WO2009078030A1

WO2009078030A1 - Fat substitute

Info

Publication number: WO2009078030A1
Application number: PCT/IN2008/000107
Authority: WO
Inventors: Krishnaji Sharad Kasarle
Original assignee: Alkem Laboratories Ltd
Current assignee: Alkem Laboratories Ltd
Priority date: 2007-12-17
Filing date: 2008-02-25
Publication date: 2009-06-25
Anticipated expiration: 2010-06-17

Abstract

The present invention describes a fat substitute formed by the conjugation of fructo-oligosaccharides with omega fatty acids. The fat substitute of the present invention imparts heat stability to the omega fatty acid, shows synergy in the omega fatty acid content and also offers health benefits. The present invention also describes compositions comprising the fat substitute.

Description

FAT SUBSTITUTE FIELD OF INVENTION

The present invention relates to fat substitutes formed by conjugation of oligosaccharides with a fatty acid. More particularly it relates to fat substitutes formed by conjugation of oligosaccharides with omega-3, omega-6 fatty and omega-9 fatty acids. The present invention further relates to fat substitutes that render synergy to the omega fatty acid content and also impart increased heat stability to omega fatty acids.

BACKGROUND OF THE INVENTION

Fats are organic compounds that are made up of carbon, hydrogen, and oxygen. They are a source of energy in foods. Fats belong to a group of substances called lipids. This category of molecules is important for many forms of life, serving both structural and metabolic functions. They are an important part of the diet of most heterotrophs including humans.

Chemically fats are triesters of glycerol and fatty acids. Fats may be either solid or liquid at normal room temperature, depending on their structure and composition. Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water.

Vitamins A, D, E and K are fat-soluble, meaning they can only be digested, absorbed, and transported in conjunction with fats. Fats are sources of essential fatty acids, an important dietary requirement. They are one of the nutrient categories essential for proper growth, development and maintenance of good health. They are an especially important source of calories for people who are underweight and for infants and toddlers, who have the highest energy needs per kilogram of body weight of any age group. Fat also plays important roles in food preparation and consumption. It gives taste, consistency, stability, and palatability to foods.

On the other hand, too much fat intake can be harmful. Fat provides our most concentrated form of energy. Its energy content (9 calorie/gram) is over twice as great as carbohydrates and proteins (4 calorie/gram). Fat intake also is linked to several chronic diseases. There is some evidence of a link between high intake of fat and a possible increased risk of certain cancers, such as breast, colon and prostate cancers. There also is a link between high intake of saturated fat and cholesterol and an increased risk of coronary heart disease. Too much fat also increases the chance of becoming obese.

Reducing dietary fat has thus become a major dietary goal for many consumers. To meet this dietary goal, people need to significantly modify their diets — e.g., choose leaner meats, skin poultry and fish, select low-fat/non-fat dairy products and dressings, and limit fried foods. But consumers' strong desire for high-fat foods makes this difficult. In fact, diet and obesity experts have found that consumers have difficulty maintaining diets once their fat consumption dips below 30 percent of total calories.

The food industry has responded to this consumer demand by offering an ever-increasing variety of low-fat eating choices. These reduced-fat foods are the result of various new, and existing, food technologies used to replace some or most of the fat without sacrificing the taste and texture consumers desire.

Fat substitutes have opened the door for a new generation of reduced-fat foods that have the taste and texture of the high-fat foods consumers enjoy, but without unnecessary calories, cholesterol or fat. The ideal fat substitute thus recreates all the attributes of fat, while also significantly reducing fat and calorie content.

Many of the low-fat products introduced in recent years contain carbohydrate-based fat substitutes e.g., cellulose, maltodextrins, gums, starches, fiber and polydextrose. Carbohydrates have been used safely for many years as thickeners and stabilizers. These ingredients are also effective fat substitutes in many formulated foods, including heat applications but they are not suitable for frying foods. Protein-based fat substitutes have tremendous potential for use in a variety of products, especially frozen and refrigerated products but protein-based fat substitutes too are not suitable for frying foods. Simplese is an example of a protein-based fat substitute. Simplese can be used in many different kinds of food. Some of these foods are: ice cream, yogurt, salad dressing, and mayonnaise. But simplese cannot be used to cook foods since heat causes the protein to turn into a form of gel, thereby destroying its creamy quality.

