Review Cocoa Butter

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Food Chemistry, Vol. 62, No. 1, pp. 73-97, 19980 1998 Elsevier Science Ltd. All rights reserved

Printed in Great BritainPII: SO308-8146(97)00160-X 0308-8146/9819.00+0.00

Analytical. Nutritional and Clinical Method Section

Review of cocoa butter and alternative fats for

use in chocolate-Part A. Compositional data

M. Lipp* & E. Adam

Commission of the European Union DG Joint Research Center Environment Institute Food and Drug Analysis/ConsumerProtection Unit I-21020 Ispra Italy

(Received 3 April 1997; revised version received and accepted 13 August 1997)

This work reviews the literature on the compositional data of vegetable fats usedor proposed as alternatives to cocoa butter in chocolate and confectionery pro-ducts. Cocoa butter is the only continuous phase in chocolate, thus responsiblefor the dispersion of all other constituents and for the physical behaviour ofchocolate. Unique to cocoa butter is its brittleness at room temperature and itsquick and complete melting at body temperature. There were, and are, strongefforts to replace cocoa butter in part for chocolate production for technologicaland economic reasons. Such cocoa butter alternatives are the so-called cocoabutter equivalents (CBEs), cocoa butter substitutes (CBSs) and cocoa butterreplacers (CBRs). These are mostly mixtures of various vegetable fats (oftenmodified) and can consist of palm and palm kernel oil, ill@ fat, shea butter, salfat and kokum butter. In addition, a large variety of other vegetable oils can beused. Their composition according to triglycerides, fatty acids, sterols and otherunsaponifiable components is discussed in this report. 0 1998 Elsevier ScienceLtd. All rights reserved.

INTRODUCTION

Nomenclature

Triglycerides (triacylglycerols) are the main compo-nents of cocoa butter and other oils and fats. Trigly-cerides are esters of glycerol and fatty acids. Thecarbon atoms of the glycerol part are numbered l-3.While fatty acids in the l- and the 3-positions are mostoften interchangeable and very difficult to differentiate,the 2-position is of special interest. The fatty acid inthis position is important for nutritional and functionalaspects. The following conventions for labelling trigly-cerides are used in this report: (i) according to the car-bon number (CN), e.g. a triglyceride-labelled as Cs2contains 52 carbon atoms in its fatty acid part andcould consist of two molecules of stearic acid (18 car-bon atoms) and one molecule of palmitic acid (16 car-bon atoms); and (ii) according to the fatty acidcomposition, e.g. a triglyceride labelled PSS containsone molecule of palmitic acid and two molecules of

*To whom correspondence should be addressed.

stearic acid. Fatty acids are abbreviated according toTable 1.

Labelling and legislation

This report presents a summary of the literaturedescribing the composition of vegetable fats potentiallyadded to cocoa butter in chocolate. Until now, anaddition of 5-10% of fats other than cocoa butter inchocolate is allowed in several Member States of theEuropean Union (Denmark, UK, Ireland, Sweden,Portugal, Finland, Austria). Recently the EuropeanCommission prepared a new draft directive on choco-late in which the amount of other vegetable fat besidescocoa butter is allowed up to 5% (EEC).

Due to functional differences the vegetable fats addedto chocolate are to be distinguished and are labelled asfollows (Brinkmann, 1992; Bouscholte, 1994):

Cocoa butter alternatives (CBAs): generic name forfats fulfilling the function of cocoa butter completely orin parts;

(a) Cocoa butter equivalent (CBE): non-lauric (not

containing lauric acid) plant fats, which are simi-lar in their physical and chemical properties to

73


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74 M . Li pp, E. Ank lam

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cocoa butter and mixable with it in every amountwithout altering the properties of cocoa butter;

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Cocoa butter extender (CBEX): subgroup ofCBEs not mixable in every ratio with cocoabutter;Cocoa butter improvers (CBIs): similar toCBEs, but with higher content in solid tri-glycerides; used for improving soft cocoabutters.

Cocoa butter replacer (CBR): non-lauric fatswith a distribution of fatty acid similar to cocoabutter, but a completely different structure of thetriglycerides; only in small ratios compatible tococoa butter.Cocoa butter substitutes (CBSs): lauric plant fats(containing lauric acid), chemically totally differ-ent to cocoa butter, with some physical similarities;

suitable only to substitute cocoa butter to 100%.

The classification according to function, the principalcomposition of the fats and some examples are sum-marized in Table 2. No attempt was made to includecomponents such as esterified propoxylated glycerincompositions used for the manufacturing of calorie-reduced chocolate (Cooper, 1993).

In this report no differentiation will be made be-tween the subgroups of CBEs; i.e. no differentationbetween CBIs and CBEXs. They are all referred to ascocoa butter equivalents. Due to the technological andeconomic advantages of partly replacing the cocoabutter by other vegetable fats, a tremendous variety ofsources has been investigated for their usefulness in thepast. This also includes processing of fats by enzymaticinteresterification.

The typical ranges of edible oils and fats withoutbotanical curiosities, thus resembling the majority ofthe harvest, are described in the Codex Alimentarius(Codex Alimentarius, 1987) or in Ul lmanns Encyclope-dia of Technical Chemist ry (Thomas, 1976) as well as inpublications of national regulation agencies. In thisreport those figures will not be given again.

Figures shown here are supposed to serve as anexample. Moreover, it is not expected that the dis-tribution of fatty acids or triglycerides will vary ran-domly within the given limits. There will always be asort of correlation, i.e. if one constituent is low anotherwill also be low or the inverse. To indicate this shift ofpatterns, emphasis was put on the representation ofindividual data rather than of a representative range.Whenever appropriate a citation is made where thetypical range is estimated.

Cocoa butter for chocolate production

The special position of chocolate among other foodproducts is not only based on its taste and nutritionalvalue. Moreover, physical parameters are important,such as brittleness (the snap when the chocolatebreaks) and the fast and complete melting in the mouth(Soeters, 1970).

