Organic compounds

Abstract

The present disclosure relates to the use of compounds of formula (I) wherein R1 and R2 are independently selected from the group consisting of H, a linear C1-C18 hydrocarbyl group and a branched C1-C18 hydrocarbyl group wherein the C1-C18 hydrocarbyl group bears up to 3 O atoms and / or bears up to one double bond, as well as edible salts thereof, as flavor modulating compounds, and to flavor compositions and consumer products comprising said compounds, and to flavor compositions and consumer products comprising said compounds, where R1 and R2 are independently selected from the group consisting of H, a linear C1-C18 hydrocarbyl group and a branched C1-C18 hydrocarbyl group wherein said C1-C18 hydrocarbyl group bears up to 3 O atoms and / or up to one double bond, and / or bearing up to one ring, or wherein R1 and R2 together with the carbon atom to which they are attached form an aromatic six-membered hydrocarbon ring. # imgabs0 #

Description

Technical Field

[0001] The present invention generally relates to the use of compounds and edible salts thereof as flavor modulating compounds. The present invention also relates to flavor compositions and consumer products such as food or beverages comprising the compounds. The present invention also relates to methods of imparting, enhancing, improving, supplementing or altering the flavor properties of flavor compositions or consumer products by using the compounds.

[0002] background

[0003] Saltiness is one of the five basic taste attributes in addition to umami, sweetness, bitterness and sourness. Saltiness is associated with sodium chloride and is essential for stimulating the intake of healthy minerals through food. However, the modern diet is rich in highly processed foods, which often contain very high sodium chloride content. According to the World Health Organization (WHO), the recommended average daily intake is 5g / day. According to the FDA, the personal average daily intake (PADI) of sodium chloride for Americans is more than 8g sodium chloride per day, which is significantly higher than the recommended value. Continuously high PADI of sodium chloride can cause negative side effects such as high blood pressure, cardiovascular disease, renal failure and stroke. It is very desirable to reduce the PADI of sodium chloride, preferably without compromising the desired saltiness. Therefore, there is a need for compounds that enhance the perception of saltiness.

[0004] A range of candidate flavour compounds for salt enhancement have been described in the literature. For example, in US Pat. No. 9,155,329 B2, low molecular weight amides having additional hydroxyl or alkoxy groups are disclosed as having salt enhancing properties.

[0005] At least partial replacement of sodium chloride by other salts such as potassium chloride is often associated with negative taste aspects (Khetra et al, Int. Dairy J. (2019), 91, 165-171).

[0006] Another related aspect that is sometimes confused with salt perception is umami, although a completely different receptor mechanism is involved. The most prominent example of a compound that imparts umami is monosodium glutamate (MSG) (Ikeda, J. Tokyo Chem. Soc. (1909), 30, 820-836). Umami can be modified by the ribonucleotides inosine monophosphate (IMP) and guanosine monophosphate (GMP) (Kodama, J. Chem. Soc. of Japan. (1913), 34: 751-757; Kuninaka, J. Agric. Chem. Soc. Jpn. (1960), 34, 487-492). Other compounds that enhance the umami taste are, for example, theanine (Suzuku et al. J Agric Food Chem. (2002), 50 313-318) or specific oligopeptides (Yamasaki, et al, Agric. Biol. Chem. (1978), 42, 1761-1765; Tamura et al, Agric. Biol. Chem. (1989), 53, 319-325).

[0007] Glutathione is described as affecting both umami and salty tastes, more specifically, the duration of taste stimulation (Tazuko et al, Chem. Senses (2016), Volume 41, 623-630). A group of universal taste enhancers is reported in EP1291342.

[0008] A variety of other molecules are known to improve or influence salt perception. Volatile aroma compounds may also help to mimic an increased salty taste (Batenburg et al, J. Food Sci. (2011), 76, 280-288).

[0009] There remains a need for new taste improving substances that can adjust flavors to add to the flavorist's palette.

[0010] Overview

[0011] According to a first aspect of the present invention, there is provided a use of a compound of formula (I) or an edible salt thereof as a flavor regulating compound:

[0012]

[0013] Wherein R1 and R2 are independently selected from H, a straight-chain C1-C18 hydrocarbon group and a branched C1-C18 hydrocarbon group, wherein the C1-C18 hydrocarbon group has up to 3 O atoms, and / or has up to one double bond, and / or has up to one ring, or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring.

