BRODY MARCUS STEPHEN (US)
| WO2020028991A1 | 2020-02-13 | |||
| WO2021046295A1 | 2021-03-11 |
| US20140271940A1 | 2014-09-18 | |||
| US20160220593A1 | 2016-08-04 |
ELSOHLY ET AL., LIFE SCI., vol. 78, 2005, pages 539 - 48
OXIDATION IN FOODS AND BEVERAGES AND ANTIOXIDANT APPLICATIONS, 2010, ISBN: 978-1-84569-648-1
NAGUIB ET AL., JNUTR SCI VITAMINOL, vol. 49, no. 4, 2003, pages 217 - 20
| CLAIMS 1. A food additive, comprising a cannabinoid or derivative thereof, and a non-toxic carrier. 2. The food additive of claim 1, wherein the cannabinoid is cannabigerol (CBG) or a derivative thereof. 3. The food additive of claim 2, wherein the cannabinoid is cannabigerol (CBG). 4. The food additive of claim 3, wherein the food additive comprises pure CBG. 5. The food additive of any one of claims 1 to 4, wherein the food additive is substantially free of cannabinoids or derivatives thereof, other than CBG. 6. The food additive of any one of claims 1 to 5, wherein the food additive comprises no detectable amount of tetrahydrocannabinol (THC). 7. The food additive of any one of claims 1 to 6, wherein the food additive comprises no detectable amount of cannabidiol (CBD). 8. The food additive of any one of claims 1 to 7, wherein the food additive comprises an antioxidant effective amount of the cannabinoid. 9. The food additive of any one of claims 1 to 7, wherein the food additive comprises an antioxidant effective amount of cannabigerol (CBG). 10. The food additive of claim 9, wherein the antioxidant effective amount of CBG is at least about 10 ppm. 11. The food additive of claim 9, wherein the antioxidant effective amount of CBG is at least about 15 ppm. 12. The food additive of claim 9, wherein the antioxidant effective amount of CBG is at least about 30 ppm. 13. The food additive of claim 9, wherein the antioxidant effective amount of CBG is at least about 60 ppm. 14. The food additive of any one of claims 8 to 13, wherein the food additive comprises at least 3 times the antioxidant effective amount of the cannabinoid. 15. The food additive of any one of claims 8 to 13, wherein the food additive comprises at least 5 times the antioxidant effective amount of the cannabinoid. 16. The food additive of any one of claims 8 to 13, wherein the food additive comprises at least 10 times the antioxidant effective amount of the cannabinoid. 17. The food additive of any one of claims 8 to 13, wherein the food additive comprises at least 20 times the antioxidant effective amount of the cannabinoid. 18. The food additive of any one of claims 1 to 13, wherein the food additive comprises 1-3 times the antioxidant effective amount of the cannabinoid. 19. The food additive of any one of claims 1 to 13, wherein the food additive comprises 3-5 times the antioxidant effective amount of the cannabinoid. 20. The food additive of any one of claims 1 to 13, wherein the food additive comprises at least 6-10 times the antioxidant effective amount of the cannabinoid. 21. The food additive of any one of claims 1 to 13, wherein the food additive comprises at least 10-20 times the antioxidant effective amount of the cannabinoid. 22. The food additive of any one of claims 1 to 21, wherein the food additive comprises at most 400 ppm of the cannabinoid. 23. The food additive of any one of claims 1 to 21, wherein the food additive comprises at most 800 ppm of the cannabinoid. 24. The food additive of any one of claims 1 to 21, wherein the food additive comprises at most 1200 ppm of the cannabinoid. 25. The food additive of any one of claims 1 to 21, wherein the food additive comprises at most 4,000 ppm of the cannabinoid. 26. The food additive of any one of claims 1 to 21, wherein the food additive comprises at most 8,000 ppm of the cannabinoid. 27. A food product, comprising the food additive of any one of claims 1 to 26 and one or more other edible ingredients. 28. The food product of claim 27, wherein the food additive is 1-10% weight by weight (w/w) of the food product. 29. The food product of claim 27, wherein the food additive is 10-20% w/w of the food product. 30. A food product, comprising a cannabinoid or derivative thereof. 31. The food product of claim 30, wherein the cannabinoid is cannabigerol (CBG) or a derivative thereof. 32. The food product of claim 31, wherein the cannabinoid is cannabigerol (CBG). 33. The food product of claim 32, wherein the food product comprises pure CBG. 34. The food product of any one of claims 30 to 33, wherein the food product is substantially free of cannabinoids or derivatives thereof, other than CBG. 35. The food product of any one of claims 30 to 34, wherein the food product comprises no detectable amount of tetrahydrocannabinol (THC). 36. The food product of any one of claims 30 to 35, wherein the food product comprises no detectable amount of cannabidiol (CBD). 37. The food product of any one of claims 30 to 36, wherein the food product comprises an antioxidant effective amount of the cannabinoid. 38. The food product of any one of claims 30 to 36, wherein the food product comprises an antioxidant effective amount of cannabigerol (CBG). 39. The food product of claim 38, wherein the antioxidant effective amount of CBG is at least about 10 ppm. 40. The food product of claim 38, wherein the antioxidant effective amount of CBG is at least about 15 ppm. 41. The food product of claim 38, wherein the antioxidant effective amount of CBG is at least about 30 ppm. 42. The food product of claim 38, wherein the antioxidant effective amount of CBG is at least about 60 ppm. 43. The food product of any one of claims 30 to 42, wherein the food product comprises at most 20 times the antioxidant effective amount of the cannabinoid. 44. The food product of any one of claims 30 to 42, wherein the food product comprises at most 10 times the antioxidant effective amount of the cannabinoid. 45. The food product of any one of claims 30 to 42, wherein the food product comprises at most 5 times the antioxidant effective amount of the cannabinoid. 46. The food product of any one of claims 30 to 42, wherein the food product comprises at most 3 times the antioxidant effective amount of the cannabinoid. 47. The food product of any one of claims 30 to 42, wherein the food product comprises 1-2 times the antioxidant effective amount of the cannabinoid. 48. The food product of any one of claims 30 to 42, wherein the food product comprises 2-4 times the antioxidant effective amount of the cannabinoid. 49. The food product of any one of claims 30 to 42, wherein the food product comprises at least 4-6 times the antioxidant effective amount of the cannabinoid. 50. The food product of any one of claims 30 to 42, wherein the food product comprises at least 6-10 times the antioxidant effective amount of the cannabinoid. 