(19)
(11)EP 2 725 927 B2

(12)NEW EUROPEAN PATENT SPECIFICATION
After opposition procedure

(45)Date of publication and mention of the opposition decision:
04.12.2019 Bulletin 2019/49

(45)Mention of the grant of the patent:
04.03.2015 Bulletin 2015/10

(21)Application number: 12726105.5

(22)Date of filing:  06.06.2012
(51)Int. Cl.: 
A23L 27/20  (2016.01)
C07C 235/34  (2006.01)
C07D 317/60  (2006.01)
(86)International application number:
PCT/EP2012/060641
(87)International publication number:
WO 2013/000673 (03.01.2013 Gazette  2013/01)

(54)

TASTE MODIFYING PRODUCT

GESCHMACKSMODIFIZIERENDES PRODUKT

PRODUIT MODIFIANT LE GOÛT


(84)Designated Contracting States:
AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

(30)Priority: 30.06.2011 EP 11172035
16.01.2012 EP 12151273

(43)Date of publication of application:
07.05.2014 Bulletin 2014/19

(60)Divisional application:
15154597.7 / 2912954

(73)Proprietor: Firmenich SA
1211 Geneva 8 (CH)

(72)Inventors:
  • FREROT, Eric
    CH-1211 Geneva 8 (CH)
  • AEBERHARDT, Kasia
    CH-1211 Geneva 8 (CH)

(74)Representative: Rupp, Christian 
Mitscherlich PartmbB Patent- und Rechtsanwälte Postfach 33 06 09
80066 München
80066 München (DE)


(56)References cited: : 
EP-A1- 2 064 959
EP-A2- 1 323 356
US-A- 6 117 365
US-A1- 2004 202 619
US-A1- 2007 208 083
EP-A1- 2 529 632
US-A- 1 329 272
US-A1- 2003 152 682
US-A1- 2006 057 268
  
  • ADESINA, S.K., REISCH, J.: "Amides from Zanthoxylum Rubescens", PHYTOCHEMISTRY, vol. 28, no. 3, 1989, pages 839-842, XP026616404, cited in the application
  • SHOZO KOBAYASHI: "Beziehung zwischen chemischer Konstitution und scharfen Geschmack bei Säureamiden", Chemisches Zentralblatt, vol. 99, no. I, 1928, pages 1028-1031,
  • PATENT ABSTRACTS OF JAPAN vol. 2000, no. 08, A & JP 2000 129257 A (NIPPON BEET SUGAR MFG CO LTD) 9 May 2000 (2000-05-09)
  • JOSETTE MARTIN TANGUY et al.: "The distribution of hydroxycinnamic acid amides in flowering plants", Phytochemistry, vol. 17, no. 11, 1978, pages 1927-1928,
  • ERIC FREROT et al.: "New Umami Amides: Structure-Taste Relationship Studies of Cinnamic Acid Derived Amides and the Natural Occurrence of an Intense Umami Amide in Zanthoxylum piperitum", J. Agric. Food Chem., vol. 63, 2015, pages 7161-7168,
  • Yoshihara T. et al: "A New Lignan Amide, Grossamide, from Bell Pepper", Agric. Biol. Chem., vol. 45, no. 11, 1981, pages 2593-2598,
  • Definition of Umami by Merriam-Webster
  • Thieme RÖMPP entry "Natrium-L-glutamat" (MSG), March 2006
  


Description

Technical field



[0001] 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.

[0002] The present invention also concerns compositions or articles containing at least one of the aforementioned compounds, as well as compounds of formula (II), as defined in claim 8.

Background and Prior art



[0003] Various cinnamic acid derived amides are known to naturally occur in plants such as 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].

[0004] Since 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. However, 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.

[0005] In New Developments in Umami (Enhancing) Molecules, Winkel et al, Chemistry & Biodiversity, Vol 5 (2008), p1195-1203, a review of known umami modifying compounds is given. However, there is no suggestion of the compounds of the present invention.

[0006] 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.

[0007] 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.

[0008] 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.

[0009] US2006/057268 reports saturated or unsaturated N-alkamide and their use as umami ingredients.

[0010] It would be desirable to provide a flavor or taste enhancing ingredient that has umami or kokumi characteristics. It would be even more desirable to provide a flavor or taste enhancing ingredient that has umami and kokumi characteristics.

Description of the invention



[0011] We have now surprisingly discovered that 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.

[0012] Accordingly, the present invention provides the use of a compound of formula

in the form of any one of its stereoisomers or a mixture thereof, and wherein
n is an integer from 0 to 2;
the dotted line represents a carbon-carbon single or double bond; and
each of R1 to R4, when taken independently from each other, represents a hydrogen atom or represents a R5 or OR5 group, R5 representing a C1 to C5, or even a C1 to C3, alkyl group; and optionally one of the groups R] to R4 represents -OH; and/or
when R1 and R2 are taken together, and/or R3 and R4 are taken together, represent a OCH2O group, provided said groups taken together are adjacent substituents of the phenyl group;
except of





as an ingredient to confer, enhance, improve or modify the kokumi or umami taste of a flavored article.

[0013] For the sake of clarity, by the expression "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).

[0014] For the sake of clarity, by 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.

[0015] 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.

[0016] According to a particular embodiment of the invention, 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 R1 to R4, taken independently from each other, represents a hydrogen atom or represents a R5 or OR5 group, R5 representing a C1 to C5, or even a C1 to C3, alkyl group.

[0017] According to a particular embodiment of the invention, said compound (I) is selected from the group of compounds in which R1 and R2 both represent methoxy groups and n is 1.

[0018] According to any one of the above embodiments of the invention, said dotted line represents a carbon-carbon double bond.

[0019] According to a particular embodiment of the invention, said compound (I) is a compound of formula

in the form of any one of its stereoisomers or a mixture thereof, and wherein each of R3 or R4, taken independently from each other, represents a hydrogen atom or represents a R5 or OR5 group, R5 representing a C1 to C5, or even a C1 to C3 alkyl group.

[0020] According to any one of the above embodiments of the invention, R3 represents a hydrogen atom or represents a R5 or OR5 group, and R4 represents a R5 or OR5 group, R5 representing a C1 to C5, or even a C1 to C3, alkyl group.

[0021] According to any one of the above embodiments of the invention, R3 represents a hydrogen atom or represents a R5 group, and R4 represents a R5 or OR5 group, R5 representing a C1 to C5, or even a C1 to C3, alkyl group.

[0022] According to any one of the above embodiments of the invention, R3 represents a hydrogen atom or represents a R5 group, and R4 represents a R5, R5 representing a C1 to C5, or even a C1 to C3, alkyl group.

[0023] According to any one of the above embodiments of the invention, R5 represents a methyl, ethyl, propyl or iso-propyl group.

[0024] Herein disclosed are compounds of formula (II), wherein
R3 represents a hydrogen atom or represents a C1 to C5, or even a C1-3, alkyl group or a OR6 group, R6 representing a C1 to C5, or even a C2-3, alkyl group; and
R4 represents a C1 to C5, or even a C1-3, alkyl group or a OR6 group, R6 representing a C1 to C5, or even a C1-3, alkyl group.

[0025] According to the invention, said novel compounds are those wherein R3 represents a hydrogen atom or a C1-3, alkyl group and R4 represents a C1-3, alkyl group or OR6 group, R6 representing a C1 to C3 alkyl group.

[0026] According to any one of the above embodiments of the invention, said compound (I) or (II) is a C19-25 compound, or even a C19-22 compound.

[0027] According to any one of the above embodiments of the invention, the nonaromatic carbon-carbon double bond of compound (I) or (II) can be in a configuration Z or E or a mixture thereof. According to any one of the above embodiments of the invention, 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.

