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WO1993003754A1 - Protein preparation containing the essential amino acids - Google Patents

Protein preparation containing the essential amino acids Download PDF

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Publication number
WO1993003754A1
WO1993003754A1 PCT/DK1992/000249 DK9200249W WO9303754A1 WO 1993003754 A1 WO1993003754 A1 WO 1993003754A1 DK 9200249 W DK9200249 W DK 9200249W WO 9303754 A1 WO9303754 A1 WO 9303754A1
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WO
WIPO (PCT)
Prior art keywords
protein composition
protein
nutrio
miprodan
pro
Prior art date
Application number
PCT/DK1992/000249
Other languages
French (fr)
Inventor
Povl Willadsen
Henning Skjoldborg
Original Assignee
Lube A/S
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 Lube A/S filed Critical Lube A/S
Publication of WO1993003754A1 publication Critical patent/WO1993003754A1/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/16Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/1703Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • A61K38/1709Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23JPROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J3/00Working-up of proteins for foodstuffs
    • A23J3/04Animal proteins
    • A23J3/08Dairy proteins
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23JPROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
    • A23J3/00Working-up of proteins for foodstuffs
    • A23J3/14Vegetable proteins
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00Medicinal preparations containing peptides
    • A61K38/16Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/168Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from plants

Definitions

  • the invention relates to a protein composition.
  • Proteins also named albumin
  • proteins have many functions in the human organism and control almost all body pro ⁇ Des. Proteins are sine qua non. They are a major constituent of all cells, organs and organ systems. They start reactions and control them.
  • the so-called enzymes, hormones and proteins constitute the structural basis for all tissue, connective tissue and muscular tissue, transporting essential substances in the body, e.g. oxygen, and creating the so-called antibodies, the pro ⁇ tective substances of the body.
  • the nine vital amino acids must be supplied in a certain amount and at a certain mutual ratio. If one of these sine qua non amino acids is only supplied in e.g. approx. 50% of the necessary quantity the utilization of the other amino acids will likewise be reduced to approx. 50%. The remainder is wasted and must be ex- creted in the kidney and in adverse conditions this may be detrimental to the kidneys. Consequently the correct composition of the supplied protein, a so-called high biological value is of the utmost importance. Cf. the article "Danish scientist finds new formula for the quality of protein" in the journal ⁇ konomaen No. 9-1976 publishing Inge Lise M ⁇ rup's research results concerning the biological value of proteins.
  • a protein deficiency can manifest itself in numer ⁇ ous manners. Some of the major symptoms are lassitude, myomalacia and a low resistance to infections.
  • Fig. 1 proves a higher rate of mortality when a protein deficiency is the issue.
  • Fig. 2 illustrates the relationship between the state of nutrition and sepsis upon surgical operations. An in ⁇ ferior state of nutrition thus results in an increased risk of sepsis.
  • Fig. 3 shows a table of deficiencies in protein and muscular tissue in various kinds and states of ailments.
  • Fig. 4 shows FAO's ideal aminogram and contents of various nutrients. As is illustrated all nutrients suffer from limitations when compared to the ideal that has been set.
  • the object of the present invention has been to provide a protein composition for human and veterinary uses containing the nine sine qua non proteins in a mutual relation as close to the uptimum as possible. This is achieved by a protein preparation according to the invention having the following composition:-
  • Nutrio P-PRO 2000 (brand name) or a similar sub ⁇ stance having a corresponding protein composition, Lacprodan-80 (brand name) or a similar substance having a corresponding protein composition and Miprodan 20-0 (brand name) or a similar substance having a correspond ⁇ ing protein composition
  • Nutrio P-PRO 2000 is pre ⁇ sent in a smaller quantity than each one individually of Lacprodan-80 and Miprodan 20-0, as the latter is present in the same or almost the same quantity preferably at the mutual ratio of 1:2:2:
  • Fig. 8 illustrates the composition of the nine sine qua non proteins for different mixture proportions of Nutrio, Lacprodan-80 and Miprodan 20-0.
  • the highest biological value is estab ⁇ lished at a mutual mixture proportion of 20/40/40.
  • the limiting amino acid is thyroxine.
  • the biological value is as high as 0.81, which in fact is exceptionally high.
  • Fig. 9 the analysis result with its associated amino acid composition of a tablet is stated and Fig. 10 is a table showing the calculated biological value of the nine sine qua non proteins.
  • Surgical patients, prolonged invalids (dialyses patients), cancer patients, old people, people in nurs- ing homes, athletes, emaciation, in other words in gen ⁇ eral people suffering from a protein deficiency can be mentioned as examples of fields of application.
  • a protein deficiency soon oc ⁇ curs, for which reason most people find it necessary to discontinue the diet.
  • This protein deficiency can be compensated for by using the present protein composi ⁇ tion.
  • those applications first mentioned are by far the most important ones.
  • a protein composition treatment before and after a surgical operation can reduce the subsequent complications from approx. 30% to approx. 10%, which obviously is of great importance for the patients, but also affects the economy of the hospi ⁇ tal sector positively.
  • Another aspect of the protein composition is its high content of glutamic acid which highly affects the intestinal function.
  • the tablet thus contains approx. 17.7% glutamic acid, cf. the analysis result.
  • the invention thus provides an exceptionally valu ⁇ able protein composition for human and veterinary uses based on accessible basic ingredients.
  • Methio- Methio- Methio- Tryp- Methio ⁇ nine nine nine tophane nine Trypto- lysine, iso-leucine phane iso-leucine tryptophane
  • NUTRIO P-PRO 2000 is a high functional protein isolate based on peas.
  • the product has a neutral flavour and colour which in combination with its excellent fat binding and good absorption capacities renders its application in a large number of nutrients possible.
  • Organoleptic A white to cream powder having neutral odour and flavour.
  • LACPRODAN-80 ( from Danmark Protein A/S)
  • LACPRODAN-80 is an undenatured whey protein concentrate (WPC) produced from whey by ultraf iltration and spray-drying.
  • MIPRODAN 20-0 Sodium Caseinate Fresh Curd is a spray-dried pure milk protein manufactured from fresh pasteurized skimmed milk by acid precipitation of the casein, neutralization and spray-drying.
  • MIPRODAN 20-0 Fresh Curd Sodium Caseinate is used as a protein source and functional ingredient in a wide range of food products. It has excellent emulsifying and water holding capacities which contribute to the stabilization of many formulations.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Zoology (AREA)
  • Veterinary Medicine (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nutrition Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Marine Sciences & Fisheries (AREA)
  • Botany (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)