Scientists have been able to chemically alter fatty acids to provide fewer or no calories, making fat-based fat substitutes possible. Some fat-based fat substitutes actually pass through the body virtually unabsorbed. Olestra is an example of fat based fat substitute. The olestra molecule is larger than a fat molecule, and is therefore not hydrolyzed by the body's digestive enzymes. It does not get absorbed (zero calories) and leads to anal leakage of oil / fat causing discomfort to consumers (oil stained underwear). Intake of olestra also leads to nutritional deficiencies.

Since olestra passes through the gastrointestinal tract without being digested or absorbed and is lipophilic, olestra has the potential to cause gastrointestinal effects, such as abdominal cramping and stool softening or loosening, and to reduce absorption of fat-soluble vitamins and nutrients, which partition into olestra when ingested at the same time. Fats normally bind to the fat-soluble vitamins A, D, E, and K in the intestine, and when the body absorbs the fat, these essential vitamins bind to the absorbed fat. Similarly these vitamins also stick to the fake fat, olestra. Instead of being taken up into the body, they are excreted, unused, with it. An excessive amount of olestra-containing foods in the diet thus makes the body deficient in these important vitamins. Olestra also deprives the body of an important family of nutrients called carotenoids. These red, yellow and orange pigments give fresh fruits and vegetables their color, and they're also found in green leafy vegetables. A lot of evidence suggests that these nutrients protect the body against heart disease, prostate cancer and degeneration of the macula, the part of the eye that lets humans see fine details like newsprint. In clinical studies, people who ate olestra had reduced carotenoid levels in their blood. The idea behind all these fat substitutes is to reduce a food's fat and calories while maintaining the texture provided by fat. However they often fall short; while most contain fewer calories than fat, they don't withstand the cooking temperatures that natural fats do.

US 4696916 discloses an intravenous nutrient which contains a fatty acid ester of carbohydrate and water. The fatty acid ester of carbohydrate disclosed is a long-chain fatty acid ester of oligosaccharide and the long-chain fatty acid is a member selected from the group consisting of oleic acid, linoleic acid, and linolenic acid.

The present invention is a fat substitute offering an additional advantage of heat stability of omega fatty acids.

US 4973489 teaches a fat substitute food composition containing a polysaccharide fatty acid polyester. The said patent discloses that the polysaccharide is a polymer of at least three monosaccharides and has at least four fatty acid ester groups, each fatty acid portion having from 4 to 24 carbon atoms.

The present invention relates to oligosaccharide derivatisation with fatty acids with enhanced heat stability of the omega fatty acids.

Thus there remains a need in the prior art for a fat substitute that recreates all the attributes of fat, while also significantly reducing fat and calorie content, possessing stability at higher temperature and also offering health benefits. There is also a need for a fat substitute which does not interfere with the absorption of fat-soluble nutrients, both vitamins and carotenoids.

The present inventors have surprisingly found that fat substitutes resulting from the conjugation of oligosaccharides with omega 3, omega 6 and omega 9 fatty acids of natural vegetable have properties similar to those of a naturally occurring fat, are stable at higher temperature, exhibit synergy in the content of the constituent omega fatty acids and also effectively facilitate the absorption of omega fatty acids in the body promoting health benefits. The fat substitute of the present invention has properties similar to those of a naturally occurring fat. The present inventors have observed that all the drawbacks of the existing fat substitutes have been overcome by the fat substitute of the present invention. The present inventors have further observed that consumption of products fried / cooked in the fat substitute of the present invention does not cause anal leakage and consumers feel very light, healthy and free from hyperacidity symptoms.

The present inventors have also observed that shelf life of the finished formulation with respect to other edible oils is almost 3 times more under similar storage conditions. The present invention also describes the best absorption of omega components for optimum health benefits such as lowering LDL, increasing HDL cholesterol, lowering triglycerides and improving overall cardiovascular health and central nervous system health.

OBJECT OF THE INVENTION

It is an object of the present invention to provide a fat substitute.

It is another object of the present invention to provide a fat substitute obtained by the conjugation of oligosaccharides with omega fatty acids.

