WO2009141294A1 - Acylamino acid compounds and food preparations containing same - Google Patents

Acylamino acid compounds and food preparations containing same Download PDF

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Publication number
WO2009141294A1
WO2009141294A1 PCT/EP2009/055970 EP2009055970W WO2009141294A1 WO 2009141294 A1 WO2009141294 A1 WO 2009141294A1 EP 2009055970 W EP2009055970 W EP 2009055970W WO 2009141294 A1 WO2009141294 A1 WO 2009141294A1
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Prior art keywords
carbon atoms
food preparation
acid
acylamino acid
group comprises
Prior art date
Application number
PCT/EP2009/055970
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French (fr)
Inventor
Céline Riera
Candice Menozzi
Fabien Robert
Johannes Le Coutre
Original Assignee
Nestec S.A.
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 EP08156555A external-priority patent/EP2123176A1/en
Priority claimed from EP08159689A external-priority patent/EP2140770A1/en
Priority to CA2725155A priority Critical patent/CA2725155C/en
Priority to ES09749784.6T priority patent/ES2621140T3/en
Priority to US12/993,572 priority patent/US9560876B2/en
Priority to CN2009801184014A priority patent/CN102036571B/en
Application filed by Nestec S.A. filed Critical Nestec S.A.
Priority to MX2010012687A priority patent/MX2010012687A/en
Priority to EP09749784.6A priority patent/EP2296492B1/en
Priority to JP2011509942A priority patent/JP2011520457A/en
Priority to BRPI0913063A priority patent/BRPI0913063A8/en
Publication of WO2009141294A1 publication Critical patent/WO2009141294A1/en
Priority to ZA2010/09098A priority patent/ZA201009098B/en
Priority to HK11110576.8A priority patent/HK1155914A1/en

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    • 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
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids

