DE1793631C3 - 2,5 dimethyl 3 methoxy 4 oxo 4,5 dihydrofuran and flavoring agents that contain this compound excreted from 1517023 - Google Patents

Description

The preparation of 2,5-dimethyl-3-methoxy-4-oxo-4,5-dihydrofuran is described in example 1.

The invention relates to 2,5-dimethyl-3-methoxy-4 °. .

4-oxo-4,5-dihydrofuran and flavoring agents B e ι s ρ ι e

for food or beverages containing a solution of 5 g of 2,5-dimethyl-3-hydroxy-4-oxo-

this connection. 4,5-dihydrofuran in 10 ecm of methanol was combined with a

The term "food" also includes excess diazomethane ethereal treated herein. Enjoyment center !. 45 The reaction was instantaneous. After 1 hour

Even very small amounts of the new dihydrofuran, the reaction mixture under reduced compound would suffice to be concentrated in food or pressure, whereupon the residue distilled drinks became a strawberry-like taste effect. 3.1 g of 2,5-dimethyl-3-methoxy were obtained. These amounts can be used in certain 4-oxo-4,5-dihydrofuran with a boiling point of 0.4, 42 ° C.
Limits fluctuate, and they are, for example, 5 °.

0.5 to 50 parts by weight for every 1 million parts by weight Example

Food or drink. Most of the time, 1 was made of 1 milk, 5 egg yolks and 250 g of fine sugar

1 to 20 parts by weight of the flavor on each ice cream produced by boiling the milk with the 1 million parts by weight of the food or sugar mixed egg yolks with the milk and Beverage achieved good results. 55 the mixture was further cooked over a low flame.

You can add the strawberry flavor to food until the mass has thickened enough. The crowd Even more natural fidelity was added to foodstuffs and drinks, then poured through an injection sieve and cooled, borrow by adding 2,5-dimethyl-3-methoxy- After adding the aroma, the mass in the ice-4-oxo-4,5-dihydrofuran still (V-methylbutyric acid and machine ready-made.

optionally a lower Alkylesler this acid, 6o as flavor used was a 0.5 ° / _n solution of 2,5-Diz. B. the methyl or ethyl ester is used. A methyl-S-methoxy ^ -oxo ^ S-dihydrofuranin triacetin. You can get a pretty lifelike strawberry aroma.
of 2,5-dimethyl-3-melhoxy-4-oxo-4,5-dihydroΓuran, the finished ice cream was several experimental

x-methylbutyric acid and r-x-methylbutyric acid cmctliyl- 65 people are given at the expense of finding out esters in the proportion of 25:20:30 by weight - what the taste of the ice cream had. All share generate. Subjects provided a strong one without hesitation

To produce a well-rounded strawberry-strawberry taste.

Example 3 to 6

In the table below are some flavoring agents indicated, except for 2,5-dimethyl-3-methoxy-4-oxo-4,5-dihydrofuran contain additional flavorings. These flavoring agents create a natural strawberry flavor in food and beverages approaching taste.

Example 3 Example 4 Example 5 Example 6

2.5-dimethyl-3-methoxy-4-oxo-4,5-dihydrofuran

Caproic acid

Ethyl butyrate

Λ-methylbutyric acid

Ethyl Λ methyl butyrate

Triacetin

The numbers in this table mean parts by weight.

25th
40
50

885

1000

50
40
50

860

1000

25th

20th

30th

925

1000

100

20th

30th

850

.000

Example 7

There was a strawberry flavor according to that of J. Mer o r y in "Food Flavorings", 1960, p. 187, described Method made. This aroma had the following composition:

Ethyl heptanecarboxylate 0.80 g

Birch bark essence 0.80 g

Undecalactone 2.10 g

Cinnamyl isobutyric acid 2.40 g

Ethyl vanillin 2.60 g

Maltol 3.00 g

Cinnamyl isovaleric acid 3.20 g

Dipropyl ketone 3.40 g

Diacetyl 6.00 g

Methyl amyl ketone 5.00 g

Ethyl valerate 21.20 g

Ethyl methyl phenyl glycidate 23.15 g

Lactic acid ethyl ester 43.20 g

Alcohol, 95 ° 100.00 g

Propylene glycol 783.15 g

1000.00 g

With this flavor, by diluting it with propylene glycol, the following flavoring agent A manufactured.