[0014] According to a second aspect of the present invention, there is provided a flavor composition comprising a compound of formula (I) or an edible salt thereof:

[0015]

[0016] Wherein R1 and R2 are independently selected from H, a straight-chain C1-C18 hydrocarbon group and a branched C1-C18 hydrocarbon group, wherein the C1-C18 hydrocarbon group has up to 3 O atoms, and / or has up to one double bond, and / or has up to one ring, or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring.

[0017] According to a third aspect of the present invention, there is provided a consumable product comprising a compound of formula (I) or an edible salt thereof, or a flavor composition comprising a compound of formula (I) or an edible salt thereof:

[0018]

[0019] Wherein R1 and R2 are independently selected from H, a straight-chain C1-C18 hydrocarbon group and a branched C1-C18 hydrocarbon group, wherein the C1-C18 hydrocarbon group has up to 3 O atoms, and / or has up to one double bond, and / or has up to one ring, or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring.

[0020] According to a fourth aspect of the present invention, there is provided a method for imparting, enhancing, improving or altering the flavor properties of a flavor composition or a consumer product, the method comprising adding a compound of formula (I) or an edible salt thereof to the flavor composition or the consumer product in an amount sufficient to impart, enhance, improve or alter the flavor properties of the flavor composition or the consumer product:

[0021]

[0022] Wherein R1 and R2 are independently selected from H, a straight-chain C1-C18 hydrocarbon group and a branched C1-C18 hydrocarbon group, wherein the C1-C18 hydrocarbon group has up to 3 O atoms, and / or has up to one double bond, and / or has up to one ring, or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring.

[0023] Certain embodiments of any aspect of the invention may provide one or more of the following advantages:

[0024] ● Regulation of salt taste perception, especially positive regulation,

[0025] ● Reduce bitterness, such as the bitterness of KCl,

[0026] ● Enhanced umami perception,

[0027] ● Acidity adjustment, and

[0028] - Enhanced flavour perception of food or beverages, particularly savoury food or beverages.

[0029] The details, embodiments and preferred embodiments provided about any specific one or more described aspects of the present invention will be further described in this article, and are equally applicable to all aspects of the present invention. Unless otherwise specified herein or obviously contradictory with context, the present invention encompasses any combination of all possible variations of the embodiments, embodiments and preferred embodiments described herein.

[0030] Detailed Description

[0031] The present invention is based on the surprising discovery that 1H-imidazole and certain derivatives thereof have flavor-modifying properties.

[0032] Therefore, there is provided the use of one or more compounds of formula (I) and edible salts thereof as flavor-adjusting compounds:

[0033]

[0034] Wherein R1 and R2 are independently selected from H, a straight-chain C1-C18 hydrocarbon group and a branched C1-C18 hydrocarbon group, wherein the C1-C18 hydrocarbon group has up to 3 O atoms, and / or has up to one double bond, and / or has up to one ring, or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring.

[0035] For example, the C1-C18 hydrocarbon group may be a linear or branched C1-C18 alkyl group, a linear or branched C2-C18 alkenyl group, or a formyl group.

[0036] For example, the C1-C18 alkyl group may be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, hexadecyl, or octadecyl.

[0037] For example, the C2-C18 alkenyl group may be ethenyl, propenyl, or octadecenyl.

[0038] For example, the C1-C18 hydrocarbon radical may carry up to 3 O atoms, which means 1, 2 or 3 O atoms. For example, the hydrocarbon radical carries hydroxyl, ether, carbonyl, carboxyl and / or ether groups.

[0039] For example, the C1-C18 alkyl group may have at most one ring, such as cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl. Optionally, the ring may contain O atoms and / or be substituted by a functional group with O atoms. For example, the C1-C18 alkyl group with at most 3 O atoms and at most one double bond may be 2-oxoethyl, 3-oxopropyl, carboxyl, carboxymethyl, carboxyl(hydroxy)methyl, carboxylcarbonyl, 2-carboxyethyl, 2-carboxyvinyl, 3-carboxypropyl. The substituted alkyl or alkenyl residues are formally derived from acetaldehyde, propionaldehyde, formic acid, acetic acid, lactic acid, pyruvic acid, propionic acid, acrylic acid, butyric acid, respectively.

[0040] The compound of formula (I) in which R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring is benzimidazole (1H-1,3-benzimidazole, CAS-No. 51-17-2).

[0041] According to certain illustrative embodiments, the formyl residue is formally derived from formaldehyde.

