WO1992004833A1 - Cetones di-grasses utiles comme succedane de matieres grasses pauvres en calories dans des compositions alimentaires - Google Patents

Cetones di-grasses utiles comme succedane de matieres grasses pauvres en calories dans des compositions alimentaires Download PDF

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Publication number
WO1992004833A1
WO1992004833A1 PCT/US1991/006385 US9106385W WO9204833A1 WO 1992004833 A1 WO1992004833 A1 WO 1992004833A1 US 9106385 W US9106385 W US 9106385W WO 9204833 A1 WO9204833 A1 WO 9204833A1
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WO
WIPO (PCT)
Prior art keywords
fat
fatty
ketone
ketones
food compositions
Prior art date
Application number
PCT/US1991/006385
Other languages
English (en)
Inventor
Deborah Jean Back
Original Assignee
The Procter & Gamble Company
Priority date (The priority date 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 date listed.)
Filing date
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Application filed by The Procter & Gamble Company filed Critical The Procter & Gamble Company
Publication of WO1992004833A1 publication Critical patent/WO1992004833A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0056—Spread compositions
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres

Definitions

  • the present invention relates to the field of low calorie substitutes for edible fats. Specifically, the invention relates to the use of di-fatty ketones as a partial or complete replacement for triglyceride fats to provide reduced-calorie, fat-containing food compositions.
  • triglyceride fats which are formulated into foods or are used in the cooking of foods constitute about 90% of the total fat consumed in the average diet.
  • Patent 3,579,548 to Whyte, issued May 18, 1971 fatty acid diglyceride, diesters of dibasic acids (U.S. Patent 2,874,175 to Feuge et al.); polyorganosiloxanes (European Patent Application 205,273 to Frye); alpha-acylated glycerides (U.S. Patent 4,582,715 to Volpenhein). All of the foregoing documents are incorporated by reference herein.
  • reduced-calorie fat substitutes are medium chain triglycerides; highly esterified polyglycerol esters; acetin fats; plant sterol esters; N-Oil; polyoxyethylene esters; jojoba esters; mono/diglycerides of fatty acids; and mono/ diglycerides of short-chain dibasic acids.
  • a compound must physically resemble conventional triglyceride fat, and have the same utility in various fat-containing food compositions such as shortening, margarine, cake mixes, and the like, and be useful in frying or baking.
  • Di -fatty ketones are known compounds. Narayana et al., Tetrahedron Letter, Vol. 26(51); p. 6361 (1985) discloses the preparation of di-decyl ketone. No utility is disclosed.
  • Japanese Pat. 62027481 (Pentel) discloses the use of di-stearyl ketone as a lubricating component in pencil lead.
  • McCurry et al., J. Prg. Chem. 43(17), 3255 (1978) discloses the compound diheptadec-8-enyl ketone and its preparation. No utility is disclosed.
  • an object of the present invention to provide compounds that are poorly digested and poorly absorbed, and have organoleptic properties making them suitable for use as fat substitutes.
  • the present invention relates to a low calorie food composition
  • a low calorie food composition comprising fat and non-fat ingredients wherein the fat ingredients comprise at least 10% of the composition and wherein from 10% to 100% of the fat ingredients consist
  • R 1 -C-R 2 essentially of di-fatty ketones of the formula R 1 -C-R 2 wherein R 1 and R 2 are selected from the group consisting of C 8 to C 24 aliphatic radicals which can be saturated or unsaturated, branched or straight chain, or mixtures thereof.
  • the present invention relates to certain di-aliphatic ketones (also referred to herein as di-fatty ketones) which have been discovered to be useful as fat substitutes in low calorie fat-containing food compositions.
  • the food compositions comprise: (a) non-fat ingredients; and (b) at least 10% fat ingredients, wherein from about 10% to 100%
  • the fat ingredients comprise di-fatty ketones of the formula R 1 - C-R 2 wherein R 1 and R 2 are selected from the group consisting of C 8 to C 24 aliphatic radicals which can be saturated or unsaturated, branched or straight chain, or mixtures thereof.
  • R 1 and R 2 are selected from the group consisting of C 8 to C 24 aliphatic radicals which can be saturated or unsaturated, branched or straight chain, or mixtures thereof.
  • fat ingredients herein is meant materials which have fat-like physical properties (either in the liquid or solid state).
  • the “fat ingredients” can consist entirely of the di-fatty ketones of the present invention or can be a mixture of said ketones with digestible, partially digestible or other non-digestible fats.
  • Digestible fats are the typical triglycerides such as soybean oil, sunflower seed oil, etc.
  • nondigestible fats which can be used in combination with the di-fatty ketones are sugar and sugar alcohol polyesters such as disclosed in 3,600,186 Mattson et al. issued August 17, 1971 and 4,789,664, Seligson et al., issued December 6, 1988.
  • partially digestible fats are medium chain (C 8 -C 10 ) triglycerides.
