WO1991003944A1

WO1991003944A1 - Reduced calorie triglycerides in foods

Info

Publication number: WO1991003944A1
Application number: PCT/US1990/005306
Authority: WO
Inventors: Peter S. Givens, Jr.; Edward L. Wheeler; Ronald P. D'amelia; Michael S. Otterburn; Gilbert A. Leveille; John W. Finley; Lawrence P. Klemann
Original assignee: Nabisco Brands, Inc.
Priority date: 1989-09-20
Filing date: 1990-09-18
Publication date: 1991-04-04
Also published as: AU6509090A; EP0445278A4; CA2042057A1; EP0445278A1; JPH04501812A

Abstract

Triglycerides are esterified at the 1- and 3- positions with saturated, long chain fatty acids, such as stearic, and at the 2- position with a short chain acid, such as acetic. These triglycerides provide fewer calories than those triglycerides commonly present in foods. Food compositions which are lower in calories than the original compositions can thus be produced by replacing some or all of the fat with this type of triglyceride.

Description

REDUCED CALORIE TRIGLYCERIDES IN FOODS

Inventors: John Westcott Finley residing at 3 Oldstone

Lane, Whippany, 07981, Lawrence Paul Klemann residing at 196 Tanglewood Drive, Somerville, 08876, Gilbert Antonio Leveille residing at 23 Cambridge Avenue, Denvilie, 07834, Michael Storey Otterburn residing at 1145 Sussex Turnpike, Randolph, 07896, Edward Loren Wheeler residing at 7 Redwood Drive, Falrfield, 07006, all of New Jersey, Peter Slmmonds Given, Jr. residing at 508 Hazel Street, Glencoe, Illinois, 60022, and Ronald Philip D'Amelia residing at 1 Fox Place, Hicksville, New York 11801.

BACKGROUND OF INVENTION

This invention pertains to the use of a new type of natural triglyceride in food compositions to yield a product lower in calories. These triglycerides strategically position saturated, long chain fatty acids and a short chain acid to achieve the desired balance of caloric availability and functional properties.

It has been reported that fats make up 40% to 45% of the calories in the average American diet with triglycerides constituting about 90% of the total edible fats consumed. Fats provide approximately nine calories per gram compared to approximately four calories per gram for proteins and carbohydrates. Thus, major research efforts have been conducted toward the reduction of caloric intake for health or medical reasons without sacrificing the functional and organoleptic properties of fat.

One strategy for developing reduced calorie replacement fats has been to structurally re-engineer natural triglycerides in such a way as to retain their conventional functional properties in food compositions, while removing their susceptibility towards hydrolysis or subsequent absorption during lipid digestion. For example, the fatty acids attached to glycerol have been replaced with alternative acids (U.S. Patent Nos. 3,579,548, Whyte and 4,582,715, Volpenhein); groups have been inserted between the fatty acids and the glycerol backbone ("propoxyl ated glycerols" , European Patent Application No. 254,547, White and Pollard); the ester linkages have been replaced by ether linkages (U.S. Patent No. 3,818,089, Bayley and Carlson and Canadian Patent No. 1,106,681, Trost); the ester linkages have been reversed (U.S. Patent No. 4,508,746, Hamm); and the glycerol moiety had been replaced with an alternate alcohol (U.S. Patent Nos. 2,924,528, Barskey, et al. and 2,993,063, Alsop and Carr).

A second strategy for developing reduced calorie replacement fats has been to synthesize nonabsorbable polymeric materials structurally unlike triglycerides, but having physical properties similar to edible fats. Mineral oil was disclosed as early as 1894 (U.S. Patent No. 519,980, Winter) and, more recently, polydextrose (U.S. Patent No. 4,631,196, Zeller); polyglucose and polymaltose (U.S. Patent No. 3,876,794, Rennhard); polysiloxane (Eur. Patent Appl. No. 205,273, Frye); jojoba wax (W. Ger. Pat. No. 3,529,564, Anika); and polyethylene polymers (E. Ger. Patent No. 207,070, Mieth, et al. ) have been suggested.

