WO2006046853A1 - Substances de modulation de saveur - Google Patents

Substances de modulation de saveur Download PDF

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Publication number
WO2006046853A1
WO2006046853A1 PCT/NL2005/000719 NL2005000719W WO2006046853A1 WO 2006046853 A1 WO2006046853 A1 WO 2006046853A1 NL 2005000719 W NL2005000719 W NL 2005000719W WO 2006046853 A1 WO2006046853 A1 WO 2006046853A1
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WO
WIPO (PCT)
Prior art keywords
flavour
alkyl
hydroxyl
alkenyl
acyl
Prior art date
Application number
PCT/NL2005/000719
Other languages
English (en)
Inventor
Chris Winkel
Harry Renes
Original Assignee
Quest International Services B.V.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from PCT/NL2005/000258 external-priority patent/WO2005096844A1/fr
Application filed by Quest International Services B.V. filed Critical Quest International Services B.V.
Priority to AU2005300173A priority Critical patent/AU2005300173B2/en
Priority to RU2007119775/15A priority patent/RU2007119775A/ru
Priority to US11/718,288 priority patent/US7897190B2/en
Priority to MX2007005011A priority patent/MX2007005011A/es
Priority to JP2007538840A priority patent/JP5072598B2/ja
Priority to BRPI0518075A priority patent/BRPI0518075B8/pt
Priority to EP05791871.6A priority patent/EP1806977B1/fr
Publication of WO2006046853A1 publication Critical patent/WO2006046853A1/fr

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Classifications

    • 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
    • A23L17/00—Food-from-the-sea products; Fish products; Fish meal; Fish-egg substitutes; Preparation or treatment thereof
    • A23L17/10—Fish meal or powder; Granules, agglomerates or flakes
    • 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

