NZ753628B2 - Pufa salt formulations (i) - Google Patents

Pufa salt formulations (i) Download PDF

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Publication number
NZ753628B2
NZ753628B2 NZ753628A NZ75362817A NZ753628B2 NZ 753628 B2 NZ753628 B2 NZ 753628B2 NZ 753628 A NZ753628 A NZ 753628A NZ 75362817 A NZ75362817 A NZ 75362817A NZ 753628 B2 NZ753628 B2 NZ 753628B2
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New Zealand
Prior art keywords
solid formulation
pufa
solid
acid
particulate
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NZ753628A
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NZ753628A (en
Inventor
Elger Funda
Denis Hug
Odile Krainz
Sean Mcdonnel
Shalla Ramnarain
Casey Sumner
Jenny Tang
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Dsm Ip Assets Bv
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Priority claimed from PCT/EP2017/082551 external-priority patent/WO2018108975A1/en
Publication of NZ753628A publication Critical patent/NZ753628A/en
Publication of NZ753628B2 publication Critical patent/NZ753628B2/en

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K10/00—Animal feeding-stuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/18—Peptides; Protein hydrolysates
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/17—Amino acids, peptides or proteins
    • A23L33/19—Dairy proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
    • A23P10/00—Shaping or working of foodstuffs characterised by the products
    • A23P10/30—Encapsulation of particles, e.g. foodstuff additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/20—Ingredients acting on or related to the structure
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/20—Ingredients acting on or related to the structure
    • A23V2200/224—Encapsulating agent
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/30—Foods, ingredients or supplements having a functional effect on health
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/186—Fatty acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/186—Fatty acids
    • A23V2250/1862—Arachidonic acid
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/186—Fatty acids
    • A23V2250/1868—Docosahexaenoic acid
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/186—Fatty acids
    • A23V2250/187—Eicosapentaenoic acid
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/186—Fatty acids
    • A23V2250/1872—Linoleic acid
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/186—Fatty acids
    • A23V2250/1874—Linolenic acid
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/18—Lipids
    • A23V2250/186—Fatty acids
    • A23V2250/1882—Polyunsaturated fatty acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/54—Proteins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/54—Proteins
    • A23V2250/542—Animal Protein
    • A23V2250/5424—Dairy protein
    • A23V2250/54246—Casein
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/54—Proteins
    • A23V2250/55—Peptide, protein hydrolysate
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2300/00—Processes
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2300/00—Processes
    • A23V2300/10—Drying, dehydrating
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2300/00—Processes
    • A23V2300/31—Mechanical treatment
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
    • A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
    • A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
    • A61K9/1605—Excipients; Inactive ingredients
    • A61K9/1629—Organic macromolecular compounds
    • A61K9/1658—Proteins, e.g. albumin, gelatin

Abstract

The present patent application relates to polyunsaturated fatty acid salt (PUFA salts) solid formulations further comprising at least one casein phosphopeptide, for use in food products, dietary supplements or pharmaceutical products, having reduced undesirable smells and tastes.

Description

PUFA SALT FORMULATIONS (I) The present patent ation relates to novel polyunsaturated fatty acid salt (PUFA salts) solid formulations.
Polyunsaturated fatty acids (PUFAs) are very well-known compounds for a healthy diet (especially the omega-3 fatty acids). The PUFAs (especially the omega-3 fatty acids) have variety of health ts against for example cardiovascular diseases (CVDs) including well-established hypotriglyceridemic and against nflamma- tory s. ore, PUFAs are important ients in a healthy diet (for animals and humans PUFAs can be found in a variety of plants and animal in various quantities and in various mixtures (of the different PUFA).
A very good source of omega-3 fatty acids are for example fish.
However, it is also possible to produce PUFAs synthetically.
Since many consumers do not like fish, especially the smell and taste of it, (or other PUFA containing sources), it is very common to add PUFAs to other dietary products (enrich these products with PUFA) to enable the desired healthy diet.
The problem of the PUFAs is, that they have strong tendency to oxidise. This results in a loss of the PUFAs in the product and ly (even worse) in the development of a strong and very unpleasant smell.
