CA1337854C - Culinary mixes for products prepared from batters and doughs with fish oils stabilized with fructose - Google Patents
Culinary mixes for products prepared from batters and doughs with fish oils stabilized with fructoseInfo
- Publication number
- CA1337854C CA1337854C CA 589109 CA589109A CA1337854C CA 1337854 C CA1337854 C CA 1337854C CA 589109 CA589109 CA 589109 CA 589109 A CA589109 A CA 589109A CA 1337854 C CA1337854 C CA 1337854C
- Authority
- CA
- Canada
- Prior art keywords
- fructose
- fish oil
- weight
- fish
- culinary
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/18—Carbohydrates
- A21D2/181—Sugars or sugar alcohols
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D10/00—Batters, dough or mixtures before baking
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/16—Fatty acid esters
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/34—Animal material
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Zoology (AREA)
- Edible Oils And Fats (AREA)
Abstract
Disclosed are food products, especially culinary mixes and baked goods prepared therefrom which contain nonhydrogenated fish oil yet which exhibit enhanced stability of the fish oil against flavor and aroma degradation. The improved food products are stabilized by the incorporation of the food product such that the weight ratio of fructose to fish oil is at least about 0.05:1. Surprisingly, incorporation of modest amounts of fructose in food products within the indicated minimum provides a stabilizing effect of the highly unstable fish oil. The present invention finds particular suitability for use in connection with fish oils rich in omega-3 fatty acids.
Description
CULINARY ~IIXES FOR PRODUCTS PREPARED
FROM BATTERS AND DOUGHS WITH FISH OILS
STABILIZED WITH FRUCTOSE
BACKGR~UND OF TXE INVE~TION
1. Technical Field The present invention relates to food products.
More particularly, the present invention relates to culinary mixes and to baked goods containing fish oils characterized by better flavor and enhanced stability.
FROM BATTERS AND DOUGHS WITH FISH OILS
STABILIZED WITH FRUCTOSE
BACKGR~UND OF TXE INVE~TION
1. Technical Field The present invention relates to food products.
More particularly, the present invention relates to culinary mixes and to baked goods containing fish oils characterized by better flavor and enhanced stability.
2. Background Art A great deal of attention has been paid recently to the various health benefits apparently associated with consumption of fish rich in fish oil.
Health benefits appear to be related to the presence of high levels of the n-3 family of polyunsaturated fatty acids. Oils containing such materials, such as fish oils, are referred to as "omega-3" oils and desirably contain high levels of n-3 fatty acids, especially eicosapentaenoic acid ("EPA") and docosahexaenoic acid ("DHA"). Such fatty acids are called "omega-3" since the first double bond occurs in the third carbon bond counting from the end or omega position of the fatty acid.
Notwithstanding the present interest in the health benefits of fish oil consumption, nonhydrogenated fish oil generally to date has not been widely used per se or as an ingredient in processed food products for use by humans due to notorious and severe problems in odor and flavor. However, gelatin capsules containing fish oil are available. Additionally, salmon oil has been added to canned salmon. Also, certain canned meat products have been marketed in Japan which have had refined fish oil added as a fortifier.
Hydrogenated fish oils are much more stable due to the decrease in the degree of polyunsaturation and are widely used in Europe for margarine. Hydrogenated fish oils have also been used in Scandinavian countries in other consumer products, e.g., finished cake.
(See also U.S. Patent Nos. 3,168,405, 3,268,337, 3,366,487) and margarine (see "Use of Fish Oils in Margarine and Shortening," Chapter 18, Fish Oils, Avi Publishing Co., Inc. 1968). Hydrogenation is also effective in reducing odor and flavor after deodorization. However, hydrogenation by decreasing polyunsaturation including the n-3 fatty acid component correspondingly decreases the health value of fish oil. Accordingly, it would be desirable to realize food products containing such nonhydrogenated fish oils, but the instability of the fish oil to date has prevented the development of such food products.
The principal approach taken in the art to utilize nonhydrogenated fish oil in processed foods generally has been to employ fish oils of enhanced stability. Two broad approaches have been taken in 3S the art to realize nonhydrogenated fish oils of enhanced stability. The first approach involves giving attention to the processing of the oil to achieve a cleaner, finished oil product. Particular attention has been given to the deodorization step in order to realize cleaner finished fish oil products.
In the second approach, the art has attempted to find adjuvants which can be added to finished fish oil to provide desired additional stability. For example, while the phenomenon of fish oil degradation is not completely understood, it is known, however, that oxidative rancidification is a contributing factor.
Addition of known antioxidants, singly as well as commercial mixtures, some allegedly synergistic, does result in some increase in stability. However, the instability of nonhydrogenated fish oils is so great, that even addition of such materials at maximum legally permitted levels provide only modest increases in stability.
Given the severe difficulties in realizing a suitable fish oil ingredient, it is understandable that comparatively little developmental effort has been made to formulate processed food products containing fish oil.
The prior art also includes U.S. Patent No. 4,357,362 (issued Nov. 2, 1982 to David Barker).
This patent discloses a pet food composition including fish material of reduced fishy odor by subjecting the composition in a sealed container, to sterilizing heat in the presence of a reducing agent. However, several disadvantages or limitations exist with this approach. First, the primary advantage is a fish odor reduction which is not necessarily directly related to the problems of fish oil flavor degradation. Second, a severe heat treatment in a sealed container is required in order to achieve the reduction in odor. It is 3~ undesirable for many foods to be subjected to such severe heat treatment. Third, fish flesh or fish -proteinaceous material is known to have a material effect on stability. However, most food products cannot contain fish flesh as a practical matter, e.g., mayonnaise, yet could beneficially include fish oil were oil stability nonetheless obtained. Also, the product is less susceptible to oxidative rancidity since it is sealed. Finally, a wide variety of organic and inorganic reducing agents are taught as useful although reducing sugars are preferred.
Still another problem exists with the utilization of fish oil in baked goods which is peculiar to their method of preparation. Baked goods, of course, are prepared from batters by a baking step, typically as short as 6 minutes for cupcakes or muffins to as long as 40 minutes for larger layer cakes in a baking oven at 300 F to 400 F. Exposure of nonhydrogenated fish oil to oxygen in the presence of moisture at these elevated temperature conditions would quickly cause development in clean fish oils of a strong and unpalatable fishy flavor. Conventional layer cakes with added, very clean, antioxidant stabilized, nonhydrogenated deodorized fish oils exit the oven with an impalatable fish flavor.
Given the state of the art with regard to fish oil stabilization, there is a continuing need for the development of new and improved processed food products containing fish oil of improved stability.
