DE1803867C3 - Use of 2-hydroxy-3-methyl-4-ethyl-buten-2) -olide- (4, l) and a corresponding precursor compound - Google Patents

Description

for changing the taste and aroma of food for humans and animals, beverages and pharmaceutical preparations or
Use b) of the compound (II), which has been prepared by reacting 2-ketobutyric acid dissolved in benzene with dry hydrogen chloride, for changing the taste and aroma of foods for humans and animals and of beverages which are normally subjected to a heat treatment.

The invention relates to the use of the compounds shown in the preceding claim I and II. JO

Compound 1 is from HeIv. Chim. Acta 31 (1948), 473 and 40 (1957), 1983 known.

The above-mentioned lactone I is obtained by decarboxylating the acidic precursor II (preparation see below) by the action of heat. The conversion of the J ^r> precursor (acid) Il in the inventive lactone 1 can be carried out at temperatures above 50 ⁰ C. In order to increase the reaction rate, it is expedient to use temperatures of at least 100 ^° C., for example. According to a preferred embodiment, the conversion of the acid II into the lactone I is carried out at temperatures in the vicinity of the melting point of the precursor or at a temperature which is higher than its melting point. The heating time is variable and can e.g. B. some 4 ^r > seconds if the transfer is carried out at high temperatures in a pyrolysis apparatus, or several hours, e.g. B. 24 hours when working at lower temperatures. Long reaction times should be avoided at the higher reaction temperatures so that the reaction products do not char.

If the acidic precursor II is incorporated into foods or beverages, in the course of their Manufacture or before consumption a heat treatment, such as. B. Boiling, cooking or baking, are subjected, the conversion of the precursor II into the lactone I takes place easily with the for this Heat treatments used temperatures.

The acid II used as the starting material is obtained by heating 2-ketobutyric acid in the presence of a strong acid, preferably a mineral acid, or a mixed mineral-organic acid according to obtained from the following reaction scheme:

50 The putative formula of (II) is
H

C = O

, —C

HOOC

id (see: Reports of the German chemical Society 35 (1902), 1625 and J. Food Sa 52 [1967], 614).

Strong acids that can be used are, for example, hydrogen chloride, perchloric acid, phosphoric acid, sulfuric acid, trifluoroacetic acid or p-toluene sulfonic acid. It is advantageous to use dry gaseous hydrogen chloride and to carry out the reaction in benzene at room temperature. However, you can also work at other temperatures, e.g. B. at those from 0 to 80 ⁰ C or above, and other common solvents, such as. B. tetrahydrofuran, dioxane, toluene or chloroform, use.

In a suitable dilution, the 2-hydroxy-3-methyl-4-ethylbutene- (2) -olide- (4, l) To give a maple-like taste to food, beverages and pharmaceutical preparations. In food and drinks can be used, for example, in amounts of 0.1 to 50 parts by weight of the lactone per each

I million parts by weight of food or drink can achieve the desired taste effect. That Lactone is suitable, for example, for flavoring baked goods, syrups, sugar confectionery, ice cream and non-alcoholic beverages.

To achieve special taste effects, the lactone can also be mixed with other flavorings mix.

In the following experiment and in the examples, the temperature is given in degrees Celsius.

attempt

Preparation of 2-hydroxy-3-methyl-4-ethylbutene- (2) -olide- (4, l)

a) Production of the precursor II

In a solution of 1387.7 g of a-ketobutyric acid in 1338 g of benzene were at 20 ° over the course of 7 hours Introduced 135 g of dry hydrogen chloride. That The reaction mixture was left on its own at room temperature overnight. The resulting crystals were suction filtered and the aqueous layer of the filtrate was decanted off. In the remaining Benzene solution formed a further quantity of crystals in the course of a few hours, which again suctioned off became. The total weight of the connection received

I1 was 1166.5 g, m.p. 152-154 ° (dec.).

b) Preparation of 2-hydroxy-3-methyl-ethyl-buten-2) -olide- (4, l)

186 g of the compound obtained according to a) were heated at 160 ° until the evolution of CO ₂ ceased. The reaction product was distilled, 130.7 g of lactone, bp 70-71 ° / C 0.003 Torr, melting point 21 °, being obtained.

2CH ₁ -Cl ₂ -CO- COOH

Η " ¹

example 1

to ^v

An artificial maple aroma was produced by adding the substances listed below (II) were mixed:

Components

Parts by weight dose

Food or drink

Fenugreek seed extract

Ethyl vanillin

Methylcyclopentenolone

Propylene glycol

Total

200

20th

10

750

980

To 980 g of the mixture described above, 20 g of 2-hydroxy-3-methyl-4-ethyl-buten- (2) -olide- (4, l) were added. The product obtained is referred to below as “Aroin A”. A second portion of 980 g of the mixture described above, 20 g of propylene glycol was added to obtain a comparative product to obtain, which is referred to in the following with "Arom B"

"Arom A" and "Arom B" were each in a portion of a sugar syrup in a proportion of 100 mg Flavor incorporated per 1 kilogram of syrup. The sugar syrup was made by dissolving 6.5 kg of sucrose in 3.81 warm water, boiling the solution for 2 minutes and cooling the obtained Liquid has been produced.

The two flavored syrup samples were submitted to a panel of several taste panelists for evaluation The taste of the syrup sample containing "Aroma A" was found to be specifically maple-like and, compared to the taste of the syrup sample containing "Aroma B", it is more rounded and natural judged.

Example 2

A maple aroma was created by mixing the following substances:

Components Weight in g ■ 2-Hydroxy-3-methyl-4-ethyl-bulen- (2) - 1 Vanillin 9 Coffee extract in solid form 30th ■ Licorice extract in solid form 30th ·. Marrubium extract in solid form 5 > Propylene glycol 460 { Water 465 ] Total 1000

The flavor described above has been used in the foods and foods listed below To give drinks a maple-like aroma. The flavor was used in the following doses.

100 g syrup 150 g Hard candies 100 s Ice cream 200 g cake 80 g pudding

The above foods and beverages were produced as follows:

syrup

Manufactured in the manner described in Example 1.
Hard candies

100 ml of syrup and 20 g of glucose were mixed and slowly heated to 145 °. After adding the flavor left you can harden the mass by cooling it.

Ice cream

The ice cream was made from 1 liter of milk, 5 egg yolks and 250 g of sugar by mixing the sugar with the Egg yolks were mixed and the hot milk was added to the mass, stirring until the mass was smooth and gradually becoming thick.

cake

ω A cake mixture was made by processing 100 g of vegetable margarine, 1.5 g of sodium chloride, 100 g sucrose 2 eggs and 100 g flour are made. After incorporating a flavor into the mass obtained became the latter for 40 minutes at 180 °

π baked.

pudding

500 ml of hot milk were stirred with a

Mixture of 60 g sucrose and 3 g pectin mixed. The mixture became for a few seconds cooked. After adding the aroma, the mass was allowed to cool.

Example 3

4 ", According to the method given above, a Pudding using 200 g of the compound of formula 11, per 100 kg of food, flavored. The taste of the food thus obtained was identical to that of the food that is associated with the

■> n Formula I was flavored. The compound of formula II was prepared according to that described in paragraph: a) Attempt made.

The exploitation of the invention can be made possible by legal provisions, in particular the Food Act, be limited.

Claims (1)

Claim:
Use a) of the compound of the formula CH ₃ -C =
CH ₃ -CH ₂ -C = C = OH CO U)