CA2448095A1 - A reduced calorie fat - Google Patents
A reduced calorie fat Download PDFInfo
- Publication number
- CA2448095A1 CA2448095A1 CA002448095A CA2448095A CA2448095A1 CA 2448095 A1 CA2448095 A1 CA 2448095A1 CA 002448095 A CA002448095 A CA 002448095A CA 2448095 A CA2448095 A CA 2448095A CA 2448095 A1 CA2448095 A1 CA 2448095A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- triglyceride
- ocor2
- group
- ocor3
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
Classifications
-
- A—HUMAN NECESSITIES
- A21—BAKING; EDIBLE DOUGHS
- A21D—TREATMENT, e.g. PRESERVATION, OF FLOUR OR DOUGH, e.g. BY ADDITION OF MATERIALS; BAKING; BAKERY PRODUCTS; PRESERVATION THEREOF
- A21D2/00—Treatment of flour or dough by adding materials thereto before or during baking
- A21D2/08—Treatment of flour or dough by adding materials thereto before or during baking by adding organic substances
- A21D2/14—Organic oxygen compounds
- A21D2/16—Fatty acid esters
- A21D2/165—Triglycerides
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
-
- 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
Abstract
The present invention generally relates to a reduced calorie fat. More specifically, the present invention relates to a modified natural triglyceride which is metabolized less efficiently than traditional triglycerides resulting in reduced caloric intake. The triglyceride compositions of the present invention are described by the general formula:
(See Formula I) wherein -OCOR1 and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein R2 is a short chain fatty acid having less than 12 carbon atoms.
(See Formula I) wherein -OCOR1 and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein R2 is a short chain fatty acid having less than 12 carbon atoms.
Description
Docket 67207 A REDUCED CALORIE IFAT
Field of the Invention The present invention generally relates to a reduced calorie fat. More specifically, the present invention relates to a modified natural triglyceride s which is metabolized less efficiently than traditional triglycerides resulting in reduced caloric intake.
Background of the Invention Fat is an essential component of the human diet and is required for energy as we61 as production of cell membranes, blood lipids, bile, steroids, and Vitamin D. Chemically, fats are made from the combination of fatty acids and glycerol. The major components in most fats are triglycerides which are derived from the combination of three fatty acids and glycerol. The characteristics of the triglyceride are generally determined by the specific fatty acids in the triglyceride. For example, vegetable oils are generally composed 1s of triglycerides appended with three long chain unsaturated fatty acids.
Hard fats such as lard and butter generally contain triglycerides with high levels saturated fatty acids.
Although fats are necessary for essential bodily functions, consumption of excess fats in various foodstuffs contributes significantly to obesity.
High 20 fat diets also contribute to various human diseases such as heart and coronary diseases. One method of reducing obesity andlor diseases such as heart and coronary diseases in the human population is to reduce the consumption of fat. In recent years, fat substitutes or low-calorie fats have attracted increasing attention as a method of reducing the fat and calorie 25 content of foodstuffs. In particular, fat substitutes or tow-calorie fats which are capable of reducing caloric intake without sacrificing the functionality and organoleptic attributes associated with fat-containing foods are highly desirable.
Docket 67207 One attempt to lower the caloric content of foods has been the production of modified fats that are partially or wholly indigestible and thus comparatively low in available calories. For example, U.S. Patents 3,963,699 (June 15, 1976), 4,005,195 (January 25, 1977), 5,422,131 (June 6, 1995), 5,294,451 (March 15, 1994), 5,491,226 (February 13, 1996), 5,518,754 (May 21, 1996), 5,585,132 (December 17, 1996), and 5,968,566 (October 19, 1999) describe nonabsorbable, nondigestible fat substitutes comprising certain polyol fatty acid polyesters having at feast 4 fatty acid ester groups.
Such fat substitutes often result in digestive problems (e.g., anal Leakage) and generally only poorly mimic the organoleptic properties of natural fats.
