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WO2022155757A1 - Systèmes d'émulsification de cannabinoïde contenant des ingrédients naturels pour la fabrication de produits à base de cannabis infusé - Google Patents

Systèmes d'émulsification de cannabinoïde contenant des ingrédients naturels pour la fabrication de produits à base de cannabis infusé Download PDF

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Publication number
WO2022155757A1
WO2022155757A1 PCT/CA2022/050097 CA2022050097W WO2022155757A1 WO 2022155757 A1 WO2022155757 A1 WO 2022155757A1 CA 2022050097 W CA2022050097 W CA 2022050097W WO 2022155757 A1 WO2022155757 A1 WO 2022155757A1
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WO
WIPO (PCT)
Prior art keywords
cannabinoid
emulsification system
amount
saponin extract
cannabis
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Ceased
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PCT/CA2022/050097
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English (en)
Inventor
Justin CONWAY
Jamie SAVARD
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Hexo Operations Inc
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Hexo Operations Inc
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Publication date
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Publication of WO2022155757A1 publication Critical patent/WO2022155757A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A23D7/0053—Compositions other than spreads
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS OR COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/02—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by the production or working-up
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00—Tea; Tea substitutes; Preparations thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F5/00—Coffee; Coffee substitutes; Preparations thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K50/00—Feeding-stuffs specially adapted for particular animals
    • A23K50/40—Feeding-stuffs specially adapted for particular animals for carnivorous animals, e.g. cats or dogs
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/38—Other non-alcoholic beverages
    • 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
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients
    • 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
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/05—Phenols
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • 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
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/348—Cannabaceae
    • A61K36/3482—Cannabis
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans

Definitions

  • the present disclosure generally relates to the field of cannabinoid emulsification systems which are suitable for manufacturing cannabis-infused products, particularly cannabis- infused products that include an aqueous component.
  • Emulsification systems that include one or more emulsifiers to generate the emulsion necessary to solubilize the lipophilic cannabis extracts into cannabis- infused products that include an aqueous component.
  • Emulsification systems often make use of synthetic or semi-synthetic emulsifiers, which may or may not have been approved as food additives in jurisdictions of commercial interest, thus limiting their industrial scale usefulness.
  • the use of synthetic or semi-synthetic emulsifiers may also contribute to reducing the perceived naturalness of a cannabis-infused products such that consumers, because of safety, health or other concerns, may demonstrate a reluctance to accept and consume such cannabis-infused products.
  • the present inventors have developed a cannabinoid emulsification system for making cannabis-infused products, particularly cannabis-infused products that include an aqueous component.
  • the system advantageously generates stable emulsion particles in the nanoscale sizes and includes natural emulsifier ingredients.
  • the present disclosure relates to a cannabinoid emulsification system that generates a nanoemulsion with a particle size distribution of about 135 nm or less.
  • the cannabinoid emulsification system comprises a) a saponin extract as emulsifier, b) ethanol as co-emulsifier, and c) a cannabinoid component including a cannabinoid.
  • the cannabinoid emulsification system may have one or more of the following features:
  • the particle size distribution is from about 90 nm to about 130 nm, or from about 90 nm to about 120 nm, or from about 100 nm to about 120 nm.
  • the nanoemulsion has a % polydispersity (%PD) of from about 5% to about 20 %.
  • the saponin extract is in an amount of about 0.5 wt.% or more, or from about 0.5 wt.% to about 3.0 wt.%, (dry basis) - the percentage is expressed relative to the weight of the cannabinoid emulsification system.
  • the saponin extract includes saponins in an amount of about 20 wt.% or more (dry basis), or from about 50 wt.% and about 95 wt.% (dry basis).
  • the saponin extract is in the form of a saponin extract aqueous solution and comprises saponins in an amount of from about 10 wt.% to about 20 wt.% (wet basis).
  • the saponin extract aqueous solution is present in an amount such that there is a ratio of the amount of the saponin extract aqueous solution to an amount of the cannabinoid component of from about 1.25:1 to about 15:1.
  • the ratio of the amount of the saponin extract aqueous solution to the amount of the cannabinoid component is of about 1.25:1.
  • the saponin extract is a Type 2 saponin extract.
  • the saponin extract is a Quillaja saponin extract.
  • ethanol as co-emulsifier is present in an amount of about 1 wt.% or more, or from about 1 wt.% to about 30 wt.%, or from about 5 wt.% to about 15 wt.%, or from about 10 wt.% to about 15 wt.% - the percentage is expressed relative to the weight of the cannabinoid emulsification system.
  • the cannabinoid component is present in an amount of about 1 wt.% or more, or from about 1 wt.% to about 25 wt.%, or about 15 wt.% or less, or about 5 wt.% - the percentage is expressed relative to the weight of the emulsification system.
  • the cannabinoid emulsification system comprising the cannabinoid in a concentration of about 0.001 mg/mL or more, or from about 0.001 mg/mL to about 100 mg/mL.
  • the cannabinoid includes cannabidiol (CBD), tetrahydrocannabinol (THC), or any combination thereof.
  • the cannabinoid component further comprises a carrier oil, a terpene, or any combination thereof.
  • the cannabinoid component comprises the carrier oil in an amount such that there is a ratio of the amount of the carrier oil to an amount of the cannabinoid of from about 1.6:1 to about 1:0, or about 2:1.
  • the carrier oil comprises a medium chain triglyceride (MCT).
  • MCT medium chain triglyceride
  • the nanoemulsion has a pH of about 7 or less.
  • cannabinoid emulsification system consists essentially of natural ingredients.
  • cannabinoid emulsification system is in the form of an emulsion.
  • cannabinoid emulsification system is in the form of a nanoemulsion.
  • the present disclosure relates to a method of manufacturing a cannabinoid emulsification system.
  • the method comprises: a) providing an oil phase comprising a cannabinoid component including a cannabinoid, b) providing an aqueous phase, wherein a saponin extract as an emulsifier and ethanol as a co-emulsifier are independently incorporated in the oil phase or in the aqueous phase, and c) mixing the oil phase with the aqueous phase and forming the cannabinoid emulsification system, the cannabinoid emulsification system generating a nanoemulsion having a particle size of about 135 nm or less.
  • the method of manufacturing the cannabinoid emulsification system may have one or more of the following features:
  • • generating the nanoemulsion comprises homogenizing the cannabinoid emulsification system, preferably with a valve homogenizer.
  • homogenizing the cannabinoid emulsification system includes homogenizing the cannabinoid emulsification system with a valve homogenizer performing less than 3 passes, or less than 2 passes on the valve homogenizer.
  • the nanoemulsion has a particle size distribution of from about 90 nm to about 130 nm, or from about 90 nm to about 120 nm, or from about 100 nm to about 120 nm.