51. The food product of any one of claims 30 to 50, wherein the food product comprises at most 300 ppm of the cannabinoid. 52. The food product of any one of claims 30 to 50, wherein the food product comprises at most 200 ppm of the cannabinoid. 53. The food product of any one of claims 30 to 50, wherein the food product comprises at most 150 ppm of the cannabinoid. 54. The food product of any one of claims 30 to 50, wherein the food product comprises at most 100 ppm of the cannabinoid. 55. The food product of any one of claims 30 to 50, wherein the food product comprises at most 80 ppm of the cannabinoid. 56. The food product of any one of claims 27 to 55, wherein the food product is an oil. 57. The food product of any one of claims 27 to 55, wherein the food product is a suspension. 58. The food product of any one of claims 27 to 55, wherein the food product is an aqueous solution. 59. The food product of any one of claims 27 to 55, wherein the food product is a salad dressing or bouillon. 60. The food product of any one of claims 27 to 55, wherein the food product is a sauce, finished oil, condiment, or marinade. 61. The food product of any one of claims 27 to 60, wherein the food product exhibits decreased rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 62. The food product of any one of claims 27 to 60, wherein the food product exhibits 10% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 63. The food product of any one of claims 27 to 60, wherein the food product exhibits 20% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 64. The food product of any one of claims 27 to 60, wherein the food product exhibits 30% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 65. The food product of any one of claims 27 to 60, wherein the food product exhibits 50% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 66. The food product of any one of claims 27 to 60, wherein the food product exhibits 80% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 67. The food product of any one of claims 61 to 66, wherein the predetermined time is one week. 68. The food product of any one of claims 61 to 66, wherein the predetermined time is one month. 69. A method for making a food additive, comprising adding a composition comprising a cannabinoid to a non-toxic carrier, thereby making the food additive. 70. The method of claim 69, wherein the cannabinoid is cannabigerol (CBG) or a derivative thereof. 71. The method of claim 70, wherein the cannabinoid is cannabigerol (CBG). 72. The method of claim 71, wherein the composition comprises pure CBG. 73. The method of any one of claims 69 to 72, wherein the composition is substantially free of cannabinoids or derivatives thereof, other than CBG. 74. The method of any one of claims 30 to 34, wherein the composition comprises no detectable amount of tetrahydrocannabinol (THC). 75. The method of any one of claims 30 to 35, wherein the composition comprises no detectable amount of cannabidiol (CBD). 76. The method of any one of claims 69 to 75, wherein the food additive comprises an antioxidant effective amount of the cannabinoid. 77. The method of any one of claims 69 to 75, wherein the food additive comprises an antioxidant effective amount of cannabigerol (CBG). 78. The method of claim 77, wherein the antioxidant effective amount of CBG is at least about 10 ppm. 79. The method of claim 77, wherein the antioxidant effective amount of CBG is at least about 15 ppm. 80. The method of claim 77, wherein the antioxidant effective amount of CBG is at least about 30 ppm. 81. The method of claim 77, wherein the antioxidant effective amount of CBG is at least about 60 ppm. 82. The method of any one of claims 76 to 81, wherein the food additive comprises at least 3 times the antioxidant effective amount of the cannabinoid. 83. The method of any one of claims 76 to 81, wherein the food additive comprises at least 5 times the antioxidant effective amount of the cannabinoid. 84. The method of any one of claims 76 to 81, wherein the food additive comprises at least 10 times the antioxidant effective amount of the cannabinoid. 85. The method of any one of claims 76 to 81, wherein the food additive comprises at least 20 times the antioxidant effective amount of the cannabinoid. 86. The method of any one of claims 69 to 81, wherein the food additive comprises 1-3 times the antioxidant effective amount of the cannabinoid. 87. The method of any one of claims 69 to 81, wherein the food additive comprises 3-5 times the antioxidant effective amount of the cannabinoid. 88. The method of any one of claims 69 to 81, wherein the food additive comprises at least 6-10 times the antioxidant effective amount of the cannabinoid. 89. The method of any one of claims 69 to 81, wherein the food additive comprises at least 10- 20 times the antioxidant effective amount of the cannabinoid. 90. The method of any one of claims 69 to 89, wherein the food additive comprises at most 400 ppm of the cannabinoid. 91. The method of any one of claims 69 to 89, wherein the food additive comprises at most 800 ppm of the cannabinoid. 92. The method of any one of claims 69 to 89, wherein the food additive comprises at most 1200 ppm of the cannabinoid. 93. The method of any one of claims 69 to 89, wherein the food additive comprises at most 4,000 ppm of the cannabinoid. 94. The method of any one of claims 69 to 89, wherein the food additive comprises at most 8,000 ppm of the cannabinoid. 95. A method for making a food product, comprising adding a food additive according to any one of claims 1 to 26 to one or more edible ingredients, thereby making the food product. 96. A method for making a food product, comprising adding a composition comprising a cannabinoid to a non-toxic carrier, thereby making a food additive; and adding the food additive to one or more edible ingredients, thereby making the food product. 97. A method for making a food product, comprising adding a composition comprising a cannabinoid to one or more edible ingredients, thereby making the food product. 98. The method of any one of claims claim 97, wherein the cannabinoid is cannabigerol (CBG) or a derivative thereof. 99. The method of claim 98, wherein the cannabinoid is cannabigerol (CBG). 100. The method of claim 99, wherein the composition comprises pure CBG. 101. The method of any one of claims 95 to 100, wherein the composition is substantially free of cannabinoids or derivatives thereof, other than CBG. 102. The method of any one of claims 95 to 101, wherein the composition comprises no detectable amount of tetrahydrocannabinol (THC). 