CANNABINOID EMULSIONS

Abstract

This technology described in this specification pertain to emulsions comprising a continuous aqueous phase, a disperse oil phase comprising a cannabinoid, and an emulsifier comprising quillaja saponin, wherein said disperse oil phase has a median particle size (d50) of 200 nm or less, and wherein the weight fraction of the disperse oil phase in the emulsion is at least 35 wt. % based on the weight of the emulsion; and/or the weight ratio of water to disperse oil phase in the emulsion is less than 1.15:1.0.

Claims

1. An emulsion comprising (i) a continuous aqueous phase, (ii) a disperse oil phase comprising a cannabinoid, and (iii) an emulsifier comprising quillaja saponin, wherein said disperse oil phase has a median particle size (d50) of 200 nm or less, and wherein a. the weight fraction of the disperse oil phase in the emulsion is at least 35 wt. % based on the weight of the emulsion; and/or b. the weight ratio of water to disperse oil phase in the emulsion is less than 1.15:1.0.

2. The emulsion according to claim 1, wherein the weight fraction of the disperse oil phase in the emulsion is at least 40 wt. % based on the weight of the emulsion, or at least 45 wt. % based on the weight of the emulsion.

3. The emulsion according to claim 1, wherein the weight fraction of the disperse oil phase in the emulsion is 60 wt. % or less based on the weight of the emulsion, or 55 wt. % or less based on the weight of the emulsion.

4. The emulsion according to claim 1, wherein the weight ratio of water to disperse oil phase in the emulsion is less than 1.15:1.0. 1.1:1.0.

5. The emulsion according to claim 1, wherein the weight ratio of water to disperse oil phase in the emulsion is at least 0.8:1.0.

6. The emulsion according to claim 1, wherein said disperse oil phase has a median particle size (d50) from 50 nm to 180 nm.

7. The emulsion according to claim 1, wherein the weight ratio of quillaja saponin to said disperse oil phase is from 0.02:1 to 0.5:1.

8. The emulsion according to claim 1, wherein the weight ratio of quillaja saponin to said disperse oil phase is from 0.03:1 to 0.4:1.

9. The emulsion according to claim 1, wherein said cannabinoid is a) one or more of tetrahydrocannabinol (THC) and cannabidiol (CBD) or is b) selected from the group consisting of tetrahydrocannabinol (THC) and cannabidiol (CBD) cannabigerol (CBG), cannabichromene (CBC), cannabinol (CBN), cannabielsoin (CBE), iso-tetrahydrocannabinol (iso-THC), cannabicyclol (CBL), cannabicitran (CBT), cannabivarin (CBV), tetrahydrocannabivarin (THCV), THCP (tetrahydrocannabiphorol), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethyl ether (CBGM), tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA) or mixtures thereof.

10. The emulsion according to claim 1, wherein, the disperse oil phase comprises a vegetable oil.

11. The emulsion according to 1, wherein said vegetable oil is selected from the group consisting of medium chain triglyceride (MCT) oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, rapeseed oil, safflower oil, sesame oil, soybean oil, sunflower oil, and canola oil.

12. The emulsion according to claim 1, wherein the weight ratio of said cannabinoid to vegetable oil is between 1:0.1 and 1:9.

13-16. (canceled)

17. A method for preparing an emulsion comprising: i. providing an aqueous phase comprising water and an emulsifier comprising quillaja saponin, ii. providing an oil phase comprising an oil and a cannabinoid extract, iii. mixing said aqueous phase and said oil phase to create a pre-emulsion; and iv. homogenizing said pre-emulsion to obtain the emulsion. wherein the emulsion has a disperse oil phase having a median particle size (d50) of 200 nm or less, and wherein the weight fraction of the disperse oil phase in the emulsion is at least 35 wt. % based on the weight of the emulsion.

18. The method of claim 17 wherein the weight ratio of water to disperse oil phase in the emulsion is less than 1.15:1.0.

19. The method of claim 17 wherein the weight ratio of quillaja saponin to said disperse oil phase is from 0.02:1 to 0.5:1.