Abstract

A protein composition containing the following three substances: a) Nutrio P-PRO 2000 (brand name) or a similar substance having a corresponding protein composition, b) Lacprodan-80 (brand name) or a similar substance having a corresponding protein composition and c) Miprodan 20-0 (brand name) or a similar substance having a corresponding protein composition, Nutrio P-PRO 2000 being present in a smaller quantity than each one individually of Lacprodan-80 and Miprodan 20-0, the latter being present in the same or almost the same quantity, preferably in the mutual mixture proportion 20:40:40. The composition has an extraordinary high biological value and can be formed into tablets using common tablet forming ingredients. Furthermore the composition has a high content of glutamic acid, furthering the function of the bowels.

Description

PROTEIN PREPARATION CONTAINING THE ESSENTIAL AMINO ACIDS
The invention relates to a protein composition.
Proteins, also named albumin, have many functions in the human organism and control almost all body pro¬ cesses. Proteins are sine qua non. They are a major constituent of all cells, organs and organ systems. They start reactions and control them. The so-called enzymes, hormones and proteins constitute the structural basis for all tissue, connective tissue and muscular tissue, transporting essential substances in the body, e.g. oxygen, and creating the so-called antibodies, the pro¬ tective substances of the body.
They appear in an infinite number of forms, but they are all constituted of individual components, amino acids, like the letters of the alphabet. The body con¬ tains approx. 20 different amino acids that are bound together in various manners. However, of all these amino acids, only nine are sine qua non because they must necessarily be supplied to the body from an external source. The body itself can produce the others from these nine amino acids. But if a single amino acid in the link is absent, thei protein cannot be formed.
A constant catabolism of proteins takes place, but despite a certain amount of this is being recycled for regeneration, a deficiency occurs which must be recom- pensated for daily. In normal circumstances approximate¬ ly 1 gram per kilo body weight per 24 hours.
The nine vital amino acids must be supplied in a certain amount and at a certain mutual ratio. If one of these sine qua non amino acids is only supplied in e.g. approx. 50% of the necessary quantity the utilization of the other amino acids will likewise be reduced to approx. 50%. The remainder is wasted and must be ex- creted in the kidney and in adverse conditions this may be detrimental to the kidneys. Consequently the correct composition of the supplied protein, a so-called high biological value is of the utmost importance. Cf. the article "Danish scientist finds new formula for the quality of protein" in the journal økonomaen No. 9-1976 publishing Inge Lise Mørup's research results concerning the biological value of proteins.
A protein deficiency can manifest itself in numer¬ ous manners. Some of the major symptoms are lassitude, myomalacia and a low resistance to infections.
This is noticed in various groups of patients, where the protein deficiency can be very large, even exceptionally large such as in surgical patients and patients suffering from prolonged medical diseases, cancer patients and old people having a reduced inges- tion. The result is increased infirmity, a higher rate of mortality and an increased risk of infections and deficient healing.
The attached diagrams and tables illustrate these facts in which the graph of Fig. 1 proves a higher rate of mortality when a protein deficiency is the issue. Fig. 2 illustrates the relationship between the state of nutrition and sepsis upon surgical operations. An in¬ ferior state of nutrition thus results in an increased risk of sepsis. Fig. 3 shows a table of deficiencies in protein and muscular tissue in various kinds and states of ailments. Fig. 4 shows FAO's ideal aminogram and contents of various nutrients. As is illustrated all nutrients suffer from limitations when compared to the ideal that has been set.