A third strategy for developing reduced calorie replacement fats combines the first two. Rather than restructure triglyceride molecules or find a substitute which is structurally dissimilar, this approach uses various polyol esters, compounds which have numbers of fatty acid groups in excess of the three in conventional triglyceride fats, as nonabsorbable fat replacements. For example, fully esterified sugar alcohols (Lapworth and Pearson, and Halliburton, et al., 13 J. Biol. Chem. 296 and 301 (1919)); esterified pentaerythritol, a tetrahydric neopentyl sugar alcohol which can be formed from pentaerythrose (U.S. Patent No. 2,962,419, Minich); and amylose esters (U.S.D.A. Southern and Western Regional Research Laboratories, Booth and Gros, 40 J. Amer. Oil Chem. Soc. 551 (1963)) have been suggested. Sucrose polyesters, nondigestible mixtures of sucrose hexa-, hepta-, and octa- fatty acid esters have been suggested as low calorie replacements of edible fats and oils in food compositions (U.S. Patent Nos. 3,600,186, Mattson and Volpenhein, 4,446,165, Roberts, and 4,461,782, Roberts and Rodriguez). The caloric availability and digestibility of a series of dimeric and polymeric glycerides including diglyceride esters of succinic, fumaric, and adipic acids, and polymeric fats from stearic, oleic, and short-chained dibasic acids were assessed by the U.S.D.A. group supra, and polyglycerol esters have since been suggested (U.S. Patent Nos. 3,637,774, Babayan and Lehman and 3,968,169, Seiden and Martin).

Nondigestible or nonabsorbable triglyceride analogs, polyol esters, and polymeric materials have proven disappointing as fat replacements because, when tested in feeding trials, they caused gastrointestinal side effects, in some cases so extreme that frank anal leakage was observed (Hamm, 49 J. Food Sci. 419 (1984), Haumann, 63 J. Amer. Oil Chem. Soc. 278 (1986), and LaBarge, 42 Food Tech. 84 (1988)). To alleviate this problem, various hardened fats, notably hydrogenated palm oils and synthetic cocoa butters, have been employed as anti-anal leakage agents to be used with sucrose polyesters (U.S. Patent Nos. 4,005,195, Jandecek, 4,005,196, Jandecek and Mattson, and 4,461,782, Robbins and Rodriguez) and saturated residues have been incorporated into the polyester molecules (Eur. Patent Appl. Nos. 236,288, Bernhardt and 256,585, van der Plank and Rozendaal). The fatty acid moieties of polyglycerol esters can be catabolized if the aliphatic group of the fatty acid is short, but the polyglycerol itself is not metabolized (Michael and Coots, 20 Toxicol. Appl. Pharm. 334 (1971)), and its laxative effect is so pronounced that the compounds have been suggested for use as fecal softeners (U.S. Patent No. 3,495,010, Fossel).

Sucrose polyesters also interfere with cholesterol metabolism and vitamin A and vitamin E absorption (Aust, et al., 25 Ann. Nutr. Metab. 255 (1981); Glueck, et al., 32 Amer. J. Clin. Nutr. 1636 (1979); and Sletten, et al. 7 Acta Vitaminal Enzymol. 49 (1985)). Polyesters stimulate the excretion of steroids in the feces (Glueck, at al., 33 Amer. J. Clin. Nutr. 2177 (1980)) and interfere with the metabolism of lipophlHc toxins (Richter, et al., 40 Chem. Biol. Interact. 335 (1982)). In addition, some residual accumulation of nondigestible polyesters occurs in tissues, especially in fat tissue, though also in muscles and other organs. The accumulation increases with long-term digestion and the incorporated esters are not excreted even after the compounds are eliminated from the diet (Aust, et al., 26 Nahrung K3 (1982) and 30 Nahrung 453 (1986)). Some scientists have reported that high melting point fats are less digestible than those with low melting points: animal and vegetable fats with melting points lower than 50ºC are well absorbed and digested by normal men (Deuel, The Lipjds 214, (1955)); and lower melting point fats are more digestible in dogs (Suzuki 29 C.A. 3378 (1935)). When triglycerides are not melted during lipid digestion, they are normally excreted as solids. Fatty acids with high melting points also are less digestible than those with low melting points (Mattson, 69 J. Nutr. 338; and Hashim, et al. 31 Am. J. Clin. Nutr. S273 (1978)). Two ways of increasing the melting point of fatty acids are to increase the chain length and to decrease the degree of unsaturation (Hashim, et al., 31 Am. J. Clin. Nutr. S273 (1978)). Studies have also shown that branched chain fatty acids tend to have lower melting points and are less absorbable than straight chain fatty acids with the same number of carbon atoms.