20. The method of claim 17, wherein said cannabinoid is a) one or more of tetrahydrocannabinol (THC) and cannabidiol (CBD) or is b) selected from the group consisting of tetrahydrocannabinol (THC) and cannabidiol (CBD) cannabigerol (CBG), cannabichromene (CBC), cannabinol (CBN), cannabielsoin (CBE), iso-tetrahydrocannabinol (iso-THC), cannabicyclol (CBL), cannabicitran (CBT), cannabivarin (CBV), tetrahydrocannabivarin (THCV), THCP (tetrahydrocannabiphorol), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethyl ether (CBGM), tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA) or mixtures thereof.

21. The method of claim 17, wherein, the oil phase comprises a vegetable oil selected from the group consisting of medium chain triglyceride (MCT) oil, coconut oil, corn oil, cottonseed oil, olive oil, palm oil, peanut oil, rapeseed oil, safflower oil, sesame oil, soybean oil, sunflower oil, and canola oil.

22. The method of claim 17, wherein the weight ratio of said cannabinoid to vegetable oil is between 1:0.1 and 1:9, for instance between 1:3 and 3:1.

23. A method comprising: a) mixing an emulsion comprising (i) a continuous aqueous phase, (ii) a disperse oil phase comprising a cannabinoid, and (iii) an emulsifier comprising quillaja saponin, wherein said disperse oil phase has a median particle size (d50) of 200 nm or less, and wherein the weight fraction of the disperse oil phase in the emulsion is at least 35 wt. % based on the weight of the emulsion, and b) and a second edible ingredient to form a beverage.

24. The method of claim 23 wherein the beverage has a Turbiscan Stability Index of less than 4.

Description

EXAMPLES

[0062] The embodiment of the technology described in this specification are numbered. Comparative examples are indicated using letters.

Example 1

Emulsion Preparation Using High Pressure Homogenization

[0063] CBD nanoemulsions using quillaja extract as the emulsifier and hemp-based CBD isolate powder as the CBD source were prepared according to the formulations of Table 1.

TABLE-US-00001 TABLE 1 CBD emulsion formulations using quillaja extract as the emulsifier. Powder Quillaja MCT CBD Citric Ascorbic Potassium Sodium Sam- Extract Oil Isolate Acid Acid Sorbate Benzoate Water ple (%) (%) (%) (%) (%) (%) (%) (%) 1 15.00 30.00 20.00 0.20 0.20 0.10 0.10 34.40 A 15.00 3.00 2.00 0.20 0.20 0.10 0.10 79.40

[0064] The quillaja extract was in powdered form (QDP Ultra Organic from Desert King) and contains 65%-75% saponin. The CBD isolate powder ((>98% purity) was purchased from Treehouse Biotech (Longmont, Colo.).

[0065] The sodium benzoate and potassium sorbate were first dissolved in room temperature deionized water under stirring for 5 minutes. The quillaja extract was added to the solution and the mixture was stirred for 30 minutes. In a separate beaker, MCT oil was heated on a hot plate to 65° C. The CBD isolate powder was added to the MCT oil mixed until fully dissolved. The CBD oil solution was allowed to cool to room temperature.

[0066] A pre-emulsion was made by adding the oil phase into the aqueous phase under high shear mixing conditions: 10,000 rpm for 2 minutes in a Ross Model HSM-LCI-T.

[0067] The pre-emulsion was homogenized via high pressure homogenization at 344.7 bar (5000 psi) for 5 passes (1.sup.st stage=4500 psi/2.sup.nd stage=500 psi). The citric acid and ascorbic acid were added and the emulsion mixed an additional 5 minutes.

[0068] The particle size of the emulsion was immediately determined using a laser diffraction particle size analyzer (Malvern Mastersizer 2000). The median particle size (d.sub.50), d10, d90, and d[4,3] were recorded.

Beverage Preparation

[0069] Beverages were prepared from the obtained nanoemulsions, such that the CBD content was 25 mg per 355 g (˜12 fl oz) of beverage. The beverages comprised 0.1 wt. % Sodium benzoate and 0.3 wt. % citric acid. Deionized water was added such that a total of 355 g beverage was obtained.

[0070] The citric acid and sodium benzoate were added to room temperature deionized water and mixed via magnetic stir bar for 5 minutes. The CBD nanoemulsion was added to the solution and lightly mixed. A 12 oz (˜355 mL) bottle was filled with the solution and capped.

[0071] The bottle was stored horizontally at room temperature without manipulation for 21 days. After 21 days, the beverage was visually examined without manipulation for the presence of a white ring at the top of the beverage (creaming of the CBD emulsion). The beverage can also be examined for sedimentation.