It is another object of the present invention to provide a fat substitute with excellent heat stability.

It is another object of the present invention to provide a fat substitute which imparts increased heat stability to the constituent fatty acids.

It is another object of the present invention to provide a fat substitute which renders synergy to the omega fatty acid content. It is yet another object of the present invention to provide a fat substitute which gets absorbed in the body promoting optimum health benefits.

It is a further object of the present invention to provide heat stable compositions of the fat substitute.

At least one of the preceding objects is met, in whole or in part, by the present invention, in which is provided a fat substitute comprising an oligosaccharide in conjugation with a fatty acid.

SUMMARY OF THE INVENTION

According to one aspect of the present invention there is provided a fat substitute comprising an oligosaccharide in conjugation with a fatty acid.

According to another aspect of the present invention there is provided a process for the synthesis of a fat substitute comprising the step of stirring a mixture of fatty acids and oligosaccharide in the presence of β-cyclodextrins for a period of 6-10 hours at 45°C.

According to yet another aspect of the present invention there is provided a composition of a fat substitute further comprising phytoestrogens, natural tocopherols and tocotrienols.

According to a further aspect of the present invention there is provided a process for the preparation of the composition of the fat substitute comprising the steps of: i. Addition of ascorbyl palmitate, tocopheryl acetate, tocotrienols to the fat substitute of the present invention to obtain the finished product; ii. Treatment of the finished product with activated charcoal and passage through sparkler filter to obtain the final product. DETAILED DESCRIPTION OF THE INVENTION

Awareness of adverse affects of excessive dietary fat intake is virtually universal.

Consequently, health conscious individuals are modifying their dietary habits and eating less fat. Consumer acceptance of any food product depends upon taste- the most important sensory attribute. Although consumers want foods with minimal to no fat or calories, they also want the foods to taste good. Because several foods formulated with fat substitutes do not compare favorably with the flavor of full-fat counterparts, it is difficult for some people to maintain a reduced fat dietary regimen. Food manufacturers continue to search for the elusive "ideal fat substitute" that tastes and functions like conventional fat without the potential adverse health impact.

The present inventors have surprisingly found that the fat substitute of the present invention is an ideal fat substitute that replaces the fat in foods on a one-to-one, gram-for-gram basis, imparts increased stability to the constituent omega fatty acids at higher temperature, shows synergy in the omega fatty acid content and simultaneously promotes health benefits by getting absorbed and not causing vitamin deficiency.

In a preferred embodiment, the fat substitute of the present invention is synthesized by the conjugation of omega 3, 6, 9 fatty acids or mixtures thereof with Fructo oligosaccharide (GF2, GF3, and GF4 Links). GF2 implies one glucose attached to 2 fructose molecules, GF3 implies one glucose attached to 3 fructose molecules. Similarly oligosaccharides of glucose, maltose, galactose, rhamnose can be used for interesterification.

Fats belong to a group of biological substances called lipids. Lipids are biological chemicals that do not dissolve in water. Fats are esters of the tri-alcohol, glycerol. Therefore, fats are commonly called triglycerides. The structural formula of fats is as under:

Fat substitutes are macromolecules that physically and chemically resemble triglycerides and mimic the molecular shape of fat— one molecule of glycerol attached to three molecules of fatty acids.

In the fat substitute of the present invention, the glycerol molecule is replaced with the above oligosaccharides and has 6 to 15 fatty acids attached. MCT - Medium chain triglycerides can also be included in the above link. Medium chain triglycerides form an integral part of the molecule along with Fatty acid molecules.

G F — 2 FATTY ACIDS LINKS

I

G F F - 3 FATTY ACIDS LINKS I

G F F F - 4 FATTY ACIDS LINKS

I

G F F F F - 5 FATTY ACIDS LINKS FREE GLUCOSE - 1 FATTY ACID

UNREACTED SUGAR - 2 to 4 FATTY ACIDS The omega fatty acids come from a variety of vegetable oils, such as soybean, corn, palm, coconut, and cottonseed oils.