  • the nanoemulsion has a % polydispersity (%PD) of from about 5% to about 20 %.
  • the saponin extract is present in an amount of about 0.5 wt.% or more, or from about 0.5 wt.% to about 3.0 wt.%, (dry basis) - the percentage is expressed relative to the weight of the cannabinoid emulsification system.
  • the saponin extract includes saponins in an amount of about 20 wt.% or more, or from about 50 wt.% and about 95 wt.% (dry basis).
  • the saponin extract is in the form of a saponin extract aqueous solution and comprises comprising saponins in an amount of from about 10 wt.% to about 20 wt.% (wet basis).
  • the saponin extract aqueous solution is present in an amount such that there is a ratio of the amount of the saponin extract aqueous solution to an amount of the cannabinoid component of from about 1.25: 1 to about 15: 1 , or about 1.25:1.
  • the saponin extract is a Type 2 saponin extract.
  • the saponin extract is a Quillaja saponin extract.
  • ethanol as co-emulsifier is present in an amount of about 1 wt.% or more, or from about 1 wt.% to about 30 wt.%, or from about 5 wt.% to about 15 wt.%, or from about 10 wt.% to about 15 wt.% - the percentage is expressed relative to the weight of the cannabinoid emulsification system.
  • the cannabinoid component is present in an amount of about 1 wt.% or more, or from about 1 wt.% to about 25 wt.%, or about 15 wt.% or less, or about 5 wt.% - where the percentage is expressed relative to the weight of the emulsification system.
  • the cannabinoid is present in a concentration of about 0.001 mg/mL or more, or from about 0.001 mg/mL to about 100 mg/mL.
  • the cannabinoid includes cannabidiol (CBD), tetrahydrocannabinol (THC), or any combination thereof.
  • the cannabinoid component further comprises a carrier oil, a terpene, or any combination thereof.
  • the cannabinoid component comprises the carrier oil in an amount such that there is a ratio of the amount of the carrier oil to an amount of the cannabinoid of from about 1.6:1 to about 1:0, or about 2:1.
  • the carrier oil comprises a medium chain triglyceride (MCT).
  • MCT medium chain triglyceride
  • the nanoemulsion has a pH of about 7 or less.
  • the present disclosure relates to a cannabinoid emulsification system obtained with the method described herein where the cannabinoid emulsification system generates upon homogenizing a nanoemulsion having a particle size distribution of about 135 nm or less.
  • the present disclosure relates to a cannabis-infused product that comprises the cannabinoid emulsification system described herein.
  • the cannabis-infused product may have one or more of the following features:
  • the cannabis-infused product is a solid or semi-solid edible product.
  • the cannabis-infused product is a liquid product.
  • the cannabis-infused product is selected from a cannabis-infused beverage, spray, tincture or drops.
  • the cannabis-infused beverage is drinking water, milk, juice, a smoothie, coffee or a caffeinated beverage, tea, herbal tea, a cocoa beverage, an energy drink, a drinkable yogurt, a fermented beverage, or an alcoholic or non-alcoholic drink.
  • the alcoholic or non-alcoholic drink is a lager, cider, spirit, wine, or cocktail.
  • the cannabis-infused beverage is a sparkling beverage.
  • the cannabis-infused product comprises at least 0.002 mg/ml of the cannabinoid.
  • a unit of the cannabis-infused product comprises from about 1 mg to about 1000 mg of the cannabinoid.
  • the present inventors have developed a cannabinoid emulsification system for making cannabis-infused products, particularly cannabis-infused products that include an aqueous component.
  • the cannabinoid emulsification system comprises a cannabinoid component that includes a cannabinoid.
  • the cannabinoid emulsification system also comprises a saponin extract as emulsifier and ethanol as co-emulsifier.
  • the cannabinoid emulsification system advantageously generates stable emulsion particles in the nanoscale range while including natural emulsifier ingredients.
  • the herein described cannabinoid emulsification system reproducibly generates a stable emulsion with particle sizes in the nanoscale range.
  • the resulting cannabinoid emulsification system can be used at an industrial scale using significantly less emulsification energy and processing time than with other comparable emulsification systems that include natural emulsifier ingredients but do not have such combination.
  • Such reduction in energy and processing time required for emulsification offers significant benefits from an industrial scale perspective, as it reduces overall cost, increases yield and simplifies the manufacturing process.
  • emulsion refers to a mixture of two or more liquids that are normally immiscible owing to liquid-liquid phase separation, where one liquid (dispersed phase) is dispersed in the form of discreet droplets into the other (the continuous phase). For example, discreet oil droplets dispersed in an aqueous phase.
  • the herein described cannabinoid emulsification system generates a stable nanoemulsion with a particle size of about 135 nm or less.
  • the cannabinoid emulsification system generates a nanoemulsion having a particle size distribution (PSD) of between about 90 nm and about 130 nm, including any amount therebetween or any ranges therein, such as from about 90 nm and about 120 nm, or from about 100 nm to about 120 nm.
  • PSD particle size distribution
  • the expression “the cannabinoid emulsification system generates a nanoemulsion” refers to the concept that upon formulation, the emulsification system can be in the form of an emulsion - where upon further processing with techniques known in the art (e.g., high shear, such as homogenization), one obtains the nanoemulsion described herein.
  • PSD particle size distribution
  • index means of expression
  • volume, area, length, and quantity are used as standards (dimensions) for particle amount.
  • the volume standard is used and expressed as the diameter of the particle.
  • the PSD is a volume-based particle size measured, for example, by dynamic light scattering (DLS) methods. It will be readily appreciated that the PSD of the cannabinoid emulsion system refers to the PSD of the oil droplets that are present in an aqueous solution.
  • the polydispersity index (or “dispersity” as per IIIPAC recommendation) reflects the heterogeneity of the oil droplets sizes within an emulsion, i.e., the PDI gives an indication of the width of the overall distribution, assuming a single mean. For a perfectly uniform sample, the PDI would be 0.0.
  • the cannabinoid emulsification system generates an emulsion having a %PD of about 20% or less.
  • the cannabinoid emulsification system generates an emulsion having a %PD of from about 5% to about 20 %, including any amount therebetween or any ranges therein, such as from about 10% to about 15%.
  • a %PD of about 6%, about 8%, about 10%, about 12%, about 14%, about 16%, about 18, or about 20% including any amount therebetween.
  • the emulsification system described herein can be used to infuse a base product to obtain the cannabis-infused product.
  • the emulsification system manufacturer can infuse the base product to obtain the cannabis-infused product, ready for packaging and commercialization.
  • the cannabinoid emulsification system may be packaged and sold to a product manufacturer, which can then use same to infuse the base product to obtain the cannabis-infused product.
