Methods

Abstract

A method for preparing a pork flavor composition includes the following steps: a) providing a mixture of i) cysteine ​​and ii) acetoin; and b) reacting the mixture at a temperature of 30°C to 55°C to form a flavor composition; wherein the flavor composition comprises at least one or more compounds selected from 2,4,5-trimethyl-3-oxazoline, 4,5-dimethyloxazole, 2,4,5-trimethyloxazole, 2-methylthiazole, 4,5-dihydro-2-methylthiazole, trans- or cis-2,4,5-trimethyl-2,5-dihydrothiazole, 2-methyl-3-thiazoline, 2-acetyl-2-methyl-thiazoline, 2-isopropylthiazoline, 2,4,5-trimethylthiazole, and tetramethylpyrazine. The flavor composition is a meat flavor composition, particularly a ham and pork flavor composition.

Description

Technical Field

[0001] This invention generally relates to a method for preparing flavor compositions, particularly flavor compositions that contribute to the flavor of ham and pork. The invention also relates to novel flavor compositions comprising said flavor compositions, and further to consumer products, foods, and beverages comprising said flavor compositions.

[0002] background

[0003] Flavor compounds and compositions are known to be used in products such as food and beverages to improve their taste. However, there is still a need for new and improved flavor compounds and compositions.

[0004] This is, for example, in the field of plant-based products that are intended to mimic or replace meat. These products are based on plant-based ingredients with different properties, such as different aromas, flavors, and textures. To improve the properties of these products, compounds with meat-related flavors can be added. Meat flavoring agents can also be used in other products, such as bouillons, processed meats, or blends of meat and plant proteins.

[0005] The object of this invention is to provide a method for preparing a flavor composition that positively contributes to the overall flavor impression of food and beverages in which the flavor composition is incorporated. The flavor composition is a ham and pork flavor composition.

[0006] Overview

[0007] According to a first aspect of the present invention, a method for preparing a pork-flavored composition is provided.

[0008] According to a second aspect of the invention, a flavor mixture is provided comprising a pork flavor composition obtained by the method of the invention.

[0009] According to a third aspect of the invention, a product selected from food and beverages is provided, comprising a pork-flavored composition obtained by the method of the invention.

[0010] According to a fourth aspect of the invention, a method is provided for imparting, enhancing, improving, or altering flavor characteristics of flavor mixtures or consumer products.

[0011] Certain embodiments of any aspect of the present invention may provide one or more of the following advantages:

[0012] A feasible method for providing ham and pork flavored compositions;

[0013] Simple and readily available starting materials;

[0014] The resulting composition is suitable for vegetarian and vegan products;

[0015] The resulting composition has natural qualities.

[0016] Details, embodiments, and preferred embodiments provided with respect to any particular aspect or one of the described aspects of the invention will be further described herein, and are equally applicable to all aspects of the invention. Unless otherwise stated herein or obviously contradicted by the context, any combination of all possible variations of the embodiments, embodiments, and preferred embodiments described herein is included in the invention.

[0017] Detailed description

[0018] This invention is based on the surprising discovery that a pork-flavored composition can be provided by reacting a mixture of i) cysteine ​​and ii) acetoin. The pork-flavored composition is suitable for use as a meat-flavored composition, particularly a ham and pork-flavored composition.

[0019] Therefore, this article provides a method for preparing a flavor composition, which includes the following steps:

[0020] a) Provide a mixture of i) cysteine ​​and ii) acetoin; and

[0021] b) React the mixture at a temperature of 30°C to 55°C to form a pork-flavored composition;

[0022] The pork flavor composition thereof comprises at least one or more compounds selected from 2,4,5-trimethyl-3-oxazoline, 4,5-dimethyloxazolium, 2,4,5-trimethyloxazolium, 2-methylthiazole, 4,5-dihydro-2-methylthiazole, trans- or cis-2,4,5-trimethyl-2,5-dihydrothiazole, 2-methyl-3-thiazoline, 2-acetyl-2-methyl-thiazoline, 2-isopropylthiazoline, 2,4,5-trimethylthiazole, and tetramethylpyrazine.

[0023] The pork flavor composition has a flavor reminiscent of meat, particularly pork and sweet cooked ham. It can be obtained by a simple method, under mild conditions, and from readily available compounds.

[0024] In this paper, the terms “taste” and “flavor” are used interchangeably to describe the sensory effects perceived by the olfactory epithelium in the oral cavity, especially the tongue and nasal cavity.