Essential fatty acids or EFAs are fatty acids that cannot be constructed within an organism from other components by any known chemical pathways and therefore must be obtained from the diet. There are two families of EFAs: ω-3 (or omega-3 or n-3) and ω-6 (omega-6 or n-6.) Omega-3 and omega-6 fatty acids are very important to our everyday life and function. Omega-3 and omega-6 fatty acids are critical in the structure of our cell membranes and the development of the nervous system and form the foundation for the synthesis of cell mediators (prostaglandins and leukotrienes). These cell mediators play an important role in human physiology and affect coagulation, inflammation and proliferation of certain cells. The two EFA of significance to humans are alpha linolenic acid (ALA) and linoleic acid (LA). There exist other non-essential omega-3 and omega-6 fatty acids, which the body can manufacture from the two essential ones.

• Non-essential omega-3 fatty acids include DHA (docosahexaenoic acid) and EPA

(eicosapentaenoic acid), which the body makes from ALA (the omega-3 essential fatty acid). Infants and children need DHA for proper brain growth. • Non-essential omega-6 fatty acids include AA (arachidonic acid) and GLA (gamma- linolenic acid) which the body makes from LA (the omega-6 essential fatty acid).

Only one of the omega-3 fatty acids is essential (ALA), and a healthy body can make the others (DHA and EPA).

The fat substitute of the present invention which contains large amounts of omega-3 fatty acids and omega-6 fatty acids is capable of functioning as an ideal fat substitute and also releasing essential fatty acids to the diet due to its structural speciality. Without wishing to be bound by any theory, it is thought that with these many fatty acids in the structure of the fat substitute of the present invention, the digestive enzymes cannot get to the saccharide center in the time it takes for the substance to move through the digestive tract, resulting in slow and consistent release of essential fatty acids in blood stream after getting absorbed in liver. The center is where breakdown of the substance for absorption into the body would take place. As a result of getting absorbed, the fat substitute of the present invention is not zero calories. The calorie value of the fat substitute of the present invention is upto 40% lower than normal oils i.e. about 5.4 calories/g

It is a well established fact that omega fatty acids are not stable at high humidity conditions above 60% R.H. and at high temperatures as they get rancid due to oxidation. However the fat substitute of the present invention is stable upto 300°C. The fat substitute of the present invention does not degrade or show lower omega fatty acid contents when used repeatedly for frying foods. Stability and retention of the finished product and the omega fatty acid is excellent at high temperature. The fat substitute of the present invention can be reused upto 20 times repeatedly for frying without any degradation or turning rancid. There are no losses of omega 3, 6, 9 in the said process, the fat substitute of the present invention has no trans fats and does not develop any trans fats in processing and repeated use. The fat substitute of the present invention can be used in bakery products like cakes, pastries, cookies, etc. The fat substitute of the present invention is very stable at all cooking, frying and food processing conditions including retorting, pasteurization and baking.

The fat substitute of the present invention offers nutritional benefits due to the following reasons:

• Contains zero cholesterol, zero transfat

• Helps reducing cholesterol, triglycerides

• Helps prevent atherosclerosis, osteoporosis, inflammatory diseases • Reduces risk of cardiovascular diseases, rheumatoid arthritis, improves functioning of brain, strengthens joints

• Helps in weight loss and stimulates brown fat cells

• Plays an effective role in maternal and foetus health

• Helps in alleviation of allergies • Prevents headaches and migraines

• Safe for diabetic and cardiac patients.

The benefits of omega 3, 6, 9 include all of the benefits of all three types of fatty acid. The amounts and ratios of each fatty acid are balanced to optimal levels of each. Taking an omega 3, 6, 9 supplement is a good way to ensure that the consumer gets essential nutrients for his/her good health. Fructo oligosaccharide is a very strong prebiotic and soluble fiber which improves immunity and cardiovascular health by lowering LDL cholesterol levels naturally, overall the fat substitute of the present invention is healthy as it is composed of FOS, omega fatty acids, phytoestrogens, natural tocopherols and tocotrienols is zero trans fat and cholesterol.

The details of various samples employed for the experimental purpose are as given under: Table 01

EXAMPLES

Example 1

Process for making the fat substitute of the present invention

Mixture of fatty acids (5% to 95%) and oligosaccharide (upto 95%) is treated with B cyclodextrins (Min 2%) and held for 6 hours to 10 hours at 45 °C with constant agitation.

