WO1998048641A1 - Method of increasing fat firmness and improving meat quality in animals - Google Patents

Method of increasing fat firmness and improving meat quality in animals Download PDF

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Publication number
WO1998048641A1
WO1998048641A1 PCT/US1997/019465 US9719465W WO9848641A1 WO 1998048641 A1 WO1998048641 A1 WO 1998048641A1 US 9719465 W US9719465 W US 9719465W WO 9848641 A1 WO9848641 A1 WO 9848641A1
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WO
WIPO (PCT)
Prior art keywords
cla
animal
meat
fat
animals
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Ceased
Application number
PCT/US1997/019465
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French (fr)
Inventor
Mark E. Cook
Daria L. Jerome
Michael D. Pariza
Dennis R. Buege
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Wisconsin Alumni Research Foundation
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Wisconsin Alumni Research Foundation
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Publication date
Application filed by Wisconsin Alumni Research Foundation filed Critical Wisconsin Alumni Research Foundation
Priority to CA002283488A priority Critical patent/CA2283488C/en
Priority to DK97912955T priority patent/DK0977492T3/en
Priority to NZ337448A priority patent/NZ337448A/en
Priority to EP97912955A priority patent/EP0977492B1/en
Priority to AU50016/97A priority patent/AU729061B2/en
Priority to JP54693498A priority patent/JP2002501383A/en
Priority to AT97912955T priority patent/ATE229279T1/en
Priority to DE69717864T priority patent/DE69717864T2/en
Publication of WO1998048641A1 publication Critical patent/WO1998048641A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S426/00—Food or edible material: processes, compositions, and products
    • Y10S426/807—Poultry or ruminant feed

