Classifications

• • A23L1/22657—
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
  • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
  • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
  • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/204—Aromatic compounds
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/205—Heterocyclic compounds
  • A23L27/2052—Heterocyclic compounds having oxygen or sulfur as the only hetero atoms
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/88—Taste or flavour enhancing agents
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
  • C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
  • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
  • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
  • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
  • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
  • C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

• the present invention relates to the field of taste. More particularly, it concerns the use of certain cinnamic acid derived amides as taste-enhancing ingredients to impart or reinforce the tastes known as kokumi or umami.
• the present invention also concerns compositions or articles containing at least one of the aforementioned compounds.
• Zanthoxylum rubescens (Rutaceae) [Amides from Zanthoxylum Rubescens . Adesina, S. K.; Reisch, J. Phytochem. 1989, 3, 839-842.] or Piperaceae [Chemical constituents of peppers ( Piper spp.) and application to food preservation: naturally occurring antioxidative compounds. Nakatani, N.; Inatani, R.; Ohta, H.; Nishioka, A., Environ. Health Perspectives 1986, 67, 135-142].
• vanilloid amides such as capsaicin or piperine are usually found in pepper or capsicum species, they generally have a pungent or hot taste. It would be desirable to avoid this.
• US2003/0152682 (Bayer Polymers LLC) and EP 1 323 356 (Symrise) disclose the use of ferullic acid amides as pungent compounds or heat generating-system for oral hygiene products. Included in this document is the compound trans-rubenamine, but it is not described or even suggested to have an umami taste.
• EP 2 138 152 (to Henkel) describes mouthwash compositions containing ferrulic acid derived amides among other amides or pungent, or cooling compounds.
• none of these documents anticipate, report or suggest that the compounds described therein have organoleptic properties that can be used to impart or reinforce a kokumi or umami taste.
• Kokumi and umami are now established descriptors in the field of taste and are known to supplement, enhance, or modify the taste and/or aroma of a food without necessarily having a strong characteristic taste or aroma of their own.
• a desire for kokumi and umami exists for a wide range of foods like soups, sauces, savory snacks, prepared meals, condiments, etc. Moreover, they are often found to complement or enhance foodstuffs which have a savory or salty characteristic and, as a result, may be useful where sodium or salt reduction is desired.
• Umami is one of the five basic tastes sensed by specialized receptor cells present on the human tongue. Umami applies to the sensation of savoriness, and particularly to the detection of glutamates and/or ribotides which are common in meats, cheese and other protein-rich foods. The behavior of umami receptors explains why foods containing monosodium glutamate (MSG) often taste “fuller”. However, some consumers are apparently sensitive to MSG and may suffer from headaches or other illnesses upon consuming it. Thus replacement of MSG, at least partially, can be desirable.
• MSG monosodium glutamate
• Kokumi has been described variously as “deliciousness”, “continuity”, “mouthfulness”, “mouthfeel” and “thickness”. It exists naturally in a variety of foods such as cheese, giving a ‘mature’ cheese taste; vegetable flavors, particularly tomato; meat, where it gives a fullness and longer lasting taste; mayonnaise & dressings, where it can round out acid notes; fat-reduced food products, where it gives a similar fullness to full-fat products; herbs and spice; and soups, especially miso soup.
• a certain class of cinnamic acid derived amide derivatives can be used as flavor or taste enhancing ingredients, for instance to impart or reinforce the kokumi or umami taste of a flavoring composition or of a flavored food.
• the present invention provides the use of a compound of formula
• any one of its stereoisomers or the similar, it is meant the normal meaning understood by a person skilled in the art, i.e. that the invention's compound can be a pure enantiomer (if chiral) or diastereomer (e.g. the double bond is in a conformation E or Z).
• dotted line represents carbon-carbon single or double bond
• the expression “wherein the dotted line represents carbon-carbon single or double bond”, or the similar it is meant the normal meaning understood by a person skilled in the art, i.e. that the whole bonding (solid and dotted line) between the carbon atoms connected by said dotted line is a carbon-carbon single or double bond.
• One advantage of the present invention is that the compounds confer umami and/or kokumi taste to a product without detrimentally affecting the flavor profile of the product.
