AU2005232369A1 - Water continuous product comprising sterol or stanolester and a tocopherol - Google Patents

Description

WO2005/099484 PCT/EP2005/002878 1 Water continuous product comprising sterol or stanolester and a tocopherol Field of the invention 5 The invention relates to water continuous products such as milk and yoghurt comprising a sterol or stanol fatty acid ester and an antioxidant comprising tocopherol. 10 Background to the invention Food products for lowering cholesterol levels in blood are known for several years. Commercial products that contain ingredients that influence blood cholesterol lowering when 15 daily consumed are for example Becel pro.activ TM and Benecol

TM

. Examples of the ingredients on which the cholesterol lowering effect is based are sterol fatty acid ester and stanol fatty acid ester. These were initially included in products rich in fat such as margarine. One of the reasons for this was that 20 their incorporation in low fat products was considered difficult. WO-A-99/44442 relates to stable, homogeneous, emulsifier free suspensions of sterol compounds. 25 EP-A-1212945 discloses dairy-based beverages fortified with stanolester for cholesterol lowering. The amount of stanolester is from 0.2 to about 2 wt%. Although the products according to EP-A-1212945 may provide 30 suitable short term stability we have found that such water continuous products comprising sterol or stanol fatty acid esters may suffer from off taste development on storage over times of several weeks.

WO2005/099484 PCT/EP2005/002878 2 In view of the product segment being products with a health claim the route to solving this problem should be one which is acceptable from a health perspective and is not leading to 5 objections with respect to addition of chemicals with poor health image. We have surprisingly found that the use of tocopherol wherein the amount of y- or 5- tocopherol is at least 60 wt% of the 10 total weight of tocopherol, leads to surprisingly good products which do not suffer so much from the development of off taste. Products comprising tocopherol and sterol or stanol are already known in the art. 15 WO-A-02/07235 discloses anti-inflammatory compositions comprising sterols and tocotrienols or polyphenols. The preferred tocotrienols are alpha, beta, gamma and delta tocotrienols. 20 WO-A-02/060272 discloses edible oils comprising at least one of free sterol or steryl ester and preferably a compound that reduces cholesterol synthesis in a human patient, such as at least one tocotrienol. 25 WO-A-99/25361 discloses hypocholesteroaemic preparations comprising stenolester and preferably a tocopherol. The most preferred tocopherol is alpha-tocopherol. 30 Summary of the invention The invention relates to a water continuous product comprising up to 10 wt% fat, a sterol and/or stanol fatty acid ester, and WO2005/099484 PCT/EP2005/002878 3 a tocopherol comprising gamma and/or delta tocopherol , wherein the amount of y-, 0- tocopherol is at least 60wt% of the total amount of tocopherol. 5 Detailed description of the invention In the context of this specification and claims all percentage is a weight percentage on total product weight. 10 The invention relates to water continuous products. This means that the products comprise a continuous aqueous phase in which other ingredients may be present. For example these other ingredients are dissolved, dispersed or emulsified in the aqueous phase. This is contrary to fat continuous products 15 wherein the continuous phase is formed by the fat phase such as in butter or margarine. In these products the dispersed phase is water in the form of droplets emulsified in the fat phase. The products according to the invention comprise a sterol 20 and/or stanol fatty acid ester. Sterols or phytosterols, also known as plant sterols or vegetable sterols can be classified in three groups, 4-desmethylsterols, 4-monomethylsterols and 25 4,4'-dimethylsterols. In oils they mainly exist as free sterols and sterol esters of fatty acids although sterol glucosides and acylated sterol glucosides are also present. There are three major phytosterols namely beta-sitosterol, stigmasterol and campesterol. Schematic drawings of the components meant are as 30 given in "Influence of Processing on Sterols of Edible Vegetable Oils", S.P. Kochhar; Prog. Lipid Res. 22: pp. 161 188.

