WO1993015612A1

WO1993015612A1 - Reduced calorie fats

Info

Publication number: WO1993015612A1
Application number: PCT/EP1993/000222
Authority: WO
Inventors: Frederick William Cain; Deryck Josef Cebula; Nanneke Joke De Fouw
Original assignee: Unilever N.V.; Unilever Plc
Priority date: 1992-02-07
Filing date: 1993-02-01
Publication date: 1993-08-19
Also published as: AU3452493A; CA2129631A1; GB9202665D0; ZA93809B; EP0625009A1

Abstract

A fat composition comprising 5-100 % by weight of a long chain fatty acid triglyceride material of formula (I) or (II) wherein R1 is a C¿20-24? fatty acid and R?2¿ is a C¿12? fatty acid. Preferably the fat compositions are used in food-products, especially in chocolate confectionery products.

Description

Reduced calorie fats

The present invention relates to reduced calorie fats, in particular triglyceride materials containing long chain fatty acids, preferably in combination with medium chain fatty acids. In particular the present invention relates to the use of triglyceride materials containing long chain fatty acids in food-products, especially confectionery products.

Triglyceride fats made with long chain fatty acids are reduced in calories, because the long chain fatty acids are poorly digested by the body.

Several documents describe the use of long chain fatty acids in triglycerides for obtaining a calorie reduction:

WO 91/09537 (P&G) relates to fat and sugar containing food products, wherein the sugar contains a 5-C-hydroxymethyl hexose or derivative thereof and the fat contains a triglyceride with medium long fatty acid chains and long fatty acid chains. Preferred exemplified medium chain fatty acids are mixtures of C₈ and C₁₀ fatty acids, the preferred exemplified long chain fatty acid is Behenic acid.

WO 91/09099 (P&G) describes a process for selectively making triglycerides comprising two medium chain fatty acids and one long chain fatty acid, wherein a monoglyceride of a C₁₈_₂ fatty acid is reacted with a C₈_₁₀ fatty acid at a temperature of 140 to 250°C in the absence of a catalyst under the continuous removal of water. The preferred exemplified long chain fatty acid is Behenic acid, preferred medium chain fatty acids are mixtures of C₈ and C -ι_ηo-

WO 91/09098 (P&G) describes a process for selectively making triglycerides comprising two medium chain fatty acids and one long chain fatty acid, wherein a monoglyceride of a C₁₈_₂ fatty acid is reacted with a C₈_₁₀ anhydride at a temperature of 90 to 190°C in the absence of a catalyst. The preferred exemplified long chain fatty acid is Behenic acid, preferred medium chain fatty acids are mixtures of C₈ and C₁₀.

US 5,023,106 (P&G) describes a flavoured confectionery product comprising triglycerides with medium and long chain saturated fatty acids, wherein the medium chain fatty acid material is a mixture of Caprylic and Capric acid in a ratio of 4 to 1 to 1 to 4 and the long chain saturated fatty acid is behenic acid. Also described is a process for preparing a flavoured confectionery product containing these materials. Similar confectionery products and processes for producing these are describes in US 4,888,196 (P&G) and EP 390 408.

US 4,863,753 (P&G) discloses a reduced calorie peanut butter comprising a dispersion of finely divided peanut particles in a continuous oil phase, wherein the oil phase comprises medium chain triglycerides. Preferred medium chain fatty acids are C₆ to C₁₀ saturated fatty acids which are used in combination with C₁₇ to C₂₆ unsaturated fatty acids.

US 3,595,673 (P&G) relates to high melting hard butter materials consisting essentially of randomly esterified triglycerides with high levels of C₁₂ saturated fatty acids in combination with C₁₆_₁₈ saturated fatty acids and no or low levels of C_Q_₁₀ , C₁₄ and C₂₀ and higher fatty acids.

