CROSS-REFERENCE TO RELATED APPLICATION

[0001] The present application claims the benefit of U.S. provisional patent application serial number 63/141 ,297 filed on January 25, 2021. The contents of the above-referenced document are incorporated herein by reference in their entirety.

TECHNICAL FIELD

[0002] 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.

BACKGROUND

[0003] Implementing manufacturing processes for manufacturing cannabis-infused products at an industrial scale, particularly cannabis-infused products that include an aqueous component has faced several challenges. Indeed, in order to meet the expected user experience demands from consumers, the cannabis-infused products must have predictable and controlled properties, such as cannabinoid content, stability (e.g., throughout the supply chain, including storage and shipping), physical appearance (clarity, lack of ringing I creaming, etc.), fast onset, and pleasant organoleptic properties, which are difficult to obtain with cannabis extracts as these are lipophilic.

[0004] It has been proposed to use 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, however, 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. Further, 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.

[0005] While natural emulsifiers have been proposed for use in emulsification systems, their use remains difficult to implement at an industrial scale. Indeed, the heterogeneity in the chemical structure of various natural emulsifiers (e.g., natural emulsifiers may vary in content throughout the year) makes it difficult to predict and control the properties of the cannabis-infused products discussed above, for example obtaining stable smaller particle size distributions to achieve the desired fast onset.

[0006] Thus, there remains a need for improved cannabinoid emulsification systems for industrial scale production of cannabis-infused products, particularly cannabis-infused products that include an aqueous component.

SUMMARY

[0007] This Summary is provided to introduce a selection of concepts in a simplified form that are further described below in the Detailed Description. This Summary is not intended to identify key aspects or essential aspects of the claimed subject matter.

[0008] 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.

[0009] In accordance with a broad aspect, 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.

[0010] In some implementations, 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.

• the saponin extract is Q-Naturale.

• 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).

• 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.

[0011] In accordance with a broad aspect, 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.

[0012] In some implementations, the method of manufacturing the cannabinoid emulsification system may have one or more of the following features:

• the ethanol as the co-emulsifier is incorporated in the aqueous phase.

• the ethanol as the co-emulsifier is incorporated in the oil phase.

• the saponin extract as the emulsifier is incorporated in the aqueous phase.

• 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.

• the saponin extract is Q-Naturale.

• 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).

• the nanoemulsion has a pH of about 7 or less.

• the cannabinoid emulsification system consists essentially of natural ingredients.

[0013] In accordance with a broad aspect, 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.

[0014] In accordance with a broad aspect, the present disclosure relates to a cannabis-infused product that comprises the cannabinoid emulsification system described herein.

[0015] In some implementations, 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.

[0016] All features of exemplary embodiments which are described in this disclosure and are not mutually exclusive can be combined with one another. Elements of one embodiment can be utilized in the other embodiments without further mention. Other aspects and features of the present invention will become apparent to those ordinarily skilled in the art upon review of the following description of specific embodiments.

DETAILED DESCRIPTION

[0017] A detailed description of one or more embodiments is provided below. The invention is described in connection with such embodiments, but the invention is not limited to any embodiment. The scope of the invention is limited only by the claims. Numerous specific details are set forth in the following description in order to provide a thorough understanding of the invention. These details are provided for the purpose of non-limiting examples and the invention may be practiced according to the claims without some or all these specific details. Technical material that is known in the technical fields related to the invention has not been described in detail so that the disclosure is not unnecessarily obscured.

Cannabinoid emulsification system

[0018] 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. [0019] Without being bound by any theory, it is believed that combining a saponin extract as emulsifier and ethanol as co-emulsifier as described herein offers several technical advantages. For example, despite the above-discussed heterogeneity in chemical structure of natural emulsifiers, the herein described cannabinoid emulsification system reproducibly generates a stable emulsion with particle sizes in the nanoscale range. Moreover, 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.

[0020] As used herein, the term “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.

[0021] The herein described cannabinoid emulsification system generates a stable nanoemulsion with a particle size of about 135 nm or less. For example, 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. As used herein, 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.