Accordingly, it is an object of the present invention to provide food products containing nonhydrogenated fish oils which nonetheless exhibit improved stability against degradation in both flavor and odor.
It is an object of the present invention to provide culinary mixes for baked goods containing 3~ nonhydrogenated fish oil.
It is another object of the present invention to provide food products of enhanced stability which do not require heat sterilization.
Another object of the present invention is to provide food products containing fish oil which do not require fish meat.
Still another object of the present invention is to provide food products containing fish oil of enhanced stability against flavor degradation.
Another important object is to provide food products with water which contain fish oil yet nonetheless exhibit increased stability.
It has been surprisingly discovered that the above objectives can be realized and superior culinary mixes for baked goods and baked goods containing fish oils can be prepared by incorporation of modest amounts of fructose. Surprisingly, fructose alone among sugars and other materials appears to be unexpectedly superior in providing the desired stabilization benefits.
SUMM~RY OF THE INVENTION
The present invention relates to culinary mixes for products prepared from batters and doughs containing fish oils of enhanced stability and to the baked goods themselves. In addition to common culinary mix ingredients of flour, shortening and leavening, the present compositions further essentially comprise finished deodorized, nonhydrogenated fish oils stabilized with minor amounts of fructose. The fish oiis also essentially include the maximum permitted levels of TBHQ and also contain tocopherol. The present invention further provides finished baked goods containing fish oil.
. ~
Accordingly, in one aspect, the present invention relates to a two part culinary mix comprising:
1. a first portion separately packaged and comprising a dry mix blend containing a farinaceous material, shortening and leavening and a fructose component in the amount of about 0.1% to 30% by weight of said culinary mix, and 2. a second portion separately packaged and hermetically sealed containing a nonhydrogenated refined, deoderized fish oil in the amount of about 0.1% to 18% by weight of said culinary mix, said fish oil containing, a. about 100 to 300 ppm of an antioxidant selected from the group consisting of tertiary butyl hydroquinone, butylated hydroxyanisole, butylated hydroxytoluene and mixtures thereof, b. about 1 to 2000 ppm of tocopherol.
In a further aspect, the present invention relates to a batter for a baked good comprising water and a culinary mix including a farinaceous material, shortening and leavening, additionally comprising, 1. about 0.1% to 18% by weight of the culinary mix being a nonhydrogenated refined, deodorized fish oil said fish oil containing, - 5a -a. about 100 to 300 ppm of an antioxidant selected from the group consisting of tertiary butyl hydroquinone, butylated hydroxyanisole, butylated hydroxytoluene and mixtures thereof, b. about 1 to 2000 ppm of tocopherol, and 2. about 0.1% to 30% by weight of the culinary mix being fructose and wherein the weight ratio of fructose to fish oil is at least about 10:100.
DETAILED DESCRIPTION OF THE INVENTION
The present invention resides in culinary mixes for products prepared from batters and doughs, - 5b -especially baked goods and to the finished goods themselves containing nonhydrogenated fish oil but which are substantially free of fish flesh. Nonetheless, the present finished goods are characterized by enhanced oil stability by virtue of the incorporation of minor amounts of fructose relative to similar compositions but not containing the requisite fructose amounts.
In its method aspect, the present invention resides in methods for fish oil fortification of finished and baked goods.
Throughout the specification and claims, percentages are by weight and temperatures in degrees Fahrenheit, unless otherwise indicated.
The present invention resides in part in the surprising discovery that otherwise conventional finished farinaceous goods, especially baked goods, and culinary mixes therefor can be prepared that include modest levels of nonhydrogenated, refined, deodorized and stabilized fish oil in partial substitution for other conventional shortening components so long as the goods also meet both of two conditions: first, that the goods include fructose within specified levels;
and second, that the fish oil also essentially includes the maximum permitted levels of selected antioxidants.
In another aspect, the present invention resides in the discovery that a specific combination of antioxidants, namely, TBHQ and tocopherol, provide unexpected superiority when used in combination with fructose for fish oil stabilization in farinaceous goods.
Among all antioxidants or combinations thereof, the combination of TBHQ at its maximum permitted levels plus tocopherol gives surprising fish oil stability benefits compared to other antioxidants or combinations thereof.
Culinary mixes for farinaceous goods to be prepared from batters and doughs are, of course, -well known and the skilled artisan will have no problem selecting specific ingredients and their concentrations formulated to prepare specific baked or finished goods and flavors. Indeed, the art is replete with such formulations. (See, for example, U.S. Patent Nos. 3,708,309 issued Jan. 2, 1973 to Johnson et al.;
3,694,229 issued Sep. 26, 1972 to Norsby et al.; 3,366,487 issued Sep. 29, 1969 to Hatton et al. Culinary mixes typically comprise flour or a farinaceous material, (occasionally corn flour) as the base or principal ingredient, plus shortening (with emulsifiers) and chemical leavening. Typically, for most but not all baked goods, the culinary mixes additionally essentially comprise a nutritive carbo~ydrate sweetening agent(s) which is typically sucrose and occasionally mixtures of sucrose with other`sweeteners.
The term "baked goods" and the culinary mixes therefor is meant to be broadly construed and to include, for example, layer cakes, pound cakes, brownies, muffins, cupcakes, cookies, coffee cakes, bundt cakes and biscuits. Although not literally a "baked good" since they are not baked, pancakes and waffles are also meant to be included since they are similar in formulation.
Exemplary culinary mix formulations are given below.
Flour Sugar Shor'ening Leavening Layer cakes and cupcakes 41 45 6-12 1-2 Muffins 50 25 10-15 2-3 Cookies 20-30 40-50 15-25 .5-1.0 Biscuits 80 10-18 15-20 2-3.5 Brownies 25-30 25 13-14 .1-.2 Still another essential ingredient of the instant, improved com~ositions is a refined, deodorized, nonhydrogenated, stabilized fish oil. The present food products provide convenient vehicles for delivery for consumption of fish oil to obtain the desirable special nutritional advantages provided by fish oil.
The fish oil is used in partial substitution for the conventional shortening ingredient. Desirably, the fish oils comprise from about 0.1~ to 18%, preferably about 4% to 12% of the culinary mixes. The finished baked goods should comprise about 2% to 10% fish oil, preferably about 4% to 8%. The modest differences in the upper values for the fish oil concentrations of the culinary mixes is due to the additional moisture or added solids typically added to the culinary mixes to form batters in baked goods preparation less the minor moisture losses occa~ioned during baking.
