[go: up one dir, main page]

WO2025030248A1 - Émulsion de cannabinoïdes - Google Patents

Émulsion de cannabinoïdes Download PDF

Info

Publication number
WO2025030248A1
WO2025030248A1 PCT/CA2024/051049 CA2024051049W WO2025030248A1 WO 2025030248 A1 WO2025030248 A1 WO 2025030248A1 CA 2024051049 W CA2024051049 W CA 2024051049W WO 2025030248 A1 WO2025030248 A1 WO 2025030248A1
Authority
WO
WIPO (PCT)
Prior art keywords
emulsion
acid
oil
composition
cannabinoid compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/CA2024/051049
Other languages
English (en)
Inventor
Andrew Hyman
Barbara Lynn ALLEN
Maxwell BEZAIRE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Black & Blue Foods Inc
Original Assignee
Black & Blue Foods Inc
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 Black & Blue Foods Inc filed Critical Black & Blue Foods Inc
Publication of WO2025030248A1 publication Critical patent/WO2025030248A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/10—Foods or foodstuffs containing additives; Preparation or treatment thereof containing emulsifiers
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • 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
    • A23L33/16—Inorganic salts, minerals or trace elements
    • 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
    • A61K31/658—Medicinal preparations containing organic active ingredients o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12—Carboxylic acids; Salts or anhydrides thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/42—Proteins; Polypeptides; Degradation products thereof; Derivatives thereof, e.g. albumin, gelatin or zein
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
    • 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
    • A61K9/0087—Galenical forms not covered by A61K9/02 - A61K9/7023
    • A61K9/0095—Drinks; Beverages; Syrups; Compositions for reconstitution thereof, e.g. powders or tablets to be dispersed in a glass of water; Veterinary drenches
    • 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
    • A61K9/10—Dispersions; Emulsions
    • A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
    • A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect

