# US 10,117,839 B2 · Encapsulation of hydrophobic biologically active compounds

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- Number: US 10,117,839 B2
- Document ID: US10117839B2
- Status: Granted
- Kind: B2
- Application number: 14/817,307
- Filed: 2015-08-04
- Published: 2016-02-11
- Granted: 2018-11-06
- Earliest claimed: 2014-08-05
- Assignees: Intervet Inc.
- Applicants: Intervet Inc.
- Inventors: Mordechai Harel; Majid Keshtmand; Swetha Kambalapally; Sara Morrison-Rowe
- Web page: https://patentgrep.com/patent/US10117839B2

## CPC

- A61K 9/5052: {Proteins, e.g. albumin}
- A23K 20/158: Fatty acids; Fats; Products containing oils or fats
- A23K 40/30: by encapsulating; by coating
- A23L 29/212: Starch; Modified starch; Starch derivatives, e.g. esters or ethers (containing starch hydrolysates, e.g. dextrin, A23L29/30)
- A23L 29/219: Chemically modified starch; Reaction or complexation products of starch with other chemicals
- A23L 29/25: Exudates, e.g. gum arabic, gum acacia, gum karaya or tragacanth
- A23L 29/281: Proteins, e.g. gelatin or collagen
- A23L 29/284: {Gelatin; Collagen}
- A23L 33/115: Fatty acids or derivatives thereof; Fats or oils
- A23P 10/30: Encapsulation of particles, e.g. foodstuff additives
- A61K 9/1652: {Polysaccharides, e.g. alginate, cellulose derivatives; Cyclodextrin (homeopathic globules A61K9/1623)}
- A61K 9/5073: {having two or more different coatings optionally including drug-containing subcoatings}
- A61K 9/5169: {Proteins, e.g. albumin, gelatin}
- A61K 31/00: Medicinal preparations containing organic active ingredients
- A61K 31/07: Retinol compounds, e.g. vitamin A (retinoic acids A61K31/203)
- A61K 31/22: of acyclic acids, e.g. pravastatin
- A61K 35/60: Fish, e.g. seahorses; Fish eggs
- A23V 2002/00: Food compositions, function of food ingredients or processes for food or foodstuffs
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A23K: FODDER
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A23P: SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23V: INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION

## Abstract

A composition comprising hydrophobic droplets coated by a shell and dispersed in a matrix and a consumable product comprising the composition are provided. The hydrophobic droplets comprise a hydrophobic compound, the shell comprises an irreversibly denatured protein, and the matrix comprises a protein, a starch, and a polysaccharide. Also provided are methods for preparing the composition and the consumable product.

## Claims

### Claim 1

A composition comprising a hydrophobic compound in a form of coated hydrophobic droplets, wherein more than 90% of the hydrophobic droplets are coated by a shell, wherein the shell comprises an irreversibly denatured first protein, wherein the shell is covered by a polysaccharide matrix, wherein the polysaccharide matrix is covered by a polymeric matrix, and wherein the polymeric matrix comprises a starch and a second protein, and wherein the composition comprises less than 20 wt % water.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the hydrophobic compound is a bioactive agent selected from the group consisting of vitamins, antibiotics, carotenoids, plant extracts, fruit extracts, vegetable extracts, antioxidants, lipids, steroids, phytochemicals and drugs.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the irreversibly denatured first protein is prepared by applying two different external stressors, wherein each external stressor is selected from the group consisting of an acid, a base, an inorganic salt, an enzyme, an organic solvent, heat and sheer force, and a combination thereof.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the hydrophobic droplets have a particle size within the range of 0.1 μm to 5.0 μm.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the ratio between the irreversibly denatured first protein and the hydrophobic droplets is within the range of 0.1:1 to 1:1 by weight.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the second protein is a globular or randomly coiled protein.

### Claim 7 (depends on 6)

The composition of claim 6, wherein the globular or randomly coiled protein is selected from the group consisting of dairy proteins, gelatin, corn zein proteins, bovine serum albumin, egg albumin, proteins from wheat, barley, rye or oats, vegetable proteins, microbial proteins, legume proteins, proteins from tree nuts, and proteins from ground nuts.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the polysaccharide is selected from the group consisting of pectin, alginic acid and salts thereof, xanthan gum, chitosan, dextran, pullulan, chondroitin sulfate, gum arabic, gum karaya, gum tragacanth, and carrageenan.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the starch is hydrophobically modified.

### Claim 10 (depends on 1)

The composition of claim 1, wherein the polymeric matrix further comprises a polymer selected from the group consisting of ethyl cellulose and HPMC.

### Claim 11 (depends on 1)

The composition of claim 1, further comprising an antioxidant selected from the group consisting of phospholipids, alpha-lipoic acid, citric acid, Vitamin C and esters thereof, green tea polyphenols, green tea extracts, grape seed extracts, resveratrol, quercetin, cinamic acid and salts thereof, ferulic acid and salts thereof, rosemarinic acid and salts thereof, carotenoids, curcuminoids, superoxide dismutase, glutathione peroxidase, tocoferoles, tocotrienols, polyphenols, Coenzyme Q10, cysteine, methionine, and a combination thereof.

### Claim 12 (depends on 1)

The composition of claim 1, wherein the hydrophobic droplets further comprise an edible oil selected from the group consisting of vegetable oils, animal oils, marine oils, and microalgae oils.

### Claim 13 (depends on 12)

The composition of claim 12, wherein the vegetable oil is selected from the group consisting of rice bran oil, flaxseed oil, and oil comprising an omega-3 fatty acid or a conjugated linoleic acid.

### Claim 14 (depends on 12)

The composition of claim 12, wherein the animal oil is selected from the group consisting of marine oil, fish oil, and egg oil.

### Claim 15 (depends on 12)

The composition of claim 12, wherein the microalgae oil comprises an omega-3 fatty acid, an omega-6 fatty acid, or a conjugated linoleic acid.

### Claim 16 (depends on 1)

The composition of claim 1, wherein the composition is prepared according to a method comprising
(a) reducing the pH of a suspension comprising hydrophobic droplets and a first protein to below the isoelectric point (pKa) of the protein, wherein the hydrophobic droplets comprise a hydrophobic compound;
(b) irreversibly denaturing the first protein in the suspension of step (a), whereby the hydrophobic droplets are coated by a shell comprising the irreversibly denatured first protein;
(c) mixing the coated hydrophobic droplets of step (b) with a second protein, a starch, and a polysaccharide to form a mixture; and
(d) drying the mixture of step (c), whereby the composition is prepared.

### Claim 17 (depends on 1)

A consumable product comprising the composition of claim 1, wherein the consumable product has a therapeutic, nutritional, or disease-preventive effect.

### Claim 18 (depends on 17)

The product of claim 17, wherein the product is selected from the group consisting of food products, nutritional products, ready-to-drink mixes, supplements in the form of powder, tablet or capsule, vitamin premixes, pelleted animal feed, supplements or premixes, nutraceutical products, pharmaceutical products, and drugs.