Fish oils are staples of commerce and their general processing is`well known (see, for example, Fish Oils: Their Chemistry, Technology, Stability, Nutritional Properties, and Uses, ed. by M. E. Stansby, The Avi Publishing Company, Inc. 1967. Especially use~ul for their therapeutic value herein are oils having a total n-3 fatty acid content of greater than about 20% such as are derived from menhaden oil, herring, capelin, anchovy, cod liver, salmon oil, sardine oil and mixtures thereof. Especially prefered for use herein is menhaden oil due to such supply considerations as cost and availability as well as its nutritional quality as being high in omega-3 fats. Recently, fish oil has been sold in gelatin capsules as a good supplement. However, in the present invention the fish oils are essentially also conventionally processed, e.g., refined and deodorized, t-o provide what is referred to in the art as a "finlshed"
oil. Unlike vegetable oils, however, fish oils typically do not require degumming. Also, conventional ,~' ~
hydrogenation of the fish oil such as is done to make the oil suitable for use for the preparation of margarine-is to be strictly avoided.
The present fish oils must be stabilized, i.e., will essentially include conventional oil stabilizing or materials at their maximum permitted levels (e.g., 200 ppm of total oil) such as antioxidants selected from the group consisting of TB~Q, (tertiary butyl hydroquinone) BHA (butylated hydroxyanisole) or BHT (butylated hydroxytoluene). Not all food approved antioxidants have been shown to be useful.
For example, the use of lecithin has actually been shown to aggravate development of fishy flavors.
Even more preferred products further include 1 to 2000 ppm tocopherol in addition to the antioxidant(s).
Surprisingly, the combination of T~HQ and tocopherol has unexpectedly been found to be superior to other antioxidants generally considered to be equivalents or substitutes. Thus, TB~Q is the antioxidant of choice. Still mo,e preferred products include 10 to 100 ppm (based on total oil) of a chelating agent desirably selected from the group consisting of citric acid, phytic acid, ethylene diamine tetra acetate and mixtures thereof. The food products can also beneficially include about 0.1% to 3~ of the fish oil of an oil soluble flavor masking agent based upon the weight of fish oil.
Preferred flavor masking agents include citrus oils, especially lemon oil.
Preferably, the fish oils useful herein are "Process for Simultaneous ~eodorization and Cholesterol Reduction of Fats and Oils" (Canadian Patent Application Serial No. 549,905, filed Oct. 21, 1987 to Marschner et al). The process there disclosed involves a process involving deaerating fish oil, mixing the oil with steam, heating, flash vaporization, thin ~ 4 _ 9 -film stripping with counter current steam (all steps being performed under vacuum). The finished fish oil prepared according to this method is additionally characterized both by reduced cholesterol (generally at cholesterol levels of less than about 400 mg/g, preferably less than about 250 mg/g) and enhanced stability by enhanced initial quality.
It is essential that the present culinary mixes and baked goods containing fish oil also contain fructose in order to realize the oil stability advantages discovered herein. Of course, fructose has been taught as useful for addition to culinary mixes at varying levels in substitution for conventional sucrose.
It is essential, however, that present food compositions comprise fructose such that the weight ratio of fructose to fish oil is at least about 5 to 30:100. Insufficient fructose can result in rapid deterioration of quality of the food product. As the oil degrades, the resultant fishy flavor and aroma increases rendering the food product increasingly unpalatable. ~xcessive fructose levels can result in products characterized by undesirable sweetness without obtaining proportional increases in oil stability, if any. Better results in terms of obtaining oil stabilization benefits without excessive sweetness are obtained when the food compositions contain fructose to oil in a ratio of at least 10:100. Best results are obtained when the food products contain fructose to oil in a ratio of at least 20:100.
The fructose can be provided from both relatively pure and less pure sources. r~hile pure crystalline fructose of various types and sources are commercially available, fructose in the form of high fructose corn syrup is practical from both a source availability and cost fructose corn syrup functions not only to provide the essential fructose -fish oil stabilizer, but also functions as a sweetener.
Less preferred but nonetheless useful herein are - less pure sources of fructose, e.g., corn syrup, honey, maple syrup solids, fruit juice solids and the like.
Surprisingly, only fructose has been found to provide the high stabilization benefits of the present invention at the concentrations taught as essential herein and no satisfactory explanation can be set forward as to why fructose provides such unexpected results. Other reducing agents, whether organic or inorganic have not been found to provide the combined advantages of fructose of stabilization at relatively low levels and without cloying sweetness.
Glucose, a closely related sugar has been found to exhibit some fish oil stabilization activity. However, relative to fructose at the same levels, it is much less effective. Xylose has also been found to have some fish oil stabilization activity, but due to its cost, commercial availability ~nd low benefit activity level, is not a good subs.ltute for fructose.
In certain instances during development of the present invention, sucrose has ostensibly been shown to give some apparent fish oil stabilization benefits. Upon analysis, however, it is speculated that the appearance of benefits by sucrose derive in fact from fructose resulting from spontaneous hydrolysis or inversion of sucrose into glucose and fructose. Thus, sucrose per se is not believed to provide fish oil stabilization but, as surprisingly ciscovered, only by fructose.
Other useful food products containing fish oil and fructose are described in detail in our co-pending application entitled Food Products Containing Fish Oil Stabilized with Fructose (Canadian Patent Application Serial No. 577,057, Filed Sep. 9, 1988).
.,;
For many mixes it is accepted practice for the consumer to add the required amount of eggs to the mix in the course of batter preparation and this practice can be followed with the mixes of the invention. If desired, the inclusion of egg solids in the mix is an allowable alternative. The function and permissible variations in the remaining ingredients are apparent to those skilled in the art. For example, various amounts of ingredients such as flavors, colors, dry milk solids, water binders, e.g., a hydrophilic colloid such as carboxymethyl cellulose, salt and the like can be added if desired.
The culinary mixes including the fructose but excepting the fish oil are conventionally processed and blended to form a free flowing dry mix. For example, the mixes of this invention can be compounded by blending the flour, sugar, fructose, and shortening into a homogeneous premix in a ribbon blender, and then passing this premix through a hammermill to eliminate any lumps which may be formed. Any additional ingredients, e.g., egg solids, milk solids, nuts can then be added by mixing to form a free flowing mix. The prepared dry mix can then be conventionally pouched and/or packaged.
It is essential that, however, the fish oil is separately packaged from the other dry mix ingredients in a hermetically sealed, inert gas flushed, opaque container. The two pouches are conveniently placed together in a suitable container, e.g., cardboard box.
The present mixes prepared as described above are conveniently prepared into finished baked goods by admixing with water, and/or milk, and other optional ingredients, e.g., eggs, vegetable oil, to form a batter or dough, and baking or otherwise heating, e.g., frying, grilling or microwave heating.