U.S. Patents 5,378,490 (January 3, 1995), 5,258,197 (November 15, 1993), 5,411,756 (May 2, 1995), 5,456,939 (October 10, 1995), 5,552,174 (September 3, 1996), 5,565,232 (October 15, 1996), and 5,662,953 (September 2, 1997) provide modified triglyceride fat substitutes. These fat ~s substitutes generally are mixtures of at least two triglycerides bearing long-chain saturated fatty acid residues and short-chain fatty acid residues. The long-chain saturated fatty acids are poorly absorbed when consumed resulting in fewer available calories contributed to the diet. These fat substitutes generally have less than about 15 percent, and preferably less 2o than about 10 percent, unsaturated fatty acids.
Diets high in saturated fat have been shown to increase the risk of heart disease. It is, therefore, desirable to provide reduced-fat triglycerides made primarily of unsaturated fatty acids. it is also desirable to provide a reduced fat triglyceride with physical and organoleptic characteristics similar 2s to natural unsaturated fats. The present invention provides natural reduced-fat triglycerides made primary of unsaturated fatty acids. The modified fats produced by the present invention provide improved textural, organoleptic, and hydrophillic properties which closely resemble those of fiats normally used in food products.
Field of the Invention The present invention generally relates to a reduced calorie fat. More specifically, the present invention relates to a modified natural triglyceride s which is metabolized less efficiently than traditional triglycerides resulting in reduced caloric intake.
Background of the Invention Fat is an essential component of the human diet and is required for energy as we61 as production of cell membranes, blood lipids, bile, steroids, and Vitamin D. Chemically, fats are made from the combination of fatty acids and glycerol. The major components in most fats are triglycerides which are derived from the combination of three fatty acids and glycerol. The characteristics of the triglyceride are generally determined by the specific fatty acids in the triglyceride. For example, vegetable oils are generally composed 1s of triglycerides appended with three long chain unsaturated fatty acids.
Hard fats such as lard and butter generally contain triglycerides with high levels saturated fatty acids.
Although fats are necessary for essential bodily functions, consumption of excess fats in various foodstuffs contributes significantly to obesity.
High 20 fat diets also contribute to various human diseases such as heart and coronary diseases. One method of reducing obesity andlor diseases such as heart and coronary diseases in the human population is to reduce the consumption of fat. In recent years, fat substitutes or low-calorie fats have attracted increasing attention as a method of reducing the fat and calorie 25 content of foodstuffs. In particular, fat substitutes or tow-calorie fats which are capable of reducing caloric intake without sacrificing the functionality and organoleptic attributes associated with fat-containing foods are highly desirable.
Docket 67207 One attempt to lower the caloric content of foods has been the production of modified fats that are partially or wholly indigestible and thus comparatively low in available calories. For example, U.S. Patents 3,963,699 (June 15, 1976), 4,005,195 (January 25, 1977), 5,422,131 (June 6, 1995), 5,294,451 (March 15, 1994), 5,491,226 (February 13, 1996), 5,518,754 (May 21, 1996), 5,585,132 (December 17, 1996), and 5,968,566 (October 19, 1999) describe nonabsorbable, nondigestible fat substitutes comprising certain polyol fatty acid polyesters having at feast 4 fatty acid ester groups.
Such fat substitutes often result in digestive problems (e.g., anal Leakage) and generally only poorly mimic the organoleptic properties of natural fats.
U.S. Patents 5,378,490 (January 3, 1995), 5,258,197 (November 15, 1993), 5,411,756 (May 2, 1995), 5,456,939 (October 10, 1995), 5,552,174 (September 3, 1996), 5,565,232 (October 15, 1996), and 5,662,953 (September 2, 1997) provide modified triglyceride fat substitutes. These fat ~s substitutes generally are mixtures of at least two triglycerides bearing long-chain saturated fatty acid residues and short-chain fatty acid residues. The long-chain saturated fatty acids are poorly absorbed when consumed resulting in fewer available calories contributed to the diet. These fat substitutes generally have less than about 15 percent, and preferably less 2o than about 10 percent, unsaturated fatty acids.
Diets high in saturated fat have been shown to increase the risk of heart disease. It is, therefore, desirable to provide reduced-fat triglycerides made primarily of unsaturated fatty acids. it is also desirable to provide a reduced fat triglyceride with physical and organoleptic characteristics similar 2s to natural unsaturated fats. The present invention provides natural reduced-fat triglycerides made primary of unsaturated fatty acids. The modified fats produced by the present invention provide improved textural, organoleptic, and hydrophillic properties which closely resemble those of fiats normally used in food products.
