DE2042178B - Flavor or fragrance composition for food - Google Patents

Description

contains, in which R ₁ or R, a primary or secondary hydroxyalkyl group which has 1 to 6 carbon atoms, or a corresponding acylated primary or secondary hydroxyalkyl group (acid component derived from an alkanecarboxylic acid C to C _fi ) and the other group is hydrogen or an alkyl group with 1 to 6 carbon atoms, the dashed lines represent single bonds or nonadjacent double bonds and that the molecule can also be in the thiazolonium, thiazolinonium or thiazolidonium form, and

b) the rest of the auxiliaries customary in food chemistry or solvents for the compounds mentioned under a).

Food industry the subject of extensive research. The lack of food, in particular of protein foods in many parts of the world, the need has shown sources for To tap into protein that is not meat, and it is necessary to make such proteins as palatable as possible.

Furthermore, there will be a lot of fish. Poultry or meat containing or derived from meat

ίο Food in preserved form, for example in condensed soups, dry soup mixes, dry meat preparations, freeze-dried or lyophilized meat preparations, packaged gravies and the like. Although this

5 products contain meat or meat extracts the smell, taste and other organoleptic factors often result from the processing measures deteriorated, and it is desirable to taste or to supplement the scent of these preserved meat, poultry or fish foods or to improve.

The present invention is a flavor or fragrance composition for food, which is characterized in that it

a) 0.001 to 10 percent by weight of the total composition of a thiazole derivative of the formula

R, -r -N

Artificial flavorings for food have gained increasing interest in recent years. In many fields, such food flavorings are preferred over natural flavorings, at least in part therefore, wci! you can achieve a uniform taste in this way. For example, natural flavorings vary for foods such as extracts, essences. Concentrates and the like are often very strong because of differences in their quality, their type and in the treatment of the raw materials. Such variations are in the final products recognizable and give unreliable taste characteristics. Furthermore, the presence of a natural product may be undesirable in the end food because of the tendency to Corruption is increased. This is especially true for foods intended for, convenience and for small Snacks are made with products such as dips or sauces for dipping. Soupiv. Crisps. Ready meals. Canned food. Sauces and gravies used by the consumer before they are used be stored for some time.

In the production of flavorings or compounds it is therefore a goal to reproduce fragrances and flavors as closely as possible to nature / u reach. This is generally calloused, since the mechanism of smell and taste development is not known in many foods.

Reproduction of meat. Chicken and fish snacks and aroma has been around for a long time

contains, in which R, or R ₂ a primary or secondary hydroxyalkyl group which has 1 to 6 carbon atoms, or a corresponding acylated primary or secondary hydroxyl alkyl group (acid component derived from an alkanecarboxylic acid C ₁ to C ₆ ) and the other group is hydrogen or an alkyl group with 1 to 6 carbon atoms means, the dashed lines represent single bonds or nonadjacent double bonds and the molecule also in the thiazolonium. May be thiazolinonium or thiazolidonium form, and

b) the remainder of the auxiliaries or solvents customary in food chemistry for those mentioned under a) Links.

The thiazole derivative bonds mentioned can be used alone or together with other known flavor components as they will be described later, used to flavor, taste-enhancing To deliver compositions and new foods.

The above formula includes thiazole derivatives the formula

Thiazoline derivatives of the formulas
R ₁ -τ N

and thiazolidine derivatives of the formula

worm R, Lind R _{2 have} the meanings already given. "

F- are preferably used according to the invention compounds which methvl as alkyl groups. Ethy! or contain propyl. In certain preferred items according to the invention Embodiments, the hydroxyl group is a substituent on the / ^ - carbon atom, > o that. when 3 or more carbon atoms in the H> droxynlkylgruppe are present, the hydroxyl group is secondary. If the hydroxyl group is not there 111 of the - position, it is preferred that it be in the omega position that is, at the farthest end of the hydroxyalkyl chain.

In the esters according to the invention, the acetoxy and propionoxy groups are preferred acyloxy groups.

Thiazole derivatives. which can be used. include:

4-Me th> l-5- (beta-hvdroxyäthvl) -thiazoi.

4-M ethvl-5- (heta-acctoxyethyl) -thiai: ol.

4-Ai h> l-v (beta-hydroxyethyl) -thiazole.

4-propyl- (2) -5- (beta-hydroxyethyl) -thiazole.

4-But_vl-5- (beta-hydroxyethyl) -thiazole.