With increasing number of double bonds, the PUFAs are subject to increasing oxidative degradation and development of undesirable “off-flavours”, mainly fishy and rancid smell and taste. Volatile degradation ts cause off-flavour even at very low concentration. Sensory properties of a product may become unacceptable even before a loss of PUFAs can be detected analytically.
Another issue arises e PUFAs are oils compounds and therefore the incorporation of PUFA is not so easy and usually needs an emulsification step.
Now it was found that when PUFA salts (usually Na, K, or Ca salts) are used instead of PUFA very stable and easy to handle solid formulations are obtained.
By the term “solid ation”, it is meant that the formulation is in form. It is usually in the form of a powder, granule or beadlets. These formulations differ in the size of their particles.
Surprisingly it was found out that when at least one PUFA salt is ed in a matrix comprising a casein phosphopeptide (CPP) a very stable solid formulation is obtained.
Therefore, the present invention relates to a solid formulation (SF) comprising (i) at least one PUFA salt, and (ii) a casein phosphopeptide.
The present invention also relates to a particulate solid ation sing: (i) at least one polyunsaturated fatty acid (PUFA) salt, and (ii)10-75 wt.% of a casein phosphopeptide.
The present invention also relates to a s for production of the particulate solid formulation claim 1, wherein the process comprises: (i) dry mixing water soluble matrix ingredients to form a dry matrix mix, (i) (ii) dissolving the dry matrix mix in water to form an aqueous matrix solution; (ii) (iii)adding the at least one PUFA salt to the aqueous matrix solution to form an aqueous mixture of the at least on PUFA salt and the matrix solution ; and thereafter (iv) spray drying the aqueous mixture of the at least on PUFA salt and the matrix solution to form the particles of the solid formulation.
As stated above the solid formulation can have various particles sizes.
When the solid formulation is a spray dried powder form the red average particle size of the solid formulation is 10 – 200 mm.
When the solid formulation is a beadlet, the preferred average particle size of the beadlet is 200 – 1000 mm.
When the solid formulation is a granule/pellet the red average particle size of the granule/pellet is preferably below 1000 mm.
The le size is determined by using well-known methods, such as (scanning) electron copy. The particle size in the context of the present invention is defined as the longest dimension of a particle (such i.e. the diameter in case of spher- ical particle).
All particle sizes are determined by laser diffraction technique using a "Mastersizer 3000" of Malvern Instruments Ltd., UK. Further information on this particle size characterization method can e.g. be found in "Basic principles of particle size analytics" , Dr. Alan Rawle, Malvern Instruments Limited, Enigma ss Part, ood Road, Malvern, Worcestershire, WR14 1XZ, UK and the "Manual of Malvern particle size er". Particular reference is made to the user manual number MAN 0096, Issue 1.0, Nov. 1994. If nothing else is stated all particle sizes ing are Dv50 values (volume diameter, 50% of the population resides below this point, and 50% resides above this point) determined by laser diffraction. The particle size can be determined in the dry form. ore, the present invention relates to a solid formulation (SF1) comprising (i) at least one PUFA salt, and (ii) a casein phosphopeptide, wherein the average particle size is 10 – 200 mm.
Therefore, the present invention relates to a solid formulation (SF1’) comprising (i) at least one PUFA salt, and (ii) a casein phosphopeptide, wherein the average particle size is 200 – 1000 mm.
Therefore the t invention relates to a solid formulation (SF1’’) comprising (i) at least one PUFA salt, and (ii) a casein phosphopeptide, wherein the average particle size is above 1000 mm.
The PUFAs are classified according to the position of the double bonds in the carbon chain of the molecule as n-9, n-6 or n-3 PUFAs. Examples of n-6 PUFAs are linoleic acid (C18 : 2), arachidonic acid (C20 : 4), γ-linolenic acid (GLA, C18 : 13) and - γ -linolenic acid (DGLA, C20 : 3). Examples of n-3 PUFAs are α-linolenic acid (C18 : 13), eicosapentaenoic acid (EPA, C20 : 5), and hexaenoic acid (DHA, C22 : 6). Especially EPA and DHA have attracted interest of the food industry in recent years. The most available sources of these two fatty acids are fish and the marine oils extracted from them. Suitable PUFA salts are the sodium, potassium , magnesium and/or calcium salts. Mixed salts are also suitable.
