Classifications

• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • 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
  • A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
  • C07D213/40—Acylated substituent nitrogen atom

Definitions

• Umami is a flavour sensation generally associated with Asian cuisine.
• improved umami taste helps make low salt products more palatable.
• Umami flavour has traditionally been achieved by the addition of monosodium glutamate (MSG) to foodstuffs.
• MSG monosodium glutamate
• the presence of MSG in foodstuffs is not universally welcome, and there is an interest in the achievement of umami taste with lower proportions of MSG than is normally the case.
• umami flavour composition comprising flavour ingredients and a umami-enhancing or -providing proportion of a compound of the formula (1).
• a consumable composition having umami flavour, said umami flavour being at least partially provided by the presence therein of a compound of the formula (1).
• the compound of formula (1) (hereinafter referred to as "the Umami Compound”) exists in two isomeric forms, the E-form and the Z-form. Both of these compounds are
• the E-form is Nl -neryl-N2-(2-(pyridin-2-yl)ethyl)oxalamide and the Z-form N 1 -geranyl-N2-(2-(pyridin-2-yl)ethyl)oxalamide.
• the Umami Compound may be prepared by methods well known to the art. One such method involves the preparation of (E)-ethyl-2-(3,7-dimethylocta-2,6-dienylamino-2- oxoacetate
• the Umami Compound not only confers a high degree of umami flavour and at very low dosages, but also that this flavour is of unusual quality, in that it has a clean, non-artificial taste. This is in contrast to many other non-MSG umami flavourants.
• the Umami Compound may be used alone, or it may be mixed with other flavouring ingredients to provide a flavouring composition ready for addition to a consumable composition.
• the flavouring ingredients may include other umami flavourants, including MSG.
• Use of the Umami Compound allows a considerable reduction in MSG levels, and in some cases the complete elimination of MSG.
• R 1 is selected from H, methyl and ethyl
• R is selected from H, OH, fluorine, C1-C4 linear or branched alkyl, i-Ce alkoxy wherein the alkyl group is linear or branched, or comprises or consists of a C3-C5 cycloalkyl moiety
• R 3 is selected from H and methoxy
• R 2 and R 3 together form a bridging moiety -O-CH2-O- between the phenyl carbon atoms to which they are connected;
• R 4 is selected from OH and methoxy
• R 5 and R 6 are independently selected from H and methyl
• R 1 , R 2 , R 3 , R 4 , R 5 and R 6 being selected such that,
• R 2 is selected from H, OH, fluorine, methyl, Ci-C 6 alkoxy wherein the alkyl group is linear or branched, or comprises or consists of a C3-C5 cycloalkyl moiety.
• R 2 is selected from methyl, methoxy and isobutyloxy
• R 3 is H
• R 4 is OH
• R 5 and R 6 are H.
• Such compounds are described in UK patent application No. 0913804. Particular non- limiting examples of such compounds include:
• umami flavour-conferring and -enhancing compounds that may be used with the Umami Compound include those described in EP 1642886, WO 5 2005/015158, EP 1312268, WO 2003/088768, EP 1291342 and WO 2006/003107.
• the proportion of the Umami Compound used will depend on the nature of the use and the effect desired. For example, the proportion needed for a partial replacement of MSG will naturally be lower than that of a complete MSG replacement.
• the proportion may vary0 between wide limits, typically between 0.1 ppm and 10 ppm by weight of a consumable composition, more particularly between 0.5 ppm and 5 ppm. However, these are general indications only of useful proportions, and the skilled flavourist may use proportions outside these ranges for particular effects.
• 5 By “consumable composition” is meant any composition that is taken into the mouth for ultimate spitting out or ingestion.
• the composition may be in any physical form, solid, liquid or gaseous.
• Non-limiting examples include all food products, food additives, nutraceuticals, pharmaceuticals and any product placed in the mouth including (but not limited to) chewing gum, oral care products, and oral hygiene products including but not0 limited to, cereal products, rice products, tapioca products, sago products, baker's products, biscuit products, pastry products, bread products, confectionery products, dessert products, gums, chewing gums, flavor or flavor-coated food/beverage containers, yeast products, baking-powder, salt and spice products, snack foods, savoury products, mustard products, vinegar products, sauces (condiments), soups, seasonings, ready-to -eat meals, gravies, nuts5 & nut products, , processed foods, vegetable products, meat and meat products, egg products, milk and dairy products, yoghurts, cheese products, butter and butter substitute products, milk substitute products, soy products, edible oils and fat products, , beverages, carbonated beverages, alcoholic drinks such as beers, wines and spirits, non-alcoholic drinks such as soft
• Step 1 preparation of (E)-ethyl-2-(3,7-dimethylocta-2,6-dienylamino-2-oxoacetate
• Geranylamine (5 g, 32.6 mmol) was added dropwise to diethyl oxalate (15 g, 103 mmol) to give a colorless solution.
• the solution was heated to 120C and stirred at this temperature for 2 hours; the formed ethanol was distilled off during the reaction. The excess of diethyl oxalate was removed by vacuum distillation until 160°C/ lmbar. 8.1g (93% yield) of brownish residual oil was obtained.
• the product is ca. 95% pure according to NMR analysis
• Step 2 preparation of Nl-geranyl-N2-(2-(pyridin-2-yl)ethyl)oxalamide
• the samples were tasted by a professional panel composed of 2 women and 3 men aged between 30 and 60.
• the panel agreed that both solutions tasted umami. They also agreed that solution B was slightly stronger umami, had more succulence and sweetness and had more lingering savoury notes.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Polymers & Plastics (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Food Science & Technology (AREA)
• Health & Medical Sciences (AREA)
• Nutrition Science (AREA)
• Seasonings (AREA)
• Pyridine Compounds (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Coloring Foods And Improving Nutritive Qualities (AREA)

Priority Applications (6)

Applications Claiming Priority (2)

Publications (1)

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Cited By (2)

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Citations (9)

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• 2010
  • 2010-02-04 GB GBGB1001796.0A patent/GB201001796D0/en not_active Ceased
• 2011
  • 2011-02-03 BR BR112012019663-4A patent/BR112012019663B1/pt not_active IP Right Cessation
  • 2011-02-03 SG SG2012051876A patent/SG182515A1/en unknown
  • 2011-02-03 JP JP2012551614A patent/JP5805108B2/ja not_active Expired - Fee Related
  • 2011-02-03 CN CN201180008196.3A patent/CN102741231B/zh not_active Expired - Fee Related
  • 2011-02-03 EP EP11701682.4A patent/EP2531489B1/en not_active Not-in-force
  • 2011-02-03 US US13/576,572 patent/US8470384B2/en not_active Expired - Fee Related
  • 2011-02-03 WO PCT/EP2011/051528 patent/WO2011095533A1/en not_active Ceased

Patent Citations (10)

Non-Patent Citations (1)

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