Definitions

  • the present application relates to emulsions comprising cannabinoid or cannabis derived compounds and optionally terpenes, and methods of preparation thereof. Further, the present application relates to compositions comprising the emulsion, and uses thereof.
  • Cannabinoids are a class of diverse chemical compounds that act on cannabinoid receptors in cells that alter neurotransmitter release in the brain. So far, over a hundred cannabinoids have been identified from cannabis, for example tetrahydrocannabinol (THC), cannabidiol (CBD). Cannabinoids have been shown to possess anxiolytic, antipsychotic, antiemetic and anti-inflammatory properties, and it is thus important to develop suitable optimized delivery systems in which cannabinoids will achieve a therapeutically effective dose.
  • THC tetrahydrocannabinol
  • CBD cannabidiol
  • Cannabinoids have been shown to possess anxiolytic, antipsychotic, antiemetic and anti-inflammatory properties, and it is thus important to develop suitable optimized delivery systems in which cannabinoids will achieve a therapeutically effective dose.
  • cannabinoids are hydrophobic compounds and are insoluble in water, which presents challenges in making products for oral consumption with effective bioavailability of cannabinoids at defined finished product concentrations.
  • Emulsions carry lipophilic compounds into suspended small oil droplets which makes them dispersible in aqueous phases. Nevertheless, the limited stability of emulsions remains a practical application issue, which means that with time they will undergo coalescence, creaming, sedimentation, Ostwald ripening and finally separation into their two original liquid phases due to free energy. This represents a big challenge for making products for oral consumption. Thus, careful consideration of components and methods of emulsification is needed to provide a stable emulsion. In addition, healthy components of the emulsion appropriate for oral administration are highly desirable.
  • US 10,143,212 patent discloses an emulsion, in which the lipid is encapsulated by a complex of casein and whey protein. However, this patent does not disclose an emulsion with cannabinoids, cannabis-derived compounds, terpenes or combinations thereof.
  • consumer products such as cannabis edibles, food supplements and natural health products (NHP)
  • NHS natural health products
  • aqueous-based products such as beverages.
  • the present application discloses an emulsion comprising cannabinoid compounds, optionally terpenes and casein and whey proteins.
  • the emulsion is stable at room temperature and at high temperature processing and provides a healthy and high concentration formulation of cannabinoid compounds that may be used to prepare, for example, liquid or powder compositions.
  • the liquid compositions may be used to prepare, for example, beverages.
  • the compositions of the application can be used, for example, in supplements and natural health products that improve the overall health of a subject which reduces the incidence and/or severity of diseases, disorders or conditions, for example by supporting the subject’s body’s own ability to reduce pain and/or inflammation.
  • present application includes an emulsion comprising: a) one or more cannabinoid compounds; b) a complex of whey protein and casein protein; c) water; and d) an oil.
  • the one or more cannabinoid compounds are selected from cannabigerolic acid (CBGA), cannabigerolic acid monomethylether (CBGAM), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerovarinic acid (CBGVA), cannabigerovarin (CBGV), cannabichromenic Acid (CBCA), cannabichromene (CBC), cannabichromevarinic acid (CBCVA), cannabichromevarin (CBCV), cannabidiolic acid (CBDA), cannabidiol (CBD), A6 cannabidiol (A6-CBD), cannabidiol monomethylether (CBDM), cannnabigerolic acid (CBGA), cann
  • the emulsion further comprises one or more terpenes and/or one or more terpenoids.
  • the oil is omega-3 oil.
  • the omega-3 oil is selected from oils obtained from fish such as salmon, tuna, herring, mackerel, anchovies, sardines, pollock, cod, catfish, flounder, grouper, halibut, mahi mahi, orange roughy, red snapper, shark, swordfish, tilefish, plankton, algae, krill and/or green-lipped mussel, and/or plant oils such as canola oil, borage oil, evening primrose oil, safflower oil, sunflower oil, flaxseed oil, wheat germ oil, algal oil, or and grapeseed oil, and oils obtained from chia seeds, kiwifruit seeds, perilla seeds, lingonberry seeds, camelina seeds, purslane seeds, black raspberry seeds, hemp seeds, butternut, walnuts,
  • the present application includes a powder formulation which comprises the emulsion of the present application.
  • the present application includes a use of the emulsion of the present application in compositions selected from beverages, gels, gelatins and concentrates and a use as a beverage enhancer.
  • the present application includes a composition selected from a beverage, gel, gelatin, concentrate and beverage enhancer, wherein the composition comprises the emulsion of the present application.
  • the present application includes a method of reducing the incidence and/or severity of a disease, disorder or condition, the method comprising administering a composition of the present application to a subject in need thereof.
  • the present application also includes a method of improving resistance to a disease, disorder or condition and/or improving immune response, the method comprising administering a composition of the present application to a subject in need thereof.
  • the disease, disorder or condition is joint pain, inflammatory pain and/or osteoarthritic pain.
  • Th present application also includes a method of preparing the emulsion, the dry formulation and the liquid composition of the present application.
  • Figure 1 shows the change of particle size (nm) over time (days) of initial batch Lot LC-NPMC-2022-04-18-1-B&B, an exemplary composition of the application.
  • the lines as seen at the y-axis at time 0 are as follows: 3000 psi, 1st pass; 6000 psi, 1 st pass; 10000 psi, 2nd pass; and 3000 psi, 2nd pass.
  • Figure 2 shows the change in particle size (nm) over time (days) of the experimental batch Lot LC-NPMC-2022-04-29-1-B&B, exemplary compositions of the application.
  • the lines as seen at the y-axis at time 0 are as follows: 5000 psi, 3rd pass; 5000 psi, 2nd pass; 5000 psi, 5th pass; 3000 psi, 5th pass; and 3000 psi, 3rd pass.
  • Figure 3 shows the parameter effect chart for particle size for exemplary compositions of the application.
  • Figure 4 shows the parameter effect chart for zeta potential for exemplary compositions of the application.
  • Figure 5 shows the parameter effect chart for change in particle size for exemplary compositions of the application.
  • Figure 6 shows the parameter effect chart for change in zeta potential for exemplary compositions of the application.
  • Figure 7 shows the parameter effect chart for change in pH for exemplary compositions of the application.
  • Figure 8 shows the high-performance liquid chromatography (HPLC) chromatogram of negative control sample.
  • Figure 9 shows particle size of exemplary emulsions stored for four weeks at 25 °C and 4 °C (top line refers to 25 °C showing a particle size of 978.7 after 4 weeks of storage and bottom line refers to 4 °C showing a particle size of 878.8 after 4 weeks of storage).
  • Figure 10 shows zeta potential of exemplary emulsions stored for four weeks at 25 °C and 4 °C (after one week of storage, top line refers to 4 °C showing a zeta potential of 33.4 and bottom line refers to 25 °C showing a zeta potential of 32.3).
  • the second compound as used herein is different from the other compounds or first compound.
  • a “third” compound is different from the other, first, and second compounds, and further enumerated or “additional” compounds are similarly different.
  • the term “and/or” as used herein means that the listed items are present, or used, individually or in combination. In effect, this term means that “at least one of” or “one or more” of the listed items is used or present.
  • the term “and/or” with respect to enantiomers, prodrugs, salts and/or solvates thereof means that the compounds of the application exist as individual enantiomers, prodrugs, salts and hydrates, as well as a combination of, for example, a salt of a solvate of a compound of the application.
  • cannabinoid refers to a class of chemical compounds that act on cannabinoid receptors in cells that alter neurotransmitter release in the brain and other organs and tissues of the endocannabinoid and immune systems.
  • Cannabinoids also include synthetic (made in a laboratory setting) and semisynthetic cannabinoids (derived or obtained from a natural source, e.g. plant, and is subsequently modified or derivatized in one or more different ways in a laboratory setting).
  • distillate refers to a purified cannabinoid obtained by a distillation of cannabis plant material, such as cannabis oil or cannabis extract.
  • cannabis plant material such as cannabis oil or cannabis extract.
  • the cannabis plant material is distilled to remove noncannabinoid components such as lipids, waxes, carbohydrates, and others and the distillation can be performed by any method known in the art.
  • isolated refers to a product of a purification of cannabis plant material, such as cannabis oil and cannabis extract or cannabinoid distillate, to obtain purified cannabinoid.
  • the purification in which non-cannabinoid components such as lipids, waxes, carbohydrates, and others are removed, can be performed by any purification method known in the art.
  • annabis oil refers to an oil extracted from a plant of the Cannabis genus and contains one or more cannabinoids.
  • annabis extract refers to material extracted from a plant of the Cannabis genus and contains one or more cannabinoids.
  • CBG cannabinoid found in the Cannabis genus of plants or synthetic or semi-synthetic analogue thereof.
  • CBG has the following chemical structure:
  • CBD cannabinoid found in the Cannabis genus of plants or synthetic or semi-synthetic analogue thereof.
  • CBD has the following chemical structure:
  • THC tetrahydrocannabinol
  • cannabinoid ((-)-trans-A9-tetrahydrocannabinol) found in the Cannabis genus of plants or synthetic or semi-synthetic analogue thereof.
  • THC has the following chemical structure:
  • terpene and “terpenoids” as used herein refers to cannabis derived terpenes/terpenoids and non-cannabis derived terpenes. Terpenes are hydrocarbons, whereas terpenoids contain additional functional groups.
  • flavonoids refers to any compound of a class of plant pigments having a structure based on or similar to that of flavone. Chemically, flavonoids have the general structure of a 15-carbon skeleton, which consists of two phenyl rings and a heterocyclic ring.
  • aqueous solution refers to a water-based solution.
  • nutraceutical or “nutraceutical” as used herein is a combination of the terms “nutritional” and “pharmaceutical”. It refers to a composition, which is known or suspected in the art to positively affect human nutrition and/or health. Nutraceuticals include nutritional supplements and natural health products (NHP), which may or may not have regulatory approval.
  • emulsion refers to a colloidal dispersion of two immiscible liquids, for example, an oil and water, one of which is part of a continuous phase and the other of which is part of a dispersed phase.
  • omega-3 fatty acid as used herein means a polyunsaturated fatty acid whose first double bond occurs at the third carbon-carbon bond from the end opposite the acid group.
  • omega-3 oil as used herein means oil that contains at least one (e.g., one, two, or three) fatty acid(s) containing a carbon-carbon double bond in the n-3 position (i.e. , the third bond from the methyl end of the fatty acid).
  • particle size refers to oil in water droplet average diameter in an emulsion.
  • stable refers the ability of the compound, composition or emulsion of the application to resist change in its chemical properties over time.
  • subject includes all members of the animal kingdom including mammals, and suitably refers to humans.
  • treating means an approach for obtaining beneficial or desired results, including clinical results.
  • beneficial or desired results include, but are not limited to alleviation or amelioration of one or more symptoms or conditions, diminishment of extent of one or more symptoms or conditions, stabilized (i.e. not worsening) state of one or more symptoms or conditions, preventing spread of one or more symptoms or conditions, diminishment of the reoccurrence of one or more symptoms or conditions (whether partial or total), whether detectable or undetectable.
  • Treating and “treatment” as used herein also include prophylactic treatment. Treatment methods comprise administering to a subject an effective amount of one or more of the emulsions or compositions of the present application and optionally consist of a single administration, or alternatively comprise a series of administrations.
  • the term “effective amount” or “therapeutically effective amount” means an amount of an emulsion or a composition of the application that is effective, at dosages and for periods of time necessary to achieve the desired result.
  • administered means administration of a therapeutically effective amount of an emulsion of the application or a composition of the application to a subject.
  • emulsion of the application refers to the emulsion as described herein.
  • composition of the application refers to the compositions comprising the emulsion of the application.
  • powder formulation refers to a powder obtained by drying the emulsion of the application.
  • wt% refers to wt/wt%.
  • the present application includes an emulsion comprising: a) one or more cannabinoid compounds; b) a complex of whey protein and casein protein; c) water; and d) an oil.