  • the cannabinoid emulsification system may be packaged and commercialized alone or together with a base product such that the end-user may use same to infuse the base product and obtain the cannabis- infused product.
  • the term “product base” refers to a composition, which includes an aqueous component and that is used to obtain the herein described cannabis-infused product.
  • the product base may be an ingredient or a mixture of ingredients for making the cannabis-infused product, where the product base includes at least one aqueous component which requires incorporating the cannabinoid therein in the form of an emulsion.
  • the term “cannabis-infused product” refers to commercial solid, semisolid, or liquid products containing a cannabinoid.
  • the cannabis-infused products includes beverages (e.g., alcoholic, non-alcoholic, juices, sparkling water, etc.), non-beverage liquid products (oral sprays, drops, etc.), human edibles (e.g., baked goods, cereals, etc.), pet edibles (e.g., pet food, pet chew, etc.), and/or confections (e.g., lozenges, chewing gum, mints, chocolates, candies, gummies, etc.), which include at least one aqueous component thus requiring an emulsification system to infuse the cannabinoid.
  • beverages e.g., alcoholic, non-alcoholic, juices, sparkling water, etc.
  • non-beverage liquid products oral sprays, drops, etc.
  • human edibles e.g., baked goods, cereals, etc.
  • pet edibles e.g., pet
  • the cannabinoid emulsification system comprises a saponin extract as emulsifier.
  • Saponins are natural surfactants with lipophilic aglycone and hydrophilic glycosyl groups. Differences in the aglycone structure and the glycosyl groups can be used to classify various saponins types.
  • the saponin extract is a food grade saponin extract.
  • the saponin extract is a plant material saponin extract.
  • the saponin extract can be an extract from Smilax ornata (sarsaparilla), Gypsophilla paniculata (brides veil), Saponaria officianalis (soap root) or Quillaja saponaria Molina (soap bark), alone or mixed with other low-cost saponin sources (e.g., Yucca shidigera extracts). Manufacturing procedures for obtaining saponin extracts from plant materials are described for example in US 5,057,540 and US 5,817,314, each of which is incorporated herein by reference.
  • Quillaja saponin extracts are approved as food additives and foaming agents in Canada (CFDA Regulation, B.16.100, Table IV S.1) and in the United States (FDA Regulation 21 CFR 172.510, FDA GRAS notification GRN 16, FEMA No. 2973).
  • the saponin extract is obtained by cell culture of Quillaia species, such as Quillaja saponaria, Quillaja smegmadermos or Quillaja brasilensis.
  • Quillaia species such as Quillaja saponaria, Quillaja smegmadermos or Quillaja brasilensis.
  • the cannabinoid emulsification system includes the saponin extract in an amount of about 0.5 wt.% or more (dry basis), where the percentage is expressed relative to the weight of the cannabinoid emulsification system.
  • the cannabinoid emulsification system includes the saponin extract in an amount of from about 0.5 wt.% to about 3 wt.% (dry basis), including any amount therebetween or any ranges therein.
  • the cannabinoid emulsification system includes the saponin extract in an amount of about 0.5 wt.%, about 1 wt.%, about 1.5 wt.%, about 2.0 wt.%, about 2.5 wt.%, or about 3.0 wt.% (dry basis), including any amount therebetween or any ranges therein.
  • the saponin extract is in the form of a saponin extract aqueous solution.
  • the saponin extract aqueous solution may include the saponin extract and water.
  • the saponin extract aqueous solution may further include preservatives.
  • the amount of the saponin extract (dry basis) described above will require adjustments when using a saponin extract aqueous solution instead of a saponin extract per se.
  • a saponin extract aqueous solution containing about 10 wt.% saponins the above discussed amount of saponin extract of from about 0.5 wt.% to about 3.0 wt.% (dry basis) will correspond to an amount of the saponin extract aqueous solution of from about 5 wt.% to about 30 wt.% (wet basis) to take into account the dilution of the saponins.
  • the saponin extract aqueous solution comprises saponins in an amount of from about 10 wt.% to about 20 wt.% (wet basis), including any amounts therebetween or any ranges therein.
  • the saponin extract aqueous solution may include saponins in an amount of from about 13 wt.% to about 16 wt.% (wet basis).
  • the cannabinoid emulsification system includes the saponin extract aqueous solution in an amount such that there is a ratio of the amount of the saponin extract aqueous solution to an amount of the cannabinoid component of from about 1.25:1 to about 15:1, including any amount therebetween or any ranges therein.
  • the ratio of the amount of the saponin extract to the amount of the cannabinoid component is of about 15:1, about 14.9:1, about 14.8:1, about 14.7:1, about 14.6:1, about 14.5:1, about 14.4:1, about 14.3:1, about 14.2:1, about 14.1:1, about 14:1, about 13.9:1, about 13.8:1, about 13.7:1, about 13.6:1, about 13.5:1, about 13.4:1, about 13.3:1, about 13.2:1, about 13.1:1, about 13:1, about 12.9:1, about 12.8:1, about 12.7:1, about 12.6:1, about 12.5:1, about 12.4:1, about 12.3:1, about 12.2:1, about 12.1:1, about 12:1, about 11.9:1, about 11.8:1, about 11.7:1, about 11.6:1, about 11.5:1, about 11.4:1, about 11.3:1, about 11.2:1, about 11.1:1, in some cases 11:1, about 10.9:1, about 10.8:1, about 10.7:1, about 10.6:1, about 10.5:1, about 11.3
  • Saponin extracts are classified as Type 1 and Type 2, which differ in terms of purification steps.
  • Quillaja saponin extracts are traditionally obtained with an aqueous extraction of milled inner bark or wood of pruned stems and branches of Quillaja saponaria Molina tree.
  • Type 1 Quillaja saponin extracts are generally obtained by treating the aqueous extraction with “stabilizing agents”, such as egg albumin and polyvinylpyrrolidone, which are then filtered, for example through diatomaceous earth.
  • Type 1 Quillaja saponin extracts generally contain saponins in an amount of from about 20 wt.% to about 26 wt.% (dry basis).
  • Type 2 Quillaja saponin extracts are generally obtained by subjecting Type 1 saponin extracts to additional purification steps, such as ultra-filtration, membrane filtration or affinity chromatography.
  • Type 2 Quillaja saponin extracts generally contain saponins in an amount of from about 60 wt.% to about 90 wt.% (dry basis).
  • saponins in an amount of from about 60 wt.% to about 90 wt.% (dry basis).
  • the saponin extract includes saponins in an amount of about 20 wt.% or more (dry basis).
