Organic compound

Abstract

The present disclosure relates to compounds of formula (I) and their use as flavor modifying compounds in edible salts, wherein R1 and R2 are independently selected from the group consisting of H, a linear 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 1 double bond and / or has up to 1 ring, or wherein R1 and R2 together with the carbon atom to which they are attached form an aromatic 6-membered hydrocarbon ring, and to flavor compositions and consumer products containing said compounds.

Description

[Technical field]

[0001] Technical Field The present invention generally relates to compounds and their use as compounds for regulating the flavor of edible salt.The present invention further relates to flavor compositions and consumer products, such as foodstuffs or beverages, that contain the compounds.The present invention also relates to a method for imparting, enhancing, improving, complementing, or modifying the flavor characteristics of a flavor composition or consumer product by using the compounds. [Background technology]

[0002] background Saltiness is one of the five fundamental taste attributes, next to umami, sweetness, bitterness, and sourness. Saltiness is associated with sodium chloride and is essential for stimulating healthy mineral uptake from food. However, modern diets are rich in highly processed foods that often contain extremely high amounts of sodium chloride. According to the World Health Organization (WHO), an average daily intake of 5 g / day is recommended. According to the FDA, the personal average daily intake (PADI) of sodium chloride in Americans exceeds 8 g sodium chloride per day, clearly exceeding the recommended value. A persistently high PADI of sodium chloride can cause negative side effects such as hypertension, cardiovascular disease, renal failure, and stroke. It is highly desirable to reduce the PADI of sodium chloride, preferably without compromising the desired saltiness. Thus, there is a need for compounds that enhance the perception of saltiness.

[0003] Various flavor compounds as potential salt-enhancing agents have been described in the literature, for example US 9,155,329 B2 discloses that low molecular weight amides with added hydroxyl or alkoxyl groups have salt-enhancing properties.

[0004] At least partial replacement of sodium chloride with other salts, such as potassium chloride, is often associated with negative taste profiles (Khetra et al, Int. Dairy J. (2019), 91, 165-171).

[0005] Another related aspect, sometimes confused with salt perception, is umami taste, but involves a completely different receptor mechanism. The most prominent example of a compound that confers umami taste 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. Soc. of Japan. (1913), 34: 751-757; Kuninaka, J. Chem. Soc. Jpn. (1960), 34, 487-492). Other compounds that enhance umami taste are, for example, theanine (Suzuku et al. J Agric Food Chem. (2002), 50 313-318) or special oligopeptides (Yamasaki, et al, Agric. Biol. Chem. (1978), 42, 1761-1765; Tamura et al, Agric. Biol. Chem. (1989), 53, 319-325).

[0006] Glutathione has been described to affect umami and saltiness simultaneously, more precisely the duration of taste stimulation (Tazuko et al, Chem. Senses (2016), Volume 41, 623-630). A group of general taste enhancers was reported in EP1291342.

[0007] A variety of other molecules are known to improve or affect salt perception, and volatile aroma compounds can help mimic increased saltiness (Batenburg et al, J. (2011), 76, 280-288).

[0008] There remains a need to add new flavor-tunable taste improving substances to the flavorist's palette. Summary of the Invention

[0009] overview According to a first aspect of the present invention there is provided one or more compounds of formula (I) or their use as flavour modifying compounds in edible salt: [ka] wherein R1 and R2 are independently selected from the group consisting of H, a linear 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 1 double bond and / or has up to 1 ring, or wherein R1 and R2 together with the carbon atom to which they are attached form an aromatic 6-membered hydrocarbon ring.

[0010] According to a second aspect of the present invention there is provided a flavour composition comprising one or more compounds of formula (I) or an edible salt thereof: [ka] wherein R1 and R2 are independently selected from the group consisting of H, a linear 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 1 double bond and / or has up to 1 ring, or wherein R1 and R2 together with the carbon atom to which they are attached form an aromatic 6-membered hydrocarbon ring.