  • the one or more cannabinoid compounds are selected from cannabigerolic acid (CBGA), cannabigerolic acid monomethylether (CBGAM), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerovarinic acid (CBGVA), cannabigerovarin (CBGV), cannabichromenic Acid (CBCA), cannabichromene (CBC), cannabichromevarinic acid (CBCVA), cannabichromevarin (CBCV), cannabidiolic acid (CBDA), cannabidiol (CBD), A6 cannabidiol (A6-CBD), cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD C4), cannabidivarinic acid (CBDVA), cannabidivarin (CBDV), cannabidiorcol (CBD C1), tetrahydrocanna
  • the one or more cannabinoid compounds are a salt, isomer, enantiomer, or optically active derivative thereof.
  • the one or more cannabinoid compounds are derived from a natural source.
  • the one or more cannabinoid compounds are derived from a plant of the Cannabis genus, e.g., Cannabis sativa, Cannabis indica, Cannabis hybrid, or other genera.
  • the one or more cannabinoid compounds are synthetic or semi-synthetic cannabinoids.
  • the one or more cannabinoid compounds are comprised in a distillate, an isolate, cannabis oil, cannabis extract or a combination thereof. In some embodiments, the one or more cannabinoid compounds are comprised in a distillate. In some embodiments, the one or more cannabinoid compounds are comprised in an isolate. In some embodiments, the one or more cannabinoid compounds are comprised in a cannabis oil. In some embodiments, the one or more cannabinoid compounds are comprised in a cannabis extract.
  • the distillate is obtained from cannabis extract or cannabis oil.
  • the cannabis extract or cannabis oil are distilled to obtain the distillate.
  • the distillate comprises from about 70 wt% to about 95 wt %, from about 75 wt% to about 90 wt%, from about 80 wt% to about 95 wt %, from about 85 wt% to about 95 wt % of one or more cannabinoid compounds.
  • the distillate comprises about 85, 86, 87, 88, 89, 90, 91 , 92 or 93 wt% of one or more cannabinoid compounds, and values therebetween.
  • the isolate comprises from about 95 wt% to about 100 wt%, about 97 wt% to about 100 wt%, or about 98 wt% to about 100 wt % of one or more cannabinoid compounds, and values therebetween.
  • the cannabis oil containing one or more cannabinoid compounds is extracted from a plant of the Cannabis genus, e.g., Cannabis sativa, Cannabis indica, Cannabis hybrid, or other genera, using various techniques known in the art, such as solvent-based extraction.
  • the cannabis extract containing one or more cannabinoid compounds is extracted from a plant of the Cannabis genus, e.g., Cannabis sativa, Cannabis indica, Cannabis hybrid, or other genera, using any suitable technique for separating cannabinoids from the plant.
  • the extract can be obtained using solvent-based extraction.
  • the one or more cannabinoid compounds is or comprises CBG, or a salt, isomer, enantiomer, or optically active derivative thereof. In some embodiments, the one or more cannabinoid compounds is or is comprised in a CBG distillate. In some embodiments, the one or more cannabinoid compounds is or is comprised in a CBG isolate.
  • the one or more cannabinoid compounds is or comprises CBD, or a salt, isomer, enantiomer, or optically active derivative thereof. In some embodiments, the one or more cannabinoid compounds is or is comprised in a CBD distillate. In some embodiments, the one or more cannabinoid compounds is or is comprised in a CBD isolate.
  • the one or more cannabinoid compounds is or comprises THC, or a salt, isomer, enantiomer, or optically active derivative thereof. In some embodiments, the one or more cannabinoid compounds is or is comprised in a THC distillate. In some embodiments, the one or more cannabinoid compounds is or is comprised in a THC isolate.
  • the emulsion of the application comprises one cannabinoid (single cannabinoid). In some embodiments, the emulsion of the application comprises two or more cannabinoid compounds. In some embodiments, the emulsion of the application comprises two, three, four or more cannabinoid compounds. In some embodiments, the emulsion of the application comprises two cannabinoid compounds. In some embodiments, the emulsion of the application comprises two or more cannabinoid compounds comprised in a distillate, an isolate, cannabis oil, cannabis extract or a combination thereof.
  • the one or more cannabinoid compounds are present in the emulsion in an amount of about 0.25 wt% to about 13 wt% of the emulsion. In some embodiments, the one or more cannabinoid compounds are present in the emulsion in an amount of about 0.25 wt%, about 0.5 wt%, about 1 wt%, about 1 .5 wt%, about 2 wt%, about 4 wt%, about 5 wt%, about 7 wt%, about 8.5 wt% or about 10 wt% and values therebetween.
  • the one or more cannabinoid compounds are present in the emulsion in an amount of about 0.5 wt%. In some embodiments, the one or more cannabinoid compounds are present in the emulsion in an amount of about 1.2 wt%. In some embodiments, the one or more cannabinoid compounds are present in the emulsion at in an amount of about 2.4 wt%. In some embodiments, the one or more cannabinoid compounds are present in the emulsion in an amount of about 5.1 wt%. In some embodiments, the one or more cannabinoid compounds are present in the emulsion in an amount of about 10.2 wt%.
  • the emulsion further comprises one or more terpenes, one or more terpenoids, one or more flavonoids, and any combinations thereof. In some embodiments, the emulsion further comprises one or more terpenes and/or one or more terpenoids.
  • the one or more terpenes and/or one or more terpenoids are selected from abietane, alpha-bisabolol, alphaphellandrene, alpha-pinene, beta-caryophyllene, beta-myrcene, beta-pinene, borneol, cadinene, camphene, camphor, carvacrol, caryophyllene acetate, caryophyllene oxide, cedrane, cembrene, citral, citronellol, copaene, dextro carvone, dextro fenchone, eucalyptol, eugenol, farnesene, gama-3-carene, gamma-terpinene, geraniol, geranyl acetate, guaiazulene, guaiene, humulene, isopulegol, labdane, limonene, linaloo
  • the one or more terpenes and/or one or more terpenoids comprise hemiterpenes, monoterpenols, terpene esters, diterpenes, monoterpenes, polyterpenes, tetraterpenes, terpenoid oxides, sesterterpenes, sesquiterpenes, norisoprenoids, or their derivatives, as well as isomeric, enantiomeric, or optically active derivatives thereof.
  • the derivatives of the one or more terpenes and/or one or more terpenoids comprise terpenoids, hemiterpenoids, monoterpenoids, sesquiterpenoids, sesterterpenoid, sesquarterpenoids, tetraterpenoids, triterpenoids, tetraterpenoids, polyterpenoids, isoprenoids, or steroids.
  • the one or more terpenes and/or one or more terpenoids comprise a-(alpha), p-(beta), y- (gamma), oxo-, isomers, or any combinations thereof.
  • the emulsion further comprises one or more flavonoids selected from bioflavonoids, isoflavonoids and neoflavonoids.
  • the one or more flavonoids are present in the emulsion in an amount of from about 0.00001 wt% to about 0.01 wt%.
  • the one or more terpenes and/or one or more terpenoids are present in the emulsion in an amount of about 0 wt% to about 13 wt% of the emulsion. In some embodiments, the one or more terpenes and/or one or more terpenoids are present in the emulsion in an amount of about 0 to about 0.1 wt%, about 0 to about 0.5 wt%, about 0.5 to about 1 wt%, about 0 to about 1 wt%, about 0 to about 5 wt%, about 0 to about 12 wt%, about 1 to about 2 wt%, about 2 to about 3 wt%, about 3 to about 4 wt%, about 4 to about 5 wt%, about 5 to about 7.5 wt%, about 5 to about 10 wt% or about 10 to about 12.5 wt%, and values therebetween.
  • the whey protein used in the emulsion of the application is any milk serum protein or protein composition known in the art, including, but not limited to, protein isolate, whey protein concentrate, a-lactalbumin and/or p- lacoglobulin.
  • the whey protein is selected from whey protein isolate, whey protein concentrate, a-lactalbumin and p-lacoglobulin.
  • the whey protein is whey protein isolate.
  • the casein protein used in the emulsion of the application is any casein protein known in the art.
  • the casein protein is selected from a-casein, K-casein, p-casein, b-casein, and their salts, such as sodium, potassium, calcium and ammonium, or mixtures thereof. In some embodiments, the casein protein is sodium caseinate.
  • the whey protein is present in the emulsion in an amount of about 0.25 wt% to about 5 wt% of the emulsion. In some embodiments, the whey protein is present in the emulsion in an amount of about 0.5 wt%, about 1 wt%, about 1 .25 wt%, about 1 .5 wt%, about 1 .8 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, about 4.5 wt% or about 5 wt% and values therebetween.
  • the whey protein is present in the emulsion in an amount of about 0.5 wt%. In some embodiments, the whey protein is present in the emulsion in an amount of about 1 .3 wt%. In some embodiments, the casein protein is present in the emulsion in an amount of about 3 wt%.
  • the casein protein is present in the emulsion in an amount of about 0.25 wt% to about 5 wt% of the emulsion. In some embodiments, the casein protein is present in the emulsion in an amount of about 0.5 wt%, about 1 wt%, about 1.25 wt%, about 1.5 wt%, about 1.8 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, about 4.5 wt% or about 5 wt% and values therebetween. In some embodiments, the casein protein is present in the emulsion in an amount of about 0.5 wt%. In some embodiments, the casein protein is present in the emulsion in an amount of about 1 .3 wt%. In some embodiments, the casein protein is present in the emulsion in an amount of about 3 wt%.
  • the weight ratio of casein protein to whey protein is about 10:1 to about 1 :10. In some embodiments, the weight ratio of casein protein to whey protein is about 6:1 to about 1 :6, about 3:1 to about 1 :3, about 2:1 to about 1 :2 or about 1 :1. In some embodiments, the weight ratio of casein protein to whey protein is about 6:1 to about 1 :6. In some embodiments, the weight ratio of casein protein to whey protein is 1 :1 .
  • the whey protein is present in the emulsion in an amount of about 1.3 wt% and the casein protein is present in the emulsion in an amount of about 1 .3 wt%.
  • the complex comprises whey protein and casein protein which are cross-linked or covalently bonded.
  • the one or more cannabinoid compounds are encapsulated in the complex of whey protein and casein protein.
  • the water is present in the emulsion of the application in an amount of about 65 wt% to about 80 wt% of the emulsion. In some embodiments, the water is present in the emulsion of the application in an amount of about 68 wt%, about 70 wt%, about 73 wt%, about 75 wt%, or about 78 wt% and values therebetween.
  • the whey protein and casein protein are dissolved in the water to form an aqueous solution and the emulsion is formed between the aqueous solution comprising the complex and the oil, and the one or more cannabinoid compounds are encapsulated by the complex of whey protein and casein protein.
  • the oil which is used in the emulsion of the application includes any oil used in food, pharmaceutical or cosmetic industries.
  • the oil is an edible oil.
  • the oil is extracted from any appropriate source such as a marine animal, plant, phytoplankton or algae including microalgae, or is produced synthetically.
  • the oil can be used in non-purified, purified or highly purified form, concentrated or non-concentrated. The oil aids in the dissolution of the cannabinoid or cannabis derived compound and allows for emulsification of the cannabinoid and cannabis-derived compounds.
  • the oil is an omega-3 oil.
  • the oil contains omega-3 fatty acids or omega-3 fatty acid precursors such as a- linolenic acid.
  • the fatty acids that are present in the omega-3 oil are selected from one or more of all-cis-7,10,13-hexadecatrienoic acid; a-linolenic acid (ALA) (all-cis-9,12,15-octadecatrienoic acid); stearidonic acid (SDA) (all-cis- 6,9,12,15-octadecatetraenoic acid); eicosatrienoic acid (ETE) (all-cis- 11 ,14,17- eicosatrienoic acid); eicosatetraenoic acid (ETA) (all-cis-8,11 ,14,17-eicosatetraenoic acid); eicosapentaenoic acid (EPA) (all-
  • the omega-3 is selected from oils obtained from fish such as salmon, tuna, herring, mackerel, anchovies, sardines, pollock, cod, catfish, flounder, grouper, halibut, mahi mahi, orange roughy, red snapper, shark, swordfish, tilefish, plankton, algae, krill and/or green-lipped mussel, and/or plant oils such as canola oil, borage oil, evening primrose oil, safflower oil, sunflower oil, flaxseed oil, wheat germ oil, algal oil, and/or grapeseed oil, and/or oils obtained from chia seeds, kiwifruit seeds, peri Ila seeds, lingonberry seeds, camelina seeds, purslane seeds, black raspberry seeds, hemp seeds, butternut, walnuts, pecan nuts, and/or hazel nuts.
  • the oil is sunflower oil.
  • the oil is algal oil.
  • the oil is present in the emulsion of the application in an amount of about 8 wt% to about 30 wt% of the emulsion. In some embodiments, the oil is present in the emulsion of the application in an amount of about 8 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt% or about 30 wt% and values therebetween. In some embodiments, the oil is present in the emulsion of the application in an amount of about 20 wt%.
  • the weight ratio of oil to one or more cannabinoid compounds is about 100:1 to about 1 :1. In some embodiments, the weight ratio of oil to at least one cannabinoid or cannabis derived compound is about 80:1 , about 20:1 , about 7:1 , about 2:1 , or about 1 :1.
  • the emulsion further comprises one or more pH adjusting agents selected from sodium acetate, phosphoric acid, acetic acid, lactic acid, fumaric acid, adipic acid, malic acid, tartaric acid, citric acid, hydrochloric acid, sulfuric acid, potassium hydroxide, salts thereof, and combinations thereof.
  • the one or more pH adjusting agents comprise citric acid and potassium hydroxide.
  • the citric acid is anhydrous citric acid.