Definitions

  • the present application generally relates to methods of treating animals. More particularly, it relates to a method of treating animals to improve meat quality.
  • the method of the present invention comprises administering to an animal intended for meat a safe amount of a conjugated linoleic acid, such as 9 , 11-octadecadienoic acid and 10 , 12-octadecadienoic acid, a non-toxic salt of a conjugated linoleic acid, an active ester of a conjugated linoleic acid, an active isomer of a conjugated linoleic acid, an active metabolite of a conjugated linoleic acid or a mixture thereof, which is effective to improve meat quality and to increase the firmness of the fat in the meat which also improves the quality of the meat.
  • a conjugated linoleic acid such as 9 , 11-octadecadienoic acid and 10 , 12-octadecadienoic acid, a non-toxic salt of a conjugated linoleic acid, an active ester of a conjugated linoleic acid,
  • the increased firmness of the fat allows for improved processing, such as slicing of pork bellies into bacon.
  • the method of the present invention also allows the feed industry to feed a higher concentration of unsaturated fatty acid (i.e. vegetable oil) to meat animals without causing undesirable soft tissue and soft fat meat products .
  • conjugated linoleic acids their non-toxic salts, active esters, active isomers, active metabolites, and mixtures thereof are collectively referred to herein as "conjugated linoleic acid" or "CLA” .
  • the CLA is orally administered to the animal in a safe amount which is effective to improve meat quality and to increase the firmness of the fat in the animal which also improves the quality of meat obtained from the animal . Because of the differences in ages, size and nature of animals, the amounts which are safe and effective may vary considerably. Since CLA is a natural food ingredient and it is relatively non-toxic, the amounts which can be administered in the methods of the invention are not critical as long as they are enough to be effective.
  • Example 1 Pig weighing approximately 55 pounds were fed 0., 0.5 or 1.0 percent CLA by weight in their diet . After three and a half months, the pigs were slaughtered and the carcasses cooled prior to processing. When the carcasses were removed, a visible difference was seen between the stiffness of the pork bellies and subcutaneous fat of the control pigs and the pigs fed CLA. The pork bellies and subcutaneous fat from the CLA-fed animals were firmer and the bellies did not collapse when hung over a rod. The bellies were scored for appearance, consistency and fat firmness. Also, indices of meat quality (color, marbling, and water holding capacity) were determined. The results are shown in Tables 1 and 2. TABLE 1 MEASURE OF MUSCLE QUALITY
  • Subjective Color This is based on a score of 1-5 with one being undesirable, 3-4 preferable, and 5 too dark.
  • Minolta Colorimeter readings The L* value is a measure of lightness with the higher values being more light (closer to white) . Pork should not be white in color; if it is this is an indication of PSE (pale, soft, exudative) . PSE pork is very undesirable due to its off taste, poor binding characteristic, and loss of water. The a+ value is redness of the meat with the higher value meaning it is more red.
  • Water Holding Capacity This is another measure of PSE. It is done by placing a piece of filter paper on the muscle after it has been exposed for 10 minutes (bloomed) and then weighing the amount of moisture picked up on the paper in mg . TABLE 2
  • the pigs fed CLA diets containing CLA had better muscle quality and pork bellies which were significantly better for making bacon than the bellies of the control pigs.
  • the method of the present invention may take several embodiments.
  • the CLA is added to an animal's diet by adding the CLA to feed.
  • the CLA can be administered to an animal in a veterinary composition containing a safe and effective dose of the CLA.
  • the meat animal is fed a food product, such as milk, vegetable oils or egg solids, which have been enriched so that they contain high concentrations of CLA.
  • the feed and veterinary preparations for use in the methods of the present invention preferably are those containing the CLA in the form of a free fatty acid or triglyceride esters in combination with a conventional feed or approved veterinary diluent.
  • Other active forms of CLA including, without limitation, the non-toxic salts and mixtures can be used.
  • the free conjugated linoleic acids (CLA) have been previously isolated from fried meats and described as anticarcinogens by Y. L. Ha, N. K. Grimm and M. W. Pariza, in Carcinogenesis Vol. 8, No. 12, pp. 1881-1887 (1987). Since then, they have been found in some processed cheese products (Y.L. Ha, N. K. Grimm and M. W. Pariza, in J. Agric. Food Chem. , Vol. 37, No. 1, pp. 75-81 (1987)).
  • the free acid forms of the CLA may be prepared by isomerizing linoleic acid.
  • the non-toxic salts of the free CLA acids may be made by reacting the free acids with a non- toxic base.
  • Natural CLA may also be isolated from tallow or prepared from linoleic acid by the action of W 12 -cis, W 11 - transisomerase from a harmless microorganism such as the Rumen bacterium Butyri vibrio fibrisolvens . Harmless microorganisms in the intestinal tracts of rats and other monogastric animals may also convert linoleic acid to CLA (S.F. Chin, W. Liu, K. Albright and M.W. Pariza, 1992, FASEB J.6:Abstract #2665).
  • the CLA obtained by the practice of the described methods of preparation contains one or more of the 9, 11-octadecadienoic acids and/or 10 , 12-octadecadienoic acids and active isomers thereof. It may be free or bound chemically through ester linkages.
  • the CLA is heat stable and can be used as is, or dried and powdered.
  • the free acids are readily converted into non-toxic salts, such as the sodium or potassium salts, by reacting chemically equivalent amounts of the free acid with an alkali hydroxide at a pH of about 8 to 9.
  • c9,tll- and tl0,cl2- isomers are predominantly produced during the autoxidation or alkali-isomerization of c9, cl2 -linoleic acid due to the co-planar characteristics of 5 carbon atoms around a conjugated double-bond and spatial conflict of the resonance radical.
  • the remaining two c,c-isomers are minor contributors.
  • the relatively higher distribution of the t,t- isomers of 9,11- or 10 , 12-octadecadienoic acid apparently results from the further stabilization of c9,tll- or tlO, cl2-geometric isomers, which is thermodynamically preferred, during an extended processing time or long aging period. Additionally the t,t-isomer of 9,11- or 10 , 12-octadecadienoic acid that was predominantly formed during the isomerization of linoleic acid geometrical isomers (t9,tl2-, c9,tl2- and t9, cl2-octadecadienoic acid) may influence the final ratio of the isomers or the final CLA content in the samples.
  • Linoleic acid geometrical isomers also influence the distribution of minor contributors (c,c-isomers of 9,11- and 10,12-, t9,cll- and ell , tl2-octadecadienoic acids).
  • the 11,13-isomer might be produced as a minor product from c9, cl2-octadecadienoic acid or from its isomeric forms during processing.
  • the CLA can be administered in the form of veterinary compositions, such as solutions or emulsions.
  • the exact amount to be administered depends upon the form of CLA employed, and the route of administration.
  • compositions of CLA contain the non-toxic sodium or potassium salt of CLA in combination with a suitable diluent.
  • a suitable diluent In addition to solutions or suspensions intended for oral administration, the composition can be a powder or a crushable tablet .
  • the preferred diluent will be Sterile Water for Injection U.S. P.
  • the amounts of CLA to be added to an animal ' s feed can range from about .01% to about 5.0% or more by weight of the animal's diet.
  • the animal can be fed a diet containing the CLA from birth to harvesting or for some other period until at least some of beneficial effects of the CLA feeding on fat firmness are obtained.
  • the method of the present invention is useful in increasing the firmness of the fat of other meat animals such as cattle, horses, sheep and goats.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Animal Husbandry (AREA)
  • Zoology (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Birds (AREA)
  • Fodder In General (AREA)
  • Feed For Specific Animals (AREA)

Abstract

A method of treating meat animals to increase fat firmness and meat quality indices which increases meat processability consists of administering to the meat animals a safe and effective amount of conjugated linoleic acid or CLA.