  • saponin extract can include saponins in an amount of from about 50 wt.% and about 95 wt.% (dry basis), including any amounts therein between such as from about 60 wt.% to about 90 wt.% (dry basis).
  • the saponin extract can include saponins in an amount of about 20 wt.%, about 25 wt.%, about 30 wt.%, about 35 wt.%, about 40 wt.%, about 45 wt.%, about 50 wt.%, about 60 wt.%, about 70 wt.%, about 80 wt.%, about 90 wt.%, or about 95 wt.% (dry basis).
  • the cannabinoid emulsification system includes a Type 2 saponin extract.
  • the cannabinoid emulsification system includes the commercially available Quillaja saponin extracts Q-NATURALE® from Ingredion.
  • Q-NATURALE includes saponins in an amount of from about 60 wt.% to about 75 wt.% (dry basis) and is available as an aqueous solution containing saponins in an amount of from about 13 wt.% to about 16 wt.% (wet basis).
  • the cannabinoid emulsification system may include one or more other emulsifiers in addition to the above described emulsifier, so long as the one or more other emulsifiers is (are) considered as a “natural” emulsifier.
  • one or more emulsifier such as lecithin, whey, caseinate, and the like.
  • the cannabinoid emulsification system comprises ethanol as co-emulsifier.
  • the cannabinoid emulsification system includes ethanol as co- emulsifier in an amount of about 1 wt.% or more, where the percentage is expressed relative to the weight of the cannabinoid emulsification system.
  • the cannabinoid emulsification system includes ethanol as co-emulsifier in an amount of from about 1 wt.% to about 30 wt.%, including any amount therebetween or any ranges therein, such as from about 5 wt.% to about 15 wt.%.
  • the cannabinoid emulsification system includes ethanol as co-emulsifier in an amount of about 2 wt.%, about 3 wt.%, about 4 wt.%, about 5 wt.%, about 6 wt.%, about 7 wt.%, about 8 wt.%, about 9 wt.%, about 10 wt.%, about 11 wt.%, about 12 wt.%, about 13 wt.%, about 14 wt.%, about 15 wt.%, about 16 wt.%, about 17 wt.%, about 18 wt.%, about 19 wt.%, about 20 wt.%.
  • the cannabinoid emulsification system includes ethanol as co- emulsifier in an amount of from about 10 wt.% to about 15 wt.%.
  • Emulsification of cannabinoids when manufacturing cannabis-infused products at an industrial scale may typically involve processes that are known to those of skill in the art, such as homogenization, high energy ultrasonication, and the like.
  • the emulsification process may also be assisted or accelerated by the application of heat (e.g., through microwave irradiation).
  • heat e.g., through microwave irradiation
  • the emulsification system described herein generates the herein described nanoemulsion.
  • emulsification system is different from known self-emulsification system that generate a nanoemulsion (e.g., as described in WO 2021/119844), where in the process of self-emulsification, nano size drops of one liquid are spontaneously formed in another immiscible liquid.
  • industrial scale manufacturing generally requires optimizing output while minimizing energy input. For example, when manufacturing cannabis- infused beverages in an industrial scale, the beverage manufacturer will look to process large quantities of beverage base with the emulsified cannabinoid, for example with the use of a large capacity industrial shear device (e.g., GEA Ariete homogenizer 5400 - capable of 80.000 l/h at 120 bar). From that perspective, it will be understood that reducing the processing time and energy required to achieve the desired emulsion properties, such as stability or particle size, can have significant impact on the manufacturing economics.
  • the nanoemulsion particle size or PSD generated with the herein described emulsification system is stable over an extended period of time (e.g., up to 6 weeks) while the nanoemulsion particle size or PSD generated with the comparative emulsification system is significantly unstable, showing undesirable degradation of the particle size or PSD in as little as 1 week.
  • the natural surfactant described herein has an acid backbone which confers a strong negative surface charge to the nanoemulsion generated with the emulsification system. This strong negative surface charge has at least a two-fold technical advantage. For example, this increases repulsion between the particles, which gives an inherent stability to coalescence.
  • the nanoemulsion can have an acidic pH, which is in line with current regulatory guidelines on cannabis beverages, without requiring addition of acidic excipients thus reducing overall production costs.
  • the nanoemulsion can have a pH ⁇ about 6, such as a pH of about 6.0, about 5.5, about 5.0, about 4.5, about 4.3, about 4.0.
  • the cannabinoid emulsification system comprises a cannabinoid component that includes a cannabinoid.
  • the cannabinoid emulsification system includes an amount of the cannabinoid component of about 1 wt.% or more, where the percentage is expressed relative to a total weight of the emulsification system.
  • the emulsification system includes an amount of the cannabinoid component of from about 1 wt.% to about 25 wt.%, including any amount therebetween or any ranges therein, such as from about 1 wt.% to about 15 wt.%.
  • the emulsification system includes an amount of the cannabinoid component of about 2 wt.%, about 5 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, or about 25 wt.%.
  • the emulsification system includes an amount of the cannabinoid component of about 5 wt.%.
  • cannabinoid is generally understood to include any chemical compound that acts upon a cannabinoid receptor.
  • Cannabinoids are commonly used for recreational purposes to produce physiological effects associated with a feeling of physical and/or emotional satisfaction.
  • Cannabinoids can also be useful in the treatment and/or prophylaxis of a wide variety of diseases or conditions, such as pain, anxiety, inflammation, autoimmune diseases, neurological disorder, psychiatric disorder, malignancy, metabolic disorder, nutritional deficiency, infectious disease, gastrointestinal disorder, or cardiovascular disorder.
  • Cannabinoids may also have application as neuroprotectants, for example, in limiting neurological damage following ischemic insults, such as stroke and trauma, or in the treatment of neurodegenerative diseases such as Alzheimer’s disease, Parkinson’s disease and HIV dementia.
  • Cannabinoids may be extracted from any cannabis or hemp plant material (e.g., flowers, seeds, trichomes, and kief) or may be manufactured (for example cannabinoids produced in yeast, for example as described in WO WO2018/148848).
  • the term “cannabis plant(s)” encompasses wild type Cannabis (including but not limited to the species Cannabis sativa, Cannabis indica and Cannabis ruderalis) and also variants thereof, including cannabis chemovars (or “strains”) that naturally contain different amounts of the individual cannabinoids.
  • the cannabinoid is obtained from a “natural” source, i.e. , it is not manufactured.
  • the cannabinoid is obtained from a cannabis extract (e.g., resin, wax, concentrate, distillate, or isolate).
  • a cannabis extract e.g., resin, wax, concentrate, distillate, or isolate.
  • a “cannabis extract” refers to an extract obtained from a cannabis plant material according to any procedure known in the art; such extracts yield cannabinoids in pure or isolated form.