The distribution of the ingredients of chocolate, i.e.the fine dispersion, is crucial for the taste of the pro-duct. The fat phase is the only continuous phase inchocolate, thus responsible for melting behaviour andthe dispersion of all other constituents. Cocoa butteritself exists in different crystal modifications. A carefultempering of the chocolate is necessary in order toobtain the fine crystals in the correct form (B-mod-ification). Without this tempering, cocoa butter tends to

Table 1. Nomenclature of fatty acids

Symbol Name CN:DB Symbol Name CN:DB

LPSLA

Caprylic acidLaurie acidPalmitic acidStearic acidLinoleic acidArachidic acid

Behenic acid

8:012:o16:018:O18:220:o

22:o

M

0E

Ln

Capric acidMyristic acidPalmitoleic acidOleic acidElaedinic acidLinolenic

Arachidenic acid

1o:o14:o16:l18:l

18:l (tr9)18:3

2O:l

CN, carbon number; DB, double bonds.

Table 2. Cocoa butter alternatives: examples, properties and composition - an overview (Brinkmann, 1992)

Plant fat type (examples) Function Main fatty acids Main triglycerides

Cocoa butter equivalent (CBE) Palm oil, illipebutter, shea butter,kokum butter,sal fat

Cocoa butter replacer (CBR) Soya oil, rape seed oil,cotton oil, ground nutoil, palm olein

Cocoa butter substitute (CBS) Coconut oil, palm

kernel oil, MCT

Non-lauric fat, Palmitic, stearic oleic, POP, POS, SOSdoes not alter the linoleic arachidic acidproperties of cocoabutter in mixturesPartially compatible Elaidic acid, stearic acid, PEE, SEEdifferent triglycerides palmitic, linoleic

Laurie fats, suitable for Laurie, myristic LLL, LLM, LMM

100% substitution only


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76 M . Lipp, E. Anklam

(Garcinia indica) butter as well as some commerciallyavailable mixtures blended from various, sometimesprocessed, vegetable fats.

Palm oil, fractions and related products (Elaeisgui neensis)

The composition of palm oil as well as factors influen-cing the quality of it are published in extensive reviews(Jacobsberg, 1975, 1983). A summary of the surveyperformed in the Malaysian Agricultural Research andDevelopment Institute and in the Palm Oil ResearchInstitute of Malaysia with respect to characteristics ofpalm oil and products derived by fractionation hereof is

given in Maclellan (1983). Palm oil can be divided byfractionated crystallisation into a fraction of palm oleinand palm stearin using different processes. These frac-tions may then be used for further processing such asinteresterification (Cotton, 1980; Chong et al., 1992).

St erol s and ot her unsapon a bles

The composition of sterols and other fractions of theunsaponifiables of palm oils and related products aresummarised in Table 6.

The analysis of free sterols (Grob et al ., 1994b) andsterol ester (Gordon and Griffith, 1992) was proposedfor the identification of oils in blends. While the greatervariety of these components offers a very characteristic

Table 3. Sterol @-desmetbylsterol, 4,4desmethylsterol and triterpene) composition of cocoa butter (Staphylakis and Gegiou, 1985)

Compound

4-Methylsterols

Free sterol(mg/lOO g fat)

4,4-Dimethylsterols or triterpenes

Compound Free sterol(mg/lOO g fat)

3 1 Norlanostenyl24(28)-Dihydroobtusifoliyl3 1-NorcycloartanylLophenylMethyllophenylEthyllophenyl3 1 Norlanosteryl3 1 Norcycloartenyl

ObtusifoliylCycloeucanlenyl

0.540.0040.181.390.421.070.720.54

2.070.96

Citrostadienyl 5.56Gramisteryl 1.23

4,14,24_Trimethyl-cholest-7,22-dien-3/I-ylUnidentified

0.7

0.18

/I-AmyrinCyclobranylLanostenyl2CMethyllanostenylLanosterylCycloartenylLupeyl24-Methylene-lano-stenyl-cyclolaudeny24-Methylene-cycloartanyl4,4-Dimethyl-24-ethylidene-5cx-cholest-7-en-3#?-yl

4,4,14-Trimethyl-k-cholest-7,24(25)-dien-38-yl4,4-Dimethyl-24-methylene-5ar-cholest-7-en-3/%yl4,4, 14-Trimethyl-24-methylene-5ar-cholest-7-en-3/I-ylUnidentified

0.60.40.7

trace0.5

18.90.14.0

5.80.6

0.20.7

10.0

1.5

4-Desmethylsterols



Cholestanyl Stigmasteryl 60.1Champestanyl Brassicasteryl 0.9Stigmastanyl 1.6 5,23-Stigmastienyl 1.8Cholesteryl 1.9 AS-Avenastenyl 5.6

Campesteryl 18.7 A7-Avenasteryl 0.7Sitosteryl 123.3

Table 4. Fatty acid composition (area ) of cocoa butter for some countries of origin

Country of origin Ecuador Brazil Ghana Ivory Coast Malaysia Java

Palmitic acid 25.6 25.1 25.3 25.8 24.9 24.1Steak acid 36.0 33.3 37.6 36.9 37.4 37.3Oleic acid 34.6 36.5 32.7 32.9 33.5 34.3Linoleic acid 2.6 3.5 2.8 2.8 2.6 2.7Linolenic acid 0.1 0.2 0.2 0.2 0.2 0.2Arachidic acid 1.0 1.2 1.2 1.2 1.2 1.2

Behenic acid 0.1 0.2 0.2 0.2 0.2 0.2


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Cocoa butt er alt ernat iv es-Part A 77

pattern for identification, it was pointed out (Grob etal., 19946) that by strong bleaching, all sterols and theiresters can be removed.