US 3,353,964 (P&G) relates to corandomized triglycerides containing saturated C₆_₁₄ fatty acids and from 0.3 to 5% of ₂₀_₂₂ fatty acids, wherein the ratio between short chain fatty acids and long chain fatty acids is from 100 to 1 to 1 to 1 .

EP 422 490 (P&G) relates to unit dosage amounts of triglycerides for absorption of cholesterol containing from 1-10 grams of a triglyceride fat containing high levels of ^c ₂₀-₂₄ saturated fatty acids. Exemplified preferred reduced calorie triglycerides comprise Behenic acid as the long chain fatty acid and C₈ and C₁₀ mixtures as the remaining fatty acids.

EP 322,027 (P&G) relates to reduced calorie fats made from triglycerides containing medium and long chain saturated fatty acids. The exemplified preferred long chain saturated fatty acid is behenic acid. Preferred exemplified medium chain saturated acids are mixtures of caprylic and capric acid. This document also provides a listing of theoretically possible triglycerides containing mixtures of medium and long chain saturated fatty acids.

EP 311 167 (P&G) relates to reduced calorie fats with improved auto-ignition properties, said fats comprising medium and long chain saturated fatty acids in combination with long chain unsaturated fatty acids. The exemplified preferred long chain saturated fatty acid is stearic acid, preferred long chain unsaturated fatty acid are linoleic acid, oleic acid and linolenic acid. The preferred exemplified medium chain saturated fatty acid is caprylic acid.

EP 216 419 (P&G) relates to nutritional fats consisting essentially of triglycerides comprising at the 2-position a fatty acid which is either a saturated fatty acid group, or oleoyl or linolenoyl and at the 1- and 3-positions a group selected from n-heptonoyl, n-octanoyl, N-nonanoyl, n- decanonyl and n-undecanoyl. The overall picture emerging from the above mentioned prior art is therefore a preference for combinations of behenic acid and mixtures of C₈ and C₁₀ fatty acids.

The present invention aims at providing novel triglyceride materials comprising a mixture of long chain fatty acids in combination with shorter fatty acids. It is believed that fat compositions of the present invention are advantageous for one or more of the following reasons:

(a) when used in confectionery compositions, especially in chocolate type confectionery products they provide a better melting profile and hardness resulting in a better mouthfeel;

(b) the fat compositions of the invention contain fatty acid chains which are favourable as far as their effect on heart health is concerned;

(c) fat compositions of the invention are easy to manufacture and to process and are stable upon storage;

(d) when fat compositions of the invention are used in flavoured food products they provide an enhanced flavour release;

(e) when fat compositions of the invention are used in chocolate type confectionary products they provide better tempering properties and/or reduced blooming upon storage;

(f) fat compositions of the invention show enhanced crystallisation properties.

Surprisingly it has been found that one or more of the above mentioned or other advantages can be obtained if specific triglycerides are used which comprise high levels of C₂₀-C₂₄ fatty acids, preferably in combination with C₁₂ fatty acids.

Accordingly the present invention relates to a fatty composition comprising 5-100% of a triglyceride material of the formula:

H H H or H H H i i i i l l I I I I I I

H - C - C - C - H H - C - C - C - H

I I I 1 1 1

I I I I I I

0 0 0 0 0 0

I I I I I I

I I I I I I R¹ R² R² R² R¹ R²

wherein R¹ is a C₂₀_₂₄ fatty acid and R² is a C₁₂ fatty acid; preferably R¹ and R² are saturated fatty acid materials. Also preferable R¹ is a C₂₀ fatty acid.

For reference purposes the specific triglyceride materials as defined hereabove will be referred to as long cha-±rr ^~~~ fatty acid triglycerides.

