US010722490B2

( 12 ) United States Patent (10 ) Patent No.: US 10,722,490 B2 Levy (45 ) Date of Patent: * Jul. 28 , 2020

( 54 ) WATER SOLUBLE COMPOSITIONS (56 ) References Cited COMPRISING PURIFIED CANNABINOIDS U.S. PATENT DOCUMENTS ( 71) Applicant: CANOPY GROWTH 4,837,228 A 6/1989 Elsohly et al . CORPORATION , Smiths Falls (CA ) 5,891,469 A 4/1999 Amselem (72 ) Inventor: Kurt Aron Levy , Superior, CO (US ) 6,982,282 B2 1/2006 Lambert et al . 7,923,026 B2 4/2011 Moschwitzer ( 73 ) Assignee: Canopy Growth Corporation , Ontario 8,790,719 B2 7/2014 Parolaro et al . (CA ) 2003/0101902 Al 6/2003 Reitnauer et al . 2006/0257463 Al 11/2006 Elsohly et al . ( * ) Notice : Subject to any disclaimer, the term of this 2008/0193725 Al 8/2008 Saint -Romain 2009/0098192 A1 4/2009 Fulsz patent is extended or adjusted under 35 2009/0133704 A1 5/2009 Strickland et al. U.S.C. 154 ( b ) by 0 days. 2010/0298579 Al 11/2010 Steup et al. 2011/0052694 Al 3/2011 Stinchcomb et al. This patent is subject to a terminal dis 2012/0004251 A1 1/2012 Whalley et al. claimer . 2013/0059018 A1 3/2013 Parolaro et al. 2013/0276779 A1 10/2013 Hale et al. ( 21 ) Appl. No .: 16 /700,678 2014/0100269 A1 4/2014 Goskonda et al. (22 ) Filed : Dec. 2 , 2019 2014/0221469 A1 8/2014 Ross et al . 2014/0243405 Al 8/2014 Whalley et al. (65 ) Prior Publication Data 2014/0271940 A1 9/2014 Wurzer et al. 2014/0356420 A1 12/2014 Huang US 2020/0121637 A1 Apr. 23 , 2020 2015/0064250 A1 3/2015 Ghebre - Sellassie et al. 2015/0126595 Al 5/2015 Smith et al . 2015/0258040 Al 9/2015 Lynch et al. 2015/0297556 A1 10/2015 Smith Related U.S. Application Data 2016/0029658 A1 2/2016 Segawa et al . (63 ) 2016/0081976 A1 3/2016 Bromley Continuation of application No. 16 /328,833 , filed as 2016/0250270 A1 9/2016 Cooper et al . application No. PCT/ US2017 /049219 on Aug. 29 , 2016/0256395 A1 9/2016 De Vries et al. 2017 , now Pat. No. 10,568,865 . 2016/0279073 A1 9/2016 Donsky et al. 2017/0049754 A1 2/2017 Diederich et al. 2017/0266153 Al 9/2017 Levy et al. (60 ) Provisional application No. 62 / 380,954 , filed on Aug. 2019/0030101 A1 1/2019 Cooper et al . 29, 2016 . 2019/0090527 Al 3/2019 Levy 2019/0183853 A1 6/2019 Levy (51 ) Int. Cl. 2019/0388384 Al 12/2019 Segal et al . A61K 31/335 ( 2006.01 ) A61K 31/355 (2006.01 ) FOREIGN PATENT DOCUMENTS A61K 31353 (2006.01 ) A61K 9/107 CA 2684562 10/2008 ( 2006.01 ) CN 100482657 7/2005 A61K 31/05 (2006.01 ) CN 102869356 1/2013 A61K 36/185 (2006.01 ) CN 103826621 5/2014 A61K 47/22 ( 2006.01 ) GB 2495118 4/2013 A61K 31/01 WO WO 2008/024408 2/2008 (2006.01 ) WO WO 2011/135591 11/2011 A6IK 31/065 ( 2006.01 ) WO WO 2014/100231 6/2014 A61K 31/192 ( 2006.01 ) WO WO 2014/159688 10/2014 A61K 31/122 WO WO 2015/068052 5/2015 ( 2006.01 ) WO WO 2015/200049 12/2015 A61K 31/045 (2006.01 ) WO WO 2016/109624 7/2016 A61K 31/015 ( 2006.01) WO WO 2018/011808 1/2018 A61K 9/08 (2006.01 ) A61K 31352 (2006.01 ) OTHER PUBLICATIONS A61K 45/06 ( 2006.01 ) U.S. Appl . No. 16 /456,078 , filed , Jun . 2019 , Reid et al. (52 ) U.S. CI. (Continued ) CPC A61K 31/353 (2013.01 ) ; A61K 9/08 ( 2013.01 ) ; A61K 9/107 ( 2013.01) ; A61K 31/01 Primary Examiner — Raymond J Henley, III (2013.01 ) ; A61K 31/015 ( 2013.01) ; A61K (74 ) Attorney, Agent, or Firm Sheridan Ross P.C. 31/045 (2013.01 ) ; A61K 31/05 ( 2013.01 ) ; (57 ) ABSTRACT A61K 31/065 ( 2013.01) ; A61K 31/122 This disclosures relates to new compositions and methods ( 2013.01 ) ; A61K 31/192 (2013.01 ) ; A6IK for making cannabinoid formulations. In one embodiment, 31/352 (2013.01 ) ; A61K 31/355 (2013.01 ) ; this disclosure provides water soluble compositions com A61K 36/185 ( 2013.01 ) ; A61K 45/06 prising a first purified cannabinoid and Vitamin E TPGS. In ( 2013.01 ) ; A61K 47/22 ( 2013.01) one embodiment, the disclosure herein comprises a method ( 58 ) Field of Classification Search of making powders comprising heatings material to a first CPC A61K 31/335 ; A61K 31/355 temperature and a second temperature . USPC 514/454 , 458 See application file for complete search history . 17 Claims, No Drawings US 10,722,490 B2 Page 2

