Food or edible material: processes – compositions – and products – Products per se – or processes of preparing or treating... – Flavor per se – or containing flavor or flavor improver of...
Reexamination Certificate
1999-01-29
2001-10-02
Wong, Leslie (Department: 1761)
Food or edible material: processes, compositions, and products
Products per se, or processes of preparing or treating...
Flavor per se, or containing flavor or flavor improver of...
C426S089000, C426S580000, C426S590000, C426S650000
Reexamination Certificate
active
06296889
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to flavoring and aromatic agents and to provision of products to which such agents are added including foods, particularly dairy products and coffee extracts, and including pharmaceuticals, cosmetics and perfumes, to flavor the products and so that they impart aroma, and the invention further relates to identification, isolation, preparation and use of 1-nonen-3-one.
Since the 1950's, yoghurt volatiles have given rise to much interest, and more than 60 flavour compounds have been identified so far (Maars et al., Volatile compounds in food, TNO-CIVO, Food Analysis Institute, The Nederlande, 1994). Its consumption has become very popular since the 1960's due to its delicate flavour associated with its particular texture and the claimed health benefits of lactic acid bacteria for humans. Headspace and simultaneous distillation-extraction (SDE) have been commonly used for the analysis of its flavour. Because of the low intensity of yoghurt odour, the sample is often heated to increase the volatility of the flavourings (Ulbeith et al., Assoc Off. Anal. Chem. 74, 630-634, 1991). This can alter the composition of this sensitive aroma and a mild sampling technique must be applied. Using a purge-and-trap sampling at a lower temperature, Laye and Imhof, respectively identified 23 and 33 compounds (Laye at al., J. Food Sci., 58, 991-995, 1993; Imhof et al., Lebensm. Wiss. u-Technol., 27, 265-269, 1994), but no one has determined the key volatiles responsible for the typical yoghurt aroma. Recently, Imhof et al. suggested 2,3-butanedione, 2,3-pentanedione, dimethyl sulfide and benzaldehyde to be the most potent ingredients in yoghurt aroma (Lebensm. Wiss. u-Technol., Z, 78-86. 1995).
In coffee extracts, Semmelroch et al. identified, as being involved in the aroma impact, 2-methyl propanal, 2-methyl butanal, 2,3,-butanedione, 2,3-pentanedione, 3-methyl-2-butenal and guaiacol (Lebensm-Wiss. u-Technol, 28, 310-313, 1995).
In another respect, 1-nonen-3-one has already been synthesised by oxidation of the corresponding alcohol by pyridinium chlorochromate (Corey et al., Tetrahedron Letters, 31, 2647-2650, 1975; Nakahira et al., J. Org. Chem., 57, 17-28, 1992). 1-Nonen-3-one has not been yet identified in foods, according to the recognised methods agreed by the International Organisation of the Flavour Industry (Z. Lebensm. u-Forsch, 192, 530-534, 1991).
SUMMARY OF THE INVENTION
The object of the present invention is to provide a compound which is involved, in combination with other flavouring agents, in the flavouring of food products, especially dairy and coffee derivatives products.
The present invention provides a process preparing food, pharmaceutical, cosmetic and perfume compositions so that the compositions are flavored and impart aroma which comprises adding 1-nonen-3-one to such compositions in an amount which is effective for flavoring/aromatizing such compositions. As may be gathered from the description below, it has been found that addition of 1-nonen-3-one to a food, in particular to a dairy product, and more particularly to a yoghurt, and in particular also to coffee extract, enhances the aroma of the food, and it may be synthesized and added to the compositions in an amount of from about 1 ppt to about 0.1 ppm.
In another aspect, the present invention comprises preparations of composition mixtures of 1-nonen-3-one and at least a molecule, known to be involved in dairy or coffee aroma, selected from 2,3-butanedione, 2,3-pentanedione, dimethyl sulfide, methional, 2-methyl-tetrahydrothiophen-3-one, 2E-nonenal, guaiacol, methyl propanal, 2-methyl butanal, 3-methyl butanal, 2- and 3-methyl-2-butenal, 2- and 3-methyl butyric acid, 3-methyl-2-butenethiol, 2-methyl furanethiol, 2-furfurylthiol, 3-mercapto-3-methylbutylformate, 4-ethyl guaiacol, 4-vinyl guaiacol, 2-isopropyl-3-methoxypyrazine, 2,3-diethyl-5-methylpyrazine, 2-ethyl-3,5-dimethylpyrazine, 2-isobutyl-3-methoxypyrazine, beta-damascenone, vanillin, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone, 3-hydroxy-4,5-dimethyl-2(5H)-furanone, and 5-ethyl-3-hydroxy-4-ethyl-2(5H)-furanone.