Very suitable PUFA oils are commercially available for example from DSM Nutri- tional Products Ltd. These suitable PUFA oils are MEG-3® 4020 EE Oil, MEG-3® 4030 EE Oil, MEG-3® 4421 EE Oil and MEG-3® 5020 EE Oil, which are then transformed into the salts.
Therefore, the present invention relates to a solid formulation (SF2), which is solid formulation (SF), (SF1), (SF1’) or (SF1’’), wherein the PUFA salts are the sodium, potassium, magnesium and/or calcium salts. ore, the present invention relates to a solid formulation (SF3), which is solid ation (SF), (SF1), (SF1’), (SF1’’) or (SF2), wherein the PUFA salts are chosen from the group consisting of linoleic acid, arachidonic acid, γ-linolenic acid, dihomo- γ enic acid, α-linolenic acid, eicosapentaenoic acid, and docosahexaenoic acid in form of its sodium, potassium and/or calcium salts. The most ble sources of these two fatty acids are fish and the marine oils extracted from them. Suitable PUFA salts are the sodium, potassium, magnesium and/or calcium salts. Mixed salts are also suitable.
The content of the PUFA salts can vary and it is usually at least 5 weight-% , based on the total weight of the solid formulation.
Usually the PUFA salt (or mixture of PUFA salts) are present in an amount of up to 80 wt-%, based on the total weight of the solid formulation.
Preferably, the solid formulation ing to the present ion comprises 10 – 70 wt-%, based on the total weight of the solid formulation, of at least one PUFA salt.
More preferably, the solid formulation according to the present invention comprises – 60 wt-%, based on the total weight of the solid formulation, of at least one PUFA salt.
Therefore, the present ion relates to a solid formulation (SF4), which is solid formulation (SF), (SF1), (SF1’), (SF1’’), (SF2) or (SF3), wherein the solid formulation comprises 5 – 80 wt-%, based on the total weight of the solid formulation, of at least one PUFA salt.
Therefore, the present invention relates to a solid formulation (SF5), which is solid formulation (SF), (SF1), (SF1’), (SF1’’), (SF2), (SF3) or (SF4), wherein the solid formulation comprises 10 – 70 wt-%, based on the total weight of the solid formula- tion, of at least one PUFA salt.
More preferably, the solid formulation according to the present invention comprises – 80 wt-%, based on the total weight of the solid formulation, of at least one PUFA salt.
The solid formulation according to the present also ses casein phosphopeptide (CPP).
CPP is usually prepared from solubilized milk protein. It derived from the tryptic ysis of casein. The peptides were phosphoseryl rich, which could bind divalent metal. The presence of phosphate groups ating from phosphorylated serine residues in close proximity to the peptide chain creates a polar, acidic domain that is favourable for tering divalent metals such as calcium, zinc, copper, manganese and iron. The ce of an c triplet (SerP–SerP–SerP–Glu– Glu) embedded in the bioactive e is a distinctive e for all functional CPP derived from whole β-casein-4P (1–25), αs1-casein-5P (59–79), αs2-casein-4P (1– 21) and αs2-casein-4P (46–70).
CPP is also commercially available. It is available i.e. under the tradename Hyvital® Casein Phosphopeptides from FrieslandCampina Domo.
The content of the CPP salts can vary and it is usually at least 10 wt-%, based on the total weight of the solid formulation.
Usually the CPP is present in an amount of up to 75 wt-%, based on the total weight of the solid formulation.
Furthermore, the present invention relates to a solid formulation sing 10 – 75 wt-%, based on the total weight of the solid formulation, of CPP.
Furthermore, the present invention relates to a solid formulation comprising 15 – 70 wt-%, based on the total weight of the solid formulation, of CPP.
Therefore, the present invention relates to a solid formulation (SF6), which is solid formulation (SF), (SF1), (SF1’), (SF1’’), (SF2), (SF3), (SF4) or (SF5), wherein the solid formulation comprising 10 – 75 wt-%, based on the total weight of the solid formulation, of CPP. ore, the present invention relates to a solid formulation (SF7), which is solid formulation (SF), (SF1), (SF1’), (SF1’’), (SF2), (SF3), (SF4), (SF5) or (SF6), wherein the solid formulation comprising 15 – 70 wt-%, based on the total weight of the solid formulation, of CPP.
All percentage in the context of the present invention are always added up to 100 % in each solid formulation. In case the PUFA salts(s) and the CPP do not add up to 100 % there is at least one other ingredient present.