• said compound (I) is selected from the group of compounds in which
• n is 0 or 1; the dotted line represents carbon-carbon single or double bond; and each of R 1 to R 4 , taken independently from each other, represents a hydrogen atom or represents a R 5 or OR 5 group, R 5 representing a C 1 to C 5 , or even a C 1 to C 3 , alkyl group.
• said compound (I) is selected from the group of compounds in which R 1 and R 2 both represent methoxy groups and n is 1.
• said dotted line represents a carbon-carbon double bond.
• said compound (I) is a compound of formula
• each of R 3 or R 4 taken independently from each other, represents a hydrogen atom or represents a R 5 or OR 5 group, R 5 representing a C 1 to C 5 , or even a C 1 to C 3 alkyl group.
• R 3 represents a hydrogen atom or represents a R 5 or OR 5 group
• R 4 represents a R 5 or OR 5 group
• R 5 representing a C 1 to C 5 , or even a C 1 to C 3 , alkyl group.
• R 3 represents a hydrogen atom or represents a R 5 group
• R 4 represents a R 5 or OR 5 group
• R 5 representing a C 1 to C 5 , or even a C 1 to C 3 , alkyl group.
• R 3 represents a hydrogen atom or represents a R 5 group
• R 4 represents a R 5 , R 5 representing a C 1 to C 5 , or even a C 1 to C 3 , alkyl group.
• R 5 represents a methyl, ethyl, propyl or iso-propyl group.
• R 3 represents a hydrogen atom or represents a C 1 to C 5 , or even a C 1-3 , alkyl group or a OR 6 group, R 6 representing a C 1 to C 5 , or even a C 2-3 , alkyl group; and R 4 represents a C 1 to C 5 , or even a C 1-3 , alkyl group or a OR 6 group, R 6 representing a C 1 to C 5 , or even a C 1-3 , alkyl group; are also novel compounds and therefore they represent another aspect of the invention.
• said novel compounds are those wherein R 3 represents a hydrogen atom or a C 1-3 , alkyl group and R 4 represents a C 1-3 , alkyl group or OR 6 group, R 6 representing a C 1 to C 3 alkyl group.
• said compound (I) or (II) is a C 19-25 compound, or even a C 19-22 compound.
• the non-aromatic carbon-carbon double bond of compound (I) or (II) can be in a configuration Z or E or a mixture thereof.
• said compound (I) or (II) is in the form of a mixture of the E and Z stereoisomers, said mixture comprising at least 50% w/w, or at least 80% w/w, of the stereoisomer E, the remaining being essentially the Z stereoisomer.
• said compound (I) is selected amongst (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide (referenced in the Examples as Amide 1), (E)-3-(3,4-dimethoxyphenyl)-N-(3-methoxyphenethyl)acrylamide (referenced in the Examples as Amide 4), (E)-3-(3,4-dimethoxyphenyl)-N-(3-ethoxyphenethyl)acrylamide (referenced in the Examples as Amide 7), (E)-3-(3,4-dimethoxyphenyl)-N-(3-propoxyphenethyl)acrylamide (referenced in the Examples as Amide 8), (E)-3-(3,4-dimethoxyphenyl)-N-(4-isopropoxy-phenethyl)acrylamide (referenced in the Examples as Amide 9), (E)-3-(3,4-dimethoxy
• the compounds of the invention can be used alone or in mixtures and provide a strong kokumi or umami taste at exceptionally low levels.
• the invention concerns the use of a compound of formula (I) as a taste-conferring or enhancing ingredient, and in particular to impart or reinforce kokumi or umami taste.
• said compound (I) is used to impart or reinforce kokumi or umami taste as well as to enhance the saltiness and/or savory perception of a flavor.
• such use is very much appreciated by flavorists to impart or enhance the kokumi or umami taste in savory flavors, such as beef, chicken, pork, and seafood.
• savory flavors such as beef, chicken, pork, and seafood.
• compounds according to formula (I) are also found to enhance the perception of sweetness and longevity of the flavor.
• the compounds according to formula (I) are found to enhance perception of fattiness and tallow notes. Additionally we found that said compounds can increase juiciness in meat based products.