  • the di-fatty ketones of the present invention (and food compositions containing these compounds) have desirable physical properties and palatability compared to ordinary triglyceride fats and food compositions in which all of the fat is triglyceride. However, these compounds have a substantially lower effective caloric value than
  • triglyceride fats because they are low in digestibility and absorbability in the intestinal tract. Animal feeding experiments with radiotagged compounds of the present invention indicate that said compounds are less than 20% absorbed.
  • the di-fatty ketones of the present invention have the following properties:
  • R 1 -C-R 2 wherein R 1 and R 2 are selected from the group consisting of C 8 to C 24 aliphatic radicals and mixtures thereof.
  • the said radicals can be saturated or unsaturated, straight chain or branched chain.
  • suitable radicals are octyl (C 8 ), nonyl (C 9 ), dodecyl (C 12 ), tridecyl (C 13 ) tetradecyl (C 14 ), hexadecyl (C 16 ), heptadecyl (C 17 ), octadecyl (C 18 ), eicosyl (C 20 ), 9-octadecenyl
  • triglyceride oils and fats such as soybean oil, cottonseed oil sunflower seed oil and lard.
  • Compounds in which the radicals are saturated tend to yield ketones which are solid at room temperature, while unsaturated radicals yield ketones which are liquids.
  • fat substitutes can be formulated which duplicate the physical characteristics of the various natural fats and oils.
  • liquid di-fatty ketones of the present invention with di-fatty ketones which are solid above body temperature (37oC) so the mass of nondigestible material remains in a semi -sol id state in the lower intestine.
  • other materials which are solid at body temperature such as saturated long chain fatty acids (e.g., stearic acid), digestible sources of said acids (e.g., triglycerides), solid nondigestible sucrose polyesters, etc. can be used to control oil loss of liquid di-fatty ketones. See, for example, U.S. Pat. 4,005,195, Jandacek, issued January 25, 1977 and U.S. Pat. 4,797,300 Jandacek et al., issued January 10, 1989 both incorporated herein by reference.
  • Additional solid sucrose polyester materials which are especially effective oil loss control agents for liquid nondigestible oils include sucrose octaester of mixed 1 auric acid:behenic acid in a molar ratio of about 2:6 to about 4:4, and sucrose octaester of a mixture of C 18 unsaturated acids:behenic acid in a molar ratio of about 2:6 to about 4:4.
  • the oil loss control agent will be used at a level of 5% to about 50% by weight of the liquid di-fatty ketone.
  • the fat substitutes of the invention are known compounds and can be prepared by known methods.
  • Another process illustrated in Examples I, VII and VIII herein, involves contacting the fatty acid methyl ester with a strong base such as sodium hydride or sodium
  • the di-fatty ketones of the present invention can be used as partial or total replacements for normal triglyceride fats in any fat-containing food composition to provide low calorie benefits.
  • the invention is directed toward food compositions which contain fat and non-fat ingredients with the fat ingredients being present in an amount of at least 10% of the composition.
  • fat ingredients comprise from about 10% to 75% of the composition.
  • the amount of the present compounds included in the fat will depend upon the food composition and the low calorie effect desired. In order to obtain a significant low calorie effect, it is necessary that at least about 10% (preferably at least 25%) of the fat in the food composition comprise the present compounds.
  • Typical non-fat ingredients in food compositions are sugars, starches, non-fat milk solids, and animal and vegetable proteins.
  • the compounds of the present invention are useful in a wide variety of food and beverage products.
  • the compounds can be used in the production of baked goods in any form, such as mixes, shelf-stable baked goods, and frozen baked goods. Possible applications include, but are not limited to, cakes, brownies, muffins, bar cookies, wafers, biscuits, pastries, pies, pie crusts, and cookies, including sandwich cookies and chocolate chip cookies, particularly the storage-stable dual-textured cookies described in U.S.
  • Patent 4,455,333 of Hong & Brabbs The baked goods can contain fruit, cream, or other fillings.
  • Other baked good uses include breads and rolls, crackers, pretzels, pancakes, waffles, ice cream cones and cups, yeast-raised baked goods, pizzas and pizza crusts, baked farinaceous snack foods and other baked salted snacks.
  • the present compounds can be used alone or in combination with triglyceride fats or reduced calorie or zero calorie fats, to make shortening and oil products.
  • Shortening and oil products include, but are not limited to, shortenings, margarines, spreads, butter blends, lards, cooking and frying oils, salad oils, popcorn oils, salad dressings, mayonnaise, and other edible oils.
  • the present compounds can be used to make foods that are fried in oil (e.g., potato chips, corn chips, tortilla chips, other fried farinaceous snack foods, french fried potatoes, doughnuts, and fried chicken).
  • Imitation dairy products can also be made (e.g., butter, ice cream and other fat-containing frozen desserts, yogurt, and cheeses, including natural cheeses, processed cheeses, cream cheese, cottage cheese, cheese foods and cheese spread, milk, cream, sour cream, butter milk, and coffee creamer), by replacing at least part of the natural fat in such products with compounds of the invention.