( 56 ) References Cited Mepartland et al ., “ Side Effects of Pharmaceuticals Not Elicited by the Comparable Herbal Medicines: The Case of Tetrahydrocannabi nol and Marijuana, ” Alternative Therapies in Health and Medicine , OTHER PUBLICATIONS vol. 5, No. 4 , Jul . 1999, pp . 57-62 . Ansel et al. , “ Pharmaceutical Dosage Forms and Drug Delivery Mosely , “ Ebbu Announces Groundbreaking Production Scale Puri Systems, 7th Edition ,” Lippincott , Williams, & Wilkins, 1999 , pp . fication Process , " Business Wire , Jun . 13 , 2016 , retrieved from 48-53 . www.businesswire.com/news/home/20160613006490/en/Ebbu Chen , “ Some of the Parts: Is Marijuana's ‘ Entourage Effect ' Sci Announces -Groundbreaking - Production - Scale - Purification entifically Valid ?” Scientific American , Apr. 20 , 2017 , retrieved Process, 2 pages. from www.scientificamerican.com/article/some-of-the-parts Omar et al. , “ Optimisation and characterisation ofmarihuana extracts is -marijuana - rsquo - s - ldquo -entourage -effect - rdquo - scientifically obtained by supercritical fluid extraction and focused ultrasound valid , 3 pages . extraction and retention time locking GC -MS , ” Journal of Separate Haibo et al. , “ Research Progress on Chemical ingredient and Science, vol. 36 , 2013 , pp . 1397-1404 . Pharmacological activity of Fructus Cannabis ,” Chinese Journalof Ross et al. , “ The Volatile Oil Composition of Fresh and Air -Dried Ethnomedicine and Ethnophamacy, vol. 19, No. 8 , 2010 , pp . 56-57 . Buds of Cannabis sativa ," Journal of Natural Products , vol. 59 , No. Izzo et al. , “ Inhibitory effect of cannabichromene, a major non 1, Jan. 1996 , pp . 49-51. psychotropic cannabinoid extracted from Cannabis sativa , on inflam Russo et al. , “ Taming THC : potential cannabis synergy and phytocan mation - induced hypermotility in mice ,” British Journal of Pharma nabinoid -terpenoid entourage effects, ” British Journal of Pharma cology , vol. 166 , 2012, pp . 1444-1460 . cology, vol. 163 , 2011, pp . 1344-1364 . Klauke et al. , “ The cannabinoid CB2 receptor - selective phytocan Tomic et al. , “ Antihyperalgesic and Antiedematous Activities of nabinoid beta - cryophyllene exerts analgesic effects in mouse mod Bisabolol -Oxides -Rich Matricaria Oil in a Rat Model of Inflam els of inflammatory and neuropathic pain , " European mation , ” Phytotherapy Research , vol. 28, 2014 , pp . 759-766 . Neuropsychopharmacology, vol . 24 , 2014. pp . 608-620 . Wirth et al. , “ Anti - Inflammatory Properties of Cannabichromene, " Maione et al. , “Non -psychoactive cannabinoids modulate the descend Life Sciences, vol. 26 , No. 23 , 1980 , 5 pages . ing pathway of antinociception in anaesthetized rats through several Wright et al. , " Cannabinoid CB2 receptors in the gastrointestinal mechanisms of action ,” British Journal of Pharmacology, vol. 162, tract: a regulatory system in states of inflammation ,” British Journal 2011, pp . 584-596 . of Pharmacology, vol. 153, 2008 , pp . 263-270 . Marriot et al. , " Pharmaceutical Compounding and Dispensing , 2nd International Search Report and Written Opinion for International Edition ,” Pharmaceutical Press, 2010 , 305 pages. (PCT ) Application No. PCT/ US2017 /049219 , dated Nov. 3 , 2017 , 7 Mcpartland et al. , " Cannabis and Cannabis Extracts: Greater than pages . the Sum of Their Parts ?,” The Haworth Press, Inc., 2001, pp . Extended European Search Report for European Patent Application 103-132 . No. 17847412.8 , dated May 26 , 2020 , 7 pages . US 10,722,490 B2 1 2 WATER SOLUBLE COMPOSITIONS embodiment, the formulations disclosed herein are used for COMPRISING PURIFIED CANNABINOIDS creating other new formulations . In one embodiment, the formulations disclosed herein are soluble in other liquids, CROSS -REFERENCE TO RELATED e.g. , aqueous liquids such as juices , soft drinks , wine, APPLICATIONS 5 cocktails , medicinal preations, coffee , tea , etc. This application is a continuation of U.S. patent applica Disclosed herein are methods of making formulations tion Ser . No. 16 /328,833 filed Feb. 27 , 2019 , now U.S. Pat. with increased permeability into the bloodstream . Also No. 10,568,865 , which is a national stage application under disclosed herein are Cannabis formulations, which provide 35 U.S.C.371 and claims the benefit of PCT Application No. increased bioavailability of cannabinoids . PCT/ US2017 /049219 having an international filing date of 10 Disclosed herein is a new composition comprising a first Aug. 29 , 2017 , which designated the United States, which purified cannabinoid and Vitamin E TPGS . PCT application claimed the benefit of U.S. Provisional As used herein , the term “ purified ” means extracted , Patent Application Ser. No. 62 /380,954 , filed on Aug. 29 , isolated , and / or separated from other compounds, formula 2016 , the entire disclosures of each of which are incorpo tions , compositions, matter, and /or mass . In one embodi rated herein by reference . 15 ment, the term “ purified ” refers to a cannabinoid that is separated from the plantmatter from which it was derived . TECHNICAL FIELD In one embodiment, the term “ purified ” refers to a can nabinoid ( a “ purified cannabinoid ” ) that is separated from This disclosure relates to the cannabis industry . In par other cannabinoids that were present in the plant matter from ticular, this disclosure relates to water soluble cannabinoid 20 which it was derived . In one embodiment, the term “ puri formulations, including methods for creating said water fied ” refers to a cannabinoid (a “ purified cannabinoid ”) that soluble cannabinoid formulations. is separated from terpenes that were present in the plant matter from which it was derived . In one embodiment, the BACKGROUND term “ purified ” refers to a cannabinoid ( a “ purified cannabi The word “ Cannabis ” refers to a genus of flowering 25 noid " ) that is separated from secondary compounds that plants . Plants of genus Cannabis include several species , were present in the plantmatter from which it was derived . including Cannabis sativa , Cannabis indica , and Cannabis In one embodiment, the term “ purified ” refers to a cannabi ruderalis . There is a long history of cultivating plants of noid ( a “ purified cannabinoid ” ) that is separated from all genus Cannabis for hemp fibers, seeds and seed oils ,medici material that was present in the plant matter from which it nal purposes, and recreational activities . 30 was derived . According to some accounts , Cannabis is composed of at In one embodiment, the term “ purified ” refers to a terpene least 483 known chemical compounds, which include can (a “ purified terpene” ) that is separated from other cannabi nabinoids , terpenoids, flavonoids, nitrogenous compounds, noids that were present in the plant matter from which it was amino acids, proteins, glycoproteins, enzymes , sugars and derived . In one embodiment, the term “ purified ” refers to a related compounds, hydrocarbons, alcohol , aldehydes , 35 terpene (a “ purified terpene" ) that is separated from terpenes ketones, acids, fatty acids, esters, lactones , steroids, ter that were present in the plant matter from which it was penes, non -cannabinoid phenols , vitamins, and pigments . derived . In one embodiment, the term “ purified ” refers to a Cannabinoids are of particular interest for research and terpene (a “ purified terpene ” ) that is separated from second commercialization . Most extractions of Cannabis plant mat ary compounds that were present in the plant matter from ter aim to extract cannabinoids, particularly tetrahydrocan- 40 which it was derived . In one embodiment, the term “ puri nabinol ( THC ). THC is useful for relieving pain , treating fied ” refers to a terpene (a “ purified terpene” ) that is sepa glaucoma, and relieving nausea. THC is also gaining rated from all material that was present in the plant matter immense popularity as a recreational drug substance. Usu from which it was derived . ally , cannabinoids are extracted from the Cannabis plant as part of a crude mixture , combined with other chemical Within the context of this disclosure , purified compounds compounds found in the Cannabis plant. 45 may be purposely formulated with other compounds at Current methods of administration cannabinoids fail to various levels of purity . For example , depending on the take full advantage of cannabinoid properties . For example , desired outcome, a particular cannabinoid and /or terpene burning plant matter and inhaling the vapor does not allow may be formulated with other molecules when it is 60-65 % for selection of certain cannabinoids for their certain desired pure , 65-70 % pure , 70-75 % pure , 75-80 % pure , 80-85 % benefit . One can choose a plant with certain known prop 50 pure , 85-90 % pure, 90-95 % pure , 95-99 % pure , 99-99.9 % erties , e.g., THC content, but there is still little to no control pure , 99.9 + % , or greater than 99 % pure . Provided that the over selecting individual cannabinoids . Inhaling smoke also ingredients used for purposeful formulation are purified leads to many harmful and toxic compounds introduced into prior to the said purposeful formulation , the act of subse the body. quently formulating them does render them not “ purified ” There exists a need for new cannabinoid formulations. In 55 within the context of an ingredient list. particular , there exists a need for water soluble cannabinoid As used herein , the term “ cannabinoid ” refers to a com formulations. Additionally , there exists a need for methods pound belonging to a class of secondary compounds com for producing aqueous cannabinoid formulations . Further monly found in plants of genus Cannabis . In one embodi more , there exists a need for making formulations with ment, the cannabinoid is found in a plant, e.g., a plant of increased permeability into the bloodstream . Also , there also 60 genus Cannabis, and is sometimes referred to as a phyto exists a need for Cannabis formulations which provide cannabinoid . In one embodiment, the cannabinoid is found increased bioavailability of cannabinoids . in a mammal, sometimes called a endocannabinoid . In one embodiment , the cannabinoid is made in a laboratory set DETAILED DESCRIPTION ting , sometimes called a synthetic cannabinoid . In one 65 embodiment , the cannabinoid acts upon a cellular receptor, Disclosed herein are new cannabinoid formulations , such as a G - coupled protein receptor (e.g. , a serotonin including water soluble cannabinoid formulations. In one receptor, a cannabinoid receptor, TRPV1, an opioid receptor, US 10,722,490 B2 3 4 etc. ) thereby causing a response on the brain or body . In one embodiment, the cannabinoid affects the activity of other compounds at one or more receptors by acting as an agonist , partial agonist, inverse agonist , antagonist , etc. OH In many cases, a cannabinoid can be identified because its 5 111111 chemical name will include the text string “ * cannabi * in the name . H Within the context of this application , where reference is made to a particular cannabinoid , each of the acid and / or decarboxylated forms are contemplated as both single mol 10 ecules and mixtures . Within the context of this disclosure , compositions com Examples of cannabinoids include , but are not limited to , prising THC are formulated with other compounds, thereby Cannabigerolic Acid (CBGA ) , Cannabigerolic Acid providing previously unavailable aqueous formulations . monomethylether ( CBGAM ) , Cannabigerol (CBG ), Can As used herein , the term “ THCA ” refers to tetrahydro nabigerol monomethylether (CBGM ), Cannabigerovarinic 15 cannabinolic acid and has the following structural formula : Acid (CBGVA ), Cannabigerovarin (CBGV ) , Cannabi chromenic Acid ( CBCA ) , Cannabichromene ( CBC ), Can nabichromevarinic Acid (CBCVA ), Cannabichromevarin ( CBCV ) , Cannabidiolic Acid ( CBDA ), Cannabidiol ( CBD ), 20 Cannabidiol monomethylether (CBDM ), Cannabidiol- C4 OH (CBD -C4 ) , Cannabidivarinic Acid (CBDVA ), Cannabidi H varin ( CBDV ), Cannabidiorcol ( CBD - C ), Tetrahydrocan OH nabinolic acid A ( THCA - A ) , Tetrahydrocannabinolic acid B H ( THCA - B ), Tetrahydrocannabinolic Acid ( THCA ), Tetrahy- 25 drocannabinol ( THC ) , Tetrahydrocannabinolic acid C4 ( THCA - C4 ) , Tetrahydrocannbinol C4 ( THC - C4 ), Tetrahy drocannabivarinic( THCV ), Tetrahydrocannabiorcolic acid ( THCVA ) , acidTetrahydrocannabivarin ( THCA -C ) , Tetra Decarboxylating THCA with heat , light , etc., forms THC , hydrocannabiorcol ( THC - C ) , A ' - cis -iso -tetrahydrocan- 30 D8Within- THC the , contextD9- THC of , thisand disclosure other potential , compositions cannabinoids compris. nabivarin , 18 - tetrahydrocannabinolic acid (A8 - THCA ), ing THCA are formulated with other compounds, thereby Cannabivarinodiolic (CBNDVA ), Cannabivarinodiol providing previously unavailable aqueous formulations . ( CBNDV ) , A8 -tetrahydrocannabinal ( A - THC ) , Aº- tetrahy As used herein , the term “ THCV ” refers to tetrahydro drocannabinol (1® - THC ) , Cannabicyclolic acid (CBLA ) , cannabivarin and has the following structural formula : Cannabicyclol (CBL ) , Cannabicyclovarin (CBLV ) , Canna- 35 bielsoic acid A (CBEA - A ), Cannabielsoic acid B (CBEA - B ) , Cannabielsoin (CBE ), Cannabivarinselsoin (CBEV ), Can nabivarinselsoinic Acid (CBEVA ), Cannabielsoic Acid (CBEA ), Cannabielvarinsoin (CBLV ) , Cannabielvarinsoinic OH Acid (CBLVA ) , Cannabinolic acid (CBNA ) , Cannabinol 40 1111H ( CBN ) , Cannabivarinic Acid (CBNVA ), Cannabinolmethy lether ( CBNM ) , Cannabinol- C4 (CBN -C4 ) , Cannabivarin ( CBV ) , Cannabino - C2( CBN -C2 ) , Cannabiorcol (CBN -C1 ) , H Cannabinodiol (CBND ), Cannabinodiolic Acid (CBNDA ) , Cannabinodivarin10 -Ethoxy - 9 -hydroxy -(A6a CBDV - tetrahydrocannabinol ) , Cannabitriol, 8,9(- CBT Dihy) , 45 droxy - Aba ( 104) -tetrahydrocannabinol (8,9 -Di - OH -CBT - C3) , Within the context of this disclosure , compositions com Cannabitriolvarin (CBTV ), Ethoxy -cannabitriolvarin prising THCV are formulated with other compounds , (CBTVE ) , Dehydrocannabifuran (DCBF ) , Cannbifuran thereby providing previously unavailable aqueous formula ( CBF ) , Cannabichromanon (CBCN ) , Cannabicitran (CBT ), 50 tions . 10 -Oxo - A8a ( 10a) -tetrahydrocannabinol (OTHC ) , Aº- cis -tet As used herein , the term “ THCVA ” refers to tetrahydro rahydrocannabinol ( cis - THC ), Cannabiripsol (CBR ), 3,4,5 , cannabivarinic acid and has the following structural for 6 -tetrahydro - 7 - hydroxy - alpha - alpha - 2 - trimethyl- 9 - n - pro mula : pyl- 2,6 -methano - 2H - 1 -benzoxocin - 5 -methanol (OH - iso HHCV ) , Trihydroxy - delta - 9 - tetrahydrocannabinol ( triOH- 55 THC ) , Yangonin , Epigallocatechin gallate , Dodeca -25,4E , 8Z ,10Z -tetraenoic acid isobutylamide , and Dodeca -2E ,4E dienoic acid isobutylamide. OH In one embodiment, the first purified cannabinoid is chosen from THC , D9- THC , D8 - THC , THCA , THCV, 60 ?? D8 - THCV, D9 - THCV , THCVA , CBD , CBDA , CBDV , H CBDVA , CBC , CBCA , CBCV, CBCVA , CBG , CBGA , CBGV, CBGVA , CBN , CBNA , CBNV , CBNVA , CBND , CBNDA , CBNDV , CBNDVA , CBE , CBEA , CBEV , CBEVA , CBL , CBLA , CBLV , or CBLVA . 65 Decarboxylating THCVA with heat, light, etc. , forms As used herein , the term “ THC ” refers to tetrahydrocan THCV , D8 - THCV , D9 - THCV , and other possible cannabi nabinol and has the following structural formula : noid derivatives . Within the context of this disclosure, US 10,722,490 B2 5 6 compositions comprising THCVA are formulated with other compounds , thereby providing previously unavailable aque CH3 ous formulations. As used herein , the term “ D8 - THC ” refers to delta - 8 OH tetrahydrocannabinol and has the following structural for 5 mula : CH3