Docket 67207 Summa~yr of th_e Invention The present invention relates to triglycerides having reduced calorie characteristics. The triglyceride compositions of the present invention are described by the general formula:
CORD
CH-O CORZ
Hz s wherein -OCOR, and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein -OCOR2 is a short chain fatty acid having less than 12 carbon atoms. The fat of the current invention has flavor and texture attributes similar to that of natural vegetable oils. Additionally, the fat of the current invention may be partially hydrogenated to provide firmer texture, control melting point, and improve functionality. For purposes of this invention, "substantially unsaturated" is intended to provide for at least 20 percent of the long chain fatty acids to be unsaturated, preferably at least about 50 percent of the long chain fatty acids to be unsaturated, and more preferably at least about 80 percent of the long ~5 chain fatty acids to be unsaturated.
The fat compositions that are the subject of the current invention are generally in the form of triglycerides with a short chain fatty acid in the middle or RZ position and long chain unsaturated fatty acids in the terminal R, and positions. Due to their unique structure, the fat compositions of the current 2o invention are absorbed and metabolized less efficiently than normal triglycerides, resulting in fewer calories contributed to the diet. The caloric value of triglyceride compositions of the current invention is estimated to be Docket 67207 about 5.9 kcal/g as compared to about 9.0 kcal/g for conventional triglycerides.
In normal fat metabolism, pancreatic enzymes remove the terminal R, and R3 fatty acids leaving an R2 monoglyceride. The R2 monoglyceride is absorbed by the gut mucosa, and fatty acids ace appended thereto to form a new triglyceride, which is then transported via the lymphatic system to other parts of the body for storage or metabolism.
When the modified triglyceride of the current invention is ingested, the short-chain fatty acid in the middle or R2 position is rapidly hydrolyzed off by gastric enzymes resulting in a 1,3-diglyceride. The 1,3-diglyceride, unlike the R2 monoglyceride, does not combine efficiently with free fatty acids to form new triglycerides, rather, it is hydrolyzed by the body into glycerol and free fatty acids. The free fatty acids are subsequently absorbed by the gut and transported to the fiver where they are oxidized. Thus, due to their unique ~s chemical structure, the fats of the current invention are metabolized in such a way that does not promote the storage fat by the body.
Detailed Descripfion of the Invention The present invention relates to triglyceride compositions having reduced calorie characteristics which are effective in promoting weight loss.
20 The triglyceride compositions of the present invention are described by the general formula:
CORD
CORD
CH-O CORZ
Hz s wherein -OCOR, and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein -OCOR2 is a short chain fatty acid having less than 12 carbon atoms. The fat of the current invention has flavor and texture attributes similar to that of natural vegetable oils. Additionally, the fat of the current invention may be partially hydrogenated to provide firmer texture, control melting point, and improve functionality. For purposes of this invention, "substantially unsaturated" is intended to provide for at least 20 percent of the long chain fatty acids to be unsaturated, preferably at least about 50 percent of the long chain fatty acids to be unsaturated, and more preferably at least about 80 percent of the long ~5 chain fatty acids to be unsaturated.
The fat compositions that are the subject of the current invention are generally in the form of triglycerides with a short chain fatty acid in the middle or RZ position and long chain unsaturated fatty acids in the terminal R, and positions. Due to their unique structure, the fat compositions of the current 2o invention are absorbed and metabolized less efficiently than normal triglycerides, resulting in fewer calories contributed to the diet. The caloric value of triglyceride compositions of the current invention is estimated to be Docket 67207 about 5.9 kcal/g as compared to about 9.0 kcal/g for conventional triglycerides.
In normal fat metabolism, pancreatic enzymes remove the terminal R, and R3 fatty acids leaving an R2 monoglyceride. The R2 monoglyceride is absorbed by the gut mucosa, and fatty acids ace appended thereto to form a new triglyceride, which is then transported via the lymphatic system to other parts of the body for storage or metabolism.