[0011] According to a third aspect of the present invention there is provided a consumer product comprising one or more compounds of formula (I) or an edible salt thereof, or a flavour composition comprising a compound of formula (I) or an edible salt thereof: [ka] wherein R1 and R2 are independently selected from the group consisting of H, a linear 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 1 double bond and / or has up to 1 ring, or wherein R1 and R2 together with the carbon atom to which they are attached form an aromatic 6-membered hydrocarbon ring.

[0012] According to a fourth aspect of the present invention there is provided a method of imparting, enhancing, improving or modifying the flavour characteristics of a flavour composition or consumer product, the method comprising adding to the flavour composition or to the consumer product one or more compounds of formula (I) or edible salts thereof in an amount sufficient to impart, enhance, improve or modify the flavour characteristics of the flavour composition or consumer product: [ka] wherein R1 and R2 are independently selected from the group consisting of H, a linear 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 1 double bond and / or has up to 1 ring, or wherein R1 and R2 together with the carbon atom to which they are attached form an aromatic 6-membered hydrocarbon ring.

[0013] Certain embodiments of any aspect of the invention may provide one or more of the following advantages: Regulation of salty taste perception, especially positive regulation, ● Reduction of bitterness, e.g. KCl, Enhancement of umami taste perception, ●Adjusting acidity, and - Enhanced aroma perception of foodstuffs or beverages, especially savory foodstuffs or beverages.

[0014] Details, examples, and preferences provided in connection with one or more particular described aspects of the invention will be explained further herein and will apply equally to all aspects of the invention. Any combination of the embodiments, examples, and preferences described herein in all possible variations thereof is also covered by the present invention, unless otherwise indicated herein or clearly contradicted by context.

[0015] Detailed Description The present invention is based on the surprising discovery that 1H-imidazole and certain of its derivatives have flavour modulating properties.

[0016] Thus, there is provided one or more compounds of formula (I) or their use as flavour modulating compounds in edible salts: [ka] wherein R1 and R2 are independently selected from the group consisting of H, a linear 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 1 double bond and / or has up to 1 ring, or wherein R1 and R2 together with the carbon atom to which they are attached form an aromatic 6-membered hydrocarbon ring.

[0017] For example, the C1-C18 hydrocarbon group can be a linear or branched C1-C18 alkyl, a linear or branched C2-C18 alkenyl, or formyl.

[0018] For example, the C1-C18 alkyl can be Me, Et, n-Pr, iso-Pr, n-Bu, iso-Bu, sec-Bu, tert-Bu, hexadecyl, or octadecyl.

[0019] For example, the C2-C18 alkenyl can be ethenyl, propenyl, octadecenyl.

[0020] For example, the C1-C18 hydrocarbon group can have up to 3 O atoms, which means 1, 2, or 3 O atoms. For example, the hydrocarbon group has a hydroxyl group, an ether group, a carbonyl group, a carboxyl group, and / or an ether group.

[0021] For example, the C1-C18 hydrocarbon group can have up to one ring, such as cyclopentyl, cyclohexyl, cyclopentenyl or cyclohexenyl. Optionally, the ring can contain O atoms and / or be substituted with a functional group having an O atom. For example, the C1-C18 hydrocarbon group with up to three O atoms and up to one double bond can be 2-oxoethyl, 3-oxopropyl, carboxyl, carboxymethyl, carboxy(hydroxy)methyl, carboxycarbonyl, 2-carboxyethyl, 2-carboxyvinyl, 3-carboxypropyl. The substituted alkyl or alkenyl residue is formally derived from acetaldehyde, propanal, formic acid, acetic acid, lactic acid, pyruvic acid, propanoic acid, propenoic acid, butanoic acid, respectively.

[0022] 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 number 51-17-2).

[0023] According to certain exemplary embodiments, the formyl residue is formally derived from formaldehyde.

[0024] As used herein, edible salts include those typically employed in the food and beverage industry and include chloride, sulfate, phosphate, gluconate, sodium, citrate, carbonate, acetate, lactate, and combinations thereof.