  • the one or more pH adjusting agents are present in the emulsion of the application in an amount of about 0.1 wt% to about 5 wt% of the emulsion. In some embodiments, the one or more pH adjusting agents are present in the emulsion of the application in an amount of about 0.5 wt%, about 1 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, or about 4.5 wt% and values therebetween. In some embodiments, the one or more pH adjusting agents are present in the emulsion of the application in an amount of about 0.9 wt%.
  • the pH of the final emulsion is below about 4. In some embodiments, the pH of the final emulsion is from about 2 to about 3.2.
  • the emulsion further comprises one or more antifoaming agents.
  • the anti-foaming agents which can be used in the emulsion of the application are any anti-foaming agents known in the art. Examples include, but are not limited to polydimethylsiloxane, fatty acid ester, silicon dioxide, vegetable oil based anti-foaming agents and the like.
  • the one or more anti-foaming agents are present in the emulsion of the application in an amount of about 0.005 wt% to about 0.1 wt % of the emulsion. In some embodiments, the one or more anti-foaming agents are present in the emulsion of the application in an amount of about 0.01 wt%, about 0.05 wt%, or about 0.08 wt% and values therebetween. In some embodiments, the one or more anti-foaming agents are present in the emulsion in an amount of about 0.01 wt%.
  • the encapsulation of the one or more cannabinoid compounds by the complex is achieved by homogenization of the mixture of the protein complex and the one or more cannabinoid compounds. This results in the formation of microparticles of the one or more cannabinoid compounds, which are encapsulated in the protein complex.
  • the emulsion of the application has an average particle size of below about 1000 nm. In some embodiments, the emulsion of the application has an average particle size of about 50 nm to about 900 nm, about 50 nm to about 800 nm, about 50 nm to about 700 nm, about 50 nm to about 600 nm, about 50 nm to about 500 nm, about 50 to about 400 nm, about 50 nm to about 300 nm, or about 900 nm, about 800 nm, about 700 nm, about 600 nm, about 500 nm, or about 400 nm and values therebetween. In some embodiments, the particle size is determined using dynamic light scattering method.
  • the protein complex which is adsorbed at the oil-water interface, greatly improves the stability of the emulsion of the application and protects the one or more cannabinoid compounds of the application from exposure to oxidants and pro-oxidants.
  • Pro-oxidants such as metal ions, are able to lower the activation energy for the initiation of oxidation.
  • Some of these metal ions are bound by the protein complexes, which reduces their negative impact on the oxidation of the one or more cannabinoid compounds.
  • the emulsion of the application is a stable oil-in- water emulsion. In some embodiments, the emulsion of the application is stable at room temperature for at least two weeks orfor at least three weeks. Thus, the emulsion of the applications remains free from degradation of the one or more cannabinoid compounds of the application and maintains homogeneous content and appearance. Determination whether an emulsion has lost its stability may be carried out by any of the following techniques: measurement of particle size, zeta potential, light scattering, focused beam reflectance measurement, centrifugation, rheology, potency analysis of the cannabinoids and other active ingredients, assessment of visual appearance or a combination thereof.
  • the emulsion of the application has zeta potential of above about 30 mV. In some embodiments the emulsion of the application has zeta potential of above about 33 mV, above about 35 mV, above about 40, or above about 45 mV. In some embodiments, the emulsion of the application has zeta potential of between about 40 mV to about 50 mV.
  • the present application includes an emulsion comprising: a) about 0.25 wt% to about 13 wt% of one or more cannabinoid compounds; b) about 0.25 wt% to about 5 wt% of casein protein; c) about 0.25 wt% to about 5 wt% of whey protein; d) about 8 wt% to about 30 wt% oil; e) optionally about 0.1 wt% to about 5 wt% of one or more pH adjusting agents; f) optionally about 0.005 wt% to about 0.1 wt % of one or more anti-foaming agents; and g) water to make 100%.
  • the present application includes an emulsion comprising: a) about 1 wt% to about 12 wt% of one or more cannabinoid compounds; b) about 0.8 wt% to about 2 wt% of casein protein; c) about 0.8 wt% to about 2 wt% of whey protein; d) about 8 wt% to about 22 wt% oil; e) optionally about 2 wt% to about 5 wt% of one or more pH adjusting agents; f) optionally about 0.005 wt% to about 0.1 wt % of one or more anti-foaming agents; and g) water to make 100%.
  • the present application includes an emulsion comprising: a) about 1 wt% to about 12 wt% of one or more cannabinoid compounds; b) about 1 .3 wt% of casein protein; c) about 1 .3 wt% of whey protein; d) about 8 wt% to about 22 wt% oil; e) optionally about 2 wt% to about 5 wt% of one or more pH adjusting agents; f) optionally about 0.005 wt% to about 0.1 wt % of one or more anti-foaming agents; and g) water to make 100%.
  • the emulsion of the application has the advantage that it is resistant to oxidation, has a long shelf-life and/or is stable at high temperature processing, thus allowing it to be heat-treated or sterilized. This is of great benefit as it allows one or more encapsulated cannabinoid compounds of the application to be added to products that must be sterilized before consumption.
  • the application provides convenient formulations of cannabinoid compounds useful for enhancing or creating aqueous soluble cannabinoid compositions.
  • the emulsion of the application may be useful, for example, to prepare compositions selected from a beverage, gel, gelatin and concentrate and as a beverage enhancer. As such, the emulsion of the application is for use in compositions selected from beverages, gels, gelatins and concentrates and as a beverage enhancer.
  • the present application also includes a composition selected from a beverage, gel, gelatin, concentrate and beverage enhancer, wherein the composition comprises the emulsion of the present application.
  • the composition is a beverage.
  • the beverage is selected from water, milk, tea, coffee, fruit juice (e.g., orange, apple, cranberry, pear, currant, etc.), vegetable juice (e.g., carrot, tomato, etc.), nutritional supplement, natural health product, punch and carbonated drink (e.g. sparkling water, soda water, sports drink, and soft drink, such as a cola).
  • the beverage is the nutritional supplement or the natural health product.
  • the one or more cannabinoids are present in the composition of the application at a concentration of about 0.001 mg/ml to about 5 mg/mL, about 0.01 mg/mL to about 4 mg/mL, about 0.1 mg/mL to about 3 mg/mL, about 0.5 mg/mL to about 2 mg/mL, about 1 mg/mL to about 1 .5 mg/mL, and values therebetween. In some embodiments, the one or more cannabinoids are present in the composition of the application at a concentration of about 0.2 mg/mL, about 0.4 mg/mL, about 0.85 mg/mL, or about 1.7 mg/mL.
  • the one or more cannabinoids are present in the composition of the application in an amount of about 10 mg to about 500 mg, about 15 mg to about 450 mg, about 20 mg to about 400 mg, about 50 mg to about 300 mg, about 100 mg to about 200 mg, and values therebetween. In some embodiments, the one or more cannabinoids are present in a composition of the application in an amount of about 20 mg, about 50 mg, about 100 mg, about 210 mg, or about 420 mg.
  • the composition of the application comprises a liquid selected from water, oil, and alcohol.
  • the liquid is selected from plain water, alcohol, non-alcoholic drink, soft drink, fruit juice, vegetable juice, tea, coffee, milk, punch or other hot, room temperature or cold liquids used in drinks.
  • the composition of the application can be caffeinated or non-caffeinated. Such compositions may be produced in ready to use form or be produced in a form suitable for preparation in final consumable form at or proximate to the time of ingestion.
  • the liquid is present in the composition of the application in an amount of between about 50% wt% to about 99.99% wt% of the composition of the application.
  • the liquid is present in the composition of the application in an amount of between about 80% wt% to about 99.99% wt%. In some embodiments, the liquid is present in the composition of the application in an amount of between about 80% wt% to about 99.9% wt%. In some embodiments, the liquid is present in the composition of the application in an amount of between about 95% wt% to about 99.9% wt%. In some embodiments, the liquid is water.
  • the composition of the application comprises between about 0.5% wt% to about 25% wt% of the emulsion of the application, between about 1 % wt% to about 10% wt% of the emulsion of the application, or between about 1 % wt% to about 5% wt% of the emulsion of the application, based on the total weight of the composition. In some embodiments, the composition of the application comprises between about 0.5% wt% to about 3% wt% of the emulsion of the application based on the total weight of the composition.
  • the emulsions and the compositions of the application include any number of other additives, including without limitation a solvent, a bulking agent, an antioxidant such as naturally derived antioxidant (e.g. polyphenols and anthrocyanidins), or a nutritional supplement.
  • additives may be used either alone or in combination to improve, for example, the chemical and/or physical properties, stability, nutritional profile, taste, colour and/or viscosity, of the emulsions and the compositions of the application.
  • the emulsions and the compositions of the application further include one or more suitable types of modifiers and additives, the one or more of additives are selected from anti-foaming agents, stabilizers, viscosity modifiers, emulsifiers, oils, thickening agents, minerals, acids, bases, vitamins, flavours, colourants, sweeteners (e.g. liquid sweeteners), and the like and combinations thereof, to provide improved solubility, stability, bioavailability, colour and taste.
  • the compositions of the application comprise a stabilizer to maintain stability and prevent degeneration.
  • stabilizers include but are not limited to acai gum (gum Arabic), agar-agar, ammonium alginate, calcium alginate, carob bean gum (locust bean gum), chondrus extract (carrageenan), ghatti gum, guar gum, pectin, potassium alginate, sodium alginate, sterculia gum (karaya gum), tragacanth, gelatin, lecithin, mono-glycerides, di-glycerides, maltodextrin, xanthan gum, proplylene glycol alginates (PGA), microcrystalline cellulose, sodium carboxymethyl cellulose, Purity Gum 2000 (modified starch), pectin, carrageenan, casein and inulin.
  • the stabilizer is pectin.
  • the pectin is present in the composition in an amount of between about 0.1 % wt% to about 5% wt% of the composition of the application.
  • the emulsions and the compositions of the application further comprise at least one nutritional supplement.
  • the nutritional supplements are selected from vitamin A, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B9, vitamin B12, vitamin C, vitamin D, vitamin E, vitamin K calcium, phosphorus, potassium, sulfur, sodium, chlorine, magnesium, iron, cobalt, copper, zinc, molybdenum, iodine, selenium, manganese, nickel, chromium, fluorine, boron, strontium histidine, isoleucine, leucine, lysine, methionine, cysteine, phenylalanine, tyrosine, threonine, tryptophan, valine, alpha-linoleic acid, linoleic acid, L-theanine, malic acid, curcumin, or a combination thereof.
  • compositions are packaged as individual packages, suitably single use packages, or as multiple packages.
  • the packaging is in air tight containers.
  • packaging is comprised of paper, plastic, metal, and/or glass.
  • compositions include bubble containing or producing liquids with dissolved gas or liquids capable of producing gas proximately in time of consumption.
  • compositions with dissolved gas are created by a method comprising addition of carbon dioxide, ozone, oxygen, or nitrogen.
  • dissolved gas is added to the composition by methods comprising application of pressure, or adding water with the dissolved gas. The dissolved gas is released from the composition when pressure is reduced as effervescence.
  • the emulsion of the application is further dried to form a powder formulation for use in the composition of the application.
  • the emulsion of the application is dried using any method known in the art to evaporate the water phase of the emulsion, and possibly none, some or essentially all of the oil.
  • the emulsion of the application is spray dried to form the powder formulation.
  • Alternative methods include, but are not limited to, pan coating, air-suspension coating, centrifugal extrusion, vibrational nozzle technique, freeze-drying or using a food dehydrator. As such, the emulsion of the application is for use in a powder formulation.
  • the present application also includes a powder formulation which comprises the emulsion of the present application.
  • the resulting powder formulation is diluted with a bulking agent or a mixture of bulking agents.
  • suitable bulking agents include, for example, gum arabic, waxy maize starch, dextrin, maltodextrin, polydextrose, inulin, fructooligosaccharide, sucrose, glucose, fructose, galactose, lactose, maltose, trehalose, cellobiose, lactulose, ribose, arabinose, xylose, lyxose, allose, altrose, mannose, gulose, talose, erythritol, threitol, arabitol, xylitol, mannitol, ribitol, galactitol, fucitol, inositol, maltitol, sorbitol, isomalt, lactitol, polyglycitol,
  • the bulking agent furthers comprises a sweetener, pH modifier, pH stabilizer, antimicrobial preservative, antioxidant, texture modifier, or colourant, or combinations thereof.
