invention can methyl-3-furanthiol 2 by reacting 3-Furanthiolen, for example, with an appropriate alkyl halide in the presence of a base such as an alkali metal alkoxide (x., sodium methoxide) was prepared

■> o, at a temperature in the range of 15 ° to 100 ° C and in a corresponding inert, compatible solvent, for example an anhydrous lower alcohol such as methanol, ethanol or Isoproparol. So when reacting methyl iodide with 2-methyl-3-furanthiol in anhydrous methanol in the presence of sodium methoxide at a temperature obtained from 24 ° C (2-methyl-3-furyl) methyl sulfide. A Another example is the reaction of sodium methylate with 2-methyl-3-furanthiol, with a corresponding

Mercaptide is formed, which in turn with l-bromo-3-

methylbutän at reflux temperature and 0.98 bar implemented and thereby isoamyl (2-methyl-3-furyl) sulfide is formed.

The 3-furylalkyl sulfides according to the invention are suitable

f.) due to their organoleptic properties to change, vary, intensify, modify the seasoning, aroma and / or taste of a large number of edible and consumable products.

change, improve or otherwise influence.

Under "change" and "modify" is understood that tired, relatively tasteless products are a Spice character or a spicy note given, or already existing spice characteristics strengthened, can be supplemented and / or changed.

The term "reinforce" means that a Würzoder The aroma note or nuance is intensified but the quality is not changed or impaired. That Condiments used for fortifying do not add any additional flavor or nuance if it is is added in an appropriate concentration based on the weight of the food in question is related.

It has been found that the 3-furylalkyl sulfides of the invention are extremely useful seasoning compositions and contribute to the overall flavor impression by adding or enhancing a natural or artificial flavoring in the product or impart substantially all of the flavor and / or aroma to the consumable.

The seasonings according to the invention are used to season foods that can be solid and liquid and serve as food, with or without nutritional value, for humans and animals. This is where meat belongs Sauces, soups, ready meals, vegetables, snacks, dog and cat food, other veterinary products.

The 3-furylalkyl sulfides used as seasonings can be used alone or together with conventional ones Condiments or auxiliaries are added, jo Such additives or seasoning auxiliaries are known and described in detail in the literature. They have to be inert and not with the 3-furylalkyl sulfides must react, both from an aesthetic and organoleptic point of view, and they must be usable must not be toxic or otherwise harmful. Such additives or condiments are other seasoning compositions, carriers, stabilizers, thickeners, wetting agents, conditioning agents and seasoning enhancers.

Examples of preferred seasoning additives are:
Methylthiazole alcohol

(4-methyl-5-j3-hydroxyethylthia7.o!);
2-methylbutanethiol; 4-mercapto-2-butanone;
3-mercapto-2-pentanone;

1-mercapto-2-propanone; Benzaldehyde;
Furfural; Furfuryl alcohol;
2-mercaptopropionic acid;
2-methylfuran-3-thiol;

2-methyldihydrofuran-3-thiol; -, 0

2-methyltetralydrofuran-3-thioI;
2-ethylfuran-3-thiol;

2 ethyl dihydrofuran-3-thiol;
2-ethyl tetrahydrofuran-3-thiol;
2-propylfuran-3-thiol; 2-isopropylfuran-3-th! Ol;
2-isopropyldihydrofuran-3-thiol;
2-isopropyl tetrahydrofuran-3-thiol;
2-propyldihydrofuran-3-thiol;

2,5-dimethylfuran-3-thiol; mi

2,5-dimethyldihydrofuran-3-thiol;
2,5-D'imethylietrahydrofuran-3-thiol;
2,5-diethyIfuran-3-thiol;
2,5-diethyldihydrofuran-3-thiol;
2.5-diethyltetrahydrofuran-3-thiol: _h s

2-ethyl-5-methylfuran-3-ihiol;

2-methyl-ethylfuran-3-thiol;
2-ethyl-5-mt.t ^l r / l-dihydrofuran-3-thiol; 2-ethyl-5-methyltetrahydrofuran-3-thio |; 2,5-dipropylfuran-3-thiol;

2,5-diisopropylfuran-3-thiol;