Furthermore, the solid formulation according to the present invention can also comprise further ingredients.
A preferred group of such ingredients are gums, such as xanthan gum, gum arabic, gum ghatti, agar, alginic acid, sodium te, carrageenan, gum tragacanth, karaya gum, guar gum, locust bean gum or gellan gum.
These gums can even improve further improve the stability of the solid formulations ing to the present invention.
A very preferred gum is gum Arabic.
Preferably, the solid formulation comprises up to 30 wt-%, based on the total weight of the solid formulation, of at least one gum.
More preferably, the solid formulation comprises up to 30 wt-%, based on the total weight of the solid formulation, of at least one gum chosen from the group consisting of xanthan gum, gum arabic, gum ghatti, agar, alginic acid, sodium alginate, carrageenan , gum tragacanth, karaya gum, guar gum, locust bean gum or gellan gum.
Even more ably, the solid formulation ses up to 30 wt-%, based on the total weight of the solid formulation, of gum .
Therefore, the present invention relates to a solid (SF8), which is solid formulation (SF), (SF1), , (SF1’’), (SF2), (SF3), (SF4), (SF5), (SF6) or (SF7), wherein the solid ation comprises up to 30 wt-%, based on the total weight of the solid formulation, of at least one gum.
Therefore, the present invention relates to a solid formulation (SF8’), which is solid formulation (SF8), wherein the solid formulation comprises up to 30 wt-%, based on the total weight of the solid formulation, of at least one gum chosen from the group consisting of xanthan gum, gum arabic, gum ghatti, agar, alginic acid, sodium alginate , carrageenan, gum tragacanth, karaya gum, guar gum, locust bean gum or gellan gum.
Therefore, the present invention relates to a solid formulation (SF8’’), which is solid formulation (SF8), wherein the solid formulation comprises up to 30 wt-%, based on the total weight of the solid formulation, of gum arabic.
Another preferred group of such ients are sugar alcohols (also called polyhy- dric ls, polyalcohols, alditols or glycitols).
Suitable sugar alcohols are for example ol, erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, fucitol, iditol, inositol, volemitol, isomalt, maltitol, lactitol, maltotriitol, maltotetraitol and polyglycitol.
Very preferred sugar alcohols are ol or maltitol.
Preferably, the solid ation ses up to 30 wt-%, based on the total weight of the solid formulation, of at least sugar alcohol.
More preferably, the solid formulation comprises up to 30 wt-%, based on the total weight of the solid formulation, of at least one sugar alcohol chosen from the group consisting of glycerol, erythritol, threitol, arabitol, xylitol, ribitol, mannitol, sorbitol, galactitol, l, iditol, inositol, volemitol, isomalt, maltitol, lactitol, maltotriitol, maltotetraitol and polyglycitol.
Even more preferably, the solid formulation comprises up to 30 wt-%, based on the total weight of the solid formulation, of mannitol and/or ol.
Therefore, the present invention relates to a solid (SF9), which is solid ation (SF), (SF1), (SF1’), (SF1’’), (SF2), (SF3), (SF4), (SF5), (SF6), (SF7), (SF8), (SF8’) or (SF8’’), wherein the solid formulation comprises up to 30 wt-%, based on the total weight of the solid formulation, of at least one sugar alcohol.
Therefore, the t invention relates to a solid formulation (SF9’), which is solid formulation (SF9), wherein the solid formulation comprises up to 30 wt-%, based on the total weight of the solid formulation, of at least one sugar alcohol from the group consisting of glycerol, erythritol, threitol, arabitol, l, ribitol, mannitol, sorbitol, galactitol, fucitol, , inositol, volemitol, isomalt, maltitol, lactitol, maltotriitol, maltotetraitol and polyglycitol.
Therefore, the present ion s to a solid formulation ), which is solid formulation (SF9), wherein the solid formulation comprises up to 30 wt-%, based on the total weight of the solid formulation, of mannitol and/or maltitol. rmore, the solid formulation according to the present invention can further comprise at least one auxiliary agent, wherein the auxiliary agent is chosen from the group consisting of antioxidants (such as ascorbic acid or salts thereof, tocoph- erol (synthetic or natural); butylated hydroxytoluene (BHT); butylated hydroxyanisole (BHA); propyl gallate; tert. butyl hydroxyquinoline, ascorbic acid esters of a fatty acid and/or ethoxyquin), plasticisers, stabilisers, humectants, protective ds , dyes, fragrances, fillers and buffers.