WO2005/099484 PCT/EP2005/002878 4 The respective 5 alpha- saturated derivatives such as sitostanol, campestanol and ergostanol and their derivatives are in this specification referred to as stanols. 5 Preferably the esterified sterol or stanol is selected from the group comprising fatty acid ester of 13-sitosterol, p sitostanol, campesterol, campestanol, stigmasterol, brassicasterol, brassicastanol or a mixture thereof. 10 The sterols or stanols are esterified with a fatty acid. Preferably the sterols or stanols are esterified with one or more C 2

-

22 fatty acids. For the purpose of the invention the term C2- 22 fatty acid refers to any molecule comprising a C 2

-

22 15 main chain and at least one acid group. Although not preferred within the present context the C 2

-

22 main chain may be partially substituted or side chains may be present. Preferably, however the C 2

-

22 fatty acids are linear molecules comprising one or two acid group(s) as end group(s). Most preferred are linear C8- 22 20 fatty acids as these occur in natural oils. Suitable examples of any such fatty acids are acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, capric acid. Other suitable acids are for example citric acid, 25 lactic acid, oxalic acid and maleic acid. Most preferred are myristic acid, lauric acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid, cetoleic acid, erucic acid, elaidic acid, linoleic acid and linolenic acid. 30 When desired a mixture of fatty acids may be used for esterification of the sterols or stanols. For example, it is possible to use a naturally occurring fat or oil as a source of WO2005/099484 PCT/EP2005/002878 5 the fatty acid and to carry out the esterification via an interesterification reaction. In a preferred embodiment, the fatty acid in the esterified 5 sterol or stanol is derived from sunflower oil, rapeseed oil, safflower oil, coconut oil, or a mixture thereof. Most preferred the fatty acid in the esterified sterol or stanol is derived from sunflower oil. 10 Optionally the products comprise a combination of a sterol fatty acid ester and a stanol fatty acid ester. Optionally the products comprise unesterified "free", sterol or 15 stanol in addition to the esterified sterol or stanol. The total amount of sterol and stanol fatty acid ester is preferably from 0.1 to 10 wt%. More preferred, the amount is from 0.5 to 5 wt%, most preferred from 2 to 5 wt% on total 20 product weight. The products comprise a tocopherol. Preferably the tocopherol is selected from the group comprising a-, p-, y-, 5 tocopherol. 25 Tocopherols are derivatives of 2-methyl-6-chromanol with an attachment of a saturated 16-carbon isoprenoid chain at C-2. The structures of a-, 1-, y-, and 5- tocopherol are presented in figure 1. The level of tocopherol in a product may be 30 obtained by routine measures including extraction of tocopherols from the samples, followed by quantification using

HPLC.

WO2005/099484 PCT/EP2005/002878 6 Tocopherols are naturally present in oil seeds, grains, leaves, and other green parts of higher plants. Suitable sources of tocopherol are e.g. soy bean and corn oil. 5 Of all tocopherol present in the product, at least 60 wt%, preferably at least 70 wt%, more preferred at least 80 wt%, even more preferred at least 94 wt% is in the form of y-, 5 tocopherol. This means that the total amount of y-, 5 10 tocopherol is at least 60 wt% on the total weight of tocopherol. It was found that products comprising sterol or stanol ester, especially those of sunflower oil, showed highly improved taste stability and less development of off flavour when using this specific tocopherol composition. 15 More preferred from 60 to 99wt%, more preferred from 60 to 95 wt%, even more preferred 70 to 95 wt% of the tocopherol present in the product is y-tocopherol and 5- tocopherol. 20 More preferred, the tocopherol comprises at least GO60wt% y tocopherol, even more preferred from 60 to 95 wt% y-tocopherol. The total amount of tocopherol to achieve the desired level of off taste reduction is preferably from 10 to 50.000 ppm, more 25 preferred from 10 to 5000 ppm, more preferred from 10 to 1000 ppm, even more preferred from 10 to 500 ppm, most preferred from 50 to 500 ppm on total product. The products according to the invention comprise up to 10% fat. 30 This implies that the products may also be fat free. Preferred products are selected from the group comprising drinks such as milk or yoghurt drinks, yoghurts, creams, liquid products based on fruit and protein, such as fusion drinks.