4-methyl-5- (hydroxymethyl) thiazole.

4-Meihvl-5- (heia-hydroxypropyl) -thiazole.

4-propyl- (2) -5- (beia-hydroxvhutvl) -thiazo |,

4-PeiHyl- (3) -5- (beta-hydroxybut \ l) -thiazole.

4-hexyl-5- (zeta-hydroxyhexyl) thiazole.

4-ethyl-5- (gamma-acetoxypropyl) -thiazoi.

4-Athvl-5- (beia-propanoyloxyäthvl) -thiazoL

4-Propyi-5- (propanoylox \ me! Hyl) -ihiazole.

4-Aiiivl-5- (epsiloii-butanoylo \ ypentyl) -thiazole.

4-methyl-5- (heta-pentanoyloxyethyl) -thiazole.

40

45

Hie 1 hiaz.oldeiivate can be produced by a number of reaction steps. The preparation of 4-alkyl-5-hydroxylthiuzolen is described, for example, in US Pat. No. 2,130,570, and Huchma et al. describe syntheses of thia / ols in .1. Amer. former Soc. 67. p. 395 (1945).

The methods and compositions according to the invention Foods can have a great variety of flavors. Scent notes and / or Give aroma. Experts know: because "fragrance and aroma of food often influence each other so that both work together and that Product a single overall organoleptic impression to lend. Accordingly, the methods and compositions of the present invention can change, modify, amplify both the smell and the taste and aroma of food or vary.

The inventive thiazole derivatives can be used to prepare foods, when cooked, roasted, baked or otherwise heated or prepared for consumption, the desired nutritional flavors or aromas to lend freshly baked. So it is possible. Compositions to manufacture the Contain thiazole derivatives and which reveal a fresh bread aroma during baking.

Many of the thiazole derivatives used in the present invention allow them to be in relatively small amounts Quantities can be used to enhance the taste of materials that are intended for consumption improve, change, strengthen or vary. When trying to get a group of Used 20 examiners to assess the taste and aroma, the average discovered of the group members an odor improvement by 4-meth.yl-5- (beta-hydroxyethyl) -thiazoI in \ väIriger Solution at a level of 0.25 ppm and a taste enhancement at a level of 0.09 ppm. Unless otherwise stated, all parts are percentages. Percentages and ratios as weight specified.

The exact minimum concentration for the continuum Thiazole derivatives depends on the product, in which they are examined. \ on the particular thiazole derivative or the combination of thiazole derivatives. the temperature at which the test was carried out will, and similar factors. It exists also between different people em subjective difference in their ability to improve .Ui discover, and the particular threshold can be determined by the state of health of the person, whether and which materials were previously tested or used and the like are influenced. However can obtain very good results according to the invention under the conditions given below "earth.

The methods and compositions that follow provide a variety of good food tastes. like taste after meat. Poultry including chicken and turkey, freshly cooked fish, baked goods Taste including bread and rolls. The range of flavors will be by the concentration used, by the product, in which it is used and which varies the particular fhiazole derivatives.

The present invention provides compositions to foods including liquids that are consumed for consumption such as soups and meat broths and other beverages to impart good taste. The thiazole derivatives can be used on their own, as ingredients for flavor compositions and around the flavors of food alone or together with other additives, too vary, change, modify or improve. In some cases, if only a single taste impression if desired, the thiazole derivative or the thiazole derivatives may be added alone and they become one product in essence give a single taste and aroma impression.

2

The thiazole derivatives according to the invention are used with auxiliaries or solvents which are customary in food chemistry combined. Such auxiliaries are z. B. water. Ethanol, propylene glycol, glycerin. Porter peat like gum arabic and tragacanth, to make bases for spray-dried or other solid flavor compositions to deliver. They also include thickeners such as alginates and Carrageenan, meat sauces and similar products To give more content: Ingredients and spices such as salt, pepper, clove pepper. Basil. Capsicum extract ;. Cloves, diacetyl. Eugenol. Garlic oil, onion oil. Wood vinegar. Sage oil. Sodium citrate. Thyme, hydrolyzed vegetable protein: means for encapsulation: colorants like the approved ones Paints for food. Medicines and cosmetics, herbal paints and Karjmel: others Flavor materials required to make the to give the desired taste impression. Agents that increase the intensity of the taste, such as Mononittriumgiuiamat and different nucleotides: miuei. that keep freshness, and antioxidants like Ascorbic acid. Propyl gallate, butylated hydroxyanisole and butylated hydroxyl toluene.