CH3 10 CH3 Within the context of this disclosure, compositions com OH prising D9- THCV are formulated with other compounds , thereby providing previously unavailable aqueous formula tions . 15 As used herein , the term “ CBD ” refers to cannabidiol and H3C has the following structural formula : CH ;

Within the context of this disclosure, compositions com 20 prising D8 - THC are formulated with other compounds, OH thereby providing previously unavailable aqueous formula tions . As used herein , the term “ D8 - THCV ” refers to delta - 8 H tetrahydrocannabivarin and has the following structural for 25 mula : HO Within the context of this disclosure , compositions com prising CBD are formulated with other compounds, thereby CH3 30 providing previously unavailable aqueous formulations . As used herein , the term “ CBDA ” refers to cannabidiolic OH acid and has the following structural formula :

35 H3C OH ??3 S 11H OH Within the context of this disclosure , compositions com 40 H prising D8- THCV are formulated with other compounds, thereby providing previously unavailable aqueous formula HO tions . Decarboxylating CBDA with heat, light, etc., forms CBD As used herein , the term “ D9- THC ” refers to delta - 9- 45 and other possible cannabinoid derivatives . Within the con tetrahydrocannabinol and has the following structural for text of this disclosure, compositions comprising CBDA are mula : formulated with other compounds, thereby providing previ ously unavailable aqueous formulations. As used herein , the term “ CBDV ” refers to cannabidi CH3 50 varin and has the following structural formula :

OH

55 OH CH3 1111H CH3. CH3 H

Within the context of this disclosure , compositions com 60 HO prising D9 - THC are formulated with other compounds , Within the context of this disclosure , compositions com thereby providing previously unavailable aqueous formula prising CBDV are formulated with other compounds , tions . thereby providing previously unavailable aqueous formula As used herein , the term “ D9- THCV ” refers to delta - 9- 65 tions . tetrahydrocannabivarin and has the following structural for As used herein , the term “ CBDVA ” refers to cannabidi mula : varinic acid and has the following structural formula : US 10,722,490 B2 7 8

OH 5 OH OH H HO HO 10 Decarboxylating CBDVA with heat, light, etc., forms Decarboxylating CBCVA with heat, light, etc. , forms CBDV and other possible cannabinoid derivatives. Within CBCV and other possible cannabinoid derivatives. Within the context of this disclosure, compositions comprising the context of this disclosure, compositions comprising CBDVA are formulated with other compounds, thereby 15 CBCVA are formulated with other compounds, thereby providing previously unavailable aqueous formulations. providing previously unavailable aqueous formulations . As used herein , the term " CBC ” refers to cannabi As used herein , the term “ CBG ” refers to cannabigerol chromene and has the following structural formula : and has the following structural formula :

20 OH

25 wbgHO HO Within the context of this disclosure , compositions com prisingWithin CBC the arecontext formulated of this withdisclosure other,compounds compositions, thereby com 30 prising CBG are formulated with other compounds, thereby providing previously unavailable aqueous formulations . providing previously unavailable aqueous formulations. As used herein , the term “ CBCA ” refers to cannabi As used herein , the term “ CBGA” refers to cannabigerolic chromenic acid and has the following structural formula : acid and has the following structural formula : 35 OH

OH OH 40 HO HO Lou Decarboxylating CBCA with heat , light, etc., forms CBC Decarboxylating CBGA with heat , light, etc., forms CBG and other possible cannabinoid derivatives. Within the con 45 and other possible cannabinoid derivatives . Within the con text of this disclosure, compositions comprising CBCA are text of this disclosure , compositions comprising CBGA are formulated with other compounds, thereby providing previ formulated with other compounds, thereby providing previ ously unavailable aqueous formulations. ously unavailable aqueous formulations . As used herein , the term “ CBCV ” refers to cannabi 50 As used herein , the term “ CBGV” refers to cannabigero chromevarin and has the following structural formula : varin and has the following structural formula :

OH 55

HO HO 60 Within the context of this disclosure , compositions com Within the context of this disclosure , compositions com prising CBCV are formulated with other compounds, prising CBGV are formulated with other compounds, thereby providing previously unavailable aqueous formula thereby providing previously unavailable aqueous formula tions . 65 tions . As used herein , the term “ CBCVA ” refers to cannabi As used herein , the term “ CBGVA ” refers to cannabigero chromevarinic acid and has the following structural formula : varinic acid and has the following structural formula : US 10,722,490 B2 9 10

OH

?? OH 5

HO OH Decarboxylating CBGVA with heat , light, etc., forms CBGV and other possible cannabinoid derivatives. Within 10 the context of this disclosure , compositions comprising Decarboxylating CBNVA with heat, light, etc., forms CBGVA are formulated with other compounds, thereby CBNV and other possible cannabinoid derivatives. Within providing previously unavailable aqueous formulations. the context of this disclosure , compositions comprising As used herein , the term “ CBN ” refers to cannabinol and CBNVA are formulated with other compounds, thereby has the following structural formula : 15 providing previously unavailable aqueous formulations. As used herein , the term “ CBND ” refers to cannabinodiol and has the following structural formula :

OH 20

OH

? 25 Within the context of this disclosure , compositions com HO prising CBN are formulated with other compounds , thereby providing previously unavailable aqueous formulations . Within the context of this disclosure , compositions com As used herein , the term “ CBNA ” refers to cannabinolic 30 prising CBND are formulated with other compounds, acid and has the following structural formula : thereby providing previously unavailable aqueous formula tions . As used herein , the term “ CBNDA ” refers to cannabino diolic acid and has the following structural formula : 35 OH

OH OH 40 ?? ?? Decarboxylating CBNA with heat, light, etc. , forms CBN HO and other possible cannabinoid derivatives . Within the con 45 text of this disclosure , compositions comprising CBNA are Decarboxylating CBNDA with heat, light, etc., forms formulated with other compounds, thereby providing previ CBND and other possible cannabinoid derivatives. Within ously unavailable aqueous formulations . the context of this disclosure , compositions comprising As used herein , the term “ CBNV” or “ CBV ” refers to CBNDA are formulated with other compounds, thereby cannabivarin and has the following structural formula : 50 providing previously unavailable aqueous formulations. As used herein , the term “ CBNDV ” refers to cannabiva rinodiol and has the following structural formula :

OH 55

OH

60 Within the context of this disclosure , compositions com prising CBNV are formulated with other compounds, HO thereby providing previously unavailable aqueous formula Within the context of this disclosure, compositions com tions . 65 prising CBNDV are formulated with other compounds, As used herein , the term “ CBNVA ” refers to cannabivar thereby providing previously unavailable aqueous formula inic acid and has the following structural formula : tions . US 10,722,490 B2 11 12 As used herein , the term “ CBNDVA ” refers to cannabi As used herein , the term “ CBLVA ” refers to cannabiel varinodiolic acid and has the following structural formula : varinsoinic acid and has the following structural formula :

5 OH

OH

OH 10 H3C HO Decarboxylating CBLVA with heat , light, etc., forms CBLV and other possible cannabinoid derivatives. Within Decarboxylating CBNDVA with heat , light, etc., forms 15 the context of this disclosure , compositions comprising CBNDV and other possible cannabinoid derivatives. Within CBLVA are formulated with other compounds, thereby the context of this disclosure, compositions comprising providing previously unavailable aqueous formulations. CBNDVA are formulated with other compounds, thereby As used herein , the term “ CBE ” refers to cannabielsoin providing previously unavailable aqueous formulations . and has the following structural formula : As used herein , the term “ CBL ” refers to cannabicyclol 20 and has the following structural formula : OH OH Hii 25 Hintay H H3C 30 HO Within the context of this disclosure, compositions com Within the context of this disclosure, compositions com prising CBL are formulated with other compounds , thereby prising CBE are formulated with other compounds, thereby providing previously unavailable aqueous formulations. providing previously unavailable aqueous formulations . As used herein , the term “ CBLA ” refers to cannabicy- 35 As used herein , the term “ CBEA ” refers to cannabielsoic clolic acid and has the following structural formula : acid and has the following structural formula :