Studies have also shown that straight chain, saturated fatty acids from C₄ to C₈ are completely digestible, from C₁₀ to C₁₆ are progressively less absorbable, and from C₁₈ and higher only slightly absorbed (Carroll, 64 J. Nutr. 399 (1958)). Other studies have further demonstrated that triglycerides having saturated fatty acids of eighteen carbons or longer are less digestible than shorter chain fatty acids and free fatty acids are absorbed less readily as they get longer: only 15% fully hydrogenated linseed oil was absorbed compared with 98% for safflower oil (Mattson 69 J. Nutr. 338 (1959)); higher saturated fatty acids are poorly absorbed even when fed as a mixture with unsaturated fats

(Rice 61 J. N u t r . 253 ( 1956 ) ) ; an d rat s f ed hyd rog e n a t ed s oybe an s p ray oil absorbed 30% while over 90% of the unsaturated oil was absorbed (Comai 108 J. Nutr. 826 (1977)).

Studies have further shown that the absorbability of fat is influenced by the positional distribution of certain fatty acids on the triglyceride: stearic acid is well absorbed by rats when esterified on the 2- position, but is poorly absorbed when on the 1- or 3- positions when oleic is esterified at the other positions (Mattson, et al., 109 J. Nutr. 1682 (1979)); and stearic and palmitic acids are better absorbed when situated at the 2- position of a triglyceride than at the 1- or 3- positions of naturally occurring fats commonly fed to infants (Tomerelli, et al., 95 J. Nutr. 583 (1968)).

Several studies have also demonstrated that an increase in dietary calcium or magnesium exerts an adverse effect on the absorption of fatty acids with high melting points (Cheng, et al. 37 J. Nutr. 237 (1949) and Tadayyon and Lutwak, 97 J. Nutr. 246 (1969)). It seems probable that, upon hydrolysis, these fatty acids form soaps and insoluble complexes which are not readily absorbed (Carroll and Richards, 64 J. Nutr. 411 (1958)). SUMMARY OF INVENTION

An object of the present invention is to provide a new class of reduced calorie, all natural triglycerides and food compositions containing these products. Another object of this invention is to provide a fat composition that is substantially reduced in calories when compared to conventional fat compositions. A further object of this invention is to provide a fat which is at least partially nondigestible, thus yielding substantially fewer calories than conventional fat. A further object of this invention is to provide a reduced calorie fat having excellent organoleptic properties so that it can be used in a wide variety of foods. A further object of this invention is to provide a reduced calorie fat having excellent functional properties, i.e. melting, crystallization, and flavor transfer, so that it can be used in a wide variety of foods.

These and other objects are accomplished according to the present invention which provides a new class of reduced calorie triglycerides derived from glycerol esterified with saturated, long chain fatty acids at the 1- and 3- positions and a short chain acid at the 2- position. The short chain acid may be either saturated or unsaturated, either straight or branched. The term natural, as used herein, means having the general characteristic structure of naturally occurring triglycerides, e.g. formed by the acid esterification of glycerol. The term long chain, as used herein, means that the fatty acid contains at least about sixteen carbons. The term short chain, as used herein, means that the acid contains no more than abou t ten carbons. Thus, the new class of triglycerides are represented by the following formula:

where, R and R" are long chain, saturated fatty acid residues containing between 16 and 40 carbons; and R' is a short chain acid residue containing between 2 and 10 carbons.

