CA2042057A1 - Reduced calorie triglycerides in foods - Google Patents

Abstract

ABSTRACT

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

Description

20~20~7 l :

QDUCED CALORIE TRl6L~t~RlnEs IN FOQDS
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ll Inv~ntorS John ~estcott Finl~ resid1ng ~t 3 Oldstons L~n~, ~h1pp~n~, 07981, L~r-nc- P~ul Kl~m~nn r~s1d1ng ~t 196 T~nglc~ood Dr1v-, Somorv111~, 08876, C11b~rt Anton10 L~v~ residlng ~t 23 C~-~r1dgo Avonuc, Dcnv111-, 0783~, M1ch~ol Storv~ Ottsrburn rss1d1ng t ll~S Sussox Turnp1~s, R~ndolph, 07896, d~rd Loron ~hoolor rss1d1ng ~t 7 Rod~ood Dr1vo, Fs1r~101d, 07006, ~11 o~ Nc~ J~rss~, Potor S1-rond~ 61von, Jr rcs1d1ng t 508 H~cl Stroot, tlsncos, 5111no1s, 60022, ~nd Ron~ld ~h111p D A~ol1~ ro~d~ng ~t 1 Fox Pl~c~, ~1c~v111s, Ro~ ~or~ 11801 ' i ;'~ ;, .~:;'," ' ~.
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BAClt6ROUND OF IHVENTION

Thls 1nvention pertains to the use of a new type of natural tr1glyceride in food composltions to yield a product lower in calor1es These triglycer1des strategically position saturated long chain fatty ~ctds and a short chain acid to achteve the des1red balance of calor1c ava11ab111ty and funct10nal properties It has been reported that f-ts make up 40% to 45% of the ca10r1es tn th- average Amer1c-n d1et w1th trtglycerides const1tut1ng about 90X of the total ed1ble fats consumed fats provtde a~proximately nine calories per gram co~pared to approx1~ately four calories p-r gr-m for proteins and carboh)drates ~hus ma~or r-se-rch efforts have been conducted toward the reduct10n of c-loric 1nt-ke for health or ~ed1cal reasons w1thout s-cr1ftc1ng the funct10nal and organolept1c propert1es of fat One str-t-gy for develop1ng reduc~d c-lorie r~plac~ment fats has b~n to structurally re-engtneer natural tr1glycer1des in such a way s to reta1n the1r conv-nt10nal funct10nal propert1es 1n food compos1~10ns whtle remo~ling their suscept1b111ty towards hydrclys1s or subsequent absorption l dur1ng 11pid d1gestion ~or example the fatty acids I att-ched to glycerol have been replaced w1th alternativD
ac1ds (U S Patent Nos 3 579 548 ~Ihyte and 4 582 715 , Volcenhe1n); groups have been insertet between the fatty actds and the glycerol backbone ( propoxylated glycerolsn 20~20~7 EuroPean Patent Application No 254 547 ~hite and Pollard);
the ester linkages have been replaced by ether linkages (U S
Patent No 3 818 089 Bayley and Carlson and Canadian Patent Ho 1 106 681 ~rost); the ester llnkages have been reversed (U S Patent No 4 508 746 Hamm); and the glycerol moiety h~d been replaced with an altern-te alcohol (U S P-tent Nos 2 92~ 528 B-rske~ et al nd 2 993 063 Alsop nd Carr) A seond strategy for dev-loping r~duced c-lorie repl-cement f ts has been to synthes1ze nonabsorbable polymer1c materials structurally unl1ke triglycer1des but hav1ng phys1c~1 prop~rt1es s1m11ar to ed1ble fats Min-ral oil was dlsclosed as e~rly as 1994 (U S P-tent No 519 980 ~1nter) and more recently polydextrose (U S P-tent No 4 631 196 Zeller);
polyglucos~ ~nd po~ ltos~ (U.S Ptt~nt No 3 876 ~94 Rennhsrd); polysl1Oxane (ur P-t-nt Appl No 205 273 Frye); ~oJob~ wax (S~ ter Pat No 3 529 56~ An1ka); and polyethylcne polymers ( 6er P~t-nt No 207 070 Mieth et al ) have been suggested :~ ~
A th1rd str-t-gy for developing reduced calorie replacement f ts comb1nes the flrst two Rather than restructure tr1gl~cer1de molecules or find a subst1tute which is structur~lly disstmilar this pproach uses var1Ous polyol esters compounds which have numbers of fatty acid groups in excess of the three in conventional triglyceride fats as nonabsorblble fat replacements For example fully ester1fied sugar alcohols (LapworSh and Pearson and '~
,"~,,, :,. -,, .