The object of the present invention has been to provide a protein composition for human and veterinary uses containing the nine sine qua non proteins in a mutual relation as close to the uptimum as possible. This is achieved by a protein preparation according to the invention having the following composition:-
Nutrio P-PRO 2000 (brand name) or a similar sub¬ stance having a corresponding protein composition, Lacprodan-80 (brand name) or a similar substance having a corresponding protein composition and Miprodan 20-0 (brand name) or a similar substance having a correspond¬ ing protein composition, and Nutrio P-PRO 2000 is pre¬ sent in a smaller quantity than each one individually of Lacprodan-80 and Miprodan 20-0, as the latter is present in the same or almost the same quantity preferably at the mutual ratio of 1:2:2: The chemical and physical specifications of the three substances are stated in Figs. 5, 6 and 7. Fig. 8 illustrates the composition of the nine sine qua non proteins for different mixture proportions of Nutrio, Lacprodan-80 and Miprodan 20-0. As will be seen the highest biological value is estab¬ lished at a mutual mixture proportion of 20/40/40. Here the limiting amino acid is thyroxine. The biological value is as high as 0.81, which in fact is exceptionally high.
Despite the caseinate causing great problems during forming of the composition into tablet form, it has - all the same - turned out to succeed using common tablet forming ingredients and even proving to have a very satisfactory result. The tablet is odourless and without flavour, though having a trace of a milky taste when being chewed for an excessive period of time. The tablet is firm to the tooth as well as being easy and pleasant to chew. In the attached Fig. 9 the analysis result with its associated amino acid composition of a tablet is stated and Fig. 10 is a table showing the calculated biological value of the nine sine qua non proteins.
In the attached Fig. 11 is given an example of preparation of the tablets.
Surgical patients, prolonged invalids (dialyses patients), cancer patients, old people, people in nurs- ing homes, athletes, emaciation, in other words in gen¬ eral people suffering from a protein deficiency can be mentioned as examples of fields of application. In a number of slimming diets a protein deficiency soon oc¬ curs, for which reason most people find it necessary to discontinue the diet. This protein deficiency can be compensated for by using the present protein composi¬ tion. However, those applications first mentioned are by far the most important ones. A protein composition treatment before and after a surgical operation can reduce the subsequent complications from approx. 30% to approx. 10%, which obviously is of great importance for the patients, but also affects the economy of the hospi¬ tal sector positively.
Another aspect of the protein composition is its high content of glutamic acid which highly affects the intestinal function. The tablet thus contains approx. 17.7% glutamic acid, cf. the analysis result.
The invention thus provides an exceptionally valu¬ able protein composition for human and veterinary uses based on accessible basic ingredients.
Nitrogen deficiency in various states of pathoqenesis
State Nitrogen g/day Muscle tissue g/d
After one night's fasting approx. 13 325
Fasting for 72 hours 7-11 175-275
Fasting for 28 days approx. 4 100
Postoperative states a. without complications 11-18 275-450 b. with complications 18-25 450-625
Other hypercatabole states
Burns approx. 30 750
Fractures approx. 14 350
States of infection approx. 18-30 450-750
FAO's ideal Meat Fish Milk Rye Potatoes aminogram daily vital supply mg mg mg mg mg mg
Amino acids per g protein per g p, per g p. per g p, per g p. per g p,
46 46 44 34 38 50 62 58 48 47 40 41 33 34 13 80 77 96 62 60 48 48 47 35 38 89 92 78 34 48 44 40 54 45 40 11 34 14 12 10
Methio- Methio- Methio- Tryp- Methio¬ nine nine nine tophane nine
Figure imgf000008_0001
Trypto- lysine, iso-leucine phane iso-leucine tryptophane
NUTRIO P-PRO 2000 (From DDS Nutrio) Pea protein