DETAILED DESCRIPTION OF THE INVENTION

Reduced calorie fats can contain fatty materials in addition to the triglycerides of this invention which have a short-chain acid at the 2- position and saturated, long chain fatty acids at the 1- and 3- positions. The triglycerides may be a pure composition consisting of only one triglyceride or a mixture of triglycerides. Where other fats are employed with these novel triglycerides, they should be of a type and in amounts compatible with the objects of this invention, primarily to reduce calories. Desirably, reduced calorie fats and edible foods of this invention will have predominant amounts of the novel triglycerides and, most usually, would contain at least 35%, and as much as 80% or higher of these triglycerides by weight.

The short chain acid should contain no more than about A carbons, preferably between 2 and 6 carbons, and more preferably between 2 and 4 carbons. This short chain may be either saturated or unsaturated, straight or branched. Among the suitable short chain acids are acetic, propionic, n-butyric, iso-butyric, caproic, caprylic, pelargonic, capric, glycolic, lactic, hydracrylic, hydroxybutyric, propenoic, butenoic, pentenoic, hexenoic, heptenoic, octenoic, nonenoic, decenoic, and the like.. This short chain acid will be selected primarily for the calories it delivers and its effect on melting characteristics. In some circumstances, its effects on other properties will also be of importance.

The long chain fatty acids should be fully saturated with carbon chains containing between about 16 and about 40 carbons, preferably between 16 and 24 carbons, and more preferably between 16 and 20 carbons. The long chain fatty acid at the 1- position may be either the same or different than that at the 3- position. Among the long chain fatty acids which can be employed are palmitic, stearic, arachidic, behenic, lignoceric, cerotic, montanic, and melissic, as well as other less frequently occurring fatty acids.

By using different combinations of acids, the triglycerides can be structured so as to obtain the desired functional characteristics, such as melting point, for a variety of different food compositions. For example, esterifying with palmitic acid at the 1- and 3- positions would likely give a triglyceride with a lower melting point than if esterifying with behenic acid, and would thus be more suitable for incorporation into a butterscotch flavored chip. By esterifying with propionic acid at the 2- position of a dipalmitin, a potentially monomorphic triglyceride is formed which has a higher degree of thermostability, a sharp melting point, and crystalline unity. This triglyceride would thus be appropriate in a food composition in which fat bloom is problematic, such as chocolate or the like coating.

Mixtures of fatty acids derived by the hydrolysis of natural fats can also be employed, such as those obtained from soybean, sunflower, peanut, safflower, olive, sesame, rice bran, canola, babassu, coconut, palm kernel, palm, rapeseed, cottonseed, corn, marine oil, or butter oil, or plant waxes such as jojoba. Specific fractions of these processed or unprocessed oils or waxes can also be employed to provide fatty acid residues with aliphatic groups which impart specific, desired properties in the fat. For example, low molecular weight fatty acids derived from butter oil are desirable for the dairy flavor and aroma they impart upon partial hydrolysis. Also, hydrogenated fatty acids can be fractionated to provide fatty acids for triglycerides which melt within a desirable temperature range, e.g., just below body temperature. These characteristics can also be obtained by combinations of the triglycerides of this invention with those naturally present or used in food compositions.

The new class of triglycerides are represented by the following formula:

where, R and R" are long chain, saturated fatty acid residues containing between 16 and 40 carbons, preferably between 16 and 24 carbons, and more preferably between 16 and 20 carbons; and

R' is a short chain acid residue containing between

2 and 10, preferably between 2 and 6 carbons, and more preferably between 2 and 4 carbons.

The following is a list of representative, but not limiting, examples of natural triglycerides of this invention:

The above examples and other triglycerides of this invention can be synthesized by tecnniques such as the direct or transesteriflcation of a selected 1,3-diglyceride (secondary alcohol). The synthesis of several specific tailored triglycerides have been published: glyceryl valproates have been synthesized for use as anti-convulsants (U.S. Patent No. 4,701,469, Marriott, et al.); tailored triglycerides with a polyunsaturated, long chain fatty acid at the 2- position and a saturated fatty acid between C₄ and C₁₈ at the 1- and 3- positions have been synthesized for use as therapeutic compositions (U.S. Patent Nos. 4,607,052, 4,701,469, and 4,701,470, Mendy, et al.); and triglycerides with at least 30% of a particular combination of a saturated, medium chain fatty acid, C_6:0, C_8:0, or C_10:0, a saturated, long chain fatty acid, and a unsaturated long chain fatty acid have been synthesized for their improved autoignition characteristics in shortenings and cooking oils (U. S. Patent No. 4,832,975, Yang).