The influence of the refining process on the sterol,sterol ester and sterol glycosides of palm oil was inves-tigated (Homberg and Bielefeld, 19823). During therefining process, all fractions show characteristicvariation in content and composition. The content oftocopherol, tocophenol and tocotrienol is given in vanNiekerk and Burger (1985) and Reddy and Prahakar(19946). Palm oil is rich in y-tocotrienol, followed bya-tocopherol and a-tocotrienol and practically free of&tocopherol.

Fatty acids

The fatty acid composition of palm oils, palm mid-fractions and related products is summarised in Table 7.Palm trees are not only subject to breeding for greateryields, there are also attempts to breed to produce fatwith a composition of fatty acids more similar to cocoabutter. In Table 8 data are summarised for selectedMalaysian palm trees proposed for further propaga-tion, because of their favourable fatty acid composi-tion. There are not only differences from tree to tree,there are underlying patterns for the fatty acid compo-sition typical for a specific region. A survey with typi-cal ranges of the fatty acid composition of palm oil of

Table 5. Typical triglyceride composition (area ) of cocoa butter (Podlaha at al., 1984)

Country of origin Samoa Ivory Coast Ecuador Malaysia Ghana Nigeria Bahia

POL 0.8 0.6 0.7 0.6MOO, MMP 0.3 0.2 0.3 0.5PPL 1.6 1.9 1.9 1.5000 0.2 0.8 0.8 0.8SOL 0.5 0.9 0.8 0.7PO0 2.2 4.4 3.5 2.7PSL 2.8 3.6 2.8 2.8PPO 16.4 15.9 15.3 13.8soo, PPP 3.7 6.0 4.8 3.8SSL 2.1 1.8 1.5 2.0PSO 38.3 36.6 36.3 36.6OOA 1.6 1.0 1.2 1.6PPS 0.4 0.4 0.3 0.6sso 26.8 23.8 26.9 28.4SSP 0.7 0.8 0.9 1.0SOA 2.2 1.6 2.1 2.5

0.60.21.90.50.42.63.2

15.24.52.1

37.31.4

26.81.32.2

0.8 1.10.2 0.21.9 1.70.4 0.90.8 1.03.2 5.53.4 3.4

14.8 14.05.1 8.41.9 2.1

37.4 34.61.2 1.50.7 0.3

26.4 23.70.4 0.21.9 1.6

Table 6. Typical composition of sterols, methylsterols, triterpenes, tocopherols, squalene and sesamolene in palm oil, palm mid-fractionand related products

References Abu-Hadeed and Homberg and Homberg and van Niekerk andKotb, 1988 Bielefeld, 1982~ Bielefeld, 1990a Burger, 1985

(wt%) (area%) (% of total fraction) (wt%)

S-Tocopheroly-TocopherolSesamolene

4-DesmethylsterolsBrassicasterolCampesterolStigrnasterolB-SitosterolA-StigmasterolA5-AvenasterolCholesterolA-Stigmastenol

4-MethylsterolsObtusifoliolCitrostadienolGramisterolCycloeucalenol

4,4-Desmethylsterolsor triterpenes

, ?-AmyrinCycloartenol24-Methylencycloartanol

6.70.06.70.0

0.023.311.746.7

0.0

0.00.0

0.0 0.05.0 42.40.0 9.0

24.710.559.20.22.61.6

- 54.35.76.14.3

-trace23.3

0.115.57.4

44.4

0.10.19.0

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Table 8. Fatty acid composition (area ) of selected Malaysianpalm trees, being potential applicants for propagation by

breeding due to their compositions (Pa&ark, 1990)

Fatty acid 14:o 16:0 18:O 18:l 18:2

No. 1 0.5 32.7 5.7 45.4 15.7

No. 2 0.5 32.0 9.0 48.8 9.7No. 3 28.7 15.4 40.4 15.5No. 4 31.5 7.1 54.1 7.3No. 5 35.8 5.4 42.8 16.0

different regions was published (Reddy and Prahakar,19943).

In order to make the fatty acid composition evencloser to cocoa butter, palm mid-fraction is inter-esterified with either palmitic or stearic acid. The fattyacid composition of a transesterified palm mid-fractionwas indicated in several publications (Siler-Marinkovicand Mojovic, 1992; Hashimoto, 1993; Mojovic et al.,

1993; Siler-Marinkovic et al., 1993). Using either pal-mitic or stearic acid and enzymes, which selectivelyaffect the fatty acid in the l- or 3-positions, it is possi-ble to produce a cocoa butter-like fat in which the fattyacid composition resembles closely that of cocoa butter.

Triglycerides

Typical triglyceride compositions of palm oil and itsfractions are summarised in Table 9. It is obvious thatthe triglyceride composition depends strongly not onlyon the type of fraction. Comparing rows five and sixreveals that there are also big differences depending onthe analytical technique used. Palm oils were char-acterised by the ratios of the triglycerides 000, PLO,PLP, PPP, POP, PO0 (Aitzetmiiller et al ., 1988). How-ever, for the identification of the addition of palm oils,the analysis of fatty acid seems to be better suited,because palm oils can be easily detected for their lauricacid content. Therefore, it seems redundant to showthese ratios here.

Results of the stereospecific analysis of the triglycer-ides were shown by Christie et al. (1991) and Christie(1994). In the sn-2 position, oleic acid is clearly domi-nant followed by approximately equal amounts oflinoleic and palmitic acid. With respect to the sn-3position, the sn-1 position is enriched in linoleic acid bya factor of three, in oleic acid by a factor of two anddepleted in myristic acid by a factor of six and in pal-mitic acid by a factor of two.

The phospholipid composition was summarised byGoh et al. (1982). The authors determined phosphati-dylcholine, phosphatidylethanolamine, phosphatidyli-nositol and phosphatidylglycerol as major components.However, they stated that a low content of these com-pounds seems desirable to obtain better oxidation sta-bility and bleaching properties.

