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
2002-02-19
2003-08-19
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...
C426S580000, C426S583000, C426S650000
Reexamination Certificate
active
06607773
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to a process for preparing tree alkylphenol flavor concentrates. For the purpose of this invention free alkylphenol flavor concentrates are defined as free alkylphenol solutions resulting from the treatment of a naturally-occurring source of bound alkylphenol conjugates. Such concentrates and synthetic alkylphenols are used as additives in various food products for the enhancement of food flavors and food appearance. For the purpose of this invention alkylphenols are defined as phenols substituted with one or more saturated or unsaturated alkyl groups, where the groups can be the same or different. Alkylphenols are naturally produced in the digestive systems of dairy and meat animals, and are thus present in various food products, such as meats (Ha, J. K. and Lindsay, R. C.
Volatile Alkylphenols and Thiophenol in Species
-
Related Characterizing Flavors of Red Meats
, J. Food Sci. 56:1197 (1991) (incorporated herein by reference)); milks and cheeses (Ha, J. K. and Lindsay, R. C.
Volatile Branched
-
Chain Fatty Acids and Phenolic Compounds in Aged Italian Cheese Flavors
, J. Food Sci. 56:1241 (1991); Ha, J. K. and Lindsay, R. C.
Contributions of Cow, Sheep and Goat Milks to Characterizing Branched
-
Chain Fatty Acids and Phenolic Flavors in Varietal Cheeses
, J. Dairy Sci. 74:3267 (1991) (incorporated herein by reference)); cashews (Tyman, J. H. P. et al.
The Extraction of Natural Cashew Nut
-
Shell Liquid from the Cashew Nut
(
Anacardium occidentale
), J. Am. Oil Chem. Soc. 66:553 (1989)); and off-flavored fish (Heil, T. P. and Lindsay, R. C.
A Method for Quantitative Analysis of Flavor
-
Tainting Alkylphenols and Aromatic Thiols in Fish
, Environ. Sci. Health. B23:475-88 (1988) (incorporated herein by reference)). For example, various aged Italian cheeses contain many volatile, or “free” alkylphenols in concentrations ranging from 1 part per billion (“ppb”) to 924 ppb, but the specific alkylphenols present, as well as their concentration, vary from cheese to cheese. (Ha, J. K. and Lindsay, R. C.
Volatile Branched
-
Chain Fatty Acids and Phenolic Compounds in Aged Italian Cheese Flavors
. J. Food Sci. 56:1241 (1991) (incorporated herein by reference)). P-cresol and m-cresol have also been found in butter oil at a concentration of 4.9 ppb and 3.3 ppb respectively. (Urbach et al.,
Die Isolierung and Bestimung von Phenol, o
-
Methoxyphenol und m
-
und p
-
Cresol in Butter,
18
th
Int. Dairy Congr., Sydney 1E, 234 (1970)).
Alkylphenols have been identified as important components in the flavors of ruminant meats and dairy products. For the purpose of this invention, ruminant is defined as relating to a multiple-stomached animal, such as bovine, caprine and ovine. Alkylphenols are present in both the free and conjugate-bound forms, but only the free forms contribute to the flavor of the product. Alkylphenols are very potent flavor compounds, providing noticeable flavor at low parts per billion concentrations. Studies by Urbach showed that the addition of 2 ppb of p-cresol and 200 ppb of m-cresol to a model butter prepared from deodorized butter oil and distilled water, produced desirable flavor notes, but that undesirable flavors in the butter resulted from the use of p-cresol and m-cresol in amounts greater than 100 ppb and 1 part per million (“ppm”) respectively. (Urbach et al.,
Volatile Compounds in Butter Oil
, J. Dairy Res. 39:35 (1972)).
The free alkylphenols found in dairy products, such as milk, and in animal tissue are generally highly soluble in fats, such that when fats are removed from these products, the free alkylphenols are also substantially removed. As a result, such “fat free” products do not have the flavor of their fat-containing counterparts, making them less desirable to consumers.
The flavorful free alkylphenols naturally found in meat and dairy products are produced in the digestive tract via normal processes and/or via ingestion of feeds containing alkylphenols. However, most of the alkylphenols found in milk, urine and animal tissue are metabolic conjugates, such as glucuronides, sulfates, and phosphates, which are not believed to have much, if any, flavor effect. Therefore, lab-scale methods have been developed to produce free alkylphenols from these alkylphenol conjugates, including enzyme hydrolysis using &bgr;-D glucuronidase, arylsulfatase, and acid phosphatase, simultaneous distillation extraction and adsorption.
Moreover, despite the fact that free alkylphenols are recognized as contributing flavors to food products, to date these compounds have not been used as flavor enhancers in the food industry because usefulness of the free alkylphenols as flavor enhancers for “fat free” or “reduced fat” products has not yet been recognized. In addition, the above processes for isolating free alkylphenols from food products such as milk and animal tissue are difficult, expensive and time consuming, and have only been accomplished on a small scale.
Therefore, a process for producing free alkylphenol flavor concentrates from raw materials containing bound alkylphenol conjugates that is efficient, simple, inexpensive, and that can be performed on a large scale is needed. A process for using these free alkylphenol flavor concentrates as flavor enhancers in food products, especially “fat free” or “reduced fat” products, is also needed. A process for using synthetic alkylphenols as flavor enhancers in food products, especially “fat free” or “reduced fat” products, is also needed. A “fat free” or “reduced fat” food product with a flavor substantially matching that of its counterpart wherein the fat has not been removed is needed. Further, there is a need for a free alkylphenol flavor concentrate that can enhance the appearance of food products and be applied in a controlled manner to impact flavor and color in desired locations in or on the food product.
These needs are met by the present invention.
SUMMARY OF THE INVENTION
A process for producing free alkylphenols from raw materials containing bound alkylphenol conjugates and the subsequent recovery of the free alkylphenols as a free alkylphenol flavor and color concentrate has been discovered. In addition, applications of free alkylphenols, both in synthetic form and as a free alkylphenol flavor concentrate derived from the above process, as flavor enhancers in various food products have been discovered. The release of the bound alkylphenols from their non-flavorful conjugates provides the active flavorful compounds that are present in dairy and ruminant meat products in low concentrations. These free alkylphenols, when added in the appropriate amounts to food products provide the characteristic flavors of these foods. Therefore, even “fat free” or “reduced fat” food products will have a flavor substantially matching that of their counterparts wherein the fat has not been removed.
In the process of the present invention, the free alkylphenols are released from their bound form by reacting raw materials containing bound alkylphenol conjugates with a strong acid, such as sulfuric acid, phosphoric acid or hydrochloric acid, to effect hydrolysis of the alkylphenol conjugates. Preferably, a reacting time period is used to cause sufficient degradation and/or polymerization of interfering flavors, proteins and carbohydrates present in the raw material to avoid sweet molasses-like flavor notes. The sufficient time period is normally about one to about eight hours. The resulting hydrolyzed free alkylphenol flavor concentrates may be partially neutralized with a base, such as sodium hydroxide, sodium carbonate, ammonium hydroxide, sodium bicarbonate, potassium hydroxide or potassium carbonate, if desired.
The free alkylphenol flavor concentrates should then be analyzed to determine the profile, or types and concentration of free alkylphenols present in the concentrate. It is essential to control the concentration of alkylphenols that are added via the free alkylphenol flavor concentrates, and to do this, the concentration of alkylphenols in the free alkylph
Michael Best & Freidrich LLP
Ward Jeffrey S.
Whole Flavors, LLC
Wong Leslie
Yager Charlene L.
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