Food compositions containing reduced calorie fats and reduced calorie sugars

Fat-containing and sugar-containing food compositions which comprise: (1) from about 2 to about 98% of a fat component having from about 10 to 100% of certain reduced calorie fats, and (2) from about 2 to about 98% of a sugar component having from about 10 to about 100% of certain reduced calorie sugars are disclosed. Examples of such compositions include flavored confectionery fat products, such as chocolate-flavored candy bars, chocolate-flavored coatings for enrobed products and chocolate-flavored chips, baked good products, such as cakes, brownies and cookies, and emulsified oil products such as margarines and salad dressings.

TECHNICAL FIELD 
This application relates to food compositions containing certain reduced 
calorie fats and certain reduced calorie sugars. This application 
particularly relates to flavored confectionery fat products, baked good 
products and emulsified oil products which contain such fats and sugars. 
There are a variety of food products which contain both fats and sugars. 
For example, chocolate-flavored confectionery products comprise cocoa 
butter or a cocoa butter fat substitute, and sugar, typically in the form 
of sucrose. Other examples of such products are baked goods such as 
cookies, brownies and cakes and frozen desserts such as ice cream. 
The fat and sugar components in such products can provide a significant 
number of calories. In the case of fat, the caloric load is due to the 
triglycerides that are present. For example, a natural fat, such as corn 
oil, provides a caloric density of about 9 calories per gram. By 
comparison, vegetable protein provides only about 4 calories per gram. 
A number of solutions have been proposed for replacing the fat component in 
such products. For example, gums and other thickeners are typically used 
to replace a portion of the fat component by increasing the amount of 
water that is present. However, these substitutes often have a number of 
undesirable properties, particularly in the textural and flavor area. 
Accordingly, it would be desirable to substitute for higher calorie fats 
other materials which have reduced calories, but still provide the 
textural and flavor properties of fat. 
In the case of sugars, sucrose is often used in such products. It is well 
known that sucrose imparts a significant number of calories to such food 
products. The caloric density of sucrose is about 4 calories per gram. In 
addition, certain diseases, in particular diabetes, require the affected 
person to restrict their intake of sucrose and other sugars. 
A variety of high intensity, reduced calorie sweeteners have been developed 
to replace sugar. Prominent examples of such reduced calorie sweeteners 
are aspartame and acesulfame. While these materials can replace the 
sweetness component, they are totally incapable of providing the other 
functional properties of sugar. These other functional properties include 
water activity (a.sub.w) reduction, control of starch gelatinization 
temperature, and viscosity. 
A variety of bulking or bodying agents have been proposed to replace sugars 
to provide these other functional properties. These bulking agents include 
cellulosic derivatives such as carboxymethylcellulose, hydrocolloid gums 
and certain wholly or partially nondigestible carbohydrates. A prominent 
example of such partially nondigestible carbohydrates is the polyglucose 
derivative referred to as polydextrose. See U.S. Pat. No. 3,766,165 to 
Rennhard, issued Oct. 16, 1973, which discloses the use of polydextrose, 
and its related polyglucose derivatives, as non-nutritive carbohydrate 
substitutes in a variety of food products, including cakes, dietetic ice 
cream, low calorie salad dressings, chocolate coating formulations, 
whipped toppings and french salad dressings. 
Polydextrose does not behave like a simple sugar and particularly does not 
have the same baking properties as sugars. Instead, it functions more as a 
filler or viscosity controlling agent, much like starch dextrins. 
Polydextrose works very well in low water systems such as hard candies. 
However, in intermediate water containing baked goods systems such as 
brownies and cookies, polydextrose does not work very well. Polydextrose 
can also be used in high water systems such as cakes and ice creams, but 
requires strict formulation control. Accordingly, it would be desirable to 
have a reduced calorie substitute for sugar that provides its functional 
properties in a variety of food products without requiring strict 
formulation control. 
BACKGROUND ART 
A. The Use of Polydextrose as a Non-Nutritive Carbohydrate Bulking Agent in 
Chocolate and Other Fat-Containing Food Products 
U.S. Pat. No. 3,766,165 to Rennhard, issued Oct. 16, 1973, discloses the 
use of polydextrose and its related polyglucose derivatives as 
non-nutritive carbohydrate substitutes. Fat-containing food product uses 
specifically disclosed include cakes, dietetic ice cream, low calorie 
salad dressings, chocolate coating formulations, whipped toppings and 
french salad dressings. See also U.S. Pat. No. 3,876,794 to Rennhard, 
issued Apr. 8, 1975 for a similar disclosure. 
There are a number of other references which disclose the use of 
polydextrose in fat-containing food products. See, for example, Cridland, 
"Developments in Dietetic Chocolate," Confectionery Manufacturing & 
Marketing, (use of polydextrose as a low calorie bulking agent to replace 
sucrose in chocolate products); U.S. Pat. No. 4,810,516 to Kong-Chan, 
issued Mar. 7, 1989 (reduced calorie chocolate confections containing 
sucrose polyesters, artificial sweeteners such as aspartame and a wholly 
or partially digestible carbohydrate bulking agent such as polydextrose); 
U.S. Pat. No. 4,814,195 to Yokoyama et al, issued Mar. 21, 1989 (reduced 
calorie peanut butter products containing solid low calorie bulking 
agents, preferably polydextrose); U.S. Pat. No. 4,818,553 to Holscher et 
al, issued Apr. 4, 1989 (bakery products containing a water-in-oil 
emulsion shortening phase, flour, eggs, leavening agents and a low calorie 
bulking agent, preferably polydextrose, as a partial replacement for 
sucrose). 
B. Short Chain and Medium Chain Fatty Acid Triglycerides of 1-Monostearin 
and 1-Monobehenin 
Menz, "Polymorphism of Diacid Triglycerides of the Stearic Acid and Behenic 
Acid Series," Fette Seifen Anstrichmittel, Vol. 77, No. 5 (1975), pp. 
170-73, discloses a study of the polymorphic properties of 1-monostearin 
and 1-monobehenin which have been esterified with C.sub.2, C.sub.4, 
C.sub.6 or C.sub.8 short/medium chain saturated fatty acids. 
DISCLOSURE OF THE INVENTION 
The present invention relates to fat-containing and sugar-containing food 
compositions which comprise: (1) from about 2 to about 98% of a fat 
component having from about 10 to 100% of a certain reduced calorie fat; 
and (2) from about 2 to about 98% of a sugar component having from about 
10 to about 100% of a certain reduced calorie sugar. The reduced calorie 
fat present in this fat component comprises: at least about 15% reduced 
calorie triglycerides selected from the group consisting of MML, MLM, MLL 
and LML triglycerides, and mixtures thereof, wherein M=fatty acids 
selected from the group consisting of C.sub.6 to C.sub.10 saturated fatty 
acids, and mixtures thereof, and L=fatty acids selected from the group 
consisting of C.sub.17 to C.sub.26 saturated fatty acids, and mixtures 
thereof, and wherein the fat has the following fatty acid composition by 
weight percent: 
(a) from about 15 to about 70% C.sub.6 to C.sub.10 saturated fatty acids; 
and 
(b) from about 10 to about 70% C.sub.17 to C.sub.26 saturated fatty acids. 
The reduced calorie sugars present in the sugar component are the 
5-C-hydroxymethyl hexose compounds and their derivatives. 
All weights, ratios, and percentages herein are by weight unless otherwise 
specified. 
A. REDUCED CALORIE FAT 
The reduced calorie fats used in the present invention comprise at least 
about 15% reduced calorie triglycerides selected from the group consisting 
of MML, MLM, MLL, and LML triglycerides, and mixtures thereof; wherein 
M=fatty acids selected from the group consisting of C.sub.6 to C.sub.10 
saturated fatty acids, and mixtures thereof, and L=fatty acids selected 
from the group consisting of C.sub.17 to C.sub.26 saturated fatty acids, 
and mixtures thereof; and wherein the fat has the following fatty acid 
composition by weight percent: 
(a) from about 15 to about 70% C.sub.6 to C.sub.10 saturated fatty acids; 
and 
(b) from about 10 to about 70% C.sub.17 to C.sub.26 saturated fatty acids. 
Preferred reduced calorie fats having fatty acid compositions which 
comprise: 
(c) not more than about 10% fatty acids selected from the group consisting 
of C.sub.12:0 and C.sub.14:0, and mixtures thereof; 
(d) not more than about 20% fatty acids selected from the group consisting 
of C.sub.18:1, C.sub.18:2, C.sub.18:3, and mixtures thereof; and 
(e) not more than 4% C.sub.18:2 fatty acids. See U.S. application Ser. No. 
329,620 to Paul Seiden, filed Mar. 28, 1989 (herein incorporated by 
reference), which discloses these reduced calorie fats and their 
preparation. 