...''~,',:',',.'''''','.'.' '''''''"' '''' ' '' '''';' ~ 4 2~2~7 Halltburton, et al , 13 J Biol Chem 296 and 301 (19l9));
ester1fted penta~rYthritol~ a tetrahydric neopentyl sugar alcohol which c-n be formed from pent-erythrose (U S Patent No 2,962 419, M1ntch); and amylose esters (U S D A Southern and ~estern Regtonal Rese-rch Laboratortes, Booth and Gros, J Amer 011 Chem Soc 551 (1963)) h-ve been suggested Sucrose polyest-rs, nondtgest1ble m1xtur-s of sucrose hexa-, hepta-, and octa- f-tty actd esters h-ve been suggested as low calor1e replac~m-nts of ed1ble fats and o11s 1n food compos1t1Ons (U S P-t-nt Nos 3,600,186, ~-ttson and Volpenhe1n, 4,~46,l65, Roberts, nd 4,461,782, Roberts ~nd Rodr1guez) Th- calor1c ava11ab111ty and d1gest1btl1ty of a ser1es of d1mer1c and polymer1c glycer1des 1nclud1ng d1glycer1de esters of succtn1c, fumar1c, and ad1ptc acids, ~nd polymer1c fats from stear1c, ol-1c, nd short chained d1bas1c ac1ds ~-r- ssessed by the U S D A group supr-, and polygl~cerol esters have s1nce been sugg-st-d (U S Patent Nos~ 3,637,774, B~bayan and Lehman and 3,968,169, Se1den and Mart1n) Nond1gest1ble or nonabsorb~ble tr1glycer1de analogs, polyol esters, ~nd poly-er1c mater1als have proven d1sappotnt1ng as fat repl~cemonts bec~use, when tested tn feed1ng tr1-1s, they c~used g~strolnt-st1nal slde effects, 1n some c~ses so extreme that frank anal leakage was observed (Hamm, 49 ~
Food Sci 419 (1984), Haumann, 63 J Amer 011 Chem Sot 27g (1986), and L-C-rge, 42 Food Tech 84 (1988)) To alleviate th1s problem, var10us hardened fats, notably hydrogenate:
palm o11s and synthettc cocoa butters, have been employe~ a;

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2~2Q~7 antd-~r;l le~ge a9ent5 to be used with sucrose pDlyesters (U S Patent Nos 4 005 195 Oandecek 4 005 196 Jandecek and H-ttson and 4 461 ~82 Robbins and Rodriguez) and saturated residues h-ve been incorporated into the polyester molecules (Eur Patent Appl Nos 236 2B8 Bernhardt and 256 585 van der Plank and Ro~enda~l) The f~tty acid mo1eties of po~glycerol esters c-n be cat~bolized if the ~llphatic group of the fatty ~c1d is short but the polygl~cerol 1ts-1f 1s not met-bolized (M1chael nd Coots 20 Tox1col Appl Pharm 334 (1971)) nd 1ts lax~t1ve effect is so Dronounced th-t the compounds h-ve been suggested for use ~s f~c-l softeners (U S P-tent ~o 3 495 010 Fossel) Sucrose pol~esters ~lso interfere with cholesterol metabolism ~nd v1t~min A ~nd v1tam1n E absorpt1On (Aust et al 25 Ann Nutr Het~b 255 (1981); 61ueck et ~1 32 Amèr J Clin Nutr 1636 (I9~9); ~nd Slett-n et al 7 Acta V1tam1n~1 ;
En2y~01 49 ~I9~S)) Pol~esters st1mul-te the excret1On of stero1ds 1n the f-ces (Glueck at al 33 Amer J Clin Nutr 2177 (1980)) and 1nterfere ~1th the met~bolism of 11poph111c tox1ns (R1chter et al 40 Chem B1O1 Inter~ct 335 ~I982)) In add1t1On some res1dual accumul~tion of nond1gest1ble pol~esters occurs 1n tissues especially in fat t1ssue though ~lso tn muscles nd other org~ns The ~ccumulat1On increases with long term digestion and tne incorporated esters are not excreted even after the compounos are eliminated from the diet (Aust et al 26 Nahrung K3 (1982) and 30 Nahrung 453 (19B6)). :, ',',',",''" ,' ",::':'.' ', 20~205~

Some scientists have reported that high melting point fats are less digest1ble than those with low melting points ani~at and vegetable fats with melting points lower than 50 C
are well absorbed and dlgested by normal men (Deuel The Lit~g~ 214 (1955)); ~nd lower mclting point fats are more d1gest1ble in togs (Suzuki 29 C A 3378 (1935)) When tr1glycer1des are not melted dur1ng ltptd d19est10n they are normally excreted as sol1ds ~atty ac1ds w1th high melting po1nts also are less d1gestible th-n those w1th low melting po1nts (Mattson 69 J Nutr 33B; and H-sh1m et al 31 Am ~ C11n Nutr S273 (1978)) Two w~ys of increasing the melt1ng po1nt of fatty ac1ds ~re to 1ncrease the chain length and to decroase the degree of uns~turation (Hashim et al 31 Am J C11n Nutr S273 (1978)) Stud1es have also shown that branched cha1n fatty c1ds tend to have lower melting po1nts and are less absorbable than straight cha1n fatty Jc1ds wlth the sa~- nu~ber of carbon atoms Stud1es have also sho~n that stra1ght cha1n saturated fatty ac1ds fro~ C~ to C8 ~re completely d1gest1ble from C10 to Cl6 are progress1vely less absorbable and from C18 and hlgher only s11ghtly absorbsd (Carroll 64 ~ Nutr 399 (19S8)) Other stud1es have further demonstrated that tr1glycer1des hav1ng saturated f~tty ac1ds of eighteen carbons or longe- are less d1gest1ble th~n shorter chain fatty ac1ds and free fatty ac1ds are absorbed less readily as they get longer only 15~ fully hydrogenated linseed oil was absorbed compared with 98% for safflo~er o11 (Mattson 69 ~
j¦Nutr 33 (19S9)) higher saturated fatty ac1ds are poorlv 2~2~7 absorbed even when fed as a mixture with unsaturated fats (Rlce 61 J Nutr 253 (1956)); and rats fed hydrogenated soybe~n spray oll absorbed 30% wh11e over 90% of the uns~tur~ted o11 ~s ~bsorbed (Com~i 108 J Nutr 826 (l977)) Studies h~ve furth-r shown th-t the ~bsorb~b111ty of fat is l 1nfluenced by the pos1t10n~1 d1str1but10n of cert-1n fatty ¦ ~clds on the triglyceride stesr1c ~c1d is well absorbed by r~ts when ester1f1ed on th- 2- pos1t10n, but 1s poorly absorbed when on the l- or 3- pos1tlons when ole1c is ester1f1ed ~t the oth-r posit10ns (M~ttson, et al , 109 J
Nutr 1682 (1979)); ~nd st--ric and p~lmitic c1ds ~re better ~bsorb-d ~hen sltu~t~d ~t the 2- pos1tion of a tr191yceride thsn ~t the l- or 3- pos1t10ns of n~tur~lly occurring f~ts co~monly fed to 1nf-nts (~omer~111, t ~1 , 95 J Nutr 583 ,;
(196O ) l '` ", ';' Sever~l stud1es h~ve ~lso demonstr~ted th~t an 1ncre~se in d1st~ry c~lc1um or msgnes1um exerts ~n dverse effect on the ~bsorpt10n of f~tty ~c1ds w1th h1~h m-lt1ng points (Cheng, et sl 3~ J Nutr 237 (l949) ~nd ~d~yyon ~nd Lutw~k, 97 J ~;
Nutr 2~6 ~1969)) ~t seems prob~ble th-t, upon hydrolys1s, theso fstty ~c1ds form so-ps ~nd 1nsoluble complexes which ~re not re~d11~ ~bsorbed (C~rroll ~nd R1ch~rds, 64 J Nutr (1958)) ;~