  • a cannabis extract may be obtained by a process including an extraction step from plant materials using for example organic solvent extraction, such as extraction with CO2, butane, ethanol, and the like.
  • a cannabis extract may be obtained by a process including an extraction step from plant materials using for example heat decarboxylation to convert cannabinoids in their acid forms to neutral forms followed by or after CO2 extraction (under sub-critical or super-critical conditions), providing a crude extract.
  • the crude extract may then be “winterized,” that is, extracted with ethanol to remove lipids and waxes, as described for example in US 7,700,368, US 2004/0049059, and US 2008/0167483, which are incorporated herein by reference.
  • the method for obtaining the cannabis extract may further include purification steps such as a distillation step to further purify, isolate, or crystallize one or more cannabinoids, which is referred to herein as a “distillate”; US20160346339, which is incorporated herein by reference, describes a process for extracting cannabinoids from cannabis plant material using solvent extraction followed by filtration, and evaporation of the solvent in a distiller to obtain a distillate.
  • the distillate may be further cut with one or more terpenes.
  • the distillate may be further purified, for example using chromatographic and other separation methods known in the art, to obtain an “isolate.”
  • the cannabinoid may be an isolated cannabinoid, such as a cannabis extract, having >75% purity (as in the case of a crude extract), or > 80% purity (as in the case of a distillate), or >95% purity (as in the case of an isolate).
  • the cannabinoid may have a purity such as > 75%, or > 80%, or > 90%, or > 95%, or > 98%, or > 98%, or > 99%, or > 99.5%.
  • cannabinoids include, but are not limited to, cannabichromanon (CBCN), cannabichromene (CBC), cannabichromevarin (CBCV), cannabicitran (CBT), cannabicyclol (CBL), cannabicyclovarin (CBLV), cannabidiol (CBD), cannabidiolic acid (CBDA), cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD-C4), cannabidiorcol (CBD-C1), cannabidiphorol (CBDP), cannabidivarin (CBDV), cannabielsoin (CBE), cannabifuran (CBF), cannabigerol (CBG), cannabigerol monomethylether (CBGM), cannabigerolic acid (CBGA), cannabigerovarin (CBGV), cannabinodiol (CBND), cann
  • Examples of synthetic cannabinoids include, but are not limited to, naphthoylindoles, naphthylmethylindoles, naphthoylpyrroles, naphthylmethylindenes, phenylacetylindoles, cyclohexylphenols, tetramethylcyclopropylindoles, adamantoylindoles, indazole carboxamides, quinolinyl esters, and combinations thereof.
  • Cannabidiol means one or more of the following compounds: A 5 -cannabidiol (2- (6-isopropenyl-3-methyl-5-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A 4 -cannabidiol (2-(6- isopropenyl-3-methyl-4-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A 3 -cannabidiol (2-(6- isopropenyl-3-methyl-3-cyclohexen-l-yl)-5-pentyl-l,3-benzenediol); A 3J -cannabidiol (2-(6- isopropenyl-3-methylenecyclohex-l-yl)-5-pentyl-l,3-benzenediol); A 2 -cannabidiol (2-(6- isopropenyl-3-methylenecyclohex-
  • Tetrahydrocannabinol means one or more of the following compounds: A8- tetrahydrocannabinol (A8-THC), A9-cis-tetrahydrocannabinol (cis-THC), and A9- tetrahydrocannabinol (A9-THC).
  • THC means one or more of the following compounds: A9-tetrahydrocannabinol and A8- tetrahydrocannabinol.
  • the cannabinoid may be in an acid form or a non-acid form, the latter also being referred to as the decarboxylated form since the non-acid form can be generated by decarboxylating the acid form.
  • the cannabinoid can be in its acid or non-acid form or be a mixture of both acid and non-acid forms.
  • the cannabinoid component may include a single cannabinoid or may include a combination of two or more cannabinoids.
  • the cannabinoid component includes CBD, THC, or a mixture thereof.
  • cannabinoids can be used in combination to achieve a desired effect in a user.
  • Suitable mixtures of cannabinoids that can be used in the present disclosure include but are not limited to a mixture of THC, and CBD.
  • Certain specific ratios of cannabinoids may be useful to produce the feeling of physical and/or emotional satisfaction and/or may be useful in the treatment or management of specific diseases or conditions.
  • the cannabinoid component includes a mixture of THC and CBD.
  • the w/w ratio of the THC to the CBD in the cannabinoid emulsification system may be between about 1:1000 and about 1000:1.
  • the w/w ratio of THC to CBD in the composition may be about 1:1000, about 1:900, about 1:800, about 1:700, about 1:600, about 1:500, about 1:400, about 1:300, about 1:250, about 1:200, about 1:150, about 1:100, about 1:90, about 1:80, about 1:70, about 1:60, about 1:50, about 1:45, about 1:40, about 1:35, about 1:30, about 1:29, about
  • the cannabinoid emulsification system includes the cannabinoid in a concentration of about 0.001 mg/mL or more.
  • the emulsification system comprises the cannabinoid in an amount of from about 0.001 mg/mL to about 100 mg/mL, including any amount therebetween or any ranges therein.
  • the emulsification system comprises the cannabinoid in an amount of from about 1 mg/mL to about 50 mg/mL, from about 5 mg/mL to about 40 mg/mL, from about 5 mg/mL to about 30 mg/mL, including any amount therebetween or any ranges therein.
  • the cannabinoid component may comprise other ingredients, including but not limited to a carrier oil, a terpene, or any combinations thereof.
  • a carrier oil and “a terpene” include “one or more carrier oil(s)” and “one or more terpene(s)”, respectively.
  • carrier oil refers to medium chain triglycerides (MCT, comprising chains of between 6 and 12 carbon atoms), long chain triglycerides (LCT, comprising chains of between 13 to 21 carbon atoms), a combination thereof, or any other suitable carrier oil.
  • MCT medium chain triglycerides
  • LCDT long chain triglycerides
  • Non-limiting examples of such other suitable carrier oils include: borage oil, coconut oil, cottonseed oil, soybean oil, safflower oil, sunflower oil, corn oil, olive oil, palm oil, peanut oil, almond oil, sesame oil, rapeseed oil, peppermint oil, poppy seed oil, canola oil, palm kernel oil, hydrogenated soybean oil, hydrogenated vegetable oils, glyceryl esters of saturated fatty acids, glyceryl behenate, glyceryl distearate, glyceryl isostearate, glyceryl laurate, glyceryl monooleate (e.g., PeceolTM), glyceryl, monolinoleate, glyceryl palmitate, glyceryl palmitostearate, glyceryl ricinoleate, glyceryl stearate, polyglyceryl 10-oleate, polyglyceryl 3-oleate, polyglyceryl 4-oleate, polyglyceryl 10-
  • Terpene refers to refer to a class of chemical components comprised of the fundamental building block of isoprene, which can be linked to form linear structures or rings.