[0025] Cysteine ​​(CAS No.: 52-90-4) is an α-amino acid found in food and can be obtained from animal-derived proteins such as keratin, or by fermenting plant-based raw materials in the presence of inorganic trace elements. Cysteine ​​can be used as is, or in the corresponding hydrochloride form, racemic form, enantiomer-enriched form, or enantiomerically pure form. For example, it can be used as L-cysteine·HCl (CAS No.: 7048-04-6).

[0026] Acetoni (3-hydroxybutanone, CAS No.: 513-86-0) can be obtained by chemical methods or by enzymatic fermentation of carbohydrates. It can be used in racemic, enantiomerically enriched, or enantiomerically pure forms.

[0027] For example, a mixture of cysteine ​​and acetoin consisting of racemic derivatives of two starting materials is provided.

[0028] Alternatively, the compound may be used in enantiomeric enrichment or enantiomeric purity.

[0029] For example, a mixture of L-cysteine·HCl and racemic acetoin is provided.

[0030] The pork-flavored composition obtained by the method of the present invention may contain a stereocenter, and the compound is a single isomer, such as an enantiomer or a diastereomer, or a mixture of more than one isomer.

[0031] For example, the pork flavor composition comprises at least one or more compounds selected from 2,4,5-trimethyl-3-oxazoline, 2,4,5-trimethylthiazole, and tetramethylpyrazine.

[0032] For example, the pork flavor composition comprises at least one or more compounds selected from 2,4,5-trimethyl-3-oxazoline, 2,4,5-trimethyloxazole, 2-methylthiazole, trans- or cis-2,4,5-trimethyl-2,5-dihydrothiazole, 2,4,5-trimethylthiazole, and tetramethylpyrazine.

[0033] For example, the pork flavor composition comprises at least three, at least five, or at least seven or more compounds selected from 2,4,5-trimethyl-3-oxazoline, 4,5-dimethyloxazolium, 2,4,5-trimethyloxazolium, 2-methylthiazole, 4,5-dihydro-2-methylthiazole, trans- or cis-2,4,5-trimethyl-2,5-dihydrothiazole, 2-methyl-3-thiazoline, 2-acetyl-2-methyl-thiazoline, 2-isopropylthiazoline, 2,4,5-trimethylthiazole, and tetramethylpyrazine.

[0034] In one embodiment of the invention, the pork flavor composition comprises 2,4,5-trimethyl-3-oxazoline, 4,5-dimethyloxazole, 2,4,5-trimethyloxazole, 2-methylthiazole, 4,5-dihydro-2-methylthiazole, trans- or cis-2,4,5-trimethyl-2,5-dihydrothiazole, 2-methyl-3-thiazoline, 2-acetyl-2-methyl-thiazoline, 2-isopropylthiazoline, 2,4,5-trimethylthiazole, and tetramethylpyrazine.

[0035] The pork-flavored compositions obtained by the method of this invention contain compounds that are heteroaromatic compounds comprising two heteroatoms selected from N, O, and S. The two heteroatoms in each compound may be the same or different.

[0036] The compounds obtained by the method of the present invention contribute to meat flavor, especially pork and dairy flavor.

[0037] In one embodiment of the invention, the mixture of i) cysteine ​​and ii) acetoin is reacted at a pH of about 3.9 to 4.1, preferably at a pH of about 4.0. The acidic reaction conditions impart a preferred flavor composition.

[0038] In one embodiment of the invention, i) a mixture of cysteine ​​and ii) acetoin is reacted in water.

[0039] Alternatively, the mixture may be reacted in water in the presence of an oil, such as high-oleic sunflower oil (sunflower oil high-oleic). Alternatively, the oil may be selected from MCT (medium-chain triglyceride) oil, coconut oil, peanut oil, olive oil, corn oil, or mixtures thereof, or other oils.

[0040] In one embodiment of the invention, the mixture i) cysteine ​​and ii) acetoin are reacted at elevated temperatures, preferably at 30°C or higher, even more preferably at about 40°C, or at a maximum of about 55°C. For example, the mixture is reacted at about 40°C to 42°C. However, the reaction temperature does not exceed 60°C. For example, the mixture i) cysteine ​​and ii) acetoin are reacted at temperatures between 30°C and 55°C, preferably between 35°C and 50°C, more preferably between 40°C and 50°C. At higher temperatures, the flavor characteristics lose their pork and ham characteristics and become a meaty flavor, closer to roast meat and / or beef.

[0041] In one embodiment of the invention, the mixture of i) cysteine ​​and ii) acetoin reacts for about 1 to 3 hours, preferably about 2 hours. For example, the mixture reacts for about 60 to 180 minutes, such as about 70 minutes, or about 80 minutes, or about 110 minutes or about 120 minutes.