The direct esteri fication reaction can be performed by reacting the 2-hydroxyl 1,3-diglyceride with the appropriate fatty acid, acid chloride, or acid anhydride. In the reaction between the acyl halide and the 1,3-diglyceride, pyridine or another type of base can be used to neutralize the hydrochloric acid by-product. The direct esterification of the 1,3-diglyceride with the appropriate acid anhydride was found to be a preferred method for the preparation of the triglyceride esters of this invention.

The choice of fatty add moieties will affect the biological as well as the physical properties of the composition. Where these fatty acid moieties are metabolized, the caloric value of the compound will increase. Preferred compounds are partially digestible and deliver 0.5 to 8.5 kcal/gram, preferably 0.5 to 6.0 kcal/gram, and more narrowly 1.0 to 5.0 kcal/gram upon being metabolized.

The triglycerides of this invention may be incorporated alone or in combination with another fat and/or fat substitute into any food composition or used in conjunction with any edible material. The term "edible material" is broad and includes anything edible whether or not intended for nutrition, i.e., it can be an additive such as an antioxidant for fats or oils, an anti-spatter agent, an emulsifier, a texture modifier such as a plasticizer for chewing gum, a component for cosmetics, or other functional ingredient such as a carrier or diluent for use in flavorings, pharmaceuticals, and the like. Representative of edible materials which can contain the fat of this invention in full or partial replacement of the currently used fat are: frozen deserts, i.e., sherbert, ice cream, ices, or milkshakes; puddings and pie fillings; margarine and margarine blends; flavored bread and biscuit spreads; mayonnaise; salad dressings; filled dairy products such as filled cream or milk; dairy or non-dairy cheese spreads; peanut butter spreads; coffee lighteners, liquid and dried; flavored dips; frying oils and fats; spray or topical oil; reformed and comminuted meats; meat substitutes and extenders; whipped toppings; compound coatings; frostings; confectionery coatings and fillings; cocoa butter replacements or blends; candy, especially fatty candies such as those containing peanut butter or chocolate; chewing gum; bakery products, i.e., cakes, breads, rolls, pastries, cookies, biscuits, and savory crackers; mixes or ingredient premixes for any of these; nuts, including peanuts; snack foods, extruded and baked, corn, wheat, and rice; topical oils; as well as flavor, nutrient, drug, or functional additive delivery systems.

EXAMPLES

The following examples are presented to further illustrate and explain the present invention and should not be taken as limiting in any regard. Unless otherwise indicated, all parts and percentages are by weight, and are based on the weight at the particular stage of the process being described.

Example 1

The reduced calorie triglyceride fat, 2-acetyl-1,3-distearin is prepared in this example.

One gram of 99% pure 1,3-distearin, commercially available by known techniques, is weighed out and placed into a 100 ml round-bottomed flask. A magnetic stir bar is also placed in the flask. An excess (15 ml) of acetic anhydride is added and the reflux condenser is attached to the flask. The system is heated by means of a heating mantle controlled by a voltage regulator until the mixture reaches reflux. The mixture is then refluxed for three hours with constant stirring. Heat is next removed and the mixture is cooled to ambient temperature. The mixture is then transferred into a separatory funnel with the aid of 75 ml diethyl ether.