By "medium chain fatty acids," as used herein, is meant C.sub.6:0 
(caproic), C.sub.8:0 (caprylic), or C.sub.10:0 (capric) fatty acids, or 
mixtures thereof. The C.sub.7 and C.sub.9 saturated fatty acids are not 
commonly found, but they are not excluded from the possible medium chain 
fatty acids. The present medium chain fatty acids do not include lauric 
acid (C.sub.12:0), sometimes referred to in the art as a medium chain 
fatty acid. 
By "long chain fatty acids," as used herein, is meant C.sub.17:0 
(margaric), C.sub.18:0 (stearic), C.sub.19:0 (nonadecylic), C.sub.20:0 
(arachidic), C.sub.21:0 (heneicosanoic), C.sub.22:0 (behenic), C.sub.23:0 
(tricosanoic), C.sub.24:0 (lignoceric), C.sub.25:0 (pentacosanoic), or 
C.sub.26:0 (cerotic) fatty acids, or mixtures thereof. 
In the above listing of fatty acid moieties, the common name of the fatty 
acid is given following its C.sub.x:y designation (wherein x is the number 
of carbon atoms, and y is the number of double bonds). 
By "MML," as used herein, is meant a triglyceride containing a long chain 
fatty acid in the #1 or #3 position (an end position) with two medium 
chain fatty acids in the remaining two positions. (The absorption of long 
chain saturated fatty acids is generally reduced in the end positions.) 
Similarly, "MLM" represents a triglyceride with a long chain fatty acid in 
the #2 position (the middle position) and two medium chain fatty acids in 
the #1 and #3 positions, "MLL" represents a triglyceride with a medium 
chain fatty acid in the #1 or #3 position and two long chain fatty acids 
in the remaining two positions, and "LML" represents a triglyceride with a 
medium chain fatty acid in the #2 position and two long chain fatty acids 
in the #1 and #3 positions. 
The key to these reduced calorie fats is their combination of particular 
long chain fatty acid moieties with medium chain fatty acid moieties. The 
medium chain fatty acids lower the melting point of the fats, and 
different fatty acid combinations can be used to control the fats' 
physical properties for specific food applications. This results in a 
good-tasting fat having good mouthmelt, texture and flavor display. 
Moreover, because they do not taste waxy, these reduced calorie fats can be 
used in a wide variety of food products, and at higher concentrations in 
the products to afford a greater calorie reduction. This is in contrast to 
the more limited use of a more waxy-tasting triglyceride, e.g., a 
triglyceride containing lauric acid and long chain fatty acids. This 
nonwaxy taste benefit is particularly evident in chocolate products made 
with preferred reduced calorie fats. As measured by differential scanning 
calorimetry (DSC), chocolate products containing these preferred fats are 
completely melted at a temperature of from 94.degree. to 96.degree. F. 
(34.4.degree. to 35.6.degree. C.). Most of the melting of these chocolate 
products also occurs in the fairly narrow temperature range of from 
80.degree. to 94.degree. F. (26.7.degree. to 34.4.degree. C.). 
Another advantage of these reduced calorie fats is that they typically 
contain only limited amounts of saturated C.sub.12 to C.sub.16 fatty 
acids. Ingestion of large amounts of these fatty acids is known to promote 
hypercholesterolemia. 
These reduced calorie fats also provide some of the benefits of medium 
chain triglycerides. For example, the medium chain fatty acids are readily 
hydrolyzed from the triglycerides. These hydrolyzed medium chain fatty 
acids are absorbed and then transported directly to the liver (via the 
hepatic portal vein) where they are extensively oxidized to provide a 
rapid energy source. 
These reduced calorie fats permit an at least about 10% reduction in 
calories, and preferably an at least about 30% reduction in calories over 
typical chain length triglycerides (i.e., corn oil), and usually between 
about 20% and 50% reduction in calories. 
For the purposes of the present invention, the reduction in calories 
provided by these reduced calorie fats is based on the net energy gain (in 
Kcal) of rats that have ingested a diet containing the reduced calorie 
fats, relative to the net energy gain (in Kcal) of rats that have ingested 
an identical diet, but containing corn oil instead of the reduced calorie 
fat. The test diets used are nutritionally adequate to support both 
maintenance and growth of the rats. Total food intake and fat/oil intake 
are also matched between the two diet groups so that differences in net 
carcass energy gain are due entirely to the utilizable energy content of 
the fat/oil. "Net energy gain" is based on the total carcass energy (in 
Kcal) of the rat fed the test diet for some period of time (usually 4 
weeks), reduced by the mean starting carcass energy (in Kcal) determined 
from a study of a different group of rats of the same sex, strain, and 
similar body weight fed a test diet that does not contain the fat/oil. 
"Total carcass energy" is determined by the dry carcass energy per gram 
(Kcal per gram) multiplied by the dry weight of the carcass (in grams). 
"Carcass energy per gram" is based on the carcass energy (in Kcal) as 
determined by bomb calorimetry of a homogeneous sample of the total dry 
carcass. All of these energy values are the average of a representative 
sample of rats (i.e., 10 rats). 
These reduced calorie fats will preferably contain not more than about 5%, 
and most preferably not more than about 0.5%, C.sub.6:0 fatty acid. It is 
also preferred that the fat contain not more than about 20% saturated 
C.sub.24 to C.sub.26 fatty acids, and most preferably not more than about 
10%. Preferred reduced calorie fats of the present invention comprise from 
about 30 to about 60% C.sub.8 to C.sub.10 saturated fatty acids and from 
about 30 to about 60% C.sub.18 to C.sub.22 saturated fatty acids. 
These reduced calorie fats can contain limited amounts of other fatty acids 
besides medium and long chain fatty acids, without losing the desired 
benefits. Palmitic acid (C.sub.16:0) is about 95% absorbed by the body, 
while the longer chain fatty acids are less absorbed. Therefore, it is 
preferred that these reduced calorie fats contain not more than about 10% 
C.sub.16:0 fatty acid. These reduced calorie fats will also preferably 
contain not more than about 6% fatty acids selected from the group 
consisting of C.sub.18:1, C.sub.18:2, C.sub.18:3, and mixtures thereof, 
more preferably not more than about 1%, and most preferably not more than 
about 0.5%. Preferred reduced calorie fats also contain not more than 
about 3%, and more preferably not more than about 1% fatty acids selected 
from the group consisting of C.sub.12:0 (lauric) and C.sub.14:0 
(myristic), and mixtures thereof. Lauric and myristic acid result in more 
fat deposition than medium chain fatty acids. 
For optimum taste and calorie reduction, it is also preferred that these 
reduced calorie fats comprise at least about 30% of the triglycerides 
containing combinations of medium and long chain fatty acids (i.e., MML, 
MLM, MLL and LML triglycerides), more preferably at least about 50% of 
these triglycerides, and most preferably at least about 80% of these 
triglycerides. Preferred reduced calorie fats comprise at least about 10% 
of a mixture of MML and MLM triglycerides, more preferably at least about 
35% of such combined triglycerides, and most preferably at least about 70% 
of such combined triglycerides. Preferred reduced calorie fats also 
comprise not more than about 40% combined MLL and LML triglycerides, more 
preferably not more than about 20% combined MLL and LML triglycerides, and 
most preferably not more than about 5% combined MLL and LML triglycerides. 
For most uses, these preferred reduced calorie fats also comprise 
minimized levels of MMM triglycerides and LLL triglycerides. By "MMM," as 
used herein, is meant a triglyceride containing medium chain saturated 
fatty acid residues at all three positions. Similarly, "LLL" represents a 
triglyceride containing long chain saturated fatty acid residues at all 
three positions. These preferred reduced calorie fats comprise not more 
than about 15%, more preferably not more than about 10%, and most 
preferably not more than about 5% MMM triglycerides. These preferred 
reduced calorie fats also comprise not more than about 5%, more preferably 
not more than about 2%, and most preferably not more than about 1% LLL 
triglycerides. However, for ice creams and ice cream coatings, these 
reduced calorie fats preferably comprise from about 10 to about 15% MMM 
triglycerides. 
Certain of these reduced calorie fats are particularly preferred for 
chocolate and other confectionery products. These particularly preferred 
reduced calorie fats comprise at least about 85% of a mixture of MML and 
MLM triglycerides, more preferably at least about 90% of such combined 
triglycerides, and most preferably at least about 94% of such combined 
triglycerides. These preferred reduced calorie fats also comprise no more 
than about 5% combined MLL and LML triglycerides, more preferably no more 
than about 2% MLL and LML triglycerides, and most preferably no more than 
about 1% combined MLL and LML triglycerides. These particularly preferred 
reduced calorie fats further comprise no more than about 4%, preferably no 
more than about 2% and most preferably no more than about 1% MMM 
triglycerides, and no more than about 2%, preferably no more than about 1% 
and most preferably no more than about 0.5% LLL triglycerides. 