5-isopropyl-2-methylfuran-3-thiol; 2-butylfuran-3-thiol;

2-ethyl-5-propyltetrahydrofuran-3-thiol; Bis (2-methyl-3-furyl) suIfid;

Bis (2-methyl-3-furyl) distilfid;

Bis (2-ethyl-3-furyl) sulfide;

Bis (2-ethyl-3-furyl) disulfide;

Bis (2,5-dimethyl-3-furyl) sulfide;

Bis (2,5-dimethyl-3-furyl) disulfide; Bis (2-methyl-3-dihydrofuryI) sulfide; Bis (2-methyl-3-tetrahydrofuran) sulfide; Bis (2-methyI-3-tetrahydrofuryI) disulfide; Bis (2-methyl-3-dihydrofury!) Disulfide; Bis (2,5-diethyI-3-dihydrofury) sulfide; Bis (2,5-diethyl-3-furyl) sulfide;

Bis (2-ethyl-5-methyl-3-furyl) disulfide; Bis (2,5-diethyl-3-furyl) disulfide;

Bis (2,5-dipropyl-3-furyl) di '· i'Jid; Bis (2 ^ -d! Propyl-3-fury!) Suft! D;

Bis (2,5-dibutyl-3-furyl) disulfide;

Bis (5-ethyl-2-methyl-3-dihydrofuryl) disulfide;

Bis (2-isopropyl-3-furyl) sulfide;

Bis (2-isopropyl-3-furyl) disulfide; Bis (2-isopropyl-3-dihydrofuryl) sulfide;

Bis (2-isopropyl-3-tetrahydrofuryl) disulfide;

Alkylpyrazine; Methylpyrazine;

2-ethyl-3-methylpyrazine;

Tetramethylpyrazine; dipropolyidisulfide; Methylbenzyl disulfide; Alkylthiophenes; 2-butylthiophene; 2,3-dimethylthiophene; 5-methylfurfuraI; Acetylfuran;

2,4-decadienal; Guiacol;

Phenylacetaldehyde decalactone; d-limonene; Acetoin; Amyl acetate; Maltol;

Ethyl butyrate; Levulinic acid; Piperonal;

Ethyl acetate; n-octanaI; n-pentanaI; Hexanal; Diacetyl; Monosodium glutamate; sulfur-containing amino acids; Cysteine; hydrolyzed vegetable protein; hydrolyzed fish protein;

Tetramethylpyrazine.

The 3-FuryIakylsulfide can with one or more Carriers are combined so that they can be added to the product to be seasoned. the Carriers can be edible or other corresponding substances, such as ethyl alcohol, propylene glycol, Water. This subheading also includes substances such as gum arabic, carrageenan and other types of gum.

The 3-furylalkyl sulfides can be introduced together with their carrier in a manner known per se, for example by spray drying, drum drying.

The carriers can also contain substances which allow the 3-furylalkyl sulfides which are used as seasonings and other seasoning ingredients, if any.

When the carrier is an emulsion, the seasoning composition can also contain emulsifying agents such as mono- and diglycerides or fatty acids. The desired physical form of the composition can be created with such carriers.
The amount of 3-furylalkyl sulfide added should be sufficient

to achieve the desired flavoring characteristics obtain. Not only is an excess uneconomical, but too large an amount can in some cases adversely affect the flavor and other organoleptic properties of the product. As usual hangs the required amount depends on several factors, such as the finished food, the amount and type of originally regional and other factors, the type of storage, pretreatment, such as baking and roast meat.

The final product has been found to have an amount of from about 0.0005 ppm to about 250 ppm of 3-furylalkyl sulfides may contain to show good results. Within this quantity range, with approx 0.0005 up to 100 ppm seasoning qualities improved and an amount of about 0.2 to 50 ppm gives the End product positive seasoning characteristics. All parts, proportions, percentages and ratios are in Expressed weight, unless otherwise stated.

The amount of 3-furylalkyl sulfides in seasoning compositions can vary within a wide range. So can from around 2 ppm up to 80 or 90% of the entire seasoning composition consist of one or more 3-furylalkyl sulfides. It was found that very good and desirable results with an amount of about 10 ppm up to about 20% 3-furylalkyl sulfide in such seasoning compositions can be achieved.

