WO1991010372A1

WO1991010372A1 - Low calorie nuts with the organoleptic character or full fat nuts

Info

Publication number: WO1991010372A1
Application number: PCT/US1991/000163
Authority: WO
Inventors: Oris Edwin Holloway; John W. Finley; Edward L. Wheeler
Original assignee: Nabisco, Inc.
Priority date: 1990-01-09
Filing date: 1991-01-08
Publication date: 1991-07-25
Also published as: AU7074191A

Abstract

The present invention relates to nuts which have a near normal fat content but with a portion of their natural fat replaced with a low calorie fat-like material. This is achieved by defatting the nuts partially and then infusing them with a non-digestible or partially digestible fat-like material. The resulting nuts have the organoleptic character of full fat nuts but a much lower calorie content.

Description

LOW CALORIE NUTS WITH THE ORGANOLEPTIC CHARACTER OR FUU.FAT NUTS BACKGROUND OF THE INVENTION

The present invention relates to nuts, and particularly to an improved process for preparing reduced calorie nuts.

The term "nuts" as used in this description includes whole nuts and pieces of nuts such as peanuts, cashews, almonds, Brazil nuts, filberts, pecans, walnuts, and the like. For purposes of conciseness in description, the following disclosure will center around the production of low-fat peanuts. It is not intended, however, to be limited to peanuts because the principles which will apply for peanuts should apply to other nuts.

The basic procedures for preparing partially defatted nuts have been known for a number of years. For example, in U.S. Patent No. 2,003,415 to Ammann ("Ammann") and U.S. Patent No. 3,294,549 to Vix et al. ("Vix"), procedures for pressing the oil from nuts such as peanuts are described. Broadly, these methods include the steps of pressing nuts until the desired quantity of fully digestible triglyceride fats are removed and then steaming or cooking the partially defatted nuts in water until the nuts are reconstituted to substantially their original size and shape. Both of these patents discuss the virtues of partially defatted nuts in the diet. It is the decrease of triglyceride fat level in partially defatted nuts that give them a significantly lower calorie content than full fat nuts. Further work on the process of Vix is described in a series of articles entitled, "Development and Potential of Partially Defatted Peanuts," Peanut Journal and Nut World, January and February 1967, and an article entitled, "Low Calorie Peanuts", Food Processing/Marketing, September, 1965. Later workers, encouraged by the apparent appeal of partially defatted nuts to weight-conscious consumers, continued to work in this area. U.S. Patent No. 3,645,752 to Baxley discloses a process which improves the flavor of partially defatted nuts by quenching them in a flavored oil after roasting. Although such oil quenching improves the flavor of partially defatted nuts, it also restores them to a substantially full fat content.

U.S. Patent No. 3,740,236 also to Baxley indicates that roasted peanut flavor is reduced in proportion to the percentage of the peanut oil removed during the pressing process. Baxley, however, does not prevent flavor loss but only improves flavor after it is diminished. This is achieved by reconstituting partially defatted nuts in an aqueous binder solution containing flavor.

The reason for the loss of flavor in partially defatted nuts is not fully understood. The Doctoral Dissertation of M. E. Mason, entitled "Procedures in Studying and Factors Influencing the Quality and Flavor of Roasted Peanuts", Oklahoma State University, 1963, pages 63 and 64, indicates that the triglyceride fat pressed from peanuts contains aleurone grains, among other particulates, which appear to contain flavor precursors. The Mason dissertation, however, is not concerned with the preparation of low-fat nuts, but simply with gaining a better knowledge of the source and identification of flavor principals in peanuts. U.S. Patent No. 4,049,833 to Gannis et al. ("Gannis") also recognizes the adverse effect partially defatting nuts has on flavor and texture. To correct this, Gannis contacts partially defatted nuts with a glycerol-containing solution to reconstitute them before roasting.

U.S. Patent No. 4,329,375 to Holloway et al. ("Holloway") discloses a process for preparing low-fat nuts, such as peanuts, which retain more of their natural flavor and texture than products prepared by earlier procedures. This high quality product is achieved by pre-roasting the nuts to partially develop a roasted nut flavor and color, pressing only after equilibration of the internal nut moisture, and limiting the amount of oil extraction.

U.S. Patent No. 4,466,987 to Wilkins et al. ("Wilkins") relates to the production of low fat nuts prepared by moistening, initially roasting, pressing, hydrating, and finally roasting.

Although the partially defatted nuts of Gannis, Holloway, and Wilkins represent vast improvements over those products prepared simply by pressing and then cooking with hot water or steam, all such nut products inherently lack the taste and mouthfeel of full fat nuts. This problem is, at least in part, due to the lower oil content of such nuts. It is also caused by the destruction of the nut microstructure during pressing. Such structural damage is not restored by mere roasting and reconstitution. As a result, roasted, partially defatted nuts lack the crunch of full fat nuts. SUMMARY OF THE INVENTION

The present invention relates to the preparation of nuts which have been partially defatted, roasted, and then contacted with a non-digestible or partially digestible fat-like substance. As a result, the nuts have a lower calorie content than full fat nuts, but an oily mouthfeel and, preferably, a crunchy texture like such full fat nuts.

The roasted, partially defatted nuts can be prepared from full fat nuts in accordance with any known procedure.

Once roasted or cooked, the partially defatted nuts are contacted with a low calorie fat-like material. For purposes of this application, the term "low calorie fat-like material" is defined as a non-digestible or only partially digestible, edible material which can replace fully digestible triglyceride fats or oils in the human diet. These materials provide the benefits of triglyceride fats and oils—i.e., lubricity and flavor—without the calories. In this application, "fully digestible" shall mean that substantially all (up to 100%) of the material is not digested, providing up to 9 kilocalories per gram. The term "non-digestible" shall mean that substantially all of the material is not digested by the human body and passes through the digestive system unchanged. The term "partially non-digestible" shall encompass materials with a level of digestibility between that of non-digestible and fully digestible materials, preferably where 1.0 to 8.0 kilocalories per gram are provided.