[0025] When the compound of formula (I) contains a stereocenter or a double bond, the compound is a single isomer, such as an enantiomer or diastereomer or a double bond isomer, or a mixture of more than one isomer. In particular, the double bond of 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 either an R or S configuration, or the compound exists as a mixture.

[0026] 1H-imidazole exists in two equivalent tautomeric forms, and both tautomeric forms are covered by the present invention. For example, 4-methyl-1H-imidazole is a tautomer of 5-methyl-1H-imidazole.

[0027] Furthermore, the compounds of the present invention may be a mixture of more than one chemical compound in the form of any of its isomers, or mixtures thereof.

[0028] The compounds of the invention described above have flavor modulating properties, for example some of the compounds can enhance the perception of saltiness, and / or reduce bitterness, and / or modulate sourness and freshness, and / or enhance umami.

[0029] Throughout this document, the terms "taste" and "flavor" are used interchangeably to describe the sensory impact perceived through the mouth, particularly the tongue, and the olfactory epithelium in the nasal cavity.

[0030] As used herein, the term "flavor modulating compound" refers to a compound that has a weak or barely noticeable flavor characteristic by itself at the concentrations employed, but that can modify, complement, modulate or contribute to the taste impact of other flavor substances contained in the flavor composition or consumer product, including salty impact, sour impact, bitter impact and / or umami impact.

[0031] For example, a flavor-modulating compound has no salty taste at less than 40 ppm. The compound may have a slight salty taste at levels between 50 ppm and 100 ppm. At higher levels, for example, at about 1000 ppm, the compound may still have only a weak salty taste. In combination with a salty flavor compound, for example NaCl, the perception of salty taste can be enhanced.

[0032] For example, flavor-modulating compounds have no discernible taste at levels below 40 ppm to counteract or mask bitterness.At higher levels, for example at about 1000 ppm, compounds may have strong bitterness.When used in combination with compounds that may have bitter off-taste, such as KCl, for example at levels between 50 ppm and 100 ppm, compounds can reduce bitterness.

[0033] For example, flavor modulating compounds do not impart umami taste at levels below 40 ppm. When employed in combination with compounds that can impart umami taste, such as MSG, for example at levels between 50 ppm and 100 ppm, the umami taste is enhanced.

[0034] For example, flavour modulating compounds may impact acidity and freshness.

[0035] As used herein, the term "flavoring substance" refers to any substance capable of imparting a detectable flavor impact, preferably at a concentration of less than 0.1 wt%, more preferably less than 0.01 wt%. For example, such flavoring substances can be selected from natural flavors, artificial flavors, spices, seasonings, etc., synthetic flavor oils and flavor aromatics and / or oils, oleoresins, essential oils, distillates, and extracts derived from plants, leaves, flowers, fruits, etc. In general, any flavor or food additive can be used, such as those described in Chemicals Used in Food Processing, publication 1274, pages 63-258, by the National Academy of Sciences. This publication is incorporated herein by reference.

[0036] The flavor modulating compounds of the present invention have been found to be extremely useful ingredients capable of imparting appreciated taste sensations, in the presence of other flavoring substances, to products into which they are incorporated, specifically "roundness," "richness," "materiality," "clarity," "complexity," "expansive," "continuous," "long-lasting," "tingling," "numbing," "bitter," and / or "metallic." Thus, the present taste improving substances can be employed to improve the taste (including "mouthfeel") of foodstuffs and beverages.

[0037] In one aspect of the invention there is provided one or more compounds of formula (I) and their use as flavour modifying compounds in edible salts, wherein one of R1 and R2 is H; and the other of R1 and R2 is independently selected from the group consisting of linear or branched C1-C18 hydrocarbon radicals having up to 3 O atoms and / or having up to 1 double bond and / or having up to 1 ring; or wherein R1 and R2 together with the carbon atoms to which they are attached form an aromatic six-membered hydrocarbon ring.