These preferred fats for chocolate and other confectionery products also 
have the following preferred and most preferred carbon number profiles 
(CNP): 
______________________________________ 
MOST 
CNP PREFERRED (%) PREFERRED (%) 
______________________________________ 
32 or lower &lt;3 &lt;1 
34 &lt;2 &lt;1 
36 &lt;4 &lt;2 
38 10-40 10-30 
40 35-60 45-55 
42 15-40 25-35 
44 &lt;5 &lt;1 
46 &lt;1 &lt;0.6 
48 &lt;0.8 &lt;0.6 
50 &lt;0.6 &lt;0.5 
52 &lt;0.4 &lt;0.3 
54 or higher 
&lt;0.9 &lt;0.4 
______________________________________ 
The triglycerides used in these reduced calorie fats can be prepared by a 
wide variety of techniques such as: 
(a) random rearrangement of long chain triglycerides (e.g. tristearin or 
tribehenin) and medium chain triglycerides; 
(b) esterification of glycerol with a blend of the corresponding fatty 
acids; 
(c) transesterification of a blend of medium and long chain fatty acid 
methyl esters with glycerol; 
(d) transesterification of long chain fatty acid glycerol esters (e.g., 
glyceryl behenate) with medium chain triglycerides; and 
(e) esterification of long chain fatty acid monoglycerides (e.g. 
monostearin or monobehenin) with medium chain fatty acids or the 
respective anhydrides. See U.S. application Ser. No. 452,877, to Bernard 
W. Kluesener, Gordon K. Stipp and David K. Yang, filed Dec. 19, 1989 (P&G 
Case 4073), entitled "Selective Esterification of Long Chain Fatty Acid 
Monoglycerides with Medium Chain Fatty Acids," especially Examples 1 and 
3, and U.S. application Ser. No. 452,923, to Gordon K. Stipp and Bernard 
W. Kluesener, filed Dec. 19, 1989 (P&G Case 4074), entitled "Selective 
Esterification of Long Chain Fatty Acid Monoglycerides with Medium Chain 
Fatty Acid Anhydrides," especially Examples 1 and 7 (herein incorporated 
by reference). 
Random rearrangement of triglycerides is well-known in the art, as is the 
esterification of glycerol with fatty acids. For discussions on these 
subjects, see Hamilton et al., Fats and Oils: Chemistry and Technology, 
pp. 93-96, Applied Science Publishers Ltd., London (1980), and Swern, 
Bailey's Industrial Oil and Fat Products, 3d ed., pp. 941-943 and 958-965 
(1964), both disclosures incorporated by reference herein. 
Transesterification is also discussed generally in Bailey's at pp. 
958-963. 
Fatty acids per se or naturally occurring fats and oils can serve as 
sources of fatty acids for preparing the reduced calorie triglycerides. 
For example, hydrogenated soybean oil and hydrogenated high erucic acid 
rapeseed oil are good sources of stearic and behenic acid, respectively. 
Odd chain length long chain saturated fatty acids can be derived from 
certain marine oils. Medium chain saturated fatty acids can be obtained 
from coconut, palm kernel, or babassu oils. They can also be obtained from 
commercial medium chain triglycerides, such as the Captex 300 brand sold 
by Capital City Products of Columbus, Ohio. 
Tribehenin, useful for making the present triglycerides, can be made from 
behenic acid or from fractionated methyl behenate by esterification of the 
acid, or by transesterification of the methyl behenate with glycerol. More 
importantly, blends of behenic acid and medium chain fatty acids can be 
esterified with glycerol. Other long chain fatty acids (C.sub.18, 
C.sub.20, etc.) can be part of the process. Similarly, methyl ester blends 
can also be interesterified with glycerol. 
These reduced calorie fats are generally made by blending the 
above-described triglycerides with additional fat or oil ingredients. 
However, the invention is not limited by the method of preparation; other 
methods known to the art for making fats or oils can also be used. The 
fats can be refined, bleached, deodorized, or processed in other ways not 
inconsistent with the purposes of the invention. 
These reduced calorie fats can be modified to satisfy specific product 
performance requirements by additional fractionation. Solvent and 
non-solvent crystal fractionation or fractional distillation methods (e.g. 
molecular distillation as described below) can be applied to optimize 
performance. Standard fractionation methods are discussed in Applewhite, 
Bailey's Industrial Oil and Fat Products, Vol. 3, 4th ed. (1985), pp. 
1-39, John Wiley & Sons, New York, incorporated by reference herein. 
Fractional distillation of these reduced calorie fats is not limited to 
molecular distillation, but can also include conventional distillation 
(continuous or batch). After synthesis of the fats, it is common to use a 
conventional batch distillation technique to remove most of the excess 
medium chain triglycerides, and then continue with molecular distillation. 
The vacuum requirements are not as strict, and the temperature used can be 
higher in conventional distillation versus molecular distillation. The 
conventional distillation temperature is generally between 405.degree. F. 
(207.degree. C.) and 515.degree. F. (268.3.degree. C.). The absolute 
pressure is less than 8 mm Hg, more preferably less than 2 mm Hg. The 
distillation is aided by sparging with steam, nitrogen or other inert gas 
(e.g., CO.sub.2). The distillation is carried out to remove part of the 
excess MMM triglycerides, most of the excess MMM triglycerides, or to 
distill also the mono-long chain (MLM and MML) components. 
Crystal fractionation of the fats can be carried out with and without 
solvents, with and without agitation. The crystal fractionation can be 
repeated several times. Crystal fractionation is particularly effective to 
remove high melters. Fractionation of behenic MCT without solvents can be 
used to remove carbon number 50 and 52 MLL and LML components, which in 
turn alters the melting profile of the fat. 
B. REDUCED CALORIE SUGARS 
The reduced calorie sugars used in the present invention are the 
5-C-hydroxymethyl hexose compounds and their derivatives. See U.S. 
application Ser. No. 339,531 to Adam W. Mazur, filed Apr. 20, 1989 (herein 
incorporated by reference), which discloses these reduced calorie sugars 
and especially the Examples for their synthesis and U.S. application Ser. 
No. 337,725 to Adam W. Mazur, George D. Hiler, Jr., Gordon K. Stipp and 
Bernard K. Kluesener, filed Apr. 17, 1989 (herein incorporated by 
reference), for an alternative synthesis of the 5-C-hydroxymethyl 
aldohexoses. 
The term "hexose" means a sugar containing six carbons. This term 
encompasses both aldehyde containing hexoses (aldohexoses) and ketone 
containing hexoses (ketohexoses). 
The term "aldohexoses" refers to the group of sugars whose molecule 
contains six carbon atoms, one aldehyde group and five alcohol groups. The 
sixteen stereoisomers of the aldohexose series are D-allose, D-altrose, 
D-glucose, D-mannose, D-gulose, D-idose, D-galactose, D-talose, L-allose, 
L-altrose, L-glucose, L-mannose, L-gulose, L-idose, L-galactose and 
L-talose. These sugars exist in solution as an equilibrium mixture of 
several "tautomeric forms": a pyran-ring form; a furan-ring form; or a 
straight-chain aldehyde form. Tautomeric forms of D-glucose: 
##STR1## 
Aldohexoses may also occur in an .alpha. or .beta. anomeric configuration, 
depending on the position of the C-1 hydroxyl group. Examples are: 
##STR2## 
The term "ketohexose" refers to the group of sugars which contain six 
carbon atoms, one ketone group and five alcohol groups. The eight 
stereoisomers are D- and L- isomers of psicose, fructose, sorbose and 
tagatose. Like the aldohexoses, these ketohexoses can exist in solution as 
an equilibrium mixture of several "tautomeric forms": pyran-ring; a furan 
ring and a straight chain ketone form. 
The term "sugar derivatives" as used herein refer to the 5-C-hydroxylmethyl 
derivatives of the hexoses and their stereoisomers and polymers. 
The term "polyol" includes all polyhydric alcohols (i.e., those compounds 
of the general formula CH.sub.2 OH(CHOH).sub.n CH.sub.2 OH, where n may be 
from 0 to 5.). Glycerol contains three hydroxyl groups. Those with more 
than three are called sugar alcohols. 
The 5-C-hydroxymethylaldohexose monosaccharides include the following: 
##STR3## 
The preferred embodiments of the straight-chain 5-C-hydroxymethylaldohexose 
compounds are 5-C-hydroxymethyl derivatives of galactose, glucose, and 
mannose. Due to the relative ease of synthesizing galactose-based 
compounds, 5-C-hydroxymethyl derivative of D-galactose is the most 
preferred compound. 
##STR4## 
The preferred embodiments of the 5-C-hydroxymethylaldohexopyranose 
compounds are 5-C-hydroxymethyl derivatives of galactopyranose, 
-glucopyranose, and -mannopyranose. Due to the relative ease of 
synthesizing galactose-based compounds, the 5-C-hydroxymethyl derivative 
of D-galactopyranose is the most preferred compound. 