Contact with the low calorie fat-like material causes the fat-like material to infuse into the partially defatted nuts. As a result, the nuts have the organoleptic character (i.e., oily mouthfeel) of full fat nuts without the calories. This occurs because of the non-digestible or partially digestible nature of the low calorie fat-like material infusant which, unlike fully digestible triglyceride fats^', passes through the human digestive system while significantly reducing the product's caloric density. It is particularly advantageous to infuse low calorie fat-like materials which are solid at room temperature to restore added crunch to the nut product.

A number of non-digestible or partially digestible fat-like materials have been developed, and, generally, any such material which is a liquid at infusion temperatures can be utilized. Advantageously, the fat-like material contains liquid additives such as natural or artificial flavoring agents (preferably nut extracts), vitamins, and sweeteners (preferably aspartame).

DETAILED DESCRIPTION OF THE INVENTION

Low fat nuts with the organoleptic character of full fat nuts are produced according to the present invention by what is generally a two-stage process. In the first stage, roasted or cooked partially defatted nuts are prepared and, in the second stage, nuts from the first stage are infused with a low calorie fat-like material.

The preparation of roasted, partially defatted nuts in the first stage can be carried out by any one of several processes. For example, any of the processes of Ammann, Vix, Gannis, Holloway, or Wilkins, all of which are hereby incorporated by reference, can be used. Roasted partially defatted nuts may be prepared by first mechanically pressing the raw nuts to extract 40-52% of their initial triglyceride fat content. Such mechanical pressing can be carried out in a Carver Press at pressures of 1000-1500 psig, preferably 1100- 1300 psig, for times of 15-120 minutes. After pressing, it is necessary to expand the nuts from their flat and undesirably dense form. When the nuts are to be air roasted, they must be contacted with sufficient water (i.e., by contacting the huts with water at a level of

3-7, preferably 4, pounds of water per 100 pounds of nuts) to reconstitute them when subsequently roasted. When oil roasting, reconstitution will occur without such preliminary hydration.

When air roasting, the nuts are roasted in a stream of hot air at a temperature of about 275°F to about 400^βF, preferably about 320° to about 335°F. The partially defatted nuts are roasted to a moisture level of less than 3% so that they have an Agtron Color Photometer reading of 60-95 in the green mode with 12% and 33% plates defining the reading scale.

It is preferred that oil roasting be carried out in low calorie fat-like materials to keep the partially defatted nuts low in calories. However, roasting can be conducted in mixtures of such fat-like materials and fully digestible triglyceride fats where higher calorie levels can be tolerated.

Once partially defatted and roasted {i.e., stage one is completed) , the nuts are ready to be contacted with a low calorie fat-like material (i.e., stage two). At some point during such contact, the fat-like material must be in a liquefied state so that it will be infused into the nut. Therefore, fat-like ^* materials which are liquids at temperatures below 300°F can be utilized.

One type of low calorie fat-like material which is particularly suitable for infusion of roasted, partially defatted nuts is that disclosed by U.S. Patent No. 4,830,787 to Klemann et al. which is hereby incorporated by reference.

Low calorie fat-like materials of this type, having both carboxylate and carboxy groups extending from a backbone, are referred to throughout this application as carboxy/carboxylate esters. They are defined by the following formula:

O 0 (R'-C II-0-)_rn(R)(-CII-0-R^,)_» where:

R is an organic radical;

R' is an aliphatic, ester, or ether group having from 1 to

30 carbon atoms, the various R' groups being the same or different; and m and n are integers of at least 1, and the sum of m and n is at least 3. The R group of the above formula is analogous to the glycerol residue which forms the backbone of natural fats. The total of m and n (i.e., the total number of carboxy and carboxylate groups appended to the backbone R) , their placement on the backbone, the backbone structure, and selection of various R' groups, will be determined by the biological and physical properties of the desired compound. Preferred carboxy/ carboxylate esters are dialkoxy acylmalates defined by the formula:

and dialkoxy di(acyl)tartrates defined by the formula:

For both of these compounds, R' is the same as that defined above with respect to the generic carboxy/carbαxylate ester formula. Of the dialkoxy acylmalate and dialkoxy di(acyl) tartrate compounds, compounds which are solid at room temperature and a liquid at below 150° F are particularly preferred. It is particularly desirable that the low calorie fat-like material have a melting point around normal body temperature (i.e. 98.7°F) so that it dissolves as the nuts are broken down by chewing. This is because, after such materials are infused as liquids and allowed to resolidify in the nuts, the characteristic crunch present in full fat nuts is restored. The adverse effect of pressing on the nut microstructure is thus obviated. Examples of such compounds include dilauryl myristoyl malate and dimyristyl myristoyl malate. Another class of low calorie fat-like materials suitable for infusing roasted, partially defatted nuts is known as sucrose polyesters. These are sugar and sugar alcohol fatty acid esters having at least four fatty acid ester groups. Such compounds are disclosed by, e.g., U.S. Patent No. 3,600,186 to Mattson et al. and U.S. Patent No. 3,954,976 to Mattson et al., both of which are hereby incorporated by reference. All of these compounds are said to possess physical properties similar to fully digestible triglyceride fats, but to be absorbed less rapidly when eaten. It is, unfortunately, this very attribute which causes undesirable and potentially embarrassing side effects, including the frank anal discharge of the materials. One solution to this problem is the addition of anti-anal leakage agents to the sucrose polyesters, as suggested by, e.g., U.S. Patent No. 4,005,195 to Jandacek which is hereby incorporated by reference. These anti-anal leakage agents include solid fatty acids (melting point 37°C or higher) and their triglyceride source, and solid polyol fatty acid polyesters.

Another type of low calorie fat-like material for infusing roasted, partially defatted nuts are esterified trishydroxymethyl compounds (hereby incorporated by reference), as discussed in U.S. Patent Application Serial No. 07/311,709, entitled "Tris-Hydroxymethyl Alkane Esters As Low Calorie Fat Mimetics". These compounds are defined by the following general formula:

n where : n is 1 or 2 ;

X is an alkyl group having from 1 to 5 carbons when n = 1, or an alkyl, ether or ester bridge having 1 to 8 carbons when n = 2; and

F_1# F₂, and F₃ are fatty acid residues or dicarboxylate-extended fatty acid residues.