Definitions

  • the present invention concerns novel flavour modulating substances that may advantageously be applied in foodstuffs, beverages and pharmaceutics.
  • the flavour modulating substances according to the invention are capable of modulating the impact of flavour imparting substances.
  • the present invention also provides flavour compositions that can be used to confer a fuller and richer taste and/or aroma to foodstuffs, beverages and pharmaceutics.
  • the present invention also encompasses the use of the aforementioned flavour modulating substances for improving the flavour of foodstuffs, beverages and pharmaceutics, as well as to foodstuffs, beverages and pharmaceutics containing these substances.
  • the flavour of foodstuffs and beverages consists of two parts: the aroma and the taste, hi general what is perceived through the olfactory epithelium in the nasal cavity is referred to as 'aroma', whereas the term 'taste' is generally used to describe the sensory impact that is perceived via the mouth, especially the tongue.
  • the sense of taste provides the final analysis of food prior to ingestion thereof.
  • Visual and olfactory signals already give a first indication but only after intake of the food into the mouth the final decision is made either to ingest or to reject the food.
  • Sweet taste is usually a signal that the food is safe (nice) leading to ingestion of the food.
  • the 'reactions' to salt and umami are really dependent on the strength of the signal.
  • Bitter and sour are usually repulsive taste sensations, leading to rejection.
  • Temperature is another measure by which the food is judged just as well as aching sensations like capsaicin (hot pepper) and certain chemicals (like carbon dioxide).
  • Chlorogenic acids are claimed to enhance sweetness and to reduce bitterness (WO02100192).
  • bitterness is an essential aspect of some food flavours, among which chocolate taste.
  • Purine alkaloids like theombromine and caffeine, as well as amino acids and peptides have been known for a long time as bitter compounds, hi British patent no. GB 1420909 it is disclosed that the bitter flavour of cocoa can be reproduced using a combination of a purine alkaloid and an amino acid or an oligopeptide which 'produces a surpringly more natural simultaneously bitter and astringent flavour note than either of these types of substances alone'.
  • Menthol an important constituent of peppermint oil, has a strong impact on flavoured products not only because of its mint smell but also because it imparts a cooling, fresh taste.
  • menthol in other type of flavour to impart a cool taste has been suggested.
  • US patent application no. US 2005/013846 discloses how menthol and derivatives thereof can be used as flavouring in water continuous spreadable acidified food products to obtain table spreads exhibiting a fresh, cool taste impression.
  • cinnamic aldehyde and eugenol constituents of cinnamon oil
  • flavouring composition for confectionary products, not only for their smell but also because they impart a warm and piquant-tingling taste.
  • the oral pungency of cinnamic aldehyde was described as burning and tingling by Cliff M and Heymann H [ Journal of
  • Cinnamon oil has been proposed as a taste improving flavouring.
  • International patent application no. WO 90/06689 discloses that cinnamon oil, among other spice extracts, added to a minty flavour formulation, can be used to improve the long-lasting flavour of chewing-gum.
  • the aim of the present invention is to provide new 'flavour modulating substances' that provide a positive contribution to the overall flavour impression of foodstuffs, beverages, and/or pharmaceutics they are incorporated in.
  • flavour modulating substances represented by the following formula (I) and/or edible salts thereof can be used advantageously for modulating the flavour of foodstuffs, beverages and pharmaceutics:
  • flavour improving substances according to the present invention can be applied advantageously to impart desirable flavour, especially taste, attributes to the aforementioned products.
  • the present flavour improving substances are capable of modifying the taste and/or aroma impact of other flavour ingredients contained within these same products, thereby improving the overall flavour quality of these products.
  • a substance according to formula (I) wherein Y represents dimethyl-substituted methylene, X represents phenyl, R 1 represents C 4 alkyl R 2 and R 4 represent hydrogen and R 3 represents methyl has been described previously in US patent no. 4,274,862, which document relates to herbicidal compositions and methods for controlling weeds. US 4,274,862 does not in any way mention or refer to flavour characteristics of the substances disclosed therein.
  • the present invention relates to flavour modulating substances according to formula (I) and/or edible salts thereof, as well as to flavour compositions, foodstuffs, beverages and pharmaceutics, comprising one or more substances according to formula (I) and/or edible salts thereof.
  • aspects of the present invention relate to the use of the substances according to formula (I) and/or edible salts thereof for modulating, especially enhancing, the flavour of foodstuffs, beverages and pharmaceutics, and to a process for modulating the flavour of the latter products.
  • the present invention in a first aspect relates to a flavour composition
  • a flavour composition comprising at least 0.1 wt.% of one or more flavouring substances and between 0.001 and 80 wt.% of one or more flavour modulating substances according to formula (I) and/or edible salts thereof:
  • R'-CR ⁇ OR ⁇ -CO-NR ⁇ Y-X (I) wherein: Y represents a covalent bond, Cj-C 5 alkylene or C 2 -C 5 alkenyl, each optionally substituted with 1-5 substituents selected from hydroxyl, C 1 -C 3 alkoxyl and CpC 3 acyl;
  • X represents phenyl, substituted with one or more substituents selected from hydroxyl and