[0042] Typically, the temperature and reaction time can be varied slightly depending on the overall size of the reaction mixture. For example, a mixture of i) cysteine ​​and ii) acetoin is reacted for 2 hours at approximately 40°C, 42°C, or 55°C in a reaction mixture of 3 to 70 L. In larger volumes, such as 1000 L to 2000 L, optimal reaction conditions can be adjusted. For example, a 1800 L mixture of i) cysteine ​​and ii) acetoin is reacted at 47°C for 70 min.

[0043] In one embodiment of the invention, cysteine ​​and acetoin are provided in a ratio of 1:5 to 5:1, preferably 1:2 to 2:1, for example, 1:1.75. With relatively high acetoin content, the flavor profile exhibits dairy characteristics. With relatively low acetoin content, the characteristic meaty characteristics, such as the sweetness and creaminess of pork and ham, are absent.

[0044] In one embodiment of the invention, the flavor composition is a pork and ham flavor composition. The pork and ham flavor composition can be mixed with other flavoring substances, flavoring mixtures, or compositions. It can also be added directly or mixed into consumer products.

[0045] As used herein, the term "flavoring substance" means any substance capable of imparting a detectable flavor effect, particularly at concentrations below 0.1 wt.%, more preferably below 0.01 wt.%. Such flavoring substances can be selected, for example, from natural flavorings, artificial flavorings, spices, seasonings, synthetic flavoring oils and aroma compounds and / or oils, oleoresins, flavorings, distillates, and extracts from plants, leaves, flowers, fruits, etc. Generally, any flavoring or food additive can be used, such as those described in *Chemicals Used in Food Processing*, Vol. 1274, pp. 63-258.

[0046] In another embodiment, the pork flavor composition obtained by the method of the present invention is particularly suitable for a variety of flavor blends and consumer products, especially delicious foods and beverages. In one embodiment, a flavor blend is provided comprising the pork flavor composition obtained by the method of the present invention.

[0047] For example, based on the total weight of the flavor mixture, the flavor mixture contains at least 0.01 wt.%, or at least 0.1 wt%, or at least 0.5 wt% of flavoring substances, and based on the total weight of the flavor mixture, contains 0.1 to 5 wt% of the pork flavor composition obtained by the method of the present invention, preferably 0.5 wt% to 2 wt.%, more preferably 0.7 to 1.6 wt.% of the pork flavor composition obtained by the method of the present invention.

[0048] In typical flavor blends, the pork flavor composition and seasoning substances obtained by the method of the present invention are used in a weight ratio ranging from 1:50 to 1:250, preferably from 1:60 to 1:150.

[0049] Flavor mixtures comprising pork flavor compositions obtained by the methods of the present invention can be suitably prepared in liquid, paste, or powder form. For example, the flavor mixture may be a free-flowing powder.

[0050] Typical examples of such flavor blends include delicious seasonings, especially meat seasonings or seasonings for plant-derived meat analogues, broths, processed meat or mixed meat plant protein acid / acidic seasonings, etc.

[0051] The pork flavor composition obtained by the method of the present invention can be used in flavor mixtures together with one or more ingredients or excipients commonly used in flavor mixtures, other than flavoring substances, such as carrier materials and other adjuvants commonly used in the art. Suitable excipients for flavor mixtures are well known in the art and include, for example, but not limited to, solvents (including water, alcohols, ethanol, oils, fats, vegetable oils, and miglyol), binders, diluents, disintegrants, lubricants, flavoring agents, coloring agents, preservatives, antioxidants, emulsifiers, stabilizers, flavor enhancers, anti-caking agents, etc.

[0052] Examples of such carriers or diluents for use in flavor blends can be found, for example, in "Perfume and Flavour Materials of Natural Origin", S. Arctander, Ed., Elizabeth, NJ, 1960; "Perfume and Flavour Chemicals", S. Arctander, Ed., Vol. I & II, Allured Publishing Corporation, Carol Stream, USA, 1994; "Flavourings", E. Ziegler and H. Ziegler (ed.), Wiley-VCH Weinheim, 1998; and "CTFA Cosmetic Ingredient Handbook", JM Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0053] Other suitable and desired ingredients for flavor compositions are described in standard texts such as “Handbook of Industrial Chemical Additives”, ed. M. and I. Ash, 2nd Ed., (Synapse 2000).

[0054] In another aspect of the invention, a consumer product is also provided, comprising a pork-flavored composition obtained by the method of the invention and a consumer product base.

[0055] "Product base" refers to the combination of all generally recognized ingredients required for a particular consumer product composition.