Thus, the compounds of the invention^' comprise monomeric trishydroxymethyl alkane esters of the general formula: ^•

or a trishydroxymethyl alkane ester dimer coupled by an alkyl, ether, or ester bridge having 1 to 8 carbons of the general formula:

F_ι-(CO)-0-CH₂ H₃C-O-(C0)-Fa.

F_a.-(CO)-0-C C I-CH₂-0-(C0)-F₂ F_a.-(C0)-O-C IH₂ H₂C-0-(CO)-F,

where:

R is an alkyl group having from 1 to 5 carbons;

X is an alkyl, ether or ester bridge having 1 to 8 carbons; and

Fa., F_2/ and F₃ are fatty acid residues or dicarboxylate-extended fatty acid residues. One example of such a compound is 1,1,1-tris-hydroxymethylethane trimyristate. -u- Complex linked esters, defined by the following general formula, are also useful as low calorie fat-like materials in the present invention:

where:

R is a linking covalent bond or saturated or unsaturated aliphatic group, preferably with up to 10 carbons, most preferably 1 to 6; n is 2 to 6, and preferably 2 to 4; and

R' comprises residues defined by the following formula:

where:

C is a carbon atom;

X is a bridging bonding valence, hydrogen, or substituted or unsubstituted lower aliphatic group (e.g., -_-C_), the various X groups being the same or different;

O

Q is -C II-O-R'' (carboxylate),

O -R' * '-C II-O-R' ' (alkylcarboxylate) ,

O 0

-O-C II-R' ^• ' (carboxy) , -R" '-o-CII-R' ' (alk lcarboxy) ,

-O-R" (alkoxy), or -R"'-0-R" (alkylalkoxy) radicals, with the proviso that at least one of the Q radicals be other than carboxy;

R' ' is a substituted or unsubstituted aliphatic group, containing, for example, no more than 30 carbons, e.g..

the various R' and R' ' groups, respectively, being the same or different;

R' ' ' is a lower alkylene, desirably methylene or ethylene, preferably methylene, group which can be the same or different;

T is hydrogen or a substituted or unsubstituted aliphatic group, e.g., no greater than 22 carbons, containing 0 to 5 unsaturated linkages (e.g., double or triple bonded carbons) per T residue;

Z is a bridging bonding valence, hydrogen, or an alcohol, glycol, ester, e.g.,

ether, or the like, residue;

with the proviso that there is only one bridging bonding valence per R¹ group; and where :

a is 0 to 3, preferably 0 to 2; b is 0 to 4, preferably 0 to 1; d is 1 or 2; e is 0 to 5, preferably 1 to 2; f is 0 to 3, preferably 0 to 2; g is 0 to 4, preferably 0 to 1; h is 1 or 2; and j is 0 to 10, preferably 0 to 3.

Complex linked esters are more fully discussed in U.S. Patent Application Serial No. 07/144,962, entitled "Low Calorie Fat Mimetics" which is incorporated by reference.

Complex polyol esters with fatty acid residues and/or residues of esters or ethers having an acid function, as disclosed in U.S. Patent Application Serial No. 07/160,851 (hereby incorporated by reference), entitled "Low Calorie Fat Mimetics", are also useful as low calorie fat-like materials. Such complex ethers are defined by the following formula:

O -^• (FA)_ro--R-(-C II-B-R^,)_rτ

wherein FA represents a fatty acyl residue, R represents a polyol residue, m is zero or an integer from 1 to 7, n is an

O integer from 1 to 7, B is -(CH₂)-,-0-, -(CH₂)_d-C II-O-, or o -(CH₂)₃-O-C II-, and the R' groups can be the same or -14- different and can comprise residues defined by the following formula:

where C, X, Q, R' ' , R' " , T, Z, a, b, d, e, f, g, h, and j are defined above with respect to the complex linked esters except that there is no requirement that at least one Q radical be other than carboxy.

Another class of low calorie fat-like materials are those disclosed in U.S. Patent Application Serial No. 07/224,409 (hereby incorporated by reference) entitled "Ether Bridged Polyesters" and, known as ether bridged polyesters. Such compounds are defined by the following formula:

P-Q-P The P symbol represents polyesters and the Q symbol represents the ether bridge. The symbol P can be further symbolized as follows:

X

where:

X and Y are H, (-CH₂)_r-.-C0₂-Z except that at least one X or Y is not H; -15- Z is a branched or un-branched alkyl chain having

2-26 carbon atoms, wherein the alkyl chain may be saturated or unsaturated; n equals 0, 1 or 2;

R

Q is equal to O or (-0-CH₂-C IH-)_m-0-; m is equal to an integer between one 1 to 20 and preferably between about 1 to 10.

Diol lipid analogues, having 2 fatty acids esterified to a diol which is not ethylene glycol or glycerol, as disclosed in U.S. Patent Application Serial No. 07/372,689 (hereby incorporated by reference) , entitled "Diol Lipid Analogues As Edible Fat Replacements", are also suitable low calorie fat-like materials. The compounds have the following general formula:

R-(C0)-O-(D)-O-(CO)-R' ,

where:

D is an organic radical having 4 to 10 carbons and R and R' are aliphatic groups having 1 to 29 carbons.

Another type of low calorie fat-like material suitable for use in the present invention are cyclohexyl diol diesters defined by the following structural formula:

X-Q-X, where :

Q is a cyclohexane, cyσlohexene or cyclohexdiene ring backbone; X is a -0-(CO)-R, -CH₂-0-(CO)-R, or

-(CH₂)₂-0-(CO)-R side chain; and R is, independently, an aliphatic group having 1 to

29 carbons.

Such compounds are disclosed in U.S. Patent Application Serial No. 07/372,288, entitled "Cyclohexyl Diol Diesters As Low Calorie Fat Mimetics", which is hereby incorporated by reference.