  • the powder formulation is mixed directly in a liquid composition of the application or is dissolved in a solution to then be added to the composition of the application.
  • the powder formulation is prepared and packaged using any packaging known in the art.
  • the powder formulation is packaged as a single serving or multiple servings in a metal, glass, and/or plastic container.
  • the powder formulation is packaged as a single serving stick pack or pouch.
  • the emulsions of the application enhance or maintain the stability of the one or more cannabinoids in the emulsion and in the composition produced therefrom.
  • the composition of the application is stable at room temperature for at least one week with ⁇ 30% decrease, ⁇ 20% decrease or less than 10% decrease in amount of the one or more cannabinoids.
  • the composition of the application is stable at room temperature for at least two weeks with ⁇ 40% decrease, ⁇ 30% decrease or less than 25% decrease in amount of the one or more cannabinoids.
  • the emulsion of the application remains free from degradation of one or more cannabinoids and maintains homogeneous appearance.
  • the present application includes a method of preparing an emulsion comprising one or more cannabinoid compounds, the method comprising: a) heating an aqueous solution of casein protein and whey protein to form an aqueous solution comprising a casein protein and whey protein complex; b) mixing the one or more cannabinoid compounds with an oil to form a first mixture; c) dispersing the mixture formed in b) in the aqueous solution of a) to form a second mixture; and d) homogenizing the second mixture formed in c) to form the emulsion.
  • the complex comprises whey protein and casein protein which are cross-linked or covalently bonded.
  • the pH of the aqueous solution of casein protein and whey protein complex is adjusted to about 6 to about 9, prior to the heating in a). In some embodiments, the pH of the aqueous solution of casein protein and whey protein is adjusted to about 6.5 to about 8, prior to the heating in a). In some embodiments, the pH of the aqueous solution of casein protein and whey protein is adjusted to about 7.5 to about 8, prior to the heating in a).
  • the pH of the aqueous solution is adjusted using any pH adjusting agent, such as potassium hydroxide, sodium hydroxide, disodium hydrogen phosphate, sodium bicarbonate, sodium phosphate tribasic, dipotassium hydrogen phosphate, and combinations thereof.
  • any pH adjusting agent such as potassium hydroxide, sodium hydroxide, disodium hydrogen phosphate, sodium bicarbonate, sodium phosphate tribasic, dipotassium hydrogen phosphate, and combinations thereof.
  • the casein protein and whey protein complex is formed by heating the aqueous solution of casein and whey protein at about 70° C to about 100° C. In some embodiments, the complex is formed by heating the aqueous solution of casein and whey protein at about 80° C to about 95° C, or at about 90° C. In some embodiments, the aqueous solution of casein and whey protein is heated for about 1 minute to about 30 minutes, from about 5 minutes to about 20 minutes, or for about 5 minutes. In some embodiments, after heating, the aqueous solution is cooled to below about 20° C, or to about 10° C.
  • the pH of the aqueous solution of casein protein and whey protein complex is adjusted to below about 4. In some embodiments, the pH of the aqueous solution of casein protein and whey protein complex is adjusted to about 2 to about 3.2 after the heating in a). In some embodiments, the pH of the aqueous solution of casein protein and whey protein complex is adjusted using any pH adjusting agent, such as sodium acetate, phosphoric acid, acetic acid, lactic acid, fumaric acid, adipic acid, malic acid, tartaric acid, citric acid, hydrochloric acid, sulfuric acid, salts thereof, and combinations thereof.
  • any pH adjusting agent such as sodium acetate, phosphoric acid, acetic acid, lactic acid, fumaric acid, adipic acid, malic acid, tartaric acid, citric acid, hydrochloric acid, sulfuric acid, salts thereof, and combinations thereof.
  • the mixing of the one or more cannabinoid compounds with an oil in b) further comprises sonication.
  • the sonication is performed in an ultrasonic bath at about 80 kHz at 100 % power for about 10 minutes. In some embodiments, the sonication is performed under conditions to render the mixture homogenous.
  • the mixing of the one or more cannabinoid compounds with an oil in c) further comprises heating.
  • the mixing in c) is performed at a temperature of about 40° C to about 50° C.
  • the homogenizing in d) is performed using any known method. Suitable methods include, for example, high-pressure homogenization (HPH), high-shear homogenization or microfluidization. In some embodiments, the homogenizing in d) is performed by a top homogenizer. In some embodiments, the homogenizing in d) comprises using a microfluidizer at about 2,500 psi and about 40,000 psi pressure. In some embodiments, the microfluidizer is set at about 10,000 psi and about 40,000 psi, or at about 20,000 psi and about 40,000 psi of pressure is applied to create an emulsion system with particles less than about 500 nm.
  • HPH high-pressure homogenization
  • microfluidization microfluidization
  • the homogenizing in d) comprises using a microfluidizer at about 2,500 psi and about 40,000 psi pressure.
  • the microfluidizer is set at about 10,000 ps
  • the complex comprises whey protein and casein protein which are cross-linked or covalently bonded.
  • the one or more cannabinoid compounds is encapsulated in the complex of whey protein and casein protein.
  • the one or more cannabinoid compounds are selected from cannabigerolic acid (CBGA), cannabigerolic acid monomethylether (CBGAM), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerovarinic acid (CBGVA), cannabigerovarin (CBGV), cannabichromenic Acid (CBCA), cannabichromene (CBC), cannabichromevarinic acid (CBCVA), cannabichromevarin (CBCV), cannabidiolic acid (CBDA), cannabidiol (CBD), A6 cannabidiol (A6-CBD), cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD C4), cannabidivarinic acid (CBDVA), cannabidivarin (CBDV), cannabidiorcol (CBD C1), tetrahydrocanna
  • the one or more cannabinoid compounds are a salt, isomer, enantiomer, or optically active derivative thereof.
  • the one or more cannabinoid compounds are derived from a natural source.
  • the one or more cannabinoid compounds are derived from a plant of the Cannabis genus, e.g., Cannabis sativa, Cannabis indica, Cannabis hybrid, or other genera.
  • the one or more cannabinoid compounds are synthetic or semi-synthetic cannabinoids.
  • the one or more cannabinoid compounds are comprised in a distillate, an isolate, cannabis oil, cannabis extract or a combination thereof. In some embodiments, the one or more cannabinoid compounds are comprised in a distillate. In some embodiments, the one or more cannabinoid compounds are comprised in an isolate. In some embodiments, the one or more cannabinoid compounds are comprised in a cannabis oil. In some embodiments, the one or more cannabinoid compounds are comprised in a cannabis extract.
  • the distillate is obtained from cannabis extract or cannabis oil.
  • the cannabis extract or cannabis oil are distilled to obtain the distillate.
  • the distillate comprises from about 70 wt% to about 95 wt %, from about 75 wt% to about 90 wt %, from about 80 wt% to about 95 wt %, from about 85 wt% to about 95 wt % of one or more cannabinoid compounds.
  • the distillate comprises about 85, 86, 87, 88, 89, 90, 91 , 92 or 93 wt % of one or more cannabinoid compounds, and values therebetween.
  • the isolate comprises from about 95 wt% to about 100 wt%, about 97 wt% to about 100 wt%, or about 98 wt% to about 100 wt % of one or more cannabinoid compounds, and values therebetween.
  • the cannabis oil containing one or more cannabinoid compounds is extracted from a plant of the Cannabis genus, e.g., Cannabis sativa, Cannabis indica, Cannabis hybrid, or other genera, using various techniques known in the art, such as solvent-based extraction.
  • the cannabis extract containing one or more cannabinoid compounds is extracted from a plant of the Cannabis genus, e.g., Cannabis sativa, Cannabis indica, Cannabis hybrid, or other genera, using any suitable technique for separating cannabinoids from the plant.
  • the extract can be obtained using solvent-based extraction.
  • the one or more cannabinoid compounds is or comprises CBG, or a salt, isomer, enantiomer, or optically active derivative thereof. In some embodiments, the one or more cannabinoid compounds is or is comprised in a CBG distillate. In some embodiments, the one or more cannabinoid compounds is or is comprised in a CBG isolate.
  • the one or more cannabinoid compounds is or comprises CBD, or a salt, isomer, enantiomer, or optically active derivative thereof. In some embodiments, the one or more cannabinoid compounds is or is comprised in a CBD distillate. In some embodiments, the one or more cannabinoid compounds is or is comprised in a CBD isolate.
  • the one or more cannabinoid compounds is or comprises THC, or a salt, isomer, enantiomer, or optically active derivative thereof. In some embodiments, the one or more cannabinoid compounds is or is comprised in a THC distillate. In some embodiments, the one or more cannabinoid compounds is or is comprised in a THC isolate.
  • the emulsion of the application comprises one cannabinoid (single cannabinoid). In some embodiments, the emulsion of the application comprises two or more cannabinoid compounds. In some embodiments, the emulsion of the application comprises two, three, four or more cannabinoid compounds. In some embodiments, the emulsion of the application comprises two cannabinoid compounds. In some embodiments, the emulsion of the application comprises two or more cannabinoid compounds comprised in a distillate, an isolate, cannabis oil, cannabis extract or a combination thereof.
  • the one or more cannabinoid compounds are present in the emulsion in an amount of about 0.25 wt% to about 13 wt% of the emulsion. In some embodiments, the one or more cannabinoid compounds are present in the emulsion in an amount of about 0.25 wt%, about 0.5 wt%, about 1 wt%, about 1 .5 wt%, about 2 wt%, about 4 wt%, about 5 wt%, about 7 wt%, about 8.5 wt% or about 10 wt% and values therebetween.
  • the one or more cannabinoid compounds are present in the emulsion in an amount of about 0.5 wt%. In some embodiments, the one or more cannabinoid compounds are present in the emulsion in an amount of about 1.2 wt%. In some embodiments, the one or more cannabinoid compounds are present in the emulsion at in an amount of about 2.4 wt%. In some embodiments, the one or more cannabinoid compounds are present in the emulsion in an amount of about 5.1 wt%. In some embodiments, the one or more cannabinoid compounds are present in the emulsion in an amount of about 10.2 wt%.
  • the emulsion further comprises one or more terpenes, one or more terpenoids, one or more flavonoids, and any combinations thereof. In some embodiments, the emulsion further comprises one or more terpenes and/or one or more terpenoids.
  • the one or more terpenes and/or one or more terpenoids are selected from abietane, alpha- bisabolol, alphaphellandrene, alpha-pinene, beta-caryophyllene, beta-myrcene, beta-pinene, borneol, cadinene, camphene, camphor, carvacrol, caryophyllene acetate, caryophyllene oxide, cedrane, cembrene, citral, citronellol, copaene, dextro carvone, dextro fenchone, eucalyptol, eugenol, farnesene, gama-3-carene, gamma-terpinene, geraniol, geranyl acetate, guaiazulene, guaiene, humulene, isopulegol, labdane, limonene, linaloo
  • the one or more terpenes and/or one or more terpenoids comprise hemiterpenes, monoterpenols, terpene esters, diterpenes, monoterpenes, polyterpenes, tetraterpenes, terpenoid oxides, sesterterpenes, sesquiterpenes, norisoprenoids, or their derivatives, as well as isomeric, enantiomeric, or optically active derivatives thereof.
  • the derivatives of the one or more terpenes and/or one or more terpenoids comprise terpenoids, hemiterpenoids, monoterpenoids, sesquiterpenoids, sesterterpenoid, sesquarterpenoids, tetraterpenoids, triterpenoids, tetraterpenoids, polyterpenoids, isoprenoids, or steroids.
  • the one or more terpenes and/or one or more terpenoids comprise a-(alpha), p-(beta), y- (gamma), oxo-, isomers, or any combinations thereof.
  • the emulsion further comprises one or more flavonoids selected from bioflavonoids, isoflavonoids and neoflavonoids.
  • the one or more flavonoids are present in the emulsion in an amount of from about 0.00001 wt% to about 0.01 wt%.
  • the one or more terpenes and/or one or more terpenoids are present in the emulsion in an amount of about 0 wt% to about 13 wt% of the emulsion. In some embodiments, the one or more terpenes and/or one or more terpenoids are present in the emulsion in an amount of about 0 to about 0.1 wt%, about 0 to about 0.5 wt%, about 0.5 to about 1 wt%, about 0 to about 1 wt%, about 0 to about 5 wt%, about 0 to about 12 wt%, about 1 to about 2 wt%, about 2 to about 3 wt%, about 3 to about 4 wt%, about 4 to about 5 wt%, about 5 to about 7.5 wt%, about 5 to about 10 wt% or about 10 to about 12.5 wt%, and values therebetween.
  • the whey protein used in the emulsion of the application is any milk serum protein or protein composition known in the art, including, but not limited to, protein isolate, whey protein concentrate, a-lactalbumin and/or p- lacoglobulin.
  • the whey protein is selected from whey protein isolate, whey protein concentrate, a-lactalbumin and p-lacoglobulin.
  • the whey protein is whey protein isolate.
  • the casein protein used in the emulsion of the application is any casein protein known in the art.
  • the casein protein is selected from a-casein, K-casein, p-casein, b-casein, and their salts, such as sodium, potassium, calcium and ammonium, or mixtures thereof.