  • Terpenes may include hemiterpenes (single isoprenoid unit), monoterpenes (two units), sesquiterpenes (three units), diterpenes (four units), sesterterpenes (five units), triterpenes (six units), and so on. At least some terpenes are expected to interact with, and potentiate the activity of, cannabinoids.
  • terpenes known to be extractable from cannabis include aromadendrene, bergamottin, bergamotol, bisabolene, borneol, 4-3-carene, caryophyllene, cineole/eucalyptol, p-cymene, dihydroj asmone, elemene, farnesene, fenchol, geranylacetate, guaiol, humulene, isopulegol, limonene, linalool, menthone, menthol, menthofuran, myrcene, nerylacetate, neomenthylacetate, ocimene, perillylalcohol, phellandrene, pinene, pulegone, sabinene, terpinene, terpineol, 4-terpineol, terpinolene, and derivatives thereof.
  • terpenes include nerolidol, phytol, geraniol, alpha-bisabolol, thymol, genipin, astragaloside, asiaticoside, camphene, beta-amyrin, thujone, citronellol, 1 ,8-cineole, cycloartenol, and derivatives thereof.
  • the cannabinoid component may include other ingredients in addition to the above described additional ingredients.
  • the carrier oil is present in the cannabinoid component such that there is a ratio of the amount of the carrier oil to an amount of the cannabinoid of from about 1.6:1 to about 1 :0 (where “0” refers to an amount close to but not equal to 0).
  • the ratio of the amount of the carrier oil to the amount of the cannabinoid can be of about 0.75:0.7, about 0.75:0.6, about 0.75:0.5, about 0.75:0.4, about 0.75:0.3; about 0.75:0.2, about 0.75:0.1 , about 0.75:0, about 0.8:0.8, about 0.8:0.7, about 0.8:0.6, about 0.8:0.5, about 0.8:0.4, about 0.8:0.3; about 0.8:0.2, about 0.8:0.1 , about 0.8:0, about 0.9:0.8, about 0.9:0.7, about 0.9:0.6, about 0.9:0.5, about 0.9:0.4, about 0.9:0.3; about 0.9:0.2, about 0.9:0.1 , about 0.9:0, about 1 :0.9, about 1 :0.8, about 1 :0.7, about 1 :0.6, about 1 :0.5, about 1 :0.4, about 1 :0.3, about 1 :0.2, about 1 :0.1 , about 1 :0, about 1 :0.9, about 1 :0.8,
  • the cannabis-infused product is a solid or semi-solid edible product.
  • Edible products come in many forms and can be any product that is suitable, e.g., nontoxic, for placing into the mouth of a human or animal, whether ingested, absorbed, or only chewed or sucked on and at least a portion discarded, etc.
  • a common feature of the solid or semisolid edible product is that it includes an aqueous component that benefits from the herein described cannabinoid emulsification system properties.
  • Illustrative examples of human edible products include but are not limited to confections such as chewing or bubble gums, mints, suckers, jawbreakers, lozenges, hard candies, gummy candies, taffies, and chocolates; baked goods such as muffins, brownies, cookies, crackers, and granola bars, and meal replacement bars; and dissolving strips.
  • a chewing-gum may have a hard shell (akin an ExcelTM chewing-gum) or not (akin Juicy FruitTM).
  • the cannabis-infused product is a liquid cannabis-infused product.
  • cannabis-infused beverages for example, cannabis-infused beverages, drops, tinctures or sprays.
  • cannabis-infused products may include gels, creams, custard, pudding, honey, syrup, broth, soup, gelatin, yogurt, puree, jelly, sauce, liquid eggs, or salad dressing.
  • cannabis-infused beverages can include, but without being limited to, drinking water, milk (both diary and non-diary), juice, a smoothie, coffee or a caffeinated beverage, tea, herbal tea, a cocoa beverage, an energy drink, a drinkable yogurt, a fermented beverage, or an alcoholic or non-alcoholic drink.
  • An alcoholic or non-alcoholic drink includes but is not limited to, lager, cider, spirits, wine/fortified wine, and cocktails.
  • the cannabis-infused beverages can be sparkling (e.g., carbonated, nitrogenated, etc.) or not.
  • the beverage base may include water, juice, dairy base, non-alcoholic beverage, vitamin water, iced tea or any other suitable base.
  • the beverage base may include carbonated water.
  • the beverage base may contain other ingredients such as, but not limited to, preservatives, flavorings, sweeteners, stabilizers, dyes, or carbonation.
  • the beverage base is a cannabinoid-less beverage.
  • the beverage base includes one or more of the following properties: a pH of between about 3 and about 7; a salt/mineral content (based on common electrolyte drinks, mg/250ml) of one or more of the following: 0-150 mg sodium, 0-150 mg potassium, 0-75 mg magnesium, and 0-75 mg calcium; a tannin content (in the case of tea) of between about 1300 pg/ml and about 3000 pg/ml, such as 2700 pg/ml (Green Tea), 1600 pg/ml (White Tea), 1800 pg/ml (Oolong Tea), 2465 pg/ml (Black tea); a protein content of less than about 30 g / serving, such as from about 25 to about 30 g / serving.
  • a pH of between about 3 and about 7 a salt/mineral content (based on common electrolyte drinks, mg/250ml) of one or more of the following: 0-150 mg sodium, 0-150 mg potassium, 0-75 mg magnesium, and
  • the emulsification system manufacturer can infuse the base product to obtain the cannabis-infused product, ready for packaging and commercialization.
  • the cannabinoid emulsification system may be packaged and sold to a product manufacturer, which can then use same to infuse the base product to obtain the cannabis-infused product.
  • the cannabinoid emulsification system may be packaged and commercialized alone or together with a base product such that the end-user may use same to infuse the base product and obtain the cannabis-infused product.
  • the base product may be infused with the emulsification system in the form of the desired nanoemulsion.
  • the base product may be infused with the emulsification system in the form of an emulsion, and then the infused based product (thus containing the emulsification system) may be processed with techniques known on the art (e.g., high shear) to generate the desired nanoemulsion.
  • techniques known on the art e.g., high shear
  • a cannabis-infused chewing gum in order to obtain a cannabis-infused chewing gum, one may proceed to contact and mix the chewing gum ingredients comprising an aqueous component (such as gum base [e.g., elastomers, waxes, and resin], sweeteners, glycerin, plasticizer and colors) with the herein described cannabinoid emulsification system and process the resulting mixture to obtain the cannabis-infused chewing gum containing a nanoemulsion having a particle size of about 135 nm or less.