[0042] Edible salts as used herein include those commonly used in the food and beverage industry and include chlorides, sulfates, phosphates, gluconates, sodium, citrates, carbonates, acetates, lactates, and combinations thereof.

[0043] If the compound of formula (I) contains a stereocenter or a double bond, the compound is a single isomer, such as an enantiomer or a diastereomer or a double bond isomer, or a mixture of more than one isomer. In particular, the double bond in the compound of formula (I) can have an E- or Z-configuration, or the compound exists as a mixture. The stereocenter of the compound of formula (I) can have an R- or S-configuration, or the compound exists as a mixture.

[0044] 1H-imidazole exists in two identical tautomeric forms, and both tautomeric forms are included in the present invention. For example, 4-methyl-1H-imidazole is a tautomer of 5-methyl-1H-imidazole.

[0045] Furthermore, the compounds of the present invention may be a mixture of more than one compound in the form of any one of its isomers or a mixture thereof.

[0046] The compounds of the present invention described above have flavor-modulating properties. For example, some compounds can enhance salty taste perception, and / or reduce bitterness, and / or modulate acidity and freshness, and / or enhance umami taste.

[0047] Throughout this document, the terms "taste" and "flavor" are used interchangeably to describe the sensory effects perceived through the olfactory epithelium in the oral cavity (particularly the tongue) and nasal cavity.

[0048] As used herein, the term "flavor-adjusting compound" refers to a compound that has weak or barely noticeable flavor properties in itself at the concentration used. However, the compound is able to modify or supplement or adjust or contribute to the taste impact of other flavoring substances contained in the flavor composition or consumable, including salty impact, sour impact, bitterness and / or umami impact.

[0049] For example, the flavor-adjusting compound does not have any salty taste at all below 40ppm. The compound may have a slightly salty taste at a level of 50ppm to 100ppm. At higher levels, such as at about 1000ppm, the compound may still have only a weak salty taste. In combination with a salty flavor compound (e.g., with NaCl), it can enhance salty taste perception.

[0050] For example, the flavor-adjusting compound does not have any identifiable taste at levels below 40 ppm to counteract or mask the bitter taste. At higher levels, such as at about 1000 ppm, the compound may even have a strong bitter taste. When combined with a compound that may have a bitter taste (such as KCl), the compound may reduce the bitter taste, such as when used at a level of 50 ppm to 100 ppm.

[0051] For example, the flavor modulating compound does not impart any umami taste at levels below 40 ppm. In combination with compounds that can impart umami taste, such as MSG, for example, when used at levels of 50 ppm to 100 ppm, the umami taste is enhanced.

[0052] For example, the flavor-modulating compounds may affect acidity and freshness.

[0053] As used herein, the term "flavoring substance" refers to any substance that can impart a detectable flavor impact, preferably at a concentration of less than 0.1 wt%, more preferably less than 0.01 wt%. For example, such a flavoring substance can be selected from natural flavorings, artificial flavorings, spices, seasonings, etc., synthetic flavoring oils and flavoring aromatics and / or oils, oleoresins, essences, distillates, and extracts derived 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, Publication 1274, pp. 63-258, by the National Academy of Sciences. This publication is incorporated herein by reference.

[0054] The flavor-adjusting compounds of the present invention have been found to be very useful ingredients that are able to impart highly appreciated taste sensations, particularly "roundness", "fullness", "substance", "transparency", "complexity", "extension", "continuity", "persistence", "tingling", "numbing", "bitterness" and / or "metallic taste" to the products into which they are incorporated in the presence of other flavoring substances. Thus, the taste-improving substances of the present invention can be used to improve the taste (including "mouthfeel") of foods and beverages.

[0055] In one embodiment of the present invention, there is provided a use of a compound of formula (I) and an edible salt thereof as a flavor-adjusting compound,

[0056] Wherein one of R1 and R2 is H,

[0057] and the other of R1 and R2 is selected from a linear or branched C1-C18 hydrocarbon group having at most 3 O atoms, and / or having at most one double bond, and / or having at most one ring,

[0058] Or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring.

[0059] In one embodiment of the present invention, there is provided a use of a compound of formula (I) and an edible salt thereof as a flavor-adjusting compound,

[0060] Wherein one of R1 and R2 is H,

[0061] and the other of R1 and R2 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, hexadecyl, octadecyl, vinyl, propenyl, octadecenyl, formyl, 2-oxoethyl, 3-oxopropyl, carboxyl, carboxymethyl, carboxy(hydroxy)methyl, carboxycarbonyl, 2-carboxyethyl, 2-carboxyvinyl and 3-carboxypropyl,

[0062] Or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring.