[0038] In one aspect of the invention there is provided a compound according to formula (I) and its use as a flavour modulating compound in edible salt, wherein one of R1 and R2 is H; the other of R1 and R2 is selected from the group consisting of Me, Et, n-Pr, iso-Pr, n-Bu, iso-Bu, sec-Bu, tert-Bu, hexadecyl, octadecyl, ethenyl, 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 hydrocarbon ring.

[0039] In one embodiment of the present invention, there is provided a compound according to formula (I) as defined above and its use as flavour modifying compound in edible salt, wherein the compound of formula (I) is selected from the group consisting of 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-ethenyl-1H-imidazole, 4-propenyl-1H-imidazole, 4-octadecyl-1H-imidazole, 1H-imidazole-4-capryloxy-1H-imidazole, 4-phenyl ... wherein the compound is selected from the group consisting of carbaldehyde, 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)propanoic acid, 3-(1H-imidazol-4-yl)acrylic acid, 4-(1H-imidazol-4-yl)butanoic acid, and benzimidazole.

[0040] In particular, there is provided the use of a compound according to formula (I), wherein the compound according to formula (I) is selected from the group consisting of 1H-imidazole, 4-methyl-1H-imidazole, 3-(1H-imidazol-4-yl)acrylic acid (urocanic acid), 2-(1H-imidazol-4-yl)acetic acid, and benzimidazole.

[0041] 1H-imidazole is a well-known compound and is an important component in pharmaceutical and agrochemical compounds. So far, no taste or taste-modulating properties have been reported in the literature. 4-Methyl-1H-imidazole is present in caramel coloring, which is widely used in foodstuffs and beverages. However, no information is available on the taste or taste-modulating properties of the compound. 3-(1H-imidazol-4-yl)acrylic acid (urocanic acid) is a known compound in the field of skin care. Benzimidazole is known as a starting material for the synthesis of many pharmaceuticals.

[0042] In a further aspect of the present invention there is provided the use of a mixture of two or more compounds according to formula (I) as defined above as a flavour modulating compound.

[0043] In a further embodiment, the flavor modulating compounds according to the present invention are particularly useful in a wide variety of flavor compositions and consumer products, including savory foods, non-savory foods, such as dairy products, beverages, and confectioneries.

[0044] For example, the flavour composition comprises at least 0.01 wt%, or at least 0.1 wt%, or at least 0.5 wt% of a flavouring substance, based on the total weight of the composition, and between 0.001 wt% and 80 wt% of a flavour modulating compound according to the present invention, preferably between 0.01 wt% and 50 wt%, more preferably between 0.01 wt% and 20 wt%, of a flavour modulating compound, based on the total weight of the composition.

[0045] In a typical flavour composition, the flavour modifying compound and the flavouring substance are employed in a weight ratio within the range of from 10:1 to 1:150, preferably from 5:1 to 1:100.

[0046] The flavour composition comprising the flavour modulating compound may suitably be prepared in the form of a liquid, a paste or a powder, for example the flavour composition is a free-flowing powder.

[0047] Typical examples of flavor compositions include savory flavors, sour / acid flavors and others.

[0048] For example, the flavour composition is a reduced salt flavour composition.

[0049] The flavor modulating compounds of the present invention can be used in flavor compositions in combination with one or more ingredients or excipients that are conventionally used in flavor compositions in addition to flavoring substances, such as carrier materials and other auxiliaries commonly used in the art.Excipients suitable for flavor compositions are well known in the art, and include, for example, without limitation, solvents (including water, alcohol, 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.

[0050] 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", J. Nikitakis (ed.), 1st ed., The Cosmetic, Toiletry and Fragrance Association, Inc., Washington, 1988.

[0051] Other suitable and desirable ingredients of the flavour composition are described in standard texts, such as Handbook of Industrial Chemical Additives”, ed. M. and I. Ash, 2nd Ed., (Synapse 2000).

[0052] In another aspect of the present invention, there is further provided a consumer 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.