[0022] “Particle size distribution” or “PSD” is an index (means of expression) indicating what sizes (particle size) of particles are present in what proportions (relative particle amount as a percentage where the total amount of particles is 100 %) in the sample particle group to be measured. Volume, area, length, and quantity are used as standards (dimensions) for particle amount. However, generally, 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. [0023] In the present disclosure, the polydispersity index (PDI) (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 % polydispersity (%PD) can be obtained with the following calculation %PD = PDI ^1/2 x 100. The calculations for these parameters are defined in the ISO standard document 13321 :1996 E and ISO 22412:2008.

[0024] In some embodiments, the cannabinoid emulsification system generates an emulsion having a %PD of about 20% or less. For example, 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%. For example, a %PD of about 6%, about 8%, about 10%, about 12%, about 14%, about 16%, about 18, or about 20%, including any amount therebetween.

[0025] The emulsification system described herein can be used to infuse a base product to obtain the cannabis-infused product. For example, the emulsification system manufacturer can infuse the base product to obtain the cannabis-infused product, ready for packaging and commercialization. In some embodiments, 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. In some embodiments, 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.

[0026] As used herein, 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. For example, 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.

[0027] As used herein, the term “cannabis-infused product” refers to commercial solid, semisolid, or liquid products containing a cannabinoid. For example, 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.

[0028] Each component of the cannabinoid emulsification system will now be further described.

Saponin extract as emulsifier

[0029] The cannabinoid emulsification system comprises a saponin extract as emulsifier.

[0030] 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.

[0031] In some embodiments, the saponin extract is a food grade saponin extract.

[0032] In some embodiments, the saponin extract is a plant material saponin extract. For example, 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. For example, 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).

[0033] In some embodiments, the saponin extract is obtained by cell culture of Quillaia species, such as Quillaja saponaria, Quillaja smegmadermos or Quillaja brasilensis.

[0034] In some embodiments, 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. For example, 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. For example, 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. [0035] In some embodiments, the saponin extract is in the form of a saponin extract aqueous solution. For example, the saponin extract aqueous solution may include the saponin extract and water. Optionally, the saponin extract aqueous solution may further include preservatives. The reader will readily understand that 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. For example, when using 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.

[0036] In some embodiments, 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. For example, the saponin extract aqueous solution may include saponins in an amount of from about 13 wt.% to about 16 wt.% (wet basis).

[0037] In some embodiments, 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. For example, 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 10.4:1, about 10.3:1, about 10.2:1, about 10.1:1, about 10:1, about 9.9:1, about 9.8:1, about 9.7:1, about 9.6:1, about 9.5:1, about 9.4:1, about 9.3:1, about 9.2:1, about 9.1:1, about 9:1, about 8.9:1, about 8.8:1, about 8.7:1, about 8.6:1, about 8.5:1, about 8.4: 1 , about 8.3:1, about 8.2: 1 , about 8.1:1, about 8: 1 , about 7.9:1, about 7.8: 1 , about 7.7:1, about 7.6:1, about 7.5:1, about 7.4:1, about 7.3:1, about 7.2:1, about 7.1:1, about 7:1, about6.9:1, about6.8:1, about6.7:1, about 6.6:1, about6.5:1, about6.4:1, about6.3:1, about 6.2:1, about 6.1:1, about 6: 1 , about 5.9:1, about 5.8:1, about 5.7:1, about 5.6: 1 , about 5.5:1, about 5.4: 1 , about 5.3:1, about 5.2: 1 , about 5.1:1, about 5: 1 , about 4.9:1, about 4.8:1, about 4.7:1, about 4.6:1, about 4.5:1, about4.4:1, about 4.3:1, about 4.2:1, about 4.1:1, about4:1, about3.9:1, about 3.8:1 , about 3.7:1 , about 3.6:1 , about 3.5:1 , about 3.4:1 , about 3.3:1 , about 3.2:1 , about 3.1 :1 , about 3:1 , about 2.9:1 , about 2.8:1 , about 2.7:1 , about 2.6:1 , about 2.5:1 , about 2.4:1 , about 2.3:1 , about 2.2:1 , about 2.1 :1 , about 2:1 , about 1.9:1 , about 1.8:1 , about 1.7:1 , about 1.6:1 , about 1.5:1 , about 1.4:1 , about 1.3:1 , about 1 .25: 1 , including any amount therebetween or any ranges therein. Preferably, the ratio of the amount of the saponin extract aqueous solution to the amount of the cannabinoid component is of 1.25:1.