103. The method of any one of claims 95 to 102, wherein the composition comprises no detectable amount of cannabidiol (CBD). 104. The method of any one of claims 95 to 103, wherein the food product comprises an antioxidant effective amount of the cannabinoid. 105. The method of any one of claims 95 to 103, wherein the food product comprises an antioxidant effective amount of cannabigerol (CBG). 106. The method of claim 105, wherein the antioxidant effective amount of CBG is at least about 10 ppm. 107. The method of claim 105, wherein the antioxidant effective amount of CBG is at least about 15 ppm. 108. The method of claim 105, wherein the antioxidant effective amount of CBG is at least about 30 ppm. 109. The method of claim 105, wherein the antioxidant effective amount of CBG is at least about 60 ppm. 110. The method of any one of claims 104 to 109, wherein the food product comprises at most 20 times the antioxidant effective amount of the cannabinoid. 111. The method of any one of claims 104 to 109, wherein the food product comprises at most 10 times the antioxidant effective amount of the cannabinoid. 112. The method of any one of claims 104 to 109, wherein the food product comprises at most 5 times the antioxidant effective amount of the cannabinoid. 113. The method of any one of claims 104 to 109, wherein the food product comprises at most 3 times the antioxidant effective amount of the cannabinoid. 114. The method of any one of claims 104 to 109, wherein the food product comprises 1- 2 times the antioxidant effective amount of the cannabinoid. 115. The method of any one of claims 104 to 109, wherein the food product comprises 2- 4 times the antioxidant effective amount of the cannabinoid. 116. The method of any one of claims 104 to 109, wherein the food product comprises at least 4-6 times the antioxidant effective amount of the cannabinoid. 117. The method of any one of claims 104 to 109, wherein the food product comprises at least 6-10 times the antioxidant effective amount of the cannabinoid. 118. The method of any one of claims 95 to 117, wherein the food product comprises at most 300 ppm of the cannabinoid. 119. The method of any one of claims 95 to 117, wherein the food product comprises at most 200 ppm of the cannabinoid. 120. The method of any one of claims 95 to 117, wherein the food product comprises at most 150 ppm of the cannabinoid. 121. The method of any one of claims 95 to 117, wherein the food product comprises at most 100 ppm of the cannabinoid. 122. The method of any one of claims 95 to 117, wherein the food product comprises at most 80 ppm of the cannabinoid. 123. The method of any one of claims 95 to 122, wherein the food product is an oil. 124. The method of any one of claims 95 to 122, wherein the food product is a suspension. 125. The method of any one of claims 95 to 122, wherein the food product is an aqueous solution. 126. The method of any one of claims 95 to 122, wherein the food product is a salad dressing or bouillon. 127. The method of any one of claims 95 to 122, wherein the food product is a sauce, finished oil, condiment, or marinade. 128. The method of any one of claims 95 to 127, wherein the food product exhibits decreased rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 129. The method of any one of claims 95 to 127, wherein the food product exhibits 10% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 130. The method of any one of claims 95 to 127, wherein the food product exhibits 20% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 131. The method of any one of claims 95 to 127, wherein the food product exhibits 30% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 132. The method of any one of claims 95 to 127, wherein the food product exhibits 50% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 133. The method of any one of claims 95 to 127, wherein the food product exhibits 80% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. 134. The method of any one of claims 128 to 133, wherein the predetermined time is one week. 135. The method of any one of claims 128 to 133, wherein the predetermined time is one month. |
FIELD OF THE INVENTION
[0001] This disclosure relates generally to antioxidants as food additives and food products.
BACKGROUND
[0002] Lipid oxidation is a principal cause of deterioration of foods and limits shelf life of otherwise stable foods. In bulk oils, the reaction of unsaturated fatty acids with oxygen forms hydroperoxides, which can further propagate through a free radical chain reaction (auto-oxidation). Radical terminators are antioxidants that prevent lipid oxidation by terminating the free radical chains and stopping autoxidation. There is a need in the art for novel food additives having antioxidant properties.
SUMMARY
[0003] This disclosure provides cannabinoids as antioxidants and uses thereof. The cannabinoid may be used as a food additive, e.g., compositions comprising the cannabinoid, in an effective amount, and a non-toxic carrier. The food additives disclosed herein may, when used in a food product, reduce oxidative degradation of, increase the stability of, and/or reduce, prevent, or delay spoilage of the food product. Further provided are methods of making and using the disclosed cannabinoid antioxidants.
[0004] In one aspect, the disclosure provides a cannabinoid or derivative thereof, and a non-toxic carrier.
[0005] In some variations, the cannabinoid is cannabigerol (CBG) or a derivative thereof. [0006] In some variations, the cannabinoid is cannabigerol (CBG).
[0007] In some variations, the food additive comprises pure CBG.
[0008] In some variations, the food additive is substantially free of cannabinoids or derivatives thereof, other than CBG.
[0009] In some variations, the food additive comprises no detectable amount of tetrahydrocannabinol (THC).
[0010] In some variations, the food additive comprises no detectable amount of cannabidiol (CBD).
[0011] In some variations, the food additive comprises an antioxidant effective amount of the cannabinoid.
[0012] In some variations, the food additive comprises an antioxidant effective amount of cannabigerol (CBG).
[0013] In some variations, the antioxidant effective amount of CBG is at least about 10 ppm.
[0014] In some variations, the antioxidant effective amount of CBG is at least about 15 ppm.
[0015] In some variations, the antioxidant effective amount of CBG is at least about 30 ppm.
[0016] In some variations, the antioxidant effective amount of CBG is at least about 60 ppm.
[0017] In some variations, the food additive comprises at least 3 times the antioxidant effective amount of the cannabinoid.
[0018] In some variations, the food additive comprises at least 5 times the antioxidant effective amount of the cannabinoid.