Triglyceride composition grouped by carbon num-bers for palm mid-fraction, palm oil, the stearin and the

olein fraction were given in Hogenbrink (1984), Mottaet al. (1987) and Reddy and Prahakar (1994b). The

major components, present in equal amounts are C50 andCs2 for palm olein, while CsO is predominant for theother fractions. The triglyceride composition of aninteresterified product of a palm oil fraction and stearicacid is given in Macrae (1983, 1986). This interesterifica-tion leads to a products content of SSS, POP, POS, SOS,SLnS and SO0 resembling cocoa butter perfectly.

II& Shea stenoptera)

There is some confusion in the literature about the cor-rect labelling of illipt fat and sal fat, respectively. Illipkis also called Borneo tallow, engkabang or tenkgawangtallow. This fat is obtained from the seed kernels of anumber of trees that grow in Borneo, Java, Malaysia,the Philippines and other localities of this area. How-ever, the most important species from which the fat isobtained is Shorea stenoptera.

IllipC is the European trade name for Mowrah butter(Banerji et al., 1984), while in another reference it isreferred to as the fat obtained from M adhuca longifoli aand/or Illipk malabaricum only (Thomas, 1976). Thisreference assigns the name Mowrah butter to the fatobtained from M adhuca lati folia, which shows a verysimilar composition. The term illip? was originallyderived from Tamil names for nuts of Bassia longifolia(family Sapotacaea) and for Mowrah nuts (Bassia lat i-folia) produced in South India (Anderson, 1975). IllipChas since been applied to other oil-bearing nuts, withsimilar properties, originating from East Malaysia. Incommerce it is now accepted that the term illipt standsfor a particular commodity, namely the products fromShorea stenoptera (Nesaretnam and bin Mohd Ali,1992). Therefore, in this section only references aregiven where the authors explicitly referto illipC.

St erol s and other unsaponi Ji ables

The composition of sterols and other fractions of theunsaponifiables of illipC fat is summarised in Table 10.

Fatty acidsThe fatty acid composition of illipC fat has someresemblance to cocoa butter as stearic acid pre-

dominates. The typical fatty acid composition of this fatis summarised in Table 11. As there was a lot of confu-sion about the plants to whom the name illipt wasapplied (see above) data of other species of Shorea arealso given. In illipC fat, oleic acid and stearic acid arepresent in more or less equal amounts followed by pal-mitic acid. All other fatty acids are present as minorcomponents (below 2%). The concentrations of 59different fatty acids, covering unsaturated as well asbranched fatty acids are given in Iverson and Harrill(1967).

Triglycerides

The composition of different species of Shorea and onecommercial sample, separated according to carbon


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Cocoa butter alternatives-Part A 81

number, is given in Nesaretnam and bin Mohd Ali(1992). The content of C 5. was found to be about6-lo%, and C52 and C+ are present in approximatelyequal quantities of about 40%.

Shea butter (Butyr ospermu m purkii)

Shea butter is often also called Karite butter, Galambutter and by other native names. It is obtained fromthe seeds of a tree mainly found in West Africa. As thefruits can be harvested only after 15 years, farming isnot economically viable.

Sterols and other unsaponljiablesThe content of unsaponifiables in the oil may consist ofup to 1 , containing components similar to caoutchuksuch as kariten (Table 12). The overall percentage of theunsaponifiables was determined to be of approximately

65% triterpene alcohols, approximately 8% sterols andapproximately 27% hydrocarbons (Jacobsberg, 1977).

An overview of the non-glyceride saponifiables inshea butter can be found in Peers (1977). Triterpenealcohols and sterols are present as esters of bothcinnamic acid and other fatty acids in a commercialsample of shea butter. Cinnamic acid was neither found

in the free form, nor esterified to glycerol. These non-glyceride unsaponifiables were found to represent 6%of the shea butter, while the free sterols and triterpenesaccounted for only 1% as weight.

Fatty acidsThe typical fatty acid composition of shea butter aswell as fractions of it is summarised in Table 13.This table reveals that the fatty acid composition ofshea butter does not change only with the fractionbeing analysed. Geographical origin seems to have abig influence as well. The concentrations of 59 dif-ferent fatty acids, covering unsaturated as well as

branched fatty acids are given in Iverson and Harrill(1967).

Table 10. Sterol composition for Illiph (Shea stenopiera)

References Frega et al., 1993~(area%)

Homberg and Bielefeld, 1982~(area%)

Soulier et al., 1990(area%)

4-DesmethylsterolsCholesterolBrassicasterolCampesterolSt&master01/?-Sitosterol

A5-AvenasterolIsofocusterolA-StigmasterolA-Avenasterol

4-MethylsterolsObtusifoliol2CMethylenelophenolCycloeucalenolCitrostadienol

4,4-Dimethylsterols or triterpenes/?-AmyrinButyrospermolCycloartenolcr-Amyrin + lupeolZCMethyleneparkeol

24-Methylenecycloartanol@-TaraxasterolCycloartanolOthers

1.8 1.5 -9.6 0.3

19.5 14.5 12.7trace 7.5 4.264.2 71.8 44.20.8 2.4 -- 3.6

1.0 -0.1 -

0.50.9

- 0.60.8

3.12.21.1

17.40.9

4.10.9- 0.8

4.1 - 2.0

Table 11. Fatty acid composition of illipk (Shea stenopteru) fat and other Shorea species

12:0 14:0 16:0 16:l 18:0 18:l 18:2 18:3 20:0 Description

- 5.7 - 41.0 49.0 4.3 - -- 19.3 - 43.5 35.2 1.0 - 1.3- 22.0 - 40 38 - - -0.1 23.1 - 40.9 33.4 0.5 1.6 -0.1 22.1 1.1 39.4 35.8 0.6 1.8 0.1