Definitions

  • the present invention relates to the culinary field.
  • the present invention relates in particular to acylamino acid compounds or a salt thereof and their use in food preparations to generate a savory tingling sensation without burning effects.
  • the present invention also relates to food preparations comprising an acylamino acid compound or a salt thereof.
  • TRPVl transient receptor potential Vl
  • TRPAl transient receptor potential Al
  • TRPVl is the receptor for heat and burning sensations such as capsaicin, the hot molecule in red hot chilli peppers.
  • TRPAl responds to cold and pungent compounds such as allyl isothiocyanate (mustard oil) and cinnamaldehyde (cinnamon) . At moderated concentrations, TRPAl agonists exhibit a pleasant tingling sensation.
  • Capsaicin causes a burning sensation when it comes in contact with mucous membranes. Thus, it is commonly used in food products to give them added spice or pungency.
  • the present invention describes, in a first aspect, fatty acid based acylamino acid compounds having the formula
  • Rl is selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms and a carboxyalkyl group having 1 to 10 carbon atoms and R2 is a straight chain hydrocarbon group having 5 to 20 carbon atoms and containing at least one double bond, or a salt thereof.
  • the compounds of the present invention generate new sensory properties. Diverse reactivity properties in vitro of these compounds have been found. More importantly, the acylamino acid compounds of the present invention exert a taste mainly tingling and not burning in the oral cavity when added to a food preparation.
  • the present invention relates to a food preparation comprising an acylamino acid compound or a salt thereof in amount sufficient to generate more tingling than burning sensations in the oral cavity.
  • the compounds of the present invention are major TRPAl agonists which have only a minor effect on TRPVl.
  • the amount of tingling and/or burning sensations generated in the oral cavity can be determined by determining their stimulating effect on TRPAl and TRPVl, respectively, as demonstrated in the present invention.
  • the present invention provides food preparations comprising an acylamino acid compound or a salt thereof sufficient to generate mainly tingling and not burning sensations in the oral cavity.
  • the amino acid compound or a salt is used for generating a mainly tingling and not burning sensation in a food preparation .
  • the figure shows the effect of the compounds of the present invention on TRPAl and TRPVl.
  • the compounds of the present invention are products based on fatty acids and aminoacids which can be either naturally occurring or chemically modified. Both structural units are linked by a coupling reaction.
  • At least one cis double bond is present in the straight chain hydrocarbon group having 5 to 20 carbon atoms.
  • This structural feature induces reactivity on TRPAl providing a mainly tingling taste.
  • TRPVl is only moderately stimulated so that a burning sensation is substantially suppressed.
  • the alkyl group in the above formula comprises 1 to 5 carbon atoms, more preferred 1 to 3 carbon atoms.
  • the compounds of the present invention comprise preferably 1 to 5 carbon atoms, more preferred 1 to 3 carbon atoms.
  • the carboxyalkyl group in the above formula comprises 1 to 5 carbon atoms, more preferred 1 to 3 carbon atoms . It has been shown that the straight chain hydrocarbon group contained in the compounds of the present invention preferably comprises 10 to 18 carbon atoms, with 11 to 17 carbon atoms being preferred.
  • acylamino acid compounds of the present inventions are those, wherein, in the formula, Rl is selected from hydrogen, methyl, hydro- ethyl and carboxyl ethyl and the straight chain hydrocarbon group comprises 11 carbon atoms.
  • the salts of the acylamino acid compounds of the present invention are preferably those usually used in the food industry.
  • Examples for the salts are chlorides, sulfates, phosphates, gluconates, sodium, citrates, carbonates, acetates, lactates.
  • Figure 1 shows a diagram illustrating test experiments using the compounds of the present invention on the ion channels TRPAl and TRPVl.
  • HBSS Hank's Balanced Salt Solution
  • 2 mM CaC12 and 20 mM HEPES pH 7.4
  • Fura-2/AM cytoplasmic calcium indicator
  • [Ca2+]i fluxes from a homogeneous cell population were measured as changes in fluorescence intensity when stimulated with agonists using a FLEXstation (Molecular Devices) .