[0028] According to a particular aspect of the present invention, 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-dimethoxyphenyl)-N-(4-ethylphenethyl)acrylamide (referenced in the Examples as Amide 10), (E)-3-(3,4-dimethoxyphenyl)-N-(3,4-dimethylphenethyl)acrylamide (referenced in the Examples as Amide 11), (E)-3-(3,4-dimethoxyphenyl)-N-(4-isopropylphenethyl)acrylamide (referenced in the Examples as Amide 12) or (E)-3-(3,4-dimethoxyphenyl)-N-(3-methylphenethyl)acrylamide (referenced in the Examples as Amide 17).

[0029] The compounds of the invention can be used alone or in mixtures and provide a strong kokumi or umami taste at exceptionally low levels.

[0030] As mentioned above, 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.

[0031] According to a particular embodiment of the invention, 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.

[0032] According to a particular embodiment of the invention, 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. Surprisingly, in seafood applications such as surimi, or seafood bouillons or snack flavors, compounds according to formula (I) are also found to enhance the perception of sweetness and longevity of the flavor. By contrast, in beef flavors, 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.

[0033] In other words 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). In the context of the present invention "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.

[0034] In another aspect, the invention provides a taste-modifying composition comprising:
  1. i) as a taste-conferring or modifying ingredient, at least one compound according to formula (II) above;
  2. ii) at least one ingredient selected from the group consisting of a flavor carrier and a flavor base; and
  3. iii) optionally at least one flavor adjuvant.


[0035] By "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.

[0036] 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.

[0037] Suitable solid carriers include, for instance, absorbing gums or polymers, or even encapsulating materials. Examples of such 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- und Gehermittel in Lebensmittel, Band 2 der Schriftenreihe Lebensmittelchemie, Lebensmittelqualität, Behr's VerlagGmbH & Co., Hamburg, 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.

[0038] By "flavor base" we mean here a composition comprising at least one flavoring ingredient.

[0039] Said flavoring ingredient is not a compound of formula (I). Moreover, by "flavoring ingredient" it is meant here a compound, which is used in flavoring preparations or compositions to impart a hedonic effect. In other words such 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.

[0040] The nature and type of the 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. In general terms, 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. Arctander, Perfume and Flavor Chemicals, 1969, Montclair, New Jersey, USA, or its more recent versions, or in other works of a similar nature, as well as in the abundant patent literature in the field of flavor. It is also understood that said co-ingredients may also be compounds known to release in a controlled manner various types of flavoring compounds.

[0041] According to a particular embodiment of the invention, 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. Or ingredients rich in those compounds mentioned before that are well known to the people skilled in the art.

[0042] By "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.

[0043] A composition consisting of at least one compound of formula (II) 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 (II), at least one flavor carrier, at least one flavor base, and optionally at least one flavor adjuvant.

[0044] In a highly preferred embodiment, more than one compound of formula (II) 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.

[0045] Moreover, a compound of formula (II) can be advantageously incorporated into flavored articles to positively impart, or modify, the kokumi or umami taste of said articles. Thus, in yet another aspect, the present invention provides a flavored article comprising:
  1. i) as taste-conferring or modifying ingredient, at least one compound of formula (II), as defined above, optionally present as part of a flavoring composition; and
  2. ii) a foodstuff base.


[0046] 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:
  • a seasonings or condiment, such as a stock, a savory cube, a powder mix, a flavored oil, a sauce (e.g. a relish, barbecue sauce, a dressing, a gravy or a sweet and/or sour sauce), a salad dressing or a mayonnaise;
  • a meat-based product, such as a poultry, beef or pork based product, a seafood, surimi, or a fish sausage;
  • a soup, such as a clear soup, a cream soup, a chicken or beef soup or a tomato or asparagus soup;
  • a carbohydrate-based product, such as instant noodles, rice, pasta, potatoes flakes or fried, noodles, pizza, tortillas, wraps;
  • a dairy or fat product, such as a spread, a cheese, or regular or low fat margarine, a butter/margarine blend, a butter, a peanut butter, a shortening, a processed or flavored cheese;
  • a savory product, such as a snack, a biscuit (e.g. chips or crisps) or an egg product, a potato/tortilla chip, a microwave popcorn, nuts ,a bretzel, a rice cake, a rice cracker, etc;
  • an imitation products, such as a dairy (e.g a reformed cheese made from oils, fats and thickeners) or seafood or meat (e.g. a vegetarian meat replacer, veggie burgers) analogue; or
  • a pet or animal food.


[0047] Particularly preferred foodstuffs in which the compound according to formula (II) finds utility include those having topnotes such as seafood, beef, chicken, vegetables, cheese, fat, tallow and/or marrow are important.

[0048] For the sake of clarity, it has to be mentioned that, by "foodstuff" we mean here an edible product, e.g. a food or a beverage. Therefore, 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.

[0049] The nature and type of the constituents of the foodstuffs or beverages do not warrant a more detailed description here, the skilled person being able to select them on the basis of his general knowledge and according to the nature of said product.

[0050] According to any one of the above embodiments of the invention, 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 R3 represents a hydrogen atom or represents a R5 group, and R4 represents a R5 or OR5 group, R5 representing a C1 to C3 alkyl group. According to any one of the above embodiments of the invention, R5 represents a methyl, ethyl, propyl or iso-propyl group.

[0051] 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.

[0052] In the case of flavoring compositions, typical 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. Concentrations lower than these, such as in the order of 0.5 ppm to 300 ppm by weight, more preferably 5ppm to 75ppm, most preferably 8 to 50 ppm, can be used when these compounds are incorporated into flavored articles, the percentage being relative to the weight of the article.

[0053] At these levels the taste is typically described as umami-like, lasting, sweet and lingering.

Examples



[0054] The invention will now be described in further detail by way of the following example, wherein the abbreviations have the usual meaning in the art, the NMR spectral data were recorded in CDCl3, with a 400 MHz machine for 1H, and a 100 or 125 MHz machine for 13C, the chemical displacements, δ, are indicated in ppm with respect to TMS as standard, and the coupling constants, J, are expressed in Hz.

Example 1


Preparation of Compounds Suitable for Use According to the Invention


Synthesis of amides with ethyl chloroformate, general procedure:



[0055] 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. It was washed with aqueous 5% KHSO4, brine, aqueous 5% NaHCO3, brine, and then dried over Na2SO4 and evaporated under high vacuum for 3 hours. The crude product was purified by flash chromatography (silica gel; cyclohexane/EtOAc, 2:8) or by recrystallization from EtOAc. Yields were between 50 and 80% on the purified product.

Amide 1:



[0056] 

starting amine: 2-(4-methoxyphenyl)ethanamine
1H NMR: 2.82 (t, J = 7.0 , 2H), 3.61 (∼q, J = 7.0, 5.9 , 2H), 3.78 (s, 3H), 3.86 (s, 3H), 3.88 (s, 3H), 5.87 (t, J = 5.9 , 1H), 6.24 (d, J = 15.5 , 1H), 6.81 (d, J = 8.3 , 1H), 6.84 (d, J = 8.6 , 2H), 6.98 (d, J = 2.0, 1H), 7.05 (dd, J = 8.3, 2.0 , 1H), 7.13 (d, J = 8.6 , 2H), 7.55 (d, J = 15.5 , 1H).
13C NMR: 34.8 (t), 41.0 (t), 55.2 (q), 55.8 (q), 55.9 (q), 109.7 (d), 111.1 (d), 114.1 (d), 118.6 (d), 121.9 (d), 127.8 (s), 129.7 (d), 130.9 (s), 140.7 (d), 149.1 (s), 150.5 (s), 158.3 (s), 166.2 (s).