Finally, the present invention provides a composition in a form of a powder which comprises 1-nonen-3-one encapsulated with a polysaccharide.
FURTHER DESCRIPTION OF THE INVENTION
Hyphenated gas chromatography-olfactometric techniques allow the direct determination of impact odorants in foods. Most commonly applied methods are Charm Analysis (Acree et al., The analysis of odor-active volatiles in gas chromatographic effluents, In Analysis of volatiles, de Gruyter, New York, 1984) and Aroma Extract Dilution Analysis (AEDA), (Ullrich and Grosch, Z. Lebensm. Unters. Forsch., 184, 277-282, 1987). Both methods are based on GC-olfactometry of an aroma extract which is diluted until no odor is detected at the sniffing port. More recently, Grosch's group sampled the headspace surrounding the food, since the headspace composition better represents the smell that is perceived by the consumer (Semmelroch and Grosch, Lebensm. Wiss. u-Technol, 28, 310-313, 1995).
Since the vapour phase odor is first perceived when opening a yoghurt pot or above the coffee cup, its quality will influence the consumer's preference. Because the retronasal perception is also sensitive to the headspace odor released by the yoghurt, it is preferable to focus on the headspace and to determine the main odor contributors by using a direct measurement of their individual impact.
However, a critical evaluation of dilution sniffing methods pointed out reproducibility problems (Abbott et al., J. Agric. Food chem., 41, 1698-1703, 1993).
To identify flavours in food products, only one dilution level may be used, and GC-olfactometry may be repeated several times. Aromagrams of individuals are then “averaged” to get rid of previously mentioned reproducibility problems. Resulting aromagrams allow odor profile comparisons as peak intensities are related to the frequencies of odor detection by “NIF” and “SNIF” (respectively, “Nasal Impact Frequency” and “Surface of Nasal Impact Frequency”) see Ott et al., Improved headspace-GC-sniffing technique: screening of aroma impact flavourings. 4
th Int. Symposium on Hyphenated Techniques in Chromatography.
Bruges, Belgium, 1996).
The method described hereafter as “procedure 1c” allows for the first time the detection of 1-nonen-3-one, and other flavouring compounds, in yoghurts and coffee brews. The odor threshold of 1-nonen-3-one is about 8 pg/kg. This extremely low threshold classifies 1-nonen-3-one among the most potent compounds identified in flavours up to now.
Many flavour molecules of dairy product and coffee brews are already known. Each of these molecules does not present a dairy or a coffee flavour. It is the combination of these flavouring molecules which leads to the typical dairy or coffee flavour. In the same way, 1-nonen-3-one presents a mushroom flavour, but when combined with other dairy or coffee flavour molecules, it enhances the final flavour perceived by the consumer. Therefore, the present invention covers also any flavouring compositions consisting essentially of 1-nonen-3-one and flavour molecules involved in the dairy and coffee aroma, said molecules may be selected in the list of flavouring molecules listed above, or presented in the examples.
The addition of 0.1 ppt to 1 ppm of 1-nonen-3-one to a dairy product can surprisingly increase the positive impact of the dairy aroma. The same observation can be made when 1-nonen-3-one is added to a coffee brew. Best results may be obtained when 0.1 ppt to 20 ppt of 1-nonen-3-one is added to a yoghurt. The use according to the invention concerns also any use of 1-nonen-3-one, as flavouring ingredient, in a mixture subjected to a process leading to the formation of a process flavouring.
A solution of polysaccharides may also be added to the reaction mixture, after conversion, and the mixture may then be freeze-dried. The polysaccharides may be cyclodextrine or maltodextrine, which f
Chaintreau Alain
Fay Laurent B.
Ott Andreas
Nestec S.A.
Winston & Strawn
Wong Leslie
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