[0056] In another aspect of the invention, a consumer product selected from food and beverages is provided, the consumer product containing at least 10 ppm, preferably at least 50 ppm, more preferably at least 800 ppm or 10000 ppm of a pork-flavored composition obtained by the method of the invention.

[0057] For example, the product contains at least 0.007 wt.%, more preferably at least 0.015 wt.%, even more preferably at least 0.035 wt.%, and most preferably at least 0.1 wt.% of the pork flavor composition obtained by the method of the present invention. Typically, the above product will contain at a concentration of no more than 0.1 wt.%, preferably no more than 0.05 wt.% of the pork flavor composition obtained by the method of the present invention.

[0058] Typical examples of food products according to the invention include soups, sauces, broths, stock, broths, seasonings, noodles, chips, curls, meat products, plant-based meat analogs as alternatives to vegan meat, and beverages. Plant-based meat analogs are made from plant-based ingredients and are also referred to as plant-based meat, vegan meat, meat substitutes, imitation meat, meat substitutes, meat substitutes, or vegetarian meat. These products can be provided in the form of hamburger patties, sausages, cold cuts, patties, minced meat, steaks, chunks of meat, etc. Other examples include alternative proteins or non-animal proteins, including hybrid proteins, cell culture-derived products, insect proteins, or finely fermented proteins.

[0059] The pork flavor composition obtained by the method of the present invention can be advantageously used to impart the desired flavor properties to the above-mentioned products, thereby improving the overall flavor quality of these products.

[0060] In another aspect of the invention, a method is provided for imparting, enhancing, improving, or altering flavor properties to a flavor mixture or consumer product, the method comprising adding a pork flavor composition obtained by the method of the invention to the mixture or consumer product. For example, the pork flavor composition is added in an amount of at least 0.001 wt.%, preferably at least 0.007 wt.%.

[0061] The invention will now be further described with reference to the following non-limiting embodiments. These embodiments are for illustrative purposes only, and it should be understood that variations and modifications can be made by those skilled in the art.

[0062] Example

[0063] Example 1: Preparation of pork-flavored composition

[0064] Cysteine ​​and acetoin were dissolved in 7.0 g of water. The pH of the reaction mixture was adjusted by adding 30% NaOH aqueous solution. The reaction mixture was treated at a given temperature for a specified time.

[0065] The obtained flavor composition was tasted by a flavorist in warm water containing 0.3% NaCl at a concentration of 0.05%.

[0066] Table 1:

[0067]

[0068] The entries in the table above indicate that, generally, the flavor compositions provided have a meaty character. When the reaction temperature is maintained at around 50°C, specific pork and ham characteristics are obtained. At higher temperatures, such as 100°C, the flavor characteristics change to a general meaty character, and the pork and ham characteristics are lost.

[0069] The reaction of cysteine ​​and acetoin was carried out on a large scale at temperatures of approximately 40-55°C. The following components were identified in the final spray-dried product by GC-MS. The resulting flavor composition exhibits pork / ham characteristics. The main components of the final product are acetoin, cysteine, and cystine, and other compounds have been identified:

[0070] Table 2:

[0071]

[0072] For further comparison, entries 1 and 2 of Table 1 have been analyzed, with a focus on the five components listed below. These compounds are associated with pork flavor and / or meat flavor characteristics.

[0073] Table 3:

[0074]

[0075] In entry 2, which has a ham creamy flavor, the following compounds were not detected: 2,5-dimethyl-3(2H)-furanone, 2,5-dimethyl-furan-3-thiol, and 2,5-dimethyl-furan-3-thioacetate. They were either not present at all or present only in amounts below the threshold level of 1 ppm.

[0076] Example 2: Comparison with other flavors in vegan broth base

[0077] The following samples were prepared in a warm 0.3% sodium chloride solution:

[0078] A) Vegan broth base

[0079] B) Vegan broth base + 0.05% pork flavor composition from Example 1 and Experiment 1 (Table 2)

[0080] C) Vegan broth base + 0.2% diced bacon (lardon) flavoring

[0081] D) Vegan broth base + 0.2% diced bacon flavoring agent + 0.05% pork flavoring composition of Example 1 and Experiment 1 (Table 2)

[0082] The samples were tasted by a group of ten flavorists. The pork flavor composition of Example 1 was effective and was described as enhancing the cream and fat characteristics and making the flavor profile more meaty and rounded; it provided a sweet cooked ham characteristic.

[0083] Example 3: Impact on plant-based products

[0084] The pork flavor composition according to the present invention has been used in combination with other seasonings in the following plant-based products:

[0085] 1) Plant-based Italian Salami

[0086] Described as: cured ham, peppery, sour. Also has a spicy flavor.