Amide 2:



[0057] 

starting amine: 2-phenylethanamine
1H NMR: 2.89 (t, J = 6.8 , 2H), 3.66 (∼q, J = 6.8, 5.5 , 2H), 3.87 (s, 3H), 3.89 (s, 3H), 5.72 (t, J = 5.5 , 1H), 6.21 (d, J = 15.5 , 1H), 6.83 (d, J = 8.3 , 1H), 6.99 (d, J = 2.0 , 1H), 7.06 (dd, J = 8.3, 2.0 , 1H), 7.20-7.26 (m, 3H), 7.30-7.34 (m, 2H), 7.56. (d, J = 15.5 , 1H).
13C NMR: 35.7 (t), 40.8 (t), 55.9 (q), 55.9 (q), 109.7 (d), 111.1 (d), 118.5 (d), 121.9 (d), 126.5 (d), 127.8 (s), 128.7 (d), 128.8 (d), 139.0 (s), 140.9 (d), 149.1 (s), 150.6 (s), 166.1 (s).

Amide 3: (not according to the invention)



[0058] 

starting amine: 2-(3,4-dimethoxyphenyl)ethanamine
1H NMR: 2.84 (t, J = 6.9 , 2H), 3.63 (∼q, J = 6.9, 6.0 , 2H), 3.86 (s, 6H), 3.87 (s, 3H), 3.89 (s, 3H), 5.79 (t, J = 6.0 , 1H), 6.23 (d, J = 15.5 , 1H), 6.75 (∼d, J = 8.0 , 1H), 6.77 (d, J = 2.0 , 1H), 6.81 (d, J = 8.0 , 1H), 6.83 (d, J = 8.0 , 1H), 6.99 (d, J = 2.0 , 1H), 7.06 (dd, J = 8.3, 2.0 , 1H), 7.56 (d, J = 15.5 , 1H).
13C NMR: 35.2 (t), 40.9 (t), 55.86 (q), 55.88 (q), 55.93 (2 q), 109.6 (d), 111.1 (d), 111.4 (d), 112.0 (d), 118.5 (d), 120.7 (d), 122.0 (d), 127.8 (s), 131.4 (s), 140.9 (d), 147.7 (s), 149.1 (s), 149.1 (s), 150.6 (s), 166.1 (s);

Amide 4:



[0059] 

starting amine: 2-(3-methoxyphenyl)ethanamine
1H NMR: 2.86 (t, J = 6.9 , 2H), 3.65 (∼q, J = 7.0, 5.7 , 2H), 3.79 (s, 3H), 3.87 (s, 3H), 3.89 (s, 3H), 5.76 (t, J = 5.7 , 1H), 6.22 (d, J = 15.5 , 1H), 6.76-6.82 (m, 3H), 6.83 (d, J = 8.4 , 1H), 6.99 (d, J = 2.0 , 1H), 7.05 (dd, J = 8.4, 2.0 , 1H), 7.23 (dt, J = 7.5, 1.0 , 1H), 7.56 (d, J = 15.5, 1H).
13C NMR: 35.7 (t), 40.6 (t), 55.2 (q), 55.8 (q), 55.9 (q), 109.7 (d), 111.1 (d), 111.9 (d), 114.5 (d), 118.6 (d), 121.1 (d), 121.9 (d), 127.8 (s), 129.7 (d), 140.6 (s), 140.8 (d), 149.1 (s), 150.6 (s), 159.8 (s), 166.2 (s).

Amide 5:



[0060] 

starting amine: 2-(2-methoxyphenyl)ethanamine
1H NMR: 2.90 (t, J = 6.8 , 2H), 3.62 (∼q, J = 6.8, 5.6 , 2H), 3.84 (s, 3H), 3.87 (s, 3H), 3.88 (s, 3H), 5.91 (t, J = 5.6 , 1H), 6.22 (d, J = 15.5 , 1H), 6.82 (d, J = 8.3 , 1H), 6.87 (∼dd, J = 8.4, 1.0 , 1H), 6.91 (dd, J = 7.5, 1.0 , 1H), 6.99 (d, J = 1.9 , 1H), 7.05 (dd, J = 8.3, 1.9 , 1H), 7.15 (dd, J = 7.5, 1.8 , 1H), 7.22 (dt, J = 7.5, 1.8 , 1H), 7.53 (d, J = 15.5, 1H).
13C NMR: 30.3 (t), 39.8 (t), 55.3 (q), 55.8 (q), 55.9 (q), 109.7 (d), 110.4 (d), 111.1 (d), 118.9 (d), 120.7 (d), 121.8 (d), 127.4 (s), 127.9 (d), 127.9 (s), 130.6 (d), 140.4 (d), 149.1 (s), 150.5 (s), 157.6 (s), 166.1 (s).

Amide 6:



[0061] 

Starting amine: 2-(3,5-dimethoxyphenyl)ethanamine
1H NMR: 2.82 (t, J = 6.9 , 2H), 3.64 (∼q, J = 6.9, 5.7 , 2H), 3.76 (s, 3H), 3.87 (s, 3H), 3.88 (s, 3H), 5.85 (t, J = 5.7 , 1H), 6.24 (d, J = 15.7 , 1H), 6.34 (t, J = 2.2 , 1H), 6.38 (d, J = 2.2 , 1H), 6.82 (d, J = 8.3 , 1H), 6.99 (d, J = 2.0 , 1H), 7.05 (dd, J = 8.3, 2.0 , 1H), 7.55 (d, J = 15.7 , 1H).
13C NMR: 36.0 (t), 40.5 (t), 55.3 (q), 55.8 (q), 55.9 (q), 98.4 (d), 106.8 (d), 109.7 (d), 111.1 (d), 118.6 (d), 122.0 (d), 127.8 (s), 140.8 (d), 141.3 (s), 149.1 (s), 150.6 (s), 161.0 (s), 166.2 (s).

Amide 7:



[0062] 

starting amine: 2-(3-ethoxyphenyl)ethanamine
1H NMR: 1.40 (t, J = 7.0 , 3H), 2.85 (t, J = 6.9 , 2H), 3.65 (∼q, J = 6.9, 5.6 , 2H), 3.88 (s, 3H), 3.89 (s, 3H), 4.02 (q, J = 7.0, 2H), 5.70 (t, J = 5.6 , 1H), 6.21 (d, J = 15.4 , 1H), 6.76-6.81 (m, 3H), 6.83 (d, J = 8.3 , 1H), 7.00 (d, J = 2.0 , 1H), 7.06 (dd, J = 8.3, 2.0 , 1H), 7.20-7.25 (m, 1H), 7.55 (d, J = 15.4 , 1H).
13C NMR: 14.9 (q), 35.7 (t), 40.6 (t), 55.9 (q), 55.9 (q), 63.4 (t), 109.7 (d), 111.1 (d), 112.4 (d), 115.1 (d), 118.6 (d), 121.0 (d), 122.0 (d), 127.8 (s), 129.7 (d), 140.5 (s), 140.8 (d), 149.1 (s), 150.6 (s), 159.2 (s), 166.1 (s).

Amide 8:



[0063] 

starting amine: 2-(3-propoxyphenyl)ethanamine
1H NMR: 1.01 (t, J = 7.4 , 3H), 1.79 (-hex, J = 7.4, 6.5 , 2H), 2.85 (t, J = 6.9 , 2H), 3.65 (∼q, J = 6.9, 5.7 , 2H), 3.87 (s, 3H), 3.88 (s, 3H), 3.90 (t, J = 6.5 , 2H), 5.70 (t, J = 5.7 , 1H), 6.22 (d, J = 15.5, 1H), 6.76-6.81 (m, 3H), 6.82 (d, J = 8.4, 1H), 6.99 (d, J = 1.9 , 1H), 7.05 (dd, J = 8.4, 2.0 1H), 7.19-7.23 (m, 1H), 7.55 (d, J = 15.4, 1H).
13C NMR: 10.5 (q), 22.6 (t), 35.7 (t), 40.6 (t), 55.8 (q), 55.9 (q), 69.5 (t), 109.7 (d), 111.1 (d), 112.5 (d), 115.1 (d), 118.6 (d), 120.9 (d), 122.0 (d), 127.8 (s), 129.6 (d), 140.5 (s), 140.8 (d), 149.1 (s), 150.6 (s), 159.4 (s), 166.1 (s).