  • an aqueous component such as gum base [e.g., elastomers, waxes, and resin], sweeteners, glycerin, plasticizer and colors
  • the cannabinoid emulsification system manufacturer may proceed to incorporate same into a beverage base and process the resulting mixture to obtain the cannabis-infused beverage containing a nanoemulsion having a particle size of about 135 nm or less.
  • the cannabinoid emulsification system may be packaged and sold to a beverage manufacturer, which can then proceed to incorporate same into a beverage base and process the resulting mixture to obtain the cannabis-infused product containing a nanoemulsion having a particle size of about 135 nm or less.
  • the cannabinoid emulsification system may be packaged and commercialized alone or together with a base product such that the end-user may use same to obtain the cannabis-infused product.
  • the end user may dispense the cannabinoid emulsification system from a pouch containing same into a bottled beverage.
  • the cannabis-infused product may comprise at least 0.002 mg/ml (or mg/g) of cannabinoid(s).
  • the cannabis-infused product may include from 0.002 mg/ml (or mg/g) to about 1 mg/ml (or mg/g) of cannabinoid(s).
  • the cannabis-infused product is a unit, the unit comprising less than 1000 mg, or less than 900 mg, or less than 800 mg, or less than 700 mg, or less than 600 mg, or less than 500 mg, or less than 400 mg, or less than 300 mg, or less than 200 mg, or less than 100 mg, or less than 50 mg, or less than 40 mg, or less than 30 mg, or less than 20 mg, or less than 10 mg, or less than 5 mg, or less than 2.5 mg of cannabinoid(s).
  • the unit may include from any amount of cannabinoid selected from the range of from about 1 mg to about 1000 mg.
  • the nanoemulsion generated from the cannabinoid emulsification system of the present disclosure exhibits a shelf-life stability for at least one week, at least 2 weeks, at least 3 weeks, at least 1 month, at least 1.5 months, at least 2 months, at least 4 months, at least 6 months, and in some cases even more under ambient storage conditions (at about room temperature, i.e., about 20°C.)
  • shelf-life stability may be determined in several ways. For example, shelf-life stability of the nanoemulsion generated from the cannabinoid emulsification system may be determined with qualitative methods (e.g., presence or absence of ringing, phase separation, creaming, precipitation, etc.) or quantitative methods (e.g., PSD, %PD, turbidity, cannabinoid concentration, etc.). For example, shelf-life stability may reflect important consumer acceptability parameters, which include clear physical appearance (for clear beverages), no discoloration (for opaque beverages) and/or no adverse visual effects (e.g., ringing, creaming, etc.) across the beverage as it is consumed.
  • qualitative methods e.g., presence or absence of ringing, phase separation, creaming, precipitation, etc.
  • quantitative methods e.g., PSD, %PD, turbidity, cannabinoid concentration, etc.
  • shelf-life stability may reflect important consumer acceptability parameters, which include clear physical appearance (for clear beverages), no discoloration (for
  • cannabinoids in aqueous solution can cause precipitation, ringing and/or creaming effects. This issue may also be magnified when the beverage product comprises elevated amounts of the cannabinoid(s). As a result, consumers typically will not want to consume beverage products that precipitate or become cloudy when stored or kept available for extended periods. Surprisingly, the inventors have found that a beverage product that appears clear and/or without any visual defects over extended periods is obtainable when using the cannabinoid emulsification system described herein.
  • Cannabis-infused products are typically used for recreational and/or medicinal uses.
  • cannabis-infused products can be used to achieve a desired effect in a user, such as a psychoactive effect, a physiological effect, or a treatment of a condition.
  • a psychoactive effect it is meant a substantial effect on mood, perception, consciousness, cognition, or behavior of a subject resulting from changes in the normal functioning of the nervous system.
  • physiological effect it is meant an effect associated with a feeling of physical and/or emotional satisfaction.
  • treatment of a condition it is meant the treatment or alleviation of a disease or condition by absorption of cannabinoid(s) at sufficient amounts to mediate the therapeutic effects.
  • treating is used herein to mean obtaining a desired pharmacologic and/or physiologic effect.
  • the effect may be prophylactic, in terms of completely or partially preventing a disease, condition, or symptoms thereof, and/or may be therapeutic in terms of a partial or complete cure for a disease or condition and/or adverse effect, such as a symptom, attributable to the disease or disorder.
  • Treatment covers any treatment of a disease or condition of a mammal, such as a dog, cat or human, preferably a human.
  • the disease or condition is selected from the group consisting of pain, anxiety, an inflammatory disorder, a neurological disorder, a psychiatric disorder, a malignancy, an immune disorder, a metabolic disorder, a nutritional deficiency, an infectious disease, a gastrointestinal disorder, and a cardiovascular disorder.
  • the disease or condition is pain.
  • the disease or condition is associated with the feeling of physical and/or emotional satisfaction.
  • the “effective amount” administered and rate and timecourse of administration will depend on the desired effect associated with a feeling of physical and/or emotional satisfaction in the subject.
  • the “effective amount” administered and rate and time-course of administration will depend on the nature and severity of the disease or condition being treated and typically also takes into consideration the condition of the individual subject, the method of administration and the like. Manufacturing Processes
  • the cannabinoid emulsification system of the present disclosure can be made via a number of different processes.
  • the cannabinoid emulsification system of the present disclosure can be made with a method comprising the steps of: a) preparing an oil phase comprising the cannabinoid component; b) preparing an aqueous phase comprising water; c) incorporating ethanol as the co-emulsifier either in the oil phase or in the aqueous phase; d) incorporating the natural emulsifier either in the oil phase or in the aqueous phase; and e) dispersing the oil phase in the aqueous phase to form an emulsion.
  • optional ingredients may be included in one or more of steps a) to e), and may include natural preservatives, such as rosemary or oregano extract, sugar, salt, lemon juice, grapefruit seed extract, citric acid (from citrus fruits), aloe vera, benzyl alcohol (e.g., extracted from plants or anal glands of beavers), potassium sorbate, sorbic acid, and the like.
  • natural preservatives such as rosemary or oregano extract, sugar, salt, lemon juice, grapefruit seed extract, citric acid (from citrus fruits), aloe vera, benzyl alcohol (e.g., extracted from plants or anal glands of beavers), potassium sorbate, sorbic acid, and the like.
  • ethanol as the co-emulsifier is incorporated in the oil phase at step c) above.
  • the process further comprises: f) forming a nanoemulsion, for example by processing the emulsion of step e) (or a base product containing such emulsion) with a high shear step, e.g., by sonicating, high pressure homogenizing, valve homogenization, or a combination thereof.
  • a high shear step e.g., by sonicating, high pressure homogenizing, valve homogenization, or a combination thereof.