[0063] In one embodiment of the present invention, there is provided the use of the compound of formula (I) as defined above and its edible salt as a flavor regulating compound, wherein the compound of formula (I) is selected from 1H-imidazole, 4-methyl-1H-imidazole, 4-ethyl-1H-imidazole, 4-propyl-1H-imidazole, 4-butyl-1H-imidazole, 4-hexadecyl-1H-imidazole, 4-octadecyl-1H-imidazole, 4-vinyl-1H-imidazole, 4-propenyl-1H-imidazole, 4-octadecyl-1H-imidazole, , 1H-imidazole-4-carboxaldehyde, 2-(1H-imidazole-4-yl)acetaldehyde, 3-(1H-imidazole-4-yl)propionaldehyde, 1H-imidazole-4-carboxylic acid, 2-(1H-imidazole-4-yl)acetic acid, 2-hydroxy-2-(1H-imidazole-4-yl)acetic acid, 2-(1H-imidazole-4-yl)-2-oxoacetic acid, 3-(1H-imidazole-4-yl)propionic acid, 3-(1H-imidazole-4-yl)acrylic acid (urocanic acid), 4-(1H-imidazole-4-yl)butyric acid and benzimidazole.

[0064] In particular, the use of a compound of formula (I) is provided, wherein the compound of formula (I) is selected from 1H-imidazole, 4-methyl-1H-imidazole, 3-(1H-imidazol-4-yl)acrylic acid (urocanic acid), 2-(1H-imidazol-4-yl)acetic acid and benzimidazole.

[0065] 1H-imidazole is a well-known compound and an important structural element in pharmaceutical and agrochemical compounds. So far, no taste or taste-modifying properties have been reported in the literature. 4-Methyl-1H-imidazole is present in caramel color, which is widely used in food and beverages. However, no information on the taste or taste-modifying properties of said compound is available. 3-(1H-imidazole-4-yl) acrylic acid (urocanic acid) is a known compound in the field of skin care. Benzimidazole is a known raw material for the synthesis of many drugs.

[0066] In another embodiment of the present invention there is provided the use of a mixture of two or more compounds of formula (I) as defined above as flavour modulating compounds.

[0067] In another embodiment, the flavor modulating compounds according to the present invention are particularly suitable for use in various flavor compositions and consumables, including savory foods, non-savory foods, such as dairy products, beverages, and confectionery.

[0068] For example, the flavor composition comprises, based on the total weight of the composition, 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 composition, 0.001 to 80 wt% of the flavor-adjusting compound according to the present invention, preferably 0.01 to 50 wt%, more preferably 0.01 to 20 wt% of the flavor-adjusting compound.

[0069] In a typical flavor composition, the flavor modulating compound and flavoring substance are used in a weight ratio of 10:1 to 1:150, preferably a weight ratio of 5:1 to 1:100.

[0070] The flavor composition comprising the flavor-adjusting compound may be suitably prepared in the form of a liquid, a paste or a powder. For example, the flavor composition is a free-flowing powder.

[0071] Typical examples of the flavor composition include savory flavors, sour / acid flavors, and others.

[0072] For example, the flavor composition is a reduced salt flavor composition.

[0073] The flavor adjustment compounds of the present invention can be used in flavor compositions together with one or more ingredients or excipients commonly used in flavor compositions other than flavoring substances (e.g., carrier materials and other adjuvants commonly used in the art). Suitable excipients for flavor compositions are well known in the art and include, for example, but not limited to, solvents (including water, alcohol, ethanol, oil, fat, vegetable oil and miglyol), binders, diluents, disintegrants, lubricants, flavoring agents, colorants, preservatives, antioxidants, emulsifiers, stabilizers, flavor enhancers, anti-caking agents, etc.

[0074] Examples of such carriers or diluents for flavor compositions 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.), 1sted., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0075] Other suitable and desirable ingredients for flavor compositions are described in standard textbooks, for example "Handbook of Industrial Chemical Additives", ed. M. and I. Ash, 2nd Ed., (Synapse 2000).

[0076] In another aspect of the present invention, there is also provided a consumable product comprising at least one compound of formula (I) or a flavour composition comprising one or more compounds of formula (I) and a product base.

[0077] "Product base" refers to the combination of all conventional, art-recognized ingredients required for a particular consumer product composition.