[0038] Saponin extracts are classified as Type 1 and Type 2, which differ in terms of purification steps. For example, 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). Regarding the structural elucidation and classification of Quillaja saponin extracts, reference can be made to the Thesis of Johan Bankefors, 2006, Uppsala, Sweden, ISBN 91-576- 7181-8.

[0039] In some embodiments, the saponin extract includes saponins in an amount of about 20 wt.% or more (dry basis). For example, 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). For example, 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).

[0040] In some embodiments, the cannabinoid emulsification system includes a Type 2 saponin extract.

[0041] In some embodiments, 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).

[0042] The reader will readily understand that in some embodiments, 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. For example, one or more emulsifier such as lecithin, whey, caseinate, and the like.

Co-emulsifier

[0043] The cannabinoid emulsification system comprises ethanol as co-emulsifier.

[0044] In some embodiments, 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. For example, 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.%. For example, 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.%. Preferably, the cannabinoid emulsification system includes ethanol as co- emulsifier in an amount of from about 10 wt.% to about 15 wt.%.

Emulsification energy

[0045] 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). Preferably, upon homogenization, the emulsification system described herein generates the herein described nanoemulsion. The reader will readily understand that such 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. [0046] The reader will readily appreciate that 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.

[0047] Without being bound by any theory, it is believed that the combination of a natural emulsifier and ethanol as co-emulsifier described herein facilitates industrial scale use of the cannabinoid emulsification system containing same, as this system affords using significantly less emulsification energy and processing time than with other comparable emulsification systems that do not have such combination of a natural emulsifier and ethanol as co-emulsifier. For example, it has been observed that using the herein described emulsification system, one can obtain the desired particle size or PSD having nanoscale sizes in 2-3 passes in a large capacity industrial homogenizer, while 15-20 passes are typically otherwise required with a comparative emulsification system that includes a natural emulsifier but does not include ethanol as co- emulsifier in order to obtain similar particle size or PSD. The reader will readily understand that in the context of an industrial homogenizer, such as a GEA homogenizer, the number of passes corresponds to the number of times an input volume has been processed through the GEA homogenizer. To clarify, processing 1 L of crude emulsion in the GEA homogenizer results in 1 L of processed emulsion, which consists of 1 pass. Processing the 1 L of processed emulsion again through the GEA homogenizer results in 1 L of processed emulsion that has undergone two passes.

[0048] Again, without being bound by any theory, it has been observed that 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. Furthermore, it has been observed that 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. For example, this also causes the nanoemulsion to 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. For example, 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.

[0049] Such technical effects observed with the herein described cannabinoid emulsification system offers significant benefits from an industrial scale perspective, as it reduces overall cost, increases yield, and simplifies the manufacturing process.

Cannabinoid component

[0050] The cannabinoid emulsification system comprises a cannabinoid component that includes a cannabinoid.

[0051] In some embodiments, 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. For example, 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.%. For example, 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.%. Preferably, the emulsification system includes an amount of the cannabinoid component of about 5 wt.%.

[0052] As used herein, the term “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.

[0053] 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. Preferably, the cannabinoid is obtained from a “natural” source, i.e. , it is not manufactured.

[0054] In some embodiments, the cannabinoid is obtained from a cannabis extract (e.g., resin, wax, concentrate, distillate, or isolate).

[0055] As used herein, 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. For example, 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. For example, 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. Optionally, 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.”