Useful doughs and batters have the following moisture contents:
Moisture Content Baked Good Useful Preferred Biscuit 30-40% 35%
(American style) Cake 35-45% 38%
Brownie 14-25% 18%
Cookie 9-14% 12%
The finished baked good is characterized as its leaves the oven with a greatly less than expected development of a fishy flavor.
lS In the consumer setting, it is contemplated that consumption will quickly follow preparation.
The finished baked good can be allowed to stand prior to consumption but will stale, i.e., develop a fishy flavor, fairly quickly. After 24 hours at room temperature, the fishy flavor will become pronounced.
The fishy flavor is not harmful, merely profoundly unpalatable.
However, the finished baked goods can also be frozen and stored for periods adequate for frozen foods distribution. The frozen baked goods can be thawed by the consumer in conventional manner. The baked goods can also be refrigerated for modest improvements in shelf life.
Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest extent. The following preferred specific embodiments are, therefore, to be construed as merely illustrative and not limitative of the remainder of the disclosure whatsoever. It will be appreciated that other modifications of the present invention, -within the skill of those in the food arts, can be undertaken without departing from the spirit and scope of this invention.
Example 1 A mix for an oatmeal cookie is prepared having the following formulation:
Ingredient Weight %
Shortening 7.15 Fish oil 5.00 Brown sugar 8.40 High fructose corn syrup 5.00 Sucrose 7.20 Whole egg solids 8.60 Water 4.90 Vanilla 0.40 Quick oats 17.30 All purpose flour 20.00 Sodium bicarbonate 0.32 Raisins 15.00 Cinnamon 0.30 Salt 0 35 Nutmeg 0.10 Antioxidant blend 0.02 1 00 . 00%
1. Antioxidant blend consisting of 60%
tocopherol available from Henkel Corporation under the trade mark Covi-OX T70. 30% TBHQ mixture of (32% glycerol monolea.e, 30% corn oil, 20% TBHQ, 15% prophylene glycol and 3~ citric acid) available from Eastman Chemical Products Inc. under the trade mark TENOX 20A. 10~
partially hydrogenated soybean oil with BHA to help protect flavor available from Durkee Industrial Foods, under the trade mark Durkex 100.
Baked goods of comparable organoleptic attributes and fish oil stability are obtained when the high fructose corn syrup is replaced with other less pure fructose sources at equivalent fructose levels including 42 D.E. corn syrup.
A culinary mix of the present invention was prepared by blending in a dry mixer a blend of the dry ingredients and shortening of the above formulation. The culinary mix can comprise a first packet comprising this dry blend plus a second packet containing the fish oil.
The baked good was prepared by first forming a wet blend of the dry mix, fish oil and wet ingredients to form a thick batter and measuring out small quantities on a baking sheet and baking for about 10 minutes at 350 F. The resultant oatmeal cookies are characterized by good flavor immediately after baking.
Example 2 A chocolate cake baked good of the present invention was prepared according to the procedure of Example 1 having the following formulation:
Ingredient Weight %
Sucrose, fine grina 15.90 All purpose flour 16.85 Sucrose, regular grind 2.91 Starch, waxy maize 1.54 Sodium bicarbonate 0.40 Salt 0.45 Mono calcium phosphate 0.25 Red dutched cocoa 3.38 Gu~, carboxylmethyl cellulose 0.11 Xantham gum 0.08 Shortening 5.08 ~, -Eggs 13.20 Water 20.36 Soybean oil 4.74 Fish oil 4.74 Fruxtose 10.00 Antioxidant blendl 0.01 100 . 00%
1. Antioxidant blend consisting of 60%
tocopherol available from Henkel Corporation under the trade name J Covi-OX T70. 30% TBHQ mixture of (32%
glycerol monoleate, 30% corn oil, 20%
TBHQ, 15% prophylene glycol and 3% citric acid) available from Eastman Chemical Products Inc. under the trade name TENOX 20A. 10% partially hydrogenated soybean oil with BHA to help protect flavor available from Durkee Industrial JFoods, under the trade name Durkex 100.
Health benefits appear to be related to the presence of high levels of the n-3 family of polyunsaturated fatty acids. Oils containing such materials, such as fish oils, are referred to as "omega-3" oils and desirably contain high levels of n-3 fatty acids, especially eicosapentaenoic acid ("EPA") and docosahexaenoic acid ("DHA"). Such fatty acids are called "omega-3" since the first double bond occurs in the third carbon bond counting from the end or omega position of the fatty acid.
Notwithstanding the present interest in the health benefits of fish oil consumption, nonhydrogenated fish oil generally to date has not been widely used per se or as an ingredient in processed food products for use by humans due to notorious and severe problems in odor and flavor. However, gelatin capsules containing fish oil are available. Additionally, salmon oil has been added to canned salmon. Also, certain canned meat products have been marketed in Japan which have had refined fish oil added as a fortifier.
Hydrogenated fish oils are much more stable due to the decrease in the degree of polyunsaturation and are widely used in Europe for margarine. Hydrogenated fish oils have also been used in Scandinavian countries in other consumer products, e.g., finished cake.
(See also U.S. Patent Nos. 3,168,405, 3,268,337, 3,366,487) and margarine (see "Use of Fish Oils in Margarine and Shortening," Chapter 18, Fish Oils, Avi Publishing Co., Inc. 1968). Hydrogenation is also effective in reducing odor and flavor after deodorization. However, hydrogenation by decreasing polyunsaturation including the n-3 fatty acid component correspondingly decreases the health value of fish oil. Accordingly, it would be desirable to realize food products containing such nonhydrogenated fish oils, but the instability of the fish oil to date has prevented the development of such food products.
The principal approach taken in the art to utilize nonhydrogenated fish oil in processed foods generally has been to employ fish oils of enhanced stability. Two broad approaches have been taken in 3S the art to realize nonhydrogenated fish oils of enhanced stability. The first approach involves giving attention to the processing of the oil to achieve a cleaner, finished oil product. Particular attention has been given to the deodorization step in order to realize cleaner finished fish oil products.
In the second approach, the art has attempted to find adjuvants which can be added to finished fish oil to provide desired additional stability. For example, while the phenomenon of fish oil degradation is not completely understood, it is known, however, that oxidative rancidification is a contributing factor.
Addition of known antioxidants, singly as well as commercial mixtures, some allegedly synergistic, does result in some increase in stability. However, the instability of nonhydrogenated fish oils is so great, that even addition of such materials at maximum legally permitted levels provide only modest increases in stability.
Given the severe difficulties in realizing a suitable fish oil ingredient, it is understandable that comparatively little developmental effort has been made to formulate processed food products containing fish oil.