[0019] In some variations, the food additive comprises at least 10 times the antioxidant effective amount of the cannabinoid. [0020] In some variations, the food additive comprises at least 20 times the antioxidant effective amount of the cannabinoid.
[0021] In some variations, the food additive comprises 1-3 times the antioxidant effective amount of the cannabinoid.
[0022] In some variations, the food additive comprises 3-5 times the antioxidant effective amount of the cannabinoid.
[0023] In some variations, the food additive comprises at least 6-10 times the antioxidant effective amount of the cannabinoid.
[0024] In some variations, the food additive comprises at least 10-20 times the antioxidant effective amount of the cannabinoid.
[0025] In some variations, the food additive comprises at most 400 ppm of the cannabinoid.
[0026] In some variations, the food additive comprises at most 800 ppm of the cannabinoid.
[0027] In some variations, the food additive comprises at most 1200 ppm of the cannabinoid.
[0028] In some variations, the food additive comprises at most 4,000 ppm of the cannabinoid.
[0029] In some variations, the food additive comprises at most 8,000 ppm of the cannabinoid.
[0030] In another aspect, the disclosure provides food product comprising the food additive of any one of claims 1 to 26 and one or more other edible ingredients.
[0031] In some variations, the food additive is 1-10% weight by weight (w/w) of the food product.
[0032] In some variations, the food additive is 10-20% w/w of the food product.
[0033] In another aspect, the disclosure provides a food product comprising a cannabinoid or derivative thereof.
[0034] In some variations, the cannabinoid is cannabigerol (CBG) or a derivative thereof. [0035] In some variations, the cannabinoid is cannabigerol (CBG).
[0036] In some variations, the food product comprises pure CBG.
[0037] In some variations, the food product is substantially free of cannabinoids or derivatives thereof, other than CBG.
[0038] In some variations, the food product comprises no detectable amount of tetrahydrocannabinol (THC).
[0039] In some variations, the food product comprises no detectable amount of cannabidiol (CBD).
[0040] In some variations, the food product comprises an antioxidant effective amount of the cannabinoid.
[0041] In some variations, the food product comprises an antioxidant effective amount of cannabigerol (CBG).
[0042] In some variations, the antioxidant effective amount of CBG is at least about 10 ppm.
[0043] In some variations, the antioxidant effective amount of CBG is at least about 15 ppm.
[0044] In some variations, the antioxidant effective amount of CBG is at least about 30 ppm.
[0045] In some variations, the antioxidant effective amount of CBG is at least about 60 ppm.
[0046] In some variations, the food product comprises at most 20 times the antioxidant effective amount of the cannabinoid.
[0047] In some variations, the food product comprises at most 10 times the antioxidant effective amount of the cannabinoid.
[0048] In some variations, the food product comprises at most 5 times the antioxidant effective amount of the cannabinoid. [0049] In some variations, the food product comprises at most 3 times the antioxidant effective amount of the cannabinoid.
[0050] In some variations, the food product comprises 1-2 times the antioxidant effective amount of the cannabinoid.
[0051] In some variations, the food product comprises 2-4 times the antioxidant effective amount of the cannabinoid.
[0052] In some variations, the food product comprises at least 4-6 times the antioxidant effective amount of the cannabinoid.
[0053] In some variations, the food product comprises at least 6-10 times the antioxidant effective amount of the cannabinoid.
[0054] In some variations, the food product comprises at most 300 ppm of the cannabinoid.
[0055] In some variations, the food product comprises at most 200 ppm of the cannabinoid.
[0056] In some variations, the food product comprises at most 150 ppm of the cannabinoid.
[0057] In some variations, the food product comprises at most 100 ppm of the cannabinoid.
[0058] In some variations, the food product comprises at most 80 ppm of the cannabinoid.
[0059] In some variations, the food product is an oil.
[0060] In some variations, the food product is a suspension.
[0061] In some variations, the food product is an aqueous solution.
[0062] In some variations, the food product is a salad dressing or bouillon.
[0063] In some variations, the food product is a sauce, finished oil, condiment, or marinade.
[0064] In some variations, the food product exhibits decreased rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. [0065] In some variations, the food product exhibits 10% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[0066] In some variations, the food product exhibits 20% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[0067] In some variations, the food product exhibits 30% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[0068] In some variations, the food product exhibits 50% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[0069] In some variations, the food product exhibits 80% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[0070] In some variations, the predetermined time is one week.
[0071] In some variations, the predetermined time is one month.
[0072] In another aspect, the disclosure provides a method for making a food additive, comprising adding a composition comprising a cannabinoid to a non-toxic carrier, thereby making the food additive.
[0073] In some variations, the cannabinoid is cannabigerol (CBG) or a derivative thereof.
[0074] In some variations, the cannabinoid is cannabigerol (CBG).
[0075] In some variations, the composition comprises pure CBG. [0076] In some variations, the composition is substantially free of cannabinoids or derivatives thereof, other than CBG.
[0077] In some variations, the composition comprises no detectable amount of tetrahydrocannabinol (THC).
[0078] In some variations, the composition comprises no detectable amount of cannabidiol (CBD).
[0079] In some variations, the food additive comprises an antioxidant effective amount of the cannabinoid.
[0080] In some variations, the food additive comprises an antioxidant effective amount of cannabigerol (CBG).
[0081] In some variations, the antioxidant effective amount of CBG is at least about 10 ppm.
[0082] In some variations, the antioxidant effective amount of CBG is at least about 15 ppm.
[0083] In some variations, the antioxidant effective amount of CBG is at least about 30 ppm.
[0084] In some variations, the antioxidant effective amount of CBG is at least about 60 ppm.
[0085] In some variations, the food additive comprises at least 3 times the antioxidant effective amount of the cannabinoid.
[0086] In some variations, the food additive comprises at least 5 times the antioxidant effective amount of the cannabinoid.
[0087] In some variations, the food additive comprises at least 10 times the antioxidant effective amount of the cannabinoid.
[0088] In some variations, the food additive comprises at least 20 times the antioxidant effective amount of the cannabinoid. [0089] In some variations, the food additive comprises 1-3 times the antioxidant effective amount of the cannabinoid.