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2042~5~

SU~AR~ OF INVENTI0~

An obJect of the present invention is to provide a new class of reduced calorle all natural triglycerides and food compos1tlons contain1ng these products Another object of thls 1nvent10n ts to provide a f~t composition that is subst~nt1ally reduc-d 1n calor1es wh-n compared to convent10nal fat compos1tions A further ob~ect of this lnvent10n 1s to prov1de a f-t wh1ch 1s at least partially nond1gest1ble thus y1eld1ng substant1ally fewer c~lor1es th~n convent10nal fat A furth-r ob~ect of th1s invent10n is to provide a reduced calor1e fat hav1ng excellent organolept1c propcrt1es so th-t 1t c-n be used ln a w1de var1~ty of foods A further ob~ect of th1s 1nvention is to prov1de a reduced calor1e fat hav1ng excellent funct10nal propert1e~ 1 e me1t1ng cryst-ll1z-t1on and flavor tr~nsfer so that 1t can be used 1n a ~1de var1ety of foods Th~o ~nd other ob~octs are ~ccompl1shed accord1ng to the presont 1nv~nt10n ~h1ch prov1des a n~w c1-ss of reduced c~lor1e tr1glyeer1des der1ved from glycerol esterif1ed with s~tur~ted long ch~n fatty ac1ds at the l- and 3- pos1t10ns ~nd ~ short chain ~c1d at the 2- pos~t10n The short chain ~c1d m~y ~e etther s~turated or uns~tur~ted e1ther straight or br~nched The term n~tural as us-d here1n means having the gener~l characteristic structure of n~tur-lly occurring tr1glycer1des e g formed by the ac1d ester1fication of glycerol The term long cha1n as used herein means that the fatty acid conta~ns at least about sixteen carbons The term short chain ~s used heretn means that the ac c cont-ins no more than aDout ten carbons Thus the new class of triglycerides are represented by the following f~rmula 2~2~7 tH~OR
CHOR
CH20R~

where R and R~ are long chain saturated fatty acid res~tues containing between 16 and 40 carbons; and R 1s a shott chain acid residue containing between 2 and IO carbons DETAlLD DESCRIPTlON OF TH~ INVENTIO~
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Reduced calor~e fats can contain fatty matcrials in addition to the triglyeerSdes of this invention which h~ve a short ch~1n ae1d at the 2 pos1tton and saturated long chain fatt~ ac1ds at the I and 3- pos1t10ns The triglycer1des may be a pure coopos1t10n cons1st1ng of only on- triglyceride or a m1xture of tr191~c-r1des ~here other fats are employed w1th these novel trtglycer1des they should b- of a type and 1n a~ounts co~pat1ble w1th the ob~ects of th1s invention pr1~artly to reduce calor1es Desirably reduced calorie fats and ed1ble foods of this invent10n w111 have predominant amounts of the novcl triglycer1des nd most usually would conta1n at least 35% and s much as 80% or h19her of these tr1glyt 1des by ~e1gbt The short chain ac1d should contain no more than abou tarbons preferably between 2 and 6 carbons and more preferably between 2 and 4 carbons Th1s short chain may ~?