Long chain diol diesters are also useful as low calorie fat-like materials in the present invention. These materials are disclosed in U.S. Patent Application Serial No. 07/372,056, entitled "Long Chain Diol Diesters As Low Calorie Fat Mimetics", which is hereby incorporated by reference, and defined by the following structural formula:

where:

A is an alkyl group having from 7 to 28 carbons; n is 0 to 2; and

Fi and F₂ are aliphatic groups having 1 to 30 carbons or dicarboxylate-extended aliphatic groups of the formula -(CH₂)-„-(CO)-0-R, where m = 1 to 4, and R contains 1 to 30 carbons. Another suitable low calorie fat-like material is acylated amino acid derivatives, as disclosed in U.S. Patent Application Serial No. 07/409,454, entitled "Acylated Amino Acid Ester Derivatives As Low Calorie Fat Mimetics" (hereby incorporated by reference) . The compounds of this invention have at least one amino group acylated with a fatty acid derivative and at least one carboxylic group esterified with a fatty alcohol derivative, and may be described by the following general formula:

(R'-0-(CO)-)--A(-NH-(CO)-R)„

where:

A is a hydrocarbyl group having 1 to 6 carbons;

X is a free or acylated amino acid chain having 1 to 25 carbons; m is 1 to 2; n is 1 to 2; p is 0 to 1;

each

R is, independently, a C_x to C₂₉ aliphatic group, a C₂ to C₂₉ ether of the formula R''-θ'R'*'-, or a C₂ to C₂₉ ester group of the formula R'''-0-(CO)- R"- or R"-(CO)-0-R' "-, where R"- and R' "- are, independently, aliphatic groups, and each

R' is, independently, a C-. to C₃₀ aliphatic group, a C₂ to C₃₀ ether of the formula R''-0'R'''-, or a C₂ to C₃₀ ester group of the formula R' ' ' -0-( CO) -

R' ' - or R" - (CO) -0-R' " - , where R" - and R" ' - are , independently, aliphatic groups.

Another type of low calorie fat like material suitable for infusion into roasted, partially defatted nuts is primary amide esters, as set forth in U.S. Patent Application Serial No. 07/409,237, entitled "Primary Amide Esters As Low Calorie Fat Mimetics" (hereby incorporated by reference) . The compounds of this invention are alkanolamines having a two- to six-carbon backbone to which are attached fatty groups in at least one ester and at least one primary amide linkage and may be described by the following general formula:

O 0

(R-C II-HN)_m-(B)-(0-CII-R)„

where:

B is an organic radical having from 2 to 6 carbons; m is 1 to 3; n is 1 to 3; and

each

R, is independently a C_x to C₂₉ aliphatic group, a C₂ to C₂₉ ether group of the formula R'-O-R' '-, or a C₂ to C₂₉ ester group of the formula R"-0-(CO)-R'- or R'-(CO)-0-R"-, where R'- and R"- are, independently, aliphatic groups. Polyvinyl alcohols esterified with fatty acids, as disclosed by U.S. Patent Application Serial No. 07/312,618, entitled "Polyvinyl Oleate As A Fat Replacement" (hereby incorporated by reference), are useful as low calorie fat-like materials for purposes of the present invention.

Another class of low calorie fat-like materials which is suitable for infusing of low calorie partially defatted nuts are thio ester derivatives, as disclosed by U.S. Patent Application Serial No. 07/409,886, entitled "Thio Derivatives As Low Calorie Fat Mimetics" (hereby incorporated by reference). These compounds have a two- to six- carbon backbone to which is attached at least one fatty C_a. to C₂₉ aliphatic, ether, ester or thioester group in ester linkage, and at least one other fatty group in ester or thioester linkage, and may be described by the formula:

O O

(R-C II-0)_m-(B)-(S-CII-R),

where:

B is a linear or branched alkyl backbone having from 2 to

6 carbons; m is 1 to 6; n is 0 to 3; and

R is, independently, an aliphatic, ether, ester or thioester group having 1 to 29 carbon atoms, with the proviso that m + n is greater than or equal to 2, and that each compound has at least one thioester bond. Alcohol amine esters, as described in U.S. Patent

Application Serial No. 07/409,381, entitled "Alcohol Amine

Esters As Low Calorie Fat Mimetics" (hereby incorporated by reference), are useful as low calorie fat-like materials in accordance with the present invention. These compounds have a nitrogen to which is attached at least one fatty group in ester linkage via an alkylene bridge and at least one other fatty group attached either with a second ester bond via an alkylene bridge, or in amine or amide linkage, and can be represented by the following general formula:

O (R-(CO)_)---NH__(-A-O-C II-R),

where:

A is -(CH₂)₂-, -(CH₂)₃-, or -CH₂CH(CH₃)-; m is 0 to 2; n is 0 to 1; q is 1 to 3 (independently); with the proviso that m + q = 2, r is O to l (independently), and each R is, independently, a C_. to C₂₉ aliphatic group, a C₂ to C₂₉ ether group of the formula R'-O-R'¹-, or a C₂ to C₂₉ ester group of the formula R"-0-(CO)-R'- or R'-(CO)-0-R"-, where R'- and R"- are, independently, aliphatic groups.

Alkoxy/Carboxylate esters, described in the copending U.S. Patent Application, entitled "Low Calorie Fat Mimetics Comprising Alkoxy/Carboxylate Esters" are also useful as low calorie fat-like materials in accordance with the present invention. Carboxylates have carbons attached to a backbone; alkoxys have ether oxygens attached to the backbone. Carboxy groups may, optionally, be present; these have an ester oxygen attached to the backbone. The compounds of this invention have the following formula:

(X-(Q)_5.-0-(C0)

where:

A is a hydrocarbyl group having 2 to 6 carbons;

X and Y are R or R' (independently); each R is, independently, a C-. to C₃₀ fatty acid residue and each R' is, independently, a C_x to

C₃₀ fatty alcohol residue; Q = -CH₂CH₂-0-, -CH(CH₃)CH₂-0-, -CH₂-CH(CH₃)-0-, or -(CH₂)₃-0-; m is 1 to 3; n is 1 to 3; p is 0 to 3, independently; q is 0 to 3, independently; s is 0 to 2, independently; provided that, when q = 0, at least one Y must be R' , and also provided that, when A has 2 carbons, R and R' are aliphatic, and if m = 1 and p = q = s = 0, then n = 2.