Amide 9:



[0064] 

starting amine: 2-(4-isopropoxyphenyl)ethanamine
1H NMR: 1.32 (d, J = 6.1 , 6H), 2.81 (t, J = 6.9 , 2H), 3.61 (∼q, J = 6.9, 5.8 , 2H), 3.87 (s, 3H), 3.88 (s, 3H), 4.51 (hept, J = 6.1, 1H), 5.80 (t, J = 5.8, 1H), 6.23 (d, J = 15.5 , 1H), 6.81-6.85 (m, 3H), 6.99 (d, J = 2.0 , 1H), 7.05 (dd, J = 8.4, 2.0 , 1H), 7.11 (∼d, J = 8.6 , 2H), 7.55 (d, J = 15.5 , 1H).
13C NMR: 22.1 (q), 34.8 (t), 40.9 (t), 55.8 (q), 55.9 (q), 69.9 (d), 109.7 (d), 111.1 (d), 116.1 (d), 118.6 (d), 121.9 (d), 127.8 (s), 129.7 (d), 130.7 (s), 140.8 (d), 149.1 (s), 150.5 (s), 156.6 (s), 166.1 (s).

Amide 10:



[0065] 

starting amine: 2-(4-ethylphenyl)ethanamine
1H NMR: 1.23 (t, J = 7.6 , 3H), 2.63 (q, J = 7.6 , 2H), 2.85 (t, J = 6.8 , 2H), 3.64 (∼q, J = 6.8, 5.6 , 2H), 3.87 (s, 3H), 3.89 (s, 3H), 5.73 (t, J = 5.6 , 1H), 6.22 (d, J = 15.6 , 1H), 6.81-6.85 (m, 3H), 6.83 (d, J = 8.4 , 1H), 6.99 (d, J = 2.0 , 1H), 7.06 (dd, J = 8.4, 2.0 , 1H), 7.15 (broad s, 4H), 7.55 (d, J = 15.6 , 1H).
13C NMR: 15.6 (q), 28.4 (t), 35.3 (t), 40.8 (t), 55.8 (q), 55.9 (q), 109.7 (d), 111.1 (d), 118.7 (d), 121.9 (d), 127.8 (s), 128.1 (d), 128.7 (d), 136.1 (s), 140.7 (d), 142.4 (s), 149.1 (s), 150.5 (s), 166.1 (s).

Amide 11:



[0066] 

starting amine: 2-(3,4-dimethylphenyl)ethanamine
1H NMR: 2.24 (broad s, 6H), 2.82 (t, J = 7.1 , 2H), 3.63 (∼q, J = 7.1, 5.5, 2H), 3.87 (s, 3H), 3.88 (s, 3H), 5.75 (t, J = 5.5 , 1H), 6.22 (d, J = 15.6 , 1H), 6.82 (d, J = 8.4 , 1H), 6.95 (dd, J = 7.7, 1.8 , 1H), 6.98-7.00 (m, 2H), 7.04-7.08 (m, 2H), 7.55 (d, J = 15.6, 1H).
13C NMR: 19.3 (q), 19.8 (q), 35.2 (t), 40.8 (t), 55.9 (q), 55.9 (q), 109.7 (d), 111.1 (d), 118.6 (d), 121.9 (d), 126.1 (d), 127.9 (s), 129.9 (d), 130.1 (d), 134.7 (s), 136.2 (s), 136.8 (s), 140.7 (d), 149.1 (s), 150.6 (s), 166.1 (s).

Amide 12:



[0067] 

starting amine: 2-(4-isopropylphenyl)ethanamine
1H NMR: 1.25 (t, J = 7.0 , 3H), 2.85 (t, J = 6.9, 2H), 2.89 (hept, J = 7.0 , 1H), 3.65 (∼q, J = 6.9, 5.4 , 2H), 3.88 (s, 3H), 3.89 (s, 3H), 5.71 (t, J = 5.4 , 1H), 6.22 (d, J = 15.6 , 1H), 6.83 (d, J = 8.4 , 1H), 7.00 (d, J = 2.0 , 1H), 7.06 (dd, J = 8.4, 2.0 , 1H), 7.14-7.19 (m, 4H), 7.56 (d, J = 15.6 , 1H).
13C NMR: 24.0 (q), 33.7 (d), 35.3 (t), 40.8 (t), 55.9 (q), 55.9 (q), 109.7 (d), 111.1 (d), 118.6 (d), 121.9 (d), 126.7 (d), 127.9 (s), 128.7 (d), 136.2 (s), 140.8 (d), 147.1 (s), 149.1 (s), 150.6 (s), 166.1 (s).

Amide 13:



[0068] 

starting amine: 2-(3,4-dimethoxyphenyl)ethanamine
starting acid: (E)-3-(benzo[d][1,3]dioxol-5-yl)acrylic acid
1H NMR: 2.83 (t, J = 7.1 , 2H), 3.62 (∼q, J = 7.1, 5.9 , 2H), 3.858 (s, 3H), 3.862 (s, 3H), 5.70 (t, J = 5.9 , 1H), 5.98 (s, 2H), 6.16 (d, J = 15.6 , 1H), 6.74-6.83 (m, 4H), 6.96-6.97 (m, 2H), 7.56 (d, J = 15.6 , 1H).
13C NMR: 35.2 (t), 40.9 (t), 55.9 (q), 55.9 (q), 101.4 (t), 106.3 (d), 108.5 (d), 111.4 (d), 112.0 (d), 118.6 (d), 120.7 (d), 123.8 (d), 129.2 (s), 131.4 (s), 140.8 (d), 147.7 (s), 148.2 (s), 149.0 (s), 149.1 (s), 166.0 (s).

Amide 14:



[0069] 

starting amine: 2-(3,4-dimethoxyphenyl)ethanamine
starting acid: (E)-3-(4-methoxyphenyl)acrylic acid
1H NMR: 2.83 (t, J = 6.9 , 2H), 3.62 (∼q, J = 6.9, 5.7 , 2H), 3.80 (s, 3H), 3.83 (s, 3H), 3.84 (s, 3H), 5.97 (t, J = 5.7 , 1H), 6.25 (d, J = 15.6 , 1H), 6.73-6.81 (m, 3H), 6.84 (d, J = 8.8 , 2H), 7.40 (d, J = 8.8 , 2H), 7.57 (d, J = 15.6 , 1H).
13C NMR: 35.3 (t), 41.0 (t), 55.3 (q), 55.8 (q), 55.9 (q), 111.4 (d), 112.0 (d), 114.2 (d), 118.4 (d), 120.7 (d), 127.5 (s), 129.3 (d), 131.5 (s), 140.5 (d), 147.7 (s), 149.0 (s), 160.8 (s), 166.3 (s).