2042~
either saturated or unsaturated stra~ght or branched Among the su1table short chain acids are acetic, propionic, n-butyr1c, iso-butyric caproic, capry~1c, pelargonic, c~pric, glycolic, lactic, hytracrylic hydroxybutyric, propeno1c, butenoic pentenoic, hexenoic, hepteno1c, octeno1c, noneno1c, deceno~c, and the llke This short cha1n ac1d will b- s~lected pr1mar~1y for the c~lories 1t dal1vers and its effect on mclt1ng char-cterist1cs In some c1rcumstances, its eff-cts on other prop~rt1es will also be of 1mportance The long cha1n fatty c1ds should b- full~ saturated w1th carbon chatns cont-1ning between about 16 and about 40 carbons, preferably bet~e~n 16 and 24 carbons, and more prefer~bly bet~een 16 and 20 carbons The long chain fatty ac1d at the I pos1t10n ~a~ b- 1th-r th- same or d1fferent th~n th~t at the 3 pos1tlon Among the long chain fatty ac1ds ~h1ch c~n be emplo~ed are p-lm1t1c, st~r1e, ~rachid1c, b-h-n1c, 11gnocer1c, cerot1c, montan1c, ~nd mel1ss1c, as well as other less frequently occurr1ng fatty c1ds B~ us1ng d1fferent comb1nat10ns of c1ds, the tr1glycertdes can be structured so as to obtaln the des1red functton~l character1st1cs, such s melting po1nt, for a v~riety of d1fferent food co~positions For example, esterify1ng wlt~
palm1t1c acid at the I- and 3- positions would likely give a tr1glycer1de ~1th a lower melting point than if esterifyin~
w1th behen1c ac1d, and would thus be more su1table ^~
incorporation into a butterscotch flavored chip ;1 ester1fy1ng with propionic acid at the 2- position of 3 ¦ 1Da1m1t~n, potential1f mono~orDhic trig1ycer1de is for~
l ' ~

.. : , 11 2~2~7 which has a higher degree of thermostability a sharp melting -point and crystalline unity ~his triglyceride would thus be appro~riate in a food composition in which fat bloom is problematic such as chocolate or the like coating "'.. ~,.
Mlxtures of fatty acids derived by the hydrolysis of natural fats cln also be employed such as those obtained from soybe-n sunflower peanut s-fflow-r olivc sesame rice br~n canol~ b-b~ssu coconut p-lm kernel palm rapeseed cottonse-d corn m~r1ne o11 or butter o11 or plant waxes such ~s Jo~oba Spec1f1c fracttons of these processed or unproctssed oils or waxes c-n ~lso be employ-d to provide f~tty ~cid residues wlth ~11phat1c groups which impart spec1f1c desired propert1es 1n the fat For example low molecul~r weight f~tty ac1ds derived from butter oil are des1r~ble for the d~1rg flavor and aroma they 1mpart upon p~rt1~1 hydrol~sis Also hydrogenated fatty ac1ds can be fr~ct10n~ted to prov1de fatty ac1ds for tr1glycer1des whlch melt w1th1n ~ des1r~ble temperature range e g just below body temper~ture These ch~r~cter1st1cs can also be obta1ned by co~b~n~t10ns o- the tr1glycer1des of th1s 1nvent10n w1th those n~turally present or used 1n food compos1t10ns `'",,'.'' The new class of triglycerides are represented by the following formul~

CH20R " ~ ~ ''; ' CHOR
CH20R'' 2~20~7 ; where, R and R~ are long chain, saturated fat~ty acid residues containing between l~ and 40 carbons, preferably between 16 and 24 car~ons, and more preferably between 16 and 20 carbons; and R' is a short chain acid residue containing between 2 ~nd 10, prefer-bly between Z and 6 carbons, and more prefer~bly bet~-en 2 nd 4 c-rbons ~ he follow1ng is ~ 11st of r~pr-s-nt-t1ve, but not ltm1t1ng, ¦ ex~mples of n~tur-l tr191yc-r1des of th1s invent10n (1) 2~cetyl 1,3 d1st~r1n I CH20 ( CO ) ~ CH2 ) 1 6CH3 CHO(CO)CH3 CH20 ( CO ) ( CH2 ) 1 6CH3 (2) 2~cetyl 1,3 d1p~1m1t1n CH2o(co)(cH2)l4cH3 I CHO(CO)CH3 CH20(CO) (CH2) 14CH3

(3) 2~prop10nyl 1,3~d1ste~rin CH20(C0)(cH2)l6cH3 ~
CHO(CO)CH2CH3 ;;
CH20 ( CO ) ( CH2 ) 1 6CH3 ' "; ' , , ~" .

(4) 2-prop10nyl 1,3-d1p~1mttin CH20(C0)(cH2)14cH3 CHO(CO)CH2CH3 ,' ~. ~ ' ' ' CH20(C0)(CH2)14cH3 .~,, ',:'',"'"",,,',, ,','''',""'",';'':

,'''.',.' '' i', ., :. ...

13 2~42~57 ,,1 ' :