##STR5## 
The preferred embodiments of the 5-C-hydroxymethylaldohexofuranose 
compounds are 5-C-hydroxymethyl derivatives of galactofuranose, 
-glucofuranose, and -mannofuranose. Due to the relative ease of 
synthesizing galactose-based compounds, the 5-C-hydroxymethyl derivative 
of D-galactofuranose is the most preferred embodiment. 
The 5-C-hydroxymethyl-aldohexose derivatives include: 
##STR6## 
The preferred embodiment of the 
1,6-anhydro-5-C-hydroxymethyl-.beta.-D-aldohexopyranose compounds is 
1,6-anhydro-5-C-hydroxymethyl-.beta.-D-galactopyranose. 
##STR7## 
The preferred embodiments of the 
1,6-anhydro-5-C-hydroxymethyl-.beta.-L-aldohexopyranose compounds are 
1,6-anhydro-5-C-hydroxymethyl-.beta.-L-altropyranose, -gulopyranose and 
idopyranose. The most preferred embodiment is 
1,6-anhydro-5-C-hydroxymethyl-.beta.-L-altropyranose. 
##STR8## 
where R is an alkyl group containing one to four carbon atoms. 
The preferred embodiments of alkyl 5-C-hydroxymethylaldohexopyranosides are 
ethyl and methyl 5-C-hydroxymethylaldohexopyranoside. The most preferred 
embodiment is ethyl D-galactopyranoside. 
##STR9## 
Where R is an alkyl group containing one to four carbon atoms. 
The preferred embodiments of alkyl 5-C-hydroxymethylaldohexofuranosides are 
ethyl and methyl 5-C-hydroxymethylaldohexofuranoside. The most preferred 
embodiment is ethyl 5-C-hydroxymethyl-L-arabinohexofuranoside. (VIII) 
Another derivative occurs when a polyol is covalently bound by a glycoside 
linkage to one of the above-mentioned 5-C-hydroxymethylated saccharides. 
Preferred embodiments of these compounds include: 
##STR10## 
Other monosaccharides based on the ketohexose derivatives are: 
##STR11## 
Preferred embodiments are 5-C-hydroxymethyl derivatives of fructose and 
sorbose, including alkyl glycosides, due to the availability of natural 
sugars. 
The monosaccharides discussed above (I-XI) may also be classified as simple 
sugars. Simple sugar linkages are the building blocks for di-, tri-, 
oligo- and polysaccharides. The novel di-, tri-, oligo- and 
polysaccharides of the present invention contain at least one simple sugar 
group (i.e., monosaccharides, monosaccharide derivatives) from the 
monosaccharides discussed above (I-XI) or their alditols covalently bound 
through glycoside linkages to one or more simple sugar or simple sugar 
groups through any of the glycoside acceptor carbon positions (i.e., C-1 
through C-7). The preferred glycoside linkages are through C-1 and C-4. 
Preferred disaccharides comprise at least one simple sugar linkage selected 
from the group consisting of 5-C-hydroxymethylaldohexose; 
1,6-anhydro-5-C-hydroxymethyl-.beta.-D-aldohexopyranose; 
1,6-anhydro-5-C-hydroxymethyl-.beta.-L-aldohexopyranose; 
5-C-hydroxymethylaldohexosyl polyol and alkyl 
5-C-hydroxymethylaldohexoside, where the alkyl group is selected from the 
group consisting of methyl, ethyl, propyl and isopropyl. 
Other preferred disaccharides comprise at least one simple sugar linkage 
selected from the group consisting of 5-C-hydroxymethylketohexose; 
5-C-hydroxymethylketohexosyl polyol and alkyl 
5-C-hydroxymethylketohexoside wherein the alkyl group is selected from the 
group of methyl, ethyl, propyl and isopropyl. 
The following disaccharides are most preferred compounds: 
##STR12## 
The preferred disaccharides containing 5-C-hydroxymethyl keto hexoses are: 
Ketohexose Derivatives Disaccharides 
##STR13## 
The preferred trisaccharides comprise at least one simple sugar linkage 
selected from the group consisting of 5-C-hydroxymethylaldohexose; 
1,6-anhydro-5-C-hydroxymethyl-.beta.-D-aldohexopyranose; 
1,6-anhydro-5-C-hydroxymethyl-.beta.-L-aldohexopyranose; 
5-C-hydroxymethylaldohexosyl polyol derivatives and alkyl 
5-C-hydroxymethyl-D-aldohexoside, where the alkyl is selected from the 
group consisting of methyl, ethyl, propyl and isopropyl. The most 
preferred trisaccharide embodiment is: 
##STR14## 
Preferred oligosaccharides comprise at least one simple sugar linkage 
selected from the group consisting of 5-C-hydroxymethylaldohexose; 
1,6-anhydro-5-C-hydroxymethyl-.beta.-D-aldohexopyranose; 
1,6-anhydro-5-C-hydroxymethyl-.beta.-L-aldohexopyranose; 
5-C-hydroxymethylaldohexosyl polyol derivatives and alkyl 
5-C-hydroxymethylaldohexoside, where the alkyl group is selected from the 
group consisting of methyl, ethyl, propyl and isopropyl. 
The most preferred oligosaccharide embodiment is: 
##STR15## 
The preferred polysaccharides comprise at least one simple sugar linkage 
selected from the group consisting of 5-C-hydroxymethylaldohexose; 
1,6-anhydro-5-C-hydroxymethyl-.beta.-D-aldohexopyranose; 
1,6-anhydro-5-C-hydroxymethyl-.beta.-L-aldohexopyranose; 
5-C-hydroxymethylaldohexosyl polyol derivatives; alkyl 
5-C-hydroxymethylaldohexoside, 5-C-hydroxymethylketohexose, 
5-C-hydroxylmethylketohexosyl polyol derivatives and alkyl 
5-C-hydroxymethylketohexoside where the alkyl is selected from the group 
consisting of methyl, ethyl, propyl and isopropyl. Finally, the most 
preferred polysaccharide embodiment is an arabinogalactan derivative 
wherein at least one D-galactosyl component is replaced with a 
5-C-hydroxymethyl-.alpha.-L-arabinopyranosyl group. 
C. FAT-CONTAINING AND SUGAR-CONTAINING FOOD COMPOSITIONS 
The fat-containing and sugar-containing food compositions of the present 
invention comprise: (1) from about 2 to about 98% (more typically from 
about 5 to about 95%) of a fat component; and (2) from about 2 to about 
98% (more typically from about 5 to about 95%) of a sugar component. The 
particular level of fat component and sugar component that can be present 
in these food compositions will vary greatly depending on the particular 
food product involved. For example, for baked good products, these 
compositions typically comprise from about 5 to about 30% fat component, 
and from about 20 to about 60% sugar component. In the case of flavored 
confectionery fat products, these compositions typically comprise from 
about 10 to about 45% fat component and from about 20 to about 90% sugar 
component. In the case of emulsified oil products, these compositions 
typically comprise from about 20 to about 90% fat component and from about 
2 to about 20% sugar component. 
The fat component of these food compositions comprises the reduced calorie 
fats described in part A of this application, in whole or in part. The 
particular level of reduced calorie fat which is present in this fat 
component can vary widely depending upon the food product involved, and 
particularly the reduced calorie benefits desired. Typically, the fat 
component comprises from about 10 to 100% reduced calorie fat. Preferably, 
the fat component comprises from about 30 to 100%, and most preferably 
from about 50 to 100%, reduced calorie fat. 
In addition to the reduced calorie fats, the fat component of the present 
invention can include other regular calorie fats and oils. Suitable 
sources of regular fats and oils include, but are not limited to: (1) 
vegetable fats and oils such as soybean, corn, sunflower, rapeseed, low 
erucic acid rapeseed, canola, cottonseed, olive, safflower, and sesame 
seed; (2) meat fats such as tallow or lard; (3) marine oils; (4) nut fats 
and oils such as coconut, palm, palm kernel, or peanut; (5) milkfat; (6) 
cocoa butter and cocoa butter substitutes such as shea, or illipe butter; 
and (7) synthetic fats. 
The sugar component of these food compositions comprises the reduced 
calorie sugars described in part B of this application, in whole or in 
part. The particular level of reduced calorie sugar that can be present in 
the carbohydrate component will depend upon the food product involved, and 
particularly the reduced calorie benefits desired. Typically, the sugar 
component comprises from about 10 to 100% reduced calorie sugars. 
Preferably, the sugar component comprises from about 30 to 100%, and most 
preferably from about 50 to 100%, reduced calorie sugars. 
In addition to the reduced calorie sugars, the sugar component of the 
present invention can include regular calorie sugars. These regular 
calorie sugars include, but are not limited to high maltose corn syrups, 
high fructose corn syrups, sucrose, fructose, glucose, and maltose, and 
sugar alcohols such as sorbitol, xylitol and mannitol, etc. 