0.1 0.1 16.0 0.2 46.7 33.2 0.9 0.2 0.2- 19.9 0.1 43.7 35.7 0.4 - -

(wt%)(% of total FA)(wt%)Shorea singkuwung (area%)(%) Shorea mecistopterix (area%)Shoreu mucrophylla (area %)Commercial sample (area%)

References

Baneji et al., 1984Bracco et al., 1970Meara, 1979Nesaretnam and bin Mohd Ali, 1992Nesaretnam and bin Mohd Ali, 1992Nesaretnam and bin Mohd Ali, 1992Nesaretnam and bin Mohd Ali, 1992


10/25


Triglycerides

By fractionated crystallisation the shea stearin may beobtained consisting mainly of 2-oleoyl-distearin andbeing used as CBE. The triglyceride composition of sheastearin was found to be 85% Cs4, 11% &, 2.5% C=,6and 0.6 Csa in (Hogenbrink, 1984). The composition ofshea butter was found to be 86% C&, 11% Cs2 and 3%Cs6 (Kanematsu et al., 1978~).

The composition for interesterified products is givenas an example in the patent application (Macrae, 1983).The fatty acids of such products had been rearrangedusing a 1,3-specific lipase and yielded an olein fractionthat consists of approximately 40% SO0 and approxi-mately 20% SOS, as well as a stearin fraction consist-ing of predominantly (> 80%) SOS.

By computational simulation, 23 triglycerides wereidentified. SOS and SO0 were shown to make up to60% of the fat (Swadogo and Bezard, 1982).

Sal fat (Shea robusta)

Sal fat is also called Borneo tallow or tenkgawang tal-low. This fat is obtained from the seed kernels of a

number of trees that grow in Borneo, Java, Malaya,Philippines and other localities of this area. However,there is some confusion in the literature between Shorearobusta, Shorea stenoptera and M adhuca longifol ia.They are all referred to as borne0 tallow, sometimeseven illipe, depending on the date of publication [seeIllipe (Shorea stenoptera) for more details.

Sterol s and ot her unsaponi Jia blesThe typical composition of sterols and other fractions ofthe unsaponifiables of shea butter is summarised inTable 14. The unique occurrence of 3-keto triterpenes insal seed fat was observed (Kolhe et al ., 1981).

Fatty acidsThe fatty acid composition of sal fat has some resem-blance to cocoa butter as stearic acid predominates. Thetypical fatty acid composition of this fat is summarised

in Table 15. The fatty acid composition of the fractionsof sal fat differs by only about 10% from the fatty acidcomposition of the whole sal fat (Chaudhuri et al.,1983). Sal fat contains 24% of 9,10-epoxystearic acidand 9,10-dihydroxystearic acid (Bringi et al., 1972;Bringi, 1976; Belvadi et al., 1979). Such compounds

Table 12. Sterol content of shea butter

References

SterolsCholesterolp-Sitosterolcu-SpinasterolA7-Stigmasterol24-Methyl-cholest-7-enolA7-AvenasterolOthers

4-MethylsterolObtusifoliolGramisterol/CycloeucalenolOthers

Triterpenes#?-AmyrinButyrospermolcY-AmyrinLupeol + unidentified compoundOthers

Derbesy andRichert, 1979

Cont. (wt%)

1.54.0

43.140.3

3.8

-

Abu-Hadeed and Kotb, 1988; KanematsuItoh et al., 1974 et al., 1978a

(wt%) (area%)

2.2- -

43.0 48.537.0 49.3

6.0 -11.0 -3.0 -

22.0 -4.0 -

74.0 -

8.0 -26.0 -46.0 -16.0 -4.0 -

Table 13. Fatty acid composition of shea butter

Fatty acids References

8:0 1o:o 12:o 14:o 16:O 18:O 18:l 18:2 18:3 20:o 20: 1

- 5.7 41.0 49.0 4.3 - - - Banerji et al., 1984 (wt%)- 4.0 58.0 33.0 3.0 - 2.0 - Hogenbrink, 1984, Shea stearin (area%)2.3 1.0 9.9 3.7 6.6 46.8 51.4 8.4 2.1 0.5 - Jacobsberg, 1977, Ivory Coast (area%)

- 4.2 22.5 68.0 4.9 0.1 - - Jacobsberg, 1977, Tchad (area%)- 3.8- 44.1 43.8 6.65 1.55 - - Jacobsberg, 1977, Benin (area%)- 4.0 43.2 43.9 6.6 0.3 1.6 0.4 Kanematsu et al ., 1978a (area%)- 8.0- - 37.0 50.0 5.0 - - - Meara, 1979 (wt%)


11/25

Cocoa butt er alt ernat iv es-Part A a3

affect the supercooling properties (Reddy and Prabha-kar, 1985). The fatty acid composition of sal fat candiffer at least by about 5% (wt%, absolute). Typicalranges are stated to be Cl6 (2.2-8.3%), Cis(34.7-48.4%), Cis,, (35.3-42.2%), C1sz2 1.9-3.2%) andCzo (5.5-10.8%) (Lakshiminarayana, 1977).

The fatty acid composition of sal fat interest-erified with palmitate and/or stearate is given in Srid-har et al. (1991). These fats resemble cocoa butterclosely in their fatty acid composition, consisting ofabout 33% each of oleic and stearic acid, and about24% palmitic acid.

al., 1979). It seems that during storage the 9,10-epox-ystearic acid is slowly converted to the 9,10-dihydrox-ystearic acid (Bringi, 1976). A total loss of the epoxyacid after 1 year of storage was observed. The triglycer-ide composition according to carbon numbers is givento be approximately 70% Cs4, approximately 13% eachfor Csz and C& and approximately 2% CsO (Kanematsuet al ., 1978a).

The variation of triglyceride composition typical forsal fat is given as SOS (42-52%), SOA (20%), POS (8-14%), AOA (l-14%), PO0 (&5%) and A00 (04%)(Lakshiminarayana, 1977).