The prior art also includes U.S. Patent No. 4,357,362 (issued Nov. 2, 1982 to David Barker).
This patent discloses a pet food composition including fish material of reduced fishy odor by subjecting the composition in a sealed container, to sterilizing heat in the presence of a reducing agent. However, several disadvantages or limitations exist with this approach. First, the primary advantage is a fish odor reduction which is not necessarily directly related to the problems of fish oil flavor degradation. Second, a severe heat treatment in a sealed container is required in order to achieve the reduction in odor. It is 3~ undesirable for many foods to be subjected to such severe heat treatment. Third, fish flesh or fish -proteinaceous material is known to have a material effect on stability. However, most food products cannot contain fish flesh as a practical matter, e.g., mayonnaise, yet could beneficially include fish oil were oil stability nonetheless obtained. Also, the product is less susceptible to oxidative rancidity since it is sealed. Finally, a wide variety of organic and inorganic reducing agents are taught as useful although reducing sugars are preferred.
Still another problem exists with the utilization of fish oil in baked goods which is peculiar to their method of preparation. Baked goods, of course, are prepared from batters by a baking step, typically as short as 6 minutes for cupcakes or muffins to as long as 40 minutes for larger layer cakes in a baking oven at 300 F to 400 F. Exposure of nonhydrogenated fish oil to oxygen in the presence of moisture at these elevated temperature conditions would quickly cause development in clean fish oils of a strong and unpalatable fishy flavor. Conventional layer cakes with added, very clean, antioxidant stabilized, nonhydrogenated deodorized fish oils exit the oven with an impalatable fish flavor.
Given the state of the art with regard to fish oil stabilization, there is a continuing need for the development of new and improved processed food products containing fish oil of improved stability.
Accordingly, it is an object of the present invention to provide food products containing nonhydrogenated fish oils which nonetheless exhibit improved stability against degradation in both flavor and odor.
It is an object of the present invention to provide culinary mixes for baked goods containing 3~ nonhydrogenated fish oil.
It is another object of the present invention to provide food products of enhanced stability which do not require heat sterilization.
Another object of the present invention is to provide food products containing fish oil which do not require fish meat.
Still another object of the present invention is to provide food products containing fish oil of enhanced stability against flavor degradation.
Another important object is to provide food products with water which contain fish oil yet nonetheless exhibit increased stability.
It has been surprisingly discovered that the above objectives can be realized and superior culinary mixes for baked goods and baked goods containing fish oils can be prepared by incorporation of modest amounts of fructose. Surprisingly, fructose alone among sugars and other materials appears to be unexpectedly superior in providing the desired stabilization benefits.
SUMM~RY OF THE INVENTION
The present invention relates to culinary mixes for products prepared from batters and doughs containing fish oils of enhanced stability and to the baked goods themselves. In addition to common culinary mix ingredients of flour, shortening and leavening, the present compositions further essentially comprise finished deodorized, nonhydrogenated fish oils stabilized with minor amounts of fructose. The fish oiis also essentially include the maximum permitted levels of TBHQ and also contain tocopherol. The present invention further provides finished baked goods containing fish oil.
. ~
Accordingly, in one aspect, the present invention relates to a two part culinary mix comprising:
1. a first portion separately packaged and comprising a dry mix blend containing a farinaceous material, shortening and leavening and a fructose component in the amount of about 0.1% to 30% by weight of said culinary mix, and 2. a second portion separately packaged and hermetically sealed containing a nonhydrogenated refined, deoderized fish oil in the amount of about 0.1% to 18% by weight of said culinary mix, said fish oil containing, a. about 100 to 300 ppm of an antioxidant selected from the group consisting of tertiary butyl hydroquinone, butylated hydroxyanisole, butylated hydroxytoluene and mixtures thereof, b. about 1 to 2000 ppm of tocopherol.
In a further aspect, the present invention relates to a batter for a baked good comprising water and a culinary mix including a farinaceous material, shortening and leavening, additionally comprising, 1. about 0.1% to 18% by weight of the culinary mix being a nonhydrogenated refined, deodorized fish oil said fish oil containing, - 5a -a. about 100 to 300 ppm of an antioxidant selected from the group consisting of tertiary butyl hydroquinone, butylated hydroxyanisole, butylated hydroxytoluene and mixtures thereof, b. about 1 to 2000 ppm of tocopherol, and 2. about 0.1% to 30% by weight of the culinary mix being fructose and wherein the weight ratio of fructose to fish oil is at least about 10:100.
DETAILED DESCRIPTION OF THE INVENTION
The present invention resides in culinary mixes for products prepared from batters and doughs, - 5b -especially baked goods and to the finished goods themselves containing nonhydrogenated fish oil but which are substantially free of fish flesh. Nonetheless, the present finished goods are characterized by enhanced oil stability by virtue of the incorporation of minor amounts of fructose relative to similar compositions but not containing the requisite fructose amounts.
In its method aspect, the present invention resides in methods for fish oil fortification of finished and baked goods.
Throughout the specification and claims, percentages are by weight and temperatures in degrees Fahrenheit, unless otherwise indicated.
The present invention resides in part in the surprising discovery that otherwise conventional finished farinaceous goods, especially baked goods, and culinary mixes therefor can be prepared that include modest levels of nonhydrogenated, refined, deodorized and stabilized fish oil in partial substitution for other conventional shortening components so long as the goods also meet both of two conditions: first, that the goods include fructose within specified levels;
and second, that the fish oil also essentially includes the maximum permitted levels of selected antioxidants.
In another aspect, the present invention resides in the discovery that a specific combination of antioxidants, namely, TBHQ and tocopherol, provide unexpected superiority when used in combination with fructose for fish oil stabilization in farinaceous goods.
Among all antioxidants or combinations thereof, the combination of TBHQ at its maximum permitted levels plus tocopherol gives surprising fish oil stability benefits compared to other antioxidants or combinations thereof.
Culinary mixes for farinaceous goods to be prepared from batters and doughs are, of course, -well known and the skilled artisan will have no problem selecting specific ingredients and their concentrations formulated to prepare specific baked or finished goods and flavors. Indeed, the art is replete with such formulations. (See, for example, U.S. Patent Nos. 3,708,309 issued Jan. 2, 1973 to Johnson et al.;
3,694,229 issued Sep. 26, 1972 to Norsby et al.; 3,366,487 issued Sep. 29, 1969 to Hatton et al. Culinary mixes typically comprise flour or a farinaceous material, (occasionally corn flour) as the base or principal ingredient, plus shortening (with emulsifiers) and chemical leavening. Typically, for most but not all baked goods, the culinary mixes additionally essentially comprise a nutritive carbo~ydrate sweetening agent(s) which is typically sucrose and occasionally mixtures of sucrose with other`sweeteners.