When the modified triglyceride of the current invention is ingested, the short-chain fatty acid in the middle or R2 position is rapidly hydrolyzed off by gastric enzymes resulting in a 1,3-diglyceride. The 1,3-diglyceride, unlike the R2 monoglyceride, does not combine efficiently with free fatty acids to form new triglycerides, rather, it is hydrolyzed by the body into glycerol and free fatty acids. The free fatty acids are subsequently absorbed by the gut and transported to the fiver where they are oxidized. Thus, due to their unique ~s chemical structure, the fats of the current invention are metabolized in such a way that does not promote the storage fat by the body.
Detailed Descripfion of the Invention The present invention relates to triglyceride compositions having reduced calorie characteristics which are effective in promoting weight loss.
20 The triglyceride compositions of the present invention are described by the general formula:
CORD
Docket672o7 wherein -OCOR, and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein -OCOR2 is a short chain fatty acid having less than 12 carbon atoms. For purposes of this invention, "substantially unsaturated° is intended to provide for at least 20 percent of the long chain fatty acids to be unsaturated, preferably at feast about 50 percent of the long chain fatty acids to be unsaturated, and more preferably at least about 80 percent of the long chain fatty acids to be unsaturated. Even more preferably, the triglyceride compositions of the present invention are described by the general formula:
cOR, ~o wherein -OCOR, and -OCOR3 are independently unsaturated long chain fatty acids having at least 18 carbon atoms and wherein -OCOR2 is a short chain fatty acid having less than 5 carbon atoms.
Even more preferably, the triglycerides of the present invention consists essentially of the general formula:
COR, H2C\
\CH-O CORz Docket67207 wherein -OCOR, and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein -OCORZ is a short chain fatty acid having less than 12 carbon atoms.
Examples of unsaturated long-chain fatty acids that may be utilized in the R, and R3 positions are oleic, linoleic, and linolenic acids. Examples of short chain fatty acids that may be utilized in the RZ position are acetic, propanoic, and butyric acids. The triglyceride composition is designed to be less efficiently stored in the body when compared to traditional triglycerides.
The caloric value of triglycerides of the current invention are estimated to be about 5.9 kcal/g as compared to about 9.0 kcallg for normal triglycerides.
Preferred triglycerides of the current invention include 1,3-dioleyl-2-acetyl glycerol and 1,3-dioleyl-2-propionylglycerol. The more preferred triglyceride is 1,3-dioleyi-2-butyrylglycerol.
The present invention also relates to food compositions containing the triglycerides as described above. Generally such food compositions contain less than about 80 percent of the present triglycerides, preferably about 5 to about 50 percent, and more preferably about 15 to about 30 percent. Thus, the present triglycerides can be substituted for other fats normally included in food compositions (e.g., soy oil, canola oil, corn oil, and the tike); the present 2o triglycerides can replace essentially all or only a portion of such other fats as desired. The present triglycerides are effective at dissolving up to about 10 percent water or glycerinelwater mixtures. Inclusion of water or glycerinelwater further dilutes the caloric value of the present triglycerides and does not significantly effect the performance of present triglycerides in food 2s compositions such as, for example, dressings, confections, dairy products (e.g., yogurt, natural or processed cheese, ice cream), fillings, baked goods (e.g., cookies, crackers, sweet goods, and the like). The present triglycerides could also be used as cooking oils or vegetable oil.
The triglycerides of the current invention may be produced be 3o produced by two-step process by which 1,3-diglycerides having long chain fatty acids are first produced and further processed to append the short chain _6_ .. ,._..... .. _...__.__.~_...._. ,_..... ~ "...____.,.._.
..._._~_____,_...._._,~ 02448095 2003-11-04 _., _._._ ...._._ .__,..__._ ...._ _._.__._".._...,__._,._.._,.. _. . .
Docket 67207 fatty acid. To produce the 1,3-diglyceride, any of several technologies including chemical synthesis, conventional lipase, or unique Sn2 specific lipase may be used. The resulting diglyceride are then acylated with acetic, propionic or butyric anhydride. Alternatively, acylation can be accomplished using the acid resulting triglyceride can be hydrogenated to various degrees to control the functionality.
The following example is included to illustrate the invention and not to limit it. Unless otherwise indicated, all percentages are by weight. Atl patents and references cited in the present specification are hereby incorporated by 1 o reference.