The solution is washed alternatively with 10% sodium bicarbonate and water until it is neutral to litmus. Finally, the sample is dried at 90ºC for one hour. The capillary melting point of this compound was approximately 59ºC. This procedure was repeated using the appropriate diglycerides and anhydrides to produce the following compounds:

(1) 2-acetyl 1,3-distearin

(Melting point approximately 59ºC)

(2) 2-acetyl 1,3-dipalmitin

(Melting point approximately 53ºC)

(3) 2-propionyl 1,3-distearin

(Melting point approximately 52ºC)

(4) 2-propionyl 1,3-dipalmitin

(Melting point approximately 45ºC)

(5) 2-butyryl 1,3-distearin

(Melting point approximately 51ºC)

(6) 2-butyryl 1,3-dipalmitin

(Melting point approximately 40ºC)

(7) 2-isobutyryl 1,3-distearin

(Melting point approximately 47ºC)

(8) 2-isobutyryl 1,3-dipalmitin

(Melting point approximately 38ºC) EXAMPLE 2

Sweet Chocolate. A reduced calorie sweet chocolate flavored comestible may be prepared by combining:

Ingredient Parts

Cocoa Powder 0.5

Sugar 1.5

To this is added approximately 95% of

2 butyryl-1,3-dipalmitin 1.0 and the ingredients are mixed thoroughly and passed through a refiner to reduce the particles to desired size. The material is conched and the remaining 2-butyryl 1,3-dipalmitin is added. The mixture is then tempered, poured into molds and quench cooled.

EXAMPLE 3

Chocolate Chips. The chocolate prepared above may be melted and deposited into drops in the usual process. EXAMPLE 4

Sugar Cookies. Sugar cookies may be prepared by blending:

Ingredient Parts

Sugar 231

2-propionyl 1,3-distearin 57

Corn Oil 57

Salt 3.7

Sodium Bicarbonate 4.4

Water 37.4

5.9% Dextrose Solution (wt/wt) 58.7

Flour 391

All of the ingredients are creamed together. The dough so formed may be extruded (the dough is very tacky) and baked by the usual process. EXAMPLE 5

Margarine. Margarine may be prepared by combining the ingredients for the following two phases:

Oil Phase Ingredients Parts

2-propionyl 1,3-dipalmitin 15.0

2-butyryl 1,3-dipalmitin 15.0

Corn Oil 29.0

Soybean Hardstock (IV 65) 40.0

Emulsifier 1.0

Aqueous Phase Ingredients

Water 95.8

Milk Solids 2.0

Salt 2.0

Citric Acid 0.1

Beta Carotene 0.1 The phases are emulsified in an oil:aqueous phase ratio of 80:20, and passed through a cool scraped surface heat exchanger in the usual process.

EXAMPLE 6

Flavor Bits. Flavor bits for incorporation into baked goods may be prepared by combining the following ingredients:

Ingredient Parts

Sucrose 215

Water 180

Corn Syrup 160

Example 5 Margarine 28

Flavor 12

Citric Acid 10

Glycerin 8

Salt 5

Dye 1 The first three ingredients are heated to 290ºF. and the heat removed. Margarine is mixed in, and the mixture allowed to cool to 160-170ºF. before adding the remaining ingredients. (Almost any flavoring material may be used as flavor, for example, butterscotch or peanut or other nut.) The mixture is then poured into a cold aluminum pan and frozen in dry ice. The frozen mixture is then cracked and milled into bits.

EXAMPLE 7

Butterscotch Cookies Butterscotch cookies may be prepared by blending:

Ingredient Parts

Flour 22.0

2-acetyl 1,3-distearin 5.0

2-propionyl 1,3-distearin 5.0

Corn Oil 10.0

Salt 0.7

Sodium Bicarbonate 0.1 Monocalcium Phosphate 0.1

Vanillin 0.1

Water 8.0 and mixing well. To this is added

Sugar 30.0 which is mixed until dispersed. Then

Example 6 Butterscotch bits 19.0 are mixed in until just blended prior to depositing and baking by the usual process.

EXAMPLE 8

Vanilla Wafers. To prepare vanilla wafers, blend

Ingredient Parts

2-acetyl 1,3-distearin 6

2-propionyl 1,3-distearin 6 Corn Oil 13

Flour 100

Granulated Sugar 72

High Fructose Corn Syrup 5.0

Nonfat Dry Milk 1.0

Salt 1.0

Ammonium Bicarbonate 1.0

Dried Egg Yolk 1.0

Vanilla Flavor 0.25

Water 55

The dough so formed may be rolled, wire cut to 1/4 inch thickness, and baked by the usual process to give a vanilla wafer cookie.