[0087] 2) Plant-based coarse sausage

[0088] Described as: meaty, deep-fried, umami, and peppery.

[0089] 3) Plant-based Frankfurt sausage

[0090] Described as: smoky, buttery, and fatty pork. Additional comment: In the first few bites, it's difficult to tell if it's plant-based or genuine Frankfurt meat.

[0091] 4) Plant-based root slices

[0092] The flavor is described as smoky sweet, buttery, cured ham, bone marrow beef, and deep-fried with fat.

[0093] 5) Plant-based bacon blocks / bacon cubes

[0094] Described as: cooked pork, butter, smoky flavor, and umami flavor.

[0095] The pork flavor compositions of Examples 1 and 1 (Table 2) were present in the total flavor mixture at a concentration of 0.7-1.6%. In the final application, the concentration of the complete flavoring agent comprising the pork flavor compositions of Examples 1 and 1 (Table 2) was 1%-3.5%. Overall, the pork flavor compositions of Examples 1 and 1 (Table 2) provided a fatty pork flavor with a sweet, cooked ham-like character.

Claims

1. A method for preparing a pork-flavored composition, comprising the following steps: a) Provide a mixture of i) cysteine ​​and ii) acetoin; and b) React the mixture at a temperature between 30°C and 55°C to form a flavor composition; The flavor composition comprises at least one or more compounds selected from 2,4,5-trimethyl-3-oxazoline, 4,5-dimethyloxazolium, 2,4,5-trimethyloxazolium, 2-methylthiazole, 4,5-dihydro-2-methylthiazole, trans- or cis-2,4,5-trimethyl-2,5-dihydrothiazole, 2-methyl-3-thiazoline, 2-acetyl-2-methyl-thiazoline, 2-isopropylthiazoline, 2,4,5-trimethylthiazole, and tetramethylpyrazine.

2. The method according to claim 1, wherein the pork flavor composition comprises at least three, at least five, or at least seven or more compounds selected from 2,4,5-trimethyl-3-oxazoline, 4,5-dimethyloxazole, 2,4,5-trimethyloxazole, 2-methylthiazole, 4,5-dihydro-2-methylthiazole, trans- or cis-2,4,5-trimethyl-2,5-dihydrothiazole, 2-methyl-3-thiazoline, 2-acetyl-2-methyl-thiazoline, 2-isopropylthiazoline, 2,4,5-trimethylthiazole, and tetramethylpyrazine.

3. The method according to claim 1, wherein the pork flavor composition comprises 2,4,5-trimethyl-3-oxazoline, 4,5-dimethyloxazole, 2,4,5-trimethyloxazole, 2-methylthiazole, 4,5-dihydro-2-methylthiazole, trans- or cis-2,4,5-trimethyl-2,5-dihydrothiazole, 2-methyl-3-thiazoline, 2-acetyl-2-methyl-thiazoline, 2-isopropylthiazoline, 2,4,5-trimethylthiazole, and tetramethylpyrazine.

4. The method according to any one of the preceding claims, wherein the mixture is reacted at a pH of about 3.9 to 4.1, preferably at a pH of about 4.

0.

5. The method according to any one of the preceding claims, wherein the mixture is reacted in water, optionally in the presence of oil, such as high-oleic sunflower oil.

6. The method according to any one of the preceding claims, wherein the mixture reacts for about 1 to 3 hours, preferably about 2 hours.

7. The method according to any one of the preceding claims, wherein cysteine ​​and acetoin are provided in a ratio of 1:5 to 5:1, preferably 1:2 to 2:1, for example 1:1.

75.

8. The method according to any one of the preceding claims, wherein the flavor composition is a meat flavor composition or a pork flavor composition.

9. A flavor mixture comprising a pork flavor composition obtained by any one of the preceding claims.

10. The flavor mixture of claim 10, wherein the pork flavor composition comprises 0.001 to 0.02 wt% based on the total weight of the flavor mixture.

11. A consumer product comprising a pork-flavored composition obtained by the method of any one of claims 1 to 9 and a consumer product base.

12. The consumer product according to claim 12, comprising at least 700 ppb, preferably at least 1600 ppb, more preferably at least 3500 ppb or 8000 ppb of a pork-flavored composition obtained by the method of any one of claims 1 to 9.

13. The consumer product according to claim 12 or 13, wherein the consumer product is selected from food and beverages.

14. A method for imparting, enhancing, improving, or altering the flavor characteristics of a flavor mixture or consumer product, said method comprising adding a pork-flavored composition obtained by any one of claims 1 to 8 to said mixture or consumer product.

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