(5) 2-~utyr~1 1,3-distearin CH20(cO) (CH2) 16CH3 , , 1HO ( CO ) ~ CH2 ) 2CH3 CH20(CO) (CH2) 16CH3 ~6) 2-~utyry1 1,3-d1p~1m1ttn CH20(CO) (CH2) 14CH3 :
IHO(CO)(CH2)2CH3 lH20(CO) (CH2) 1~CH3 (7) 2 1sobutyryl 1,3~d1ste~r1n CH20(CO) (CH2) 16CH3 ¦HO(CO)CH(CH3)2 IH20(co)(tH2)l6cH3 ' (8) 2-1sobutyryl 1,3-d1p~1m1t1n CH20(CO)(CH2)1~cH3 ¦HO(CO)CH(CH3)2 IH20(CO)(CH2)1~CH3 (9) 2-~cetyl 1,3-d1behen1n CH20~CO)(CH2)20cH3 CHO(CO)CH3 CN20(CO) (CH2)20CH3 (10) 2 -c-t~1 3-~r~ch1dyl 1-ste~ryl tr~glycerol tH20 ( CO) ( CH2 ) 1 6CH3 IHO(CO)CH3 IH20(CO)~CH2)18CH3 (11) I-behenyl 2-caproyl 3 non~dec~yl triglycerol CH2o~co) ~CH2)20CH3 ''~
IHO(CO)(CH2)5CH3 Il luzo(co))cu2)17~u3 2 ~ 7 (12) l-heneicosyl 2-isobutyryl 3-tricosyl triglycerol CH20(CO)(CH2)2lcH3 CHO(CO)CH(CH3)2 CH02(CO)(CH2)19CH3 (13) 2-acetyl 3-p-1m1tyl l-stearyl triglycerol CH20(CO) (CH2) 16CH3 CHO(CO)CH3 CH20(CO)(CH2)14cH3 (1~) 2-1actyl 1 3-d1ste~rin CH20(CO)(CH2)16CH3 CHO(CO)CH(OH)CH3 CH20(CO) (CH2) 16CH3 ~he above exa~ples and other tr1glycer1des of this ~ ;
1nvent10n c~n be synthes1~ed by tecnn1ques sueh as the d1rect or trJnsester1f1c~t10n of a select-d 1 3-d1glycer1de (second~ry ~lcohol) The synth-sis of several spec1fic t~110red tr1glycer1des have been publ1shed glyceryl ; ;~
v~lpro~tes h~ve been synthes1zed for use ~s ant1-convulsants (U S P~tent No 4 70l 469 Marr10tt et al ); tailored ~; ;
tr1glycer1des ~1th ~ polyunsaturated long ch~in f~tty acid ~t thc 2 pos1t10n and ~ satur~ted fatty c1d between C~
nd ClB at the 1- and 3- pos1t10ns h~ve been synthesizea for use as therapeut1c compos1t10ns (U S Patent Nos.
4 607 052 4 701 469 and 4 701 470 Mendy et al ); an~ ;
tr1glycer1des w1th ~t least 30% of a p~rt~cular combina: on of s~tur~ted med1um chain fatty ~ctd C6 0 C8 0 a-',: ,',':' ' ~
, ., ' ~ ~,... ......
; ~ :': ,' ' ~ , -'~
'., ': ' , , ", ... ......
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2042~

CIO 0 a saturated long chain fatty acid and a unsatur-ted long chain fatty acid have been synthesized for the1r 1mproved autoignition characteristics in shortenings and cooking oils (U S Patent No 4 832 975 Yang) The dlrect est-r1f1cat10n reaction can be perfor~ed by react1ng th- 2-hydroxyl 1 3-d191yceride w1th the ppropriate f~tty ac1d ac1d chloride or acid anhydr1de In the react10n between the acyl halide nd the 1 3-diglycer1de pyr1d1ne or anoth-r type of base can be used to neutral1ze the hydrochlor1c ac1d by-product The direct ester1f1cation of the l 3-d1glycer1de w1th the appropr1-te ac1d anhydr1de w~s found to be a preferred method for the prep~ration of the tr1glyc~r1de esters of th1s invent10n The cho1ce of fatt~ ~c1d mo1et1cs w111 ffect the b1010~1cal as ~ell ~s th- ph~s1c~1 prop~rt1es of the co~pos1t10n ~here thes~ f~tt~ ~c1d mo10tles ~re motabol12ed thc calor1c value of the co~pound ~111 1ncrease Pr-f-rred compounds are part1ally d190st1ble and del1ver 0 5 to 8 5 kcal/gram prefor~bly O S to 6 0 kcal/~ram and more narrowly 1 0 to S 0 kcal/gr~ upon be1ng metabolized The tr1glycer1des of th1s invent10n may be 1ncorporated alone or 1n comb1nat1Dn w1th another fat nd/or fat subst1tute in o any food compos1tion cr used in conjunction w1th any ediblD
materlal The term ~ed1ble material~ is broad and includes anyth1ng ed1ble whether or not intended for nutr1tion i e 1t can be an add1t1ve such as an antioxidant for fats ^~

2~42~
i6 o11s, an anti-spatter agent an emulsifier, a texture mod1f1er such as a plasticizer for chewing gum, a component for cosmetics, or other functional ingredient such as a carrier or d~luent for use in flavorings, pharmaceuticals, and the 11kc Representative of edible materials which can cont~1n the fat of th1s invent10n in full or partial repl~ce~ent of the curr-ntly us-d f~t re fro~en deserts, l e , sh~rbert, lce cream, ices, or m11ksh~k~s; pudd1ngs and p1~ f~ll1ngs; ~arg-r1ne nd m~r9~r1n~ bl-nds; flavored bread ~nd b1scu1t spreads; mayonn-1se; sal~d dressings; f111ed d~1ry products such as f111-d cream or m11k; da1ry or non-d~1ry che~se spr--ds; p--nut butt-r spre-ds; coffee 11ght~ners, liqu1d and dr1ed; fl-vored d1ps; frying o11s and t~ts; spr~y or top1c-1 o11; r-form-d and comminutod m~ats;
m~t subst1tut~s and extenders; ~hlpp-d topp1ngs; compound ~ ;
¦co~t1ngs; frost1ngs; confsct10n-ry co-t1ngs nd f1111ngs;
coco~ butter repl~c-~ents or bl-nds; c~ndy, especially f~tty ;
c~nd1es such ss those conta1n1ng pe~nut butter or chocol~te;
ch~w1ng gu~; b~kery products, 1 - , c~kes, bre~ds, rolls, p~str1es, cook1es, b1scu1ts, and savory crackers; mtxes or lngr~d1~nt pr~1xes for any of these; nuts, 1ncluding pssnuts; sn~ck foods, extruded ~nd b~k-d, corn, whe~t, nd r1c~; top1c~1 o11s; ~s well as flavor, nutr1ent, drug, or funct10nsl ~dd1t1vs del1very systems EXA~LES