WO2005/099484 PCT/EP2005/002878 7 The fat may be of any origin. Suitable fats therefore include vegetable fat such as sunflower oil, rapeseed oil, olive oil, coconut oil, safflower oil and dairy fat. Preferred products 5 comprise dairy fat, preferably in an amount from 20 to 80 wt% on total fat. Most preferred products comprise a combination of dairy fat and vegetable fat. The dairy fat may be added as such or may be part of any of the ingredients that are included in the product such as milk proteins or cream. 10 Optionally the products comprise further ingredients such as thickeners, emulsifier, sugar, protein, taste and flavour modifiers, fruit or fruit concentrate, acidifier, cultures. 15 Preferably the products comprise protein, preferably in an amount of from 0.5 to 10 wt%. The most preferred protein is milk protein such as derived from fresh milk, yoghurt, quark, skimmed milk powder, whey powder, caseinate, cream. An alternative protein source is vegetable protein, preferably soy 20 protein. Preferred products comprise a living culture. In this context a living culture is a culture which has not been inactivated by a heating step and which continues fermentation in pack. Such 25 cultures are also referred to as yoghurt cultures and probiotics. Suitable cultures include Lactobacillus Bulgaricus, Lactobacillus rhamnosus, Streptococcus thermopilus, Bifidobacterium, Lactobacillus casei. It was found that such cultures may also positively contribute to off taste reduction. 30 Most preferred the products are concentrated drinks comprising up to 5 wt% fat, from 1.5 to 4 wt% sterol and/or stanol fatty WO2005/099484 PCT/EP2005/002878 8 acid ester, milk protein, water and sugar or a sugar replacer (sugar being preferred) and preferably emulsifier. Even more preferred those products are acidified, preferably 5 fermented products, with a pH in the range from 3.8 to 6, preferably from 4 to 5. The products may be prepared by any suitable process. A preferred process comprises the steps of preparing a premix of 10 the tocopherol and the sterol and/or stanol fatty acid ester. This premix is added to the aqueous phase. The other ingredients may be added at any stage of the process. In the process it is preferred that all ingredients are mixed, 15 subjected to pasteurizing, homogenizing and cooling. For acidified products it is preferred to include a fermentation step which is followed by homogenizing and cold filling to preserve probiotics activity. 20 The invention is illustrated by the following non-limiting examples. Example 1, 2 25 A yoghurt was prepared with the product composition in wt% on total product as presented in table 1.

WO2005/099484 PCT/EP2005/002878 9 Table 1: product composition Ingredient Example 1 Wt% Example 2 Wt% Skimmed milk 72 72 cream (40% fat) 3.8 3.8 Skim milk powder 0.5 0.5 sugar (sucrose) 8.00 8.00 d-tocopherol 200 ppm 0 y-tocopherol 0.00 800 ppm Sitosterolester of 3 3 sunflower oil water Up to 99.8wt% Up to 99.8 wt% total base 99.80 99.80 pre-culture 0.20 0.20 total yoghurt 100.00 100.00 Specification of tocopherols: 5 y-tocopherol was derived from a tocopherol mixture comprising 60% y-tocopherol and 24% B-tocopherol. The 5-tocopherol was derived from a tocopherol mixture comprising 86% 6-tocopherol. 10 Process A premix was prepared comprising milk, cream and water at a temperature of about 60 oC. Tocopherols and sterolester was 15 weighed and mixed with a spoon. The aqueous mixture was subjected to vigorous stirring in a Turrax

TM

. While the Turrax T, was run at low speed of about 3500 rpm, the powder mix of sugar and skim milk powder was mixed in, followed by the sterolester composition. Mixing was continued at higher speed for some more 20 minutes. The mixture was then heated to 75 oC and pasteurised. Next the mix was homogenised at 200 bar and cooled to fermentation temperature of about 43 OC.