The invention is explained in more detail with the aid of the examples.

example 1
Production of (2-methyl-3-furyl) methyl sulfide

In a 50 ml round bottom flask fitted with a 10 ml funnel, magnetic stirrer, nitrogen inlet, Y-tube. CaCb drying tube and thermometer were provided, 7.5 ml of anhydrous methanol were introduced and 0.474 g (0.00878 mol) of NaOCH _{3 were} added to this with stirring. The reaction mass was then cooled to 24 ° C. and a solution of 1.0 g (0.00878MoI) of 2-methyl-3-furanthiol in 7.5 ml of anhydrous methanol was added under a nitrogen blanket.

A solution of 1.248 g (0.00878 mol) of methyl iodide in 4 ml of anhydrous methanol was obtained over 15 minutes added and this reaction mass stirred for 30 minutes before adding 30 ml of water and the The pH of the mixture obtained was adjusted to 5 with 4% hydrochloric acid. The mixture became then extracted twice with hexane (16 and 15 ml) Hexane extracts were filtered and then made up to 2 ml concentrated

Gas-liquid chromatography showed the following Links:

Peak A

Peak B

NS,

5.4%

8 'x ¹ A "column Peak A, the desired product, was isolated by preparative gas-liquid chromatography. Yield was 90%.

MS-. IR and NMR analyzes confirmed the structural formula

NS,

That connection had a sweet one. Meat extract-cereal-like seasoning with bouillon-like and nutty ones Notes and a sweet, bouillon-like aroma.

The molecular weight was 128.

The MS analysis showed:

m / 'e

43

45

51

69

81

85

99

) \ 3

η 128

Example Ί

Preparation of (2,5-dimethyl-3-furyl) propyl sulfide

In a 500 ml three-necked round bottom flask fitted with a reflux condenser, magnetic stirrer, calcium chloride drying tube and a pot thermometer. 300 ml of isopropenyl acetate were introduced. This was heated to reflux and 30 g of 3-propylthio-2,5-hexanedione were added. When reflux occurred again, 03 ml of concentrated sulfuric acid was added and the mixture was further refluxed for 4 hours and 40 minutes. While cooling, 2 g of sodium carbonate was added. After the reaction mixture cooled to room temperature, the solids were filtered and the excess isopropyl acetate removed in vacuo. The residue was dissolved in 55 ml of benzene and washed with 10 ml of saturated sodium bicarbonate solution. The solution was then washed with sodium sulfate, the solvent was removed in vacuo and 363 g of a brown oil were obtained. Vacuum distillation gave 13.4 g (23-dimethyl-3-furyl) propyl sulfide as a light yellow OL which boiled at 70-713 ° C. at 4 torr. Yield 21%.

NMR, IR and MS analyzes confirmed the structural formula:

X / X

Chromatography conditions: 25% SE-30,

The 3-propylthio-2p-hexanedione was as follows manufactured:

95 ml of ether, 35.4 g of ds-3-hexene-23-

dione and a drop of piperidine were added. Then 24 g of n-propanethiol were gradually added and as the addition progressed, more piperidine (33 drops in total) was also added periodically. After standing for 18 hours, the solution was washed successively with 10% hydrochloric acid (2 × 7.5 ml), saturated sodium chloride solution (10 ml), Woiger sodium bicarbonate solution and saturated sodium chloride solution (2 × 10 ml). The ether solution was kneaded over sodium sulfate and concentrated, 51.4 g of a dark yellow oil being obtained. Gas-liquid chromatography showed it to be essentially pure 3-propylthio-2,5-hexanedione.
The cis-3-hexene-2,5-dione was prepared as follows: 200 g of 2,5-dimethoxy-2,5-dimethyl-2, 5-dihydrofuran and 250 ml of a 1 <Vbigen aqueous acetic acid solution were introduced. This solution was heated under reflux for 2 minutes, cooled to 25 ° C. with an ice bath, and then 625 ml of a 2% sodium bicarbonate solution was added. The solution was saturated by adding 23 g of sodium chloride and extracted with methylene chloride (1 × 200 ml and 3 × 100 ml). After drying over sodium sulfate, the methylene chloride was removed in vacuo to give 142 g of crude cis-3-hexene-2,5-dione. Gas-liquid chromatography revealed approximately 90% product of the structural formula