[0090] In some variations, the food additive comprises 3-5 times the antioxidant effective amount of the cannabinoid.
[0091] In some variations, the food additive comprises at least 6-10 times the antioxidant effective amount of the cannabinoid.
[0092] In some variations, the food additive comprises at least 10-20 times the antioxidant effective amount of the cannabinoid.
[0093] In some variations, the food additive comprises at most 400 ppm of the cannabinoid.
[0094] In some variations, the food additive comprises at most 800 ppm of the cannabinoid.
[0095] In some variations, the food additive comprises at most 1200 ppm of the cannabinoid. [0096] In some variations, the food additive comprises at most 4,000 ppm of the cannabinoid. [0097] In some variations, the food additive comprises at most 8,000 ppm of the cannabinoid. [0098] A method for making a food product, comprising adding a food additive according to any one of claims 1 to 26 to one or more edible ingredients, thereby making the food product.
[0099] A method for making a food product, comprising adding a composition comprising a cannabinoid to a non-toxic carrier, thereby making a food additive; and adding the food additive to one or more edible ingredients, thereby making the food product.
[00100] A method for making a food product, comprising adding a composition comprising a cannabinoid to one or more edible ingredients, thereby making the food product.
[00101] In some variations, the cannabinoid is cannabigerol (CBG) or a derivative thereof.
[00102] In some variations, the cannabinoid is cannabigerol (CBG).
[00103] In some variations, the composition comprises pure CBG. [00104] In some variations, the composition is substantially free of cannabinoids or derivatives thereof, other than CBG.
[00105] In some variations, the composition comprises no detectable amount of tetrahydrocannabinol (THC).
[00106] In some variations, the composition comprises no detectable amount of cannabidiol (CBD).
[00107] In some variations, the food product comprises an antioxidant effective amount of the cannabinoid.
[00108] In some variations, the food product comprises an antioxidant effective amount of cannabigerol (CBG).
[00109] In some variations, the antioxidant effective amount of CBG is at least about 10 ppm. [00110] In some variations, the antioxidant effective amount of CBG is at least about 15 ppm. [00111] In some variations, the antioxidant effective amount of CBG is at least about 30 ppm. [00112] In some variations, the antioxidant effective amount of CBG is at least about 60 ppm. [00113] In some variations, the food product comprises at most 20 times the antioxidant effective amount of the cannabinoid.
[00114] In some variations, the food product comprises at most 10 times the antioxidant effective amount of the cannabinoid.
[00115] In some variations, the food product comprises at most 5 times the antioxidant effective amount of the cannabinoid.
[00116] In some variations, the food product comprises at most 3 times the antioxidant effective amount of the cannabinoid. [00117] In some variations, the food product comprises 1-2 times the antioxidant effective amount of the cannabinoid.
[00118] In some variations, the food product comprises 2-4 times the antioxidant effective amount of the cannabinoid.
[00119] In some variations, the food product comprises at least 4-6 times the antioxidant effective amount of the cannabinoid.
[00120] In some variations, the food product comprises at least 6-10 times the antioxidant effective amount of the cannabinoid.
[00121] In some variations, the food product comprises at most 300 ppm of the cannabinoid.
[00122] In some variations, the food product comprises at most 200 ppm of the cannabinoid.
[00123] In some variations, the food product comprises at most 150 ppm of the cannabinoid.
[00124] In some variations, the food product comprises at most 100 ppm of the cannabinoid.
[00125] In some variations, the food product comprises at most 80 ppm of the cannabinoid.
[00126] In some variations, the food product is an oil.
[00127] In some variations, the food product is a suspension.
[00128] In some variations, the food product is an aqueous solution.
[00129] In some variations, the food product is a salad dressing or bouillon.
[00130] In some variations, the food product is a sauce, finished oil, condiment, or marinade.
[00131] In some variations, the food product exhibits decreased rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid. [00132] In some variations, the food product exhibits 10% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[00133] In some variations, the food product exhibits 20% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[00134] In some variations, the food product exhibits 30% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[00135] In some variations, the food product exhibits 50% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[00136] In some variations, the food product exhibits 80% less rancidity and/or deterioration in sensory attributes after a predetermined time compared to a same food product lacking the cannabinoid.
[00137] In some variations, the predetermined time is one week.
[00138] In some variations, the predetermined time is one month.
BRIEF DESCRIPTION OF THE DRAWINGS
[00139] FIG. 1 shows the chemical reactions underlying lipid oxidation and termination by antioxidants.
[00140] FIG. 2 shows chemical structures of various known radical terminators. [00141] FIG. 3 shows sensory analysis of CBG-containing salad dressing subjected to accelerated aging. Samples were ranked using the Likert scale.
DETAILED DESCRIPTION
[00142] This disclosure provides cannabinoids as antioxidants and uses thereof. The cannabinoid may be used as a food additive, e.g., compositions comprising the cannabinoid, in an effective amount, and a non-toxic carrier. The food additives disclosed herein may, when used in a food product, reduce oxidative degradation of, increase the stability of, and/or reduce, prevent, or delay spoilage of the food product. The food additives may prevent development of unpleasant taste and/or smell, as well as changes in color, viscosity, density and solubility.
[00143] Further provided are methods of making and using the disclosed cannabinoid antioxidants. [00144] As shown in FIG. 1, radical terminators are antioxidants that prevent lipid oxidation by terminating the free radical chains and stopping autoxidation. FIG. 2 shows several synthetic radical terminators: (a) BHA; (b) BHT; (c) TBHQ; and gallates, such as (d) propyl gallate and (e) octyl gallate; certain types of vitamin E, such as (f) a-Tocopherol and (g) Trolox; and (h) olivetol.
Olivetol is used in various methods of producing synthetic analogs of THC. A common structural element in synthetic radical terminators is presence of one or more phenols. The antioxidant properties of these compounds are provided in Table 1.