Triglycerides Kokum butter (Garciniu n& a)The triglyceride composition of sal fat is summarised inTable 16. Sal fat contains up to 9% triglyceridescontaining 2 mol stearic acid in the 1,3-position and1 mol of either 9,10-epoxystearic acid or 9,10-dihydrox-

ystearic acid in the 2-position (Bringi, 1976; Belvadi et

Kokum butter is also known as Goa butter. Kokum isan evergreen tree found in the tropical forests of India.The kokum seed (8-10 seeds per fruit) is the source for

kokum butter. Traditionally, the oil is extracted by

References

Table 14. Typical composition of sterols and other fractions of the unsaponifiables of shea butter

Homberg and Bielefeld, 1982~ Kanematsu et al., 1978~ Soulier et al., 1990(area%) (area%) (area%)

SterolsCholesterolBrassicasterolCampesterolStigmasterol&SitosterolIsofocusterolA5-Avenasterol

A-Stigmasterol4-MethylsterolsObtusifoliol24-MethylenelophenolCycloeucalenolCitrostadienol

4,4-Dimethylsterols or tritperenes/?-AmyrinButyrospermolCycloartenolol-Amyrin + lupeol2CMethyleneparkeol24-Methylenecycloartanol+-TaraxasterolCycloartanolUnknown

0.9 trace0.5 -

16.5 20.016.1 12.861.5 67.2-

2.5

1.3

--14.85.6

40.53.2--

0.71.01.40.9

9.20.07.17.31.22.72.70.01.7

Table 15. Fatty acids in sal fat


16:O 18:0 18:l 18:2 18:3 20:0 2O:l 22

7.6 42.6 37.0 3.5 1.3 8.0 - -6.3 44.6 41.6 1.7 0.0 5.7 - -8.3 34.7 41.9 2.8 0.0 12.3 - -4.6 44.2 42.1 2.8 0.0 6.3 - -5.2 42.8 40.4 3.8 0.8 7.0 - -6.0 43.0 40.0 2.0 - 7.0 - -5.9 44.6 39.7 2.4 - 6.6 0.5 0.65.6

44.3 40.4 1.5 - 7.7 - -4.6 43.2 42.0 2.2 1.3 6.7 - -

g ;(wt%)(mol%)(wt%)(area%)(area%)

(molh)(wt%)

Bhattacharyya and Banerjee, 1983Bhattacharyya and Bhattacharyya, 1991Banerji et al., 1984Baliga and Shitole, 1981 from Hildtich and Stainsby, 1936)Bringi et al., 1972Hogenbrink, 1984Kanematsu et al., 1978~Sridhar et al ., 1991Chaudhuri et al ., 1983


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84 M. L& p, E.

Table 16. Typical triglyceride composition (wt ) of sai fat(Sridhar and Lakshminarayana, 1991)

Triglyceride

POPPOS

SOSSOAAOAPLPSLP

% Triglyceride %

4.8 PO0 3.516.0 so0 14.9

36.3 A00 0.69.0 SLO 0.61.0 000 2.04.2 PSS 1.45.0 Others 1.4

a typical West African cocoa butter could be matchedclosely (Cormeau, 1982). Some commercially usedhigh-priced mixtures of tree-borne seed fats and mix-tures of fractions of these fats are described inChaudhuri et al. (1983). However, because of theirhigh price, they are of moderate economic interest. Afairly extensive review was published by Keel (1977),covering the fatty acid and sterol composition ofapproximately 60 commercially available cocoa butterequivalents.

boiling the kernels in water and the oil is skipped offthe top. Nowadays solvent extraction is also used(Sampathu and Krishnamurthy, 1982).

St erol s an d other unsapont @ables

The composition of the sterols and other fractions of theunsaponifiables are summarised in Table 18. The cocoabutter equivalents are identified by their trademark.

Sterol s and oth er unsaponi Jiabl esN o reliable thorough investigation of the sterol contentand content of the unsaponifiables of kokum butter

could be found in the literature.

Fatty acids

Fatt y acidsThe fatty acid composition typical for kokum butter isgiven in Table 17. The range of composition of fattyacids in kokum fat is stated to be Cl4 (O-1.2%), Ci6(1.7-5.8%), Cis (51-61%), Cis:i (36.8415%) and Cts:~(0.551.7%) (Lakshiminarayana, 1977).

The fatty acid composition of some CBEs is given in

Table 19. It can be seen that most of the fats are verysimilar in their fatty acid composition and resemble thatof cocoa butter (Table 4). However, most of the CBEscited here show a somewhat elevated content of palmiticacid.

Triglycerides

The composition of Kokum fat interesterified withpalmitate and/or stearate was also investigated. Inter-esterified kokum was claimed to resemble cocoa butterespecially well in both its fatty acid and triglyceridecomposition as well as its melting behaviour (Sridhar etal., 1991).

The triglyceride composition of some CBEs is given inTable 20. However, reference is only made for thethree main triglycerides in the literature. It can be seenthat the triglyceride composition is fairly different tothat of cocoa butter (Table 5). A procedure for theapplication of relatively pure SOS and POS fatsobtained from palm mid-fraction is described inSoeters (1982).

TriglyceridesOnly one publication could be found where thetriglyceride composition of kokum butter is given insome detail: SOS (77.3%), SO0 (12.1%), POS (8.1%)and SLO (2.5%) (Sridhar and Lakshminarayana,1991).

COCOA BUTTER REPLACERS

The range of composition of triglycerides in kokumfat is given in Lakshiminarayana (1977). SOS wasfound to be 58-81%, POS 8-15% and SO0 1421%.

The fatty acid composition of some non-identifiedcommercially available cocoa butter replacers is sum-marised in Table 21 with the corresponding triglyceridecomposition in Table 22.