Amide 15:



[0070] 

starting amine: 2-(3,4-dimethoxyphenyl)ethanamine
starting acid: (E)-3-(4-acetoxy-3-methoxyphenyl)acrylic acid. After the coupling, deprotection step was performed in MeOH/5% aq Na2CO3 (1 : 1).
1H NMR: 2.83 (t, J = 6.9 , 2H), 3.63 (∼q, J = 6.9, 5.7 , 2H), 3.86 (s, 3H), 3.87 (s, 3H), 3.90 (s, 3H), 5.63 (t, J = 5.7 , 1H), 6.17 (d, J = 15.4 , 1H), 6.74 (∼d, J = 1.9 , 1H), 6.76 (∼dd, J = 8.0, 1.9 , 1H), 6.82 (d, J = 8.0 , 1H), 6.89 (d, J = 8.0 , 1H), 6.96 (d, J = 1.9 , 1H), 7.03 (dd, J = 8.2, 1.9 , 1H), 7.52 (d, J = 15.4 , 1H). Exchangeable OH not seen.
13C NMR: 35.2 (t), 40.9 (t), 55.9 (q), 56.0 (q), 109.6 (d), 111.4 (d), 112.0 (d), 114.7 (d), 118.0 (d), 120.7 (d), 122.2 (d), 127.3 (s), 131.4 (s), 141.2 (d), 146.7 (s), 147.4 (s), 147.7 (s), 149.1 (s), 166.3 (s).

Amide 16:



[0071] 

starting amine: (4-methoxyphenyl)methanamine
starting acid: (E)-3-(3,4-dimethoxyphenyl)acrylic acid
1H NMR: 3.79 (s, 3H), 3.87 (s, 3H), 3.89 (s, 3H), 4.49 (d, J = 5.7 , 2H), 5.93 (t, J = 5.7 , 1H), 6.29 (d, J = 15.5 , 1H), 6.83 (d, J = 8.4, 1H), 6.86 (∼d, J = 8.7 , 2H), 7.00 (d, J = 2.0 , 1H), 7.06 (dd, J = 8.4, 2.0, 1H), 7.24 (∼d, J = 8.7 , 2H), 7.59 (d, J = 15.5 , 1H).
13C NMR: 43.3 (t), 55.3 (q), 55.8 (q), 55.9 (q), 109.7 (d), 111.1 (d), 114.1 (d), 118.4 (d), 121.9 (d), 127.8 (s), 129.3 (d), 130.4 (s), 141.1 (d), 149.1 (s), 150.6 (s), 159.1 (s), 165.9 (s).

Amide 17:



[0072] 

starting amine: 2-(3-methylphenyl)ethanamine
starting acid: (E)-3-(3,4-dimethoxyphenyl)acrylic acid
1H NMR: 2.34 (s, 3H), 2.85 (t, J = 7.1 , 2H), 3.65 (∼q, J = 7.1, 5.4 , 2H), 3.88 (s, 3H), 3.89 (s, 3H), 5.67 (t, J = 5.4 , 1H), 6.21 (d, J = 15.5 , 1H), 6.83 (d, J = 8.3 , 1H), 7.00 (d, J = 2.0 , 1H), 7.02-7.07 (m, 4H), 7.21 (∼d, J = 7.5 , 1H), 7.55 (d, J = 15.5 , 1H).
13C NMR: 21.4 (q), 35.6 (t), 40.7 (t), 55.9 (q), 55.9 (q), 109.7 (d), 111.1 (d), 118.6 (d), 121.9 (d), 125.8 (d), 127.3 (d), 127.8 (s), 128.6 (d), 129.6 (d), 138.3 (s), 138.8 (s), 140.8 (d), 149.1 (s), 150.6 (s), 166.1 (s).

Example 2



[0073] Examples marked with an asterisk (*) are comparative examples.

Evaluation of the Umami Effect of the Compound according to the Use of the Invention (in Water)


a) Pure amide in pure water



[0074] The amides were evaluated at 20ppm in mineral water in comparison with 0.05% monosodium glutamate (MSG). The trained panelists (5-10) were giving an umami taste intensity note. The Relative umami intensity (RUI) was calculated as follows:



[0075] The following table gives the average of the notes obtained from all panelists.
Amide N°123*4567
RUI 5.6 3.8 3.3 10.2 3.2 3.7 9.8
               
Amide N°891011121417
RUI 9.9 6.5 11.5 13.3 5.9 3.8 12.1

b) In the presence of maltodextrin and MSG



[0076] Amides 1, 3, 4 and 8 were blended and diluted in maltodextrin at 10% w/w.
Each blend was then added into a water solution containing MSG at 500ppm in order to achieve a concentration ranging between 20 and 100ppm of the amides, as indicated in the tables below:
 Sol 1Sol 2Sol 3Sol 4Sol 5Sol 6Sol 7
MSG 500 500 500 500 500 500 500
Amide 1 - - - - 20 - -
Amide 3* - 20 35 50 - - -
Amide 4 - - - - - 20 -
Amide 8 - - - - - - 20 20
and also:
 Sol 8Sol 9Sol 10Sol 11Sol 12Sol 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


[0077] 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.
 Umami intensity with nose-clipUmami intensity without nose-clipDescription With nose-clip/without nose-clip
Solution 1 0 0 Umami
Solution 2* 0.91 0.76 Umami, mouthfeel, salivating/nutty, woody
Solution 3* 0.46 0.65 Umami, mouthfeel, salty/nutty, woody
Solution 4* 0.95 0.95 Umami, salty, mouthfeel, salivating, astringent, metallic/nutty, earthy
Solution 5 1.13 1.25 Umami, salty, sweet, mouthfeel, fatty
Solution 6 1.72 1.71 Umami, mouthfeel, salty, sweet/nutty
Solution 7 1.25 1.46 Umami salty, mouthfeel, salivating, hot, cooling
Solution 8 1.27 1.34 Umami, sweet, salty, astringent, bitter, mouthfeel
Solution 9 0.98 1.16 Umami, sweet
Solution 10 0.88 0.94 Umami, sweet, salty, pungent, bitter
Solution 11 0.8 0.95 Umami, green, herbal, salivating
Solution 12 0.95 1.13 Umami, salty, sweet, herbal, astringent, metallic
Solution 13 1.57 1.47 Umami, salty, pungent, mouthfeel, herbal

Example 3


Evaluation of the Umami Effect of the Compound according to the Use of the Invention (in Applications)



[0078] Examples marked with an asterisk (*) are comparative examples.

1) Evaluation of amides 1 and 3 in a beef bouillon



[0079] A beef stock was prepared containing the following ingredients:
 Ingredients in % w/w
Maltodextrin 52
Onion Powder 1.5
Salt 32.7
White pepper 0.1
Yeast extract 3.8
Palm Oil 7.6
Caramel Color 0.7
Beef flavor 1.5


[0080] 10g of beef stock was poured in 500ml of boiling water. MSG and amides 1 and 3 were added to the beef bouillon at the dosages indicated in Table 1.
Table 1 : Ingredients in ppm
 Bouillon 1Bouillon 2Bouillon 3Bouillon 4
MSG - 700 - -
Amide 1 - - - 25
Amide 3* - - 50 -


[0081] 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:
Table 2 : Averages for each bouillon and descriptors
 Umami intensityComments
Bouillon 1 2.1 Yeasty, oniony, beef fat, flat
Bouillon 2 5.1 More salty, round, umami, oniony, juicy, fatty
Bouillon 3* 3.1 Mouthfeel, salty, body
Bouillon 4 3.9 Umami, round

2) Evaluation of amide 1 in a chicken bouillon



[0082] A chicken stock was prepared containing the following ingredients:
 Ingredients in % w/w
Chicken meat powder 2.5
Maltodextrin 32.2
Garlic powder 0.5
Palm oil 5
Ground white pepper 0.3
Yeast extract 10
Onion powder 3.25
Toasted onion powder 2
Turmeric 0.25
Salt 35
Chicken fat 5
Chicken flavor 4


[0083] 10g of chicken stock was poured in 500ml of boiling water. MSG and amide 1 were added to the chicken bouillon at the dosages indicated in Table 3.
Table 3 : Ingredients in ppm
 Bouillon 1Bouillon 2Bouillon 3
MSG - 500 -
Amide 1 - - 20