  • Cells were then challenged with the different sanshool derivatives. Mock cells transfected with pcDNA5/FRT were used as negative controls. Cell viability was checked after alkylamide stimulation using 100 ⁇ M ATP.
  • TRPVl (these concentrations were assessed independently to be saturating under these conditions) .
  • calcium fluxes were measured as changes in fluorescence intensity, before and after the addition of agonists.
  • the peak response was taken to be the characteristic value and was obtained by subtracting the peak value from the baseline (value before injection) .
  • C-GIy which is the carboxylic acid derivative of C coupled to glycine
  • C-Ser which is the carboxylic acid derivative of C coupled to Serine
  • C-GIu which is the carboxylic acid derivative of C coupled to glutamic acid
  • D-AIa being the carboxylic acid derivative of D condensed with alanine
  • Compounds J and K are two natural fatty acids, i.e., palmitoleic and linolenic acids coupled with alanine.
  • Synthetic analogues A, B, C and D are derived from CC- hydroxy-sanshool and have the following formulae:
  • TRPAl has been shown to be strongly stimulated while TRPVl was purely activated.
  • C-AIa, compounds J and K showed a strong stimulating effect on TRPAl, while C-AIa and K are purely activating TRPAl .
  • the compounds of the present invention can be synthesized following methods common in organic chemistry.
  • a synthesis example is a coupling reaction using, as a starting material, a fatty acid and an amino acid to obtain the acylamino acid compound of the present invention.
  • the coupling reaction is a condensation reaction.
  • the fatty acids as well as the amino acid are selected from natural occurring or chemically modified fatty acids or amino acids.
  • the food preparation according to the present invention comprises an acylamino acid compound or a salt thereof in an amount sufficient to generate mainly tingling and not burning sensations in the oral cavity.
  • the food preparation comprises an acylamino acid compound having the following formula :
  • Rl is selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms and a carboxyalkyl group having 1 to 10 carbon atoms and R2 is a straight chain hydrocarbon group having 5 to 20 carbon atoms and containing at least one double bond, or a salt thereof.
  • the content of the acylamino acid compound or a salt thereof in the food preparation is usually in a range of 10 micrograms to 500 milligrams per kilogram.
  • the alkyl group preferably comprises 1 to 5 carbon atoms
  • the hydroxyalkyl group comprises 1 to 5 carbon atoms
  • the carboxyalkyl group comprises 1 to 5 carbon atoms
  • the straight chain hydrocarbon group comprises 10 to 18 carbon atoms.
  • the alkyl group preferably comprises 1 to 3 carbon atoms
  • the hydroxyalkyl group comprises 1 to 3 carbon atoms
  • the carboxyalkyl group comprises 1 to 3 carbon atoms
  • the straight chain hydrocarbon group comprises 11 to 17 carbon atoms.
  • the food preparation comprises an acylamino acid wherein, in the formula, Rl is selected from hydrogen, methyl, hydroxyl ethyl and carboxyl ethyl and the strain chain hydrocarbon group comprises 11 carbon atoms.
  • the compounds of the present invention are particularly applicable to food preparations which demand for a delicate hot sensation in the mouth cavity.
  • food preparations are food additives, food products such as beverages, soups, ice-cream, confectionary, dairy, petfood and neutraceuticals .
  • the acylamino acid "alpha-carboxyamide" compound is formed in situ from the condensation of fatty acids and amino acids available in the food preparation via thermal treatment followed by a basic hydrolysis and final neutralisation.
  • Such a condensation between an acid and an aminoacid may be carried by using a thermal process such as heating in EtOH to about 100 0 C for about 12 h (Indian Journal of Heterocyclic Chemistry 2004 14(1), 81-82); by using a microwaves process (10-12 min, about 150 0 C) as described in Synthetic Communication 2008 38(7) 1028-1035; or by using enzymes such as amylase or acylase.
  • a thermal process such as heating in EtOH to about 100 0 C for about 12 h (Indian Journal of Heterocyclic Chemistry 2004 14(1), 81-82); by using a microwaves process (10-12 min, about 150 0 C) as described in Synthetic Communication 2008 38(7) 1028-1035; or by using enzymes such as amylase or acylase.
  • the acylamino acid compound or a salt thereof as presented above is used for generating a mainly tingling and not burning sensation in a food preparation.
  • the compounds of the present invention are preferably used as a spice, flavour or seasoning.