Another class of compounds useful as low calorie fat-like materials are secondary amide esters, as disclosed by U.S. Patent Application Serial No. 07/409,394, entitled "Secondary Amide Esters As Low Calorie Fat Mimetics" (hereby incorporated by reference) . The compounds of this invention are secondary amide esters, acylated amino alcohol derivatives which have a two- to six- carbon backbone to which are attached at least one fatty aliphatic, ether, or ester C_x or C₂ to C₂₉ group in ester linkage and at least two other fatty groups in secondary amide linkage. This new class of edible fat mimetics comprise compounds having the following general formula:

O O

(R-C II-0-)_mA(-N(-CII-R)₂)-_.,

where:

A is an organic radical having from 2 to 6 carbons; i is 1 to 3; n is 1 to 3; and each R, is independently a C_a. to C₂₉ aliphatic group,a

C₂ to C_2β ether group of the formula R'-O-R¹¹-, or a

C₂ to C₂₉ ester group of the formula R"-0-(CO)-R'- or

R'-(CO)-0-R"-, where R'- and R"- are, independently, aliphatic groups.

Extended esters, as described in U.S. Patent Application Serial No. 07/409,137, entitled "Extended Ester Derivatives As Low Calorie Fat Mimetics" (hereby incorporated by reference) , are also useful as low calorie fat-like materials for infusing roasted, partially defatted nuts. The extended esters of this invention comprise partially digestible compounds which have a -23-

2 to 5-carbon aliphatic backbone to which is attached at least one fatty acid in ester linkage and at least one fatty acid in dicarboxylate-, ethoxide-, or propoxide-extended ester linkage. The extended esters of this invention are compounds having the following general formula:

O (R-C II-0-)_m(A)(-0-B)-.,

where:

A is an aliphatic group having 2 to 5 carbons; π is 1 to 2; n is 1 to 2;

B is either an ethoxy- or propoxy-extended ester of the formula -(CH_aCH₂-O-) _v-(CO)-R,

-l(CH₂)₃-0-)_,-(CO)-R, or

-(CH₂CHCH₃-0-)-_-(CO)-R, where p = 1 to 5 and R is a Ca. to C₂₉ aliphatic group; or a dicarboxylate-extended ester of the formula

-(CO)-(CH₂).-(CO)-0-R' , where s = 1 to 5 and R' is a C to C_ao aliphatic group.

Partially digestible sucrose esters, as described in U.S. Patent Application Serial No. 07/336,821, entitled "Partially Digestible Sucrose Esters As Low Calorie Fat Mimetics" (hereby incorporated by reference) , are also useful as low calorie fat-like materials in accordance with the present invention. Sucrose has eight hydroxyl groups available for esterification. The compounds of this invention comprise mixtures of sucrose molecules esterified with at least one and as many as eight fatty acids; preferred compound mixtures have four to eight hydroxyl groups esterified, although sucrose lower esters may comprise a minor component of the ester mixture in some embodiments. Thus, this invention comprises partially digestible mixtures of sucrose molecules to which are attached fatty acid residues in ester linkage to form physiologically compatible fat replacements for foods and pharmaceuticals. The mixture may contain sucrose mono- to octa-esters, preferably tetra to octa-esters. The fatty acid residues may be the same or different, and may comprise a mixture of residues. The term "fatty acids" used here means organic fatty acids containing 2 to 30 carbons, more narrowly 10 to 23, and even more narrowly 12 to 20, and may be synthetic or natural, saturated or unsaturated, with straight or branched chains.

It is also possible to use reduced calorie triglycerides derived from glycerol esterified with long chain fatty acids at the 1- and 3- positions and a short chain acid at the 2- position, as disclosed by U.S. Patent Application Serial No. 07/410,161, entitled "Reduced Calorie Triglycerides In Foods" (hereby incorporated by reference), as low calorie fat-like materials in accordance with the present invention. These reduced calorie triglycerides are defined by the following formula: CH₂OR

C IHOR¹

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.

Other low calorie fat-like materials which can be infused into roasted, partially defatted nuts include branched chain fatty acid triglycerides, glycol ethers, polycarboxylic acid esters, neopentyl alcohol esters, silicone oils/siloxanes, dicarboxylic acid esters, poorly absorbed triglyceride-derived fats, highly esterified polyglycerol esters, acetin fats, plant sterol esters, polyoxyethylene esters, esterified propoxylated or ethoxylated glycerol or the like, jojoba esters, mono/diglycerides of fatty acids, low caloric alkyl glycoside fatty acid polyester fat substitutes as described in U.S. Patent No. 4,840,815 to Meyer et al. (hereby incorporated by reference), tristearin, tripalmitan, esterified castor oil, alpha-acylated glycerides, as taught by U.S. Patent 4,582,715 to Volpenheim (hereby incorporated by reference), triglycerides with particular combinations of saturated medium chain fatty acids, saturated long chain fatty acids, and unsaturated long chain fatty acids, as taught by U.S. Patent No. 4,832,975 to Yang (hereby incorporated by reference), and mono/diglycerides of short-chain dibasic acids.

These low calorie fat-like materials can be infused -26- individually or in admixture into roasted, partially defatted nuts. Alternatively, such fat-like materials can be blended with fully digestible triglyceride fats and then infused into such nuts to produce a product with a higher calorie content but one which is still below that of full fat nuts.

Preferably, the low calorie fat-like material contains a flavoring agent which is incorporated into the nuts during infusion. Suitable flavoring agents include nut flavor concentrates which are naturally present in nuts or nut oil. Such materials can be obtained by a variety of conventional techniques (e.g., dark roasting nuts and then extracting the nut oil) and will replace any flavor components lost during pressing. These nut flavor concentrates can be recovered from nuts which are either the same as or different from the partially defatted nut being infused. Other flavoring agents include: fruit flavors; chocolate or other confectionery flavors; mint flavor; honey flavor; flavors associated with alcoholic beverages such as beer, wine, and whiskey; any other desired artificial or natural flavor, and mixtures thereof.