These auxiliary agents can be present in an amount of up to 30 wt-%, based on the total weight of the solid formulation.
Therefore the present invention relates to a solid (SF10), which is solid ation (SF), (SF1), (SF1’), ), (SF2), (SF3), (SF4), (SF5), (SF6), (SF7), (SF8), (SF8’), (SF8’’), (SF9), (SF9’) or (SF9’’), wherein the solid formulation comprises at least one auxiliary agent, wherein the auxiliary agent is chosen from the group consisting of antioxidants (such as ascorbic acid or salts thereof, tocopherol (synthetic or natural ); butylated ytoluene (BHT); butylated hydroxyani-sole (BHA); propyl gallate ; tert. butyl hydroxyquinoline, ascorbic acid esters of a fatty acid and/or ethox- yquin), plasticisers, stabilisers, ants, protective colloids, dyes, fragrances, fillers and buffers.
Therefore, the present invention relates to a solid (SF10’), which is solid formulation (SF10), wherein the solid ation comprises up to 30 wt-%, based on the total weight of the solid formulation of at least one auxiliary agent.
The shape of the particles of the solid formulation according to the present ion is not an essential feature of the present invention. The shape can be sphere-like or any other form (also mixtures of shapes). Usually and preferably, the particles are sphere-like.
One of the main advantages of the solid formulations according to the present invention also lies in the tion of the solid ation.
No emulsification step is needed.
All ingredients are dissolved in water and then usually spray dried. Other drying techniques like spray granulation or beadlet process may be applied as well.
The process of production of the solid ation is usually the following (i) the soluble ingredients of the matrix are mixed in their dry form and then dissolved in water; afterwards (ii) the PUFA salt is added, afterwards (iii) the mixture is (spray) dried.
It is also possible that all water-soluble ingredients are solved in water (and not mixed in dry form).
Depending on the temperature of the spray drying s, the solid ation can still comprise water (usually not more than 5 wt-%, based on the total weight of the solid formulation).
The solid formulation (SF), (SF1), (SF1’), (SF1’’), (SF2), (SF3), (SF4), (SF5), (SF6), (SF7), (SF8), (SF8’), (SF8’’), (SF9), (SF9’), (SF9’’), (SF10) or (SF10’) can also be used as such or used to be incorporated into other product forms.
The solid formulation can be incorporated into food, feed, pharmaceutical and/or personal care products.
The solid formulation can be also being incorporated into a premix. This premix is then incorporated into a food, feed, pharmaceutical and/or personal care product.
Another ment of the present invention is the use of at least one casein phos- phopeptide for manufacturing a solid formulation comprising at least one PUFA salt.
The solid ation according to the present invention can also be used in pharmaceutical products. The pharmaceutical t can be in any galenical form, usually in the form of tablets.
A further embodiment of the present invention relates to food products, feed products , dietary supplements, and/or pharmaceutical products, comprising at least one solid formulation (SF), (SF1), (SF1’), (SF1’’), (SF2), (SF3), (SF4), (SF5), (SF6), (SF7), (SF8), (SF8’), (SF8’’), (SF9), (SF9’), (SF9’’), (SF10) and/or ).
The ion is illustrated by the following Examples. All atures are given in °C and all parts and percentages are related to the weight.
General All the solid formulations, which were tested, are produced using the procedure described in Example 1. The ingredients and/or their concentration vary, not the process parameters.
The salts (Na or K) of the following commercially available PUFA oils (available from DSM Nutritional Products Ltd) have been used · MEG-3® 4020 EE Oil (This s a marine omega-3 long chain polyunsaturated fatty acid. This ethyl ester has a minimum of 360mg EPA, 180mg DHA, and 590mg total 3 per gram).
· MEG-3® 4030 EE Oil (this is a marine omega-3 long chain polyunsaturated fatty acid. This ethyl ester has a minimum of 360mg EPA, 270mg DHA, and 680mg total Omega-3 per gram.) · MEG-3® 4421 EE Oil is a marine omega-3 long chain polyunsaturated fatty acid. This ethyl ester has a minimum of 400mg EPA, 200mg DHA, and 650mg total Omega-3 per gram.