[0053] By "product base" is meant the combination of all conventional, art-recognized ingredients required for a particular consumable composition.

[0054] In another aspect of the present invention, there is provided a consumer product selected from the group consisting of foodstuffs and beverages, the consumer product comprising at least 1 ppm, preferably at least 50 ppm, more preferably at least 100 ppm or 200 ppm of one or more flavour modulating compounds according to formula (I) and / or an edible salt thereof.

[0055] 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%, and most preferably at least 0.02 wt% of one or more flavor modulating compounds. Typically, the product contains no more than 0.05 wt%, preferably no more than 0.0.25 wt% of the flavor modulating compounds.

[0056] For example, consumer products have a reduced salt content.

[0057] Typical examples of foodstuffs according to the present invention include soups, sauces, stocks, bouillons, cheese products, dressings, condiments, margarines, noodles, and beverages.

[0058] The flavour modulating compounds according to the invention can be advantageously applied to impart desired taste attributes to the aforementioned products, in addition they are capable of modulating the taste impact of other flavour ingredients contained within these same products, thereby improving the overall flavour quality of these products.

[0059] In another aspect of the 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 and may be provided in liquid or solid form.

[0060] In another aspect of the present invention, there is provided a method for imparting, enhancing, improving or modifying the flavor characteristics of a flavor composition or consumer product, comprising adding to said composition or consumer product at least one flavor modulating compound, which is a compound of formula (I) or an edible salt thereof. For example, the flavor modulating compound is added in an amount of at least 0.001 wt%, preferably at least 0.01 wt%.

[0061] The preparation of the compounds of the invention can be carried out by methods known in the art, for example the compounds can be obtained by chemical or enzymatic reactions.

[0062] The invention will now be further described with reference to the following non-limiting examples, it will be understood that these examples are for the purpose of illustration only and that variations and modifications may be made by those skilled in the art.

[0063] example General: 1H-imidazole (CAS number 288-32-4), 4-methyl-1H-imidazole (CAS number 822-36-6), (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid (3-(1H-imidazol-4-yl)acrylic acid or urocanic acid, CAS number 104-98-3), 2-(1H-imidazol-4-yl)acetic acid (CAS number 645-65-8) and benzimidazole (CAS number 51-17-2) are commercially available, for example from Sigma-Aldrich.

[0064] In the following examples, concentrations are given in weight percent.

[0065] Example 1: Taste 1H-imidazole was tasted at different concentrations in water by a sensory panel. No effect was noted up to concentration levels of 40 ppm, but at 50 ppm a subtle salty taste was detectable. At a concentration level of 100 ppm the compound has a weak salty taste along with some astringency and sourness. The saltiness of 1H-imidazole at a concentration level of 100 ppm is comparable to 0.05% NaCl in water, however the saltiness is flat and does not match all aspects of NaCl. At a concentration level of 1000 ppm a weak salty taste is still perceived, but is predominantly bitter.

[0066] Example 2: Salt Intensification Two aqueous solutions were prepared. A) 0.3% NaCl, and B) 0.3% NaCl and 100 ppm 1H-imidazole. The solutions were tasted by a sensory panel. Solution A was described as "salty". Solution B was described as significantly saltier, with mineral notes, less acidity, some astringency and freshness.

[0067] Example 3: Increasing umami flavor Two aqueous solutions were prepared. A) 0.5% NaCl, 0.03% MSG, 0.007% ribotide, and B) 0.5% NaCl, 0.03% MSG, 0.007% ribotide and 100 ppm 1H-imidazole. The solutions were tasted by a sensory panel. Solution A was a model solution for savory taste, containing MSG (monosodium glutamate) and ribotide (IMP / GMP, 50 / 50 mixture) as savory taste enhancers. Solution B was described as having a strong boost in saltiness and umami compared to solution A.

[0068] Example 4: Bitterness masking Two aqueous solutions were prepared. A) 0.3% KCl, and B) 0.3% KCl and 70 ppm 1H-imidazole. The solutions were tasted by a sensory panel. Solution B was described as less metallic and more salty compared to solution A.