Heat sensitive additives, such as artificial sweeteners (e.g., aspartame) and certain fat-soluble vitamins A, C (citric acid), D, and E (alpha-tocopherol) , may also be included in the low calorie fat-like material used for infusion. Additionally, other desired additives such as texturizers may be included in the fat-like material used for infusion when infusion is carried out at low temperatures.

Infusion contact between roasted, partially defatted nuts and low calorie fat-like material can be carried out in any number of ways. One technique is to immerse the roasted, partially defatted nuts in a bath of low calorie fat-like materials (e.g., quench the nuts while still hot from roasting) , causing the nuts to absorb relatively large amounts of the fat-like material. Alternatively, where it is desired to limit the amount of fat-like material infused into the nuts, giving them a less oily character, they can be contacted with a relatively small quantity of fat-like material by spraying, tumbling, or any conventional coating technique. As a result, only that limited quantity of fatty material is capable of being infused into the nuts. The quantity of fat-like material utilized in the latter embodiment is 5-15, preferably 10, pounds per 100 pounds of nuts. Except when incorporating heat sensitive substances in the fat-like material, the nuts can be contacted with fatty material while still hot from roasting. Preferably, the low calorie fat-like material is relatively cool (i.e., 40 to 150°F, preferably 65-110°F) during such contact.

Preferably, infusion is achieved by differential pressure. This is carried out by drawing a vacuum on the roasted, partially defatted nuts prior to contact with the low calorie fat-like material. Vacuum should be drawn at a level of 10-27 in. Hg. While the nuts are still under vacuum, they are contacted with the fat-like material, preferably by spraying. The vacuum is then broken, and the fat-like material infuses into the nuts, aided by the higher pressure around them.

When infusing with low calorie fat-like materials which are solid at room temperature, it is necessary to melt them by heating prior to infusion. The liquefied fat-like material is contacted with the partially defatted nuts, as discussed above, and the nuts are then allowed to cool. As the nuts cool, the infused low calorie fat-like material resolidifies, imparting a crunchy texture to the partially defatted nuts. After infusion, the nuts may be coated with various powdered flavoring agents such as allspice, cinnamon, clove, caraway, bay, sage, ginger, basil, and the like. These materials can be employed alone or with condiments such as salt, pepper, monosodium glutamate, and the like. In addition, texturizers such as, glycerine and polypropylene glycol, and binders such as, natural gums, dextrins, gelatin, sugars, and the like, can be applied.

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

EXAMPLE I

One hundred grams of raw defatted peanuts with a moisture content of 5.37% were mixed with 1.8 grams of tap water. The mixture was allowed to equilibrate for six hours to impart a 7.53% moisture content to the peanuts. The moistened nuts were then divided into two samples (i.e., A and B) and both were roasted at 302° F for 20 minutes in a forced air "Precision Lab Roaster/Oven" made by Precision Scientific, Inc.. After roasting. Sample A was quenched in 10 grams of dilauryl myristoyl malate which had been heated to 140° F, removed from the quenching liquid, and cooled. Sample B was cooled without quenching. A comparison between the weight of Sample A after roasting but before quenching and its weight after quenching indicated that the infusion of dilauryl myristoyl malate increased the weight of the peanuts by about 23%.

When the texture of peanuts from Sample A and Sample B were compared by chewing. Sample A peanuts had a crunch profile much more like full fat, roasted peanuts than those of Sample B. More particularly, Sample B peanuts had an initial crunch but then rapidly became soggy, while Sample A peanuts stayed crunchy throughout chewing just like full fat roasted peanuts.

EXAMPLE II

One thousand grams of raw defatted nuts were wetted with 17.5 grams of water for 12 hours to permit the nut moisture to equilibrate at 7.21%. The peanuts were then air roasted in the same manner as in Example I. Thirteen and three-tenths grams of dilauryl myristoyl malate, which was heated to 140° F, was sprayed on 40.13 grams of the peanuts, while the hot nuts were rotated in a barrel. The peanuts treated in this fashion weighed 49.9 grams, indicating that infusion with dilauryl myristoyl malate increased the weight of the peanuts by 19.6%. The infused peanuts were then allowed to set for 12 hours until the dilauryl myristoyl malate had time to resolidify.

When peanuts infused with dilauryl myristoyl malate were chewed and compared with peanuts which had been similarly treated but not infused, the former had a longer-lasting crunchy character. EXAMPLE III

The procedure of Example II was repeated through the roasting step. A 30-gram sample of the roasted, defatted peanuts was then sprayed with 8.82 grams of dimyristyl myristoyl malate in the manner described in Example II. As a result of infusion, the weight of the peanuts had increased to 35.77 grams, indicating that the dimyristyl myristoyl malate had increased their weight by 16.1%. The infused peanuts were then allowed to age for 12 hours until the dimyristyl myristoyl malate had the time to resolidify.

When peanuts infused with dimyristyl myristoyl malate were chewed and compared with peanuts which had been similarly treated but not infused, the former had a longer-lasting crunchy character.

EXAMPLE IV

The process of Example II was repeated except that dimyristyl myristoyl malate was replaced with 1,1,1- tris-hydroxymethylethane trimyristate for infusion. Weight measurements indicated that infusion increased the weight of the infused nuts by 21.18%.

When peanuts infused with 1,1,1- tris-hydroxymethylethane trimyristate' were chewed and compared with peanuts which had been similarly treated except for being infused, the former had a longer-lasting crunchy character.

Although the invention has been described in detail for the purpose of illustration, it is understood that such detail is solely for that purpose, and variations can be made therein by those skilled in the art without departing from the spirit and scope of the invention which is defined by the following claims.

Claims

WHAT IS CLAIMED:

1. A process of producing low calorie nuts with the organoleptic character of full fat nuts comprising: pressing raw nuts so that they are partially defatted; roasting the partially defatted nuts; and contacting the roasted, partially defatted nuts with a liquefied, low calorie fat-like material, whereby the low calorie fat-like material is infused into the roasted, partially defatted nuts.