I~The follo~ing examples are presented to furth-r itlustrate ¦¦and ~xplain the present invention and should not be taken as ~ m1ting in an~ reg-rd Unless otherwise inticated al, ~ ;
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2~42057 parts and percentages are by weight and are based on the weight at the particular stage of the process being descr1bcd Exa-nle I

The reduced c~lorie triglycer1de fat 2-acetyl-1 3-distearin ls pr~p~red 1n th1s ex~mple On~ gr~m of 39% pure 1 3-d1stear1n commercially ava11able by known techn1ques is we19hed out and placed 1nto a 100 ml round bottomed flask A magnetic stir bar 1s also plaeed 1n the fl~sk An excess (15 ml) of acetic ~nh~dr1de 1s ~dd~d and th- r-flux condenser is attachet to the fl~sk ~h- system 1s heated b~ means of a heating ¦ ~ntle controll-d by a volt~ge regul~tor unt11 the m1xture re~ches reflux ~he m1xture 1s then refluxed for three hours ~1th const~nt st1rrlng He~t 1s next removed ~nd the ~1xture 1s cooled to a~b1ent temperature The ~1xture 1s then tr~nsferred 1nto a separatory funnel with the a1d of 75 ml d1ethyl ether The solut10n 1s washed altern~t1vely w1th 10% sodium b1carDon~te ~nd water unt11 1t is neutral to litmus ~1nally the sample is dried at 90 C for one hour ~he c~p111ary melt1ng point of th1s compound was !j pprc~ s9 c ~ : ~

Il :
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18 2042~
Th1s procedure w~s repeated using the appropriate dlglyc-r1d-s and anhydrides to produce the follo~ing compounds ~1) 2-~cetyl 1 3 d1ste~r1n (Melt1ng po1nt approx1m~tely 59 C) (2) 2-~cetyl 1 3-d1p-1m1t1n (Melt1ng point ~pprox1m~t~1y 53 C) t3) 2-prop10nyl 1 3-d1ste~r1n (Mtlt1ng po1nt ~pprox1m~tely 52 C) ;
~'':' ;~"'' (4) 2-prop10nyl 1 3-d1p~1m1t1n (Melt1ng po1nt ~pprox1m~tel~ 45 C) (5) 2 butyr~1 1 3-d1ste~rln ~Melt1ng po1nt ~pprox1m~tely 51 C)

(6) 2-butrr~1 l.3-d1p~1m1t1n (M~lt1ng po1nt ~pprox1m~tely 40~C) ~;

~7) 2-1sobutyryl 1 3 d1stear1n (Melt1ng po1nt ~pproxtm~tely 47 C
. ' -,. ..
(B) 2 1sobutyr~1 1 3-dip~1-1t1n (llrlt~ng po1n~ approx~D~tely 3a~C) 19 2~42~
~A~PLE 2 S~eet ChocQ~ate A reduced calorie sweet chocolate flavored comest1ble may be prepared by combin1ng Q9redtent Parts Cocoa Po~der O S

Sug~r l 5 ~o th1s ~s added approximat l~ gS% of 2 butyr~l-1,3-d1palm1t1n 1 0 and th~ 1ngred1ents are m1x-t thoroughly and p-ssed through a rtf1ner to reduce the p~rt1cles to d-sired size The mster1~1 1s conch~d and the rema1ning 2 butyryl 1,3 dtp~lm1t1n 1s ~dded ~he m1xture 1s then t-mpered, poured 1nto molds and ~uench cooled EX~PL 3 '" ' l Choe~l~te ChlDs ~he chocolate prepared above m-y be ¦¦melted and depostted 1nto dr-ps in the usual process Il ', '. ,'' P~ . - .,- , . - . . . . . ~ .. ~ . -~') 2042~7 EXA~PLE 4 Su~r Cookjes Sugar cookies m-y be prepared by blending Q9redient ~rts Sugar 231 2-proplonyl 1 3-dlstearln 57 Corn 011 S~lt 3 7 ;

Sod1um B1carbonate 4 4 ~t~r 37 4 ~ ;

S 9X Doxtrose Solution (wt/wt) 58 7 ' ' ' Flour 391 ~;

All of the ingred~ents are creamed togcther The dough so formed ~ay be extruded (the dough is very tacky) and baked ~y the usual process ~;;
',''' '''','''""' I

'.,"',"'':' ~,','.,.~

~ I ~1 2~2~57 ~XA~PLE 5 Maratrine M~rg~rine m~y be prepared by combining the tngredSents for the following two phases Q~L_Phase In3redtents Parts 2-propSonyl 1 3-dSpalmStSn 15 0 2-butyryl 1 3-diptl~StSn 15.0 Corn 01l 29 0 So~be~n H~rdstock ~IV 65) 40.0 Emuls1~1er 1.0 QQ~QUS Ph~se Inored1ents . ...
~ter 95.8 ':"`
M1lk Sol1ds 2 0 : :,., ' S~lt 2.0 Citrit Ac1d 0 1 eta C~rotene 0 1 ;
I
~.
ll . ' ''~' : ,, . . , , . , . ', - '` ~ '. ' ~ ' ~ ',-2042~7 ~ he phases are emulsified in an oil aqueous phase ratio of 80 20, and passed through a cocl scraped surface heat I exchanger 1n the usual process EXA~PLE 6 fl~vor Btts ~lavor blts for lncorporation into baked ~-¦
goods may be prep~red by combln1ng the follow1ng lngred1ents lnar-d1ent Parts Sucrose 215 ~s~er ¦ Corn Syrup 160 ¦ Ex-~pl- 5 M-rg~rtn- 28 Fl~vor 12 Cltr1c Ac1d lO
' ;', :~ ''' ' Glycer1n 8 I! S.lt s Dye l ~ ~
'~