Example. A commercial diglyceride (25 ml; Econa Cooking Oil, Kao Corp., ,fapan) was refluxed for two hours with 5 ml of butyric anhydride. The resulting material was steam distilled for two hours under house vacuum to remove excess butyric acid. About 18 g of a modified oil (about 70 percent triglyceride having long chain unsaturated fatty acids in the 1 and 3 positions and butyrate in the 2 position and about 30 percent triglyceride having long chain unsaturated fatty acids in the 2 and 3 positions and butyrate in the 1 position) was recovered.
A similar product was prepared by reacting acetic anhydride (5 ml) as 2o the acylating agent with the same commercial diglyceride (25 ml) under similar conditions. About 14g of a modified oil (about 70 percent triglyceride having long chain unsaturated fatty acids in the 1 and 3 positions and acetate in the 2 position and about 30 percent triglyceride having long chain unsaturated fatty acids in the 2 and 3 positions and acetate in the 1 position) was recovered.
Product identity of both oils were confirmed using NMR. Both products , can be incorporated into food products in replace natural fats and provide lower calorie products.
_7_
cOR, ~o wherein -OCOR, and -OCOR3 are independently unsaturated long chain fatty acids having at least 18 carbon atoms and wherein -OCOR2 is a short chain fatty acid having less than 5 carbon atoms.
Even more preferably, the triglycerides of the present invention consists essentially of the general formula:
COR, H2C\
\CH-O CORz Docket67207 wherein -OCOR, and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein -OCORZ is a short chain fatty acid having less than 12 carbon atoms.
Examples of unsaturated long-chain fatty acids that may be utilized in the R, and R3 positions are oleic, linoleic, and linolenic acids. Examples of short chain fatty acids that may be utilized in the RZ position are acetic, propanoic, and butyric acids. The triglyceride composition is designed to be less efficiently stored in the body when compared to traditional triglycerides.
The caloric value of triglycerides of the current invention are estimated to be about 5.9 kcal/g as compared to about 9.0 kcallg for normal triglycerides.
Preferred triglycerides of the current invention include 1,3-dioleyl-2-acetyl glycerol and 1,3-dioleyl-2-propionylglycerol. The more preferred triglyceride is 1,3-dioleyi-2-butyrylglycerol.
The present invention also relates to food compositions containing the triglycerides as described above. Generally such food compositions contain less than about 80 percent of the present triglycerides, preferably about 5 to about 50 percent, and more preferably about 15 to about 30 percent. Thus, the present triglycerides can be substituted for other fats normally included in food compositions (e.g., soy oil, canola oil, corn oil, and the tike); the present 2o triglycerides can replace essentially all or only a portion of such other fats as desired. The present triglycerides are effective at dissolving up to about 10 percent water or glycerinelwater mixtures. Inclusion of water or glycerinelwater further dilutes the caloric value of the present triglycerides and does not significantly effect the performance of present triglycerides in food 2s compositions such as, for example, dressings, confections, dairy products (e.g., yogurt, natural or processed cheese, ice cream), fillings, baked goods (e.g., cookies, crackers, sweet goods, and the like). The present triglycerides could also be used as cooking oils or vegetable oil.
The triglycerides of the current invention may be produced be 3o produced by two-step process by which 1,3-diglycerides having long chain fatty acids are first produced and further processed to append the short chain _6_ .. ,._..... .. _...__.__.~_...._. ,_..... ~ "...____.,.._.
..._._~_____,_...._._,~ 02448095 2003-11-04 _., _._._ ...._._ .__,..__._ ...._ _._.__._".._...,__._,._.._,.. _. . .
Docket 67207 fatty acid. To produce the 1,3-diglyceride, any of several technologies including chemical synthesis, conventional lipase, or unique Sn2 specific lipase may be used. The resulting diglyceride are then acylated with acetic, propionic or butyric anhydride. Alternatively, acylation can be accomplished using the acid resulting triglyceride can be hydrogenated to various degrees to control the functionality.
The following example is included to illustrate the invention and not to limit it. Unless otherwise indicated, all percentages are by weight. Atl patents and references cited in the present specification are hereby incorporated by 1 o reference.