O (Y

The (2,5-dimethyl-3-furyl) propyl sulfide according to the invention had a molecular weight of 170. The MS analysis showed:

Relative intensity

27

39

41

43

85

95

127

128

ml70

18 21 20 10 (1 17 28 30 59 42

This compound had a pleasant onion-like, sulphurous aroma and a pleasant fleshy, sulphurous taste.

Example 3

Preparation of Isoamyl (2-methyl-3-furyl) sulfide reaction:

+ After ₃

CH ₃ OH SNa

+ Br

A solution of 0.005 mol (0.57 g) of 2-methyl-3-furanthiol dissolved in 3 ml of methanol was added to a solution of 0.27 g (0.005 mol) of sodium methylate in 3 ml of methanol. The resulting yellow solution was stirred for 10 minutes and then 1-bromo-3-methylbutane (isoamyl bromide) (0.005 mol) in 1 ml of methanol was added dropwise over a period of 2 minutes. This reaction mixture was refluxed at 63 ° C. for 9 hours.

The reaction mass was then cooled to 25 ° C. and then 10 m! Water added. The mixture was neutralized to pH 6 with 4% hydrochloric acid and then 10 ml of hexane were added. The organic phase formed was separated off and the aqueous layer extracted with 6 ml of η-hexane. The organic phase and the hexane extracts were removed and washed with saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 0.60 g of a crude oil. A sample of isoamyl (2-methyl-3-furyl) sulfide was isolated from the oil by gas-liquid chromatography (chromatography conditions: 8 "χ" column, 25% SE-30).

The MS, NMR and IR analyzes confirmed this Structural formula

The compound had a molecular weight of! 84. The MS analysis showed:

Relative intensity

36 ⁴ 21 20 3O ⁵ 92 ² 21 17 25 ⁶ 100 '

1 (1

This compound had a sweet, meat-like aroma reminiscent of baked bread with liver nuances and a green, sweet, yeast-like seasoning reminiscent of hydrolyzed vegetable protein with baked bread, hazelnut, liver, sulfur and pecan reminiscent nuances.

The 3-furylalkyl sulfides according to the invention were in a column chromatography coated with silicone «. The oil obtained after cleaning was with injected into a gas-liquid chromatography device using a needle. Like the oil through the pillar migrated, different compounds were absorbed at different points on the very narrow column. After the injection was completed, the substances accumulated in the column were recovered one by one, by purging the column with an inert gas. This method was used in the laboratory applied In industrial production, however, distillation processes are used

The following are some application examples for the 3-furylalkyl sulfides according to the invention indicated.

Application example 2

A beef liver sauce was made from the following ingredients:

Components Weight parts Corn starch End product from example 4 Caramel color Garlic powder White ITerrer

Monosodium glutamate

10.50 3.00 0.30 0.05 0.05 1.92 0.20

To one unit of the sauce flavor concentrate was added 2.261 of water and the mixture mixed carefully to disperse the ingredients. Then was heated to boiling and then Lightly cooked for 1 minute. This "meatless" sauce had an excellent, uniquely sweet meat flavor.

Application Example 3 Use before (2-methyl-3-furyl) methyl sulfide

(2-Methyl-3-furyl) methyl sulfide was added to meat broth, which had been prepared from a commercially available dry mixture and 250 ml of hot water was. The final concentration of sulfide was 3 ppm. This connection enhanced the meat and sweetness nutty character and enhanced the boullion-like note. The broth obtained was better more rounded meat flavor than the unseasoned meat broth.