  • the casein protein is sodium caseinate.
  • the whey protein is present in the emulsion in an amount of about 0.25 wt% to about 5 wt% of the emulsion. In some embodiments, the whey protein is present in the emulsion in an amount of about 0.5 wt%, about 1 wt%, about 1 .25 wt%, about 1 .5 wt%, about 1 .8 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, about 4.5 wt% or about 5 wt% and values therebetween.
  • the whey protein is present in the emulsion in an amount of about 0.5 wt%. In some embodiments, the whey protein is present in the emulsion in an amount of about 1 .3 wt%. In some embodiments, the casein protein is present in the emulsion in an amount of about 3 wt%.
  • the casein protein is present in the emulsion in an amount of about 0.25 wt% to about 5 wt% of the emulsion. In some embodiments, the casein protein is present in the emulsion in an amount of about 0.5 wt%, about 1 wt%, about 1.25 wt%, about 1.5 wt%, about 1.8 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, about 4.5 wt% or about 5 wt% and values therebetween. In some embodiments, the casein protein is present in the emulsion in an amount of about 0.5 wt%. In some embodiments, the casein protein is present in the emulsion in an amount of about 1 .3 wt%. In some embodiments, the casein protein is present in the emulsion in an amount of about 3 wt%.
  • the weight ratio of casein protein to whey protein is about 10:1 to about 1 :10. In some embodiments, the weight ratio of casein protein to whey protein is about 6:1 to about 1 :6, about 3:1 to about 1 :3, about 2:1 to about 1 :2 or about 1 :1. In some embodiments, the weight ratio of casein protein to whey protein is about 6:1 to about 1 :6. In some embodiments, the weight ratio of casein protein to whey protein is 1 :1 .
  • the whey protein is present in the emulsion in an amount of about 1.3 wt% and the casein protein is present in the emulsion in an amount of about 1 .3 wt%.
  • the water is present in the emulsion of the application in an amount of about 65 wt% to about 80 wt% of the emulsion. In some embodiments, the water is present in the emulsion of the application in an amount of about 68 wt%, about 70 wt%, about 73 wt%, about 75 wt%, or about 78 wt% and values therebetween.
  • the oil which is used in the emulsion of the application includes any oil used in food, pharmaceutical or cosmetic industries.
  • the oil is an edible oil.
  • the oil is extracted from any appropriate source such as a marine animal, plant, phytoplankton or algae including microalgae, or may be produced synthetically.
  • the oil can be used in nonpurified, purified or highly purified form, concentrated or non-concentrated. The oil aids in the dissolution of the cannabinoid or cannabis derived compound and allows for emulsification of the cannabinoid and cannabis-derived compounds.
  • the oil is an omega-3 oil.
  • the oil contains omega-3 fatty acids or omega-3 fatty acid precursors such as a- linolenic acid.
  • the fatty acids that are present in the omega-3 oil are selected from one or more of all-cis-7,10,13-hexadecatrienoic acid; a-linolenic acid (ALA) (all-cis-9,12,15-octadecatrienoic acid); stearidonic acid (SDA) (all-cis- 6,9,12,15-octadecatetraenoic acid); eicosatrienoic acid (ETE) (all-cis- 11 ,14,17- eicosatrienoic acid); eicosatetraenoic acid (ETA) (all-cis-8,11 ,14,17-eicosatetraenoic acid); eicosapentaenoic acid (EPA) (all-
  • the omega-3 is selected from oils obtained from fish such as salmon, tuna, herring, mackerel, anchovies, sardines, pollock, cod, catfish, flounder, grouper, halibut, mahi mahi, orange roughy, red snapper, shark, swordfish, tilefish, plankton, algae, krill and/or green-lipped mussel, and/or plant oils such as canola oil, borage oil, evening primrose oil, safflower oil, sunflower oil, flaxseed oil, wheat germ oil, algal oil, and/or grapeseed oil and oils obtained from chia seeds, kiwifruit seeds, perilla seeds, lingonberry seeds, camelina seeds, purslane seeds, black raspberry seeds, hemp seeds, butternut, walnuts, pecan nuts, and/or hazel nuts.
  • the oil is sunflower oil.
  • the oil is algal oil.
  • the oil is present in the emulsion of the application in an amount of about 8 wt% to about 30 wt% of the emulsion. In some embodiments, the oil is present in the emulsion of the application in an amount of about 8 wt%, about 10 wt%, about 15 wt%, about 20 wt%, about 25 wt% or about 30 wt% and values therebetween. In some embodiments, the oil is present in the emulsion of the application in an amount of about 20 wt%. [00164] In some embodiments, the weight ratio of oil to one or more cannabinoid compounds is about 100:1 to about 1 :1. In some embodiments, the weight ratio of oil to at least one cannabinoid or cannabis derived compound is about 80:1 , about 20:1 , about 7:1 , about 2:1 , or about 1 :1.
  • the emulsion further comprises one or more pH adjusting agents selected from sodium acetate, phosphoric acid, acetic acid, lactic acid, fumaric acid, adipic acid, malic acid, tartaric acid, citric acid, hydrochloric acid, sulfuric acid, potassium hydroxide, salts thereof, and combinations thereof.
  • the one or more pH adjusting agents comprise citric acid and potassium hydroxide.
  • the citric acid is anhydrous citric acid.
  • the one or more pH adjusting agents are present in the emulsion of the application in an amount of about 0.1 wt% to about 5 wt% of the emulsion. In some embodiments, the one or more pH adjusting agents are present in the emulsion of the application in an amount of about 0.5 wt%, about 1 wt%, about 2 wt%, about 2.5 wt%, about 3 wt%, about 3.5 wt%, about 4 wt%, or about 4.5 wt% and values therebetween. In some embodiments, the one or more pH adjusting agents are present in the emulsion of the application in an amount of about 0.9 wt%.
  • the emulsion further comprises one or more antifoaming agents.
  • the anti-foaming agents which can be used in the method of the application are any anti-foaming agents known in the art. Examples include, but are not limited to polydimethylsiloxane, fatty acid ester, silicon dioxide, vegetable oil based anti-foaming agents and the like.
  • the one or more anti-foaming agents are present in the emulsion of the application in an amount of about 0.005 wt% to about 0.1 wt % of the emulsion. In some embodiments, the one or more anti-foaming agents are present in the emulsion of the application in an amount of about 0.01 wt%, about 0.05 wt%, or about 0.08 wt% and values therebetween. In some embodiments, the one or more anti-foaming agents are present in the emulsion in an amount of about 0.01 wt%.
  • the emulsion of the application has an average particle size of below about 1000 nm. In some embodiments, the emulsion of the application has an average particle size of about 50 nm to about 900 nm, about 50 nm to about 800 nm, about 50 nm to about 700 nm, about 50 nm to about 600 nm, about 50 nm to about 500 nm, about 50 to about 400 nm, about 50 nm to about 300 nm, or about 900 nm, about 800 nm, about 700 nm, about 600 nm, about 500 nm, or about 400 nm and values therebetween. In some embodiments, the particle size is determined using dynamic light scattering method.
  • the protein complex which is adsorbed at the oil-water interface, greatly improves the stability of the emulsion of the application and protects the one or more cannabinoid compounds of the application from exposure to oxidants and pro-oxidants.
  • Pro-oxidants such as metal ions, are able to lower the activation energy for the initiation of oxidation.
  • Some of these metal ions are bound by the protein complexes, which reduces their negative impact on the oxidation of the one or more cannabinoid compounds.
  • the emulsion of the application is a stable oil-in- water emulsion. In some embodiments, the emulsion of the application is stable at room temperature for at least two weeks or for at least three weeks. Thus, the emulsion of the applications remains free from degradation of the one or more cannabinoid compounds of the application and maintains homogeneous content and appearance. Determination whether an emulsion has lost its stability may be carried out by any of the following techniques: measurement of particle size, zeta potential, light scattering, focused beam reflectance measurement, centrifugation, rheology, potency analysis of the cannabinoids and other active ingredients, assessment of visual appearance or a combination thereof.
  • the emulsion of the application has zeta potential of above about 30 mV. In some embodiments the emulsion of the application has zeta potential of above about 33 mV, above about 35 mV, above about 40, or above about 45 mV. In some embodiments, the emulsion of the application has zeta potential of between about 40 mV to about 50 mV.
  • the present application also includes an emulsion of the application prepared by the method of the application.
  • the method of the application further comprises heat treating or sterilizing the emulsion of the present application.
  • the emulsion is sterilized by ultra-high temperature (UHT) (e.g. 140° C. for 5 seconds).
  • UHT ultra-high temperature
  • the emulsion is pasteurized (e.g. 70° C. for 30 minutes).
  • the emulsion is retorted (e.g. heated in a sealed container at 120° C. for 20 minutes).
  • the emulsion of the application has the advantage that it is resistant to oxidation, has a long shelf-life and/or is stable at high temperature processing, thus allowing it to be heat-treated or sterilized. This is of great benefit as it allows the encapsulated one or more cannabinoid compounds of the application to be added to products that must be sterilized before consumption.
  • the application provides convenient formulations of cannabinoid compounds useful for enhancing or creating aqueous soluble cannabinoid compositions.
  • the emulsion of the application may be useful, for example, to prepare compositions selected from a beverage, gel, gelatin and concentrate and as a beverage enhancer. As such, the emulsion of the application is for use in compositions selected from beverages, gels, gelatins and concentrates and as a beverage enhancer.
  • the application also includes a method of making a liquid composition of the application comprising the emulsion of the present application comprising: diluting the emulsion of the application with a suitable liquid to form the composition.
  • the liquid composition of the application is homogeneous.
  • the liquid composition of the application is an emulsion.
  • any dispersion/solubilization methods known in the art may be used.
  • the liquid used for dilution is selected from liquid selected from water, oil, alcohol, non-alcoholic drink, soft drink, fruit juice, vegetable juice, tea, coffee, milk and punch.
  • the present application also includes a method of making a dry powder composition of the application comprising drying the emulsion of the application to form a powder.
  • the emulsion is dried by spray-drying.
  • Alternative methods include, but are not limited to, pan coating, airsuspension coating, centrifugal extrusion, vibrational nozzle technique, freeze-drying or using a food dehydrator.
  • the application further includes a powder obtained by drying the emulsion of the present application.
  • the resulting powder composition is mixed in a suitable liquid, solid, gel, cream, paste, or any other form, for administration to subjects.
  • the powder composition is prepared and packaged using any packaging known in the art.
  • the powder composition is packaged as a single serving or multiple servings in a metal, glass, or plastic container.
  • the powder composition may be packaged as a single serving stick pack or pouch.
  • the emulsion of the application has the advantage that it is, for example, resistant to oxidation, has a long shelf-life and is stable at high temperature processing, thus allowing it to be heat-treated or sterilized. This is of great benefit as it allows the encapsulated cannabinoid compounds of the application to be added to products that must be sterilized before consumption. Further, the present application provides convenient formulations of cannabinoid compounds useful for enhancing or creating aqueous soluble cannabinoid compositions.
  • the emulsion of the application may be useful, for example, to prepare compositions selected from a beverage, gel, gelatin and concentrate and as a beverage enhancer. As such, the present application includes a use of the emulsion of the application in compositions selected from beverages, gels, gelatins and concentrates and use as a beverage enhancer.
  • the present application also includes a method of reducing the incidence and/or severity of a disease, disorder or condition in a subject comprising administering a composition of the application to a subject in need thereof.
  • the application also includes a use of a composition of the application to reduce the incidence and/or severity of a disease, disorder or condition.
  • the compositions of the application improve resistance to the disease, disorder or condition and/or improve immune response.
  • the compositions of the application maintain or promote health, including nutrient structure-function and quality of life, so that the disease, disorder or condition is improved or not worsened.
  • the compositions of the application relieve symptoms of the disease, disorder or condition.
  • the methods and the uses of the application improve resistance to the disease, disorder or condition and improve immune response relative to otherwise the same conditions in a subject, except that the subject is not administered a composition of the application.
  • the methods and the uses of the application maintain or promote health, including nutrient structure-function, to support the subject’s body’s own ability to resist the disease, disorder or condition and/or improve immune response.
  • the methods and uses of the application improvesquality of life or relieves symptoms of the disease, disorder or condition.