[0056] 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). For example, and without wishing to be limiting, the cannabinoid may have a purity such as > 75%, or > 80%, or > 90%, or > 95%, or > 98%, or > 98%, or > 99%, or > 99.5%. [0057] Examples of 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), cannabinodivarin (CBVD), cannabinol (CBN), cannabinol methylether (CBNM), cannabinol propyl variant (CBNV), cannabinol-C2 (CBN-C2), cannabinol-C4 (CBN-C4), cannabiorcol (CBN-C1), cannabiripsol (CBR), cannabitriol (CBO), cannabitriolvarin (CBTV), cannabivarin (CBV), dehydrocannabifuran (DCBF), A7-cis-iso tetrahydrocannabivarin, Tetrahydrocannabinol (THC), A9-tetrahydrocannabionolic acid B (THCA-B), A9- tetrahydrocannabiorcol (THC-C1), A9-tetrahydrocannabivarin (THCV), tetrahydrocannabivarinic acid (THCVA), ethoxy-cannabitriolvarin (CBTVE), trihydroxy- A9-tetrahydrocannabinol (triOH- THC), 10-ethoxy-9hydroxy-A6a-tetrahydrocannabinol, 8,9-dihydroxy-A6a-tetrahydrocannabinol, 10-oxo-A6a-tetrahydrocannabionol (OTHC), 3,4,5,6-tetrahydro-7-hydroxy-a-a -2-trimethyl-9-n- propyl-2, 6-methano-2H-1-benzoxocin-5-methanol (OH-iso-HHCV), A6a,10a- tetrahydrocannabinol (A6a,10a-THC), A8-tetrahydrocannabivarin (A8-THCV), A9- tetrahydrocannabiphorol (A9-THCP), A9-tetrahydrocannabutol (A9-THCB), derivatives of any thereof, and combinations thereof. Further examples of suitable cannabinoids are discussed in at least PCT Patent Application Pub. No. WO2017/190249 and U.S. Patent Application Pub. No. US2014/0271940, which are incorporated by reference in their entirety.

[0058] 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.

[0059] Cannabidiol (CBD) means one or more of the following compounds: A ⁵ -cannabidiol (2- (6-isopropenyl-3-methyl-5-cyclohexen-l-yl)-5-pentyl-l,3-benz enediol); A ⁴ -cannabidiol (2-(6- isopropenyl-3-methyl-4-cyclohexen-l-yl)-5-pentyl-l,3-benzene diol); A ³ -cannabidiol (2-(6- isopropenyl-3-methyl-3-cyclohexen-l-yl)-5-pentyl-l,3-benzene diol); A ^3J -cannabidiol (2-(6- isopropenyl-3-methylenecyclohex-l-yl)-5-pentyl-l,3-benzenedi ol); A ² -cannabidiol (2-(6- isopropenyl-3-methyl-2-cyclohexen-l-yl)-5-pentyl-l,3-benzene diol); A ¹ -cannabidiol (2-(6- isopropenyl-3-methyl-l-cyclohexen-l-yl)-5-pentyl-l,3-benzene diol); and A ⁶ -cannabidiol (2-(6- isopropenyl-3-methyl-6-cyclohexen-l-yl)-5-pentyl-l,3-benzene diol). In a preferred embodiment, and unless otherwise stated, CBD means A ² -cannabidiol.

[0060] Tetrahydrocannabinol (THC) means one or more of the following compounds: A8- tetrahydrocannabinol (A8-THC), A9-cis-tetrahydrocannabinol (cis-THC), and A9- tetrahydrocannabinol (A9-THC). In a preferred embodiment, and unless otherwise stated, THC means one or more of the following compounds: A9-tetrahydrocannabinol and A8- tetrahydrocannabinol.

[0061] 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. Within the context of the present disclosure, where reference is made to a specific cannabinoid, the cannabinoid can be in its acid or non-acid form or be a mixture of both acid and non-acid forms.

[0062] The cannabinoid component may include a single cannabinoid or may include a combination of two or more cannabinoids. In a non-limiting example, the cannabinoid component includes CBD, THC, or a mixture thereof.