• the present invention concerns a method to confer, enhance, improve or modify the taste properties, as indicated above, of a flavoring composition or of a flavored article, which method comprises adding to said composition or article an effective amount of at least a compound of formula (I).
• use of a compound of formula (I) includes the use of any composition containing compound (I) and which can be advantageously employed in the flavor industry as active ingredient.
• the invention provides a taste-modifying composition comprising:
• flavor carrier we mean here a material which is substantially neutral from a flavor point of view, insofar as it does not significantly alter the organoleptic properties of flavoring ingredients.
• the carrier may be a liquid or a solid.
• Suitable liquid carriers include, for instance, an emulsifying system, i.e. a solvent and a surfactant system, or a solvent commonly used in flavors. A detailed description of the nature and type of solvents commonly used in flavor cannot be exhaustive.
• Suitable solvents include, for instance, propylene glycol, triacetine, triethyl citrate, benzylic alcohol, ethanol, vegetable oils or terpenes.
• Suitable solid carriers include, for instance, absorbing gums or polymers, or even encapsulating materials.
• materials may comprise wall-forming and plasticizing materials, such as mono, di- or trisaccharides, natural or modified starches, hydrocolloids, cellulose derivatives, polyvinyl acetates, polyvinylalcohols, proteins or pectins, or yet the materials cited in reference texts such as H. Scherz, Hydrokolloids: Stabilisatoren, Dickungs- and Geherstoff in Struktur, Band 2 der Kunststoffen Herbert Strukturchemie,maschineoughough, 1996.
• Encapsulation is a well known process to a person skilled in the art, and may be performed, for instance, using techniques such as spray-drying, agglomeration, extrusion, coacervation and the like.
• flavor base we mean here a composition comprising at least one flavoring ingredient.
• flavoring ingredient is not a compound of formula (I).
• flavoring ingredient it is meant here a compound, which is used in flavoring preparations or compositions to impart a hedonic effect.
• an ingredient to be considered as being a flavoring one, must be recognized by a person skilled in the art as being able to impart or modify in a positive or pleasant way the taste of a composition, and not just as having a taste.
• flavoring co-ingredients present in the base do not warrant a more detailed description here, the skilled person being able to select them on the basis of its general knowledge and according to intended use or application and the desired organoleptic effect.
• these flavoring co-ingredients belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitriles, terpenoids, nitrogenous or sulphurous heterocyclic compounds and essential oils, and said perfuming co-ingredients can be of natural or synthetic origin. Many of these co-ingredients are in any case listed in reference texts such as the book by S.
• said flavor base comprises another umami imparting flavor ingredient, such as MSG (mono sodium glutamate), and ribotides (a blend, e.g. 50-50 w/w, of IMP (inosine monophosphate) and GMP (guanosine monophosphate)), for example in a MSG/ribotides w/w ratio from 95/5 to 90/10.
• MSG mono sodium glutamate
• ribotides a blend, e.g. 50-50 w/w, of IMP (inosine monophosphate) and GMP (guanosine monophosphate)
• flavor adjuvant we mean here an ingredient capable of imparting additional added benefit such as a color, a particular light resistance, chemical stability, and so on. A detailed description of the nature and type of adjuvant commonly used in flavoring bases cannot be exhaustive. Nevertheless, such adjuvants are well known to a person skilled in the art, but it has to be mentioned that said ingredients are well known to a person skilled in the art.
• a composition consisting of at least one compound of formula (I) and at least one flavor carrier represents a particular embodiment of the invention as well as a flavoring composition comprising at least one compound of formula (I), at least one flavor carrier, at least one flavor base, and optionally at least one flavor adjuvant.
• more than one compound of formula (I) is used in combination since it is found that a synergistic enhancement of the kokumi or umami taste can be achieved in this way. Moreover, it is found that the combination of ingredients can provide the desired kokumi or umami taste without imparting undesirable flavor notes.
• a compound of formula (I) can be advantageously incorporated into flavored articles to positively impart, or modify, the kokumi or umami taste of said articles.
• the present invention provides a flavored article comprising:
• Suitable foodstuff bases e.g. foods or beverages, can be fried or not, as well as frozen or not, low fat or not, marinated, battered, chilled, dehydrated, instant, canned, reconstituted, retorted or preserved.