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  • Life Sciences & Earth Sciences (AREA)
  • Food Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Polymers & Plastics (AREA)
  • Seasonings (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Plant Substances (AREA)

Abstract

An acylamino acid compound is described which can be used in food preparations to generate a savory tingling sensation without burning effect.

Description

Acylamino acid compounds and food preparations containing same
Field of the Invention
The present invention relates to the culinary field. The present invention relates in particular to acylamino acid compounds or a salt thereof and their use in food preparations to generate a savory tingling sensation without burning effects. The present invention also relates to food preparations comprising an acylamino acid compound or a salt thereof.
Background Art
Research on the molecular mechanisms underlying pungent sensations revealed the existence of two cation channels, TRPVl (transient receptor potential Vl) and TRPAl (transient receptor potential Al) that are expressed in the somatosensory fibers innervating the oral cavity. TRPVl is the receptor for heat and burning sensations such as capsaicin, the hot molecule in red hot chilli peppers. TRPAl responds to cold and pungent compounds such as allyl isothiocyanate (mustard oil) and cinnamaldehyde (cinnamon) . At moderated concentrations, TRPAl agonists exhibit a pleasant tingling sensation.
Capsaicin causes a burning sensation when it comes in contact with mucous membranes. Thus, it is commonly used in food products to give them added spice or pungency.
However, food products containing red chilli peppers are frequently not accepted by the consumer as being too hot providing a very unpleasant mouth feeling. In particular, both the tingling and burning effect are considered to be very unsavory affecting the consumption of the food product .
It is therefore an object of the present invention to accommodate the needs of consumers which want to enjoy a spicy food without the interfering effect of burning sensations .
It is also an object of the present invention to provide a spicy food product which can be consumed without any side- effect such as burning sensations in the oral cavity.
Summary of the Invention
Accordingly, this object is achieved by means of the features of the independent claims. The dependent claims further define preferred embodiments of the present invention.
The present invention describes, in a first aspect, fatty acid based acylamino acid compounds having the formula
Figure imgf000004_0001
wherein Rl is selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms and a carboxyalkyl group having 1 to 10 carbon atoms and R2 is a straight chain hydrocarbon group having 5 to 20 carbon atoms and containing at least one double bond, or a salt thereof.
The compounds of the present invention generate new sensory properties. Diverse reactivity properties in vitro of these compounds have been found. More importantly, the acylamino acid compounds of the present invention exert a taste mainly tingling and not burning in the oral cavity when added to a food preparation.
Accordingly, the present invention relates to a food preparation comprising an acylamino acid compound or a salt thereof in amount sufficient to generate more tingling than burning sensations in the oral cavity.
The compounds of the present invention are major TRPAl agonists which have only a minor effect on TRPVl.
The amount of tingling and/or burning sensations generated in the oral cavity can be determined by determining their stimulating effect on TRPAl and TRPVl, respectively, as demonstrated in the present invention.
According to a second aspect of the invention, the present invention provides food preparations comprising an acylamino acid compound or a salt thereof sufficient to generate mainly tingling and not burning sensations in the oral cavity.
Finally, according to a third aspect of the invention, the amino acid compound or a salt is used for generating a mainly tingling and not burning sensation in a food preparation . The invention will now be described in more detail by means of illustrative embodiments.
Brief Description of the Drawing
The figure shows the effect of the compounds of the present invention on TRPAl and TRPVl.
Detailed Description of the present Invention
The compounds of the present invention are products based on fatty acids and aminoacids which can be either naturally occurring or chemically modified. Both structural units are linked by a coupling reaction.
It is essential to the compounds of the present invention that at least one cis double bond is present in the straight chain hydrocarbon group having 5 to 20 carbon atoms. This structural feature induces reactivity on TRPAl providing a mainly tingling taste. At the same time, TRPVl is only moderately stimulated so that a burning sensation is substantially suppressed.
In a preferred embodiment of the present invention, the alkyl group in the above formula comprises 1 to 5 carbon atoms, more preferred 1 to 3 carbon atoms.
The compounds of the present invention comprise preferably 1 to 5 carbon atoms, more preferred 1 to 3 carbon atoms.
In a further preferred embodiment of the present invent- tion, the carboxyalkyl group in the above formula comprises 1 to 5 carbon atoms, more preferred 1 to 3 carbon atoms . It has been shown that the straight chain hydrocarbon group contained in the compounds of the present invention preferably comprises 10 to 18 carbon atoms, with 11 to 17 carbon atoms being preferred.
Particularly preferred examples of the acylamino acid compounds of the present inventions are those, wherein, in the formula, Rl is selected from hydrogen, methyl, hydro- ethyl and carboxyl ethyl and the straight chain hydrocarbon group comprises 11 carbon atoms.
The salts of the acylamino acid compounds of the present invention are preferably those usually used in the food industry. Examples for the salts are chlorides, sulfates, phosphates, gluconates, sodium, citrates, carbonates, acetates, lactates.
Figure 1 shows a diagram illustrating test experiments using the compounds of the present invention on the ion channels TRPAl and TRPVl.
The underlying experiment was performed as follows: Cloning and Expression of Human TRPVl and TRPAl Receptors in HEK 293 Cells: Cloning and expression of these receptors was performed following previously published protocols. Briefly, cloned human TRPVl cDNA was obtained from RZPD (Germany) and hTRPAl cDNA from OriGene