· MEG-3® 5020 EE Oil is a marine omega-3 long chain polyunsaturated fatty acid. This ethyl ester has a minimum of 460mg EPA, 180mg DHA, and 700mg total Omega-3 per gram Example 1: g of maltodextrin dextrin 28 – 31), 20 g of sodium ascorbate and 80 g of casein phosphopeptide (Hyvital® Casein Phosphopetide from FrieslandCampina Domo) were put (in their dry state) into a beaker and mixed well. ard 800 g of water were added slowly to this mixture under constant ng.
This solution was heated up to 50°C, and adjust the pH was adjusted (by NaOH or KOH) to 8.5.
The PUFA salt (the Na salt of MEG-3® 4030 EE Oil) was also heated up to 50°C and then the warm PUFA salt was added to the aqueous solution. A slurry way obtained.
The so obtained slurry was spray dried (using a GEA MOBILE MINOR™), inlet temperature was set at 150~180°C, outlet temperature was controlled around 60~80°C.
A free-flowing powder was obtained.
Testing of the solid ations The storage stability of the produced solid formulations was tested as follows: The solid formulations were stored at room temperature and after defined storage times the ations were evaluated by a sensory panel of experienced and welltrained persons.
Each person of this panel sniffed at the solid formulations and gave them a value of the sensory scale.
This sensory scale, which was applied, has values that goes from 0 to 15. 0 means no smell 15 means extremely strong.
The following itions are tested (the amount of the ients is given in gram (g)): Table 1: Formulations (1 – 4). The formulation 1 is the one produced as in Example 1. The forms 2 – 4 are comparative examples produced according to the method of example 1.
Ingredients Form 1 Form 2 Form 3 Form 4 PUFA Na Salt of MEG-3® 250 250 250 250 4030 EE Oil Maltodextrin 28-31 25 25 25 25 Sodium Ascorbate 15 15 15 15 Casein Phosphopeptide 80 Gelatin Rousselot 175 80 Whey Protein Concen- 80 trate Egg Yolk 80 Water 1000 1000 1000 1000 Form 1 is the inventive formulation. The Forms 2, 3, and 4 are comparative examples using other (commonly used) matrix materials Sensory Results: Table 2: the y results of the forms 1 – 4 Fishy Ma- Other off rine Complex FORM 1 initial - - 4 weeks - - 8 weeks - - 12 weeks 1.0 - 16 weeks - - weeks - - FORM 2 initial 4.0 4 weeks 4.0 8 weeks 5.0 FORM 3 initial 2.5 4 weeks 3.0 8 weeks 3.0 FORM 4 initial 5.0 4 weeks 2.0 8 weeks 3.0 The formulations using other matrix materials are showing an unpleasant smell (“fishy smell”) right from the start! Formulations 5 and 6: The formulations are produced in accordance with the process as disclosed in Example Table 3: formulations 5 and 6 Ingredients Form 5 Form 6 PUFA K Salt of MEG-3® 4421 250 EE Oil Maltodextrin 28-31 25 25 Sodium Ascorbate 20 20 Casein opeptide 80 50 TIC Pretested® Gum Arabic Spray Dry Powder – Grade #1 30 Water 1000 1000 These two forms (Form 5 and Form 6) are solid formulations according to the invention.
Sensory Results Table 4: sensory results of formulations 5 and 6 Fishy Marine Other Off Complex FORM 5 initial 1.0 4 weeks 0.5 8 weeks 2 12 weeks 16 weeks weeks 1 24 weeks 36 weeks 0.8 FORM 6 initial 4 weeks 0.5 8 weeks 12 weeks 16 weeks 1 weeks 1.0 1 24 weeks 2.0 36 weeks 1.5 Formulations 7 and 8: Table 5: formulations 7 and 8 Ingredient Form 7 Form 8 PUFA Na Salt of MEG-3® 4421 250 250 EE Oil extrin 28-31 25 25 Sodium Ascorbate 20 20 Casein Phosphopeptide 25 25 TIC Pretested® Gum Arabic 30 30 Spray Dry Powder – Grade #1 Mannitol 25 Maltitol 25 Water 1000 1000 Sensory Results Table 6: sensory results of formulations 7 and 8 Fishy Marine Complex Other Off Form 7 initial 1 4 weeks 1.3 8 weeks 12 weeks 0.8 16 weeks 2.0 weeks 1.5 1.5 Form 8 initial 4 weeks 8 weeks 12 weeks 2.0 16 weeks weeks 24 weeks 36 weeks It can be seen from these evaluation tests that the solid formulations according to the present invention are better significantly than such, which are produced with a different nly and widely used) matrix material.