[0063] As is known in the art, various 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.

[0064] In some embodiments, 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. Preferably, 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

1:28, about 1:27, about 1:26, about 1:25, about 1:24, about 1:23, about 1:22, about 1:21, about

1:20, about 1:19, about 1:18, about 1:17, about 1:16, about 1:15, about 1:14, about 1:13, about

1:12, about 1:11, about 1:10, about 1:9, about 1:8, about 1:7, about 1:6, about 1:5, about 1:4.5, about 1:4, about 1:3.5, about 1:3, about 1:2.9, about 1:2.8, about 1:2.7, about 1:2.6, about 1:2.5, about 1 :2.4, about 1 :2.3, about 1 :2.2, about 1:2.1, about 1 :2, about 1:1.9, about 1:1.8, about 1:1.7, about 1:1.6, about 1:1.5, about 1:1.4, about 1:1.3, about 1:1.2, about 1:1.1, about 1:1, about 1.1:1, about 1.2:1, about 1.3:1, about 1.4:1, about 1.5:1, about 1.6:1, about 1.7:1, about 1.8:1, about 1.9:1, about2:1, about 2.1:1, about2.2:1, about2.3:1, about2.4:1, about 2.5:1, about2.6:1, about 2.7:1, about 2.8:1, about 2.9:1, about 3:1, about 3.5:1, about 4:1, about 4.5:1, about 5:1, about 6:1, about 7:1, about 8:1, about 9:1, about 10:1, about 11:1, about 12:1, about 13:1, about 14:1, about 15:1, about 16:1, about 17:1, about 18:1, about 19:1, about 20:1, about 21:1, about 22:1, about 23:1, about 24:1, about 25:1, about 26:1, about 27:1, about 28:1, about 29:1, about 30:1, about 35:1, about 40:1, about 45:1, about 50:1, about 60:1, about 70:1, about 80:1, about 90:1, about 100: 1 , about 150: 1 , about 200: 1 , about 250: 1 , about 300: 1 , about 400: 1 , about 500: 1 , about 600: 1 , about 700: 1 , about 800: 1 , about 900: 1.

[0065] In some embodiments, the cannabinoid emulsification system includes the cannabinoid in a concentration of about 0.001 mg/mL or more. In a non-limiting example, 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. For example, 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. For example, about 5 mg/mL, about 10 mg/mL, about 15 mg/mL, about 20 mg/mL, about 25 mg/mL, and the like.

[0066] In some embodiments, the cannabinoid component may comprise other ingredients, including but not limited to a carrier oil, a terpene, or any combinations thereof. The reader will readily understand that the expressions “a carrier oil” and “a terpene” include “one or more carrier oil(s)” and “one or more terpene(s)”, respectively.

[0067] As used herein, the term “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. 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., Peceol™), glyceryl, monolinoleate, glyceryl palmitate, glyceryl palmitostearate, glyceryl ricinoleate, glyceryl stearate, polyglyceryl 10-oleate, polyglyceryl 3-oleate, polyglyceryl 4-oleate, polyglyceryl 10-tetralinoleate, behenic acid, or any combinations thereof.

[0068] As used herein, the term “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. Examples of 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. Additional examples of terpenes include nerolidol, phytol, geraniol, alpha-bisabolol, thymol, genipin, astragaloside, asiaticoside, camphene, beta-amyrin, thujone, citronellol, 1 ,8-cineole, cycloartenol, and derivatives thereof.

[0069] The reader will readily understand that in some embodiments, the cannabinoid component may include other ingredients in addition to the above described additional ingredients.

[0070] When the cannabinoid component includes carrier oil, 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). For example, 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, including any amount therebetween or any ranges therein. Preferably, the ratio of the amount of the carrier oil to the amount of the cannabinoid is of about 2:1. Cannabis-infused product

[0071] In some embodiments, 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. For example, a chewing-gum may have a hard shell (akin an Excel™ chewing-gum) or not (akin Juicy Fruit™).