  • R 1 represents hydrogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl or C 3 -C 8 cycloalkenyl, each optionally substituted with 1-8 substituents selected from hydroxyl, oxo, C 1 -C 3 alkyl, C 1 -C 3 alkoxyl, C 1 -C 3 acyl, C2-C 3 alkenyl and C 1 -C 3 carboxyl;
  • R 2 represents hydrogen; C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 8 cycloalkyl, or C 3 -C 8 cycloalkenyl, each optionally substituted with 1-8 substituents selected from hydroxyl, C 1 -C 3 alkyl, C 2 -C 3 alkenyl and C 1
  • R 3 represents hydrogen; or Ci-C 3 acyl or C 1 -C 3 alkyl, each optionally substituted with 1-3 hydroxyl groups ;
  • R 4 represents hydrogen; C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 1 -C 3 acyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkenyl or C 1 -C 6 acyl, each optionally substituted with 1-6 substituents selected from hydroxyl, Ci-C 3 alkyl and C 2 -C 3 alkenyl.
  • the present inventors have found that the above-mentioned substances are very useful ingredients which, particularly in the presence of other flavour imparting substances, are capable of imparting highly appreciated taste sensations to the products in which they are incorporated, specifically a quite remarkable "roundness", “fullness”, “substance”, “fermented fish character” and/or “continuity”. Because of this, the present flavour modulating substances can be employed to improve the taste (including "mouthfeel") of foodstuffs, beverages and pharmaceutics. In addition, it has been found that the flavour modulating substances according to the invention are capable of complementing and modifying the sensory impact of other, flavour imparting, substances contained in the aforementioned products.
  • flavour modulating refers to the capability of a composition or substance to alter the taste and/or aroma impact of other, flavour imparting, substances present within the same product, with the proviso that this change in taste and/or aroma impact is not caused by a flavour contribution of said substance per se, but instead that it mainly results from the combined effect of on the one hand the flavour modulating substance and on the other hand the other flavour imparting substances.
  • the present substances combine the capability of modifying the taste of other flavour substances and a taste contribution of their own. The favourable impact of the present flavour modulating substances is believed to be the result of the combination of these two effects.
  • flavour modulating substances according to the invention are not particularly volatile, they do not produce a strong aroma impact, even though they do affect the aroma impact of other flavour imparting substances.
  • aroma refers to the aspect of flavour that is perceived through the olfactory epithelium. Because of the low volatility of the present flavour modulating substances it is believed that the advantageous properties of these substances are somehow associated with the impact that these substances have on the sensory receptors located within the mouth.
  • a particularly preferred embodiment of the present invention related to flavour modulating substances according to formula (I) wherein Y represents a covalent bond or a linear C 1 -C 5 alkylene or C 2 -C 5 alkenyl, each optionally susbtituted with 1-5 substituents selected from hydroxyl, Ci-C 3 alkoxyl and C 1 -C 3 acyl; It was found that particularly satisfying results can be obtained with flavour modulating substances according to formula (I) wherein Y represents a Cj-C 3 alkylene or alkenyl, each optionally substituted with 1-3 substituents selected from hydroxyl and C 1 - C 2 alkyl. More preferably, Y represents ethylene or methylene, optionally substituted with hydroxyl and/or methyl.
  • Y represents ethylene or methylene.
  • X represents hydroxyphenyl, optionally further substituted with lor 2 substituents selected from hydroxyl or methoxyl.
  • X represents hydroxyphenyl, most preferably 4-hydroxyphenyl; dihydroxyphenyl, preferably 3,4-dihydroxyphenyl; trihydroxyphenyl, preferably 3,4,5- trihydroxyphenyl; or hydroxy-methoxyphenyl, preferably 4-hydroxy-3-methoxyphenyl.
  • R 1 represents C 2 -C 6 alkyl or C 4 -C 6 cycloalkyl, wherein each carbon atom is substituted with a substituted independently selected from hydroxyl, oxo, carboxyl, Ci-C 3 alkoxyl and Ci-C 3 acyl. Even more preferably, R 1 represents C 2 -C 6 alkyl, wherein each carbon atom is substituted with a single hydroxyl group. Most preferably, R 1 represents C 3 -C 5 alkyl, wherein each carbon atom is substituted with a single hydroxyl group.
  • R'-CR 2 (OR 3 )-CO- preferably represents the residue of an aldonic acid, more preferably a C 5 or C 6 aldonic acid.
  • R 1 represents C 1 -C 4 alkyl, more preferably C 1 -C 2 alkyl, most preferably methyl.
  • R 2 preferably represents hydrogen or C 1 -C 4 alkyl, most preferably hydrogen.
  • R 3 preferably represents hydrogen or C 1 -C 3 alkyl, most preferably it represents hydrogen.
  • R 4 preferably represents hydrogen.
  • the present flavour modulating substances are selected from the group consisting of N-lactoyl tyramine, N-gluconyl-tyramine, N- lactoyl 4-hydroxybenzylamine, N-lactoyl vanillylamine, N-lactoyl-dopamine, edible salts thereof and mixtures thereof.
  • the flavour modulating substance is N- lactoyl tyramine.
  • the aforementioned flavour composition comprises at least 0.1 wt% of flavouring substances and one or more of the flavour modulating substances in an amount of at least at least 0.01 wt.%.
  • the flavour composition contains at least 0.1 wt.% of the present flavour modulating substances.
  • the amount of the present flavour modulating substances does not exceed 80 wt%, more preferably it does not exceed 40 wt.%.
  • flavouring substance refers to any substance that is capable of imparting a detectable flavour impact, especially at a concentration below 0.1 wt.%, more preferably below 0.01 wt.%.
  • the flavour composition according to the invention comprises a flavouring substance in an amount of at least 0.5 wt.%, preferably at least 1 wt.%, based on the total weight of the composition.
  • the flavour modulating substances and flavouring substances as defined herein before are employed in a weight ratio within the range of 10:1 to 1:100, preferably in a weight ratio of 5:1 to 1 :50.