[0078] In another aspect of the invention there is provided a consumable selected from food and beverages comprising at least 10 ppm, preferably at least 50 ppm, more preferably at least 100 ppm or 200 ppm of one or more flavour modulating compounds of formula (I) and / or edible salts thereof.

[0079] For example, the product contains at least 0.001 wt%, more preferably at least 0.005 wt%, even more preferably at least 0.01 wt%, most preferably at least 0.02 wt% of one or more flavor adjusting compounds. Typically, the above product will contain a concentration of no more than 0.05 wt%, preferably no more than 0.025 wt% of flavor adjusting compounds.

[0080] For example, the consumable has a reduced salt content.

[0081] Typical examples of food products according to the invention include soups, sauces, stocks, bouillons, cheese products, condiments, dressings, margarines, noodles and beverages.

[0082] The flavor-modulating compounds according to the invention can be advantageously applied to impart desired taste attributes to the above-mentioned products. Furthermore, the flavor-modulating compounds according to the invention are able to modulate the taste impact of other flavor components contained in these same products, thereby improving the overall flavor quality of these products.

[0083] In another aspect of the present invention there is provided the use of a compound of formula (I) as a flavour modulating compound, wherein the compound may be used in pure or diluted form, provided in liquid or solid form.

[0084] In another aspect of the present invention, there is provided a method for imparting, enhancing, improving or altering the flavor characteristics of a flavor composition or a consumer product, the method comprising adding at least one flavor-adjusting compound to the composition or consumer product, which is a compound of formula (I) or an edible salt thereof. For example, the flavor-adjusting compound is added in an amount of at least 0.001 wt %, preferably at least 0.01 wt %.

[0085] The preparation of the compounds of the present invention can be carried out by methods known in the art. For example, the compounds can be obtained by chemical or enzymatic reactions.

[0086] The present invention will now be further described with reference to the following non-limiting examples. These examples are for illustrative purposes only, and it is to be understood that variations and modifications may be made by those skilled in the art. Example

[0087] Overview:

[0088] 1H-imidazole (CAS-No. 288-32-4), 4-methyl-1H-imidazole (CAS-No. 822-36-6), (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid (3-(1H-imidazol-4-yl)acrylic acid or urocanic acid, CAS-No. 104-98-3), 2-(1H-imidazol-4-yl)acetic acid (CAS-No. 645-65-8) and benzimidazole (CAS-No. 51-17-2) are commercially available, for example, from Sigma-Aldrich.

[0089] In the following examples, concentrations are given in % by weight.

[0090] Example 1: Taste

[0091] A sensory panel has tasted different concentrations of 1H-imidazole in water.

[0092] While no effect was observed up to a concentration level of 40 ppm, a subtle salty taste could be detected at a concentration of 50 ppm. At a concentration level of 100 ppm, the compound had a weak salty taste along with some astringency and acidity. The salinity of 1H-imidazole at a concentration level of 100 ppm was comparable to a 0.05% NaCl aqueous solution, however, the salinity was flat and did not match all aspects of NaCl. At a concentration level of 1000 ppm, a weak salty taste was still felt, but it was mainly bitter.

[0093] Example 2: Salt Enhancement

[0094] Two aqueous solutions were prepared:

[0095] A) 0.3% NaCl, and

[0096] B) 0.3% NaCl and 100 ppm 1H-imidazole.

[0097] The solutions were tasted by a sensory panel. Solution A was described as "salty". Solution B was described as noticeably saltier, as well as having a mineral aroma, low acidity, some astringency and freshness.

[0098] Example 3: Umami Enhancement

[0099] Two aqueous solutions were prepared:

[0100] A) 0.5% NaCl, 0.03% MSG, 0.007% ribonucleotides, and

[0101] B) 0.5% NaCl, 0.03% MSG, 0.007% ribonucleotides and 100 ppm 1H-imidazole.

[0102] The solutions were tasted by a sensory panel. Solution A was a model solution for salty umami taste, containing MSG (monosodium glutamate) and nucleotides (IMP / GMP, 50 / 50 mixture) as salty umami enhancers. Solution B was described as having a strong salty taste and umami enhancement compared to solution A.

[0103] Example 4: Bitterness Masking

[0104] Two aqueous solutions were prepared:

[0105] A) 0.3% KCl, and

[0106] B) 0.3% KCl and 70 ppm 1H-imidazole.

[0107] The solutions were tasted by a sensory panel. Compared to solution A, solution B was described as less metallic and more salty.