Fat compositions of the invention consist of at least 5% by weight of long chain fatty acid triglycerides, the balance of the fat composition being made up of other fatty materials. However, although fat-compositions of the invention may comprise in addition to the long chain fatty acid triglyceride, optionally up to 95 wt% of further fat components such as other triglyceride materials and lipid fat replacers such as polyol fatty acid esters and jojoba oil, it is preferred that for use in e.g. chocolate products the weight ratio of these fat-components to the long chain fatty acid triglyceride is less than 2 : 1, more preferred less than 1 : 1 or even less than 0.5: 1. In a first preferred embodiment of the invention the fat- compositions contain long chain fatty acid triglycerides substantially in the absence of other fat components.

5 In another preferred embodiment of the invention e.g. when the long chain fatty acid triglycerides are used as hardstocks in margarines or other spreads, it is preferred that the ratio of long chain fatty acid triglycerides to other fat components is between 1:19 and 1:1, more 0 preferred 1:12 and 1:3.

Triglyceride materials other than the long chain fatty acid triglyceride materials may be triglyceride oils or fats of animal or vegetable origin. Suitable conventional 5 triglyceride fats and oils include, optionally partially or fully hydrogenated, coconut oil, palmkernel oil, palm oil,

____marjLne oils, lard, tallow fat, butter fat, cocoa butter fat, soybean oil, safflower oil, cotton seed oil, rapeseed oil, corn oil sunflower oil and mixtures thereof. 0

If mixtures of triglyceride materials are present these can generally be detected as such by techniques like GC , HPLC, DSC etc.

5 Fat-compositions of the invention are preferably used in food-products, for example at levels of 1-100%, more preferred 5-80%, most preferred 10-60%.

The present invention is not specific to edible fat- 0 containing compositions in any particular food area. It may be suitably be applied to food products such as spreads, margarines, creams, shortenings, bakery products such as doughs, cakes and biscuits, fried and snack products, fresh, hard and processed cheeses, meat emulsions, 5 mayonnaise and dressings, confectionery products, such as desserts, fillings, chocolates, candies, chews, and ice¬ creams. In a particular preferred embodiment of the invention the long chain fatty acid triglycerides of the invention are used in confectionery products, especially in chocolate type confectionary products. In another preferred embodiment the food-product is a spread.

Preferred confectionery products in accordance to the invention preferably comprise from 25-70% by weight of the fat composition as defined hereabove, 0.001 to 60% by weight of sugar or other sweeteners such as for example aspartame, 5-45% by weight of cocoa powder or chocolate liquor and 0-20% of milk solids, 0-5% flavouring and/or colouring materials, 0-5% lecithin or other emulsifying agents and up to 100% of other suitable materials like carbohydrate or other bulking agents.

Fat compositions for use in chocolate confectionery products, preferably comprise in addition to the long chain fatty acid triglyceride material as defined above 0-50% by weight of cocoa butterfat, more preferably 5-40%.

Although applicants do by no means want to be bound by any theory it is believed that the use of the above defined long chain fatty acid triglyceride materials in chocolate confectionery products is especially advantageous because of the enhanced crystallisation properties of the resulting chocolate. In particular it is believed that the crystallisation process of chocolates containing long chain fatty acid triglycerides according to the invention is faster and/or the melting properties are better than of other triglyceride materials containing C₂₀_₂ fatty acid chains.

Especially preferred fat compositions for use in chocolate confectionary products are solid at ambient temperature

(20°C) and fluid and soft at mouth temperature (35°C) . For combining these two properties a steep melting profile between 20 °C and 35 °C, especially between 30°C and 35°C is important.

In another preferred embodiment of the invention the chocolate confectionary product of the invention comprises a fat composition substances having an N-value at 20°C of at least 60, more preferred 70-100, most preferred 80-95 and an N-value at 35 °C of less than 15, more preferred from 0-8 , most preferred from 0-3.