[0084] The bouillons were presented to 5 trained panelists on a blind test basis as described above. The results are reported herein below:
Table 4 : Averages for each bouillon and descriptors
 Umami intensityComments
Bouillon 1 3.5 Flat, salty
Bouillon 2 6.4 Umami, mouthfeel, sweet, pleasant
Bouillon 3 6.3 Umami

3) Evaluation of amides 1 and 4 in a pork flavor



[0085] Amides 1 and 4 were evaluated at 20 ppm by 5 trained panelists in a pork flavor on a blind test basis as described above. The results are reported herein below:
Table 5 : Averages for each bouillon and descriptors
 Umami intensityComments
Pork flavor 4.5 Meaty, pork, animalic, fatty, mouthfeel, balanced, good
Pork flavor + Amide 1 6 More umami, more meaty, pork notes enhanced, liquorice note, slightly cooling, fatty
Pork flavor + Amide 4 7 More umami, rich strong meaty and pork notes, fatty

4) Evaluation of amides 1, 4, 8, 11, 12 in a chicken bouillon containing MSG and ribotides



[0086] A chicken bouillon was prepared containing the following ingredients:
 Ingredients in % w/w
Salt 27
MSG 10
Ribotides 0.03
Sugar 4
Vegetable oil 2
Chicken fat 2
White pepper powder 0.1
Yeast powder 1.5
Soy sauce powder 0.5
Chicken powder 4
Maltodextrin 35.77
Corn starch 5
Wheat powder 3
Egg powder 4
Chicken flavor 1.1


[0087] 1g of chicken bouillon was poured into 100ml of boiling water. Amides 1, 4, 8, 11, 12 were added to the chicken bouillon at the dosages indicated in Table 6:
Table 6 : Ingredients in ppm
 Bouillon
 123456
Amide 1 - 25 - - - -
Amide 4 - - 25 - - -
Amide 8 - - - 8 - -
Amide 11 - - - - 5 -
Amide 12 - - - - - 25


[0088] The bouillons were presented to 5 trained panelists on a blind test basis as described above. The results are reported herein below:
Table 7 : Averages for each bouillon and descriptors
 Umami intensityComments
Bouillon 1 5.3 White meat, round, no off notes
Bouillon 2 6.3 Sweet, meaty, balanced, very round, full
Bouillon 3 6.3 Slow build, mouthfeel, sweet, umami, no off note, round, very balanced
Bouillon 4 6.7 Strong umami, sweet, lingering, sweet and umami
Bouillon 5 6.7 White meat, slightly astringent, very full, round, lasting, no off notes
Bouillon 6 6 Mouthfeel, no off note, umami, sweet, very balanced slightly astringent

5) Evaluation of amides 1 and 3 in marinated chicken



[0089] A marinade was prepared containing the following ingredients:
 Ingredients in % w/w
Water 90
Salt 4
Hamine phosphate 1
Chicken White Meat Flavor 5


[0090] MSG, amides 1 and 3 were added to the marinade at the dosages indicated herein below:
 Ingredients in % w/w
 Marinade 1Marinade 2Marinade 3Marinade 4
Marinade 100 100 100 100
MSG - 0.3 - -
Amide 1 - - 0.05 -
Amide 3* - - - 0.05


[0091] Marinades were added with chicken meat in plastic bags in the following quantities:
 Ingredients in % w/w
 Marinated chicken 1Marinated chicken 2Marinated chicken 3Marinated chicken 4
Chicken meat 90 90 90 90
Marinade 1 10 - - -
Marinade 2 - 10 - -
Marinade 3 - - 10 -
Marinade 4* - - - 10


[0092] 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 marinated chicken samples were presented to 5 trained panelists on a blind test basis as described above. The results are reported herein below:
Table 8 : Averages for each marinated chicken and descriptors
 Umami intensityComments
Marinated chicken 1 1.3 dry
Marinated chicken 2 4 Strong, clean, pleasant aftertaste, juicy
Marinated chicken 3 4.9 Very similar to MSG, meaty, round, brothy, balanced, sweet, full
Marinated chicken 4* 3 Clean, pleasant, strong impact, enhances chicken juicy, sweet

6) Evaluation of amides 1 and 3 in surimi



[0093] Surimi was prepared using the following ingredients in %w/w:
 Ingredients in % w/w
Frozen surimi base 39.8
Salt 1.19
Native Wheat Starch 4.98
Potato Starch 4.98
Sunflower Oil 4.98
Egg White 6.97
Ice 36.6
Crab extract 0.5


[0094] 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.
MSG and the amides 1 and 3 were added to the surimi preparation at the dosages indicated herein below:
 Surimi 1Surimi 2Surimi 3Surimi 4
MSG - 5000ppm - -
Amide 1 - - 50ppm -
Amide 3* - - - 50ppm


[0095] 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.
The surimi samples were presented to 5 trained panelists on a blind test basis as described above. The results are reported herein below:
Table 9 : Averages for each surimi and descriptors
 Umami intensityComments
Surimi 1 2.2 Flat, eggy, slightly amine, not really fishy
Surimi 2 5.3 Sweet, umami, round, sweet, salty
Surimi 3 3.2 Slightly sweet, umami, juicy, round, fishy, crab
Surimi 4* 3.7 Crab, slightly amine, sweet, fishy, oyster, crab, juicy



Claims

1. Use of a compound of formula (I)

in the form of any one of its stereoisomers or a mixture thereof, and wherein
n is an integer from 0 to 2;
the dotted line represents a carbon-carbon single or double bond; and
each of R1 to R4, when taken independently from each other, represents a hydrogen atom or represents a R5 or OR5 group, R5 representing a C1 to C5 alkyl group; and optionally one of the groups R1 to R4 represents -OH; and/or
when R1 and R2 are taken together, and/or R3 and R4 are taken together, represent a OCH2O group, provided said groups taken together are adjacent substituents of the phenyl group;
except of





as an ingredient to confer, enhance, improve or modify the kokumi or umami taste of a flavored article.
 
2. Use according to claim 1, wherein n is 0 or 1;
the dotted line represents carbon-carbon single or double bond; and
each of R1 to R4, taken independently from each other, represents a hydrogen atom, or represents a R5 or OR5 group, R5 representing a C1 to C5 alkyl group.
 
3. Use according to claim 1, wherein said compound (I) is of formula

in the form of any one of its stereoisomers or a mixture thereof, and wherein each of R3 or R4, taken independently from each other, represents a hydrogen atom, or represents a R5 or OR5 group, R5 representing a C1 to C5 alkyl group.
 
4. Use according to any one of claims 1 to 3, wherein R3 represents a hydrogen atom or represents a R5 or OR5 group, and R4 represents a R5 or OR5 group, R5 representing a C1 to C5 alkyl group.
 
5. Use according to any one of claims 1 to 4, wherein R3 represents a hydrogen atom or represents a R5 group, and R4 represents a R5 or OR5 group, R5 representing a C1 to C5 alkyl group.
 
6. Use according to any one of claims 1 to 5, wherein 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.
 
7. Use according to claim 1, wherein said compound (I) is selected amongst (E)-3-(3,4-dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamide, (E)-3-(3,4-dimethoxy-phenyl)-N-(3-methoxyphenethyl)acrylamide, (E)-3-(3,4-dimethoxyphenyl)-N-(3-ethoxy-phenethyl)acrylamide, (E)-3-(3,4-dimethoxyphenyl)-N-(3-propoxyphenethyl)acrylamide, (E)-3-(3,4-dimethoxyphenyl)-N-(4-isopropoxyphenethyl)acrylamide, (E)-3-(3,4-dimethoxyphenyl)-N-(4-ethylphenethyl)acrylamide, (E)-3-(3,4-dimethoxyphenyl)-N-(3,4-dimethylphenethyl)acrylamide, (E)-3-(3,4-dimethoxyphenyl)-N-(4-isopropylphenethyl)acrylamide or (E)-3-(3,4-dimethoxyphenyl)-N-(3-methylphenethyl)acrylamide.
 