Description

METHOD OF INCREASING FAT FIRMNESS AND IMPROVING MEAT QUALITY IN ANIMALS
FIELD OF THE INVENTION The present application generally relates to methods of treating animals. More particularly, it relates to a method of treating animals to improve meat quality.
BACKGROUND OF THE INVENTION
As the American population increasingly uses unsaturated fats in food preparation, the resulting spent restaurant greases are increasingly unsaturated. These greases/oils are in turn used by the animal feed industries to feed meat animals, such as pigs. Because of the high degree of unsaturation of these oils, animals eating these oils have softer fat and tissue. In addition, corn is being genetically selected for higher levels of unsaturated fats. Since corn is a major component of animals diets, the use of high oil corn in place of saturated fat also soften fats and tissues. This creates a major problem in slicing meats (e.g. bacon) . The soft fat gums up the cutting line in bacon slicing operations that normally operate 24 hours a day.
The only method previously known to assure a firm fat was to feed animals fats or oils high in saturated fats. Due to current trends in human nutrition, such fats are less available for animal feeding. Also, the use of high oil corn varieties decreases the level of added animal fat in diets.
SUMMARY OF THE INVENTION It is the object of the present invention to disclose a method of increasing fat firmness and to increase meat quality of meat animals, such as pigs. We have made the surprising discovery that feeding meat animals a conjugated linoleic acid, which is an unsaturated fat, counteracts the adverse effects of the increased unsaturated fat in the diet of the meat animals and results in the production of meat of improved quality which has a firmer fat.
The method of the present invention comprises administering to an animal intended for meat a safe amount of a conjugated linoleic acid, such as 9 , 11-octadecadienoic acid and 10 , 12-octadecadienoic acid, a non-toxic salt of a conjugated linoleic acid, an active ester of a conjugated linoleic acid, an active isomer of a conjugated linoleic acid, an active metabolite of a conjugated linoleic acid or a mixture thereof, which is effective to improve meat quality and to increase the firmness of the fat in the meat which also improves the quality of the meat. The increased firmness of the fat allows for improved processing, such as slicing of pork bellies into bacon. The method of the present invention also allows the feed industry to feed a higher concentration of unsaturated fatty acid (i.e. vegetable oil) to meat animals without causing undesirable soft tissue and soft fat meat products .
The conjugated linoleic acids, their non-toxic salts, active esters, active isomers, active metabolites, and mixtures thereof are collectively referred to herein as "conjugated linoleic acid" or "CLA" .
It will be apparent to those skilled in the art that the aforementioned objects and other advantages may be achieved by the practice of the present invention. DESCRIPTION OF THE PREFERRED EMBODIMENT In the preferred method of the present invention, the CLA is orally administered to the animal in a safe amount which is effective to improve meat quality and to increase the firmness of the fat in the animal which also improves the quality of meat obtained from the animal . Because of the differences in ages, size and nature of animals, the amounts which are safe and effective may vary considerably. Since CLA is a natural food ingredient and it is relatively non-toxic, the amounts which can be administered in the methods of the invention are not critical as long as they are enough to be effective.
The practice of the present invention is further illustrated by the example which follows:
Example 1 Pig weighing approximately 55 pounds were fed 0., 0.5 or 1.0 percent CLA by weight in their diet . After three and a half months, the pigs were slaughtered and the carcasses cooled prior to processing. When the carcasses were removed, a visible difference was seen between the stiffness of the pork bellies and subcutaneous fat of the control pigs and the pigs fed CLA. The pork bellies and subcutaneous fat from the CLA-fed animals were firmer and the bellies did not collapse when hung over a rod. The bellies were scored for appearance, consistency and fat firmness. Also, indices of meat quality (color, marbling, and water holding capacity) were determined. The results are shown in Tables 1 and 2. TABLE 1 MEASURE OF MUSCLE QUALITY
Subjective Subjective Minolta Minolta Water Holding
Treatment Color 1 Marbling 2 * 3 a + Capacity (mg) 4
Control 2.2±0.70 1.9±0.6 49±3 9.9+3 96.2+52
0.5% CLA 2.5+0.53 2.1 +0.4 47+4 9.3+2 80+63
1.0% CLA 2.9±0.4 2.2±0.5 47±4 10.1±3 78.8+41
Measurements taken on the longissimus dorsi muscle.
Subjective Color: This is based on a score of 1-5 with one being undesirable, 3-4 preferable, and 5 too dark.
Subjective Marbling: This is a score of 1-5 with 1 meaning very little to no marbling (intramuscular fat) and 5 having a lot of marbling (equal to a prime quality grade) . Today's trends would lean in the 2-3 range.
Minolta Colorimeter readings : The L* value is a measure of lightness with the higher values being more light (closer to white) . Pork should not be white in color; if it is this is an indication of PSE (pale, soft, exudative) . PSE pork is very undesirable due to its off taste, poor binding characteristic, and loss of water. The a+ value is redness of the meat with the higher value meaning it is more red.
Water Holding Capacity: This is another measure of PSE. It is done by placing a piece of filter paper on the muscle after it has been exposed for 10 minutes (bloomed) and then weighing the amount of moisture picked up on the paper in mg . TABLE 2
MEASURES OF FAT FIRMNESS
Subjective Belly Stiffness
Treatment Firmn.ess 1 Span (inches)2