WO2005/099484 PCT/EP2005/002878 10 A separately prepared yoghurt culture was used to inoculate the product. Fermentation was continued until a pH of about 4.3 was reached. The fermented product was sturred and homogenised at about 50 bar before it was filled into sterile containers. The 5 product was cooled and stored at 5 OC. Tasting of the products and identification of off flavour: A trained panel of experts evaluated the products directly 10 after preparation and after storage for 3 weeks at 5 OC. The panel was trained on tasting off flavor and compared the products to a commercially available drink yoghurt of the brand Actimel

TM

, which is free of sterol or stanol ester. The products were scored as good, acceptable or bad. 15 As a comparison example products were made with the composition of example 1 and 2 except that the tocopherols were not included. This example is referred to as "C". 20 Comparative example "C" was evaluated as bad by all participants for the sample directly after preparation and after 3 weeks of storage. Product according to example 1 was evaluated as good by 25% of 25 the test panel and acceptable by 50% of the test panel directly after preparation. It was found good by about 33% of the test panel and acceptable by about 35% of the test panel after 3 weeks. Product of example 2 was evaluated as good by 38% of the panel and acceptable by 40% of the panel directly after 30 preparation. After 3 weeks 50% of the panel found it good and 50% acceptable.

WO 2005/099484 PCT/EP2005/002878 11 These results show that the addition of 5-tocopherol or tocopherol results in reduced off taste in water continuous products comprising a fatty acid ester of sunflower oil and beta sitosterol. 5 10 15 20

Claims (10)

1. Water continuous product comprising up to 10 wt% fat, a sterol fatty acid ester and/or stanol fatty acid ester, and a tocopherol comprising y-, and/or 5- tocopherol, characterized in that the amount of y-, 6- tocopherol is at least 60wt% of the total amount of tocopherol.

2. Water continuous product according to claim 1 wherein the product comprises tocopherol, which is characterized in that the tocopherol comprises at least 70wt% y-tocopherol and 5 tocopherol.

3. Water continuous product according to claim 2 wherein the tocopherol comprises at least 60wt% y-tocopherol.

4. Water continuous product according to any of claims 1-3 wherein the fatty acid part of the sterol or stanol fatty acid esters is selected from the group of fatty acids comprising those derived from sunflower oil, rapeseed oil, safflower oil, coconut oil, or a mixture thereof.

5. Water continuous product according to claim 4 wherein the fatty acid part is derived from sunflower oil.

6. Water continuous products according to any of claims 1-5 comprising a living culture.

7.Water continuous product according to any of claims 1-6 wherein the fat comprises a combination of vegetable fat and dairy fat. WO 2005/099484 PCT/EP2005/002878 13

8. Water continuous product according to any of claims 1-7 wherein the total amount of sterol fatty acid ester and stanol fatty acid ester is from 1 to 10 wt% on total product weight.

9. Water continuous product according to any of claims 1-8 wherein the amount of tocopherol is in total from 10 to 5000 ppm.

10. Concentrated drink comprising up to 5 wt% fat, from 1.5 to 4 wt% sterol fatty acid ester and/or stanol fatty acid ester, milk protein, water and sugar or a sugar replacer and further comprising a tocopherol comprising y-, and/or 5 tocopherol, characterized in that the amount of y-, 5 tocopherol is at least 60wt% of the total amount of tocopherol. WO 2005/099484 PCT/EP2005/002878 1/1 R1 Fig.1. HO 5 4 86 53 CH3 CH 3 CH 3 7 2 R 2 8 H 4 8 CH 3 1 CH 3 R3 locopherol Trivial name R1 R1 R3 a-tocopherol CH 3 CH 3 CH 3 P-tocopherol CH 3 H CH 3 y-tocopherol H CH 3 CH 3 8-tocopherol H H CH 3