The N-value is conveniently measured by nuclear magnetic relaxation technique and is a direct measure of the level of solid fat content at the relevant temperature. This method is suitable described in Fette, Seifen,

Anstrichmittel 80(5) , 180-186, (1978) . To some extent the measurement is dependent on the temperature profile used to prepare the samples for the NMR- easurement. For the purpose of the present invention the following preparatory temperature profile is adopted: 30 minutes at 60°C, 90 minutes at 0°C, 40 hours at 26°C, again 90 minutes at 0°C and finally 60 minutes at the temperature of the measurement, after which the NMR measurement is carried out.

Preferred spread products of the invention are oil and water emulsions which comprise from 5-95% more preferred 10-90, most preferred 60-90% by weight of the fat composition, the balance of the composition being water and optionally other ingredients like emulsifiers, gelling agents, flavouring, colouring materials, preservatives, etc.

Long chain fatty acid triglycerides of the invention may be prepared by any suitable technique for preparing triglyceride materials. A suitable technique may for example include the random esterification of a 1:2 molar mixture of long chain fatty acids and medium chain fatty acids.

Food products of the invention can be prepared by any suitable technique. Chocolate confectionery products may for example be made as described in US 4,810,516. preferably the cooling regime applied to the chocolate is such that the product can be demoulded within 30 minutes after moulding.

The invention will further be illustrated by means of the following examples.

Example I

A chocolate product was prepared with the following formulation:

In redient wt

The following fat-compositions are used:

A: 100% of a triglyceride with 2 C₁₂ fatty acids and 1 C₂₀ fatty acid.

B: 85 wt% of a triglyceride with 2 C₁₂ fatty acids and 1 C₂₀ fatty acid and 15 wt% of cocoa butter (added in addition to the cocoa butter which was inherently present in the cocoa powder) .

C: 100% of a triglyceride with 2 C₈ fatty acids and 1 C₂₂ fatty acid.

D: 85 wt% of a triglyceride with 2 C₈ fatty acids and 1 C₂₂ fatty acid and 15 wt% of cocoa butter (added in addition to the cocoa butter which was inherently present in the cocoa powder) .

Example A and B are in accordance to the present invention, while examples C and D are included for reference purposes. Products A and B are generally of better quality than products C and D (melting behaviour, crystallisation behaviour etc) . Example II

A fat composition A was made of 87 wt% non hydrogenated sunflower oil and 13 wt% of a long chain fatty acid triglyceride with 1 C₂₀ and two C₁₂ saturated fatty acids.

A reference fat composition B was made of 87 wt% non hydrogenated sunflower oil and 13 wt% of a 50:50 (wt) mixture of coesterified Palm kernel oil (hardened to a slip melting point of 38°C) and Palm oil (hardened to a slip melting point of 58°C) .

A third fat composition C was made of the same composition as A, except that there was included 13% of a triglyceride prepared by random esterification of a 2:1 molar mixture of C₁₂ and C₂₀ saturated fatty acids.

Compositions A-C can be used as frying compositions. Compositions A and C are preferred over composition B (reference) .

Compositions A-C can be used for the preparation of a healthy margarine of the composition:

Ingredient parts by weight fat composition 80 water 20 monoglyceride (from Palm oil 58°C) 0.1 colouring/flavouring/ preservatives 0.1

Standard votator line processing may be used to prepare this product. Generally, products with fat compositions A and C are preferred for their oral melting properties to products with fat composition B.

Example III

A fat composition A (reference) was made of 40 wt% of a non hydrogenated soybean oil and 60 wt% of Palm oil hardened to a slip melting point of about 43°C.

A fat composition B is made of 40 wt% of a non hydrogenated soybean oil, 30 wt% of palm oil hardened to a slip melting point of about 43 °C and 30 wt% a long chain triglyceride with one C₂₀ and two C₁₂ saturated fatty acids.

A fat composition C is made of 40 wt% of a non hydrogenated soybean oil and 60 wt% of a long chain triglyceride with one C₂₀ and two C₁₂ saturated fatty acids.