8. A compound of formula

wherein R3 represents a hydrogen atom or a C1-3 alkyl group and R4 represents a C1-3 alkyl group or OR6 group, R6 representing a C1 to C3 alkyl group.
 
9. A taste-modifying composition comprising:

i) as taste-conferring or modifying ingredient, at least one compound as defined in claim 8;

ii) at least one ingredient selected from the group consisting of a flavor carrier and a flavor base; and

iii) optionally at least one flavor adjuvant.


 
10. A composition according to claim 9, wherein said flavor base comprises another umami imparting flavor ingredient.
 
11. A flavored article comprising:

i) at least one compound as defined in claim 8 ; and

ii) a foodstuff base.


 
12. A flavored article according to claim 11, characterized in that the foodstuff base is a seasonings or condiment, a meat-based products, a soup, a carbohydrate-based product, a dairy or fat product, a savory product, an imitation product or a pet or animal food.
 
13. A flavored article according to claim 11, characterized in that the foodstuff base is

• a stock, a savory cube, a powder mix, a flavored oil, a sauce, a salad dressing or a mayonnaise;

• a poultry, beef or pork based product, a seafood, surimi, or a fish sausage;

• a clear soup, a cream soup, a chicken or beef soup or a tomato or asparagus soup;

• instant noodles, rice, pasta, potatoes flakes or fried, noodles, pizza, tortillas, wraps;

• a spread, a cheese, or regular or low fat margarine, a butter/margarine blend, a butter, a peanut butter, a shortening, a processed or flavored cheese;

• a snack, a biscuit (e.g. chips or crisps) or an egg product, a potato/tortilla chip, a microwave popcorn, nuts, a bretzel, a rice cake, a rice cracker; or

• a reformed cheese made from oils, fats and thickeners or a vegetarian meat replacer, a vegetarian burger.


 


Ansprüche

1. Verwendung einer Verbindung der Formel (I)

in der Form von einem ihrer Stereoisomere oder einem Gemisch davon, und wobei
n eine ganze Zahl von 0 bis 2 ist;
die gestrichelte Linie eine Kohlenstoff-Kohlenstoff-Einfach- oder -Doppelbindung darstellt; und
jedes von R1 bis R4, wenn unabhängig voneinander genommen, ein Wasserstoffatom darstellt oder eine R5- oder OR5-Gruppe darstellt, wobei R5 eine C1- bis C5-Alkylgruppe darstellt; und wahlweise eine der Gruppen R1 bis R4 -OH darstellt; und/oder
wenn R1 und R2 zusammengenommen sind, und/oder R3 und R4 zusammengenommen sind, sie eine OCH2O-Gruppe darstellen, mit der Maßgabe, dass die zusammengenommenen Gruppen benachbarte Substituenten der Phenylgruppe sind;
ausgenommen von





als ein Bestandteil, um den Kokumi- oder Umami-Geschmack eines aromatisierten Artikels zu übertragen, zu verstärken, zu verbessern oder zu modifizieren.
 
2. Verwendung nach Anspruch 1, wobei n 0 oder 1 ist;
die gestrichelte Linie eine Kohlenstoff-Kohlenstoff-Einfach- oder -Doppelbindung darstellt; und
jedes von R1 bis R4, unabhängig voneinander genommen, ein Wasserstoffatom darstellt oder eine R5- oder OR5-Gruppe darstellt, wobei R5 eine C1- bis C5-Alkylgruppe darstellt.
 
3. Verwendung nach Anspruch 1, wobei die Verbindung (I) die Formel

hat, in der Form von einem ihrer Stereoisomere oder einem Gemisch davon, und wobei jedes von R3 oder R4, unabhängig voneinander genommen, ein Wasserstoffatom darstellt oder eine R5- oder OR5-Gruppe darstellt, wobei R5 eine C1- bis C5-Alkylgruppe darstellt.
 
4. Verwendung nach einem der Ansprüche 1 bis 3, wobei R3 ein Wasserstoffatom darstellt oder eine R5- oder OR5-Gruppe darstellt und R4 eine R5- oder OR5-Gruppe darstellt, wobei R5 eine C1- bis C5-Alkylgruppe darstellt.
 
5. Verwendung nach einem der Ansprüche 1 bis 4, wobei R3 ein Wasserstoffatom darstellt oder eine R5-Gruppe darstellt und R4 eine R5- oder OR5-Gruppe darstellt, wobei R5 eine C1- bis C5-Alkylgruppe darstellt.
 
6. Verwendung nach einem der Ansprüche 1 bis 5, wobei die Verbindung (I) oder (II) in der Form eines Gemisches der E- und Z-Stereoisomere ist, wobei das Gemisch mindestens 50% Gew./Gew. oder mindestens 80% Gew./Gew. des Stereoisomers E umfasst, wobei der Rest im Wesentlichen das Z-Stereoisomer ist.
 
7. Verwendung nach Anspruch 1, wobei die Verbindung (I) ausgewählt ist unter (E)-3-(3,4-Dimethoxyphenyl)-N-(4-methoxyphenethyl)acrylamid, (E)-3-(3,4-Dimethoxyphenyl)-N-(3-methoxyphenethyl)acrylamid, (E)-3-(3,4-Dimethoxyphenyl)-N-(3-ethoxy-phenethyl)acrylamid, (E)-3-(3,4-Dimethoxyphenyl)-N-(3-propoxyphenethyl)acrylamid, (E)-3-(3,4-Dimethoxyphenyl)-N-(4-isopropoxyphenethyl)acrylamid, (E)-3-(3,4-Dimethoxyphenyl)-N-(4-ethylphenethyl)acrylamid, (E)-3-(3,4-Dimethoxyphenyl)-N-(3,4-dimethylphenethyl)acrylamid, (E)-3-(3,4-Dimethoxyphenyl)-N-(4-isopropyl-phenethyl)acrylamid oder (E)-3-(3,4-Dimethoxyphenyl)-N-(3-methylphenethyl)acrylamid.
 
8. Verbindung der Formel

wobei R3 ein Wasserstoffatom oder eine C1-3-Alkylgruppe darstellt und R4 eine C1-3-Alkylgruppe oder OR6-Gruppe darstellt, wobei R6 eine C1- bis C3-Alkylgruppe darstellt.
 
9. Geschmack modifizierende Zusammensetzung, umfassend:

i) als Geschmack übertragenden oder modifizierenden Bestandteil mindestens eine Verbindung wie in Anspruch 8 definiert;

ii) mindestens einen Bestandteil, der ausgewählt ist aus der Gruppe bestehend aus einem Aromaträger und einer Aromabasis; und

iii) wahlweise mindestens einen Aroma-Hilfsstoff.


 
10. Zusammensetzung nach Anspruch 9, wobei die Aromabasis einen weiteren Umami vermittelnden Aromabestandteil umfasst.
 
11. Aromatisierter Artikel, umfassend:

i) mindestens eine Verbindung wie in Anspruch 8 definiert; und

ii) eine Nahrungsmittelbasis.


 
12. Aromatisierter Artikel nach Anspruch 11, dadurch gekennzeichnet, dass die Nahrungsmittelbasis ein Gewürz oder Würzmittel, ein Produkt auf Fleischbasis, eine Suppe, ein Produkt auf Kohlenhydratbasis, ein Molkerei- oder Fettprodukt, ein herzhaftes Produkt, ein Imitationsprodukt oder ein Haustier- oder Tierfutter ist.
 