[0072] In some embodiments, the cannabis-infused product is a liquid cannabis-infused product. For example, cannabis-infused beverages, drops, tinctures or sprays.

[0073] Other examples of cannabis-infused products may include gels, creams, custard, pudding, honey, syrup, broth, soup, gelatin, yogurt, puree, jelly, sauce, liquid eggs, or salad dressing.

[0074] For example, 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. For example, the beverage base may include water, juice, dairy base, non-alcoholic beverage, vitamin water, iced tea or any other suitable base. For example, in the case of flavored sodas 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. Preferably, the beverage base is a cannabinoid-less beverage. For example, 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.

[0075] The person of skill will readily understand how to infuse a base product to obtain the cannabis-infused product.

[0076] For example, the emulsification system manufacturer can infuse the base product to obtain the cannabis-infused product, ready for packaging and commercialization. In some embodiments, 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. In some embodiments, 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. In any of these embodiments, the reader will readily understand that the base product may be infused with the emulsification system in the form of the desired nanoemulsion. Alternatively, 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.

[0077] For example, 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.

[0078] For example, in order to obtain a cannabis-infused beverage, 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. Alternatively, 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. Alternatively, 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. For example, the end user may dispense the cannabinoid emulsification system from a pouch containing same into a bottled beverage.

[0079] In some embodiments, the cannabis-infused product may comprise at least 0.002 mg/ml (or mg/g) of cannabinoid(s). For example, 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).

[0080] In one embodiment, 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). For example, the unit may include from any amount of cannabinoid selected from the range of from about 1 mg to about 1000 mg.

[0081] In some embodiment, 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.)

[0082] 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. It is well known that 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.

Use of cannabis-infused products

[0083] Cannabis-infused products are typically used for recreational and/or medicinal uses. For example, 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. By “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. By “physiological effect”, it is meant an effect associated with a feeling of physical and/or emotional satisfaction. By “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.

[0084] The terms “treating”, “treatment” and the like are 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” as used herein covers any treatment of a disease or condition of a mammal, such as a dog, cat or human, preferably a human.

[0085] In certain embodiments, 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. Preferably the disease or condition is pain. In other embodiments, the disease or condition is associated with the feeling of physical and/or emotional satisfaction.

[0086] In the context of recreational use, 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.

[0087] In the context of health and wellness use, 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

[0088] The cannabinoid emulsification system of the present disclosure can be made via a number of different processes.

[0089] For example, 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.

[0090] For example, 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.

[0091] Preferably, ethanol as the co-emulsifier is incorporated in the oil phase at step c) above.

[0092] To generate the nanoemulsion, 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.

TEST METHODS

[0093] The following assays can be used to quantitatively assess the properties of the emulsification system and/or the nanoemulsion generated therefrom.

Test Method 1 : Particle size

[0094] 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 LiteSizer™ (Anton Paar) particle size analyser was used for all particle size measurements.

Test Method 2: Stability Test

[0095] The stability of the cannabinoid nanoemulsions were assessed in a cannabis-infused beverage. 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.

[0096] 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.

EXAMPLES

[0097] The following examples describe some exemplary modes of making and practicing certain compositions that are described herein. These examples are for illustrative purposes only and are not meant to limit the scope of the compositions and methods described herein.

Example 1 : Cannabinoid emulsification systems

[0098] In this example, 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.

[0099] The cannabinoid emulsification systems were prepared as follows:

• The aqueous ingredients (i.e., water and Q-Naturale) and oil phase ingredients (i.e., ethanol, MCT and THC) were solubilized separately. The oil phase was heated at 60°C and stirred with a magnetic stir bar for 30 minutes.

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.

Table 1

[0100] Ethanol as co-emulsifier was added in the aqueous phase for test 4, whereas it was added in the oil phase for test 5. As can be seen from 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. In order to test whether increasing the number of passes on the GEA homogenizer would afford obtaining a particle size lower than about 135 nm for the comparative emulsification system (i.e., Test 1), 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.