(Rockville, MD) . Genes were subcloned into pcDNA5/FRT (Invitrogen, Carlsbad, CA) to generate stable cell lines using the FIp-In system (Invitrogen) after sequencing verification . Measurement of Intracellular Calcium Levels [Ca2+]i and Membrane Potential Variation in HEK 293 Cells Using a Fluorescent Plate Reader: Cell lines stably expressing TRP channels were seeded into 96-well plates previously coated with poly-D-lysine . Cells were incubated in Hank's Balanced Salt Solution (HBSS) supplemented with 2 mM CaC12 and 20 mM HEPES (pH 7.4), containing the cytoplasmic calcium indicator Fura-2/AM at 2 μM (Molecular Devices, Sunnyvale, CA) . Experiments were conducted at room temperature. [Ca2+]i fluxes from a homogeneous cell population (approximately 100000 cells) were measured as changes in fluorescence intensity when stimulated with agonists using a FLEXstation (Molecular Devices) . Cells were then challenged with the different sanshool derivatives. Mock cells transfected with pcDNA5/FRT were used as negative controls. Cell viability was checked after alkylamide stimulation using 100 μM ATP.
Data Analysis: Responses of molecules in HEK 293 cells were expressed as a percentage of maximum responses evoked by 150 μM cinnamaldehyde for TRPAl and 1 μM capsaicin for
TRPVl (these concentrations were assessed independently to be saturating under these conditions) . For all experiments, calcium fluxes were measured as changes in fluorescence intensity, before and after the addition of agonists. The peak response was taken to be the characteristic value and was obtained by subtracting the peak value from the baseline (value before injection) .
Data obtained from this study were expressed as mean SEM. Statistical analysis was performed using the unpaired
Student t test.
The following compounds have been tested including the reference compounds: green Sichuan which is the extract of Sichuan pepper;
OH-sanshools (major compounds in Sichuan pepper responsible for the tingling and burning tastes) ; synthetic analogues of α-hydroxy-sanshool A, B, C and D, the chemical formulae thereof are shown below;
C-AIa which is the carboxylic acid derivative of C coupled to alanine;
C-GIy which is the carboxylic acid derivative of C coupled to glycine; C-Ser which is the carboxylic acid derivative of C coupled to Serine;
C-GIu which is the carboxylic acid derivative of C coupled to glutamic acid;
D-AIa being the carboxylic acid derivative of D condensed with alanine; and
Compounds J and K are two natural fatty acids, i.e., palmitoleic and linolenic acids coupled with alanine.
All these compounds are shown in Figure 2.
Synthetic analogues A, B, C and D are derived from CC- hydroxy-sanshool and have the following formulae:
Figure imgf000010_0001
Hydroxy-α-sanshool
Figure imgf000010_0002
As can be seen from the maximum activation on TRPAl and TRPVl observed for saturating concentration of the compounds of the present invention, TRPAl has been shown to be strongly stimulated while TRPVl was purely activated. In particular, C-AIa, compounds J and K showed a strong stimulating effect on TRPAl, while C-AIa and K are purely activating TRPAl .
The compounds of the present invention can be synthesized following methods common in organic chemistry. A synthesis example is a coupling reaction using, as a starting material, a fatty acid and an amino acid to obtain the acylamino acid compound of the present invention. In a preferred embodiment, the coupling reaction is a condensation reaction. The fatty acids as well as the amino acid are selected from natural occurring or chemically modified fatty acids or amino acids.
The food preparation according to the present invention comprises an acylamino acid compound or a salt thereof in an amount sufficient to generate mainly tingling and not burning sensations in the oral cavity. In a preferred embodiment of the present invention, the food preparation comprises an acylamino acid compound having the following formula :
Figure imgf000011_0001
wherein Rl is selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms and a carboxyalkyl group having 1 to 10 carbon atoms and R2 is a straight chain hydrocarbon group having 5 to 20 carbon atoms and containing at least one double bond, or a salt thereof.
The content of the acylamino acid compound or a salt thereof in the food preparation is usually in a range of 10 micrograms to 500 milligrams per kilogram.
In the above formula, the alkyl group preferably comprises 1 to 5 carbon atoms, the hydroxyalkyl group comprises 1 to 5 carbon atoms, the carboxyalkyl group comprises 1 to 5 carbon atoms and the straight chain hydrocarbon group comprises 10 to 18 carbon atoms.
More preferred, in the above formula, the alkyl group preferably comprises 1 to 3 carbon atoms, the hydroxyalkyl group comprises 1 to 3 carbon atoms, the carboxyalkyl group comprises 1 to 3 carbon atoms and the straight chain hydrocarbon group comprises 11 to 17 carbon atoms. In a particular preferred embodiment of the invention, the food preparation comprises an acylamino acid wherein, in the formula, Rl is selected from hydrogen, methyl, hydroxyl ethyl and carboxyl ethyl and the strain chain hydrocarbon group comprises 11 carbon atoms.
The compounds of the present invention are particularly applicable to food preparations which demand for a delicate hot sensation in the mouth cavity. Examples of food preparations are food additives, food products such as beverages, soups, ice-cream, confectionary, dairy, petfood and neutraceuticals .
In an alternative embodiment of the present invention, the acylamino acid "alpha-carboxyamide" compound is formed in situ from the condensation of fatty acids and amino acids available in the food preparation via thermal treatment followed by a basic hydrolysis and final neutralisation.
Such a condensation between an acid and an aminoacid may be carried by using a thermal process such as heating in EtOH to about 100 0C for about 12 h (Indian Journal of Heterocyclic Chemistry 2004 14(1), 81-82); by using a microwaves process (10-12 min, about 150 0C) as described in Synthetic Communication 2008 38(7) 1028-1035; or by using enzymes such as amylase or acylase.
It has been shown that replacing the carboxyl terminus of the fatty acid by an amino acid potentiated dramatically the effect on TRPAl and abolished the activity on TRPVl. The compounds of the present invention used in food preparations have been surprisingly shown to provide mainly tingling sensations in the mouth cavity without exhibiting the unpleasant accompanying burning sensation usually occurring with the extract of Sichuan pepper.
According to the invention, the acylamino acid compound or a salt thereof as presented above is used for generating a mainly tingling and not burning sensation in a food preparation. The compounds of the present invention are preferably used as a spice, flavour or seasoning.