OH OH 40 HI Hi , H3C be 45 H Decarboxylating CBLA with heat , light, etc., forms CBL HO and other possible cannabinoid derivatives. Within the con text of this disclosure, compositions comprising CBLA are Decarboxylating CBEA with heat, light, etc., forms CBE formulated with other compounds, thereby providing previ- 50 and other possible cannabinoid derivatives. Within the con ously unavailable aqueous formulations . text of this disclosure, compositions comprising CBEA are As used herein , the term “ CBLV ” refers to cannabicyclo formulated with other compounds, thereby providing previ varin and has the following structural formula : ously unavailable aqueous formulations. As used herein , the term “ CBEV ” refers to cannabivar OH 55 inselsoin and has the following structural formula :

OH 60 HI H3C Hinn Within the context of this disclosure , compositions com H prising CBLV are formulated with other compounds, 65 thereby providing previously unavailable aqueous formula HO tions. US 10,722,490 B2 13 14 Within the context of this disclosure , compositions com embodiment, the percent is the amount of Vitamin E TPGS prising CBEV are formulated with other compounds, in a composition . In one embodiment, the percent mass is thereby providing previously unavailable aqueous formula calculated with the following formula : tions . mass of compound + total mass of samplex100 As used herein , the term “ CBEVA ” refers to cannabivar- 5 inselsoinic acid and has the following structural formula : For example : 5.0 THC + 100 g samplex100 = 5 % As used herein , the term " ratio ” refers to the relative OH amount of one or more compounds in relation to another 10 compound or compounds. In one embodiment, the ratio is in reference to the mass of one compound to another . In one embodiment, the ratio is in reference to the mass percent of Hin one compound another. In one embodi ent, the ratio is in H reference to the dry weight of one compound to another . In 15 one embodiment, the ratio is in reference to the volume of one compound to another. In one embodiment, the ratio is in HO reference to the molar mass of one compound to another. In one embodiment, the ratio is the amount of first Decarboxylating CBEVA with heat , light, etc., forms purified cannabinoid to the amount of Vitamin E TPGS. In CBEV and other possible cannabinoid derivatives . Within 20 one embodiment , the ratio is the amount of a first purified the context of this disclosure, compositions comprising cannabinoid and a second purified cannabinoid to the CBEVA are formulated with other compounds, thereby amount of Vitamin E TPGS. In one embodiment, the ratio is providing previously unavailable aqueous formulations. the amount of a first purified cannabinoid and a second As used herein , the term “ Vitamin E TPGS” refers to the purified cannabinoid to the amount of Vitamin E TPGS . esterification of Vitamin E succinate with polyethylene 25 In one embodiment, the ratio of the first purified cannabi glycol 1000 resulting in the following structural formula : noid to Vitamin E TPGS is about 1 : 1 to 1:10 .