The fat-containing and sugar-containing food compositions of the present 
invention are particularly suitable in formulating reduced calorie 
flavored confectionery fat compositions, particularly chocolate-flavored 
confectionery fat compositions, such as chocolate-flavored candy bars, 
chocolate-flavored coatings for enrobed products and chocolate-flavored 
chips. Particularly preferred examples of such flavored confectionery 
compositions comprise: 
a. a flavor enhancing amount of a flavor component; 
b. from about 25 to about 45% of a fat component comprising: 
(1) at least about 70% of a reduced calorie fat having: 
(a) at least about 85% combined MLM and MML triglycerides; 
(b) no more than about 5% combined MLL and LML triglycerides; 
(c) no more than about 2% LLL triglycerides; 
(d) no more than about 4% MMM triglycerides; 
(e) no more than about 7% other triglycerides; 
wherein M is a C.sub.6 to C.sub.10 saturated fatty acid residue and L is a 
C.sub.20 to C.sub.24 saturated fatty acid residue; 
(f) a fatty acid composition having: 
(i) from about 40 to about 60% combined C.sub.8 and C.sub.10 saturated 
fatty acids, 
(ii) a ratio of C.sub.8 to C.sub.10 saturated fatty acids of from about 
1:2.5 to about 2.5:1, 
(iii) from about 40 to about 60% behenic fatty acid, 
(2) up to about 15% milkfat; 
(3) up to about 20% cocoa butter; 
(4) no more than about 4% diglycerides; and 
c. from about 35 to about 60% of a sugar component having from about 50 to 
100% reduced calorie sugars as described in part B of this application. 
These compositions are preferably tempered according to the process 
disclosed in U.S. Pat. No. 4,888,196, to Ehrman et al, issued Dec. 19, 
1989, which is incorporated by reference. This process comprises the 
following steps: 
(I) forming a temperable flavored confectionery composition as defined 
above; 
(II) rapidly cooling the composition of step (I) to a temperature of about 
57.degree. F. or less so that the reduced calorie fat forms a sub .alpha. 
phase; 
(III) holding the cooled composition of step (II) at a temperature of about 
57.degree. F. or less for a period of time sufficient to form an effective 
amount of .beta.-3 crystals from a portion of the sub .alpha. phase of the 
reduced calorie fat; and 
(IV) after step (III), warming the cooled composition to a temperature in 
the range of from above about 57.degree. to about 72.degree. F. in a 
manner such that: (a) the remaining portion of the reduced calorie fat 
transforms into a stable .beta.-3 phase; and (b) the .beta.-3 phase formed 
does not melt. 
Certain of the reduced calorie fats, like cocoa butter, can be crystallized 
into a stable .beta.-3 phase. However, it has been found that the rate of 
crystallization of these reduced calorie fats into the .beta.-3 phase is 
extremely slow under standard tempering conditions used with cocoa 
butter-based chocolate products. This rate is sufficiently slow so as to 
make cocoa butter-type tempering of flavored confectionery compositions 
containing these reduced calorie fats commercially unattractive. 
Surprisingly, it has been found that tempering according to U.S. Pat. No. 
4,888,196 provides a commercially attractive process that is simpler than 
even the standard tempering conditions used with cocoa butter-based 
chocolate products. In particular, this tempering process can be carried 
out during the normal warehousing and distribution of the flavored 
confectionery product. These desirable results are achieved by taking 
advantage of the ability of these reduced calorie fats to transform into 
the desired stable .beta.-3 phase, via the less stable sub .alpha. phase. 
This transformation of the reduced calorie fats from the sub .alpha. phase 
to the stable .beta.-3 phase according to this tempering process occurs 
without undesired bloom formation. The resulting tempered products also 
have the desired firmness and mouthmelt of cocoa butter-based chocolate 
products. 
The fat-containing and sugar-containing food compositions of the present 
invention are also particularly suitable in the formulation of baked good 
products. As used herein, the term "baked goods" refers to all manner of 
foods which are cooked (i.e., prepared using heat). These baked goods 
include, but are not limited to, foods prepared using dry heat (i.e., a 
radiant or convection oven), fried foods, boiled foods and foods heated in 
a microwave oven. These baked goods can be in any form such as mixes, 
shelf-stable baked goods, and frozen baked goods. For baked good products 
of the present invention, the reduced calorie sugars used need to be the 
trisaccharide, oligosaccharide, polysaccharide, and preferably 
disaccharide versions of the 5-C-hydroxymethyl hexoses, and their 
derivatives. 
Suitable baked good products according to the present invention include, 
but are not limited to, cakes, brownies, muffins, bar cookies, wafers, 
biscuits, pastries, pies, piecrusts, and cookies, including sandwich 
cookies and chocolate chip cookies, particularly the storage-stable 
dual-textured cookies described in U.S. Pat. No. 4,455,333 to Hong et al, 
issued Jun. 19, 1984. These baked good products can contain food, creme, 
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 crust, baked farinaceous snack 
foods, and other baked salted snacks. 
Other examples of fat-containing and sugar-containing food compositions of 
the present invention include, but are not limited to: emulsified oil 
products such as margarines, salad dressings and mayonnaise-like products, 
ice cream and other frozen desserts, whipped toppings, frostings and 
icings. 
The food compositions of the present invention can also be fortified with 
vitamins and minerals, particularly the fat-soluble vitamins. U.S. Pat. 
No. 4,034,083 to Mattson, issued Jul. 5, 1977 (incorporated by reference 
herein) discloses polyol fatty acid polyesters fortified with fat-soluble 
vitamins. The fat-soluble vitamins include vitamin A, vitamin D, vitamin 
E, and vitamin K. Vitamin A is a fat-soluble alcohol of the formula 
C.sub.20 H.sub.29 OH. Natural vitamin A is usually found esterified with a 
fatty acid; metabolically active forms of vitamin A also include the 
corresponding aldehyde and acid. Vitamin D is a fat-soluble vitamin well 
known for use in the treatment and prevention of rickets and other 
skeletal disorders. Vitamin D comprises sterols, and there are at least 11 
sterols with vitamin D-type activity. Vitamin E (tocopherol) is a third 
fat-soluble vitamin which can be used in the present invention. Four 
different tocopherols have been identified (alpha, beta, gamma and delta), 
all of which are oily, yellow liquids, insoluble in water but soluble in 
fats and oils. Vitamin K exists in at least three forms, all belonging to 
the group of chemical compounds known as quinones. The naturally occurring 
fat-soluble vitamins are K.sub.1 (phylloquinone), K.sub.2 (menaquinone), 
and K.sub.3 (menadione). The amount of the fat-soluble vitamins employed 
herein to fortify the present food compositions can vary. If desired, the 
food compositions 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. 
Vitamins that are nonsoluble in fat can similarly be included in the 
present food compositions. Among these vitamins are the vitamin B complex 
vitamins, vitamin C, vitamin G, vitamin H, and vitamin P. The minerals 
include the wide variety of minerals known to be useful in the diet, such 
as calcium, magnesium, and zinc. Any combination of vitamins and minerals 
can be used in the present food compositions. 
Due to the relative low sweetness intensity of the reduced calorie sugars 
described in part B of this application, noncaloric or reduced calorie 
sweeteners are typically included in the food compositions of the present 
invention. Noncaloric or reduced calorie sweeteners include, but are not 
limited to, aspartame; saccharin; alitame, thaumatin; dihydrochalcones; 
cyclamates; steviosides; glycyrrhizins, synthetic alkoxy aromatics, such 
as Dulcin and P-4000; sucralose; suosan; miraculin; monellin; sorbitol, 
xylitol; talin; cyclohexylsulfamates; substituted imidazolines; synthetic 
sulfamic acids such as acesulfame, acesulfam-K and n-substituted sulfamic 
acids; oximes such as perilartine; rebaudioside-A; peptides such as 
aspartyl malonates and succanilic acids; dipeptides; amino acid based 
sweeteners such as gem-diaminoalkanes, meta-aminobenzoic acid, 
L-aminodicarboxylic acid alkanes, and amides of certain 
alpha-aminodicarboxylic acids and gem-diamines; and 
3-hydroxy-4-alkyloxyphenyl aliphatic carboxylates or heterocyclic aromatic 
carboxylates. 
Bulking or bodying agents can also be included in the food compositions of 
the present invention. The bulking agents can be nondigestible 
carbohydrates, for example, polydextrose and cellulose or cellulose 
derivatives, such as carboxymethylcellulose, carboxyethylcellulose, 
hydroxypropylcellulose, methylcellulose and microcrystalline cellulose. 
Other suitable bulking agents include starches, gums (hydrocolloids), 
fermented whey, tofu, and maltodextrins. 
The food compositions of the present invention can also include dietary 
fibers. By "dietary fiber" is meant 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. 