  • the present compounds are also useful for making reduced calorie meat products (e.g, hamburgers, hot dogs, frankfurters, wieners, sausages, bologna and other luncheon meats, canned meats, including pasta/meat products, stews, sandwich spreads, and canned fish), meat analogs, tofu, and various kinds of protein spreads.
  • Sweet goods and confections can also be made (e.g., candies, chocolates, chocolate confections, frostings and icings, syrups, cream fillings, and fruit fillings), as well as nut butters and various kinds of soups, dips, sauces and gravies.
  • the present compounds can be fortified with vitamins and minerals. Fortification with fat-soluble vitamins is particularly desirable, since nondigestible fatty materials can cause some reduction in the absorption of these vitamins. See U.S. Pat. 4,034,083, Mattson, issued July 5, 1977, incorporated by reference herein.
  • the fat-soluble vitamins include vitamin A, vitamin D, vitamin E, and vitamin K.
  • the amount of the fat-soluble vitamins employed to fortify compositions containing the nondigestible fat can vary, depending on a number of factors. If desired, the compounds can be fortified with a recommended daily allowance (RDA), or increment or multiple of an RDA, of any of the fat-soluble vitamins or combinations thereof.
  • RDA recommended daily allowance
  • Noncaloric or reduced calorie sweeteners include, but are not limited to, aspartame, saccharin, alitame, thaumatin, and cyclamates.
  • the compounds of the present invention can be used in combination with other noncaloric or reduced calorie fats, such as sugar or sugar alcohol fatty acid polyesters, branched chain fatty acid triglycerides, triglycerol ethers, polycarboxylic acid esters, sucrose polyethers, neopentyl alcohol esters, silicone oils/siloxanes, and dicarboxylic acid esters. See documents incorporated by reference in BACKGROUND OF THE INVENTION supra.
  • partial fat replacements useful in combination with the present compounds are medium chain triglycerides, highly esterified polyglycerol esters, acetin fats, plant sterol esters, polyoxyethylene esters, jojoba esters, mono/diglycerides of fatty acids, and mono/diglycerides of short-chain dibasic acids.
  • the bulking agents can be nondigestible carbohydrates, for example, polydextrose and cellulose or cellulose derivatives, such as carboyxmethylcellulose, carboxyethylcellulose, hydroxypropylcellulose, methylcellulose and microcrystalline cellulose.
  • suitable bulking agents include gums (hydrocolloids), starches, dextrins, fermented whey, tofu, maltodextrins, polyols, including sugar alcohols, e.g., sorbitol and mannitol, and carbohydrates, e.g., lactose.
  • dietary fiber complex carbohydrates resistant to digestion by mammalian enzymes, such as the carbohydrates found in plant cell walls and seaweed, and those produced by microbial fermentation.
  • these complex carbohydrates are brans, celluloses, hemicelluloses, pectins, gums and mucilages, seaweed extract, and biosynthetic gums.
  • Sources of the cellulosic fiber include vegetables, fruits, seeds, cereals, and man-made fibers (for example, by bacterial synthesis).
  • Naturally occurring fibers include fiber from whole citrus peel, citrus albedo, sugar beets, citrus pulp and vesicle solids, apples, apricots, and watermelon rinds.
  • a primary benefit is the calorie reduction achieved when the present compounds are used as a total or partial fat replacement. This calorie reduction can be increased by using combinations of the present compounds with reduced calorie sweeteners, bulking agents, or other reduced calorie or noncaloric fats. Another benefit which follows from this use is a decrease in the total amount of triglyceride fats in the diet.
  • a di-fatty ketone useful in compositions of the present invention is prepared according to the following procedure: a) Preparation of ⁇ -keto ester
  • ketone as follows: 1768 g. crude reaction product (2.25 moles ⁇ -keto ester) is placed in a beaker and 3536 g of KOH coated alumina is then added with stirring. The beaker is then heated to boiling in a microwave oven for four one-minute time sequences. Between each heating cycle the mixture is stirred and allowed to cool until boiling ceases.
  • Example I The procedure of Example I is followed except that methyloleate instead of methyl esters of hydrogenated soybean oil is used to prepare the ⁇ keto ester.
  • the product, di[heptadec-8-enyl ketone] is liquid at room temperature.
  • a salad dressing is prepared using the liquid di-fatty ketone of Example IV.
  • a solid di-fatty ketone which is useful to formulate with liquid di-fatty ketones in preparing food compositions as the invention is prepared as follows. a) Preparation of ⁇ -keto ester
  • the residue is then dissolved into hot toluene and the di-fatty ketone is crystallized by the addition of methanol.
  • the suspension is allowed to stir at ambient temperatures for 2 hours and is then filtered via a buchner funnel.
  • the filter cake is then washed with cold methanol and the di-fatty ketone solid is dried in a vacuum oven for about 12 hours.
  • the product has a melting point of 94-95oC.
  • a liquid di-fatty ketone useful in formulating compositions of the present invention is prepared as follows. a) Preparation of ⁇ -keto ester