• Typical examples of said foodstuff bases include:
• Particularly preferred foodstuffs in which the compound according to formula (I) finds utility include those having topnotes such as seafood, beef, chicken, vegetables, cheese, fat, tallow and/or marrow are important.
• a flavored article according to the invention comprises one or more compounds according to formula (I), as well as optional benefit agents, corresponding to taste and flavor profile of the desired edible product, e.g. a savory cube.
• the taste-modifying composition and the flavored article according to the invention comprise as taste conferring or modifying ingredient a compound of formula (II) wherein R 3 represents a hydrogen atom or represents a R 5 group, and R 4 represents a R 5 or OR 5 group, R 5 representing a C 1 to C 3 alkyl group.
• R 5 represents a methyl, ethyl, propyl or iso-propyl group.
• the proportions in which the compounds according to the invention can be incorporated into the various aforementioned articles or compositions vary within a wide range of values. These values are dependent on the nature of the article to be flavored and on the desired organoleptic effect as well as the nature of the co-ingredients in a given base when the compounds according to the invention are mixed with flavoring co-ingredients, solvents or additives commonly used in the art.
• concentrations are in the order of 0.05% to 30%, more preferably 0.1% to 20%, most preferably 0.1% to 10%, of the compounds of the invention based on the weight of the flavoring compositions into which they are incorporated.
• the acid (E)-3-(3,4-dimethoxyphenyl)acrylic acid (typically 33 mmol) and DIEA (diisopropyl ethyl amine, 2 equiv.) were diluted in 200 mL of EtOAc and 50 mL of dichloromethane. The solution was cooled to 15° C. and ethyl chloroformate (1 molar equiv.) was added drop wise. The reaction was stirred for 1 hour before the starting amine (1 molar equiv., diluted 2-3 times in EtOAc) was added. The reaction was stirred overnight at room temperature.
• the amides were evaluated at 20 ppm in mineral water in comparison with 0.05% monosodium glutamate (MSG).
• MSG monosodium glutamate
• the trained panelists (5-10) were giving an umami taste intensity note.
• the Relative umami intensity (RUI) was calculated as follows:
• Amides 1, 3, 4 and 8 were blended and diluted in maltodextrin at 10% w/w.
• Sol 8 Sol 9 Sol 10 Sol 11 Sol 12 Sol 13 MSG 500 500 500 500 500 500 Amide 7 20 — — — — — — Amide 9 — 20 — — — — Amide 10 — — 20 — — — Amide 11 — — — 20 — — Amide 12 — — — — 20 — Amide 17 — — — — — — 20 Sol solution
• a panel consisted in 15 to 20 trained panelists evaluating the samples for taste properties on a scale of ⁇ 5 to 5 ( ⁇ 5 denoted no umami effect and 5 denoted extremely strong umami effect, 0 being the umami intensity of a reference umami solution containing Monosodium Glutamate at 0.05%).
• the samples were evaluated with and without nose clip to focus on taste.
• a beef stock was prepared containing the following ingredients:
• the bouillons were presented to 5 trained panelists on a blind test basis. They were asked to rate the samples for taste properties on a scale of 0 to 10 (0 denoted no umami effect and 10 denoted extremely strong umami effect). The results are reported herein below:
• a chicken stock was prepared containing the following ingredients:
• a chicken bouillon was prepared containing the following ingredients:
• a marinade was prepared containing the following ingredients:
• Samples were tumbled under vacuum for 25 minutes, and then cooked in a steam oven until meat temperature reaches 75° C. Samples were then frozen and reheat for 20 minutes at 80° C. in the oven before evaluation.
• the dry ingredients (salt, starches) were first put in a bowl chopper. The ice mix was added until homogenous. The surimi base was then added and mixed for 3 minutes. The oil was added while mixing, followed by the egg white.
• Surimi 1 Surimi 2
• Surimi 3 Surimi 4 MSG — 5000 ppm — — Amide 1 — — 50 ppm — Amide 3 — — — 50 ppm
• the 4 surimis were put in cooking bags and cooked for 45 minutes in a steam oven at 90° C. The samples were then quickly cooled down.

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