Use of ascorbyl palmitate (50 mg to 200 mg per Litre of finished product), tocopheryl acetate

(10 mg to 80 mg per Litre of finished product) enhances oxidative stability of intermediate complex, which helps the final product to obtain optimum heat stability. Tocotrienols to the level of 10 mg - 50 mg per litre of finished product helps improve cardio protective characteristics.

Finished product is treated with activated charcoal and passed through sparkler filter to obtain the final product.

These additives enhance the stability and performance of the finished product. The finished product is stable for almost 6 years when stored at normal ambient temperature of 30⁰C.

Example 2

It can thus be interpreted from the above chart that the constituent omega acids do not degrade at high temperature which is indicative of the stability of the fat substitute of the present invention at high temperature.

Example 3:

Determination of Fatty acid composition of oils and fats by Gas Liquid Chromatography. This test was conducted in accordance with:

(Ref: IUPAC 2.301, 2.302(1979)/ F.A.O Manuals of Food quality Control 14 /

8, pages 274-281 / A.O.A.C 17^th edn, 2000. Official method 969.33 969.22.

Fatty acids in oils and fats. Preparation of methyl esters / Gas chromatographic method.)

Principle: The methyl esters are formed using boron trifluoride or methanol and alkali and separated by gas - liquid chromatography using a flame ionization detector. The pattern of methyl esters can be compared with authentic oils for identification. Fatty acid composition prior to conjugation with FOS

Example 4

Fatty acid composition after conjugation with FOS

A comparison of the data from Example 3 and Example 4 clearly indicates that the conjugation of omega fatty acids with FOS results in an increase in content of omega fatty acid in the finished product i.e. the fat substitute of the present invention. This aspect highlights the synergy in the omega fatty acid content in the fat substitute.

Example 5

Stability of fatty acids prior to conjugation with FOS

Example 6

Stability of fatty acids after conjugation with FOS

Determination of the oxidative stability of oils and fate bused on the international standard AQCR Cd \2h-92

The comparison of data from Example 5 and Example 6 shows the increased oxidative stability of the omega fatty acid due to conjugation with FOS.

Example 7

Heating with ascending time combinations (Vegetarian food items)

The above chart shows the heat stability of the fat substitute with increasing temperature during the frying of vegetarian food items.

Example 8

Frying stability data with repeated cycles

The above chart shows the frying stability of the fat substitute with repeated usage.

Example 9

Heating with ascending time combinations (TSfon- Vegetarian food items)

The above chart shows the heat stability of the fat substitute with increasing temperature during the frying of non - vegetarian food items.

Claims

1. A fat substitute comprising an oligosaccharide in conjugation with a fatty acid.

2. The fat substitute as claimed in claim 1 wherein the oligosaccharide is an oligosaccharide of fructose, glucose, maltose, galactose, rhamnose.

3. The substitute as claimed in claim 1 wherein the oligosaccharide and fatty acid are present in the ratio 5 : 95 upto 95 : 5.

4. The substitute as claimed in claim 3 wherein the oligosaccharide and fatty acid are preferably selected from the ratio 10: 90, 15 : 85.

5. The fat substitute as claimed in claim 1 wherein the fatty acid is an omega fatty acid.

6. The fat substitute as claimed in claim 5 wherein the omega fatty acid is selected from omega -3- fatty acid, omega -6- fatty acid, omega -9- fatty acid or combinations thereof.

7. The fat substitute as claimed in claims 1 to 6 that imparts heat stability to the omega fatty acids in the temperature range 30⁰C to 300°C.

8. The fat substitute as claimed in claims 1 to 7 that shows synergy in the omega fatty acid content.

9. A process for the synthesis of a fat substitute comprising the step of stirring a mixture of fatty acids and oligosaccharide in the presence of β-cyclodextrins for a period of 6- 10 hours at 45°C.

10. The composition of the fat substitute as claimed in claim 1 further comprising phytoestrogens, natural tocopherols and tocotrienols.

11. The process for the preparation of the composition of the fat substitute as claimed in claim 10 comprising the steps of: i. Addition of ascorbyl palmitate, tocopheryl acetate, tocotrienols to the fat substitute to obtain the finished product; ii. Treatment of the finished product with activated charcoal and passage through sparkler filter to obtain the final product.