[0069] Example 5: Effect on broth A model broth base containing 0.3% NaCl was compared to a sample that further contained 100 ppm 1H-imidazole. The solutions were tasted by a sensory panel and the samples containing the additional 1H-imidazole were described as more mineral and salty as well as more umami tasting compared to the model broth base.

[0070] Example 6: Effect on cheese sauce The effect of 1H-imidazole on a commercial cheese sauce was investigated. Thus, a sensory panel compared the cheese sauce with a sample of the sauce that further contained 70 ppm of 1H-imidazole. Sauces containing additional 1H-imidazole were described as more mineral and salty.

[0071] Example 7: Combination with other taste-modulating compounds A combination of taste modulating compounds was added to a 0.3% NaCl solution in water. A) 100 ppm 1H-imidazole and 50 ppm N-lactoylethanolamine; B) 100 ppm 1H-imidazole and 0.04 ppm N-oleoylmethionine; C) 100 ppm 1H-imidazole and 50 ppm ((2E)-3-(1H-imidazol-4-yl)-N-[2-(1H-imidazol-4-yl)ethyl]prop-2-enamide); and D) 100 ppm 1H-imidazole, 50 ppm N-lactoylethanolamine, 0.04 ppm N-oleoylmethionine, and 50 ppm ((2E)-3-(1H-imidazol-4-yl)-N-[2-(1H-imidazol-4-yl)ethyl]prop-2-enamide).

[0072] The samples were tasted by a sensory panel and evaluated against a 100 ppm solution of 1H-imidazole in 0.3% NaCl solution. Sample A was described as exhibiting a more salty and mineral taste. Sample B was perceived as even saltier. Sample C had a boosted saltiness. Sample D performed best in terms of saltiness.

[0073] Example 8: Effect on potato chips Potato chips with 1.5% salt were tasted by a sensory panel with and without 1H-imidazole. Potato chips containing 70 ppm 1H-imidazole had a stronger salty impact and a longer lasting effect compared to potato chips without 1H-imidazole.

[0074] Example 9: Effect on mayonnaise Samples of commercial mayonnaise with and without added 1H-imidazole were compared by a sensory panel. Compared to pure mayonnaise, the sample containing 70 ppm 1H-imidazole was noted to be noticeably saltier and had a stronger sour taste profile.

[0075] Example 10: Effect on cone curl Corn curls with cheese flavor with and without added 1H-imidazole were compared by a sensory panel. The taste of corn curls with 100 ppm 1H-imidazole was described as having an enhanced saltier, richer profile compared to curls without 1H-imidazole.

[0076] Example 11: Effects on vegan burgers Soy-based vegan burgers with and without 1H-imidazole were tasted by a sensory panel. The burger with 70 ppm 1H-imidazole is described as saltier compared to the version without, retaining the first peak of saltiness and the final saltiness phase.

[0077] Example 12: Salt Intensification Two aqueous solutions were prepared. A) 0.5% NaCl, and B) 0.5% NaCl and 50 ppm 4-methyl-1H-imidazole. The solutions were tasted by a sensory panel. Solution A was described as "salty". Solution B was described as saltier compared to solution A.

[0078] Example 13: Salt enhancement Two aqueous solutions were prepared. A) 0.5% NaCl, and B) 0.5% NaCl and 50 ppm (2E)-3-(1H-imidazol-4-yl)prop-2-enoic acid (urocanic acid). The solutions were tasted by a sensory panel. Solution A was described as "salty". Solution B was described as saltier compared to solution A.