  • the disease, disorder or condition is pain or inflammation or a combination thereof, or any disease, disorder or condition that results from pain or inflammation, or a combination thereof.
  • the compositions of the application reduce the incidence and/or severity of a disease, disorder or condition in a subject by improving the overall health of a subject for example by supporting the subject’s body’s own ability to reduce pain and/or inflammation.
  • the disease, disorder or condition is Alzheimer's disease; Parkinson's disease; essential tremor; amyotrophic lateral sclerosis (ALS); Huntington's disease; Friedreich's ataxia; multiple sclerosis; frontotemporal dementia; prion disease; Lewy body dementia; progressive supranuclear palsy; vascular dementia; normal pressure hydrocephalus; traumatic spinal cord injury; human immunodeficiency virus (HIV) dementia; alcohol induced neurotoxicity; Down's syndrome; movement disorders ofthe central and/or peripheral nervous system; motor neurone diseases (MND); spinal muscular atrophy; or any other related neurological or psychiatric neurodegenerative disease; brain damage; brain injury; brain dysfunction; dysgraphia; dysarthria; apraxia; agnosia; amnesia; dizziness; vertigo; coma; stroke; spinal cord damage; spinal cord injury; spinal cord disorders; central neuropathy; peripheral neuropathy; cranial nerve disorder; trigeminal neural
  • the subject is a mammal. In some embodiments, the subject is human.
  • the disease, disorder or condition is joint pain. In some embodiments, the disease, disorder or condition is inflammatory pain. In some embodiments, the disease, disorder or condition is osteoarthritic pain.
  • the methods and uses of the application reduce the intensity or duration of pain or eliminate the pain in a subject in need thereof.
  • the methods and uses of the application provide improved bioavailability of the one or more cannabinoid compounds and fast pain relief.
  • the methods and uses of the application achieve reduced pain intensity for at least 4 hours, at least 6 hours, at least 8 hours, at least 12 hours, at least 18 hours, or at least 24 hours post administration.
  • Treatment methods of the application comprise administering to a subject a therapeutically effective amount of a composition of the application and optionally administered once, twice, three, or four times a day, or as needed.
  • the composition of the application is administered orally.
  • the composition of the application is administered in a liquid form.
  • the liquid form is a solution, suspension or emulsion.
  • the particle size was determined using dynamic light scattering (DLS) method.
  • the sample was diluted 1 :2500 with acidic water solution (the solution was prepared by adding anhydrous citric acid to Type 1 deionized water to obtain pH 3.2).
  • the test was performed according to Anton Paar Litesizer500 instructions, and further dilutions were performed as needed and indicated by the instrument.
  • CBG isolate CBG isolate, sunflower oil, omega 3, water, whey protein, sodium caseinate, KOH, citric acid, anti-foaming agent.
  • the process developed by the Applicant included: 1) mixing caseinate protein and whey protein complex in water and allowing dissolution at room temperature for about 1 hour; 2) adjusting the pH with KOH to 6.5-8; 3) heating the aqueous solution of casein protein and whey protein at about 90 °C for 5 to 10 min; 3) cooling the protein complex solution to about 10 °C; 4) adjusting the pH of the protein complex solution with citric acid anhydrous to pH of about 3.2; 5) adding oil to the protein complex solution under high shear mixing (handheld, 12-15 krpm for 3 min.) 6) heat treating the mixture at 95 °C for 3 sec. ; and 7) homogenizing the mixture in two stages using a microfluidizer at 3000 psi and 500 psi pressure.
  • the target particle size should be in the nano range (sub-micron); close to 500 nm.
  • the target zeta potential should optimally be more than 30 mV (or less than -30 mV).
  • Zeta potential is an indicator of stability of the colloidal system. Colloids with zeta potential of more than 30 mV (or less than -30 mV) are repelled from one another and remain well dispersed or easily redispersed in solution. As shown in Table 4 and Table 5, all trials resulted in particle size relatively close to 500 nm and zeta potential greater than 30 mV. Therefore, it was demonstrated that the emulsion had successfully been recreated.
  • Particle size of the initial batch emulsions was measured at 8 and 18 days. There was no visible phase separation seen in any of the emulsions throughout the duration of the testing.
  • Particle size for each emulsion remained in the nano range; all under 750 nm except the 3000 psi 1 st pass sample. Visible mold/bacteria began to form after the 18-day mark interfering with particle size measurements and subsequent testing was not performed.
  • the emulsions had only slight increase in particle size after one week with an increase of less than 150 nm.
  • the emulsions were to be monitored for another week however similarly to the initial batch, mold/bacteria began to grow after the 7-day mark, interfering with any future particle size measurements.
  • a pasteurization step was added for all future emulsions to mitigate microbial growth.
  • a dilution of each emulsion sample was performed for analysis to reduce the density of particles to measure laser light scattering angles through the solution.
  • a low concentration pH citrate buffer was employed to avoid destabilization of the colloids during the test procedure.
  • Various buffer concentrations were prepared to investigate the effect of ionic strength and pH on particle size measurement.
  • LC-NPMC-2022-04-18-1 -B&B that was submitted to 10,000 psi and 2 passes also showed little variation across all of the buffer solutions except for one outlier with the diluent of 50 mM and a pH of 3.15.
  • LC-NPMC-2022-04-18-1 -B&B was stored overnight in the diluent and tested again the next day. Testing the next day revealed a slight increase in particle size.
  • DOE emulsion stability
  • a half factorial DOE design was chosen varying four parameters (whey, casein, microfluidizer pressure and the presence of KOH) while keeping the remaining parameters the same as the original tech transfer batches. It was decided that a resolution of IV was acceptable to be able to grasp the effect of the parameters on the final emulsion, resulting in a total of eight experiments. A resolution of IV allowed the estimation of main effects caused by parameters unconfounded by two-factor Interactions.
  • the DOE batches were created over the course of two days, formulated in the same order as listed in Table 8.
  • the initial protocol included the use of an overhead mixer to create a coarse emulsion, however, this method of mixing did not provide enough shear force to make the input coarse emulsion.
  • a planned deviation to the protocol was documented to include the use of a blender.
  • the amount of citric acid required to acidify the solution was more when compared to the other batches, with approximately 9 g being added.
  • the viscosity of batches was higher than the tech transfer batches, making the batches difficult to work with and process through the microfluidizer.
  • the lack of potassium hydroxide did not appear to add to the difficulty of dissolving the proteins and did not contribute to an increase in production time.
  • CBG Cannabigerol
  • Emulsions containing CBG isolate were created to investigate the effect of the presence of cannabinoids on emulsion stability.
  • An anti-foaming agent was also added to minimize the foaming of proteins during emulsion processing.
  • a total of 4 batches were created, varying the composition as shown in the tables below.
  • Table 18 Emulsion Composition of 20Jul2022-Batch1
  • Table 20 Emulsion Composition of 20Jul2022-Batch3
  • Table 21 Emulsion Composition of 20Jul2022-Batch4
  • CBG was dissolved in sunflower oil via mechanical stirring using a stirring bar. Upon even dispersion of the isolate solids, the mixture was placed in an ultrasonic bath at 80 kHz at 100 % power for 10 minutes to ensure the mixture was homogenous.
  • the second CBG batches were created to determine if the CBG containing emulsion is stable.
  • a secondary objective of the batches was to use a new brand of sodium caseinate and to ensure that stability was not affected with the new product.
  • Table 25 Emulsion Composition of 11Aug2022-Batch3
  • Table 26 Particle Size and Zeta Potential Results from CBG Batches Made August 11 , 2022
  • the method entails the extraction of the emulsion using first a mixture of chloroform and methanol, followed by two subsequent extractions with chloroform and then with water. The solution was then centrifuged to separate the aqueous and organic layers with a layer of proteins in between.
  • the potency analysis method was validated for selectivity, recovery, and repeatability.
  • An assay was also run on the CBG isolate to test for purity.
  • the selectivity was verified by ensuring the resolution between the CBG and Cannabigerolic acid (CBGA) peaks were greater than one.
  • Recovery was accessed based on the amount of CBG that was quantified from placebo emulsions spiked with a known amount of CBG.
  • the repeatability of the method was evaluated by verifying the %RSD of three spiked emulsions was less than two percent.
  • the standard used for the quantification of cannabinoids in the emulsion was a combination of CBG and CBGA single component standards, made to a concentration of 50 ppm for each component.
  • T able 27 Peak Areas of CBG Vs CBG + CBGA
  • Placebo emulsion samples were tested to determine if there was any interference in the chromatogram caused by the sample matrix. Negative control samples were found to have no considerable matrix interference, as can be seen in Figure 8, with no visible peaks being present.
  • the CBG containing emulsions were tested to determine the recovery of the method as well as the reproducibility of the overall extraction and potency determination.
  • the maximum possible concentration of the CBG containing emulsion is -12.43 mg of CBG per gram of oil, according to the master batch record.
  • the recovery of CBG from the emulsions was determined to be -94.3 % as can be seen in Table 28.
  • the spiked placebo emulsions were tested according to the extraction method in order to estimate the recovery of the method. As can be seen in Table 29, the recovery of CBG from the spiked emulsions was found to be higher than expected. This is likely due to the concentration of CBG in the oil not being known with certainty. The concentration of CBG to oil was estimated based on the oil added during emulsion preparation. This could be rectified by exploring a different method for spiking where the amount of oil into which the CBG isolate is being spiked is known.
  • the CBG concentrations were varied to simulate a beverage containing 50 mg, 100 mg, 210 mg and 420 mg respectively. This is to say that the beverages would contain 50, 100, 210, and 420 mg per beverage if the emulsions were to be diluted in the final beverage.
  • the 50 to 210 mg batches were made successfully without the need for added sonication.
  • the 420 mg batch was not successful as the amount of CBG could not be fully dissolved in the oil.
  • a deviation from the procedure was documented to include pasteurization (in glass bottles) at 70 °C for 30 minutes. Pasteurization was successful; there was no visible bacterial growth after two weeks.
  • Table 34 Particle Size and Zeta Potential Data for Load Study Emulsions Collected over Two Weeks [00237] Particle size and zeta potential were monitored for all three concentrations as shown in T able 34 for a period of almost three weeks stored at 25°C. Particle size for all three batches remained stable, with all samples varying less than 60 nm from the initial measurement. Zeta potential remained at the desired target of > 30 mV, indicating emulsion stability. A visual inspection concluded that there was no creaming or separation observed. The emulsions maintained homogeneous appearance over the study period.
  • the emulsion was prepared containing 3% sodium caseinate, 3% whey protein, 0.58% citric acid, 15% omega-3 oil, 0.02% anti-foaming agent, and the remainder was water. 10% KOH solution was used in an amount appropriate to achieve pH of 7.5-8 in the aqueous solution of casein protein and whey protein complex.
  • the emulsion was sampled after pasteurization and was tested for stability in the stability chamber at 25°C/60% relative humidity (RH) and at 4°C to gather information from both conditions. All samples were initially subjected to 24 hours of 25°C/60%RH conditions. rnnoziii Particle Size & Zeta Potential
  • Table 38 Particle size and zeta potential for samples stored for four weeks under 25 °C and 4 °C
  • the emulsion displayed good zeta potential values across the 4-week duration under both storage conditions. It can be seen in Table 38 that all zeta potential values are >
  • the method for cannabinoid potency analysis was validated by testing for selectivity, recovery, and repeatability.
  • An extraction method known as the Bligh and Dyer method was implemented for recovering the CBG containing oil from the emulsion.
  • An omega-3 rich, algal based oil was incorporated into the formulation and was demonstrated to create a successful emulsion using this ingredient.
  • a CBG load study resulted in excellent particle size and zeta potential data for every concentration tested.
  • the potency analysis of the load study emulsions demonstrated reduced potency retention in emulsions with higher CBG concentrations.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Mycology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Molecular Biology (AREA)
  • Dispersion Chemistry (AREA)
  • Biophysics (AREA)
  • Rheumatology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Botany (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)