H noi CH3 CH3 CH3 CH3 CH ; H3C CH3, CH3 ??? 40 where “ n ” is an integer. In one embodiment, the ratio of the first purified cannabi Within the context of this disclosure, Vitamin E TPGS is noid to Vitamin E TPGS is about 1 : 1 to 1 : 8 . formulated with a compound or compounds found in a plant In one embodiment, the ratio of the first purified cannabi of genus Cannabis to increase the solubility and bioavail noid to Vitamin E TPGS is about 1 : 1 to 1 : 6 . ability of poorly water soluble lipophilic compounds. 45 In one embodiment , the ratio of the first purified cannabi In one embodiment, the compositions disclosed herein noid to Vitamin E TPGS is about 1 : 1 to 1 : 4 . comprise a ratio of Vitamin E TPGS to the first purified In one embodiment, the ratio of the first purified cannabi cannabinoid of about 90:10 to about 70:30 by percentmass . noid to Vitamin E TPGS is about 1 : 1 to 1 : 2 . In one embodiment, the compositions disclosed herein In one embodiment, the compounds disclosed herein comprise a ratio of Vitamin E TPGS to the first purified 50 comprise a terpene. cannabinoid of about 85:15 to about 75:25 by percent mass . In one embodiment, the compounds disclosed herein In one embodiment, the compositions disclosed herein comprise a purified terpene . comprise a ratio of Vitamin E TPGS to the first purified Examples of terpenes within the context of this disclosure cannabinoid of about 82:18 to about 78:22 by percent mass . include: 7,8 - dihydro -alpha - ionone, 7,8 -dihydro -beta - ion In one embodiment, the compositions disclosed herein 55 one, Acetanisole , Acetic Acid , Acetyl Cedrene , Anethole , comprise a ratio of Vitamin E TPGS to the first purified Anisole , Benzaldehyde, Bergamotene (Alpha -cis - Bergamo cannabinoid of about 80:20 to about 70:30 by percent mass . tene ) ( Alpha -trans -Bergamotene ) , Bisabolol (Beta - Bisab In one embodiment, the compositions disclosed herein olol) , Alpha , Bisabolol, Borneol, Bornyl Acetate , Butanoic / comprise a ratio of Vitamin E TPGS to the first purified Butyric Acid , Cadinene ( Alpha - Cadinene ) (Gamma cannabinoid of about 90:10 to about 80:20 by percent mass . 60 Cadinene) , Cafestol, Caffeic acid , Camphene , Camphor, As used herein , the term “ percent mass” refers to the Capsaicin , Carene (Delta -3 -Carene ) , Carotene, Carvacrol, amount ofmatter of a compound expressed as a fraction of Dextro - Carvone, Laevo - Carvone, Caryophyllene (Beta 100. In one embodiment, the percent mass is expressed in Caryophyllene ), Caryophyllene oxide , Cedrene ( Alpha -Ce grams. In one embodiment, the percent mass is expressed in drene) (Beta - Cedrene ), Cedrene Epoxide ( Alpha - Cedrene ounces . In one embodiment , the percent mass is expressed in 65 Epoxide) , Cedrol, Cembrene , Chlorogenic Acid , Cinnamal moles. In one embodiment, the percentmass is the amount dehyde, Alpha -amyl - Cinnamaldehyde, Alpha -hexyl Cinna of a first purified cannabinoid in a composition . In one maldehyde, Cinnamic Acid , Cinnamyl Alcohol, Citronellal, US 10,722,490 B2 15 16 Citronellol, Cryptone, Curcumene (Alpha - Curcumene ) As used herein , the term " contained within ” refers to (Gamma - Curcumene ), Decanal, Dehydrovomifoliol, Diallyl molecules , e.g. cannabinoids and /or terpenes , that are Disulfide, Dihydroactinidiolide , Dimethyl Disulfide, sequestered inside a spherical shape formed by micelles and Eicosane/ Icosane, Elemene (Beta - Elemene ) , Estragole , reverse micelles. In one embodiment, a cannabinoid con Ethyl acetate , Ethyl Cinnamate , Ethyl maltol, Eucalyptol /1 , 5 tained within a micelle allows said cannabinoid to disperse 8 -Cineole , Eudesmol (Alpha - Eudesmol) (Beta -Eudesmol ) or dissolve within an aqueous formulation . (Gamma - Eudesmol) , Eugenol, Euphol, Farnesene, Farnesol, Disclosed herein , is a method of making an aqueous Fenchol (Beta - Fenchol) , Fenchone, Geraniol, Geranyl cannabinoid formulation comprising adding 0-3 % water, by acetate , Germacrenes , Germacrene B ,Guaia - 1 ( 10 ) ,11 -diene , mass percent, to a composition comprising a first purified Guaiacol, Guaiene ( Alpha -Guaiene ), Gurjunene ( Alpha 10 cannabinoid and Vitamin E TPGS . Gurjunene ), Herniarin , Hexanaldehyde, Hexanoic Acid , As used herein , the term “ aqueous cannabinoid formula Humulene (Alpha - Humulene ) (Beta - Humulene ) , Ionol tion ” refers to a solution wherein a first purified cannabinoid ( 3 -oxo -alpha - ionol) (Beta - Ionol) , Ionone (Alpha - Ionone ) and Vitamin E TPGS are dispersed throughout water and ( Beta - Ionone ) , Ipsdienol, Isoamyl Acetate , Isoamyl Alcohol, wherein the water acts as a solvent. In one embodiment, the Isoamyl Formate , Isoborneol , Isomyrcenol, Isopulegol , 15 aqueous cannabind formulation is made by methods dis Isovaleric Acid , Isoprene, Kahweol, Lavandulol, Limonene , closed herein . In one embodiment, the aqueous cannabinoid Gamma- Linolenic Acid , Linalool, Longifolene, Alpha- Lon formulation comprises a second purified cannabinoid . In one gipinene, Lycopene, Menthol, Methyl butyrate , 3 -Mercapto embodiment, the aqueous cannabinoid formulation com 2 -Methylpentanal , Mercaptan / Thiols , Beta -Mercaptoetha- 20 prises a third purified cannabinoid . In one embodiment, the nol, Mercaptoacetic Acid , Allyl Mercaptan , Benzyl aqueous cannabinoid formulation comprises a first purified Mercaptan , Butyl Mercaptan , Ethyl Mercaptan, Methyl terpene . In one embodiment, the aqueous cannabinoid for Mercaptan , Furfuryl Mercaptan , Ethylene Mercaptan , Pro mulation comprises a second purified terpene . pyl Mercaptan , Thenyl Mercaptan , Methyl Salicylate , Meth In one embodiment, water accounts for between 0-10 % of ylbutenol, Methyl- 2 -Methylvalerate , Methyl Thiobutyrate , 25 the mass percent of the aqueous cannabinoid formulation . Myrcene (Beta - Myrcene ), Gamma- Muurolene , Nepetalac In one embodiment, water accounts for between 0-5 % of tone , Nerol, Nerolidol, Neryl acetate , Nonanaldehyde , the mass percent of the aqueous cannabinoid formulation . Nonanoic Acid , Ocimene, Octanal , Octanoic Acid , P -Cy In one embodiment , water accounts for between 0-3 % of mene, Pentyl butyrate , Phellandrene, Phenylacetaldehyde , the mass percent of the aqueous cannabinoid formulation . Phenylethanethiol, Phenylacetic Acid , Phytol, Pinene, Beta- 30 In one embodiment, water accounts for between 0-1 % of Pinene , Propanethiol, Pristimerin , Pulegone , Quercetin , the mass percent of the aqueous cannabinoid formulation . Retinol, Rutin , Sabinene, Sabinene Hydrate , cis -Sabinene In one embodiment, the first purified cannabinoid is THC . Hydrate , trans- Sabinene Hydrate , Safranal, Alpha -Selinene , In one embodiment, the aqueous cannabinoid formula AlphaTaxadiene - Sinensal, Terpin , Beta hydrate -Sinensal , Terpineol, Beta ,- SitosterolTerpine- 4-01 , Squalene, Alpha- , 35 tions disclosed herein comprise 50 to 99.9 % THC by percent Terpinene, Gamma- Terpinene , Terpinolene, Thiophenol, mass . Thujone , Thymol , Alpha - Tocopherol, Tonka Undecanone , In one embodiment, the first purified cannabinoid is Undecanal , Valeraldehyde /Pentanal , Verdoxan , Alpha - Ylan THCA . gene, Umbelliferone , or Vanillin . In one embodiment, the aqueous cannabinoid formula Within the context of this disclosure , the term terpene 40 tions disclosed herein comprise 50 to 99.9 % THCA by includes the c - alpha ), B-( beta ), Y- (gamma ) , oxo-, isomers, percent mass . or any combinations thereof. In one embodiment, the first purified cannabinoid is In one embodiment , the purified terpene is chosen from THCV . Limonene, Nerolidol, Beta -Myrcene , Linalool, Alpha In one embodiment, the aqueous cannabinoid formula Caryophyllene , Beta -Caryophyllene , Alpha -Pinene , Beta- 45 tions disclosed herein comprise 50 to 99.9 % THCV by Pinene , Alpha - Bisabolol, Delta - 3 -Carene , Borneol, p -Cy percent mass . mene , Eucalyptol, Alpha -Humulene , Alpha - Terpineol, In one embodiment , the first purified cannabinoid is Terpinolene , Pulegone, Camphene , or Geraniol. THCVA . In one embodiment, the purified cannabinoid is contained In one embodiment, the aqueous cannabinoid formula within a micelle of Vitamin E TPGS . 50 tions disclosed herein comprise 50 to 99.9 % THCVA by As used herein , the term “ micelle ” refers to a collection percent mass . of molecules arranged alongside one another in a spherical In one embodiment, the first purified cannabinoid is CBC . form often having a pocket inside . In one embodiment, the In one embodiment, the aqueous cannabinoid formula micelle comprises a lipid molecule . In one embodiment, the tions disclosed herein comprise 50 to 99.9 % CBC by percent lipid molecule comprises both a hydrophobic and hydro- 55 mass. philic region . In one embodiment, the micelle is in a solvent. In one embodiment, the first purified cannabinoid is In one embodiment, the hydrophilic region is in contact with CBCA. surrounding solvent, sequestering the hydrophobic region in In one embodiment, the aqueous cannabinoid formula the micelle centre . In one embodiment, the micelle is in tions disclosed herein comprise 50 to 99.9 % CBCA by water and the polar group is on the outside and a hydro- 60 percent mass . phobic end sequesters inside the spherical shape . In one In one embodiment, the first purified cannabinoid is embodiment, the micelle is a reverse micelle , i.e., the CBCV. hydrophilic region of a molecule is surrounded by a non In one embodiment , the aqueous cannabinoid formula polar solvent resulting in a water in oil system . In one tions disclosed herein comprise 50 to 99.9 % CBCV by embodiment, the reverse micelle comprises hydrophobic 65 percent mass . groups extended away from the center while hydrophilic In one embodiment, the first purified cannabinoid is groups are sequestered inside the spherical shape. CBCVA . US 10,722,490 B2 17 18 In one embodiment, the aqueous cannabinoid formula nabinoid content is determined by chromatography , e.g. , tions disclosed herein comprise 50 to 99.9 % CBCVA by HPLC . In one embodiment, the total purified cannabinoid percent mass . content comprises terpenes . In one embodiment, the first purified cannabinoid is CBD . In one embodiment, the compositions disclosed herein In one embodiment, the aqueous cannabinoid formula- 5 comprise a ratio of Vitamin E TPGS to total purified tions disclosed herein comprise 50 to 99.9 % CBD by percent cannabinoid content of about 90:10 to about 70:30 by mass . mass . In one embodiment, the compositions disclosed herein In one embodiment, the first purified cannabinoid is comprise a ratio of Vitamin E TPGS to total purified CBDA . cannabinoid content of about 85:15 to about 75:25 by mass . In one embodiment, the aqueous cannabinoid formula 10 In one embodiment, the compositions disclosed herein tions disclosed herein comprise 50 to 99.9 % CBDA by comprise a ratio of Vitamin E TPGS to total purified percent mass . cannabinoid content of about 82:18 to about 78:22 by mass. In one embodiment, the first purified cannabinoid is In one embodiment, the compositions disclosed herein CBDV . comprise a ratio of Vitamin E TPGS to total purified In one embodiment, the aqueous cannabinoid formula 15 cannabinoid content of about 80:20 to about 70:30 by mass . tions disclosed herein comprise 50 to 99.9 % CBDV by In one embodiment, the compositions disclosed herein percent mass . comprise a ratio of Vitamin E TPGS to total purified In one embodiment, the first purified cannabinoid is cannabinoid content of about 90:10 to about 80:20 by mass . CBDVA . 