Examples of 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). Commercial fibers such as purified plant cellulose, or 
cellulose flour, can also be used. Naturally occurring fibers include 
fiber from whole citrus peel, citrus albedo, sugar beets, citrus pulp and 
vesicle solids, apples, apricots, and watermelon rinds. 
These dietary fibers may be in a crude or purified form. The dietary fiber 
used may be of a single type (e.g. cellulose), a composite dietary fiber 
(e.g. citrus albedo fiber containing cellulose and pectin), or some 
combination of fibers (e.g. cellulose and a gum). The fibers can be 
processed by methods known to the art. 
The food compositions of the present invention can also contain minor 
amounts of optional flavorings, emulsifiers, anti-spattering agents, 
anti-sticking agents, anti-oxidants, or the like. 
D. ANALYTICAL METHODS 
1. CNP/GC Method 
The carbon number profile (CNP) of the triglycerides present in the reduced 
calorie fat can be determined by programmed temperature-gas chromatography 
(GC) using a short fused-silica-column coated with methyl silicone for 
analysis and characterization of the composition by molecular weight. The 
triglycerides are separated according to their respective carbon numbers, 
wherein the carbon number defines the total number of carbon atoms on the 
combined fatty acid residues. The carbon atoms on the glycerol molecule 
are not counted. Glycerides with the same carbon number will elute as the 
same peak. For example, a triglyceride composed of three C.sub.16 
(palmitic) fatty acid residues will co-elute with triglycerides made up of 
one C.sub.14 (myristic), one C.sub.16 and one C.sub.18 (stearic) fatty 
acid residue or with a triglyceride composed of two C.sub.14 fatty acid 
residues and one C.sub.20 (arachidic) fatty acid residue. 
Preparation of the fat sample for analysis is as follows: 1.0 ml. of a 
tricaprin internal standard solution (2 microg./ml.) is pipetted into a 
vial. The methylene chloride solvent in the standard solution is 
evaporated using a steam bath under a nitrogen stream. Two drops of the 
fat sample (20 to 40 microg.) are pipetted into a vial. If the fat sample 
is solid, it is melted on a steam bath and stirred well to insure a 
representative sample. 1.0 ml. of bis (trimethylsilytrifluoroacetamide) 
(BSTFA) is pipetted into the vial which is then capped. The contents of 
the vial are shaken vigorously and then placed in a beating block 
(temperature of 100.degree. C.) for about 5 minutes. 
For determining the CNP/GC of the prepared fat samples, a Hewlett-Packard 
5880A series gas chromatograph equipped with temperature programming and a 
hydrogen flame ionization detector is used together with a Hewlett-Packard 
3351B data system. A 2 m. long, 0.22 mm. diameter fused silica capillary 
column coated with a thin layer of methyl silicone (Chrompak CP-SIL 5) is 
also used. The column is heated in an oven where temperature can be 
controlled and increased according to a specified pattern by the 
temperature programmer. The hydrogen flame ionization detector is attached 
to the outlet port of the column. The signal generated by the detector is 
amplified by an electrometer into a working input signal for the data 
system and recorder. The recorder prints out the gas chromatograph curve 
and the data system electronically integrates the area under the curve. 
The following instrument conditions are used with the gas chromatograph: 
______________________________________ 
Septum purge 1 ml./min. 
Inlet pressure 5 lbs./in.2 
Vent flow 75 ml./min. 
Makeup carrier 30 ml./min. 
Hydrogen 30 ml./min. 
Air 400 ml./min. 
______________________________________ 
1.0 microl. of the prepared fat sample is taken by a gas-tight syringe and 
injected into the sample port of the gas chromatograph. The components in 
the sample port are warmed up to a temperature of 365.degree. C. and swept 
by a helium carrier gas to push the components into the column. The column 
temperature is initially set at 175.degree. C. and held at this 
temperature for 0.5 min. The column is then heated up to a final 
temperature of 355.degree. C. at a rate of 25.degree. C./min. The column 
is maintained at the final temperature of 355.degree. C. for an additional 
2 min. 
The chromatographic peaks generated are then identified and the peak areas 
measured. Peak identification is accomplished by comparison to known pure 
glycerides previously programmed into the data system. The peak area as 
determined by the data system is used to calculate the percentage of 
glycerides having a particular Carbon Number (C.sub.N) according to the 
following equation: 
EQU % C.sub.N =(Area of C.sub.N /S).times.100 
wherein S=sum of Area of C.sub.N for all peaks generated. 
The Area of C.sub.N is based upon the actual response generated by the 
chromatograph multiplied by a response factor for glycerides of the 
particular Carbon Number. These response factors are determined by 
comparing the actual responses of a mixture of pure glycerides of various 
Carbon Numbers to the known amounts of each glyceride in the mixture. A 
glyceride generating an actual response greater than its actual amount has 
a response factor less than 1.0; likewise, a glyceride generating a 
response less than that of its actual amount has a response factor of 
greater than 1.0. The mixture of glycerides used (in a methylene chloride 
solution) is as follows: 
______________________________________ 
Component Carbon No. 
Amount (mg./ml.) 
______________________________________ 
Palmitic acid 16 0.5 
Monopalmitin 16 0.5 
Monostearin 18 0.5 
Dipalmitin 32 0.5 
Palmitostearin 34 0.5 
Distearin 36 0.5 
Tripalmitin 48 1.5 
Dipalmitostearin 
50 1.5 
Distearopalmitin 
52 1.5 
Tristearin 54 1.5 
______________________________________ 
2. Fatty Acid Composition 
Principle 
The fatty acid composition of the triglycerides present in the reduced 
calorie fat is measured by gas chromatography. First, fatty acid ethyl 
esters of the triglycerides are prepared by any standard method (e.g., by 
transesterification using sodium ethoxide), and then separated on a 
capillary column which is coated with DB-WAX stationary phase. The fatty 
acid ethyl esters are separated by chain length and degree of 
unsaturation. A split injection is made with flame ionization detection. 
Quantitation is performed by use of a double internal standard method. 
This method can separate fatty acid ethyl esters from C.sub.6 to C.sub.24. 
Equipment 
______________________________________ 
Gas Chromatograph 
Hewlett-Parkard 5890, or 
equivalent, equipped with a 
split injector and flame 
ionization detector, 
Hewlett-Packard Co., 
Scientific Instruments Div., 
1601-T California Ave., Palo 
Alto, CA 94304 
Autosampler Hewlett-Packard 7673A, or 
Injector equivalent 
column 
Column 15 m .times. 0.25 mm 
I.D., fused silica capillary 
column coated with DB-WAX 
(0.25 micron film thickness), 
Hewlett-Packard Co., 
Scientific Instruments Div. 
Data System Hewlett-Packard 3350, 3000-T 
Hanover St., Palo Alto, CA 
94304 
Recorder Kipp & Zonen, BD40, Kipp & 
Zonen 
Reagent 
Hexane Burdick & Jackson, or 
equivalent, American 
Scientific Products 
______________________________________ 
Reference Standards 
Two reference standards are used each day of operation to verify proper 
operation of this method. 1) A reference mixture of fatty acid methyl 
esters (FAME) is used to check the operation of the instrument. This 
reference mixture has the following fatty acid composition: 1% C.sub.14:0, 
4% C.sub.16:0, 3% C.sub.18:0, 45% C.sub.18:1, 15% C.sub.18:2, 3% 
C.sub.18:3, 3% C.sub.20:0, 3% C.sub.22:0, 20% C.sub.22:1, and 3% 
C.sub.24:0. 2) A reference standard of a commercial shortening is used to 
check the operation of the total system--ethylation and gas 
chromatographic analysis. The shortening reference standard has the 
following fatty acid composition: 0.5% C.sub.14:0, 21.4% C.sub.16:0, 9.2% 
C.sub.18:0, 40.3% C.sub.18:1, 23.0% C.sub.18:2, 2.2% C.sub.18:3, 0.4% 
C.sub.10:0, 1.3% C.sub.20:1, and 0.3% C.sub.22:0. 
The reference mixture of FAME should be diluted with hexane and then 
injected into the instrument. A new vial of FAME reference mixture should 
be opened every day since the highly unsaturated components, C.sub.18:2 
and C.sub.18:3, oxidize easily. The shortening reference standard should 
be ethylated with the samples prior to their analysis by capillary gas 
chromatography. The results from the reference standards should be 
compared with the known values and a judgment made concerning the 
completed analysis. If the results of the reference standards are equal to 
or within.+-.standard deviations of the known values, then the equipment, 
reagents and operations are performing satisfactorily. 
Operation 
A. Instrumental Set-up 
1. Install the column in the gas chromatograph, and set up the instrumental 
conditions as in Table 4. 
2. Set up the data system with the appropriate method to acquire and 
analyze the data. The retention times may have to be adjusted in the 
method due to instrument variations. Consult the data system reference 
manual on how to do this--HP3350 User's Reference Manual. Unity response 
factors are used for each component. 