Description: NUTRIO P-PRO 2000 is a high functional protein isolate based on peas. The product has a neutral flavour and colour which in combination with its excellent fat binding and good absorption capacities renders its application in a large number of nutrients possible.
Typical analysis: 8.0?
Minerals:
Heavy metals:
pH (10% suspension) NSI
Figure imgf000009_0001
Figure imgf000009_0002
Physical description: A free-flowing, low-dusting, easily dispersing powder.
Organoleptic: A white to cream powder having neutral odour and flavour. LACPRODAN-80 ( from Danmark Protein A/S)
Description
LACPRODAN-80 is an undenatured whey protein concentrate (WPC) produced from whey by ultraf iltration and spray-drying.
Chemical specification
Figure imgf000010_0001
pH (10% solution)
Scorched particles
Solubility index
Bulk density
Colour
Flavour and odour
Figure imgf000010_0002
Microbiological specification
Total plate count max. 50,000/g
Coliform neg in 0.10 g
Mould/Yeast neg in 0.10 g
Staphylococcus Aureus Coagulase positive neg in 1.00 g
Salmonella neg in 100 g
Properties
- High nutritional value
- High solubility in the pH-range 2-10
- High solubility at salt concentration up to 20%
- Low viscosity of solution
- Good emulsifying ability
- Heat gelation MIPRODAN 20-0 Sodium Caseinate Fresh Curd (From MD Foods, Butter and Protein Division)
Product Description
MIPRODAN 20-0 Sodium Caseinate Fresh Curd is a spray-dried pure milk protein manufactured from fresh pasteurized skimmed milk by acid precipitation of the casein, neutralization and spray-drying.
Physical Characteristics
Colour: White Flavour: Bland Sediment: A
Typical Analyses
Protein (dry basis) : 94.9%
Moisture: 5.5%
Fat: 1.0%
Lactose: 0.2%
Ash: 3.6% pH (5% solution) 6.9
Sodium Na: 1.3%
Calcium Ca: 0.06%
Lead Pb: < 1 ppm
Copper Cu: < 3 ppm
Iron Fe: <20 ppm
Arsenic As: < 1 ppm
Standard plate count: 600/g Aerobic spore count: <100/g Anaerobic spore count: <100/g Sulphite reducing clostridia: < ιo/g Coliforms: < ιo/g Mould/yeast: < ιo/g Salmonella/50g: absent Staphylococcus (coag.pos.)/g: absent
Antibiotics: absent Pesticides: absent
Application
MIPRODAN 20-0 Fresh Curd Sodium Caseinate is used as a protein source and functional ingredient in a wide range of food products. It has excellent emulsifying and water holding capacities which contribute to the stabilization of many formulations.
Cont.... SODIUM CASEINATE
Typical Amino Acid Content g per 100 g product
Aspartic acid 6.0
Threonine 3.6
Serine 5.2
Glutamic acid 18.5
Proline 8.6
Glycine 1.6
Alanine 2.6
Valine 6.
Isoleucine 4.
Leucine 8.
Tyrosine 4.
Phenylalanine 4.
Histidine 2.
Lysine 6.
Arginine 3.
Cystine 0.5
Methionine 2.4
Tryptophane 1.2
Mixture proportion:
Nutrio P-PRO 2000/ Lacprodan-80/ Miprodan 20-0
Figure imgf000012_0001
Analysis result:
Contents per 100 g
Protein (NMKL 6 Nx6.25) Fat (NMKL 88./Q481) Carbohydrate as difference Ash (NMKL modif./Q499) Water (NMKL modif./Q499)
Energy
Net weight (NMKL 55 1980)
Figure imgf000013_0001
*Amino acid composition
Aspartic acid
Threonine
Serine
Glutamic acid
Proline
Glycine
Alanine
Isoleucine
Leucine
Tyrosine
Phenylalanine
Lysine
Histidine
Arginine
Cystine
Methionine
Tryptophane
Valine
Figure imgf000013_0002
(Analysis effected by Quist's Laboratorium A/S) weight accord- AxlOOO Eggs biological ing to analysis 340.9 value B shown in Fig.9 C
B D
leucine 65.4 191.845 179 1.07
isoleucine 40.1 117.63 110 1.06
lysine 57.9 169.84 141 1.20
fenylalanine 30.
thyrosine 29.
Figure imgf000014_0001
methionine
cystine
Figure imgf000014_0002
threonine 36.0 105.6 99 1.07
tryptophane 10.0 29.33 30 0.98
valine 45.1 132.3 140 0.95
total 340.9
tablet weight 760.6 mg protein per tablet 499.7 mg sine qua non amino acids 340.9 mg = 44.8' glutamic acid 135.0 mg = 17.7% Example of preparing tablets:
Protein:
Nutrio P-PRO 2000 Lacprodan - 80 Miprodan 20-0
Figure imgf000015_0001
Common tablet additives:
Silicium dioxide 0.900 kg
Cellulosum, microcryst. 14.000 kg
Potato starch 10.500 kg
Saccharum 6.000 kg
Talcum 4.000 kg
Magnesiumstearate 0.600 kg
Alle ingredients except magnesiumstearate are mixed in the cone for 20 minutes upon which magnesiumstearate is admixed for a maximum of five minutes, it may be sieved. Tablet forming: 12 mm slightly convex. Tablet weight: 720 mg (685-755 mg) .

