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
2000-11-06
2002-01-01
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...
C426S533000, C426S650000
Reexamination Certificate
active
06335047
ABSTRACT:
FIELD OF THE INVENTION
The invention relates generally to epoxydecenal compounds, and specifically to isomeric forms of epoxydecenal having enhanced flavor potency.
BACKGROUND
Epoxydecenal (trans-4,5-epoxy-(E)-2-decenal) (C
10
H
16
O
2
, MW 168.24) is a known flavorant for foods, beverages, or other products. It enhances the flavor and/or odor of these products, making the products more desirable to the consumer. Epoxydecenal is formed from the degradation of fats, and is found in many foodstuffs, including both foods and beverages such as barley malt, French fries, olive oil, baguettes, peanut oil, hazelnut oil, pumpkinseed oil, rambutan fruit, puff pastries, wheat bread, cooked chicken, cooked beef, cooked pork, boiled salmon, cod, anchovy, oat meal, butter, buttermilk, French beans, oranges, and others.
The synthesis of epoxydecenal has been described. The compound was prepared by homologation of the precursor aldehyde epoxide using a Wittig reaction. Epoxydecenal exists in nature as a mixture of two isomers, the (S,S) isomer (
FIG. 1A
) and the (R,R) isomer (FIG.
1
B). The substantially pure (S,S) isomer of epoxydecenal has been synthesized, as reported by Zamboni et al., as an intermediate in the total synthesis of 14S, 15S-oxido 5Z,8Z, 10 E, 12E-eicosatetraenoic acid (
Tetrahedron Letters
, 24: 4899-4902 (1983)).
The use of a catalyst to yield enantiomerically enriched mixtures of epoxydecenal has been reported by Jacobsen et al. (Chang, Lee, and Jacobsen,
J. Org. Chem.
, 58: 6939-6941 (1993)). The report demonstrated the utility of this catalyst to perform regio- and enantioselective catalytic epoxidations, in which conjugated polyenes-cis alkenes are reacted in favor of trans alkenes. The catalytic reaction results in mainly the trans epoxide and yields a high enantiomeric enrichment. An enantiomerically enriched mixture of trans-4,5-epoxy-(E)-2-decenal was synthesized from the cis, trans-decadienol, with an enantiomeric excess (EE) of 83% (a high enantiomeric excess being desirable for resolutions and asymmetric syntheses). There was no mention or suggestion by Jacobsen et al. for using the compounds as flavors or ingredients. While the publication identified both (R,R) and (S,S) epoxydecenal isomers, it neither mentioned nor suggested the odor of the individual isomers.
Racemic mixtures of epoxydecenal have been synthesized for use as an odorant (Schieberle et al,.
Z Lebensm Unters Forsch
192:130-135 (1991) and Lin, Jianming et al,
Lipids
(1999), 34 (10), 1117-1126. In the Schieberle report, epoxidation of decadienal with 3-chloroperbenzoic acid yielded the epoxydecenal mixtures. The compound was prepared for evaluation as an odorant in wheat bread crumbs and for comparison of gas chromatography retention times with known samples. The Lin paper synthesized epoxydecenal using a Wittig reaction as a key step. In both of these reports, there is no mention of the odor activity of the individual isomers.
Among all the reports describing the use of epoxydecenal in foodstuffs, the publication by Buttery (
J. Agric. Food Chem.
, 46: 2764-2769 (1998)), studying corn tortilla chips, mentioned the use of epoxydecenal isomers and stated that two isomers of 4,5-epoxy-(E)-2-decenal (labeled as isomer A and isomer B) were identified. Buttery et al. neither teaches nor discloses the odor or potency of the individual isomers.
Thus, a method to enhance intensity of an epoxydecenal flavorant is desirable.
SUMMARY OF THE INVENTION
The invention is directed to an epoxydecenal (trans-4,5-epoxy-(E)-2-decenal) flavorant composition having increased intensity. The composition contains epoxydecenal that has been enriched to contain at least about 90% of the (−) isomeric form. In some embodiments, the composition may contain up to about 99% of the (−) isomeric form. The composition may be used to flavor foodstuffs, such as foods and beverages, or it may be used in other products such as health care products and pharmaceuticals.