20 In one embodiment, the ratio of the total purified can In one embodiment, the aqueous cannabinoid formula nabinoid content to Vitamin E TPGS is about 1 : 1 to 1:10 . tions disclosed herein comprise 50 to 99.9 % CBDVA by In one embodiment, the ratio of the total purified can percent mass . nabinoid content to Vitamin E TPGS is about 1 : 1 to 1 : 8 . In one embodiment, the first purified cannabinoid is CBG . In one embodiment, the ratio of the total purified can In one embodiment, the aqueous cannabinoid formula- 25 nabinoid content to Vitamin E TPGS is about 1 : 1 to 1 : 6 . tions disclosed herein comprise 50 to 99.9 % CBG by percent In one embodiment, the ratio of the total purified can mass . nabinoid content to Vitamin E TPGS is about 1 : 1 to 1 : 4 . In one embodiment, the first purified cannabinoid is In one embodiment, the ratio of the total purified can CBGA . nabinoid content to Vitamin E TPGS is about 1 : 1 to 1 : 2 . In one embodiment, the aqueous cannabinoid formula- 30 In one embodiment, the composition disclosed herein is in tions disclosed herein comprise 50 to 99.9 % CBGA by the form of a tablet . percent mass . As used herein , the term “ tablet” refers to a dry solid . In In one embodiment, the first purified cannabinoid is one embodiment, the tablet is composed of active ingredi CBGV . ents , e.g. , a first purified cannabinoid . In one embodiment, In one embodiment, the aqueous cannabinoid formula- 35 the tablet is in dry form . In one embodiment, the tablet is tions disclosed herein comprise 50 to 99.9 % CBGV by made by molding or compressing a powder. In one example , percent mass . the tablet is made by compressing a dry powder of the active In one embodiment, the first purified cannabinoid is ingredients and a filler ( e.g., an excipient) forming a pill CBGVA . shape . In one embodiment , the tablet is a dosage of an active In one embodiment, the aqueous cannabinoid formula- 40 ingredient. In one embodiment , the dosage is determined by tions disclosed herein comprise 50 to 99.9 % CBGVA by the active ingredient (s ), e.g., a first purified cannabinoid . In percent mass . one embodiment, the tablet comprises an effervescent . As used herein , the term “ water soluble ” refers to a In one embodiment , the composition disclosed herein compound or compounds dissolvable in water or liquid . In comprises an alcohol. one embodiment, water soluble comprises dissolving a 45 In one embodiment, the composition disclosed herein compound in water. In one embodiment, dissolving com comprises ethanol. prises heating . In one embodiment, dissolving comprises As used herein , the term “ ethanol” refers to a compound stirring. In one embodiment, dissolving comprises shaking . with the following structural formula : In one embodiment , dissolving comprises mixing. In one embodiment, a powder is water soluble . In one embodiment, 50 a first purified cannabinoid composition is water soluble . H H H. In one embodiment, the compositions disclosed herein H — C — C comprise a second purified cannabinoid . In one embodi | - ment, the compositions disclosed herein comprise a third H H purified cannabinoid . In one embodiment, the compositions 55 disclosed herein comprise more than three purified cannabi Ethanol is a volatile , flammable , colorless liquid with a noids. In one embodiment, the compositions disclosed slight chemical odor. Ethanol is often used as an antiseptic , herein comprises a total purified cannabinoid content. a solvent, a fuel , and an active fluid in thermometers because As used herein , the term " total purified cannabinoid of its low freezing point . Ethanol is also present in some content” refers to the entire amount of identifiable cannabi- 60 tinctures and alcoholic beverages. noids within a composition . In one embodiment, the total In one embodiment, the compositions disclosed herein purified cannabinoid content is measured by grams. In one comprise a sugar. embodiment, the total purified cannabinoid content is mea As used herein , the term " sugar” refers to a compound sured by volume. In one embodiment, the total purified used by organisms to store energy . Sugar is often used in cannabinoid content is measured by moles. In one embodi- 65 food products as a sweetener and may provide other benefits , ment, the total purified cannabinoid content is measured by e.g., preservative , texture modifier, flavoring agent, bulking mass percent. In one embodiment, the total purified can agent, etc. In one embodiment, the sugar is a carbohydrate . US 10,722,490 B2 19 20 In one embodiment , the sugar is a monosaccharide. In one As used herein , the term “ cooling ” refers to lowering the embodiment, the sugar is a disaccharide. In one embodi temperature of a substance . In one embodiment, cooling ment , the sugar is a oligosaccharide. In one embodiment, the comprises dissipating heat through stirring . In one embodi sugar is a short composed of carbon , hydrogen , and oxygen . ment , cooling comprises placing a substance into a refrig In one embodiment, the sugar has the formula C „H2Omo 5 erator. In one embodiment, cooling comprises placing a wherein n is an integer . In one embodiment, n is 3. In one substance into a freezer. In one embodiment, cooling com embodiment, n is 4. In one embodiment, n is 5. In one prises allowing a substance to dissipate heat through equi embodiment, n is 6. In one embodiment, n is 7 . librium , e.g., allowing a substance to cool to ambient Within the context of this disclosure , the term sug?r may temperatures . also refer to a number of naturally occurring or synthetic 10 As used herein , the term “ temperature” refers to a mea compounds imparting sweetness . For example , maltodex surement of the average kinetic energy of the atoms or trin , sorbitol, stevia, mannitol, aspartame, sucralose , isomalt , molecules in a system , e.g. , a confined space , e.g. , a room , xylitol, etc. a cup , a container , etc. In one embodiment, temperature In one embodiment, the sugar is fructose . In one embodi measures the average kinetic energy of a room . In one ment, the sugar is sucrose. In one embodiment, the compo 15 embodiment, temperature measures the average kinetic sitions disclosed herein comprise more than one sugar. In energy of a sample . In one embodiment, temperature is one embodiment , the compositions disclosed herein com measured by a thermometer. In one embodiment, tempera prise sucrose and fructose . ture is measured by a thermocouple . In one embodiment , Disclosed herein is a new method of making a water 20 temperature is expressed in units of Kelvin . In one embodi soluble composition having a first purified cannabinoid , ment, temperature is expressed in units of Fahrenheit . In one comprising: embodiment, temperature is expressed in units of Celsius . It separating a first purified cannabinoid from Cannabis is understood , that temperatures expressed in Kelvin , Fahr plant material ; enheit , or Celsius are convertible from one another and can adding the first purified cannabinoid to Vitamin E TPGS 25 refer to the same desired temperature . For example , O to create a mixture of Vitamin E TPGS and the first degrees Celsius, 32 degrees Fahrenheit , and 273 Kelvin all purified cannabinoid ; approximate the freezing temperature of water . heating said mixture to a first temperature ; In one embodiment, there is a first temperature . adding water to the mixture of Vitamin E TPGS and the In one embodiment , there is a first temperature is between first purified cannabinoid to create an aqueous cannabi- 30 50-110 degrees Celsius . noid formulation comprising the mixture of Vitamin E In one embodiment, there is a first temperature is between TPGS and the first purified cannabinoid ; and 60-100 degrees Celsius. cooling the aqueous formulation to a second temperature . In one embo nent, there is a first temperature is between As used herein , the term " separating a first cannabinoid 70-90 degrees Celsius . from Cannabis plant material” refers to isolating a cannabi- 35 In one embodiment, there is a first temperature is between noid from the rest of the plant material, i.e., purifying a 75-85 degrees Celsius. cannabinoid . Separation can be done by a number of tech In one embodiment, there is a second temperature . niques known in the art. For example , thin layer chroma In one embodiment, there is a first temperature is between tography, high performance liquid chromatography, gas 0-50 degrees Celsius . chromatography, electrophoresis , microscopy , supercritical 40 In one embodiment, there is a first temperature is between fluid chromatography, etc. 10-40 degrees Celsius. As used herein , the term “ plantmaterial ” refers to matter In one embodiment, there is a first temperature is between produced by a plant of genus Cannabis , e.g., structural 20-30 degrees Celsius. materials like cellulose and / or organelles used in the plant's In one embodiment , the methods disclosed herein com metabolism . In one embodiment, the plant material is a leaf. 45 prise : In one embodiment, the plant material is a stem . In one sonicating the aqueous cannabinoid formulation compris embodiment, the plant material is a whole ground up plant. ing the mixture of Vitamin E TPGS and the first As used herein , the term “ adding ” refers to combining two purified cannabinoid to create micelles ; or compounds together , for example when forming a com freezing the aqueous cannabinoid formulation comprising position . In one embodiment, the compounds are in a gas 50 the mixture of Vitamin E TPGS and the first purified phase . In one embodiment, the compounds are in a liquid cannabinoid ; phase. In one embodiment, the compounds are in a solid lowering pressure of the aqueous cannabinoid formula phase. In one embodiment, the compounds are in different tion comprising the mixture of Vitamin E TPGS and the states of matter. For example , one compound in a solid phase first purified cannabinoid ; and is combined with another compound in a liquid phase. In one 55 removing water from the aqueous cannabinoid formula embodiment, adding comprises mixing. In one embodiment, tion comprising the mixture of Vitamin E TPGS and the adding comprises heating. In one embodiment, adding com first purified cannabinoid to create a dry powder . prises shaking. As used herein , the term “ sonicating” refers to applying As used herein , the term “ heating ” refers to raising the sound energy. The chemical effects of sonic waves on temperature of a substance . In one embodiment, heating 60 chemical systems is called sonochemistry . Sonicating can be comprises applying a heat source , e.g., a lamp, a hot plate , used for a variety of purposes , including, but is not limited etc. In one embodiment, heating comprises placing a sub to , producing nanoparticles , speeding dissolution , and / or stance within a heat source , e.g., placing a sample into an disrupting biological material. Many variables, including the oven . In one embodiment , heating comprises utilizing a fire . power , speed , and ratio of ingredients , can affect the prop In one embodiment, heating comprises raising the tempera- 65 erties of the resulting product . In one embodiment, the ture of a liquid , e.g. , placing a liquid in a heat proof beaker power of the sound energy applied can determine the size of and placing the beaker onto a hot plate . micelles and / or reverse micelles . US 10,722,490 B2 21 22 As used herein , the term “ freezing ” refers to transforming In one embodiment, the method disclosed herein com a liquid or gas into a solid . In one embodiment, freezing prises sonicating the aqueous cannabinoid formulation of comprises falling below a freezing point. In one embodi Vitamin E TPGS and purified cannabinoid for about 5 to 60 ment , freezing comprises molecules gathering into clusters minutes . forming a crystal structure and growing continuously . In one 5 In one embodiment, the method disclosed herein com embodiment, freezing comprises an exothermic process through the release of heat and pressure . prises sonicating the aqueous cannabinoid formulation of As used herein , the term “ lowering the pressure ” refers minutesVitamin . E TPGS and purified cannabinoid for about 10 to 45 decreasing the force acting on an unit of area or increasing In one embodiment, the method disclosed herein com the area a force is acting on . In one embodiment, pressure is 10 prises sonicating the aqueous cannabinoid formulation of defined as force per unit area . In one embodiment, lowering Vitamin E TPGS and purified cannabinoid for about 15 to 30 pressure comprises keeping the force constant while increas minutes . ing the area . In one embodiment, lowering the pressure In one embodiment, the method disclosed herein com decreasescomprises . Inkeeping one embodimentthe area ,constant pressure whileis expressed the force in 15 prises sonicating the aqueous cannabinoid formulation of pascals (Pa ). In one embodiment, pressure is expressed in Vitamin E TPGS and purified cannabinoid for about 20 to 25 torres ( Torr ). In one embodiment, pressure is expressed in minutes . barye (Ba ). In one embodiment, pressure is expressed in In one embodiment, the micelles in the compositions standard atmospheres (atm ). disclosed herein are reverse micelles . In some contexts , the word pressure refers to the vapor or 20 In one embodiment, the method disclosed herein com equilibrium vapor pressure . Vapor pressure is the pressure prises freezing the aqueous cannabinoid formulation , by exerted by vapor in thermodynamic equilibrium with its lowering temperature to less than -20 degrees Celsius. condensed phases , either solid or liquid , at a given tempera In one embodiment, the method disclosed herein co ture in a closed system . prises freezing the aqueous cannabinoid formulation , by As used herein , the term “ removing water ” refers to 25 lowering temperature to between 5 to -20 degrees Celsius . eliminating water from a composition such that the compo In one embodiment, the method disclosed herein com sition is substantially free from water . In one embodiment, prises freezing the aqueous cannabinoid formulation , by the composition is 90 % free from water. In one embodiment, lowering temperature to between 0 to -30 degrees Celsius . the composition is 95 % free from water . In one embodiment, In one embodiment, the method disclosed herein com the composition is 99 % free from water. In one embodiment , 30 prises freezing the aqueous cannabinoid formulation , by removing water comprises heating the aqueous cannabinoid lowering temperature to between -10 to -40 degrees Cel formulation . In one embodiment, removing water comprises sius . drying the aqueous cannabinoid formulation for example , by In one embodiment, the method disclosed herein com applying a material that absorbs . In one embodiment, prises freezing the aqueous cannabinoid formulation , by removing water comprises applying a vacuum to the aque- 35 lowering temperature to between –20 to -50 degrees Cel ous cannabinoid formulation . In one embodiment , removing sius . water comprises suctioning the aqueous cannabinoid formu In one embodiment, the method disclosed herein com lation . In one embodiment, removing water comprises prises lowering the pressure of the aqueous cannabinoid exposing the aqueous cannabinoid formulation to a desic formulation to less than 100 Torr . cant. 40 In one embodiment , the method disclosed herein com EXAMPLES prises adding water to the mixture of Vitamin E TPGS and purified cannabinoid to create an aqueous cannabinoid for Example 1 mulation comprising Vitamin E TPGS and between 1 to 50 mg of purified cannabinoid per mL of water . 