  • the following assays can be used to quantitatively assess the properties of the emulsification system and/or the nanoemulsion generated therefrom.
  • the particle sizes of the cannabinoid nanoemulsions were measured in a water solution at 25°C using the Dynamic Light Scattering (DLS) method. All samples are analyzed at a dilution of 1/20 in purified water and measurements require 1-2 mL of sample in order to accurately generate a signal.
  • the LiteSizerTM (Anton Paar) particle size analyser was used for all particle size measurements.
  • Cannabinoid emulsification system was formulated to a concentration of 25 mg/mL THC (i.e. , “concentrate”) and then diluted to a concentration of 0.03 mg/mL THC (also referred to as “diluted”) in a beverage base.
  • a sample of 10 mL from each beverage was prepared in glass containers and/or (beer) cans and incubated either at 25°C (i.e., to mimic long term storage condition) and 40°C (i.e., to mimic accelerated storage condition) for extended periods.
  • the PSD, %PD, the cannabinoid concentration, and the visual appearance were recorded at set intervals of time, e.g., zero, 2 weeks, 4 weeks, 6 weeks, 8 weeks, 12 weeks, etc.
  • Example 1 Cannabinoid emulsification systems
  • cannabinoid emulsification systems in accordance with the present disclosure and comparative cannabinoid emulsification systems were prepared. Ingredients of these cannabinoid emulsification systems are provided below in Table 1.
  • aqueous ingredients i.e., water and Q-Naturale
  • oil phase ingredients i.e., ethanol, MCT and THC
  • the oil phase was then added to the aqueous phase while mixing with a medium shear between about 4000 rpm and about 8000 rpm for about 5 minutes to produce a mixture. •
  • the resultant mixture was then subjected to high shear homogenization with a GEA valve homogenizer at a shear between about 1400 Bar and about 1600 Bar for 3 passes to generate nanoemulsions.
  • Ethanol as co-emulsifier was added in the aqueous phase for test 4, whereas it was added in the oil phase for test 5.
  • Table 1 the combination of the natural saponin extract emulsifier Q-Naturale solution with ethanol as co-emulsifier leads to a nanoemulsion having a particle size lower than about 135 nm.
  • Test 1 the comparative emulsification system
  • the same experimentation was performed with the formulations of Tests 3-5, and the particle size was assessed after each pass on the GEA homogenizer. The results are shown in Table 2.
  • the cannabinoid emulsification system from Example 1 was used to infuse beverage bases and obtain cannabis-infused beverage products.
  • the stability of the nanoemulsion in the cannabis-infused beverage products was then tested as a function of its particle size and THC content. The results are set forth in Tables 3 to 5 below.
  • Tables 3 and 4 show that cannabis-infused beverage products containing an embodiment of the cannabinoid emulsification system of the present disclosure are stable after 4 weeks at both 25°C and 40°C when stored in a glass container.
  • Table 5 shows that cannabis- infused beverage products containing such embodiment of the cannabinoid emulsification system of the present disclosure are also stable after 4 weeks at both 25°C and 40°C when stored in a beer can.
  • test conditions were normal storage conditions (at room temperature - “RT”, i.e., about 25 °C) or accelerated storage conditions (about 40 °C). Typically, 1 month at 40 °C is equivalent to 3 months at 25 °C.
  • Rows A and B represent the results from the cannabinoid emulsification system of test 2 from Example 1 albeit with a concentration of THC of about 25 mg/mL.
  • the concentrated cannabinoid emulsification system was then diluted to a concentration of cannabinoid of about 0.03 mg/mL (rows C and D) and the resulting diluted cannabinoid emulsification system was then completed by various compounds typically found in beverage bases / beverage products (rows E to X).
  • Table 6 Qualitative assessment
  • the cannabinoid emulsification system in accordance with an embodiment of the present disclosure tested alone (concentrated or diluted form) or in combination with compounds typically found in beverage bases I beverage products, maintains stable quantitative and qualitative properties over a period of up to 6 weeks.
  • the stability of a cannabinoid emulsification system was tested according to Test Method 2.
  • the cannabinoid emulsification system tested here has similar formulation as that one used for the stability test of Example 3, except that the natural antioxidant TocobiolTM was added to the oil phase and that the synthetic chelating agent EDTA was added to the concentrated emulsion after the GEA homogenizing process.
  • the cannabinoid emulsification system in accordance with an embodiment of the present disclosure infused into a number of beverage bases to obtain cannabis-infused beverages maintains stable quantitative and qualitative properties over a period of at least 4 weeks.
  • these tables show that including Tocobiol and EDTA does not negatively impact the properties of the nanoemulsion generated with the cannabinoid emulsification system.
  • this example made use of the synthetic chelating agent EDTA, the reader will readily understand that EDTA is only a non-limiting illustrative compound and that any natural antioxidant or chelating agent is preferably used instead.
  • the terms “around”, “about” or “approximately” shall generally mean within the error margin generally accepted in the art.
  • this term may refer to a measurable value such as an amount, a temporal duration, and the like, and is meant to encompass variations of less than +/- 10% of the given value, such as variations of about +/- 5%, about +/- 2%, about +/- 1%, about +/- 0.5%, or about +/- 0.1 %.
  • the terms “preferred”, “preferably” and variants refer to embodiments of the disclosure that afford certain benefits, under certain circumstances. However, other embodiments may also be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful and is not intended to exclude other embodiments from the scope of the disclosure.

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Abstract

La présente divulgation concerne un système d'émulsification de cannabinoïde pour la fabrication de produits à base de cannabis infusé, en particulier des produits à base de cannabis infusé qui comprennent un constituant aqueux. Le système d'émulsification de cannabinoïde comprend un constituant cannabinoïde qui comprend un cannabinoïde. Le système d'émulsification de cannabinoïde comprend également un extrait de saponine en tant qu'émulsifiant et de l'éthanol en tant que co-émulsifiant. Le système d'émulsification de cannabinoïde génère avantageusement des particules d'émulsion stables dans les plages nanométriques tout en incluant des ingrédients émulsifiants naturels, et est particulièrement utile pour la fabrication industrielle à grande échelle de produits à base de cannabis infusé, la génération de la nano-émulsion étant de préférence réalisée par homogénéisation.
PCT/CA2022/050097 2021-01-25 2022-01-24 Systèmes d'émulsification de cannabinoïde contenant des ingrédients naturels pour la fabrication de produits à base de cannabis infusé Ceased WO2022155757A1 (fr)

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Citations (1)

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US20160089320A1 (en) * 2014-09-29 2016-03-31 Barrie Tan Non-Synthetic Emulsion-Based Lipid Formulations and Methods of Use

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