A fat composition D is made of 40 wt% of a non hydrogenated soybean oil, 30 wt% of Palm oil hardened to a slip melting point of about 43 °C and 30 wt% of a triglyceride obtained by the random esterification of a 2:1 molar mixture of C₁₂ and C₂₀ saturated fatty acids.

Fat compositions A-D are used for preparing a bakery margarine of 82 wt% of the fat composition, 1% NaCl, 0.15% monoglyceride (from Palm oil 58°C) , the balance water.

Vol-au-vents are prepared from a dough of 1000 wt parts flour (Banket extra ex Meneba) , 800 weight parts of bakery margarine and 560 weight parts water by preparing a predough of water and flour and folding in the bakery margarine at 20°C (6 half turns in three) . Generally, the fat compositions B-D are preferred over fat composition A, because of handleability of the fat composition (especially for D) and quality of the final product.

to Caprenin a commercially available C₈/C₁₀/C₂₂ triglyceride. Fat A was a C₁₂/C₁₀/C₂₂ triglyceride, fat B was a randomized C₂₀(C₁₂)₂ triglyceride. The fats had the following carbon number profile:

Chocolates of the following composition were prepared:

The chocolates (1) were manufactured by mixing all dry ingredients with the fat and the lecithin in a ball mill at 60°C for 5.5. hours. The other chocolates (2) were made by adding extra cocoa butter to the chocolates 1.

The chocolates were formed into bars by melting the solid chocolate at 52°C in a batch tempering kettle followed by depositing 50 g portions into polycarbonate chocolate moulds (4x3 squares) . The mould temperature was 20°C. The moulds were placed at the centre section of a cooling tunnel, the temperature of the tunnel was set at 15°C, 10°C and 15°C. the moulds were removed from the cooling tunnel and turned upside down.

The de-moulding performance of the chocolate bars was determined by measuring the time between turning upside down and de-moulding of the bars. For the chocolates according to the invention the de-moulding time was 20 minutes or less. For the Caprenin 1 chocolate no chocolate bars were de-moulded after 255 minutes, for the Caprenin 2 chocolates only a few bars (of the 12) were demoulded after 255 minutes.

The gloss and bloom performance of the chocolate bars were also evaluated after storage of 20°C. The following scores were used:

The following results were obtained:

I

The above results clearly shov; that chocolates according to the inventor were of better quality than chocolates with Caprenin.

Claims

1. A fat composition comprising 5-100% by weight of a long chain fatty acid triglyceride material of the formula:

H H H or H H H

I I I I I I

H - C - C - C - H H - C - C - C - H

I I I I I I

0 0 0 0 0 0

I I I I I I

R¹ R² R² R² R¹ R²

wherein R¹ is a C₂₀_₂₄ fatty acid and R² is a C₁₂ fatty acid.

2. A fat composition in accordance to claim 1, wherein R¹ and R² are saturated fatty acids.

3. A fat composition according to claim 1 or 2 , wherein R¹ is a C₂₀ fatty acid.

4. A fat composition according to claims 1-3, wherein the weight ratio between long chain fatty acid materials and other fatty materials is more than 1 : 1.

5. Food product comprising 1-100% by weight of a fat- composition in accordance to claims 1-4.

6. Food product according to claim 5, being a chocolate confectionery product comprising:

(A) 25-70 wt% by weight of a fat composition according to claim 1;

(B) 0.001 to 60 wt% by weight of sugar or other sweeteners;

(C) 5-45 wt% by weight of cocoa powder or chocolate liquor;

(D) 0-20 wt% of milk solids;

(E) 0-5 wt% flavouring and/or colouring materials;

(F) 0-5 wt% emulsifying agents.

7. Food product according to claim 6 having an N₂₀ of at least 60 and N₃₅ less than 15.

8. Food product according to claim 6 or 7 , wherein the fat composition comprises 5-50% of cocoa butter.

9. Food product according to claim 5, being a spread comprising an oil and water emulsion comprising from 5-95% by weight of a fat composition according to claim 1.