2042~7 ~" ~3 The f1rst thrce ingredients are heated to 290 F and the heat remov~d Margarine is mixed in, and the mixture allo~ed to cool to 160 I~O'f before adding the remaining ingredient5 (Almost any flavoring materi-l m-y be used as flavor, for cxsmple, buttcrscotch or pe~nut or other nut ) ~he mixture 1s th~n pour-d into cold alu~1num p-n and fro2en in dry lce ~he fro2en m1xture ls th-n crack~d and m1tled into b1ts ~ "

,~utterscQtch Cook1es Butterscotch cook1es may be prep~red by blend1ng ,Innred~nt ~rt 5 ~1our 22 0 2~eet~1 l,3 d1steartn 5 0 2-prop1Onyl l,3 dist--r1n 5 0 ..
Corn 011 lO 0 I .' S~lt 0 ~

Soo1u~ 3ic~rDc~te 0 1 20~2~7 Monocalcium Phosphate 0 1 V~nillin 0 1 ~ter ~ 0 and ~1xing well ~o this is added Sugar 30 0 ~ whlch is mixed unt11 dispersed Then 'I Exampl~ 6 Eutterscotch ù~ts 19 C

l are mixed 1n unt11 ~ust blended prior to depositing and i bak1ng b~ the usual process !
E~ LE~

V~nlll~ ~afers To prepare vanilla wafers blend ! Incred1ent Parts 2-acetyl 1 3-distearin ¦~ 2-propion~l 1 3-distearin , ." ' ' ' ' . ' . . " ' ~ ' ; ' ~ ~ ''' ", " "''. ' ' ''' , ' , ' , ' . ' .' ' , ' , 20~20a7 torn Oil 13 ~lour 100 6ranulated Sugar 72 H1gh Fruetose Corn Syrup 5 0 Nonfat ~ry M11k 1 0 S~lt 1 0 Ammon1u~ B1c~rbonate 1 0 . . ~, Dr1cd Egg Yolk 1 0 Y~n~lla Flavor 0 25 ~-ter 55 ¦~hc dough so formod mJy be rollet, wire cut to 1/4 inch ¦th1ekno~ d bakod by the usual process to give a van~
¦w~for cook1e ! , ,.

i Examole 9 Chocolate Chts Cookies Chocolate chtp tookies ma~ :?
prepared ustng the butterscotch cookte rectpe of examsle but substttuttng I . ' "' 210~2~

InQredient Parts ExamDle 5 Margarine 10.0 2-propionyl 1 3-diste~rin 5.0 Corn Oil S.O

for t~e fat ingredient Granulated Sugar 15.0 Bro~n Sugar 15.0 "' ' , for the sug-r and Ex~mple 4 Chocolate Chtps 19.0 for the butterscotch b1ts.

~8~PLE 10 Filled Cream. 70 make a ~f1lled cream~ composition.
¦¦homogeni~e a~out li In~red1ent ~ L

i 2-butyryl 1 3-dipalmitin 30.0 2042~7 ~7 Skim M11k 69 9 ¦~ Polysorb~te 80 o l ln ~ convent10n~1 t~1ry homZogen1zer ,~D ~

l~_LI~m Y~n111~ 1ce Crt~m m-y be prep~red by mixing Ino~e~1~nt P~rts Sug~r ~lOX) 15 0 Nonf~t Dry ~ 3.9 S~lt 0 4 lnto ~tor 39 0 for 3 m1nut~s ~hon ~dd 11qu1d 2-butyryl 1~3-dtp~lm1ttZn 28 4 ~nd cook to 200 F while mixing Hold for 1 minute Cool to ;
160 f and ~dd ~ ~

~8 2 ~ ~ 2 ~

Sugared Egg Yolks 12.5 Vanilla ~xtract 0.8 and mix 1 minute. Cool and freeze while rotating to desired overrun.

EXA~PLE 12 ~ illed Milk. To prepare a ~filled milk" composition, combine about Inqredient ~

Ex~mple 10 ~illed Cream 100 Skim mllk 900 ~nd rehomogenl2e.

~L~

Cheese Prôduct~ To prepare cheese products, treat Incredient Parts ¦~ Non~t milk 75.0 Il , ~9 20~2~7 Lo~ lemperature nonfat dry milk 4 0 2-butyryl 1 3-dip~lmitin 20 0 lo th1s ~s added S~lt 0 7 ~ct1c Ac1d Culture 0 3 The M1xture 1s fermented nd pressed to ~ fin~l compos1t10n of aoproxim~tely 37 0X mo1sture 63 OXtot~l sollds ~nd 32 0%
f~t eXA11PLE 1~.