Claims

Claims
1. A food preparation comprising an acylamino acid compound or a salt thereof in amount sufficient to generate mainly tingling and not burning sensations in the oral cavity.
2. The food preparation according to claim 1 wherein the acylamino acid compound has the following formula:
Figure imgf000014_0001
wherein Rl is selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms and a carboxyalkyl group having 2 to 10 carbon atoms and R2 is a straight chain hydrocarbon group having 5 to 20 carbon atoms and containing at least one double bond, or an salt thereof .
3. The food preparation according to claim 2 wherein, in the formula, the alkyl group comprises 1 to 5 carbon atoms, the hydroxyalkyl group comprises 1 to 5 carbon atoms, the carboxyalkyl group comprises 1 to 5 carbon atoms and/or the straight chain hydrocarbon group comprises 10 to 18 carbon atoms.
4. The food preparation according to any of claims 2 to
4 wherein, in the formula, Rl is selected from hydrogen, methyl, hydroxyethyl and carboxyethyl, and the straight chain hydrocarbon group comprises 11 carbon atoms .
5. The food preparation according to any of claims 1-4, wherein the acylamino acid compound is selected from the group consisting of (S, Z) -2-dodec-5- enamidopropanoic acid, (Z) -2-dodec-5-enamidoacetic acid, (S)-2-((9Z,12Z,15Z) -octadeca-9, 12, 15 trienamido) propanoic acid, (S, Z) -2-hexadec-9- enamidopropanoic acid, (S) -2- ( (2E, 6Z) -dodeca-2, 6- dienamido) propanoic acid, or combinations thereof.
6. The food preparation according to any of claims 1 to
5 wherein the acylamino acid compound is formed in situ by condensation from fatty acids and amino acids available in the food preparation.
7. Use of an acylamino acid compound or a salt thereof for generating a mainly tingling and not burning sensation in a food preparation.
8. The use of claim 7 wherein the acylamino acid compound or a salt thereof comprises the formula
Figure imgf000015_0001
wherein Rl is selected from hydrogen, an alkyl group having 1 to 10 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms and a carboxyalkyl group having 1 to 10 carbon atoms and R2 is a straight chain hydrocarbon group having 5 to 20 carbon atoms and containing at least one double bond, or an salt thereof .
9. The use according to claim 8 wherein, in the formula, the alkyl group comprises 1 to 5 carbon atoms, the hydroxyalkyl group comprises 1 to 5 carbon atoms, the carboxyalkyl group comprises 1 to 5 carbon atoms and the straight chain hydrocarbon group comprises 10 to 18 carbon atoms.
10. The use according to one of claims 7-9, wherein the acylamino acid compound is selected from the group consisting of (S, Z) -2-dodec-5-enamidopropanoic acid, (Z) -2-dodec-5-enamidoacetic acid, (S) -2- ( (9Z, 12Z, 15Z) -octadeca-9, 12, 15-trienamido) propanoic acid, (S, Z) -2-hexadec-9-enamidopropanoic acid, (S) -2- ( (2E, 6Z) -dodeca-2, 6-dienamido) propanoic acid, or combinations thereof.
11. The use according to any one of the claims 7 to 10 as a spice, flavour or seasoning.
PCT/EP2009/055970 2008-05-20 2009-05-18 Acylamino acid compounds and food preparations containing same WO2009141294A1 (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
BRPI0913063A BRPI0913063A8 (en) 2008-05-20 2009-05-18 USE OF AN ACYLAMINOACID COMPOUND OR A SALT THEREOF TO GENERATE A MAINLY SPICY AND NON-BURNING SENSATION IN A FOOD PREPARATION, AND FOOD PREPARATION COMPRISING SAID COMPOUND
JP2011509942A JP2011520457A (en) 2008-05-20 2009-05-18 Acylamino acid compound and food preparation containing acylamino acid compound
ES09749784.6T ES2621140T3 (en) 2008-05-20 2009-05-18 Acylamino acid compounds and food preparations containing them
US12/993,572 US9560876B2 (en) 2008-05-20 2009-05-18 Acylamino acid compounds and food preparations containing same
CN2009801184014A CN102036571B (en) 2008-05-20 2009-05-18 Acylamino acid compounds and food preparations containing same
CA2725155A CA2725155C (en) 2008-05-20 2009-05-18 Acylamino acid compounds and food preparations containing same
MX2010012687A MX2010012687A (en) 2008-05-20 2009-05-18 Acylamino acid compounds and food preparations containing same.
EP09749784.6A EP2296492B1 (en) 2008-05-20 2009-05-18 Acylamino acid compounds and food preparations containing same
ZA2010/09098A ZA201009098B (en) 2008-05-20 2010-12-17 Acylamino acid compounds and food preparations containing same
HK11110576.8A HK1155914A1 (en) 2008-05-20 2011-10-06 Acylamino acid compounds and food preparations containing same