Claims

C L A I M S :
1. A protein composition, characterized in that it contains Nutrio P-PRO 2000 (brand name) or a similar substance having a corresponding protein composition, Lacprodan-80 (brand name) or a similar substance having a corresponding protein composition and Miprodan 20-0 (brand name) or a similar substance having a correspond¬ ing protein composition, and Nutrio P-PRO 2000 is present in a smaller quantity than each one individually of Lacprodan-80 and Miprodan 20-0, as the latter is present in the same or almost the same quantity.
2. A protein composition according to claim 1, characterized in that it contains the three substances Nutrio P-PRO 2000, Lacprodan-80 and Miprodan 20-0 in the ratio of 1:2:2 or approximately this ratio.
3. A protein composition according to claim 1, characterized by it containing glutamic acid.
4. A protein composition according to claims 1, 2 or 3, characterized in that it has been formed into tablets using conventional tablet forming ingredients.
5. A protein composition according to claim 4, characterized in that it contains the following tablet forming ingredients: silicium dioxide, cellulosium, potato starch, saccharium, talc and magnesium stearat.
PCT/DK1992/000249 1991-08-22 1992-08-24 Protein preparation containing the essential amino acids WO1993003754A1 (en)

Applications Claiming Priority (2)

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DK1495/91 1991-08-22
DK149591A DK149591A (en) 1991-08-22 1991-08-22 protein preparation

Publications (1)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8815797B2 (en) 2008-03-12 2014-08-26 N.V. Nutricia High protein liquid enteral nutritional composition
US8999423B2 (en) 2007-12-05 2015-04-07 N. V. Nutricia High energy liquid enteral nutritional composition

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2066644A (en) * 1979-12-21 1981-07-15 Rhone Poulenc Ind Food products based on protein fibres, and process and equipment for their manufacture
EP0374390A1 (en) * 1988-12-23 1990-06-27 Immunotech Research Corporation Ltd. Whey protein composition, a method for producing it and application of the whey protein composition

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2066644A (en) * 1979-12-21 1981-07-15 Rhone Poulenc Ind Food products based on protein fibres, and process and equipment for their manufacture
EP0374390A1 (en) * 1988-12-23 1990-06-27 Immunotech Research Corporation Ltd. Whey protein composition, a method for producing it and application of the whey protein composition

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
DIALOG INFORMATION SERVICES, File 351, WPIL Dialog Accession No. 009089297, ASAFOV V.A. et al.: "Mfr. of Dried Protein Material for Use in Dairy Foodstuffs, etc. - by Condensing Whey or Permeate, Adding Protein Material and Dispersing"; & WO,A,92 09207, 11-06-92, 9226. *
DIALOG INFORMATION SERVICES, File 51, FSTA, Dialog Accession No. 00394145, MADSEN J: "Rea Protein in Low Fat Spread"; & RESEARCH DISCLOSURE, 1989, No. 299, p. 179-180. *
PATENT ABSTRACTS OF JAPAN, Vol. 8, No. 15, C-206; & JP,A,58 180 429, 21-10-1983. *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8999423B2 (en) 2007-12-05 2015-04-07 N. V. Nutricia High energy liquid enteral nutritional composition
US9345256B2 (en) 2007-12-05 2016-05-24 N.V. Nutricia High energy liquid enteral nutritional composition
US8815797B2 (en) 2008-03-12 2014-08-26 N.V. Nutricia High protein liquid enteral nutritional composition
US9420816B2 (en) 2008-03-12 2016-08-23 N.V. Nutricia High protein liquid enteral nutritional composition

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