Example 9

Chocolate Chip Cookies. Chocolate chip cookies may be prepared using the butterscotch cookie recipe of example 7. but substituting Ingredient Parts

Example 5 Margarine 10.0

2-propionyl 1,3-distearin 5.0

Corn Oil 5.0 for the fat ingredient,

Granulated Sugar 15.0

Brown Sugar 15.0 for the sugar, and

Example 4 Chocolate Chips 19.0 for the butterscotch bits.

EXAMPLE 10

Filled Cream. To make a "filled cream" composition, homogenize about

Inoredient Parts

2-butyryl 1,3-dipalmitin 30.0 Skim Milk 69.9

Polysorbate 80 0.1 in a conventional dairy homogenizer,

Example 11

Ice Cream. Vanilla ice cream may be prepared by mixing:

Ingredient Parts

Sugar (10X) 15.0 Nonfat Dry Milk 3.9

Salt 0.4 into Water 39.0 for 3 minutes. Then add liquid

2-butyryl 1,3-dipalmitin 28.4 and cook to 200ºF. while mixing. Hold for 1 minute. Cool to 160ºF., and add Sugared Egg Yolks 12.5

Vanilla Extract 0.8 and mix 1 minute. Cool and freeze while rotating to desired overrun.

EXAMPLE 12

Filled Milk. To prepare a "filled milk" composition, combine about

Ingredient Parts

Example 10 Filled Cream 100

Skim milk 900 and rehomogenize.

EXAMPLE 13

Cheese Products. To prepare cheese products, treat

Ingredient Parts

Nonfat milk 75.0 Low Temperature nonfat dry milk 4.0

2-butyryl 1,3-dipalmitin 20.0

To this is added

Salt 0.7

Lactic Acid Culture 0.3

The mixture is fermented and pressed to a final composition of approximately 37.0% moisture, 63.0%total solids, and 32.0% fat.

EXAMPLE 14

Butter Cream Icing. Butter cream icing may be prepared by blending:

Ingredient Parts

Sugar 227.0

2-butyryl 1,3-distearin 17.0

2-propionyl 1,3-dipalmitin 17.0

Corn Oil 36.8 Water 28.4

Nonfat Dry Milk 14.0

Emulsifier 1.4

Salt 1.0

Vanilla 1.0

All of the ingredients are creamed in a mixer at medium speed until the desired consistency is obtained.

EXAMPLE 15

Crackers. A dough prepared by mixing together

Ingredient Parts

Flour 100

Sugar 5.0

Malt 1.5

2-propionyl 1,3-dipalmitin 7.5 Salt 1.0

Sodium Bicarbonate 0.9

Nonfat Dry Milk 2.5

High Fructose Corn Syrup 2.5

Monocalcium Phosphate 0.75

Water 28 is sheeted, stamped, and baked to produce a cracker product

EXAMPLE 16

Spraved Crackers. The sheeted and stamped cracker dough of example 15 may be sprayed with liquid 2-butyryl 1,3-dipalmitin after baking.

EXAMPLE 17

Mayonnaise. Mayonnaise can be prepared from the following formulation: Ingredient Parts

2-butyryl 1,3-dipalmitin 40.0

Corn Oil 40.0

Egg yolk 5.5

Vinegar 3.0

Salt 1.5

Sugar 2.0

Flavor 0.5

Water 7.5

The egg yolk is first mixed with the other dry ingredients and a small amount of the water and vinegar in a container. Liquid 2-butyryl 1,3-dipalmitin and corn oil are slowly poured into the container, while subjecting the container contents to mixing, to form an emulsion. While continuing to agitate the emulsion, the remaining water and vinegar is added. Example 18

Pudding. Pudding can be prepared from the following formulation:

Ingredient Parts

Milk 67

Sugar 11

Starch 5

Water 9

Flavor 3

2-acetyl 1,3-distearin 5

The ingredients can be blended together to form a pudding.