The thiazole derivatives according to the invention can be used in Foods such as soups and soup mixes. Casserole dishes, canned vegetables and in frozen vegetables, in animal foods and in foods for pets, in foods for children. Sauces. Gravies. Meat broths. Slews, counterfeit meat product ^ dietetic Products. Meat spreads. Sauces for dipping. Bakery products and substitutes or tonics for meat extracts to be incorporated.

The following examples illustrate the invention. ^3S

example 1

The following ingredients are mixed homogeneously ^{at? .5 C C:}

40 constituent parts

Vegetable cooking fat 622.7

Salt 321.7

Glutamic acid 5.1

ι -Cysteine hyorochloride 10.3

Glycine '. 5.1

beta-alanine 1.3

Taurine 20.0

Mixture of disodium inosinate and

Disodium guanylate 3.3

5-propyl-4- (beta-hydroxyethyl) thiazole 10.3

The mixture was heated to 149 ° C over 30 seconds. After cooling to 37.8 "C were ■ 0.12 part of diacetyl and 0.10 part of hexanol were added. The resulting mixture had an excellent * Chicken smell or taste.

Example 2

The following muieiiaiien became croissants at 25 C. mixed:

Components parts

Vegetable cooking fat 622.7

Salt 321.7

Glutamic acid 5.1

ι -Cysteinhvdrnchlorid iu.3

Glycine 5.1

beta-alanine 1.3

178 I.

Components parts

Taurine 20.0

Mixture of disodium inosinate and

Disodium guanylate 3.3

The mixture was heated to 149 ° C. for 30 seconds. After cooling to 37.8 "C, O.12 parts Diacetyl and 0.10 parts of hexanal were added. After aging the resulting mixture for three hours 10.3 parts of 5- (hydroxymethyl) -4-propylihiazole added.

The resulting mixture is aged for 10 hours, leaving a material with an excellent chicken odor or taste.

Example 3 Components parts

Vegetable cooking fat 622.7

Salt 321.7

Glutamic acid 5.1

i.-cysteine hydrochloride 10.3

Glycine 5.1

beta-alanine 1.3

Taurine 20.0

Mixture of Dinairiuminosinai and

Disodium guanylate 3.3

4-methyl-5- (beta-hydroxyethyl) -thia7ol 10.3

The mixture was heated ^{to 149 ° C. within 30 seconds.} After cooling to 37 ° C., 0.12 part of diacetyl and 0.10 part of hexanal were added.

The resulting mixture had an excellent chicken taste.

Example 4

The following ingredients were mixed homogeneously at 25 ° C:

Components parts

Vegetable cooking fat 622.7

Salt 321.7

Glutamic acid 5.1

1-cysteine hydrochloride 10.3

Glycine 5.1

beta-alanine 1.3

Taurine 20.0

Hybrid of disodium inosinate and disodium guanylate 3.3

The mixture was heated to 149 ° C. for 30 seconds. After cooling to 37.8 ° C, it became 0.12 parts Diacetyl. 0.10 parts of hexanal and 10.3 parts of 4-methyl-5- (beta-hydroxyethyl) thiazole added.

The resulting mixture keeps an excellent chicken taste.

Example 5

The following ingredients were mixed homogeneously at C:

Components parts

Vegetable cooking fat 622.7

Salt 321.7

Glutamic acid 5J

i.-C "ystcinh \ droehlorid 10.3 ·

Glycine 5.1

beta-alanine 1.3

Taurine 20.0

Mixture of disodium inosinate and disodium eeuanvlate 3.3

The mixture was ^{heated to 149 °} C. over 60 seconds. After cooling to 37.8C, 0.12 part of diacetyl and 0.10 part of hexanal were added. The mixture was aged for three hours at 18.3 ^C C. and then 10.3 parts of 4-methyl-5- (beta-hydroxyethyl) thiazole were added. The resulting mixture was then aged for 10 hours to give a composition exhibiting excellent chicken taste.

IO

Example 6

Cysieinhydrochlorid g is in an amount of 8.8 heated at 52 ^C C and atmospheric Diuck 4 hours a mixture of 309 g of hydrolysed plant protein and 674 g of water at reflux. The mixture is then cooled and 8.8 g of 4-methyl-5- (beta-hydroxyäthyi) -ihiazole are added and mixed well with the composition. The resulting mixture had an excellent beef smell or taste.