45 THC was purified , via chromatography , from a plant of In one embodiment, the method disclosed herein com genus Cannabis , resulting in a clear , slightly yellow oil. The prises adding water to themixture of Vitamin E TPGS and oil weighed 5.00 g . In a separate container 20.0 g of Vitamin purified cannabinoid to create an aqueous cannabinoid for E TPGS was measured . Both compounds were combined in mulation comprising Vitamin E TPGS and between 5 to 20 a container with 50 mL of water . The solution was sonicated mg of purified cannabinoid per mL of water . 50 for 15-20 minutes until a homogeneous mixture was formed . In one embodiment, the method disclosed herein com The solution was transferred to a tray, forming a thin layer prises adding water to themixture of Vitamin E TPGS and of about 2 cm in depth . The tray was then placed in a freezer purified cannabinoid to create an aqueous cannabinoid for for 8 hours resulting in a solid sheet. The solid sheet was mulation comprising Vitamin E TPGS and between 10 to 15 placed in a plastic bag and vacuumed sealed under reduced mg of purified cannabinoid per mL of water . 55 pressure for one hour . The tray was removed from the bag In one embodiment, the method disclosed herein com and placed in an oven for 1 hour . The tray cooled to ambient prises adding between 5 to 20 mg of purified cannabinoid temperature and then the thin layer was scraped with a per mL of water. scraper to afford a powder. If clumping occurred, a mortar In one embodiment, the method disclosed herein com and pestle was used to make a finer powder. The micelles prises adding between 6 to 18 mg of purified cannabinoid 60 were measured with a refractometer. per mL of water. In one embodiment, the method disclosed herein com Example 2 prises adding between 8 to 15 mg of purified cannabinoid per mL of water. CBD was purified , via chromatography, from a plant of In one embodiment, the method disclosed herein com- 65 genus Cannabis , resulting in a clear , slightly yellow oil. The prises adding between 10 to 12 mg of purified cannabinoid oil weighed 5.00 g. In a separate container 20.0 g of Vitamin per mL of water. E TPGS was measured . Both compounds were combined in US 10,722,490 B2 23 24 a container with 50 mL of water. The solution was sonicated for 8 hours resulting in a solid sheet. The solid sheet was for 15-20 minutes until a homogeneous mixture was formed . placed in a plastic bag and vacuumed sealed under reduced The solution was transferred to a tray, forming a thin layer pressure for one hour . The tray was removed from the bag of about 2 cm in depth . The tray was then placed in a freezer and placed in an oven for 1 hour. The tray cooled to ambient for 8 hours resulting in a solid sheet. The solid sheet was 5 temperature and then the thin layer was scraped with a placed in a plastic bag and vacuumed sealed under reduced scraper to afford a powder . If clumping occurred , a mortar pressure for one hour. The tray was removed from the bag and pestle was used to make a finer powder . The micelles and placed in an oven for 1 hour. The tray cooled to ambient were measured with a refractometer. temperature and then the thin layer was scraped with a scraper to afford a powder . If clumping occurred , a mortar 10 Example 6 and pestle was used to make a finer powder . The micelles were measured with a refractometer . THC , CBD , and THCV were purified , via chromatogra phy, from a plant of genus Cannabis , resulting in a clear, Example 3 slightly yellow oil . Linalool, Alpha - Pinene , Eucalyptol, 15 Pulegone and Terpinolene were each purified from plant THCV was purified , via chromatography, from a plant of matter via chromatography. The purified terpenes were genus Cannabis , resulting in a clear , slightly yellow oil. The added to the Cannabis oil . The final cannabinoid and terpene oil weighed 5.00 g . In a separate container 20.0 g of Vitamin oil weighed 5.00 grams. In a separate container 20.0 g of E TPGS was measured . Both compounds were combined in Vitamin E TPGS was measured . The cannabinoid and ter a container with 50 mL of water . The solution was sonicated 20 pene oil and Vitamin E TPGS were combined in a separate for 15-20 minutes until a homogeneous mixture was formed . container with 50 mL of water. The solution was sonicated The solution was transferred to a tray, forming a thin layer for 15-20 minutes until a homogeneous mixture was formed . of about 2 cm in depth . The tray was then placed in a freezer The solution was transferred to a tray, forming a thin layer for 8 hours resulting in a solid sheet . The solid sheet was of about 2 cm in depth . The tray was then placed in a freezer placed in a plastic bag and vacuumed sealed under reduced 25 for 8 hours resulting in a solid sheet. The solid sheet was pressure for one hour . The tray was removed from the bag placed in a plastic bag and vacuumed sealed under reduced and placed in an oven for 1 hour . The tray cooled to ambient pressure for one hour . The tray was removed from the bag temperature and then the thin layer was scraped with a and placed in an oven for 1 hour. The tray cooled to ambient scraper to afford a powder. If clumping occurred, a mortar temperature and then the thin layer was scraped with a and pestle was used to make a finer powder. The micelles 30 scraper to afford a powder . If clumping occurred , a mortar were measured with a refractometer. and pestle was used to make a finer powder. The micelles were measured with a refractometer. Example 4 Example 7 THC , CBD , and CBGV were purified , via chromatogra- 35 phy, from a plant of genus Cannabis , resulting in a clear, THC , CBD , and THCV were purified , via chromatogra slightly yellow oil. The oil weighed 5.00 g . In a separate phy, from a plant of genus Cannabis , resulting in a clear, container 20.0 g of Vitamin E TPGS was measured . Both slightly yellow oil . Beta - Caryophyllene , Linalool, and Ter compounds were combined in a container with 50 mL of pineol were each purified from plant matter via chromatog water . The solution was sonicated for 15-20 minutes until a 40 raphy. The purified terpenes were added to the Cannabis oil . homogeneous mixture was formed . The final cannabinoid and terpene oil weighed 5.00 grams. The solution was transferred to a tray, forming a thin layer In a separate container 20.0 g of Vitamin E TPGS was of about 2 cm in depth . The tray was then placed in a freezer measured . The cannabinoid and terpene oil and Vitamin E for 8 hours resulting in a solid sheet. The solid sheet was TPGS were combined in a separate container with 50 mL of placed in a plastic bag and vacuumed sealed under reduced 45 water. The solution was sonicated for 15-20 minutes until a pressure for one hour. The tray was removed from the bag homogeneous mixture was formed . and placed in an oven for 1 hour . The tray cooled to ambient The solution was transferred to a tray , forming a thin layer temperature and then the thin layer was scraped with a of about 2 cm in depth . The tray was then placed in a freezer scraper to afford a powder . If clumping occurred , a mortar for 8 hours resulting in a solid sheet. The solid sheet was and pestle was used to make a finer powder. The micelles 50 placed in a plastic bag and vacuumed sealed under reduced were measured with a refractometer . pressure for one hour. The tray was removed from the bag and placed in an oven for 1 hour. The tray cooled to ambient Example 5 temperature and then the thin layer was scraped with a scraper to afford a powder . If clumping occurred , a mortar THC , CBD , and THCV were purified , via chromatogra- 55 and pestle was used to make a finer powder . The micelles phy, from a plant of genus Cannabis, resulting in a clear, were measured with a refractometer. slightly yellow oil. Alpha - Pinene, Alpha -Humulene , and Terpinolene were each purified from plant matter via chro Example 8 matography. The purified terpenes were added to the Can nabis oil . The final cannabinoid and terpene oil weighed 60 THC , CBD , and THCV were purified , via chromatogra 5.00 grams. In a separate container 20.0 g of Vitamin E phy , from a plant of genus Cannabis , resulting in a clear, TPGS was measured . The cannabinoid and terpene oil and slightly yellow oil. Beta - Caryophyllene , Linalool, and Vitamin E TPGS were combined in a separate container with Cymene were each purified from plant matter via chroma 50 mL of water. The solution was sonicated for 15-20 tography . The purified terpenes were added to the Cannabis minutes until a homogeneous mixture was formed . 65 oil. The final cannabinoid and terpene oil weighed 5.00 The solution was transferred to a tray , forming a thin layer grams. In a separate container 20.0 g of Vitamin E TPGS of about 2 cm in depth . The tray was then placed in a freezer was measured . The cannabinoid and terpene oil and Vitamin US 10,722,490 B2 25 26 E TPGS were combined in a separate container with 50 mL was heated to 80 degrees Celsius. After the mixture reached ofwater . The solution was sonicated for 15-20 minutes until 80 degrees Celsius , water was added while stirring until the a homogeneous mixture was formed . mixture turned into a viscous, amorphous mass . The beaker was removed from the hot plate and the mixture allowed to of aboutThe solution 2 cm in was depth transferred . The tray to was a tray then , forming placed ain thina freezer layer 5 cool to room temperature while stirring resulting in an for 8 hours resulting in a solid sheet. The solid sheet was aqueous solution . placed in a plastic bag and vacuumed sealed under reduced Example 12 pressure for one hour . The tray was removed from the bag and placed in an oven for 1 hour . The tray cooled to ambient CBD was purified , via chromatography , from a plant of temperature and then the thin layer was scraped with a 10 genus Cannabis , resulting in a clear, slightly yellow oil. The scraper to afford a powder. If clumping occurred, a mortar oil weighed 5.00 g . In a separate container 20.0 g of Vitamin and pestle was used to make a finer powder . The micelles E TPGS was measured . Both compounds were combined in were measured with a refractometer . a heat proof beaker and placed on a hot plate . The mixture was heated to 80 degrees Celsius . After the mixture reached Example 9 15 80 degrees Celsius , water was added while stirring until the mixture turned into a viscous, amorphous mass . The beaker THC , CBD , and THCV were purified , via chromatogra was removed from the hot plate and solution . phy, from a plant of genus Cannabis , resulting in a clear, slightly yellow oil. Alpha- Pinene , Linalool, Cymene , and Example 13 Terpineol were each purified from plantmatter via chroma- 20 THCV was purified , via chromatography, from a plant of tography . The purified terpenes were added to the Cannabis genus Cannabis , resulting in a clear , slightly yellow oil. The oil . The final cannabinoid and terpene oil weighed 5.00 oil weighed 5.00 g . In a separate container 20.0 g of Vitamin grams. In a separate container 20.0 g of Vitamin E TPGS E TPGS was measured . Both compounds were combined in was measured . The cannabinoid and terpene oil and Vitamin a heat proof beaker and placed on a hot plate . The mixture E TPGS were combined in a separate container with 50 mL 25 was heated to 80 degrees Celsius. After the mixture reached of water. The solution was sonicated for 15-20 minutes until 80 degrees Celsius, water was added while stirring until the a homogeneous mixture was formed . mixture turned into a viscous, amorphous