The term "baked goods" and the culinary mixes therefor is meant to be broadly construed and to include, for example, layer cakes, pound cakes, brownies, muffins, cupcakes, cookies, coffee cakes, bundt cakes and biscuits. Although not literally a "baked good" since they are not baked, pancakes and waffles are also meant to be included since they are similar in formulation.
Exemplary culinary mix formulations are given below.
Flour Sugar Shor'ening Leavening Layer cakes and cupcakes 41 45 6-12 1-2 Muffins 50 25 10-15 2-3 Cookies 20-30 40-50 15-25 .5-1.0 Biscuits 80 10-18 15-20 2-3.5 Brownies 25-30 25 13-14 .1-.2 Still another essential ingredient of the instant, improved com~ositions is a refined, deodorized, nonhydrogenated, stabilized fish oil. The present food products provide convenient vehicles for delivery for consumption of fish oil to obtain the desirable special nutritional advantages provided by fish oil.
The fish oil is used in partial substitution for the conventional shortening ingredient. Desirably, the fish oils comprise from about 0.1~ to 18%, preferably about 4% to 12% of the culinary mixes. The finished baked goods should comprise about 2% to 10% fish oil, preferably about 4% to 8%. The modest differences in the upper values for the fish oil concentrations of the culinary mixes is due to the additional moisture or added solids typically added to the culinary mixes to form batters in baked goods preparation less the minor moisture losses occa~ioned during baking.
Fish oils are staples of commerce and their general processing is`well known (see, for example, Fish Oils: Their Chemistry, Technology, Stability, Nutritional Properties, and Uses, ed. by M. E. Stansby, The Avi Publishing Company, Inc. 1967. Especially use~ul for their therapeutic value herein are oils having a total n-3 fatty acid content of greater than about 20% such as are derived from menhaden oil, herring, capelin, anchovy, cod liver, salmon oil, sardine oil and mixtures thereof. Especially prefered for use herein is menhaden oil due to such supply considerations as cost and availability as well as its nutritional quality as being high in omega-3 fats. Recently, fish oil has been sold in gelatin capsules as a good supplement. However, in the present invention the fish oils are essentially also conventionally processed, e.g., refined and deodorized, t-o provide what is referred to in the art as a "finlshed"
oil. Unlike vegetable oils, however, fish oils typically do not require degumming. Also, conventional ,~' ~
hydrogenation of the fish oil such as is done to make the oil suitable for use for the preparation of margarine-is to be strictly avoided.
The present fish oils must be stabilized, i.e., will essentially include conventional oil stabilizing or materials at their maximum permitted levels (e.g., 200 ppm of total oil) such as antioxidants selected from the group consisting of TB~Q, (tertiary butyl hydroquinone) BHA (butylated hydroxyanisole) or BHT (butylated hydroxytoluene). Not all food approved antioxidants have been shown to be useful.
For example, the use of lecithin has actually been shown to aggravate development of fishy flavors.
Even more preferred products further include 1 to 2000 ppm tocopherol in addition to the antioxidant(s).
Surprisingly, the combination of T~HQ and tocopherol has unexpectedly been found to be superior to other antioxidants generally considered to be equivalents or substitutes. Thus, TB~Q is the antioxidant of choice. Still mo,e preferred products include 10 to 100 ppm (based on total oil) of a chelating agent desirably selected from the group consisting of citric acid, phytic acid, ethylene diamine tetra acetate and mixtures thereof. The food products can also beneficially include about 0.1% to 3~ of the fish oil of an oil soluble flavor masking agent based upon the weight of fish oil.
Preferred flavor masking agents include citrus oils, especially lemon oil.
Preferably, the fish oils useful herein are "Process for Simultaneous ~eodorization and Cholesterol Reduction of Fats and Oils" (Canadian Patent Application Serial No. 549,905, filed Oct. 21, 1987 to Marschner et al). The process there disclosed involves a process involving deaerating fish oil, mixing the oil with steam, heating, flash vaporization, thin ~ 4 _ 9 -film stripping with counter current steam (all steps being performed under vacuum). The finished fish oil prepared according to this method is additionally characterized both by reduced cholesterol (generally at cholesterol levels of less than about 400 mg/g, preferably less than about 250 mg/g) and enhanced stability by enhanced initial quality.
It is essential that the present culinary mixes and baked goods containing fish oil also contain fructose in order to realize the oil stability advantages discovered herein. Of course, fructose has been taught as useful for addition to culinary mixes at varying levels in substitution for conventional sucrose.
It is essential, however, that present food compositions comprise fructose such that the weight ratio of fructose to fish oil is at least about 5 to 30:100. Insufficient fructose can result in rapid deterioration of quality of the food product. As the oil degrades, the resultant fishy flavor and aroma increases rendering the food product increasingly unpalatable. ~xcessive fructose levels can result in products characterized by undesirable sweetness without obtaining proportional increases in oil stability, if any. Better results in terms of obtaining oil stabilization benefits without excessive sweetness are obtained when the food compositions contain fructose to oil in a ratio of at least 10:100. Best results are obtained when the food products contain fructose to oil in a ratio of at least 20:100.
The fructose can be provided from both relatively pure and less pure sources. r~hile pure crystalline fructose of various types and sources are commercially available, fructose in the form of high fructose corn syrup is practical from both a source availability and cost fructose corn syrup functions not only to provide the essential fructose -fish oil stabilizer, but also functions as a sweetener.
Less preferred but nonetheless useful herein are - less pure sources of fructose, e.g., corn syrup, honey, maple syrup solids, fruit juice solids and the like.
Surprisingly, only fructose has been found to provide the high stabilization benefits of the present invention at the concentrations taught as essential herein and no satisfactory explanation can be set forward as to why fructose provides such unexpected results. Other reducing agents, whether organic or inorganic have not been found to provide the combined advantages of fructose of stabilization at relatively low levels and without cloying sweetness.
Glucose, a closely related sugar has been found to exhibit some fish oil stabilization activity. However, relative to fructose at the same levels, it is much less effective. Xylose has also been found to have some fish oil stabilization activity, but due to its cost, commercial availability ~nd low benefit activity level, is not a good subs.ltute for fructose.
In certain instances during development of the present invention, sucrose has ostensibly been shown to give some apparent fish oil stabilization benefits. Upon analysis, however, it is speculated that the appearance of benefits by sucrose derive in fact from fructose resulting from spontaneous hydrolysis or inversion of sucrose into glucose and fructose. Thus, sucrose per se is not believed to provide fish oil stabilization but, as surprisingly ciscovered, only by fructose.