[0108] Example 5: Effect on broth

[0109] A model broth base containing 0.3% NaCl was compared to a sample further containing 100 ppm of 1H-imidazole.

[0110] The solutions were tasted by a sensory panel. Compared to the model broth base, the samples additionally containing 1H-imidazole were described as more mineral and saltier as well as more umami.

[0111] Example 6: Effect on cheese sauce

[0112] The effect of 1H-imidazole on a commercial cheese sauce has been investigated. Therefore, a sensory panel has compared the cheese sauce with a sauce sample which further contained 70 ppm of 1H-imidazole.

[0113] The sauces containing 1H-imidazole in addition were described as more mineral and saltier.

[0114] Example 7: Combinations with other taste modulating compounds

[0115] The combination of taste modulating compounds is added to a 0.3% NaCl aqueous solution.

[0116] A) 100 ppm of 1H-imidazole and 50 ppm of N-lactylethanolamine;

[0117] B) 100 ppm of 1H-imidazole and 0.04 ppm of N-oleoylmethionine;

[0118] C) 100 ppm of 1H-imidazole and 50 ppm of ((2E)-3-(1H-imidazol-4-yl)-N-[2-(1H-imidazol-4-yl)ethyl]prop-2-enamide); and

[0119] D) 100 ppm of 1H-imidazole, 50 ppm of N-lactylethanolamine, 0.04 ppm of N-oleoylmethionine and 50 ppm of ((2E)-3-(1H-imidazol-4-yl)-N-[2-(1H-imidazol-4-yl)ethyl]prop-2-enamide).

[0120] The samples were tasted by a sensory panel and rated against a 100 ppm solution of 1H-imidazole in 0.3% NaCl solution.

[0121] Sample A was described as exhibiting more salty and mineral notes.

[0122] Sample B was considered even saltier.

[0123] Sample C had an enhanced salty taste.

[0124] Sample D performed best in terms of saltiness.

[0125] Example 8: Effect on potato chips

[0126] The sensory panel tasted potato chips with 1.5% salt with and without 1H-imidazole.

[0127] The potato chips containing 70 ppm of 1H-imidazole had a higher salinity impact and lingering effect compared to potato chips without 1H-imidazole.

[0128] Example 9: Effect on mayonnaise

[0129] Commercial samples with and without added 1H-imidazole were compared by a sensory panel.

[0130] Compared to neat mayonnaise, the sample containing 70 ppm of 1H-imidazole was described as noticeably saltier and having a stronger acetic acid character.

[0131] Example 10: Effect on corn rolls

[0132] The sensory panel compared tacos with cheese flavor with and without the addition of 1H-imidazole.

[0133] The taste of the tacos with 100 ppm of 1H-imidazole added was described as saltier and the richness characteristics were enhanced compared to the tacos without 1H-imidazole.

[0134] Example 11: Effect on Vegetarian Burgers

[0135] A sensory panel tasted a soy-based vegetarian burger with and without 1H-imidazole.

[0136] The burger with 70 ppm of 1H-imidazole was described as saltier compared to the burger without 70 ppm of 1H-imidazole, and this applied to the initial peak of saltiness as well as the final stages of salt perception.

[0137] Example 12: Salt Enhancement

[0138] Two aqueous solutions were prepared:

[0139] A) 0.5% NaCl, and

[0140] B) 0.5% NaCl and 50 ppm of 4-methyl-1H-imidazole.

[0141] The solutions were tasted by a sensory panel. Solution A was described as "salty". Solution B was described as saltier than Solution A.

[0142] Example 13: Salt Enhancement

[0143] Two aqueous solutions were prepared:

[0144] A) 0.5% NaCl, and

[0145] B) 0.5% NaCl and 50 ppm of (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid (urocanic acid).

[0146] The solutions were tasted by a sensory panel. Solution A was described as "salty". Solution B was described as saltier than Solution A.

[0147] Example 14: Taste

[0148] The sensory panel has tasted different concentrations of 2-(1H-imidazol-4-yl)acetic acid and benzimidazole in water.

[0149] Benzimidazole can be detected with subtle salty and sour tastes at a concentration of 30 ppm. At a concentration level of 70 ppm, the compound has a weak salty taste with some sour background.

[0150] For 2-(1H-imidazol-4-yl)acetic acid, a subtle salty and mineral taste can be detected at a concentration of 30 ppm. At a concentration level of 90 ppm, the compound has a weak salty, mineral taste with a slight sour taste.