Table 2

[0101] As can be seen from Table 2, the combination of the natural saponin extract emulsifier Q-Naturale with ethanol as co-emulsifier leads to a nanoemulsion particle size lower than about 135 nm with a number of passes that are acceptable from a large scale-industrial perspective, i.e., 2-3 passes. While such particle size may be obtained with the comparative test 1 at 5-6 passes, the reader will readily understand that doubling the number of passes (from 2-3 to 5-6 passes) is not a viable option for large scale-industrial processes, which often require processing thousands of liters of cannabis-infused product.

Example 2 - Stability testing in beverage products

[0102] In this example, 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.

Table 3 stability at 25°C in a glass container

Table 4 stability at 40°C in a glass container Table 5 stability at 25°C and 40°C in a beer can

[0103] 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.

Example 3 - Stability testing

[0104] In this example, the stability of a cannabinoid emulsification system in accordance with an embodiment of the present disclosure was tested alone (concentrated or diluted form) or in combination with compounds typically found in beverage bases I beverage products according to Test Method 2.

[0105] The results are reproduced in Tables 6-7, which include qualitative and quantitative assessments, respectively.

[0106] The 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

Table 7

[0107] In Tables 6 and 7, when a particle size is shown with two values (for example, Table 7, row Q, T = 4 weeks), this means that the nanoemulsion has a bi-modal particle size distribution.

[0108] As can be shown in Tables 6-7, 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.

Example 4

[0109] In this example, 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 Tocobiol™ was added to the oil phase and that the synthetic chelating agent EDTA was added to the concentrated emulsion after the GEA homogenizing process.

[0110] All samples were filled to volume capacity of the container (glass vials filled to 15mL and cans filled to 40mL). All sample solutions had their headspace purged using argon gas in their final containers prior to sealing. All samples were pasteurized at 140F for 10 minutes. All samples (excepting standards) contain 0.5% tocobiol and 0.01 % EDTA w/w. All samples contained 0.3 mg/ml of THC. The results are reproduced in Tables 8-11 , which include qualitative (table 8) and quantitative (tables 9-11) assessments, respectively. Table 8

Table 9

Table 10 Table 11

[0111] As can be shown in Tables 8-11 , 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. Further, these tables show that including Tocobiol and EDTA does not negatively impact the properties of the nanoemulsion generated with the cannabinoid emulsification system. Furthermore, while 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.

[0112] Other examples of implementations will become apparent to the reader in view of the teachings of the present description and as such, will not be further described here.

[0113] Note that titles or subtitles may be used throughout the present disclosure for convenience of a reader, but in no way these should limit the scope of the invention. Moreover, certain theories may be proposed and disclosed herein; however, in no way they, whether they are right or wrong, should limit the scope of the invention so long as the invention is practiced according to the present disclosure without regard for any particular theory or scheme of action.

[0114] As used herein, articles such as “a” and “an”, are understood to mean one or more of what is claimed or described. [0115] As used herein, the terms “comprises”, “comprising”, “include”, “includes”, “including”, “contain”, “contains” and “containing” are meant to be non-limiting, i.e., other steps and other sections which do not affect the end of result can be added. The above terms encompass the terms “consisting of’ and “consisting essentially of’.

[0116] As used herein, the terms “around”, “about” or “approximately” shall generally mean within the error margin generally accepted in the art. For example, 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 %.

[0117] As used herein, 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.

[0118] All references cited throughout the specification are hereby incorporated by reference in their entirety for all purposes.

[0119] Reference throughout the specification to “some embodiments”, and so forth, means that a particular element (e.g., feature, structure, and/or characteristic) described in connection with the invention is included in at least one embodiment described herein, and may or may not be present in other embodiments. In addition, it is to be understood that the described inventive features may be combined in any suitable manner in the various embodiments.

[0120] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. In the case of conflict, the present document, including definitions will control the meaning of such terms.

[0121] Although various embodiments of the disclosure have been described and illustrated, it will be apparent to those skilled in the art considering the present description that numerous modifications and variations can be made. The scope of the invention is defined more particularly in the appended claims.