Example. A commercial diglyceride (25 ml; Econa Cooking Oil, Kao Corp., ,fapan) was refluxed for two hours with 5 ml of butyric anhydride. The resulting material was steam distilled for two hours under house vacuum to remove excess butyric acid. About 18 g of a modified oil (about 70 percent triglyceride having long chain unsaturated fatty acids in the 1 and 3 positions and butyrate in the 2 position and about 30 percent triglyceride having long chain unsaturated fatty acids in the 2 and 3 positions and butyrate in the 1 position) was recovered.
A similar product was prepared by reacting acetic anhydride (5 ml) as 2o the acylating agent with the same commercial diglyceride (25 ml) under similar conditions. About 14g of a modified oil (about 70 percent triglyceride having long chain unsaturated fatty acids in the 1 and 3 positions and acetate in the 2 position and about 30 percent triglyceride having long chain unsaturated fatty acids in the 2 and 3 positions and acetate in the 1 position) was recovered.
Product identity of both oils were confirmed using NMR. Both products , can be incorporated into food products in replace natural fats and provide lower calorie products.
_7_
Claims (21)
1. A trigiyceride having reduced calorie characteristics.which are effective in promoting weight loss, said triglyceride comprising the formula wherein -OCOR1 and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein -OCOR2 is a short chain fatty acid having less than 12 carbon atoms;
whereby the triglyceride composition has reduced calorie characteristics which are effective in promoting weight loss.
whereby the triglyceride composition has reduced calorie characteristics which are effective in promoting weight loss.
2. The triglyceride as described in claim 1, wherein -OCOR1 and -OCOR3 are independently selected from the group consisting of oleic acid, linoleic acid, and linolenic acid.
3. The triglyceride as described in claim 1, wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
4. The triglyceride as described in claim 2, wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
5. The triglyceride as described in claim 1, wherein -OCOR1 and -OCOR3 are oleic acid and wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
6. A triglyceride having reduced calorie characteristics which are effective in promoting weight loss, said triglyceride comprising the formula wherein -OCOR1 and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein -OCOR2 is a short chain fatty acid having less than 12 carbon atoms;
whereby the triglyceride composition has reduced calorie characteristics which are effective in promoting weight loss.
whereby the triglyceride composition has reduced calorie characteristics which are effective in promoting weight loss.
7. The triglyceride as described in claim 6, wherein -OCOR1 and -OCOR3 are independently selected from the group consisting of oleic acid, linoleic acid, and linolenic acid.
8. The triglyceride as described in claim 6, wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
9. The triglyceride as described in claim 7, wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
10. The triglyceride as described in claim 6, wherein -OCOR1 and -OCOR3 are oleic acid and wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
11. A low calorie food composition containing less than about 80 percent of a triglyceride having reduced calorie characteristics which ace effective in promoting weight loss, wherein the triglyceride comprises the formula wherein -OCOR1 and -OCOR3 are independently substantially unsaturated long chain fatty acids having at least 16 carbon atoms and wherein -OCOR2 is a short chain fatty acid having less than 12 carbon atoms;
whereby the triglyceride has reduced calorie characteristics which are effective in promoting weight loss.
whereby the triglyceride has reduced calorie characteristics which are effective in promoting weight loss.
12. The low calorie food composition as described in claim 11, wherein the food composition contains about 5 to about 50 percent of the triglyceride.
13. The low calorie food composition as described in claim 11, wherein the food composition contains about 15 to about 30 percent of the triglyceride.
14. The low calorie food composition as described in claim 11, wherein -OCOR1 and -OCOR3 are independently selected from the group consisting of oleic acid, linoleic acid, and linolenic acid.
15. The low calorie food composition as described in claim 11, wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
16. The low calorie food composition as described in claim 14, wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
17. The low calorie food composition as described in claim 11, wherein -OCOR1 and -OCOR3 are oleic acid and wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
18. The low calorie food composition as described in claim 13, wherein -OCOR1 and -OCOR3 are independently selected from the group consisting of oleic acid, linoleic acid, and linolenic acid.