  • the flavour composition according to the present invention may suitably be prepared in the form of a liquid, a paste or a powder. In a particularly preferred embodiment the flavour composition is a free flowing powder.
  • flavour compositions according to the present invention include flavourings like fish flavourings, fish sauce flavourings, shrimp flavourings and fermented soy flavourings.
  • Another aspect of the present invention relates to a product selected from the group consisting of foodstuffs, beverages and pharmaceutics, said product comprising at least 0.1 ppm, more preferably at least 1 ppm, most preferably at least 3 ppm of one or more flavour modulating substances according to formula (I) and/or edible salts thereof.
  • the aforementioned products will contain the flavour modulating substances in a concentration of not more than 1000 ppm, preferably of not more than 500 ppm.
  • Typical examples of foodstuffs according to the present invention include soups, sauces, stocks, bouillons, cheese products, dressings, seasonings, margarines, shortenings, bread, pastry, noodles, dairy products and beverages.
  • the present invention relates to a process of modulating, especially improving, the flavour of a foodstuff, a beverage or a pharmaceutical product, comprising incorporating into said foodstuff beverage or pharmaceutical product one or more flavour modulating substances according to formula (I) and/or edible salts thereof, in an amount of at least 0.1 ppm, preferably of at lest 1 ppm, most preferably at least 3 ppm.
  • the present invention relates to flavour modulating substances according to formula (I) and/or edible salts thereof wherein Y represents a covalent bond, a linear Cj-C 5 alkylene or C 2 -C 5 alkenyl, each optionally susbtituted with 1-5 substituents selected from hydroxyl, C 1 -C 3 alkoxyl and C 1 -C 3 acyl and wherein X, Rl, R2, R3 and R4 have the same meaning as defined herein before.
  • a preferred embodiment relates to flavour modulating substances according to formula (I) and/or edible salts thereof wherein Y represents ethylene or methylene and to compositions comprising them in the aforementioned amounts.
  • flavour modulating substances according to formula (I) are suitably produced by reacting a primary or secondary amine with an ⁇ -hydroxyl carboxylate.
  • a process of producing a flavour modulating substance according to formula (I) comprising the step of reacting a substance according to formula (II) with an ce-hydroxyl carboxylate or an ⁇ -hydroxyl carboxylate derivative according to formula (III) or a salt of said carboxylate or derivative.
  • the invention also encompasses reacting a substance according to formula (II) with a lactone that is formed by internal esterification of a substance according to formula (III) wherein R 1 and/or R 2 contain a hydroxyl group;
  • the present invention in another embodiment, encompasses flavour modulating compositions obtainable by the processes described above, flavouring compositions comprising these and the use thereof for improving the flavour of foodstuffs, beverages or pharmaceutics.
  • a process for producing so-called 'process flavours' comprising heating a combination of a carbohydrate source and a nitrogen source in a continuous liquid phase containing at least 10 wt% of an ⁇ -hydroxycarboxylic acid component selected from the group of a- hydroxycarboxylic acids according to formula (III), salts thereof and derivatives thereof, wherein said combination of a carbohydrate source and a nitrogen source additionally comprises one or more substances according to formula (II) and/or salts thereof.
  • the carbohydrate source comprises glucose or xylose
  • the nitrogen source comprises amino acids, hydrolysed proteins or yeast extracts
  • the substance according to formula (III) is selected from lactic acid
  • the substance according to formula (II) is selected from tyramine, dopamine, 4-hydroxybenzylamine, vanillylamine and salts thereof, most preferably tyramine.
  • Process flavours obtained by said process will typically comprise one or more of the present flavour modulating substances.
  • another aspect of the invention relates to process flavours comprising 0.0001 - 0.01 wt%, preferably 0.0001 — 0.001 wt% of one or more substances according to formula I.
  • the nitrogen source is provided by yeast extracts.
  • Example 1 Lactic acid (9 g) and tyramine (3 g ) were mixed and heated for 4 hrs at 120 0 C. The reaction mixture was cooled and washed with ethyl acetate. The residue (7 g) was dissolved in 25 g of water. NMR showed that at least 20 % of the reaction mixture was N- lactoyl-tyramine.
  • Solutions 1) and 4) were described as having a clean mouthfeel, body and thickness.
  • Solution 2) and 5) were described as having a longlasting effect, a clean mouthfeel, body and thickness and as bouillon-like.
  • Nam PIa is a Thai fish sauce produced from a mixture of fish (anchovy), salt and sugar that is fermented for more than 6 months at 30-35 0 C. Protein hydrolysate and lipid oxidation products are formed through microbiological and enzymatic breakdown of the fish.
  • sample 2 When sample 2 was compared with sample 1, it had more body and mouthfeel, a stronger sweet taste impression and a more longlasting effect.
  • sample 4 When sample 4 was compared with sample 3, it had more body and mouthfeel, a stronger sweet taste impression and a more longlasting effect.
  • sample 4 When sample 4 was compared with sample 3, it also had a more rounded, natural fermented fish character and was perceived as a higher quality Nam PIa.
  • sample 5 When sample 5 was compared with sample 1 , it had more body and mouthfeel, a stronger sweet taste impression and a more longlasting effect.
  • sample 6 When sample 6 was compared with sample 3, it had more body and mouthfeel, a stronger sweet taste impression and a more longlasting effect.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Zoology (AREA)
  • Seasonings (AREA)
  • Seeds, Soups, And Other Foods (AREA)