Commercial blends COCOA BUTTER SUBSTITUTES

In commercial blends several vegetable fats or frac-tions of the fats are mixed in order to resemble cocoabutter as closely as possible. For example, by blendingfractions of palm oil and shea butter with illipe butter,

The fatty acid composition of a cocoa butter substitutemade by selective hydrogenation and fractionation ofpalm olein is described in Leong and Lye (1992). Theprocedure yielded a stearin fat fraction suitable for

Anklam

14:o 16:0

0.4 1.4- 3.1- 2.0

Table 17. Fatty acid composition of kokum fat


18 18:l 18:2

60.4 37.8 (wt%) Banerji et al., 198456.1 39.1 1.7 (mol%) Baliga and Shitole, 198157.5 39.0 1.2 (mol%) Sridhar et al., 1991


13/25

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14/25


commercial coating fat. However, it was not possible toremove the waxy tail from the product completely. Thefatty acid and the triglyceride composition of six com-mercially available cocoa butter substitutes have beeninvestigated (Nesaretman and Kun, 1990). No sig-nificant differences between the fats were reported. Theyconsist of approximately 50% lauric acid and 20%myristic acid. The triglyceride composition is dominatedby c34, c36 and c38.

The fatty acid composition of clearly identified cocoabutter substitutes is given in Pongracz (1982) and Pau-licka (1976). As a lauric CBS, the fatty acid composi-tion is dominated by the content of lauric acid (approx.50%) and myristic acid (approx. 20%).

The fatty acid composition of seven cocoa buttersubstitutes made from different vegetable fats is givenin Table 23.

CBS from sal at (Shorea robusta)Sal fat can also be used for the production of a cocoabutter substitute (Reddy and Prabhakar, 1990). The

fatty acid composition of two CBSs made of sal fat isgiven in Table 24 for two different samples. Moreinformation about sal fat is given in Sal fat (Shorearobusta).

Palm kernel oil

Palm kernel oil is obtained from the kernels of the palm,Elais guineensis. It is similar to coconut fat but containsmore oleic acid.

Sterol s and ot her unsaponij i ablesThe typical composition of the sterol content and otherfractions of the unsaponifiables of palm kernel fat isshown in Table 25.

Fatty acidsThe typical composition of fatty acids of palm kernel oil

is given in Table 26. The concentration of 59 differentfatty acids, covering unsaturated as well as branchedfatty acids is given in Iverson and Harrill (1967).

Table 19. Fatty acid composition of some commercially available CBEs (blended from different fractionated vegetable fats)

Trademark Fatty acids References

C 16:0 C 18:O C 18:l C 18:2 Others

Coberine 32.0 28.2 36.1 2.0 1.7 van Dongen, 1991 (wt%)35.8 31.2 30.0 1.6 1.4 Gegiou and Staphylakis, 1985 (area%)31.8 29.8 33.5 2.9 1.1 Faulkner, 1981 (wt%)31.8 28.9 33.5 3.3 2.5 Cruickshank and Biol, 1979 (area%)

Choclin 38.7 22.2 35.1 2.1 1.8 van Dongen, 1991 (wt%)39.2 22.1 33.8 3.4 Gegiou and Staphylakis, 1985 (area%)

Calvetta 58.5 8.5 29.1 1.9 :;Synthetic cocoa butter 26.0 34.0 35.0 3.0 214

Gegiou and Staphylakis, 1985 (area%)Fincke, 1977 (area%)

Illexao 30-93 14.0 46.0 36.0 3.0 1.0 (18:3) Meara, 1979 (wt%)CBE A 28.2 30.6 34.6 3.8 2.8 Pongracz, 1982 (area%)Shea + palm fraction + illipe oil 32.3 30.2 33.0 3.0 1.4 Paulicka, 1976 (wt%)CBE-A 31.3 31.0 32.6 n.d. 5.1 Talbot, 199 1 (area%)CBE-B 35.4 27.0 32.4 n.d. 5.2 Talbot, 1991 (area%)

Table 20. Triglyceride composition of some commercially available CBEs (blended from different fractionated vegetable fats)

Name Triglycerides References

POP POS SOS Others

Coberine 35.0 19.0 28.0 18.0 van Dongen, 1991 (wt%)Choclin 45.0 14.0 21.0 20.0 van Dongen, 1991 (wt%)CBE-A 37.0 17.9 40.3 4.8 Talbot, 199 1 (area%)CBE-B 43.1 16.2 35.3 4.8 Talbot, 1991 (area%)

Table 21. Fatty acid composition (area %) of some non-identified, commercially available cocoa butter replacers (Nikolova-Damyanovaand Amidzhir, 1992)

CBR Fatty acids

14:o 16:0 18:O 18:l 18:2 18:3 20:o

A 0.8 42.0 22.5 31.3 2.8 0.6 0.0

: 0.7.3 40.23.5 22.38.7 25.03.0 3.2.5 trace.5 0.0.0D 0.1 24.7 36.1 35.4 1.4 2.1 2.1


15/25


OTHER OILS AND FATS

Besides the fats described above, the use of a wide vari-ety of plant fats is proposed in the literature. Those fatsare proposed as CBAs either directly or after appro-priate fractionation or interesterification. Due tonumerous references no attempt was made to stateexplicitly the composition of fatty acids, triglycerides orthe unsaponifiables for each fat individually. Theappropriate references are given in Table 27.

The following list gives reviews of fats and oils beingproposed as CBAs, but not thoroughly characterised,as well as reviews about other constituents of oils andfats mentioned in the previous sections.

Reviews

Compositional data (triglycerides, fatty acids,

unsaponifiables) as well as data on isotopic ratiosof fats of 45 cocoa butters, 15 CBEs and severalother vegetable fats, CBSs and CBRs (Eiberger,1996).