Control 2.5±.9 9.9±6.5
0.5% CLA 2.9±.6 13.3+J .6
1.0% CLA 3.1 + .6 20.3.+2.1
1 Subjective Firmness: This is a score of 1-5 with one being extremely soft to handle and 5 very firm to handle, preferred is around a 3-4.
2 Belly stiffness was measured by hanging bellies lean side up over a rod and measuring the distance in inches between the belly ends. The greater the distance, the stiffer the belly.
As can be seen from the above, the pigs fed CLA diets containing CLA had better muscle quality and pork bellies which were significantly better for making bacon than the bellies of the control pigs.
The method of the present invention may take several embodiments. In one embodiment, the CLA is added to an animal's diet by adding the CLA to feed. In another embodiment, the CLA can be administered to an animal in a veterinary composition containing a safe and effective dose of the CLA. In still another embodiment, the meat animal is fed a food product, such as milk, vegetable oils or egg solids, which have been enriched so that they contain high concentrations of CLA.
The feed and veterinary preparations for use in the methods of the present invention preferably are those containing the CLA in the form of a free fatty acid or triglyceride esters in combination with a conventional feed or approved veterinary diluent. Other active forms of CLA including, without limitation, the non-toxic salts and mixtures can be used. The free conjugated linoleic acids (CLA) have been previously isolated from fried meats and described as anticarcinogens by Y. L. Ha, N. K. Grimm and M. W. Pariza, in Carcinogenesis Vol. 8, No. 12, pp. 1881-1887 (1987). Since then, they have been found in some processed cheese products (Y.L. Ha, N. K. Grimm and M. W. Pariza, in J. Agric. Food Chem. , Vol. 37, No. 1, pp. 75-81 (1987)).
The free acid forms of the CLA may be prepared by isomerizing linoleic acid. The non-toxic salts of the free CLA acids may be made by reacting the free acids with a non- toxic base. Natural CLA may also be isolated from tallow or prepared from linoleic acid by the action of W 12-cis, W 11- transisomerase from a harmless microorganism such as the Rumen bacterium Butyri vibrio fibrisolvens . Harmless microorganisms in the intestinal tracts of rats and other monogastric animals may also convert linoleic acid to CLA (S.F. Chin, W. Liu, K. Albright and M.W. Pariza, 1992, FASEB J.6:Abstract #2665).
The CLA obtained by the practice of the described methods of preparation contains one or more of the 9, 11-octadecadienoic acids and/or 10 , 12-octadecadienoic acids and active isomers thereof. It may be free or bound chemically through ester linkages. The CLA is heat stable and can be used as is, or dried and powdered. The free acids are readily converted into non-toxic salts, such as the sodium or potassium salts, by reacting chemically equivalent amounts of the free acid with an alkali hydroxide at a pH of about 8 to 9.
Theoretically, 8 possible geometric isomers of 9,11- and 10, 12-octadecadienoic acid (c9,cll; c9,tll; t9,cll; t9,tll; cl0,cl2; cl0,tl2; tl0,cl2 and tl0,tl2) would form from the isomerization of c9 , cl2-octadecadienoic acid. As a result of the isomerization, only four isomers (c9,cll; c9,tll; tl0,cl2; and cl0,cl2) would be expected. However, of the four isomers, c9,tll- and tl0,cl2- isomers are predominantly produced during the autoxidation or alkali-isomerization of c9, cl2 -linoleic acid due to the co-planar characteristics of 5 carbon atoms around a conjugated double-bond and spatial conflict of the resonance radical. The remaining two c,c-isomers are minor contributors.
The relatively higher distribution of the t,t- isomers of 9,11- or 10 , 12-octadecadienoic acid apparently results from the further stabilization of c9,tll- or tlO, cl2-geometric isomers, which is thermodynamically preferred, during an extended processing time or long aging period. Additionally the t,t-isomer of 9,11- or 10 , 12-octadecadienoic acid that was predominantly formed during the isomerization of linoleic acid geometrical isomers (t9,tl2-, c9,tl2- and t9, cl2-octadecadienoic acid) may influence the final ratio of the isomers or the final CLA content in the samples.
Linoleic acid geometrical isomers also influence the distribution of minor contributors (c,c-isomers of 9,11- and 10,12-, t9,cll- and ell , tl2-octadecadienoic acids). The 11,13-isomer might be produced as a minor product from c9, cl2-octadecadienoic acid or from its isomeric forms during processing.
The CLA can be administered in the form of veterinary compositions, such as solutions or emulsions. The exact amount to be administered, of course, depends upon the form of CLA employed, and the route of administration.
The preferred veterinary compositions of CLA contain the non-toxic sodium or potassium salt of CLA in combination with a suitable diluent. In addition to solutions or suspensions intended for oral administration, the composition can be a powder or a crushable tablet . When the compositions are solutions or suspensions intended for parenteral administration the preferred diluent will be Sterile Water for Injection U.S. P.
The amounts of CLA to be added to an animal ' s feed can range from about .01% to about 5.0% or more by weight of the animal's diet. The animal can be fed a diet containing the CLA from birth to harvesting or for some other period until at least some of beneficial effects of the CLA feeding on fat firmness are obtained.
In addition to increasing the fat firmness and meat quality of pigs the method of the present invention is useful in increasing the firmness of the fat of other meat animals such as cattle, horses, sheep and goats.
It also will be readily apparent to those skilled in the art that a number of modifications or changes may be made without departing from the spirit and scope of the present invention. Therefore, the invention is only to be limited by the claims.