Abstract

L'invention, dans un premier aspect, concerne de nouvelles substances de modulation de saveur selon la formule (I) et/ou des sels comestibles de celles-ci: R1-CR2(OR3)-CO-NR4-Y-X (I). Les substances de formule (I) s'avèrent être avantageusement utilisées pour conférer une saveur souhaitable, en particulier des attributs d'arômes, à des aliments, des boissons, des produits pharmaceutiques, des produits de tabagisme et des produits d'hygiène buccale auxquels ils sont incorporés. En outre, lesdites substances peuvent moduler et être complémentaires à l'influence sensorielle d'autres substances porteuses d'arôme. Ainsi, les substances de modulation de saveur de l'invention s'appliquent avantageusement à des compositions d'arôme, d'aliments, de boissons, de produits pharmaceutiques et de produits d'hygiène buccale. Des exemples typiques de substances de modulation de saveur selon l'invention comprennent: N-lactoyl tyramine, N-gluconyl tyramine, N-lactoyl 4-hydroxybenzylamine, N-lactoyl vanillylamine et N-lactoyl-dopamine.
PCT/NL2005/000719 2004-10-29 2005-10-06 Substances de modulation de saveur WO2006046853A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU2005300173A AU2005300173B2 (en) 2004-10-29 2005-10-06 Flavour modulating substances
RU2007119775/15A RU2007119775A (ru) 2004-10-29 2005-10-06 Вещества, изменяющие вкус и/или аромат
US11/718,288 US7897190B2 (en) 2004-10-29 2005-10-06 Flavour modulating substances
MX2007005011A MX2007005011A (es) 2004-10-29 2005-10-06 Sustancias moduladoras de sabor.
JP2007538840A JP5072598B2 (ja) 2004-10-29 2005-10-06 風味改良物質
BRPI0518075A BRPI0518075B8 (pt) 2004-10-29 2005-10-06 composição flavorizante, produto, e, processo de melhorar o flavor de um alimento, de uma bebida ou de um produto farmacêutico
EP05791871.6A EP1806977B1 (fr) 2004-10-29 2005-10-06 Substances de modulation de saveur

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP04077980 2004-10-29
EP04077980.3 2004-10-29
NLPCT/NL2005/000258 2005-04-06
PCT/NL2005/000258 WO2005096844A1 (fr) 2004-04-06 2005-04-06 Procede de production de preparations possedant une saveur issue de la reaction de maillard

Publications (1)

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WO2006046853A1 true WO2006046853A1 (fr) 2006-05-04

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PCT/NL2005/000719 WO2006046853A1 (fr) 2004-10-29 2005-10-06 Substances de modulation de saveur

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EP (1) EP1806977B1 (fr)
AU (1) AU2005300173B2 (fr)
RU (1) RU2007119775A (fr)
WO (1) WO2006046853A1 (fr)