[0079] Example 14: Taste 2-(1H-imidazol-4-yl)acetic acid and benzimidazole were tasted at different concentrations in water by a sensory panel. At a concentration of 30 ppm of benzimidazole a subtle salty and sour taste could be detected. At a concentration level of 70 ppm the compound has a weak salty taste with some sour background. For 2-(1H-imidazol-4-yl)acetic acid, a subtle salty and mineral taste could be detected at a concentration of 30 ppm. At a concentration level of 90 ppm, the compound has a weak salty, mineral taste, and a slight sour note. The saltiness of both compounds at a concentration level of 70 ppm is comparable to 0.05% NaCl in water.

[0080] Example 15: Salt enhancement The following aqueous solutions were prepared: A) 0.3% NaCl; B) 0.3% NaCl and 90 ppm 2-(1H-imidazol-4-yl)acetic acid, and C) 0.3% NaCl and 80 ppm benzimidazole. The solutions were tasted by a sensory panel. Solution A was described as "salty". Solution B was described as being noticeably saltier with mineral notes and solution C was described as being noticeably saltier with a sour fresh background.

[0081] Example 16: Bitterness masking The following aqueous solutions were prepared: A) 0.3% KCl, and B) 0.3% KCl and 100 ppm 2-(1H-imidazol-4-yl)acetic acid, and C) 0.3% KCl and 100 ppm benzimidazole. The solutions were tasted by a sensory panel. Solutions B and C were described as less bitter, less metallic, and more salty compared to solution A. Both compounds are good masking agents for KCl. Solution B was preferred over solution C.

[0082] Example 17: Effect on broth A model broth base containing 0.3% NaCl was compared with samples further containing 70 ppm 2-(1H-imidazol-4-yl)acetic acid and 100 ppm benzimidazole, respectively. The solutions were tasted by a sensory panel. Samples containing additional 2-(1H-imidazol-4-yl)acetic acid or benzimidazole were described as more mineral and salty compared to the model broth base. The solutions containing benzimidazole were preferred.

[0083] Example 18: Effect on cheese sauce The effect of 2-(1H-imidazol-4-yl)acetic acid on a commercial cheese sauce was investigated. Thus, the cheese sauce was compared by a sensory panel with a sample of the sauce that further contained 50 ppm of 2-(1H-imidazol-4-yl)acetic acid. A sauce additionally containing 2-(1H-imidazol-4-yl)acetic acid, which has more salty and umami characteristics, was preferred.

[0084] Example 19: Combination with other taste-modulating compounds A combination of taste modulating compounds was added to a 0.3% NaCl solution in water. A) 50 ppm 2-(1H-imidazol-4-yl)acetic acid and 50 ppm N-lactoylethanolamine; B) 50 ppm 2-(1H-imidazol-4-yl)acetic acid and 0.04 ppm N-oleoylmethionine; C) 50 ppm 2-(1H-imidazol-4-yl)acetic acid, 50 ppm N-lactoylethanolamine, and 0.04 ppm N-oleoylmethionine; D) 50 ppm 2-(1H-imidazol-4-yl)acetic acid, 50 ppm N-lactoylethanolamine, 0.04 ppm N-oleoylmethionine, and 50 ppm ((2E)-3-(1H-imidazol-4-yl)-N-[2-(1H-imidazol-4-yl)ethyl]prop-2-enamide); E) 50 ppm benzimidazole and 50 ppm N-lactoylethanolamine; F) 50 ppm benzimidazole and 0.04 ppm N-oleoylmethionine; G) 50 ppm benzimidazole, 50 ppm N-lactoylethanolamine, 0.04 ppm N-oleoylmethionine, H) 50 ppm benzimidazole, 50 ppm N-lactoylethanolamine, 0.04 ppm N-oleoylmethionine, and 50 ppm ((2E)-3-(1H-imidazol-4-yl)-N-[2-(1H-imidazol-4-yl)ethyl]prop-2-enamide);

[0085] The samples were tasted by a sensory panel and evaluated against a solution of 50 ppm of each imidazole derivative in 0.3% NaCl solution. Sample A was described as having an enhanced salty effect and long-lasting mineralized properties. Sample B was also perceived as saltier than the blend of 2-(1H-imidazol-4-yl)acetic acid and salt. Sample C had good salinity enhancement and a rounded, balanced effect. Sample D performed best in terms of balance and saltiness. Sample E was described as having an enhanced salty effect and long-lasting mineralized qualities, an effect that was more favorable than that of Sample A. Sample F was perceived to resemble a blend of benzimidazole and salt. Sample G had good salinity enhancement and a rounded, balanced effect. Sample H was perceived as similar to Sample G.