[0151] The saltiness of both compounds at a concentration level of 70 ppm is comparable to 0.05% NaCl in water.

[0152] Example 15: Salt Enhancement

[0153] Prepare the following aqueous solutions:

[0154] A) 0.3% NaCl,

[0155] B) 0.3% NaCl and 90 ppm of 2-(1H-imidazol-4-yl)acetic acid, and

[0156] C) 0.3% NaCl and 80 ppm benzimidazole.

[0157] The solutions were tasted by a sensory panel. Solution A was described as "salty". Solution B was described as noticeably saltier, with a mineral note, and Solution C was described as noticeably saltier, with a sour, fresh background.

[0158] Example 16: Bitterness Masking

[0159] Prepare the following aqueous solutions:

[0160] A) 0.3% KCl, and

[0161] B) 0.3% KCl and 100 ppm of 2-(1H-imidazol-4-yl)acetic acid, and

[0162] C) 0.3% KCl and 100 ppm of benzimidazole.

[0163] The solutions were tasted by a sensory panel. Solutions B and C were described as less bitter, less metallic and saltier than solution A. Both compounds were good masking agents for KCl. Solution B was superior to solution C.

[0164] Example 17: Effect on Broth

[0165] A model broth base containing 0.3% NaCl was compared with samples further containing 70 ppm of 2-(1H-imidazol-4-yl)acetic acid and 100 ppm of benzimidazole, respectively.

[0166] The solutions were tasted by a sensory panel. Compared to the model broth base, samples additionally comprising 2-(1H-imidazol-4-yl)acetic acid or benzimidazole were described as more mineral and saltier. Solutions comprising benzimidazole were preferred.

[0167] Example 18: Effect on Cheese Sauce

[0168] The effect of 2-(1H-imidazol-4-yl)acetic acid on a commercial cheese sauce has been investigated. Therefore, a sensory panel has compared the cheese sauce with a cheese sauce sample further comprising 50 ppm of 2-(1H-imidazol-4-yl)acetic acid.

[0169] Cheese sauces that additionally comprise 2-(1H-imidazol-4-yl)acetic acid are preferred, as they have a greater salty and umami character.

[0170] Example 19: Combinations with other taste modulating compounds

[0171] The combination of taste modulating compounds is added to a 0.3% NaCl aqueous solution.

[0172] A) 50 ppm of 2-(1H-imidazol-4-yl)acetic acid and 50 ppm of N-lactylethanolamine;

[0173] B) 50 ppm of 2-(1H-imidazol-4-yl)acetic acid and 0.04 ppm of N-oleoylmethionine;

[0174] C) 50 ppm of 2-(1H-imidazol-4-yl)acetic acid, 50 ppm of N-lactylethanolamine and 0.04 ppm of N-oleoylmethionine,

[0175] D) 50 ppm of 2-(1H-imidazol-4-yl)acetic acid, 50 ppm of N-lactylethanolamine, 0.04 ppm of N-oleoylmethionine and 50 ppm of ((2E)-3-(1H-imidazol-4-yl)-N-[2-(1H-imidazol-4-yl)ethyl]prop-2-enamide),

[0176] E) 50 ppm of benzimidazole and 50 ppm of N-lactylethanolamine;

[0177] F) 50 ppm of benzimidazole and 0.04 ppm of N-oleoylmethionine;

[0178] G) 50 ppm of benzimidazole, 50 ppm of N-lactylethanolamine and 0.04 ppm of N-oleoylmethionine,

[0179] H) 50 ppm of benzimidazole, 50 ppm of N-lactylethanolamine, 0.04 ppm of N-oleoylmethionine and 50 ppm of ((2E)-3-(1H-imidazol-4-yl)-N-[2-(1H-imidazol-4-yl)ethyl]prop-2-enamide),

[0180] The samples were tasted by a sensory panel and rated against a 50 ppm solution of the corresponding imidazole derivative in 0.3% NaCl solution.

[0181] Sample A was described as having an enhanced salty effect and a persistent mineralizing character.

[0182] Sample B was also perceived to be saltier than the blend of 2-(1H-imidazol-4-yl)acetic acid and salt.

[0183] Sample C has good salt enhancement with an overall balanced effect.

[0184] Sample D performed best in terms of balance and saltiness.

[0185] Sample E was described as having an enhanced salty taste effect and a persistent mineralizing character. This effect was superior to that of Sample A.