3. Obtain the shortening reference standard for analysis with the samples 
and ethylate it with the samples. 
TABLE 4 
______________________________________ 
INSTRUMENTAL CONDITIONS 
______________________________________ 
Instrument Hewlett-Packard 5890 
Column 15 m .times. 0.25 mm I.D., coated 
with DB-WAX, 0.25.mu. film 
thickness 
Column head pressure 
12.5 psi 
Carrier gas Helium 
Injector "A" temperature 
210.degree. C. 
Split vent flow 100 mL/min 
Septum purge 1.5 mL/min 
Oven temperature profile: 
Initial temperature 
110.degree. C. 
Initial time 1 min 
Rate 1 15.degree. C./min 
Final temp 1 170.degree. C. 
Final time 1 0 min 
Rate 2 6.degree. C./min 
Final temp 2 200.degree. C. 
Final time 2 0 min 
Rate 3 10.degree. C./min 
Final temp 3 220.degree. C. 
Final time 3 8 min 
Detector FID 
Detector temp 230.degree. C. 
Make-up gas 30 mL/min 
Detector H.sub.2 flow 
30 mL/min 
Detector air flow 300 mL/min 
______________________________________ 
B. Analysis of Samples - (The samples are analyzed with a double internal 
standard.) 
1. Dilute the reference mixture of FAME with hexane. The methyl esters 
should be approximately 2% in hexane. Inject one microliter of this 
solution via the autosampler. The results must meet the criteria in the 
Reference Standards section. 
2. Prepare the triglyceride samples to be analyzed by adding two different 
internal standards, C.sub.9 and C.sub.21 triglycerides. (C.sub.9 and 
C.sub.21 triglycerides are commercial standards consisting of 100% 
9-carbon and 21-carbon triglycerides, respectively.) The internal 
standards are added to the samples at about 10% by weight of the sample. 
The samples (including the internal standards) are then converted to ethyl 
esters by any standard method. 
3. Set up a sequence in the LAS data system to inject the samples. 
4. Activate the autosampler to inject 1.0 microl. of the samples in the 
sequence. The gas chromatograph will automatically begin its temperature 
program and the data system will collect and analyze the data for the 
sequence. 
5. The data is analyzed with the two internal standard procedure. The 
absolute amount (mg of esters per gram of sample) of the C.sub.6 through 
C.sub.16 components is calculated from the C.sub.9 internal standard. The 
absolute amount of the C.sub.18, C.sub.20, C.sub.22 and C.sub.24 
components is calculated from the C.sub.21 internal standard. Weight 
percentages of fatty acids are calculated from these amounts. 
E. Specific Illustrations of Fat-Containing and Sugar-Containing Food 
Compositions of the Present Invention 
The following are specific illustrations of fat-containing and 
sugar-containing food compositions according to the present invention:

EXAMPLE 1 
A chocolate-flavored molding composition is formulated from the following 
ingredients: 
______________________________________ 
Ingredient Amount (g.) 
______________________________________ 
Reduced calorie fat 
1130.7 
Chocolate liquor 152.0 
Lecithin 4.0 
Cocoa powder (10-12% fat) 
208.0 
Whole milk solids (26% fat) 
388.0 
Nonfat milk solids 140.0 
Vanillin 2.0 
Reduced calorie 1948.0 
sugar* 
Aspartame q.s. 
______________________________________ 
*5-C-hydroxy methylL-arabino-hexopyranosyl-D-sorbitol 
The reduced calorie fat used in this chocolate-flavored composition is 
prepared generally as follows: Compritol 888 (a mixture of approximately 
25% monobehenin, 50% dibehenin and 25% tribehenin, sold by Gattefosse of 
200 Sawmill River Road, Hawthorne, N.Y.) is further esterified at 
265.degree. C. with capric fatty acid until the diglyceride concentration 
of the mixture is reduced to less than 4%. The weight ratio of Compritol 
888 to capric fatty acid at the start of esterification is approximately 
70:30. The resulting esterified mixture is deodorized at 260.degree. C. 
for 3 hours and then combined with Captex 355 (a mixture of C.sub.8 
/C.sub.10 medium chain triglycerides, sold by Capital City Products, of 
Columbus, Ohio) in a weight ratio of 58:42. This mixture is randomly 
rearranged (randomized) at a temperature of 80.degree. C. for 20 minutes 
using 0.06% sodium methoxide as the catalyst, neutralized with phosphoric 
acid and then filtered to remove sodium phosphate. The randomized mixture 
(approximately 2.5% diglycerides, 38.5% medium chain (MMM) triglycerides, 
43.5% mono-long chain (MLM/MML) triglycerides, 13.5% di-long chain 
(LLM/LML) triglycerides, and 1% tri-long chain (LLL) triglycerides), is 
steam stripped at a temperature of 450.degree. to 515.degree. F. 
(232.2.degree. to 268.3.degree. C.) during which a major portion of the 
medium chain triglycerides are distilled off. The stripped residue (2.5% 
diglycerides, 6% medium chain triglycerides, 67% mono-long chain 
triglycerides, and 24% di-long chain triglycerides) is then passed three 
times at gradually increasing temperatures through two 14 inch molecular 
stills (connected in series) to increase the level of mono-long chain 
triglycerides. The molecular stills are operated under the following 
conditions: 
Bell jar pressure: 5-11 microns Hg. abs. 
Rotor feed temperature: 125.degree.-160.degree. C. 
Rotor residue temperature: 180.degree.-216.degree. C. 
Initial feed pump rate: 36-40 lbs./hour 
Distillation rate: 4-6 lbs./hour per unit 
The distillate fractions obtained (total of 25) contain 1% medium chain 
triglycerides, 92% mono-long chain triglycerides, and 5-6% di-long chain 
triglycerides. Each of these distillate fractions are subjected to 
nonsolvent fractionation, first at 80.degree. F. (26.7.degree. C.) and 
then at 76.degree. F. (24.4.degree. C.). The liquid (olein) fractions 
obtained are combined to provide a reduced calorie fat having the 
following carbon number profile (CNP): 
______________________________________ 
CNP % 
______________________________________ 
32 0.1 
34 0.5 
36 1.7-2.0 
38 21.7-22.9 
40 48.0-48.6 
42 23.9-24.7 
44 0.7-1.0 
46 0.2 
48 0.2 
50 0.2 
52 0.1 
______________________________________ 
The chocolate-flavored molding composition is processed in two batches of 
equal size. The cocoa powder, whole milk solids, nonfat milk solids, 
vanillin, reduced calorie sugar and aspartame are blended, and then the 
melted chocolate liquor is added along with 720.8 g. of the reduced 
calorie fat. After blending, this mixture is refined twice using a Lehman 
Four-Roll Refiner (200 psi NIP pressure). This refined mix (3381.4 g.) is 
dry conched 21/2 to 3 hours at 145.degree. F. (62.8.degree. C.) using a 
Hobart C-100 Mixer set at speed #2. An additional 257.4 g. of reduced 
calorie fat is added, and the temperature of the mix is then reduced to 
125.degree. F. (51.7.degree. C.). The mix is then wet-conched at speed #1 
for 17 hours. 
Finally, the remaining reduced calorie fat (152.5 g.) and lecithin is added 
to this chocolate-flavored mixture and blended thoroughly for about 45 
minutes. The temperature is then reduced to 85.degree. to 90.degree. F. 
(29.4.degree. to 32.2.degree. C.) and, after equilibration, the 
chocolate-flavored mass is weighed into bar molds in 42.6 g. portions. The 
molds are placed in a 50.degree. F. (10.degree. C.) environment with 
circulating air. The bars are then tempered under the following 
conditions: 
______________________________________ 
Temperature 
(.degree.F.) (.degree.C.) 
Time (hours) 
______________________________________ 
50 10 72 
60 15.6 24 
70 21.1 8 
60* 15.6* 16 
______________________________________ 
*for demolding purposes 
The tempered bars were then demolded, individually wrapped in foil and 
stored at 70.degree. F. (21.1.degree. C.). 
EXAMPLE 2 
A chocolate-flavored molding composition is formulated from the following 
ingredients: 
______________________________________ 
Ingredient Amount (g.) 
______________________________________ 
Reduced calorie fat* 
320.8 
Chocolate liquor 55.1 
Lecithin 0.6 
Cocoa powder (10-12% fat) 
61.2 
Whole milk solids (26% fat) 
172.8 
Vanillin 0.6 
Reduced calorie 579.6 
sugar* 
Aspartame q.s. 
______________________________________ 
*Same as Example 1 
The cocoa powder, whole milk solids, vanillin, reduced calorie sugar and 
aspartame is blended, and then 216.1 g. of melted reduced calorie fat is 
added. This mixture is passed through the Lehman Four-Roll refiner (200 
psi NIP pressure) twice. The melted chocolate liquor is added to the 
refined mix (988.1 g.) and then dry conched at 140.degree. F. (60.degree. 