Claims

CLAIMS We claim:
1. A method of improving the fat firmness and meat quality of a meat animal which comprises administering to a meat animal a safe amount of CLA which is effective to increase the fat firmness and quality indices of the animal's meat.
2. The method of claim 1 in which the animal is a pig.
3. The method of claim 1 in which the CLA is a free conjugated linoleic acid.
4. The method of claim 1 in which the CLA is a non- toxic salt of a conjugated linoleic acid.
5. The method of claim 1 in which the CLA is an ester of a conjugated linoleic acid.
6. The method of claim 1 in which the CLA is administered orally.
7. The method of claim 1 in which the CLA is administered parenterally.
8. A method of counteracting the adverse effects of unsaturated fat in the diet of a meat animal which comprises administering to a meat animal a safe amount of CLA which is effective to counteract said adverse effects.
9. A method of modifying an animal food to increase the ability of the animal food to counteract the adverse effects of unsaturated fat in the diet of an animal, said method comprising adding to said animal food a safe amount of CLA, said amount being effective to counteract the adverse effects of unsaturated fat in the diet of the animal .
PCT/US1997/019465 1997-04-25 1997-10-20 Method of increasing fat firmness and improving meat quality in animals Ceased WO1998048641A1 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CA002283488A CA2283488C (en) 1997-04-25 1997-10-20 Method of increasing fat firmness and improving meat quality in animals
DK97912955T DK0977492T3 (en) 1997-04-25 1997-10-20 Method for increasing fat resistance and improving meat quality in animals
NZ337448A NZ337448A (en) 1997-04-25 1997-10-20 Method of increasing fat firmness and improving meat quality in animals by administering conjugated linoleic acid
EP97912955A EP0977492B1 (en) 1997-04-25 1997-10-20 Method of increasing fat firmness and improving meat quality in animals
AU50016/97A AU729061B2 (en) 1997-04-25 1997-10-20 Method of increasing fat firmness and improving meat quality in animals
JP54693498A JP2002501383A (en) 1997-04-25 1997-10-20 How to increase fat firmness and improve meat quality in animals
AT97912955T ATE229279T1 (en) 1997-04-25 1997-10-20 METHOD FOR INCREASING FAT STRENGTH AND IMPROVING MEAT QUALITY IN ANIMALS
DE69717864T DE69717864T2 (en) 1997-04-25 1997-10-20 METHOD FOR INCREASING FAT STRENGTH AND IMPROVING MEAT QUALITY IN ANIMALS

