WO2009078030A1 - Substitut de graisse - Google Patents

Substitut de graisse Download PDF

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Publication number
WO2009078030A1
WO2009078030A1 PCT/IN2008/000107 IN2008000107W WO2009078030A1 WO 2009078030 A1 WO2009078030 A1 WO 2009078030A1 IN 2008000107 W IN2008000107 W IN 2008000107W WO 2009078030 A1 WO2009078030 A1 WO 2009078030A1
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WO
WIPO (PCT)
Prior art keywords
fat
omega
fatty acid
fat substitute
substitute
Prior art date
Application number
PCT/IN2008/000107
Other languages
English (en)
Inventor
Krishnaji Sharad Kasarle
Original Assignee
Alkem Laboratories Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Alkem Laboratories Limited filed Critical Alkem Laboratories Limited
Publication of WO2009078030A1 publication Critical patent/WO2009078030A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
    • C07H13/06—Fatty acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/20—Reducing nutritive value; Dietetic products with reduced nutritive value
    • A23L33/21—Addition of substantially indigestible substances, e.g. dietary fibres

Definitions

  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • olestra 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.
  • 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.
  • 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.
  • a fat substitute comprising an oligosaccharide in conjugation with a fatty acid.
  • 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 ⁇ -cyclodextrins for a period of 6-10 hours at 45°C.
  • composition of a fat substitute further comprising phytoestrogens, natural tocopherols and tocotrienols.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • EFAs There are two families of EFAs: ⁇ -3 (or omega-3 or n-3) and ⁇ -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).
  • ALA alpha linolenic acid
  • LA linoleic acid
  • 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
  • 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).
  • omega-3 fatty acids 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
  • 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.
  • 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:
  • 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.
  • Finished product is treated with activated charcoal and passed through sparkler filter to obtain the final product.
  • the finished product is stable for almost 6 years when stored at normal ambient temperature of 30 0 C.
  • 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 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 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.
  • the above chart shows the heat stability of the fat substitute with increasing temperature during the frying of vegetarian food items.
  • the above chart shows the frying stability of the fat substitute with repeated usage.
  • the above chart shows the heat stability of the fat substitute with increasing temperature during the frying of non - vegetarian food items.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Mycology (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Botany (AREA)
  • Organic Chemistry (AREA)
  • Biochemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • General Health & Medical Sciences (AREA)
  • Biotechnology (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Edible Oils And Fats (AREA)

Abstract

La présente invention concerne un substitut de graisse formé par la conjugaison de fructo-oligosaccharides avec des acides gras oméga. Le substitut de graisse selon la présente invention confère une stabilité thermique à l'acide gras oméga, présente une synergie dans la teneur en acide gras oméga et offre également des avantages pour la santé. La présente invention porte également sur des compositions comprenant le substitut de graisse.
PCT/IN2008/000107 2007-12-17 2008-02-25 Substitut de graisse WO2009078030A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN2472MU2007 2007-12-17
IN2472/MUM/2007 2007-12-17

Publications (1)

Publication Number Publication Date
WO2009078030A1 true WO2009078030A1 (fr) 2009-06-25

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PCT/IN2008/000107 WO2009078030A1 (fr) 2007-12-17 2008-02-25 Substitut de graisse

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160310602A1 (en) * 2013-12-18 2016-10-27 Centro De Investigacion Y Asistencia En Tecnologia Y Diseno Del Estado De Jalisco A.C. Bioconjugate molecules with biological and techno-functional activity, method for the production thereof and use thereof

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD227137A1 (de) * 1984-10-03 1985-09-11 Adw Ddr Verfahren zur herstellung von polyolester-gemischen
US4614718A (en) * 1983-08-23 1986-09-30 Dai-Ichio Kogyo Seiyaku Co., Ltd. Synthesis of sugar or sugar-alcohol fatty acid esters
JPS62263143A (ja) * 1986-05-09 1987-11-16 Kao Corp サイクロデキストリン包接物
EP0268974A2 (fr) * 1986-11-21 1988-06-01 Hoechst Aktiengesellschaft Méthode de préparation de mélanges de mono- et oligomères d'esters de carbohydrates, les mélanges d'esters de carbohydrates ainsi obtenus et leur utilisation
US4973489A (en) * 1987-05-13 1990-11-27 Curtice Burns, Inc. Polysaccaride fatty acid polyester fat substitutes
EP0434119A2 (fr) * 1989-12-21 1991-06-26 Unilever N.V. Procédé pour raffiner le produit brut de production de polyesters de polyols et acides gras, contenant du savon
EP0470452A2 (fr) * 1990-08-09 1992-02-12 Staroil Limited Procédé de préparation de complexes d'acides gras polyinsaturés à longue chaîne avec des cyclodextrines
EP0647652A2 (fr) * 1993-10-05 1995-04-12 Kraft Foods, Inc. Procédé de préparation de polyesters de saccharides par transestérification
US6080853A (en) * 1996-08-08 2000-06-27 The Procter & Gamble Company Polyol polyester synthesis
FR2898817A1 (fr) * 2006-03-23 2007-09-28 Univ Rouen Association de substance oleagineuse avec un melange d'au moins deux cyclodextrines

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4614718A (en) * 1983-08-23 1986-09-30 Dai-Ichio Kogyo Seiyaku Co., Ltd. Synthesis of sugar or sugar-alcohol fatty acid esters
DD227137A1 (de) * 1984-10-03 1985-09-11 Adw Ddr Verfahren zur herstellung von polyolester-gemischen
JPS62263143A (ja) * 1986-05-09 1987-11-16 Kao Corp サイクロデキストリン包接物
EP0268974A2 (fr) * 1986-11-21 1988-06-01 Hoechst Aktiengesellschaft Méthode de préparation de mélanges de mono- et oligomères d'esters de carbohydrates, les mélanges d'esters de carbohydrates ainsi obtenus et leur utilisation
US4973489A (en) * 1987-05-13 1990-11-27 Curtice Burns, Inc. Polysaccaride fatty acid polyester fat substitutes
EP0434119A2 (fr) * 1989-12-21 1991-06-26 Unilever N.V. Procédé pour raffiner le produit brut de production de polyesters de polyols et acides gras, contenant du savon
EP0470452A2 (fr) * 1990-08-09 1992-02-12 Staroil Limited Procédé de préparation de complexes d'acides gras polyinsaturés à longue chaîne avec des cyclodextrines
EP0647652A2 (fr) * 1993-10-05 1995-04-12 Kraft Foods, Inc. Procédé de préparation de polyesters de saccharides par transestérification
US6080853A (en) * 1996-08-08 2000-06-27 The Procter & Gamble Company Polyol polyester synthesis
FR2898817A1 (fr) * 2006-03-23 2007-09-28 Univ Rouen Association de substance oleagineuse avec un melange d'au moins deux cyclodextrines

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160310602A1 (en) * 2013-12-18 2016-10-27 Centro De Investigacion Y Asistencia En Tecnologia Y Diseno Del Estado De Jalisco A.C. Bioconjugate molecules with biological and techno-functional activity, method for the production thereof and use thereof

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