Abstract

La demande concerne des émulsions, en particulier des émulsions de cannabinoïdes, et leurs procédés de fabrication. La demande concerne également un procédé d'utilisation des émulsions pour préparer une composition pour traiter des maladies, des troubles ou des états qui sont traitables ou bénéficient de l'utilisation de cannabinoïdes. Les émulsions comprennent facultativement des terpènes.
PCT/CA2024/051049 2023-08-10 2024-08-09 Émulsion de cannabinoïdes Pending WO2025030248A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363531864P 2023-08-10 2023-08-10
US63/531,864 2023-08-10

Publications (1)

Publication Number Publication Date
WO2025030248A1 true WO2025030248A1 (fr) 2025-02-13

Family

ID=94533167

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA2024/051049 Pending WO2025030248A1 (fr) 2023-08-10 2024-08-09 Émulsion de cannabinoïdes

Country Status (1)

Country Link
WO (1) WO2025030248A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA3026402A1 (fr) * 2017-12-05 2019-06-05 James F. Kane Cannabinoides hydrosolubles et methode de fabrication associee
WO2020037408A1 (fr) * 2018-08-20 2020-02-27 Hexo Operations Inc. Produit à base de cannabis ayant une expérience utilisateur de profil cannabinoïde contrôlée
WO2023070170A1 (fr) * 2021-10-29 2023-05-04 Aquila Black Limited Compositions de cannabinoïdes dispersibles dans l'eau

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA3026402A1 (fr) * 2017-12-05 2019-06-05 James F. Kane Cannabinoides hydrosolubles et methode de fabrication associee
WO2020037408A1 (fr) * 2018-08-20 2020-02-27 Hexo Operations Inc. Produit à base de cannabis ayant une expérience utilisateur de profil cannabinoïde contrôlée
WO2023070170A1 (fr) * 2021-10-29 2023-05-04 Aquila Black Limited Compositions de cannabinoïdes dispersibles dans l'eau

Similar Documents

Publication Publication Date Title
US10285971B2 (en) Formulations of water-soluble derivatives of vitamin E and soft gel compositions, concentrates and powders containing same
US9693574B2 (en) Compositions containing water-soluble derivatives of vitamin E mixtures and modified food starch
CN107080734B (zh) 包含生育酚的peg衍生物的乳剂
CN105228470B (zh) 维生素e水溶性衍生物制剂及包含其的组合物
CN104114038B (zh) 乳剂组合物以及包含其的组合物
JP5070203B2 (ja) 甘草ポリフェノール製剤
CA3143118A1 (fr) Extraction eutectique de solides
EP3886910A1 (fr) Compositions comprenant un cannabinoïde ou un composé dérivé du cannabis, méthodes de fabrication et d'utilisation
CA3038473A1 (fr) Formulations diluables de cannabinoides et leurs procedes de preparation
US8785598B2 (en) Coenzyme Q10 nanoparticles, preparation method thereof and composition containing said nanoparticles
TW201139652A (en) Thermally stable oil-in-water emulsions containing an oil that contains polyunsaturated fatty acids
JP2021177782A (ja) 水中油型乳化組成物、並びに、これを含む食品及び飲料
WO2006035900A1 (fr) Préparation émulsifiée contenant la coenzyme q10
US20210307349A1 (en) Formulations of phospholipid comprising omega fatty acids
EP1583433B1 (fr) Preparations contenant des phospholipides polyinsatures, des monoterpenes et des derives du tryptophane et/ou du phytol
EP3762006B1 (fr) Huile de krill pour solubiliser des compléments alimentaires peu solubles dans l'eau et des agents pharmaceutiquement actifs
US11173127B2 (en) Potato protein nanoparticles
WO2025030248A1 (fr) Émulsion de cannabinoïdes
EP4164615A1 (fr) Compositions d'apport d'agents thérapeutiques, leurs méthodes d'utilisation et leurs procédés de préparation
CA3160751A1 (fr) Composition enrichie en canabinoides et procede d'utilisation
JP6752012B2 (ja) テルペノイド減少抑制剤
JP2007016000A (ja) チオクト酸含有組成物
HK1187213B (en) Non-aqueous pre-emulsion composition and method for preparing a beverage containing a phytosterol
HK1187213A1 (zh) 非水性预乳液组合物及制备包含植物甾醇的饮料的方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 24850424

Country of ref document: EP

Kind code of ref document: A1