[0186] Sample F is considered similar to a blend of benzimidazole and salt.

[0187] Sample G has good salt enhancement with an overall balanced effect.

[0188] Sample H is considered similar to Sample G.

[0189] Example 20: Effect on mayonnaise

[0190] Commercial mayonnaise samples with and without the addition of 2-(1H-imidazol-4-yl)acetic acid or benzimidazole were compared by a sensory panel.

[0191] Compared to pure mayonnaise, samples containing 70 ppm of 2-(1H-imidazol-4-yl)acetic acid or benzimidazole were described as being significantly saltier, with a less sour impression.

[0192] Example 21: Effect on tacos

[0193] A sensory panel compared tacos with cheese flavor with and without the addition of 2-(1H-imidazol-4-yl)acetic acid or benzimidazole.

[0194] The taste of tacos with the addition of 150 ppm of 2-(1H-imidazol-4-yl)acetic acid or benzimidazole was described as saltier and the richness of the notes was enhanced compared to tacos without the additional compounds.

[0195] Example 22: Effect on tomato paste

[0196] Commercial tomato paste samples with and without the addition of 2-(1H-imidazol-4-yl)acetic acid or benzimidazole were compared by a sensory panel.

[0197] Compared to pure ketchup, the sample containing 100 ppm of 2-(1H-imidazol-4-yl)acetic acid was described as significantly saltier, more persistently sour and less sweet. The sample containing 70 ppm of benzimidazole was also described as significantly saltier.

Claims

1. Use of one or more compounds of formula (I) and their edible salts as flavor regulating compounds: in R1 and R2 are independently selected from H, straight-chain C1-C18 hydrocarbon groups and branched C1-C18 hydrocarbon groups, wherein the C1-C18 hydrocarbon groups have up to 3 O atoms, and / or have up to one double bond, and / or have up to one ring, Or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring.

2. The method of claim 1 , wherein R1 and R2 are independently selected from H, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, hexadecyl, octadecyl, vinyl, propenyl, octadecenyl, formyl, 2-oxoethyl, 3-oxopropyl, carboxyl, carboxymethyl, carboxy(hydroxy)methyl, carboxycarbonyl, 2-carboxyethyl, 2-carboxyvinyl and 3-carboxypropyl, or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered ring.

3. The use according to claim 1 or 2, wherein the compound is selected from 1H-imidazole, 4-methyl-1H-imidazole, 4-ethyl-1H-imidazole, 4-propyl-1H-imidazole, 4-butyl-1H-imidazole, 4-hexadecyl-1H-imidazole, 4-octadecyl-1H-imidazole, 4-vinyl-1H-imidazole, 4-propenyl-1H-imidazole, 4-octadecenyl-1H-imidazole, 1H-imidazole-4-carboxaldehyde, 2- (1H-imidazol-4-yl)acetaldehyde, 3-(1H-imidazol-4-yl)propanal, 1H-imidazole-4-carboxylic acid, 2-(1H-imidazol-4-yl)acetic acid, 2-hydroxy-2-(1H-imidazol-4-yl)acetic acid, 2-(1H-imidazol-4-yl)-2-oxoacetic acid, 3-(1H-imidazol-4-yl)propionic acid, 3-(1H-imidazol-4-yl)acrylic acid, 4-(1H-imidazol-4-yl)butyric acid and benzimidazole.

4. Use according to any one of the preceding claims, wherein the compound is used as a salt enhancing compound.

5. Use according to any one of the preceding claims, wherein the compound is used as a compound influencing sour taste and / or a compound masking bitter taste and / or a compound enhancing umami taste.

6. A flavour composition comprising a compound as defined in claims 1 to 3.

7. The flavor composition of claim 6, comprising about 0.001 to 80 wt% of the compound based on the flavor composition.

8. A consumable product comprising a compound as defined in claims 1 to 3 or a flavour composition according to claim 6 or 7 and a consumable product base.

9. The consumable product of claim 8, comprising about 0.001 to 0.05 wt% of the compound.

10. The consumable product according to claim 8, wherein the consumable product is selected from the group consisting of food and beverages.

11. A method of imparting, enhancing, improving or altering the flavor properties of a flavor composition or a consumable product, said method comprising adding to said composition or consumable product at least one compound as defined in claims 1 to 3.

12. The method of claim 11, wherein the flavor attribute is salty.

13. The method of claim 12, wherein the flavor characteristics are sour, bitter and / or umami.

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