The invention is also directed to a method of flavoring a product with epoxydecenal (trans-4,5-epoxy-(E)-2-decenal). In the method, epoxydecenal (frans-4,5-epoxy-(E)-2-decenal) that has been enriched to contain at least about 90% of the (−) isomeric form is added in an amount sufficient to flavor the product. The amount may be in the range of 0.001 ppb to 10 ppm. The product may be a foodstuff.
The invention is additionally directed to an epoxydecenal flavorant having enhanced intensity. Epoxydecenal (trans-4,5-epoxy-(E)-2-decenal) containing a racemic mixture of the (−) and (+) isomers is synthesized. The enriched mixture is then separated into fractions containing the (−) and (+) isomers, and the fractions containing the (−) isomer are purified and added to a product such as a foodstuff to produce a high-impact flavor.
The composition provides an epoxydecenal (trans-4,5-epoxy-(E)-2-decenal) flavorant with enhanced intensity, permitting a lower concentration of the flavorant to achieve a desired product taste and/or aroma. This results in a more efficient and economical product. These and other embodiments and advantages of the invention will be apparent in light of the following figures and detailed description.
The invention will be further appreciated with respect to the following figures and description.
REFERENCES:
Alaiz, M., et al., Comparative Antioxidant Activity of Maillard- and Oxidized Lipid-Damaged Bovine Serum Albumin, J. Agric. Food Chem., 45, 3250-3254 (1997).
Buttery, R.G. and Ling, L.C., Additional Studies on Flavor Components of Corn Tortilla Chips, J. Agric. Food Chem., 46, 2764-2769 (1998).
Chang, S., et al., Regio- and Enantioselective Catalytic Epoxidation of Conjugated Polyenes: Formal Synthesis of LTA4 Methyl Ester, J. Org. Chem, vol. 58, No. 25, pp. 1639-1641 (1993).
Gassenmeier, K. and Schieberle, P., Formation of the Intense Flavor Compound trans-4-5-epoxy-(E)-2-Decenal in Thermally Treated Fats, JAOCS, vol. 71, No. 12 (Dec. 1994).
Guth, M. and Grosch, W., Determination of Soya-bean Oil: Quantification of Primary Flavour Compounds Using a Stable Isotope Dilution Assay, Lebensm-Wiss. u.-Technol., 23, 513-522 (1990).
Hinterholzer, A. and Schieberle, P., Identification of the Most Odour-active Volatiles in Fresh, Hand-extracted Juice of Valencia Late Oranges by Odour Dilution Techniques, Flavour and Fragrance Journal, vol. 13, pp. 49-55 (1998).
Lee, N.H. and Jacobsen, E.N., Enantioselective Epoxidation of Conjugated Dienes and Enynes. Trans-Epoxides from Cis-Olefins, Tetrahedron Letters, vol. 32, No. 45, pp. 6533-6536 (1991).
Lin, J., et al., Synthesis of trans-4,5-Epoxy-(E)-2-decenal and Its Deuterated Analog Used for the Development of a Sensitive and Selective Quantification Method Based on Isotope Dilution Assay with Negative Chemical Ionization, Lipids, vol. 34, No. 10, pp. 1117-1126 (1999).
Ong, P.K.C., et al., Characterization of Volatiles in Rambutan Fruit (Nephelium lappaceum L.), J. Agric. Food Chem., 46, 611-615 (1998).
Reiners, J. and Grosch, W., Odorants of Virgin Olive Oils with Different Flavor Profiles, J. Agric. Food Chem, vol. 46, 2754-2763 (1998).
Schieberle, P. and Grosch, W., Potent odorants of the wheat bread crumb: Differences to the crust and effect of a longer dough fermentation, Z Lebensm Unters Forsch, 192:130-135 (1991).
Wagner, R.K. and Grosch, W., Key Odorants of French Fries, JAOCS, vol. 75, No. 10, pp. 1385-1392 (1998).
Zamboni, R., et al., The Stereospecific Synthesis of 14S, 15S-Oxido 5Z, 8Z, 10E, 12E-Eicosatetraenoic Acid, Tetrahedron Letters, vol. 24, No. 45, pp. 4899-4902 (1983).
Zhang, W. and Jacobsen, E.N., Asymmetric Olefin Epoxidation with Sodium Hypochlorite Catalyzed by Easily Prepared Chiral Mn(III) Salen Complexes, J. Org. Chem. 56, 2296-2298 (1991).
Daniher Andrew
Furrer Stefan
Goeke Andreas
Givaudan SA
Wong Leslie
Wood, Herron & Evans, L.L.
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