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP08156555A EP2123176A1 (en) 2008-05-20 2008-05-20 Acylamino acid compounds and food preparations containing same
EP08156555.8 2008-05-20
EP08159689.2 2008-07-04
EP08159689A EP2140770A1 (en) 2008-07-04 2008-07-04 Acylamino acid compounds and food preparations containing same

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CN (1) CN102036571B (en)
BR (1) BRPI0913063A8 (en)
CA (1) CA2725155C (en)
CL (1) CL2009001252A1 (en)
ES (1) ES2621140T3 (en)
HK (1) HK1155914A1 (en)
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EP2597082A1 (en) 2011-11-24 2013-05-29 Symrise AG Compounds for masking an unpleasant taste
WO2013149025A1 (en) * 2012-03-30 2013-10-03 Givaudan, S., A. N-acyl serine derivatives as food flavouring compounds
WO2013148997A1 (en) * 2012-03-30 2013-10-03 Givaudan, S.A. N-acylated 1 - aminocycloalkyl carboxylic acids as food flavouring compounds
WO2013148991A1 (en) * 2012-03-30 2013-10-03 Givaudan S.A. N-acyl derivatives of gamma amino - butyric acid and and beta alanine as food flavouring compounds
WO2013148965A2 (en) 2012-03-30 2013-10-03 Givaudan S.A. Improvements in or relating to organic compounds
WO2013149012A1 (en) * 2012-03-30 2013-10-03 Givaudan S.A. N-acyl amino acid derivatives as food flavouring compounds
WO2013149022A1 (en) * 2012-03-30 2013-10-03 Givaudan S.A. N-acyl proline derivatives as food flavouring compounds
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