2. A process according to claim 1, wherein the low calorie fat-like material is selected from the group consisting of carboxy/carboxylate esters, sucrose polyesters, esters with a neopentyl nucleus, branched chain fatty acid triglycerides, glycol ethers, polycarboxylic acid esters, neopentyl alcohol esters, silicone oils/siloxanes, and dicarboxylic acid esters, poorly absorbed triglyceride-derived fats, highly esterified polyglycerol esters, acetin fats, plant sterol esters, polyoxyethylene esters, esterified propoxylated or ethoxylated glycerol or the like, jojoba esters, mono/diglycerides of fatty acids, low caloric alkyl glycoside fat substitutes, tristearin, tripalmitan, esterified castor oil, alpha-acylated glycerides, triglycerides with combinations of saturated medium chain fatty acids, saturated long chain fatty acids, and unsaturated long chain fatty acids, mono/diglycerides of short-chain dibasic acids, complex linked esters, complex polyol esters with fatty acid residues and/or residues of esters or ethers having an acid function, ether bridged polyesters, diol lipid analogues, cyclohexyl diol diesters, long chain diol diesters, acylated amino acid derivatives, primary amide esters, polyvinyl alcohols esterified with fatty acids, thio ester derivatives, alcohol amine esters, alkoxy/carboxylate esters, secondary amide esters, extended esters, partially digestible sucrose, and triglycerides derived from glycerol esterified with long chain fatty acids at the 1- and 3- positions and a short chain acid at the 2- position, and mixtures thereof.

3. A process according to claim 2, wherein the low calorie fat-like material is selected from the group consisting of carboxy/carboxylate esters, esterified trishydroxymethyl compounds, complex linked esters, complex polyol esters with fatty acid residues and/or residues of esters or ethers having an acid function, ether bridged polyesters, diol lipid analogues, cyclohexyl diol diesters, long chain diol diesters, acylated amino acid derivatives, primary amide esters, polyvinyl alcohols esterified with fatty acids, thio ester derivatives, alcohol amine esters, alkoxy/carboxylate esters, secondary amide esters, extended esters, partially digestible sucrose, and triglycerides derived from glycerol esterified with long chain fatty acids at the 1- and 3- positions and a short chain acid at the 2- position, and mixtures thereof.

4. A process according to claim 2, wherein the low calorie fat-like material is present during said contacting in an infusion liquid which further comprises a liquid triglyceride fat.

5. A process according to claim 2, wherein the low calorie fat-like material is present during said contacting in an infusion liquid which consists essentially of the low calorie fat-like material.

6. A process according to claim 1, wherein said pressing is mechanically effected to reduce the oil content of the raw nuts by 40 to 52%.

7. A process according to claim 1, wherein said roasting is with hot air at a temperature of 275 to 400°F, and said process further comprises: contacting the nuts with water at a level of 3 to 7 pounds of water per 100 pounds of nuts prior to said roasting.

8. A process according to claim 7, wherein the roasted, partially defatted nuts have a moisture content of less than 3% and are roasted to a color level of 60 to 95 measured on an Agtron color photometer employed in the green mode with 12% and 33% plates defining the reading scale.

9. A process according to claim 1, wherein said roasting is carried out in a fatty material.

10. A process according to claim 9, wherein the fatty material comprises a low calorie fat-like material. -35-

11. A process of producing low calorie nuts with the organoleptic character of full fat nuts comprising: contacting roasted, partially defatted nuts with a liquefied, low calorie fat-like material, whereby the low calorie f t-like material is infused into the roasted, partially defatted nuts.

12. A process according to claim 11, wherein the low calorie fat-like material is selected from the group consisting of carboxy/carboxylate esters, sucrose polyesters, esters with a neopentyl nucleus, branched chain fatty acid triglycerides, glycol ethers, polycarboxylic acid esters, neopentyl alcohol esters, silicone oils/siloxanes, and dicarboxylic acid esters, poorly absorbed triglyceride-derived fats, highly esterified polyglycerol esters, acetin fats, plant sterol esters, polyoxyethylene esters, esterified propoxylated or ethoxylated glycerol or the like, jojoba esters, mono/diglycerides of fatty acids, low caloric alkyl glycoside fat substitutes, tristearin, tripal itan, esterified castor oil, alpha-acylated glycerides, triglycerides with combinations of saturated medium chain fatty acids, saturated long chain fatty acids, and unsaturated long chain fatty acids, mono/diglycerides of short-chain dibasic acids, complex linked esters, complex polyol esters with fatty acid residues and/or residues of esters or ethers having an acid function, ether bridged polyesters, diol lipid analogues, cyclohexyl diol diesters, long chain diol diesters, acylated amino acid derivatives, primary amide esters, polyvinyl alcohols esterified with fatty acids, thio ester derivatives, alcohol amine esters. alkoxy/carboxylate esters, secondary amide esters, extended esters, partially digestible sucrose, and triglycerides derived from glycerol esterified with long chain fatty acids at the 1- and 3- positions and a short chain acid at the 2- position, and mixtures thereof.

13. A process according to claim 12, wherein the low calorie fat-like material is selected from the group consisting of carboxy/carboxylate esters, ^' esterified trishydroxymethyl compounds, complex linked esters, complex polyol esters with fatty acid residues and/or residues of esters or ethers having an acid function, ether bridged polyesters, diol lipid analogues, cyclohexyl diol diesters, long chain diol diesters, acylated amino acid derivatives, primary amide esters, polyvinyl alcohols esterified with fatty acids, thio ester derivatives, alcohol amine esters, alkoxy/carboxylate esters, secondary amide esters, extended esters, partially digestible sucrose, and triglycerides derived from glycerol esterified with long chain fatty acids at the 1- and 3- positions and a short chain acid at the 2- position, and mixtures thereof.

14. A process according to claim 13, wherein the low calorie fat-like material comprises one or more carboxy/carboxylate esters.