Application example I

The following components were refluxed for 4 hours:

Application example 4 The following preparation was made:

Components Parts by weight Components Parts by weight L-cysteine hydrochloride

carbohydrate-free vegetable protein hydrolyzate

Thiamine hydrochloride water

0.9
30.9

0.9
67.30

The mixture was aged three days and then one small sample taken and dried based on the weight of the dry solid was added to the Mass enough gum arabic added to make a composition with a content of 1 Part by weight to form gum arabic. This mass was then spray dried

Methyl- (2-methyl-3-furyI) -sulfki was added to the spray-dried product in a concentration of 10 ppm added.

The obtained composition had an excellent, uniquely sweet meat seasoning,

60

65

Liquid 90 hydrolyzed vegetable protein

4-methyl- / I-hydroxyethylthiazole 5

Tetrahydrothiophen-3-one 1 Furfuryl mercaptan 0.01

2-nonenal 0.50

Difurfuryl disulfide 0.49 Dimethyl sulfide 0.50 Methyl mercaptan 0.50

(2,5-Dimethyl-3-furyl) propyl sulfide 2.00 produced according to example 2

The (23-dimethyl-3-furyl) propyl sulfide had a sweet intertwining effect and gave a meaty onion-like taste, which is reminiscent of the “Irish Stewa-Gesehmack leaned on it. This connection helped the typical taste of the hydrolyzed

Cut down on vegetable protein and brought the other meat-like chemicals in the preparation in accordance and rounded them off.

Application example 5

Use of (2,5-dimethyl-3-furyl) propyl sulfide

(2,5-Dimethyl-3-furyl) propyl sulfide became a Given meat broth, which is made from a commercially available dry product and 250 hot water had been. The final concentration of sulfide was 4 ppm. It gave the meat broth an "Irish stew" - Character and enhanced the onion note. The meat broth obtained had a better, more rounded one Meat seasoning than the unseasoned broth.

Application example 6

The following basic mixture for sausage was produced:

Components (ieuichtstcile Ground beef 200 Beef tallow 120 Ice / NaCl (5O: 5O-Geniisch) 200 potato flour 100 Anhydrous breadcrumbs 140 Dry milk powder 20th Standard spice 10 containing: Caraway seed oil 1.6 Mustard oil 3.3 Celery oil 3.3 Ginger oil 5.2 Clove oil 14.3 Coriander oil 17.6 Allspice oil 22.0 Black pepper oil 43.0 Oleoresin capsule 373.0 Nutmeg oil 500.0

Components

Weight parts

To this mixture was added 0.02% by weight of the following composition:

Isoamyl (2-methyl-3-furyl) sulfide 5

manufactured according to example 3

Ethyl alcohol 95

The mixture obtained was incorporated into a sausage mass and this in the usual manner into a Sausage casing filled. The sausage produced in this way was heated in water at a temperature of 71 ° to 82 ° C and kept at this temperature for two hours. the

ι, finished sausage had a sweet liver taste that reminded of sausage made with natural liver.

Application example 7

: m A mixture of 8.8 g of cysteine hydrochloride, 8.8 g Thiamine hydrochloride and 309.4 carbohydrate-free vegetable protein hydrolyzate were obtained by adding Bring water to a standard weight of 1000 g and add acid or base - as required - to one

y, pH 4.75 adjusted. This mix turned out to be four Boiled under reflux at atmospheric pressure for hours and then allowed to cool.

After cooling, 0.001 g of isoamyl (2-methyl-3-furyl) sulfide, prepared according to Example 3 added. The mixture obtained had an excellent unique sweet, liver-like and meat-like seasoning with baked bread and hazelnut reminiscent Nuances.

ii application examples

Use of Isoamy! - (2-methyl-3-furyl) sulfide

isoamyl- (2-methyl-3-furyl) sulfide was added to a meat broth made from a commercially available

4Ii dry product and 250 ml of hot water. The sulfate was present at a concentration of 2 ppm. The sulfide enhanced the sweet, meaty and liver-like character and gave it a nutty note. The ^lT meat broth seasoned with it

4i had better rounded meat flavor than that unseasoned broth.

Claims (2)

Claims; 1,3-furylalkyl sulfides of the general formula CH ₃ wherein Ri is a d- to Cs-alkyl group and R _{2 is} hydrogen or the methyl group. 2. Use of the 3-furylalkyl sulfides according to claim 1 as a seasoning for food