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012072701A1 (fr) 2010-11-30 2012-06-07 Givaudan Sa Composés organiques
EP2629609A2 (fr) * 2010-10-19 2013-08-28 Elcelyx Therapeutics, Inc. Thérapies basées sur un ligand de récepteur chimiosensoriel
WO2013149019A1 (fr) 2012-03-30 2013-10-03 Givaudan S.A. Dérivés n-acylés de méthionine comme composés d'arôme alimentaire
WO2013149008A2 (fr) 2012-03-30 2013-10-03 Givaudan, S.A. Améliorations apportées à des composés organiques ou se rapportant à ceux-ci
WO2013149012A1 (fr) 2012-03-30 2013-10-03 Givaudan S.A. Dérivés d'acide n-acyl aminé comme composés d'arôme alimentaire
WO2013149025A1 (fr) 2012-03-30 2013-10-03 Givaudan, S., A. Dérivés de n-acyl sérine comme composés d'arôme alimentaire
WO2013149035A2 (fr) 2012-03-30 2013-10-03 Givaudan S.A. Améliorations apportées à des composés organiques ou se rapportant à ceux-ci
WO2013149022A1 (fr) 2012-03-30 2013-10-03 Givaudan S.A. Dérivés de n-acyl proline comme composés d'arôme alimentaire
WO2013148991A1 (fr) 2012-03-30 2013-10-03 Givaudan S.A. Dérivés n-acylés d'acide gamma amino-butyrique et de bêta alanine comme composés d'arôme alimentaire
WO2013148997A1 (fr) 2012-03-30 2013-10-03 Givaudan, S.A. Acides 1-aminocycloalkyl carboxyliques n-acylés comme composés d'arôme alimentaire
WO2013149031A2 (fr) 2012-03-30 2013-10-03 Givaudan S.A. Composition d'arôme en poudre
WO2013148965A2 (fr) 2012-03-30 2013-10-03 Givaudan S.A. Améliorations apportées à des composés organiques ou se rapportant à ceux-ci
WO2015050536A1 (fr) 2013-10-02 2015-04-09 Givaudan S.A. Composés d'acides 2-amino-isobutyriques n-acylés et compositions aromatisantes les contenant
US10385015B2 (en) 2015-09-30 2019-08-20 Givaudan S.A. N-acylated methionine sulfoxides as food flavouring compounds
US10537127B2 (en) 2013-10-02 2020-01-21 Givaudan S.A. Organic compounds
US10674755B2 (en) 2013-10-02 2020-06-09 Givaudan S.A. Organic Compounds
US10834951B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10834943B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds having taste-modifying properties
US10834950B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10975018B2 (en) 2013-10-02 2021-04-13 Givaudan Sa Organic compounds
EP4233565A2 (fr) 2015-09-15 2023-08-30 Givaudan SA Composition d'assaisonnement, en-cas comprenant ladite composition et procédé d'assaisonnement d'un en-cas
US11834393B2 (en) 2013-10-02 2023-12-05 Givaudan Sa Organic compounds having taste-modifying properties

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US3909462A (en) * 1971-09-06 1975-09-30 Givaudan Corp Novel odorant and/or flavorant
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US6287620B1 (en) * 1994-10-07 2001-09-11 Firmenich Sa Flavor enhancing methods

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1329272A (en) * 1919-10-09 1920-01-27 Elnathan K Nelson Vanillyl amin, vanillyl acyl amid, and production thereof
GB814570A (en) * 1956-03-22 1959-06-10 Us Vitamin Corp d-ª‡-methylphenethylamides and pharmaceutical preparations containing such amides
US3909462A (en) * 1971-09-06 1975-09-30 Givaudan Corp Novel odorant and/or flavorant
US4274862A (en) * 1978-11-13 1981-06-23 Sumitomo Chemical Company, Limited N-Dimethylbenzylacetamide derivatives, and their production and use
US6287620B1 (en) * 1994-10-07 2001-09-11 Firmenich Sa Flavor enhancing methods
WO1997004667A1 (fr) * 1995-07-26 1997-02-13 Firmenich S.A. Produits aromatises et procede pour leur preparation

Cited By (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2629609A4 (fr) * 2010-10-19 2014-08-27 Elcelyx Therapeutics Inc Thérapies basées sur un ligand de récepteur chimiosensoriel
EP2629609A2 (fr) * 2010-10-19 2013-08-28 Elcelyx Therapeutics, Inc. Thérapies basées sur un ligand de récepteur chimiosensoriel
WO2012072701A1 (fr) 2010-11-30 2012-06-07 Givaudan Sa Composés organiques
US9596874B2 (en) 2010-11-30 2017-03-21 Givaudan S.A. Bitter taste masking compositions and method of masking bitter taste
US10582715B2 (en) 2012-03-30 2020-03-10 Givaudan Sa Powder flavour composition
US11091429B2 (en) 2012-03-30 2021-08-17 Givaudan Sa Organic compounds
WO2013149035A2 (fr) 2012-03-30 2013-10-03 Givaudan S.A. Améliorations apportées à des composés organiques ou se rapportant à ceux-ci
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WO2013148991A1 (fr) 2012-03-30 2013-10-03 Givaudan S.A. Dérivés n-acylés d'acide gamma amino-butyrique et de bêta alanine comme composés d'arôme alimentaire
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EP1806977A1 (fr) 2007-07-18

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