15. A process according to claim 14, wherein the low calorie fat-like material is a dialkoxy acylmalate.

16. A process according to claim 14, wherein the low calorie fat-like material is a dialkoxy di{acyl)tartrate.

17. A process according to claim 12, wherein the low calorie fat-like material comprises one or more sucrose polyesters.

18. A process according to claim 13, wherein the low calorie fat-like material comprises one or more monomeric, esterified trishydroxymethyl compounds.

19. A process according to claim 12, wherein the low calorie fat-like material is a solid at room temperature and a liquid at below 150° F.

20. A process according to claim 12, wherein the low calorie fat-like material is present during said contacting in an infusion liquid which further comprises a fully digestible triglyceride fat.

21. A process according to claim 12, wherein the low calorie fat-like material is present during said contacting in an infusion liquid which consists essentially of the low calorie fat-like material.

22. A process according to claim 11, wherein the low calorie fat-like material is present during said contacting in an infusion liquid which further comprises additives selected from the group consisting of vitamins, flavoring agents, and sweeteners.

23. A process according to claim 11, wherein the nuts are selected from the group consisting of peanuts, cashews, almonds, Brazil nuts, filberts, pecans, walnuts, and mixtures thereof.

24. A process according to claim 22, wherein the nuts are peanuts.

25. A process according to claim 11, wherein said contacting is at a level of 5 to 15 pounds of the low calorie fat-like material per 100 pounds of the nuts.

26. A process according to claim 11, wherein said contacting occurs while the nuts are hot, and the low calorie fat-like material is at a temperature of 40 to 150°F.

27. A process according to claim 11, wherein said contacting is carried out by immersing the nuts in a bath of the low calorie fat-like material.

28. A process according to claim 11, wherein said contacting comprises: drawing a vacuum on the nuts; contacting the nuts, while still under vacuum, with the low calorie fat-like material; and returning the nuts to atmospheric pressure while in contact with the low calorie fat-like material.

29. A process according to claim 11 further comprising: coating the infused nuts with particulate flavoring agents, texturizers, binders, sweeteners, or mixtures thereof.

30. A low calorie nut with the organoleptic character of a full fat nut comprising: a roasted, partially defatted nut infused with a liquefied low calorie fat-like material containing infusant.

31. A low calorie nut according to claim 30, wherein the low calorie fat-like material is selected from the group consisting of carboxy/carboxylate esters, sucrose polyesters, esters with a neopentyl nucleus, branched chain fatty acid triglycerides, glycol ethers, polycarboxylic acid esters, neopentyl alcohol esters, silicone oils/siloxanes, and dicarboxylic acid esters, poorly absorbed triglyceride-derived fats, highly esterified polyglyσerol esters, acetin fats, plant sterol esters, polyoxyethylene esters, esterified propoxylated or ethoxylated glycerol or the like, jojoba esters, mono/diglycerides of fatty acids, low caloric alkyl glycoside fat substitutes, tristearin, tripalmitan, esterified castor oil, alpha-acylated glycerides, triglycerides with combinations of saturated medium chain fatty acids, saturated long chain fatty acids, and unsaturated long chain fatty acids, mono/diglycerides of short-chain dibasic acids, complex linked esters, complex polyol esters with fatty acid residues and/or residues of esters or ethers having an acid function, ether bridged polyesters, diol lipid analogues, cyclohexyl diol diesters, long chain diol diesters, acylated amino acid derivatives, primary amide esters, polyvinyl alcohols esterified with fatty acids, thio ester derivatives, alcohol amine esters, alkoxy/carboxylate esters, secondary amide esters, extended esters, partially digestible sucrose, and triglycerides derived from glycerol esterified with long chain fatty acids at the 1- and 3- positions and a short chain acid at the 2- position, and mixtures thereof.

32. A low calorie nut according to claim 31, wherein the low calorie fat-like material is selected from the group consisting of carboxy/carboxylate esters, esterified trishydroxymethyl compounds, complex linked esters, complex polyol esters with fatty acid residues and/or residues of esters or ethers having an acid function, ether bridged polyesters, diol lipid analogues, cyclohexyl diol diesters, long chain diol diesters, acylated amino acid derivatives, primary amide esters, polyvinyl alcohols esterified with fatty acids, thio ester derivatives, alcohol amine esters, alkoxy/carboxylate esters, secondary amide esters, extended esters, partially digestible sucrose, and triglycerides derived from glycerol esterified with long chain fatty acids at the 1- and 3- positions and a short chain acid at the 2- position, and mixtures thereof.

33. A low calorie nut according to claim 32, wherein the low calorie fat-like material comprises one or more carboxy/ carboxylate esters.

34. A low calorie nut according to claim 33, wherein the low calorie fat-like material is a dialkoxy aσylmalate.

35. A low calorie nut according to claim 33, wherein the low calorie fat-like material is a dialkoxy di(acy1)tartrate.

36. A low calorie nut according to claim 31, wherein the low calorie fat-like material comprises one or more sucrose polyesters.

37. A low calorie nut according to claim 32, wherein the low calorie fat-like material comprises one or more monomeric, esterified trishydroxmethyl compounds.

38. A low calorie nut according to claim 32, wherein the low calorie fat-like material is a solid at room temperature and a liquid at below 150° F.

39. A low calorie nut according to claim 32, wherein the low calorie fat-like material is mixed with a fully digestible liquid triglyceride fat.

40. A low calorie nut according to claim 32, wherein the infusant consists essentially of the low calorie fat-like material.

41. A low calorie nut according to claim 30, wherein the low calorie fat-like material is mixed with an additive selected from the group consisting of vitamins, flavoring agents, and sweeteners.

42. A low calorie nut according to claim 41, wherein the low calorie fat-like material is mixed with a nut flavor concentrate.

43. A low calorie nut according to claim 30, wherein the nut is selected from the group consisting of peanuts, cashews, almonds, Brazil nuts, filberts, pecans, walnuts, and mixtures thereof.

44. A low calorie nut according to claim 30 further comprising: a particulate coating surrounding the infused nut comprising flavoring agents, texturizers, binders, sweeteners, or mixtures thereof.