Claims (15)

Claims
1. A particulate solid formulation comprising: (i) at least one polyunsaturated fatty acid (PUFA) salt, and 5 (ii) 10-75 wt.% of a casein phosphopeptide.
2. The particulate solid formulation according to claim 1, wherein particles of the solid formulation have an average particle size Dv50 of 10 – 200 µm. 10
3. The particulate solid formulation according to claim 1, wherein particles of the solid formulation have an average particle size Dv50 of 200 – 1000 µm.
4. The particulate solid ation according to claim 1, n particles of the solid formulation have an average le size Dv50 of more than 1000 µm.
5. The particulate solid formulation according to claim 1, wherein the PUFA salt ses at least one PUFA salt selected from the group consisting of PUFA sodium salts, PUFA potassium salts, PUFA magnesium salts and PUFA calcium salts.
6. The particulate solid formulation according to claim 1, wherein the at least one PUFA salt is selected from the group consisting of sodium, potassium and/or calcium salts of linoleic acid, donic acid, γ-linolenic acid, dihomo- γ - linolenic acid, α-linolenic acid, eicosapentaenoic acid, and docosahexaenoic 25 acid.
7. The particulate solid formulation according to claim 1, wherein the solid ation comprises 5 – 80 wt.%, based on total weight of the solid formulation, of the at least one PUFA salt.
8. The particulate solid formulation according to claim 1, n the solid formulation comprises up to 30 wt.%, based on total weight of the solid formulation, of at least one gum. 5
9. The particulate solid formulation according to cl aim 1, wherein the solid formulation comprises up to 30 wt.%, based on total weight of the solid formulation, of at least one sugar alcohol.
10. . The particulate solid formulation according to cl aim 1, wherein the solid for- 10 mulation comprises at least one auxiliary agent ed from the group consisting of antioxidants, plasticisers, stabilisers, humectants, protective colloids , dyes, fragrances, fillers and buffers.
11. . The particulate solid formulation according to cl aim 11, wherein the antioxidant is at least one selected from the groups consisting of ic acid or salts 15 thereof, tic tocopherol, natural tocopherol, butylated hydroxytoluene, butylated hydroxyanisole, propyl gallate; tert. butyl hydroxyquinoline and ascorbic acid esters of a fatty acid and ethoxyquin.
12. The particulate solid formulation according to claim 11, wherein the humectant 20 is at least one selected from the group consisting of ine, sorbitol and polyethylene glycol.
13. . A process for production of the particulate solid formulation claim 1, n the process comprises: 25 (i) dry mixing water soluble matrix ingredients to form a dry matrix mix, (ii) dissolving the dry matrix mix in water to form an aqueous matrix solution (iii) adding the at least one PUFA salt to the aqueous matrix solution to form an aqueous mixture of the at least on PUFA salt and the matrix 30 on; and thereafter (iv) spray drying the aqueous mixture of the at least on PUFA salt and the matrix solution to form the particles of the solid formulation.
14. Food products, feed products, dietary ments, pharmaceutical products 5 and/or premixes, comprising the at least one solid formulation according to claim 1.
15. Use of at least one casein phosphopeptide for manufacturing a solid particulate formulation comprising at least one PUFA salt, n the solid particu- 10 late formulation further comprises 10 – 75 wt-%, based on the total weight of the solid particulate formulation, of casein phosphopeptide.
NZ753628A 2016-12-13 2017-12-13 Pufa salt formulations (i) NZ753628B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP16203602.4 2016-12-13
EP16203602 2016-12-13
PCT/EP2017/082551 WO2018108975A1 (en) 2016-12-13 2017-12-13 Pufa salt formulations (i)

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Publication Number Publication Date
NZ753628A NZ753628A (en) 2021-10-29
NZ753628B2 true NZ753628B2 (en) 2022-02-01

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