Applications Claiming Priority (2)

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US08/845,535 1997-04-25
US08/845,535 US5851572A (en) 1997-04-25 1997-04-25 Method of increasing fat firmness and improving meat quality in animals with conjugated linolenic acid

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WO1998048641A1 true WO1998048641A1 (en) 1998-11-05

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US (1) US5851572A (en)
EP (1) EP0977492B1 (en)
JP (2) JP2002501383A (en)
AT (1) ATE229279T1 (en)
AU (1) AU729061B2 (en)
CA (1) CA2283488C (en)
DE (1) DE69717864T2 (en)
DK (1) DK0977492T3 (en)
ES (1) ES2184071T3 (en)
NZ (1) NZ337448A (en)
WO (1) WO1998048641A1 (en)

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KR20010027513A (en) * 1999-09-14 2001-04-06 신성수 manufacture method of fodder
KR100308387B1 (en) * 1999-07-06 2001-09-13 박구부 Method for lessening contents of nitrate or nitrite in meat products
AU769135B2 (en) * 1998-12-16 2004-01-15 Wisconsin Alumni Research Foundation Method of increasing fat firmness and improving meat quality in animals
DE10260081A1 (en) * 2002-12-19 2004-07-08 Basf Ag Stabilizing compositions that contain conjugated C18 polyunsaturated fatty acids, useful e.g. in foods, feeds, cosmetics and pharmaceuticals, by adding a lipophilic compound
US6809115B2 (en) 2000-09-21 2004-10-26 Nutrition 21, Inc. Methods and compositions for the treatment of diabetes, the reduction of body fat, improvement of insulin sensitivity, reduction of hyperglycemia, and reduction of hypercholesterolemia with chromium complexes, conjugated fatty acids, and/or conjugated fatty alcohols
AU2006252054B2 (en) * 1998-08-20 2010-05-13 E.I. Du Pont De Nemours And Company Animal feed containing plant fatty acids with conjugated double bonds

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US7776353B1 (en) 1998-03-17 2010-08-17 Aker Biomarine Asa Conjugated linoleic acid compositions
US6015833A (en) * 1998-03-17 2000-01-18 Conlinco., Inc. Conjugated linoleic acid compositions
US7078051B1 (en) 1998-08-11 2006-07-18 Natural Asa Conjugated linoleic acid alkyl esters in feedstuffs and food
CA2289648C (en) * 1998-03-17 2004-06-01 Conlinco, Inc. Conjugated linoleic acid compositions
US6696584B2 (en) 1998-05-04 2004-02-24 Natural Asa Isomer enriched conjugated linoleic acid compositions
US6060514A (en) 1998-05-04 2000-05-09 Conlin Co., Inc. Isomer enriched conjugated linoleic acid compositions
US7101914B2 (en) * 1998-05-04 2006-09-05 Natural Asa Isomer enriched conjugated linoleic acid compositions
US6214372B1 (en) * 1998-05-04 2001-04-10 Con Lin Co., Inc. Method of using isomer enriched conjugated linoleic acid compositions
DK0954983T3 (en) 1998-05-04 2007-08-06 Natural Asa Methods for using isomer-enriched compositions with conjugated linoleic acid
CA2839037A1 (en) * 1998-08-20 2000-03-02 E.I. Du Pont De Nemours And Company Genes for plant fatty acid modifying enzymes associated with conjugated double bond formation
AU6399699A (en) * 1998-09-25 2000-04-17 Conlinco, Inc. Triacylglycerols of enriched cla content
US6740508B2 (en) 1999-02-11 2004-05-25 Renessen Llc Fermentation-based products from corn and method
US6610867B2 (en) 2000-08-10 2003-08-26 Renessen Llc Corn oil processing and products comprising corn oil and corn meal obtained from corn
US7083954B2 (en) * 1999-02-11 2006-08-01 Renessen Llc Method of producing fermentation-based products from corn
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