Table 1: IC50 of Olivetol and commonly used antioxidant compounds
[00145] Olivetol is a structural precursor in the synthesis of the cannabinoid cannabigerol (CBG). Olivetol and cannabigerol share the 1,3-benzenediols and the pentyl sidechain; cannabigerol has a polypropyl moiety at the 2-position:
[00146] The present inventors have determined that, surprisingly, CBG has better antioxidant capacity than either the natural preservative Rosemary extract or vitamin E family antioxidants. A central concern in the use of cannabinoids in food products is that at effective concentrations of the cannabinoid, the cannabinoids could have adverse effects on the food products. This concern has, to date, discouraged the use of purified cannabinoids as food additives or in food products, particularly those that typically are expected to have a shelf-life of a week or more and which may be mass- produced. Given, however, the demonstration herein that CBG is a potent antioxidant, CBG and other cannabinoids may find novel utility as antioxidants in food additives and food products. CBG and other cannabinoids may be especially useful in edible oils, e.g. for use in making salad dressings, bouillons, sauces, and marinades.
[00147] In various embodiments, the food additives and food products of the disclosure are edible oils. Edible oils are composed primarily of fatty acids, which may be degraded by oxidation. Food product quality must be maintained. Thus, edible oils may in some cases be stabilized with antioxidants disclosed herein. The edible oils of this disclosure include without limitation, coconut oil, palm oil, palm kernel oil, olive oil, peanut oil, canola oil, soybean oil, cottonseed oil, com oil, linseed oil, safflower oil, sunflower oil, avocado oil, mustard oil, rice brain oil, almond oil, apricot kernel oil, basil oil, brazil nut oil, cashew oil, cottonseed oil, grapeseed oil, hazelnut oil, macadamia oil, rapeseed oil, walnut oil, and sesame oil. Further food products disclosed herein include butter, cocoa butter, tallow, margarine, and cream. Each of these and other food products may comprise a cannabinoid or cannabinoid derivative (e.g, CBG or a derivative thereof), optionally in the concentration ranges disclosed herein.
[00148] The food additives disclosed herein may also be used in formulation of honey, milk, soda, juice, yogurt, cream, almond milk, coconut milk, or nut milk (e.g. almond milk). In further embodiments, the food product is a nutritional supplement, nutrient, or pharmaceutical food preparation.
[00149] In some embodiments, the food additive is used to make a solid food product. The food additive may be provided in or as sugar, flour, or various spices to provide an antioxidant effect in storage and in use in a finished food product. The food additives of the disclosure are particularly useful in food products having a long shelf life and/or food products capable of being made with oils. Examples include potato chips, com chips, cookies, brownies, blondies, crackers, and pasta. The food additives may be injected into or used to coat meats, fish, or vegetables. For example, the food additive may be an edible wax, e.g. used to coat apples, bananas, or other fruit.
[00150] In some embodiments, the food additive is a solution, oil-in-water suspension, water-in-oil suspension, or a solid. The food additive may comprise a fat or an oil, or the food additive may comprise an aqueous solution or solvent. In various embodiments, the food additive may be used in beverages (e.g., soft drinks, milk and other dairy drinks, and diet drinks), baked goods, puddings, dairy products, confections, snack foods, or frozen confections or novelties (e.g., ice cream, milk shakes), prepared frozen meals, protein shakes, candy, snack products (e.g, chips), soups, spreads, sauces, salad dressings, bouillons, prepared meat products, cheese, yogurt, gravy, and food ingredients (e.g, flour). In some embodiments, the food product is a sauce, finished oil, condiment, or marinade.
[00151] The food additive or food product may comprise other antioxidants, or may be free of other antioxidants. Both synthetic and natural product antioxidants are available. Natural product antioxidants include hydroxytyrosol tyrosol, caffeic acid, ferulic acid, alkannin, shikonin, camosic acid, a-tocopherol, EDTA, gallic acid, catechin, quercetin, myricetin, genistein, sesamol, oleuropein, the oryzanols, the tocols, b-carotene, lycopene, bixin, and plant extracts (e.g, rosemary) containing these compounds.
[00152] As disclosed herein, certain cannabinoids and cannabinoid derivatives (e.g, CBG) have superior activity against peroxyl radicals as compared to Rosemary extract and the tocopherols. Further, certain cannabinoids and cannabinoid derivatives may have superior thermal stability compared to commonly used synthetic and/or natural antioxidants. In some embodiments, the food additive or food product demonstrates antioxidant property that preserve the food product for a least one year, or at least two years, at a predetermined temperature, e.g, between 25°C and 30 °C. The food additive or food product may be stable to heat processing and/or may protect the food product from thermal degradation.