Parts by weight

Aroma according to Merory 100

Propylene glycol 900

Flavoring agent A 1000

A second flavoring agent (B) was made by adding a small amount of 2,5-dimethyl-3-methoxy-4-oxo-4,5-dihydrofuran to the aroma according to Merory and dilution with propylene glycol manufactured as follows:

Parts by weight

Aroma according to Merory 100

2,5-dimethyl-3-methoxy-4-oxo-

4,5-dihydrofuran 4

Propylene glycol 896

Flavoring agent B 1000

»Ο Then a portion of one according to example 2 produced ice cream flavored with flavoring agent A (ice cream I), and a second Flavoring agent B was added to a portion of the ice cream produced according to Example 2 (Ice cream II). Both flavoring agents were finished in a weight ratio of 200 g to 100 kg each Used ice cream.

Samples of the two types of ice cream 1 and II were then presented to 34 test persons for tasting.

The test subjects first had to find out What kind of fruit flavor the two types of ice cream I and II were flavored with, and secondly to say which of the two types of ice cream they preferred. 32 out of a total of 34 test persons

recognized the strawberry taste without hesitation. 28 of the 34 test persons preferred ice cream type II and stated that the latter had a more pleasant and rounded aroma. The strawberry aroma of the Ice cream type II was found by most of the test persons to be much more natural and characteristic

felt.

Example 8

An ice cream according to Example 2 was produced. One serving was made up by the addition of 2,5-dimethyl-3-methoxy-4-oxo-4,5-dihydrofuran flavored. The character of the ice cream was fruity with a typical strawberry taste. The ice possessed, however

also had a caramel-like character, so that the overall effect corresponded to what was used when it was used of strawberry jam could be expected.

A second portion was made by adding 2,5-dimethyl-3-methoxy-4-oxo-l, 5-dihydrofuran and the connections listed in the table. /. B. caproic acid, Ätliyl-vmelhylbulyrat, flavored. This resulted in an ice cream with a natural fruity taste; H. with the typical Fresh strawberry flavor. The best results were obtained using a mixture of all of them in the table of Example 7 obtained compounds.

Claims (4)

taste you can use additional flavors Patent claims: to help. For this purpose, the 2,5-D.methyl-3-methoxy-4-oxo-5,4-dihydrofuran is used together with 1. 2,5-DimethyI-3-methoxy-4-oxo ^, 5-dihydrofu- at least one of the following compounds is used: ran of the formula 5 _{a) Any} fatty acids containing up to 6 carbon atoms _{o nrH} contain, for example butyric acid, diethyl . ³ acetic acid, /% - methylbutyric acid, n-valenic acid, II isovaleric acid, isobutyric acid, caproic acid; · ■ b) Esters of the acids mentioned under a) with alkali _CH ο ΓΗ ¹⁰ "oils that contain up to 6 carbon atoms, ^{a 3} - for example the methyl, ethyl, n-propyl, , ₄ . . ■, r- v, _L -. isopropyl, η-butyl and isobutyl esters; 2. Food flavoring agents. _& Ζ _τ £ _{r zj} , _{t acid with} alkanols that contain up to or drinks, characterized in that it contains _{fi KohIenstoi} , _tome , for example that contains the compound according to claim 1. 15 methyl- ethyl- n-propyl-, isopropyl-, .i-butyl- 3. Flavoring agent according to claim 2, da- _and , ' _sobutyl . _It 's _te r of cinnamic acid; characterized in that there is an additional £ _a , _iphat i _sch en γ- and Λ-hydroxy- flavoring substance «-Methylbutyric acid carboxylic acids containing 8 to 12 carbon atoms and / or a lower alkyl ester of α-methyl-. , ■ ' contains butyric acid. _2C , " ^old ' ^un <ju" v " _n Πι -il 4. Flavoring agent according to claim 2 and 3, ^{e) Hexana} '' ^He * ^e "- ( ² > - ^a1 'Hexen- (3) -al. characterized in that it also min- The incorporation of 2,5-dimethyl-3-methoxy- contains at least one of the following compounds: 4-oxo-4,5-dihydrofurans in food or a) Lower fatty acids, which contain up to 6 carbon drinks using conventional methods, in particular having atoms · ² S through the use of edible solution or drink b) Esters of the lower fat thinners mentioned under a), e.g. B. alcohol or Triacet for the purpose acids with alkanols with up to 6 carbon dilution and uniform distribution of the atoms; flavors. c) Esters of cinnamic acid with alkanols with up to ^A »e foods and beverages containing more than 6 carbon atoms; ³ ° by means of natural or artificial flavors d) Lactones of aliphatic γ- or Ö-hydroxy- strawberry flavor can be flavored with the carboxylic acids with 8 to 12 carbon atoms, compound according to the invention, _oil j _he, for example, ice cream, creams, sugar confectionery, e) hexanal, hexen-2-al or hexen-3-al. fisery goods, yoghurt, milk drinks, syrups, carbon 35 acidic drinks. 2,5-Dimethyl-3-methoxy-4-oxo-4,5-dihydrofuran can also improve the taste of medicines.