13. Aromatisierter Artikel nach Anspruch 11, dadurch gekennzeichnet, dass die Nahrungsmittelbasis

• eine Brühe, ein Würzwürfel, eine Pulvermischung, ein aromatisiertes Öl, eine Sauce, ein Salatdressing oder eine Mayonnaise;

• ein auf Geflügel, Rindfleisch oder Schweinefleisch basierendes Produkt, eine Meeresfrucht, Surimi oder eine Fischwurst;

• eine klare Suppe, eine Cremesuppe, eine Hühner- oder Rindfleischsuppe oder eine Tomaten- oder Spargelsuppe;

• Instantnudeln, Reis, Teigwaren, Kartoffelflocken oder Fritten, Nudeln, Pizza, Tortillas, Wraps;

• ein Aufstrich, ein Käse oder reguläre oder fettarme Margarine, ein Butter/Margarine-Gemisch, eine Butter, eine Erdnussbutter, ein Backfett, ein Schmelzkäse oder aromatisierter Käse;

• ein Snack, ein Keks (z.B. Chips oder Crisps) oder ein Eiprodukt, ein Kartoffel-/Tortilla-Chip, ein Mikrowellen-Popcorn, Nüsse, eine Brezel, ein Reiskuchen, ein Reiscracker; oder

• ein reformierter Käse, hergestellt aus Ölen, Fetten und Verdickungsmitteln, oder ein vegetarischer Fleischaustauschstoff, ein vegetarischer Burger ist.


 


Revendications

1. Utilisation d'un composé de la formule (I):

sous la forme de l'un quelconque de ses stéréoisomères ou d'un mélange de ceux-ci, et dans lequel:

n est un nombre entier de 0 à 2;

la ligne en pointillés représente une liaison carbone-carbone simple ou double; et

chacun de R1 à R4, lorsque pris indépendamment l'un de l'autre, représente un atome d'hydrogène ou représente un groupe R5 ou OR5, R5 représentant un groupe alkyle C1 à C5, et optionnellement l'un des groupes R1 à R4 représente -OH; et/ou

lorsque R1 et R2 sont pris ensemble et/ou lorsque R3 et R4 sont pris ensemble, ils représentent un groupe OCH2O, à condition que lesdits groupes pris ensemble soient des substituants adjacents du groupe phényle;

à l'exception de:





en qualité d'ingrédient pour conférer, renforcer, améliorer ou modifier le goût kokumi ou umami d'un article aromatisé.


 
2. Utilisation selon la revendication 1, dans lequel n est 0 ou 1;
la ligne en pointillés représente une liaison carbone-carbone simple ou double; et
chacun de R1 à R4, pris indépendamment l'un de l'autre, représente un atome d'hydrogène ou représente un groupe R5 ou OR5, R5 représentant un groupe alkyle C1 à C5.
 
3. Utilisation selon la revendication 1, où ledit composé (I) est de la formule:

sous la forme de l'un quelconque de ses stéréoisomères ou d'un mélange de ceux-ci, et dans lequel chacun de R3 ou R4, pris indépendamment l'un de l'autre, représente un atome d'hydrogène ou représente un groupe R5 ou OR5, R5 représentant un groupe alkyle C1 à C5.
 
4. Utilisation selon l'une quelconque des revendications 1 à 3, où R3 représente un atome d'hydrogène ou représente un groupe R5 ou OR5, et R4 représente un groupe R5 ou OR5, R5 représentant un groupe alkyle C1 à C5.
 
5. Utilisation selon l'une quelconque des revendications 1 à 4, où R3 représente un atome d'hydrogène ou représente un groupe R5, et R4 représente un groupe R5 ou OR5, R5 représentant un groupe alkyle C1 à C5.
 
6. Utilisation selon l'une quelconque des revendications 1 à 5, où ledit composé (I) ou (II) est sous la forme d'un mélange des stéréoisomères E et Z, ledit mélange comprenant au moins 50 % p/p, ou au moins 80 % p/p, du stéréoisomère E, le reste étant essentiellement le stéréoisomère Z.
 
7. Utilisation selon la revendication 1, où ledit composé (I) est sélectionné parmi: (E)-3-(3,4-diméthoxyphényl)-N-(4-méthoxyphénéthyl)acrylamide, (E)-3-(3,4-diméthoxyphényl)-N-(3-méthoxyphénéthyl)acrylamide, (E)-3-(3,4-diméthoxyphényl)-N-(3-éthoxyphénéthyl)acrylamide, (E)-3-(3,4-diméthoxyphényl)-N-(3-propoxyphénéthyl)acrylamide, (E)-3-(3,4-diméthoxyphényl)-N-(4-isopropoxyphénéthyl)acrylamide, (E)-3-(3,4-diméthoxyphényl)-N-(4-éthylphénéthyl)acrylamide, (E)-3 -(3 ,4-diméthoxyphényl)-N-(3,4-diméthylphénéthyl)acrylamide, (E)-3-(3,4-diméthoxyphényl)-N-(4-isopropylphénéthyl)acrylamide ou (E)-3-(3,4-diméthoxyphényl)-N-(3-méthylphénéthyl)acrylamide.
 
8. Composé de la formule:

dans lequel R3 représente un atome d'hydrogène ou un groupe alkyle C1-3, et R4 représente un groupe alkyle C1-3 ou un groupe OR6, R6 représentant un groupe alkyle C1 à C3.
 
9. Composition modifiant le goût, comprenant:

i) en tant qu'ingrédient conférant un goût ou modifiant le goût, au moins un composé selon la revendication 8;

ii) au moins un ingrédient sélectionné parmi le groupe consistant en un support d'arôme et en une base aromatisante; et

iii) optionnellement au moins un adjuvant aromatisant.


 
10. Composition selon la revendication 9, dans laquelle ladite base aromatisante comprend un autre ingrédient aromatisant donnant l'umami.
 
11. Article aromatisé, comprenant:

i) au moins un composé selon la revendication 8; et

ii) une base de produit alimentaire.


 
12. Article aromatisé selon la revendication 11, caractérisé en ce que la base de produit alimentaire est un assaisonnement ou un condiment, un produit à base de viande, une soupe, un produit à base glucidique, un produit laitier ou de matière grasse, un produit salé, un produit d'imitation ou un aliment pour animaux ou animaux domestiques.
 
13. Article aromatisé selon la revendication 11, caractérisé en ce que la base de produit alimentaire est:

- un bouillon, un cube d'assaisonnement, un mélange en poudre, une huile aromatisée, une sauce, un assaisonnement pour salade ou une mayonnaise;

- un produit à base de volaille, bœuf ou porc, un fruit de mer, du surimi ou une saucisse de poisson;

- un consommé, un velouté, un potage au poulet ou bœuf ou un velouté de tomates ou d'asperges;

- des nouilles instantanées, riz, pâtes, pommes de terre en flocons ou frites, nouilles, pizza, tortillas, galettes;

- un produit à tartiner, un fromage, ou une margarine ordinaire ou à faible teneur en matière grasse, un mélange de beurre/margarine, un beurre, un beurre de cacahuètes, un corps gras (shortening), un fromage traité ou aromatisé;

- un en-cas, une croustille (par ex. chips ou crisps) ou un produit à base d'œuf, une chip de pomme de terre/tortilla, un pop-corn à cuire au micro-ondes, des noix, un bretzel, une galette de riz, un cracker de riz; ou

- un fromage reformé fait avec des huiles, matières grasses et épaississants ou un succédané de viande végétarien, un burger végétarien.


 




REFERENCES CITED IN THE DESCRIPTION



This list of references cited by the applicant is for the reader's convenience only. It does not form part of the European patent document. Even though great care has been taken in compiling the references, errors or omissions cannot be excluded and the EPO disclaims all liability in this regard.

Patent documents cited in the description




Non-patent literature cited in the description