[00153] The food additives and food products disclosed herein comprise a cannabinoid or derivative thereof. As used herein, the term “cannabinoid or cannabinoid derivative” refers to compounds including or not limited to, cannabichromene (CBC) type (e.g., cannabichromenic acid), cannabidiol (CBD) type (e.g., cannabidiolic acid), A 9 -trans-tetrahydrocannabinol (D 9 -THC) type
(e.g., A 9 -tetrahydrocannabinolic acid), A 8 -trans-tetrahydrocannabinol (D 8 -THC) type, cannabicyclol
(CBL) type, cannabielsoin (CBE) type, cannabinol (CBN) type, cannabinodiol (CBND) type, cannabitriol (CBT) type, derivatives of any of the foregoing, and others as listed in Elsohly et al.,
Life Sci. 78:539-48 (2005); cannabichromenic acid (CBCA), cannabichromene (CBC), cannabichromevarinic acid (CBCVA), cannabichromevarin (CBCV), CBDA, cannabidiol (CBD), cannabidiol monomethylether (CBDM), cannabidiol-C4 (CBD-C4), cannabidivarinic acid
(CBDVA), cannabidivarin (CBDV), cannabidiorcol (CBD-Ci), D 9 -tetrahydrocannabinolic acid A
(THCA-A), D 9 -tetrahydrocannabinolic acid B (THCA-B), D 9 -tetrahydrocannabinol (A 9 THC), D 9
-tetrahydrocannabinolic acid-C4 (THCA-C4), D 9 -tetrahydrocannabinol-C4 (THC-C4), D 9 - tetrahydrocannabivarinic acid (THCVA), D 9 -tetrahydrocannabivarin (THCV), D 9 - tetrahydrocannabiorcolic acid (THCA-Ci), D 9 -tetrahydrocannabiorcol (THC-Ci), D 7 -cis-iso- tetrahydrocannabivarin, D 8 -tetrahydrocannabinolic acid (D 8 -THCA), D 8 -tetrahydrocannabinol
(D 8 -THC), tetrahydrocannabiphorol (THCP), cannabicyclolic acid (CBLA), cannabicyclol (CBL), cannabicyclovarin (CBLV), cannabielsoic acid A (CBEA-A), cannabielsoic acid B (CBEA-B), cannabielsoin (CBE), cannabielsoinic acid, cannabicitranic acid, cannabinolic acid (CBNA), cannabinol (CBN), cannabinol methylether (CBNM), cannabinol-C4, (CBN-C4), cannabivarin
(CBV), cannabinol-C2 (CNB-C2), cannabiorcol (CBN-Ci), cannabinodiol (CBND), cannabinodivarin (CBVD), cannabitriol (CBT), 10-ethyoxy-9-hydroxy-delta-6a- tetrahydrocannabinol, 8,9-dihydroxyl-delta-6a-tetrahydrocannabinol, cannabitriolvarin (CBTV), dehydrocannabifuran (DCBF), cannabifuran (CBF), cannabichromanon (CBCN), cannabicitran (CBT), 10-oxo-delta-6a-tetrahydrocannabinol (OTHC), delta-9-cis-tetrahydrocannabinol (cis-THC), 3,4,5,6-tetrahydro-7-hydroxy-alpha-alpha-2-trimethyl-9-n-pro pyl-2,6-methano-2H-l-benzoxocin-5- methanol (OH-iso-HHCV), cannabiripsol (CBR), trihydroxy-delta-9-tetrahydrocannabinol (triOH- THC), CBGA-hydrocinnamic acid (3-[(2E)-3,7-dimethylocta-2,6-dien-l-yl]-2,4-dihydroxy-6-(2- phenylethyl)benzoic acid), CBG-hydrocinnamic acid (2-[(2E)-3,7-dimethylocta-2,6-dien-l-yl]-5-(2- phenylethyl)benzene-l,3-diol), CBDA-hydrocinnamic acid (2,4-dihydroxy-3-[3-methyl-6-(prop-l- en-2-yl)cyclohex-2-en-l-yl]-6-(2-phenylethyl)benzoic acid), CBD-hydrocinnamic acid (2-[3- methyl-6-(prop- 1 -en-2-yl)cyclohex-2-en- 1 -yl]-5-(2-phenylethyl)benzene- 1 ,3 -diol), THC A- hydrocinnamic acid (1 -hydroxy-6, 6, 9-trimethyl-3-(2-phenylethyl)-6H,6aH,7H,8H,10aH- benzo[c]isochromene-2-carboxylic acid), THC-hydrocinnamic acid (6,6,9-trimethyl-3-(2- phenylethyl)-6H,6aH,7H,8H,10aH-benzo[c]isochromen-l-ol, perrottetinene), and derivatives of any of the foregoing.
[00154] A cannabinoid derivative may also refer to a compound lacking one or more chemical moieties found in naturally-occurring cannabinoids, yet retains the core structural features (e.g., cyclic core) of a naturally-occurring cannabinoid. Such chemical moieties may include, but are not limited to, methyl, alkyl, alkenyl, methoxy, alkoxy, acetyl, carboxyl, carbonyl, oxo, ester, hydroxyl, and the like.
[00155] In some embodiments, the present disclosure provides a food additive comprising between about 1 and about 400 ppm of a cannabinoid or cannabinoid derivative. In some embodiments, the present disclosure provides a food additive comprising between about 1 and about 150 ppm of a cannabinoid or cannabinoid derivative. The cannabinoid or cannabinoid derivative may be selected as one not scheduled on the UN Convention of Psychotropic Substances.
[00156] In some embodiments, the cannabinoid is cannabigerol (CBG) or a derivative thereof. In some embodiments, the cannabinoid is cannabigerol (CBG). In some embodiments, the food product comprises pure CBG. As used herein, “pure” CBG refers to CBG that is > 95% w/w of total cannabinoid in the composition ( e.g ., food additive or food product). Pure CBG may be derived from extraction from plants, chemical synthesis, or fermentation. Pure CBG is distinguished from sources of CBG where the CBG is mixed with other cannabinoids. Purity may be evaluated using by LC methods, including LC-MS, e.g., using a weight purity method. Assays for purity include high performance liquid chromatography (e.g. Shimadzu LC20) using validated methods and standards. [00157] In some embodiments, the food additive or the food product is substantially free of cannabinoids or derivatives thereof, other than CBG. In some embodiments, the food additive or the food product comprises no detectable amount of tetrahydrocannabinol (THC). In some embodiments, the food additive or the food product comprises no detectable amount of cannabidiol (CBD). A “detectable amount” refers to an amount detectable using standard analytical equipment used in the food sciences, e.g. less than about 1 ppm, less than about 100 ppb, less than about 10 ppb, or less than about 1 ppb.