19. The low calorie food composition as described in claim 13, wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
20. The low calorie food composition as described in claim 18, wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
21. The low calorie food composition as described in claim 13, wherein -OCOR1 and -OCOR3 are oleic acid and wherein -OCOR2 is selected from the group consisting of acetic acid, propionic acid, and butyric acid.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/289,112 US20040086621A1 (en) | 2002-11-06 | 2002-11-06 | Reduced calorie fat |
| US10/289,112 | 2002-11-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2448095A1 true CA2448095A1 (en) | 2004-05-06 |
Family
ID=32176051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002448095A Abandoned CA2448095A1 (en) | 2002-11-06 | 2003-11-04 | A reduced calorie fat |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US20040086621A1 (en) |
| CA (1) | CA2448095A1 (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITFI20050024A1 (en) * | 2005-02-14 | 2006-08-15 | Fernando Cantini | LIPIDS FOR ANIMAL FEEDING |
| US20110077300A1 (en) * | 2009-03-26 | 2011-03-31 | Jianping Ye | Metabolic Benefits to Butyrate as a Chronic Diet Supplement |
| MX2020012344A (en) * | 2018-06-01 | 2021-01-20 | Nestle Sa | Dietary butyrate. |
| US20220218647A1 (en) * | 2019-05-21 | 2022-07-14 | Societe Des Produits Nestle S.A. | Dietary butyrate |
| AU2020278826A1 (en) * | 2019-05-21 | 2021-10-28 | Société des Produits Nestlé S.A. | Dietary butyrate and its uses |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3963699A (en) * | 1974-01-10 | 1976-06-15 | The Procter & Gamble Company | Synthesis of higher polyol fatty acid polyesters |
| US4005195A (en) * | 1976-02-12 | 1977-01-25 | The Procter & Gamble Company | Compositions for treating hypercholesterolemia |
| US5258197A (en) * | 1989-09-20 | 1993-11-02 | Nabisco, Inc. | Reduced calorie triglyceride mixtures |
| US5662953A (en) * | 1989-09-20 | 1997-09-02 | Nabisco, Inc. | Reduced calorie triglyceride mixtures |
| US5411756A (en) * | 1989-09-20 | 1995-05-02 | Nabisco, Inc. | Reduced calorie triglyceride mixtures |
| US5294451A (en) * | 1991-03-29 | 1994-03-15 | Curtice-Burns, Inc. | Fat substitute compositions having reduced laxative effects |
| US5422131A (en) * | 1992-10-30 | 1995-06-06 | The Procter & Gamble Company | Nondigestible fat compositions containing relatively small nondigestible solid particles for passive oil loss control |
| JPH08509513A (en) * | 1993-04-23 | 1996-10-08 | ロダース・クロックラーン・ビー・ブイ | Nourishing fats and oils with improved digestibility |
| US5491226A (en) * | 1994-04-06 | 1996-02-13 | Procter & Gamble Company | Process for preparing polyol polyesters having low levels of triglycerides |
| US5518754A (en) * | 1994-08-19 | 1996-05-21 | Kraft Foods, Inc. | Chocolate products with sucrose fatty acid polyester fat substitutes |
| US5765623A (en) * | 1994-12-19 | 1998-06-16 | Inco Limited | Alloys containing insoluble phases and method of manufacture thereof |
| US6410078B1 (en) * | 1995-04-28 | 2002-06-25 | Loders-Croklaan B.V. | Triglycerides, rich in polyunsaturated fatty acids |
| US5968566A (en) * | 1996-05-14 | 1999-10-19 | Mlp Operating Company | Refrigerated yeast-raised pizza dough |
| TW479064B (en) * | 1996-12-17 | 2002-03-11 | Advanced Elastomer Systems | Thermoplastic elastomeric compositions |
| US6525157B2 (en) * | 1997-08-12 | 2003-02-25 | Exxonmobile Chemical Patents Inc. | Propylene ethylene polymers |
| US6921794B2 (en) * | 1997-08-12 | 2005-07-26 | Exxonmobil Chemical Patents Inc. | Blends made from propylene ethylene polymers |
| US6635715B1 (en) * | 1997-08-12 | 2003-10-21 | Sudhin Datta | Thermoplastic polymer blends of isotactic polypropylene and alpha-olefin/propylene copolymers |