C.) for 3 hours using a C-100 Hobart mixer set at speed #2. The 
temperature of the mix is then reduced to 120.degree. to 125.degree. F. 
(48.9.degree. to 51.7.degree. C.). Lecithin and more reduced calorie fat 
(50.0 g.) are added, and then the mix is wet-conched for 16 hours at speed 
#1. 
An additional 54.7 g. of reduced calorie fat is then added to the 
wet-conched mixture. The temperature is then reduced to about 90.degree. 
F. (32.2.degree. C.), and the chocolate-flavored mass is molded into 1 oz. 
bars. The bars are tempered at 50.degree. F. (10.degree. C.) for 16-18 
hours, at 60.degree. F. (15.6.degree. C.) for 24 hours, and then at 
70.degree. F. (21.1.degree. C.) for 24 hours before demolding. 
EXAMPLE 3 
A chocolate-flavored enrobing composition is formulated from the following 
ingredients: 
______________________________________ 
Ingredient Amount (g.) 
______________________________________ 
Reduced calorie fat* 
570.4 
Chocolate liquor 76.0 
Lecithin 2.0 
Cocoa powder (10-12% fat) 
104.0 
Whole milk solids (26% fat) 
194.0 
Nonfat milk solids 70.0 
Reduced calorie 974.0 
sugar* 
Aspartame q.s. 
______________________________________ 
*Same as Example 1. 
The cocoa powder, whole milk solids, nonfat milk solids, reduced calorie 
sugar and aspartame are thoroughly blended, and then the melted chocolate 
liquor is added along with 360.4 g. of the reduced calorie fat. After 
thorough blending, the resultant mixture is passed through a Lehman 
Four-Roll Refiner twice (NIP pressure 200 psi). The refined mix (1732.6 
g.) is recovered and then dry-conched 21/2 to 3 hours at 145.degree. F. 
(62.8.degree. C.) using a Hobart C-100 mixer set at speed #2. After an 
additional 135.0 g. of the reduced calorie fat is added, the mix 
temperature is reduced to 125.degree. F. (51.7.degree. C.), and then 
wet-conched for about 18 hours at speed #1. 
The remaining reduced calorie fat (75.0 g.) and the lecithin are then added 
to the wet-conched mixture and mixed thoroughly. A portion of this 
chocolate-flavored coating mixture (.about.1000 g.) is heated to 
120.degree. to 125.degree. F. (48.9.degree. to 51.7.degree. C.) and mixed 
at this temperature for about 60 minutes. The temperature is then reduced 
to about 85.degree. F. (29.4.degree. C.). Rectangular pieces of 
confectionary candy centers (caramel, peanuts and nougat) weighing about 8 
or 12 g. each are dipped into this chocolate-flavored coating mixture to 
enrobe the centers. After draining the excess coating, the pieces are 
placed on trays and cooled to 50.degree. F. (10.degree. C.). After about 
65 hours at 50.degree. F. (10.degree. C.), the enrobed candy products are 
gradually warmed to 60.degree. F. (15.6.degree. C.) and then held at this 
temperature for 17 days, followed by gradual warming to 70.degree. F. 
(21.1.degree. C.) and then holding at this temperature for 4 hours. The 
enrobed 8 g. centers are cut into two pieces, while the 12 g. centers are 
cut into three pieces, and then wrapped individually in foil for storage 
at 70.degree. F. (21.1.degree. C.). 
EXAMPLE 4 
A chocolate-flavored molding composition is formulated from the following 
ingredients: 
______________________________________ 
Ingredient Amount (g.) 
______________________________________ 
Reduced calorie fat* 
267.5 
Chocolate liquor 22.04 
Lecithin 1.2 
Cocoa powder (10-12% fat) 
30.16 
Whole milk solids (26% fat) 
56.27 
Nonfat milk solids 20.30 
Vanillin 0.3 
Reduced calorie sugar 
280.7 
Aspartame 1.7 
______________________________________ 
*Same as Example 1. 
The cocoa powder, whole milk solids, nonfat milk solids, vanillin, reduced 
calorie sugar and aspartame are thoroughly blended, and then the melted 
chocolate liquor is added along with 104.5 g. of the reduced calorie fat. 
After thorough blending, the resultant mixture is passed through a Lehman 
Four-Roll Refiner twice (NIP pressure 200 psi). The refined mix (508.7 g.) 
is recovered and then dry-conched 3 hours at 120.degree. to 125.degree. F. 
(48.9.degree. to 51.7.degree. C.) using a Hobart C-100 mixer set at speed 
#2. After an additional 31.4 g. of the reduced calorie fat is added, the 
mix is then wet-conched for 16 hours at speed #1. 
The remaining reduced calorie fat (31.6 g.) and the lecithin are then added 
to the wet-conched mixture. The temperature is then reduced to about 
85.degree. F. (29.4.degree. C.), and the chocolate-flavored mass is molded 
into 1 oz. bars. The bars are tempered at 50.degree. F. (10.degree. C.) 
for 16-18 hours, at 60.degree. F. (15.6.degree. C.) for 24 hours, and then 
at 70.degree. F. (21.1.degree. C.) for 24 hours before demolding. 
EXAMPLE 5 
Preparation of brownies containing 
5-C-hydroxymethyl-.alpha.-L-arabino-hexopyranosyl-D-glucitol 
______________________________________ 
Ingredient Amount (gms) 
______________________________________ 
5-C-hydroxymethyl-.alpha.-L-arabino- 
309.8 
hexopyranosyl-D-glucitol 
Flour 152 
Reduced calorie fat* 
50 
Cocoa 35.3 
Starch 11.7 
Conventional additives 
6.2 
(flavors and a small 
amount of baking soda) 
Eggs 50 
Canola oil (I.V. 90) 
63 
Water 80 
______________________________________ 
*Same as Example 1 
The ingredients are stirred with a large spoon until well blended (about 50 
strokes or 1 minute) to form a batter. The batter is poured into a lightly 
greased 13".times.9".times.2" (33 cm..times.23 cm..times.5 cm.) pan, and 
then baked at 350.degree. F. (176.7.degree. C.) for about 26.5 minutes to 
produce the finished brownies. 
EXAMPLE 6 
Preparation of cookies containing 
5-C-hydroxymethyl-.alpha.-L-arabinohexopyranosyl-D-glucitol 
______________________________________ 
Ingredient Amount (gms) 
______________________________________ 
5-C-hydroxymethyl-.alpha.-L- 
176 
arabinohexopyranosyl-D-glucitol 
Table sugar (i.e., sucrose) 
176 
Flour 328 
Reduced calorie fat* 
196 
Egg 96 
Water 20 
Conventional additives 
8 
(flavors and a small 
amount of baking soda) 
______________________________________ 
*Same as Example 1 
The ingredients are combined and the resulting dough is kneaded until 
uniform. Dough balls (10-13 gm) are individually placed on a lightly 
greased cookie tray and then baked at 350.degree. F. (176.7.degree. C.) 
for 7-8 minutes to produce finished cookies. 
EXAMPLE 7 
Preparation of a white cake containing 
5-C-hydroxymethyl-.alpha.-L-arabinohexapyranosyl-D-sorbitol 
______________________________________ 
Ingredient Amount (gms) 
______________________________________ 
5-C-hydroxymethyl-.alpha.-L-arabino- 
133 
hexapyranosyl-D-sorbitol 
Cake flour 107 
Reduced calorie fat* 
47.5 
Double-acting baking powder 
6.7 
Milk 130 
Egg whites 60 
Vanilla 2.5 
______________________________________ 
*Same as Example 1 
The ingredients are stirred with an electric mixer to form a uniform 
batter. The batter is poured into a lightly greased 13".times.9".times.2" 
(33 cm..times.23 cm..times.5 cm.) pan, and then baked at 350.degree. F. 
(176.7.degree. C.) for 40 minutes to produce the finished white cake. This 
cake looks like a conventional white cake, but has reduced caloric value. 
EXAMPLE 8 
Preparation of margarine containing 
5-C-hydroxymethyl-.alpha.-L-arabino-hexapyranosyl-D-sorbitol 
______________________________________ 
Amount (g) 
______________________________________ 
Oil Phase Ingredients 
Canola oil (I.V. 90) 
1370 
Reduced calorie fat* 
600 
Canola hardstock (I.V. 4) 
30 
Color q.s. 
Flavor q.s. 
Aqueous Phase Ingredients 
Water 162.5 
Soluble whey protein 
25 
Reduced calorie sugar* 
50 
Aspartame q.s. 
Salt 37.5 
______________________________________ 
*Same as Example 1 
The oil phase ingredients are melted and mixed together. The aqueous phase 
ingredients are mixed together and dissolved. The oil and aqueous phases 
are combined, mixed together and passed through a scraped wall heat 
exchanger to form an emulsified spread using standard margarine-making 
conditions.