Other useful food products containing fish oil and fructose are described in detail in our co-pending application entitled Food Products Containing Fish Oil Stabilized with Fructose (Canadian Patent Application Serial No. 577,057, Filed Sep. 9, 1988).
.,;
For many mixes it is accepted practice for the consumer to add the required amount of eggs to the mix in the course of batter preparation and this practice can be followed with the mixes of the invention. If desired, the inclusion of egg solids in the mix is an allowable alternative. The function and permissible variations in the remaining ingredients are apparent to those skilled in the art. For example, various amounts of ingredients such as flavors, colors, dry milk solids, water binders, e.g., a hydrophilic colloid such as carboxymethyl cellulose, salt and the like can be added if desired.
The culinary mixes including the fructose but excepting the fish oil are conventionally processed and blended to form a free flowing dry mix. For example, the mixes of this invention can be compounded by blending the flour, sugar, fructose, and shortening into a homogeneous premix in a ribbon blender, and then passing this premix through a hammermill to eliminate any lumps which may be formed. Any additional ingredients, e.g., egg solids, milk solids, nuts can then be added by mixing to form a free flowing mix. The prepared dry mix can then be conventionally pouched and/or packaged.
It is essential that, however, the fish oil is separately packaged from the other dry mix ingredients in a hermetically sealed, inert gas flushed, opaque container. The two pouches are conveniently placed together in a suitable container, e.g., cardboard box.
The present mixes prepared as described above are conveniently prepared into finished baked goods by admixing with water, and/or milk, and other optional ingredients, e.g., eggs, vegetable oil, to form a batter or dough, and baking or otherwise heating, e.g., frying, grilling or microwave heating.
Useful doughs and batters have the following moisture contents:
Moisture Content Baked Good Useful Preferred Biscuit 30-40% 35%
(American style) Cake 35-45% 38%
Brownie 14-25% 18%
Cookie 9-14% 12%
The finished baked good is characterized as its leaves the oven with a greatly less than expected development of a fishy flavor.
lS In the consumer setting, it is contemplated that consumption will quickly follow preparation.
The finished baked good can be allowed to stand prior to consumption but will stale, i.e., develop a fishy flavor, fairly quickly. After 24 hours at room temperature, the fishy flavor will become pronounced.
The fishy flavor is not harmful, merely profoundly unpalatable.
However, the finished baked goods can also be frozen and stored for periods adequate for frozen foods distribution. The frozen baked goods can be thawed by the consumer in conventional manner. The baked goods can also be refrigerated for modest improvements in shelf life.
Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest extent. The following preferred specific embodiments are, therefore, to be construed as merely illustrative and not limitative of the remainder of the disclosure whatsoever. It will be appreciated that other modifications of the present invention, -within the skill of those in the food arts, can be undertaken without departing from the spirit and scope of this invention.
Example 1 A mix for an oatmeal cookie is prepared having the following formulation:
Ingredient Weight %
Shortening 7.15 Fish oil 5.00 Brown sugar 8.40 High fructose corn syrup 5.00 Sucrose 7.20 Whole egg solids 8.60 Water 4.90 Vanilla 0.40 Quick oats 17.30 All purpose flour 20.00 Sodium bicarbonate 0.32 Raisins 15.00 Cinnamon 0.30 Salt 0 35 Nutmeg 0.10 Antioxidant blend 0.02 1 00 . 00%
1. Antioxidant blend consisting of 60%
tocopherol available from Henkel Corporation under the trade mark Covi-OX T70. 30% TBHQ mixture of (32% glycerol monolea.e, 30% corn oil, 20% TBHQ, 15% prophylene glycol and 3~ citric acid) available from Eastman Chemical Products Inc. under the trade mark TENOX 20A. 10~
partially hydrogenated soybean oil with BHA to help protect flavor available from Durkee Industrial Foods, under the trade mark Durkex 100.
Baked goods of comparable organoleptic attributes and fish oil stability are obtained when the high fructose corn syrup is replaced with other less pure fructose sources at equivalent fructose levels including 42 D.E. corn syrup.
A culinary mix of the present invention was prepared by blending in a dry mixer a blend of the dry ingredients and shortening of the above formulation. The culinary mix can comprise a first packet comprising this dry blend plus a second packet containing the fish oil.
The baked good was prepared by first forming a wet blend of the dry mix, fish oil and wet ingredients to form a thick batter and measuring out small quantities on a baking sheet and baking for about 10 minutes at 350 F. The resultant oatmeal cookies are characterized by good flavor immediately after baking.
Example 2 A chocolate cake baked good of the present invention was prepared according to the procedure of Example 1 having the following formulation:
Ingredient Weight %
Sucrose, fine grina 15.90 All purpose flour 16.85 Sucrose, regular grind 2.91 Starch, waxy maize 1.54 Sodium bicarbonate 0.40 Salt 0.45 Mono calcium phosphate 0.25 Red dutched cocoa 3.38 Gu~, carboxylmethyl cellulose 0.11 Xantham gum 0.08 Shortening 5.08 ~, -Eggs 13.20 Water 20.36 Soybean oil 4.74 Fish oil 4.74 Fruxtose 10.00 Antioxidant blendl 0.01 100 . 00%
1. Antioxidant blend consisting of 60%
tocopherol available from Henkel Corporation under the trade name J Covi-OX T70. 30% TBHQ mixture of (32%
glycerol monoleate, 30% corn oil, 20%
TBHQ, 15% prophylene glycol and 3% citric acid) available from Eastman Chemical Products Inc. under the trade name TENOX 20A. 10% partially hydrogenated soybean oil with BHA to help protect flavor available from Durkee Industrial JFoods, under the trade name Durkex 100.
Claims (12)
1. A two part culinary mix comprising:
1. a first portion separately packaged and comprising a dry mix blend containing a farinaceous material, shortening and leavening and a fructose component in the amount of about 0.1% to 30% by weight of said culinary mix, and
1. a first portion separately packaged and comprising a dry mix blend containing a farinaceous material, shortening and leavening and a fructose component in the amount of about 0.1% to 30% by weight of said culinary mix, and
2. a second portion separately packaged and hermetically sealed containing a nonhydrogenated refined, deoderized fish oil in the amount of about 0.1% to 18% by weight of said culinary mix, said fish oil containing, a. about 100 to 300 ppm of an antioxidant selected from the group consisting of tertiary butyl hydroquinone, butylated hydroxyanisole, butylated hydroxytoluene and mixtures thereof, b. about 1 to 2000 ppm of tocopherol.