EXAMPLE 19

Frying Oil. 2-butyryl 1,3-dipalmitin may be used for frying foods. EXAMPLE 20

Pet Food. Dry, expanded animal food kibs may be prepared from the following ingredients:

Ingredient Parts

Hominy Feed 37

52% Meat Meal 17

Wheat Shorts 13

2-propionyl 1,3 dipalmitin 16

Corn Germ Meal 9.6

Wheat Germ Meal 3

Dried Milk 0.9

Beet Pulp 1.7 Fish Scrap 0.5

Brewer's Yeast 0.5

Salt 0.5

Vitamins and Minerals 0.1 The ingredients are mixed together and water added to raise the water content to 27%, before extrusion, pelleting, and frying in the usual manner.

The above description is for the purpose of teaching the person of the ordinary skill in the art how to practice the present invention and it is not intended to detail all those obvious modifications and variations of it which will become apparent to the skilled worker upon reading the description. It is intended, however, that all such obvious modifications and variations and all isometric variations of chemical names and formulas, as used herein, be included within the scope of the present invention and by the following claims.

Claims

What is claimed is:

1. An edible fat composition comprising one or more low calorie fats of the following formula:

where, R and R" are long chain saturated fatty acid residues having between 16 and 40 carbons; and

R' is a short chain acid residue having 2 to 5 carbons.

2. An edible fat composition comprising one or more low calorie fats of the following formula:

where, R and R" are fatty acid residues selected from the group consisting of palmitic, stearic, arachidic, behenic, lignoceric, cerotic, montonic, and melissic acid; and

R' is an acid residue selected from the group consisting of acetic, propionic, butyric, glycolic, lactic, hydracrylic, hydroxybutyric, propenoic, and butenoic acid.

3. A food composition comprising:

(a) a reduced calorie fat having at least 35% by weight of one or more compounds of the following formula:

where, R and R" are long chain saturated fatty acid residues containing between 16 and 40 carbons, and R' is a short chain acid residue containing from 2 to 5 carbons; and

(b) at least one additional food ingredient.

4. A composition according to claims 1 to 3 wherein R and R" is a 16 to 24 carbon fatty acid residue.

5. A composition according to claim 4 wherein R and R" is a 16 to 20 carbon fatty acid residue.

6. A composition according to claims 1 to 5 wherein R and R" comprise stearic acid.

7. A composition according to claims 1 to 6 wherein R, R' and R" are derived from natural fatty acids.

8. A composition according to claims 1 to 7 wherein R and R" are derived from natural or hydrogenated oils selected from the group consisting of soybean, sunflower, peanut, safflower, olive, sesame, rice bran, canola, babassu, coconut, palm kernel, palm, rapeseed, cottonseed, corn, and butter oil, and fractions thereof.

9. A composition according to claims 1 to 8 wherein R and R" are derived from hydrogenated canola.

10. A composition according to claims 1 to 9 wherein R' is a 2 to 4 carbon fatty acid residue.

11. A composition according to claims 1 to 9 wherein R' is an acid residue selected from the group consisting of acetic, propionic, and butyric acid.

12. A composition according to claims 1 to 11 wherein the reduced calorie fat provides from 0.5 to 6.0 kcal/gram.

13. A composition according to claim 12 wherein the reduced calorie fat provides from 1.0 to 5.0 kcal/gram.

14. A composition according to claims 1 to 13 comprising a baked food product further comprising flour selected from the group consisting of rice, wheat, and corn.

15. A composition according to claims 1 to 13 comprising an emulsion having an aqueous phase and an oil phase containing the reduced calorie fat, said emulsion selected from the group consisting of margarine substitutes and salad dressings.

16. A method of preparing a reduced calorie food product having an edible fat component, said method comprising replacing at least a portion of the edible fat with one or more compounds of the formula:

R' is a short chain acid residue having 2 to 5 carbons.

17. A method according to claim 16 wherein R and R" have between 16 and 20 carbons.

18. A method according to claim 16 or 17 wherein R' is derived from an acid from the group consisting of acetic, propionic, and butyric acid.

19. A method according to claims 16 to 18 wherein R and R" comprise stearic acid residues.

20. A method according to claims 16 to 19 wherein said compound delivers 1.0 to 5.0 kcal/gram.