~ ter Cro~ ~ Ic1n~ Butter cre~m ic1ng m~y ~e prepared by ~lend1ng I~9~ D~ Parts ,.' '~'' Sug~r 227 0 '.',~
ll 2 butyryl 1 3-dist~rin 17 0 l : ,~ ," .":: -2-propionyl 1 3 dip~lm1t1n17 0 Corn Oil 36 8 :",'';:','','',"
~'"'''.''''.'', , " :",~

2~1~20~7 :`

~ter 2B 4 . .~.
Nonfat Dry Milk I4 0 ~muls1fier 1 4 S~lt I O
' ' V~n111~ I O

A11 of the 1ngredients are cre~med in a mixer at medium speed unt11 the desired consistency is obt~ined EXA~PLE lS

L~uJ~LcL~ A dough prep~r-d by m1xing together ,~,.
Inared1ent P~rts Flour IOO

Sug~r 5 0 M~lt 1 5 2-propionyl 1 3-dipalm1t1n 7 5 . .
.., ,1 20~20~7 S~lt l o Sod1u~ 81c~rbon~te 0 9 Nonf~t Dry H11k 2 5 Hlgh fructose Corn Syrup 2 5 Monoc~lc1u~ Phosph~te 0 75 ~ter 28 1s sh~eted st~mped ~nd b-ked to produce cr~cker product ~L~g ' " '' ~r~Y~d Cr~e~er~ ~h- sh--t-d ~nd st~0ped cr~ck~r dough of ox~pl~ lS ~ be sprs~d ~1th 11qu1d 2 butyryl ~;
3-d1~ 1t1n ~ftor b~k1ng ~rLE 17 n~lLLL~ L M~yonn~1se c~n be prep~red from the ¦ fol10~1 f o rm~ 1 ~ t 1 o n: ? :, :. ' ,'~.' `
'' : ''"'',' ' . ~ . . .

20~20~7 lncred1ent Parts ~' 2 butyr~1 1 3-dip~lmitin 40 0 Corn 011 40 0 Egg yolk 5 5 Vlnegar 3 0 S~lt l S

Sug~r 2 0 fl~vor o 5 ~ater 7 5 the egg yolk Is f1rst m1xet w1th the othcr dry 1ngred1ents and a sm~ll amount of the water and v1negar 1n a cont~iner ¦L1qu1d 2-butyryl 1,3-d1palm1t1n and corn o11 aro slowly pourod 1nto the conta1ner, ~h11e sub~ect1ng the conta~ncr ¦contents to m1x1ng, to form an cmulsion ~h11e continuing to ¦~91tate the emuls1On, the rem-1n1ng water and vinegar is dded 20~20~7 ,Ex~mDLe 18, Pudd1na , Pudding c~n be prep~red from the following i formulat10n In~red1ent ~55 M11k 67 l Sug~r 11 St~rch 5 ~t~r 9 f1~vor 3 2-~cst~l 1,3-d1stesr1n 5 '' ~;' ths ingrod10nts c~n be blended together to form ~ pudding ''~

' '''~''', 3 ~1na ,011 2-butyr~l 1,3-dip~lmitin m~y be used for ,,'~,''"
l frying foods, , ~" ',', ! ~ i , , ." ". .

2042~7 ,- 34 eet fo9d Dry expanded ~nim~l food k1bs may be prepared from the follow1ng ingred1ents lnor-d1ent Parts ,, Hom1ny ~eed 37 52X He~t Meal 17 ~he~t Shorts 13 2 proplon~1 1 3 d1p~1m1t1n 16 Corn 6~rm He~l 9 6 ~he~t 6~rm He~l 3 Dr1ed H11k 0 9 t~t Pulp 1 7 Ftsh Scr-p O S

Br~er s Ye~st O S

S~lt O S
. , ' , V1t~mins and Minerals 0 1 l ; ,~' ~he ingredients are mixed together and water added to raise th- water content to 27%, before extrusion, pelleting, and fry1ng 1n the usual manner The above dcscriPtiOn is for the purpose of teaching the pcrson of the ord1nary skill in the art how to pract1ce the present lnvsnt10n nd 1t 1s not intended to deta11 all those obv10us mod1f1c~t10ns nd var1~t10ns of 1t which will become ~ppartnt to th- sk~ll-d work-r upon r~ad~n9 th- d~scr1pt10n ;;
It ls 1ntended, how-ver, th-t all such obv10us mod1f1c~t10ns ~nd var1~t10ns and ~11 1sometr1t var1~t10ns of ch-m1cal n~mes ~nt formul~s, as used h~rein, be included w1th1n the scope of he present invant10n and b~ the follo~ing claims '~
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Claims (20)

The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows.

1. An edible fat composition comprising one or more low calorie fats of the following formula:
where, R and R" are long chain saturated fatty acid residures having between 16 and 40 carbons; and R' is a short chain acid residue having 2 to 5 carbons.

2. An edible fat composition comprising one or more low ca-lorie fats of the following formula:
where, R and R" are fatty acid residues selected from the group consisting of palmitic, stearic, arachidic, behenic, lognocaric, carotic, montonic, and melissic acid; and R' is an acid residue selected from the group consisting of acatic, propionic, butyric, glycolic, lactic, hydracrylic, hydroxybutyric, propenoic, and butenoic acid.

3. A food composition comprising:
(a) a reduced calorie fat having at least 35% by weight of one or more compounds of the following formula:
where, R and R" are long chain saturated fatty acid residues containing between 16 and 40 carbons, and R' is a short chain acid residue containing from 2 to 5 carbons; and (b) at least one additional food ingredient.

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

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

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

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

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

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

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

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

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

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

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

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

16. A method of preparing a reduced calorie food product having an edible fat component, said method comprising re-placing at least a portion of the edible fat with one or more compounds of the formula:
where, R and R" are long chain saturated fatty acid residues having between 16 and 40 carbons; and R' is a short chain acid residue having 2 to 5 carbons.

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

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

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

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