[00158] In some embodiments, the food additive or food product comprises a low dose of the cannabinoid or cannabinoid derivative, e.g. about an antioxidant effective amount, or about 2, 3, 4,
5, 6, 7, 8, 9, or 10 times the antioxidant effective amount. As used herein, the term “antioxidant effective amount” refers to reduce, prevent, or delay spoilage of a food product by oxidation. A food additive may comprise an antioxidant effective amount, or an amount sufficient to yield an antioxidant effective amount when the food additive is diluted into a selected food product. Thus, the food additive may comprise at least 10 times, at least 20 times the antioxidant effective amount, or more; or may comprise 1-3 times, 1-5 times, 6-10 times, or 10-20 times the antioxidant effective amount. The antioxidant effective amount may be determined using methods disclosed herein. E.g ., for CBG, the antioxidant effective amount may be at least about 10 ppm, at least about 15 ppm, at least about 20 ppm, at least about 25 ppm, at least about 30 ppm, at least about 35 ppm, about 40 ppm, at least about 45 ppm, at least about 50 ppm, at least about 55 ppm, at least about 60 ppm, at least about 65 ppm, about 70 ppm, at least about 75 ppm, at least about 80 ppm, at least about 85 ppm, at least about 90 ppm, at least about 95 ppm, at least about 100 pm, at least about 105 ppm, at least about 110 ppm, at least about 115 ppm, at least about 120 ppm, at least about 125 ppm, at least about 130 ppm, at least about 135 ppm, about 140 ppm, at least about 145 ppm, at least about 150 ppm, at least about 155 ppm, at least about 160 ppm, at least about 165 ppm, about 170 ppm, at least about 175 ppm, at least about 180 ppm, at least about 185 ppm, at least about 190 ppm, at least about 195 ppm, at least about 200 pm, at least about 205 ppm, at least about 210 ppm, at least about 215 ppm, at least about 220 ppm, at least about 225 ppm, at least about 230 ppm, at least about 235 ppm, about 240 ppm, at least about 245 ppm, at least about 250 ppm, at least about 255 ppm, at least about 260 ppm, at least about 265 ppm, about 270 ppm, at least about 275 ppm, at least about 280 ppm, at least about 285 ppm, at least about 290 ppm, at least about 295 ppm, or at least about 300 ppm.
[00159] Preferably, for CBG, the antioxidant effective amount may be at least about 10 ppm, at least about 20 ppm, at least about 30 ppm, at least about 40 ppm, at least about 50 ppm, at least about 60 ppm, or about 70 ppm.
[00160] The antioxidant effective amount may vary based on other ingredients of the food product and may be determined empirically. Illustrative methods for determining an antioxidant effective amount are provided in the examples that follow, and may include, for example, sensory panel testing and chemical analysis. Methods of chemical analysis of oxidation are provided in Oxidation in Foods and Beverages and Antioxidant Applications. ISBN 978-1-84569-648-1 (2010), which is incorporated herein in its entirety — in particular, Chapter 6 concerning edible oils.
[00161] The disclosure provides food additives having higher concentrations of the cannabinoid, intended for use in preparing food products by mixture with other edible ingredients. Thus, in some embodiments, the food additive comprises up to or at most about 400 ppm, up to or at most about 500 ppm, up to or at most about 600 ppm, up to or at most about 700 ppm, up to or at most about 800 ppm, up to or at most about 900 ppm, up to or at most about 1,000 ppm, up to or at most about 2,000 ppm, up to or at most about 3,000 ppm, up to or at most about 4,000 ppm, up to or at most about 5,000 ppm, up to or at most about 6,000 ppm, up to or at most about 7,000 ppm, or up to or at most about 8,000 ppm of the cannabinoid. Food products may be prepared such that they contain 1- 10% weight by weight (w/w), 10-20% w/w, or 20-30% w/w of the food additive, or any percentage therebetween, e.g. 1%, 2%, 3%, 4%, 5%, etc. In some embodiments, the food product comprises less than 1% w/w of the food additive, where the food additive includes a high concentration of the cannabinoid, e.g. >100 times the aniti oxidant effective amount.
EXAMPLES
Example 1 Chemical Testing of Antioxidant Properties of Cannabigerol
[00162] The antioxidant properties of CBG were tested using two assays: The Trolox Equivalent Antioxidant Capacity (TEAC) assay measures the ability of antioxidants to scavenge the stable radical cation ABTS+, a blue-green chromophore with maximum absorption at 734 nm that decreases in its intensity in the presence of antioxidants. The Oxygen Radical Absorbance Capacity (ORAC) assay measures scavenging activity against oxygen radicals that are known to be involved in the pathogenesis of aging and common diseases. Naguib et al. JNutr Sci Vitaminol 49(4):217-20 (2003).
[00163] The TEAC and ORAC assays are standard measures of antioxidant capacity. CBG exhibited remarkable activity in both (Table 2).
Table 2: CBG antioxidant properties
TE = Trolox equivalent
[00164] CBG exhibited better antioxidant capacity in the TEAC assay than Rosemary extract
(Table 3)
Table 3: CBG v. Rosemary Extract in TEAC Assay [00165] Surprisingly, in the ORAC assay against peroxyl radicals, CBG exhibited 2-3 fold more potent antioxidant activity than the vitamin E family antioxidants (Table 4). Tocopherol formulations are commonly known as Vitamin E.
Table 4: CBG v. Vitamin E in ORAC against peroxyl radicals assay
Example 2 Sensory Panel Testing of Salad Dressing Containing Cannabigerol
[00166] Sensory panel testing provides a subjective analysis of samples that have undergone an accelerated aging protocol. Sensory analysis was conducted on a salad dressing formulation containing 17% w/w of a food additive (canola oil) containing up to 400 ppm CBG. CBG was first added to canola oil to form a stock solution of 0.42% w/v CBG (approximately 4,000 ppm), from which serial dilution of the CBG in canola oil were prepared. The salad dressing was then made by mixing sugar in white vinegar with various flavors, colors and stabilizers, and then mixing in the CBG-containing canola oil to reach the formulation in Table 5.
Table 5
[00167] The resulting salad dressings had between about 10 ppm and 70 ppm of CBG (Table 6). Table 6
[00168] The salad dressing samples were subjected to an accelerated aging process that simulates conditions known to lead to oxidation and rancidity in oils. Samples were stored at 40°C with light exposure of 10,000 lux in bottles with 100 cm 3 of headspace for 15 days. Taste testing was performed by four food scientists. Results were reported using a 10-point Likert scale.
[00169] The sensory results indicate that CBG is protective against oxidation, with Likert scores decreasing in a dose-dependent manner with increasing amounts of CBG (FIG. 3).
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