Fatty acid composition of 58 butters from differentplants of the potential for their use in the foodindustry (Banerji et al ., 1984).Fatty acid, triglyceride and phospholipid compo-sition of oils of 10 edible seeds from North Viet-nam (Imbs and Pham, 1995).Sterol composition of 19 different vegetable oils(Itoh et al., 1973).Fatty acid and triglyceride composition of baku,Lauracea, Myristacaceae seed fat and Still ingiatallow (Meara, 1979).Content of total hydroxy fatty acids for 76 differ-ent oils and fats (Schwartz and Rady, 1992).

Special constituents

Free sterols and olefinic degradation products inrefined sunflower, peanut, safflower, grape seed,

soybean, rapeseed, corn and walnut oils (Grob etal., 1994a).Occurrence of artificial trans-polyunsaturated fattyacids in walnut oil (Wolff, 1993).

Table 22. Triglyceride composition (area ) of some non-identified, commercially available cocoa butter replacers (Nikolova-Damyanova and Amidahir, 1992)

CBR Triglycerides

POP SOP SOS SOA

A 58.1 14.8 26.8 0.0B 73.8 9.0 17.2 0.0C 52.3 18.3 26.2 0.0

D 24.7 26.7 41.2 7.3

Table 23. Fatty acid composition (wt ) of seven commercially available CJ Ss made from different vegetable oils and fats(Paulicka, 1976)

Fatty acids Hard butters from palm and shea fractionsand whole refined illipe oils

Sample no.

1 2 3 4

Hard butters from hydrogenated,fractionated cotton seed and soybean oil

Sample no.

1 2 3

12:o 0.0 0.4 0.3 0.2 0.6 0.2 0.214:o 1.1 0.7 0.2 0.4 0.7 0.6 1.016:O 53.1 40.9 4.3 32.3 18.7 17.5 23.416:l 0.2 0.0 0.0 0.0 0.4 0.4 0.417:o 0.2 0.0 0.0 0.0 0.2 0.0 0.018:O 5.9 21.3 54.3 30.2 13.3 14.4 11.718:l 33.0 32.3 35.4 33.0 62.1 66.1 62.018:2 5.9 3.5 4.5 3.0 3.4 0.4 1.118:3 0.2 0.0 0.0 0.0 0.1 0.0 0.020:o 0.4 0.9 1.0 0.8 0.5 0.4 0.0

Table 24. Fatty acid composition (area ) of two cocoa butter substitutes from saf (Sorea robus ta fat (Reddy and Prabhakar, 1990)

Fatty acids

16:0 18:0 18:l 18:2 20:o

Sample 1 7.0 47.8 36.9 trace 8.2Sample 2 6.9 50.8 35.0 trace 6.8


16/25

M . Lipp, E. Anklam

Table 25. Typical composition of sterols and other fractions of the unsaponiiiables of palm kernel fat

References Abu-Hadeed and Homberg and Homberg andKotb, 1988 (wt%) Bielefeld, 1982a (area%) Bielefeld, 1990a (area%)

OthersSqualene

S-Tocopheroly-TocopherolSesamolene

4-DesmethylsterolsBrassicasterolCampesterolStigmasterol#?-SitosterolA-StigmasterolA-AvenasterolCholesterol

4-MethylsterolsObtusifoliolCitrostadienolCycloeucalenol

Gramisterol4,4-Dimethylsterols or triterpenes/?-AmyrinCycloartenol24-methylencycloartanol

1.2

0.01.80.0

0.01.31.46.40.0

0.30.1

0.12.00.4

Typical triglyceride composition of hydrogenatedpalm, pamlolein, peanut and other plant oils asdetermined by packed-column GC (Fincke, 1980).

Processing and interesteriiication

Influence of the three refining processes (bleaching,De Laval, Zenith) on the unsaponifiables(Johannsson and Hoffmann, 1979). Sterols werereduced to about one-third of the initial con-centration, while the concentration of sterol estersremains unaffected. However, changes in the com-position of fatty acids of the sterol esters werefound.Composition of a calorie-reduced fat (Mastersonet al., 1994). Reduction of caloric intake isachieved by introducing behenic acid.

Table 26. Typical fatty acid composition of palm kernel oil

References Abu-Hadeed and de Jong andKotb, 1988 de Jong, 1991

(wt %) (area%)

C8 2.4 5.7Cl0 2.5 4.7Cl2 36.9 46.1Cl4 12.7 17.5Cl6 7.0 9.2Cl6:l 0.0 0.0Cl8 1.7 3.0C18:l 14.4 11.5C18:2 2.2 2.2C18:3 trace 0.0c20 0.1 0.0c20: 1 0.0 0.0

-

- -

-10.713.7 -67.1 -0.35.5 -1.2

41.014.4

- 14.7

5.52.0

63.519.5

Fatty acid composition of mahua (M adhuca long-i fo l ia or M. indica), dhupa (Vateria indica) andmango (M angif era indi ca) interesterified with pal-mitate and/or stearate (Sridhar et al ., 1991).Production of a cocoa butter-like fat from theinteresterification of totally hydrogenated cotton-seed and olive oils (Chang et al ., 1990).

CONCLUSION

Cocoa butter is the only continuous fat phase in choco-late and is therefore responsible for the dispersion of theother constituents. Efforts have been made to find analternative to cocoa butter and to replace parts of thecocoa butter in chocolate, for economic and technolo-gical reasons.

A wide variety of plant fats have been investigatedfor their potential as cocoa butter alternatives. Theircompositional data with respect to triglycerides, fattyacid and sterol and other fractions of the unsaponifi-ables are given in this report for the individual analysisof plant fats. Compositional data reflecting typicalranges for the individual fats not included in this revieware comprehensively published elsewhere (citationsgiven).

There is no other naturally occurring fat with thesame physical properties as cocoa butter. It is brittle atroom temperature and is completely and fast melting atbody temperature. Thus, all possible alternatives aremade by blending and/or modifying fats. The major

methods for modification of the fats are fractionatedcrystallisation and interesterification of the fat as well


17/25

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