Example 7

5-methyl-4- (beta-acetoxyethyl) -thiazol be g in an amount of 8.8 heated at 103 C under ^r atmoshährischem pressure for 4 hours with the following previously mixed composition at reflux:

Example 10

Components parts

Hydrolyzed vegetable protein ... 309 g
Water 674 g

After the mixture was refluxed, the resulting mixture became 72 hours aged at 60 to 65 ° C. The mixture had an excellent beef flavor and smell of beef.

Examples

³⁵

8.8 g of 4-Metnyi-5- (beia-hydroxyäthyl) -thiazoi are refluxed at 103 ⁰ C under atmospheric pressure * hours with the following previously mixed composition: ₄₀ 25 ° C mixed:

The composition prepared according to Example 6 is dissolved in propylene glycol to form a 0, l ° / _o solution. This solution is added in an amount of 0.966 g to 7.3 g of a soup base, which contains:

Components parts

Finely ground sodium chloride .... 35.62 Hydrolyzed vegetable protein ... 27.40

Monosodium glutamate 17.81

Cane sugar 10.96

Beef fat 5.48

Caramel color 2.73

The resulting mixture is added to 340 g of boiling water, making a soup with an excellent Gets chicken flavor.

If the composition of Example 3 (0.005 g) is added to the above soup base, the result is you also have a soup with a good meat flavor.

Example 11

Half a gram of the soup base mixture from Example 9 is emulsified in a solution containing 100 g of gum arabic and 300 g of water. The emulsion is spray-dried to give 70.8 m ³ of air per minute is used with an inlet temperature of 260 ⁰ C and an outlet temperature of 93 ⁰ C and a wheel speed of 50,000 revolutions per minute.

12 g of the spray-dried material are mixed with 29.2 g of soup base, as described in Example 7, mixed. The resulting mixture is added to 340 g of boiling water and one is obtained Soup with an excellent meat flavor.

Example 12a The following ingredients were homogeneous

Components parts

Hydrolyzed vegetable protein ... 309 g
Water "674 g

The resulting mixture was then aged at 60 to 75 ° C. for 72 hours. The mix had excellent beef flavor.

Example 9

The composition prepared in Example 1 is dissolved in propylene glycol, wherein a is 0, l ° / ₀ solution is prepared, this solution is an amount of 0.966 g in about 7.3 g of a soup base material optionally consisting of:

Components parts

Finely ground sodium chloride .... 35.62
Hydrolyzed vegetable protein ... 27.40

Monosodium glutamate 17.81

Cane sugar 10.96

Beef fat 5.48

Caramel 2.73

The resulting mixture is added to 340 g of boiling water to give a soup which Contains an excellent chicken taste.

When the composition of Example 7 is added to the above soup base, one obtains also a soup that has a good meat taste.

Components parts

Ethanol 98.89

5-ethyl-3-hydroxy-4-methy] - (2.5H) -di

hydrofuran-2-one 0.19

2-methyl-3-furan thiol 0.25

Bis (2-methyl-3-furyl) disulfide 0.25

4-M.ethyl-5- (beta-hydroxyethyl) thiazo I 0, z5

Lovage oil 0.06

2,4-pentadienal 0.03

2,4,5-trimethyl- / l ³ -oxazoline 0.08

The resulting mixture had an excellent hydrolyzed vegetable taste Piotein.

Example 12b

The combination according to Example 12a is prepared in a propylene glycol to form translation: dissolved 0.1 ° / _o solution. This solution is added in an amount of 0.966 g to 7.3 g soup base which contains:

Components parts

Sodium chloride '35.62

Monosodium glutamate 17.81

Hydrolyzed vegetable protein ... 27.40

Cane sugar 16.44

Caramel color 2.73

The resulting mixture is added to 340 g of boiling water to give a soup which excellent vegetable protein taste

Example 13

50 mg of 4-methyl-5- (beta-hydroxyethyl) thiazole are mixed with 20 ml of propylene glycol. To a

A portion of 227 g of a vegetable soup mixture in cans, which is commercially available, is added to 454 g of water and the mixture is heated to 70 ^° C. Then 1 ml of the propylene glycol is added. which contains the aforementioned thiazole was added. The soup is found to have a meat-like taste characteristic. which the vegetable soup made without thiazole doesn't have.

Claims (1)

Claim: Flavor or fragrance composition for food, characterized in that that they a) 0.001 to 10 percent by weight of the total composition of a thiazole derivative of the formula