2. The culinary mix of Claim 1 additionally comprising sugar, other than fructose.
2. The culinary mix of Claim 1 additionally comprising sugar, other than fructose.
3. The culinary mix of Claim 1 wherein the fish oil additionally comprises a chelating agent.
4. The culinary mix of Claim 1 wherein the fructose comprises about 0.1% to 20% by weight.
5. A batter for a baked good comprising water and a culinary mix including a farinaceous material, shortening and leavening, additionally comprising, 1. about 0.1% to 18% by weight of the culinary mix being a nonhydrogenated refined, deodorized fish oil said fish oil containing, a. about 100 to 300 ppm of an antioxidant selected from the group consisting of tertiary butyl hydroquinone, butylated hydroxyanisole, butylated hydroxytoluene and mixtures thereof, b. about 1 to 2000 ppm of tocopherol, and 2. about 0.1% to 30% by weight of the culinary mix being fructose and wherein the weight ratio of fructose to fish oil is at least about 10:100.
6. The batter of Claim 5 additionally comprising sugar other than fructose and wherein the fish oil additionally comprises a chelating agent.
7. The batter of Claim 5 wherein the fructose comprises about 0.1% to 20% by weight of the culinary mix.
8. A chemically leavened baked good comprising farinaceous material, shortening, leavening and moisture, additionally comprising, 1. about 0.1% to 10% by weight of the baked good being a nonhydrogenated refined, deodorized fish oil said fish oil containing, a. about 100 to 300 ppm of an antioxidant selected from the group consisting of tertiary butyl hydroquinone, butylated hydroxyanisole, butylated hydroxytoluene and mixtures thereof, b. about 1 to 2000 ppm tocopherol, and 2. about 0.1% to 30% by weight of the baked good being fructose, and wherein the weight ratio of fructose to fish oil is at least about 10:100.
9. The baked good of Claim 8 additionally comprising sugar.
10. The baked good of Claim 8 wherein the fish oil additionally comprises a chelating agent.
11. The baked good of Claim 8 wherein the fructose comprises about 0.1% to 20% by weight.
12. The culinary mix of any one of claims 1 to 4 wherein the weight ratio of fructose to fish oil is at least about 5:100.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14852088A | 1988-01-26 | 1988-01-26 | |
| US148,520 | 1988-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1337854C true CA1337854C (en) | 1996-01-02 |
Family
ID=22526119
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 589109 Expired - Fee Related CA1337854C (en) | 1988-01-26 | 1989-01-25 | Culinary mixes for products prepared from batters and doughs with fish oils stabilized with fructose |
Country Status (3)
| Country | Link |
|---|---|
| AU (1) | AU3053989A (en) |
| CA (1) | CA1337854C (en) |
| WO (1) | WO1989006906A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT201600128070A1 (en) * | 2016-12-19 | 2018-06-19 | Alghea Biomarine S R L | MIXTURE FOR FOOD PRODUCTS ENRICHED WITH INSATURE FATTY ACIDS |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4963385A (en) * | 1989-06-02 | 1990-10-16 | Nabisco Brands, Inc. | Stabilized emulsions containing highly unsaturated oils |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3170796A (en) * | 1962-07-17 | 1965-02-23 | Procter & Gamble | Packaged culinary mix for preparing rich baked goods |
| US4396635A (en) * | 1978-12-26 | 1983-08-02 | The Procter & Gamble Co. | Microwave cake mix |
| JPS5675066A (en) * | 1979-11-24 | 1981-06-20 | Lion Corp | Production of fried food |
| US4456626A (en) * | 1982-03-17 | 1984-06-26 | The Procter & Gamble Company | New shortening system |
| US4419377A (en) * | 1982-03-22 | 1983-12-06 | The Procter & Gamble Company | Cake mix containing a lipophilic emulsifier system |
| US4504510A (en) * | 1982-05-28 | 1985-03-12 | Stauffer Chemical Company | Method of preparing freeze-thaw and refrigerator stable pancake batter and product thereof |
-
1989
- 1989-01-25 AU AU30539/89A patent/AU3053989A/en not_active Abandoned
- 1989-01-25 WO PCT/US1989/000303 patent/WO1989006906A1/en unknown
- 1989-01-25 CA CA 589109 patent/CA1337854C/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT201600128070A1 (en) * | 2016-12-19 | 2018-06-19 | Alghea Biomarine S R L | MIXTURE FOR FOOD PRODUCTS ENRICHED WITH INSATURE FATTY ACIDS |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1989006906A1 (en) | 1989-08-10 |
| AU3053989A (en) | 1989-08-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4120986A (en) | Whole egg replacer | |
| US4913921A (en) | Food products containing fish oils stabilized with fructose | |
| TWI244375B (en) | Oil composition and food, feed, pharmaceutical cooking oil comprising thereof | |
| JP4995377B2 (en) | Oil composition | |
| US6224925B1 (en) | Shelf stable brownie batter article and method of preparation | |
| US6391366B1 (en) | Soft frozen batter for baked goods and method of preparation | |
| US20100092617A1 (en) | Compositions comprising polyunsaturated fatty acids | |
| EP0053844A1 (en) | A dipeptide sweetening composition | |
| US5084294A (en) | Culinary mixes for products prepared from batters and doughs with fish oils stabilized with fructose | |
| EP0571219B1 (en) | Esterified propoxylated glycerin fat substitute compositions resistant to gastrointestinal side effects | |
| CN103384473A (en) | Dough products comprising ethylcellulose and exhibiting reduced oil migration | |
| US5955123A (en) | Baked compositions comprising psyllium | |
| US4798733A (en) | Yeast-fermented food modifier | |
| US4608267A (en) | Lecithin-containing food product | |
| JPWO2018037926A1 (en) | Sweetener and / or salt enhancer | |
| JPH07503618A (en) | Butter cookies with a perceptible cooling sensation | |
| CA1337854C (en) | Culinary mixes for products prepared from batters and doughs with fish oils stabilized with fructose | |
| EP0707448A1 (en) | Low fat, low calorie fat substitute | |
| JPH06189666A (en) | Sweet baked article containing potato fiber | |
| US3845221A (en) | Hickory smoked french barbecue bakery products | |
| JP3519391B2 (en) | Oil foods for French toast | |
| JP3762889B2 (en) | Deep-fried rice cake and method for producing deep-fried rice cake | |
| JP7246878B2 (en) | bakery dough and bakery food | |
| JPH0561896B2 (en) | ||
| JP2006271289A (en) | Filling material for baking |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKLA | Lapsed |