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Mycology (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Edible Oils And Fats (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

L'invention concerne certaines cétones di-grasses utilisées comme produits de remplacement non digestibles de matières grasses naturelles dans des compositions. Lesdites cétones ont la formule (I), dans laquelle R1 et R2 sont sélectionnés chacun parmi des radicaux aliphatiques C8 à C24.
PCT/US1991/006385 1990-09-21 1991-09-09 Cetones di-grasses utiles comme succedane de matieres grasses pauvres en calories dans des compositions alimentaires WO1992004833A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US58646190A 1990-09-21 1990-09-21
US586,461 1990-09-21

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WO1992004833A1 true WO1992004833A1 (fr) 1992-04-02

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Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
Procter and Gamble Company, FOOD ADDITIVE PETITION FOR OLESTRA, 1 April 1987, Vol. 1, page 31. *
Procter and Gamble Company, FOOD ADDITIVE PETITION FOR OLESTRA, 1 April 1987, Vol. 1, Section E. See page 92, lines 27-40, page 93 and page 94, 1.1-8. *
Procter and Gamble Company, FOOD ADDITIVE PETITION FOR OLESTRA, 1 April 1987, Vol. 35, example 5. See pages 2-5. *
Procter and Gamble Company, FOOD ADDITIVE PETITION FOR OLESTRA, 1 April 1987, Vol. 35, example 7, see page 5. *
Procter and Gamble Company, FOOD ADDITIVE PETITION FOR OLESTRA, 1 April 1987, Vol. 35, example 8. See pages 5 and 14. *
Procter and Gamble Company, FOOD ADDITIVE PETITION FOR OLESTRA, 1 April 1987, Vol. 35, example 9. See page 5. *

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