[0086] Example 20: Effect on mayonnaise Samples of commercial mayonnaise with and without the addition of 2-(1H-imidazol-4-yl)acetic acid or benzimidazole were compared by a sensory panel. Compared to pure mayonnaise, samples containing 70 ppm of 2-(1H-imidazol-4-yl)acetic acid or benzimidazole were noted to have a noticeably saltier and less sour impression.

[0087] Example 21: Effect on cone curl Corn curls with cheese flavor with and without the addition of 2-(1H-imidazol-4-yl)acetic acid or benzimidazole were compared by a sensory panel. The taste of corn curls supplemented with 150 ppm of 2-(1H-imidazol-4-yl)acetic acid or benzimidazole was described as having an enhanced saltier, richer profile compared to curls without the added compound.

[0088] Example 22: Effect on ketchup Commercial ketchup samples with and without added 2-(1H-imidazol-4-yl)acetic acid or benzimidazole were compared by a sensory panel. Compared to pure ketchup, the sample containing 100 ppm 2-(1H-imidazol-4-yl)acetic acid was described as significantly saltier, had a longer-lasting sour taste, and was less sweet. The sample containing 70 ppm benzimidazole was also described as significantly saltier.

Claims

1. One or more compounds of formula (I) and their use as flavour modifying compounds in edible salts: 【Chemistry 1】 During the ceremony R 1 and R 2 is independently selected from the group consisting of H, a linear 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 1 double bond and / or has up to 1 ring; Or, in the formula, R 1 and R 2 together with the carbon atom to which they are attached form an aromatic six-membered hydrocarbon ring.

2. R 1 and R 2 is independently selected from the group consisting of H, Me, Et, n-Pr, iso-Pr, n-Bu, iso-Bu, sec-Bu, tert-Bu, hexadecyl, octadecyl, ethenyl, propenyl, octadecenyl, formyl, 2-oxoethyl, 3-oxopropyl, carboxyl, carboxymethyl, carboxy(hydroxy)methyl, carboxycarbonyl, 2-carboxyethyl, 2-carboxyvinyl, and 3-carboxypropyl, or R 1 and R 2 The use according to claim 1 , wherein, together with the carbon atom to which they are attached, form an aromatic six-membered ring.

3. The compounds are 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-ethenyl-1H-imidazole, 4-propenyl-1H-imidazole, 4-octadecenyl-1H-imidazole, 1H-imidazole-4-carbaldehyde, 2-(1H-imidazol-4-yl)acetaldehyde, 3-(1H 3. The use according to claim 1 or 2, wherein the 2-(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)propanoic acid, 3-(1H-imidazol-4-yl)acrylic acid, 4-(1H-imidazol-4-yl)butanoic acid, and benzimidazole.

4. The use according to any one of claims 1 to 3, wherein the compound is used as a salt enhancing compound.

5. Use according to any one of claims 1 to 4, wherein the compound is used as a sourness-impacting compound and / or a bitterness-masking compound and / or an umami-enhancing compound.

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

7. 7. A flavour composition according to claim 6, comprising the compound at between 0.001wt% and 80wt% of the flavour composition.

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

9. 9. The consumer product of claim 8, wherein the compound comprises about 0.001-0.05 wt% of the consumer product.

10. 9. The consumer product of claim 8, wherein the consumer product is selected from foodstuffs and beverages.

11. 10. A method for imparting, enhancing, improving or modifying the flavor characteristics of a flavor composition or consumer product, the method comprising adding to said composition or consumer product at least one compound as defined in claims 1 to 3.

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

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

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