[0072] The results of the trials are shown in Table 2 below.

TABLE-US-00002 TABLE 2 Particle size, beverage stability, and TSI results for emulsions made using quillaja extract as the emulsifier and CBD isolate powder as the CBD source. Sam- d10 d50 d90 d[4.3] Beverage TSI ple Pass (nm) (nm) (nm) (nm) Stability (Global) 1 5 74 138 256 161 Stable 3.4 A 5 102 254 958 415 Slight Ring 4.6

[0073] Thus, it can be observed that the nanoemulsions, having a higher oil load, show smaller particle sizes than the comparative example and can produce beverages having improved stability.

Example 2

Emulsion Preparation Using a Microfluidizer

[0074] CBD nanoemulsions were produced using a Microfluidizer (Microfluidics, Model: M-110EH) according to the formulations and processing instructions shown in Table 3. The microfluidizer has the capability to process emulsions at higher pressure and thus leads to more stable nanoemulsions and beverages. The interaction chamber used was the F12Y-H30Z. The quillaja extract was in liquid form as Q-Naturale 200 V from Ingredion Inc and contains 13-16% saponins in an aqueous solution. The emulsions were sampled at various passes, and the final pass was used for beverage stability, turbidity, and TSI measurements.

TABLE-US-00003 TABLE 3 CBD emulsion formulations processed via microfluidization. MCT CBD Citric Ascorbic Potassium Sodium Sam- LQE Oil Isolate Acid Acid Sorbate Benzoate Water ple (%) (%) (%) (%) (%) (%) (%) (%) Passes B 35.0 6.0 4.0 0.2 0.2 0.1 0.1 54.4 1, 3, 5 C 35.0 12.0 8.0 0.2 0.2 0.1 0.1 44.4 1, 3, 5 D 35.0 18.0 12.0 0.2 0.2 0.1 0.1 34.4 1, 3, 5 2 35.0 24.0 16.0 0.2 0.2 0.1 0.1 24.4 1, 3, 5 3 35.0 30.0 20.0 0.2 0.2 0.1 0.1 14.4 1, 3, 5, 7 4 50.0 30.0 20.0 — — — — — 1, 3, 5

[0075] Pre-emulsions were made according to the previously described method.

[0076] The pre-emulsions were further processed via microfluidization (Manufacturer: Microfluidics) at 2068.4 bar (30000 psi) for the specified amount of passes. Citric acid and ascorbic acid were added to the solution and mixed an additional 5 minutes. The particle size of the emulsion was immediately tested using a laser diffraction particle size analyzer (Manufacturer: Malvern Mastersizer 2000) where the median particle size (d50), d10, d90, and d[4.3] were recorded.

Beverage Preparation

[0077] Beverages were prepared according to the method of Example 1.

[0078] Beverage stability and TSI were measured according to the previously described methods.

TABLE-US-00004 TABLE 4 Particle size of emulsion, beverage stability, and TSI results for emulsions made via microfluidization. Sam- d10 d50 d90 D[4.3] Beverage TSI ple Pass (nm) (nm) (nm) (nm) Stability (Global) B 1 116 197.93 315.54 212.5 — — 3 101.19 161.27 241.21 166.96 — — 5 92.03 143.32 210.32 147.95 Stable 0.1 C 1 116.99 197.18 311.61 509.32 — — 3 98.1 154.56 227.11 159.72 — — 5 91.05 140.89 205.55 145.34 Stable 0.8 D 1 116.24 192.46 294.03 200.59 — — 3 95.19 149.03 218.49 153.79 — — 5 88.74 136.11 196.51 140.36 Stable 1.7 2 1 129.51 213.62 322.09 220.8 — — 3 93.96 146.32 214.16 150.88 — — 5 82.76 126.04 183.07 130.01 Stable 1.0 3 1 122.71 201.33 299.4 207.45 — — 3 97.46 151.03 219.4 155.48 — — 5 92.32 141.85 205.21 146.05 — — 7 90.89 139.29 200.63 143.43 Stable 0.4 4 1 121.81 201.17 303.04 208.06 — — 3 88.51 135.41 195.52 139.61 — — 5 82.26 125.31 182.14 129.31 Stable 0.7

[0079] It can be observed that with increasing oil loads, the particle size, including d50 decreased.