| CN1292014A (en) * | 1998-03-04 | 2001-04-18 | 埃克森化学专利公司 | Polyolefin polymer dispersion product and its preparing process |
| DE69935815T2 (en) * | 1998-07-01 | 2007-12-27 | Exxonmobil Chemical Patents Inc., Baytown | Elastic mixture with crystal polymers and crystallizable polymers of propene |
| US6288171B2 (en) * | 1998-07-01 | 2001-09-11 | Advanced Elastomer Systems, L.P. | Modification of thermoplastic vulcanizates using random propylene copolymers |
| KR20010079767A (en) * | 1998-09-11 | 2001-08-22 | 러세쓰 리차드 큐. | Reduced Calorie Plastic Fat Composition |
| US6500563B1 (en) * | 1999-05-13 | 2002-12-31 | Exxonmobil Chemical Patents Inc. | Elastic films including crystalline polymer and crystallizable polymers of propylene |
| MXPA01011548A (en) * | 1999-05-13 | 2002-07-02 | Exxon Chemical Patents Inc | Elastic fibers and articles made therefrom, including crystalline and crystallizable polymers of propylene. |
| US6750284B1 (en) * | 1999-05-13 | 2004-06-15 | Exxonmobil Chemical Patents Inc. | Thermoplastic filled membranes of propylene copolymers |
| WO2000069966A1 (en) * | 1999-05-19 | 2000-11-23 | Exxon Chemical Patents Inc. | Isobutylene based elastomer blends having improved strength, elasticity, and reduced permeability |
| WO2001016228A1 (en) * | 1999-09-01 | 2001-03-08 | Exxon Chemical Patents Inc. | Breathable films and method for making |
| CN1333032C (en) * | 1999-12-22 | 2007-08-22 | 埃克森美孚化学专利公司 | Adhesive alpha-olefin inter-polymers |
-
2002
- 2002-11-06 US US10/289,112 patent/US20040086621A1/en not_active Abandoned
-
2003
- 2003-11-04 CA CA002448095A patent/CA2448095A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20040086621A1 (en) | 2004-05-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BELL et al. | The new dietary fats in health and disease | |
| Kris-Etherton et al. | Dietary stearic acid and risk of cardiovascular disease: intake, sources, digestion, and absorption | |
| Lee et al. | Health benefits, enzymatic production, and application of medium‐and long‐chain triacylglycerol (MLCT) in food industries: a review | |
| US5008126A (en) | Long chain diol diesters as low calorie fat mimetics | |
| JP3569116B2 (en) | Liquid general-purpose fat composition | |
| US4959466A (en) | Partially esterified polysaccharide (PEP) fat substitutes | |
| US5589217A (en) | Reduced calorie fat component | |
| US4673581A (en) | Fried food product fried in synthetic cooking oils containing dicarboxylic acid esters | |
| WO2003090548A1 (en) | Low calorie oils which develop characteristic flavor notes during frying | |
| Dupont et al. | Saturated and hydrogenated fats in food in relation to health. | |
| US8911813B2 (en) | Structured lipid compositions | |
| AU2009288740A1 (en) | Balanced sn-2 myristate-containing edible oil | |
| CA2168051A1 (en) | Reduced calorie fat component | |
| IE67539B1 (en) | Reduced calorie fat mimetics comprising esterified propoxylated monoglycerides and diglycerides | |
| Gurr | Lipids and nutrition | |
| Akoh | Structured and specialty lipids | |
| EP1060675B1 (en) | Reduced calorie fat mimetics with an average number of oxyalkylene groups per molecule of 2 | |
| US20040086621A1 (en) | Reduced calorie fat | |
| US20110151102A1 (en) | Fat or oil composition | |
| US4992293A (en) | Thioester derivatives as low calorie fat mimetics | |
| US5063075A (en) | Amide ether derivatives as low calorie fat mimetics | |
| US5068119A (en) | Acid-hydrolyzable ester derivatives as low calorie fat mimetics | |
| Auerbach et al. | Reduced energy lipids | |
| US5068120A (en) | Amine ester derivatives as low calorie fat mimetics | |
| WO2001060172A1 (en) | Low calorie fat compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20071105 |