mass . The beaker The solution was transferred to a tray , forming a thin layer was removed from the hot plate and the mixture allowed to of about 2 cm in depth . The tray was then placed in a freezer cool to room temperature while stirring resulting in an for 8 hours resulting in a solid sheet. The solid sheet was 30 aqueous solution . placed in a plastic bag and vacuumed sealed under reduced pressure for one hour . The tray was removed from the bag Example 14 and placed in an oven for 1 hour. The tray cooled to ambient temperature and then the thin layer was scraped with a THC , CBD , and CBGV were purified , via chromatogra scraper to afford a powder. If clumping occurred, a mortar 35 phy, from a plant of genus Cannabis, resulting in a clear, and pestle was used to make a finer powder . The micelles slightly yellow oil. The oil weighed 5.00 g . In a separate container 20.0 g of Vitamin E TPGS was measured . Both were measured with a refractometer . compounds were combined in a heat proof beaker and Example 10 placed on a hot plate . The mixture was heated to 80 degrees 40 Celsius. After the mixture reached 80 degrees Celsius, water THCA , CBC , THC , CBN , CBD , CBG , CBGA , and was added while stirring until the mixture turned into a CBDA were purified , via chromatography, from a plant of viscous, amorphous mass . The beaker was removed from the genus Cannabis , resulting in a clear , slightly yellow oil. hot plate and the mixture allowed to cool to room tempera The cannabinoid oil weighed 5.00 grams. In a separate ture while stirring resulting in an aqueous solution . container 20.0 g of Vitamin E TPGS was measured . The 45 Example 15 cannabinoid and terpene oil and Vitamin E TPGS were combined in a separate container with 50 mL of water. The THC , CBD , and THCV were purified , via chromatogra solution was sonicated for 15-20 minutes until a homoge phy, from a plant of genus Cannabis , resulting in a clear , neous mixture was formed . slightly yellow oil. Alpha - Pinene, Alpha -Humulene , and The solution was transferred to a tray, forming a thin layer 50 Terpinolene were each purified from plantmatter via chro of about 2 cm in depth . The tray was then placed in a freezer matography. The purified terpenes were added to the Can for 8 hours resulting in a solid sheet. The solid sheet was nabis oil . The final cannabinoid and terpene oil weighed placed in a plastic bag and vacuumed sealed under reduced 5.00 grams. pressure for one hour . The tray was removed from the bag In a separate container 20.0 g of Vitamin E TPGS was and placed in an oven for 1 hour. The tray cooled to ambient 55 measured . The cannabinoid and terpene oil was combined temperature and then the thin layer was scraped with a with Vitamin E TPGS in a heat proof beaker and placed on scraper to afford a powder . If clumping occurred , a mortar a hot plate . The mixture was heated to 80 degrees Celsius . and pestle was used to make a finer powder. The micelles After the mixture reached 80 degrees Celsius, water was were measured with a refractometer . added while stirring until the mixture turned into a viscous, 60 amorphous mass . The beaker was removed from the hot Example 11 plate and the mixture allowed to cool to room temperature while stirring resulting in an aqueous solution . THC was purified , via chromatography , from a plant of genus Cannabis , resulting in a clear, slightly yellow oil. The Example 16 oilweighed 5.00 g . In a separate container 20.0 g of Vitamin 65 E TPGS was measured . Both compounds were combined in THC , CBD , and THCV were purified , via chromatogra a heat proof beaker and placed on a hot plate . The mixture phy, from a plant of genus Cannabis , resulting in a clear , US 10,722,490 B2 27 28 slightly yellow oil. Linalool, Alpha- Pinene, Eucalyptol, amorphous mass . The beaker was removed from the hot Pulegone and Terpinolene were each purified from plant plate and the mixture allowed to cool to room temperature matter via chromatography. The purified terpenes were while stirring resulting in an aqueous solution . added to the Cannabis oil . The final cannabinoid and terpene oil weighed 5.00 grams. 5 Example 20 In a separate container 20.0 g of Vitamin E TPGS was THCA , CBC , THC, CBN , CBD , CBG , CBGA , and measured . The cannabinoid and terpene oil was combined CBDA were purified , via chromatography , from a plant of with Vitamin E TPGS in a heat proof beaker and placed on genus Cannabis, resulting in a clear , slightly yellow oil. The a hot plate . The mixture was heated to 80 degrees Celsius . 10 oil weighed 5.00 grams. After the mixture reached 80 degrees Celsius, water was In a separate container 20.0 g of Vitamin E TPGS was added while stirring until the mixture turned into a viscous , measured . The cannabinoid oil was combined with Vitamin amorphous mass. The beaker was removed from the hot E TPGS in a heat proof beaker and placed on a hot plate . The plate and the mixture allowed to cool to room temperature mixture was heated to 80 degrees Celsius. After the mixture while stirring resulting in an aqueous solution . 15 reached 80 degrees Celsius, water was added while stirring Example 17 until the mixture turned into a viscous, amorphous mass . The beaker was removed from the hot plate and the mixture THC , CBD , and THCV were purified , via chromatogra allowed to cool to room temperature while stirring resulting phy , from a plant of genus Cannabis , resulting in a clear, in an aqueous solution . slightly yellow oil. Beta - Caryophyllene, Linalool, and Ter- 20 Although the present invention herein has been described pineol were each purified from plant matter via chromatog with reference to various exemplary embodiments , it is to be raphy . The purified terpenes were added to the Cannabis oil. understood that these embodiments are merely illustrative of The final cannabinoid and terpene oil weighed 5.00 grams. the principles and applications of the present invention . In a separate container 20.0 g of Vitamin E TPGS was Those having skill in the art would recognize that various measured . The cannabinoid and terpene oil was combined 25 modifications to the exemplary embodiments may be made, with Vitamin E TPGS in a heat proof beaker and placed on without departing from the scope of the invention . Moreover , it should be understood that various features a hot plate . The mixture was heated to 80 degrees Celsius. and / or characteristics of differing embodiments herein may After the mixture reached 80 degrees Celsius, water was be combined with one another. It is therefore to be under addedamorphous while mass stirring . The until beaker the mixture was removed turned intofrom a viscousthe hot, 30 stood that numerous modifications may be made to the plate and the mixture allowed to cool to room temperature illustrative embodiments and that other arrangements may while stirring resulting in an aqueous solution . be devised without departing from the scope of the inven tion . Example 18 Furthermore, other embodiments of the invention will be 35 apparent to those skilled in the art from consideration of the THC , CBD , and THCV were purified , via chromatogra specification and practice of the invention disclosed herein . phy, from a plant of genus Cannabis , resulting in a clear, It is intended that the specification and examples be con slightly yellow oil. Beta - Caryophyllene, Linalool, and sidered as exemplary only , with a scope and spirit being Cymene were each purified from plant matter via chroma indicated by the claims. tography . The purified terpenes were added to the Cannabis 40 Finally , it is noted that, as used in this specification and oil. The final cannabinoid and terpene oil weighed 5.00 the appended claims, the singular forms“ a ,” “ an , ” and “ the ,” grams. include plural referents unless expressly and unequivocally In a separate container 20.0 g of Vitamin E TPGS was limited to one referent, and vice versa . As used herein , the measured . The cannabinoid and terpene oil was combined term “ include” or “ comprising ” and its grammatical variants with Vitamin E TPGS in a heat proof beaker and placed on 45 are intended to be non - limiting , such that recitation of an a hot plate . The mixture was heated to 80 degrees Celsius. item or items is not to the exclusion of other like items that After the mixture reached 80 degrees Celsius , water was can be substituted or added to the recited item ( s ) . added while stirring until the mixture turned into a viscous , amorphous mass . The beaker was removed from the hot What is claimed is : plate and the mixture allowed to cool to room temperature 50 1. A liquid composition , comprising: while stirring resulting in an aqueous solution . one or more purified cannabinoids ; one or more purified terpenes; Example 19 Vitamin E TPGS ; and water . THC , CBD , and THCV were purified , via chromatogra- 55 2. The liquid composition of claim 1 , comprising a ratio phy, from a plant of genus Cannabis , resulting in a clear, of Vitamin E TPGS to the one or more purified cannabinoids slightly yellow oil . Alpha - Pinene, Linalool, Cymene, and of about 85:15 to about 75:25 by percent mass . Terpineol were each purified from plant matter via chroma 3. The liquid composition of claim 1 , comprising a ratio tography. The purified terpenes were added to the Cannabis of Vitamin E TPGS to the one or more purified cannabinoids oil . The final cannabinoid and terpene oil weighed 5.00 60 of about 82:18 to about 78:22 by percent mass . grams. 4. The liquid composition of claim 1 , comprising a In a separate container 20.0 g of Vitamin E TPGS was micelle . measured . The cannabinoid and terpene oil was combined 5. A method of making a liquid composition having one with Vitamin E TPGS in a heat proof beaker and placed on or more purified cannabinoids and one or more purified a hot plate . The mixture was heated to 80 degrees Celsius . 65 terpenes, comprising: After the mixture reached 80 degrees Celsius , water was separating one or more purified cannabinoids and one or added while stirring until the mixture turned into a viscous , more purified terpenes from a cannabis plant material ; US 10,722,490 B2 29 30 adding the one or more purified cannabinoids and the one 9. The liquid composition of claim 1, wherein the one or or more purified terpenes to Vitamin E TPGS to create more purified cannabinoids is THCA , CBC , THC , CBN , a mixture of Vitamin E TPGS and the one or more CBD , CBG , CBGA , CBDA , or a combination thereof. purified cannabinoids and one or more purified ter 10. The liquid composition of claim 1 , wherein the one or penes ; 5 heating said mixture to a first temperature ; more purified cannabinoids is CBD , THC , THCV , or a adding water to the mixture to create an aqueous formu combination thereof . lation comprising the mixture of Vitamin E TPGS and 11. The liquid composition of claim 10 , wherein the the one or more purified cannabinoids and one or more combination comprises THC , CBD and THCV. terpenes ; and 12. The liquid composition of claim 1 , wherein the one or cooling the aqueous formulation to a second temperature . 10 more purified terpenes is linalool, alpha - pinene, alpha -hu 6. The method of claim 5 , comprising : mulene, terpinolene, eucalyptol, pulegone , terpineol, beta sonicating the aqueous formulation comprising the mix caryophyllene, cymene, or a combination thereof. ture of Vitamin E TPGS and the one or more purified 13. The liquid composition of claim 11, wherein the liquid cannabinoids and one or more terpenes to create 15 composition comprises beta -caryophyllene , linalool, and freezingmicelles the ; aqueous formulation comprising the mixture cymene as purified terpenes. of Vitamin E TPGS and the one or more purified 14. The liquid composition of claim 4 , wherein the one or cannabinoids and one or more terpenes; more cannabinoids and /or the one or more terpenes are lowering pressure of the aqueous formulation comprising contained within the micelles . the mixture of Vitamin E TPGS and the one or more 20 15. The liquid composition of claim 1, comprising a ratio purified cannabinoids and one or more terpenes ; of Vitamin E TPGS to a combined amount of the one or removing water from the aqueous formulation comprising more purified cannabinoids and the one or more purified the mixture of Vitamin E TPGS and the one or more terpenes of about 85:15 to about 75:25 by percent mass . purified cannabinoids and one or more terpenes to 16. The liquid composition of claim 1 , comprising a ratio create a dry powder ; and 25 of Vitamin E TPGS to a combined amount of the one or adding water to the dry powder to create a liquid can more purified cannabinoids and the one or more purified nabinoid composition comprising Vitamin E TPGS and terpenes of about 85:15 to about 75:25 by percent mass. the one or more purified cannabinoids and one or more 17. The method of claim 6 , wherein adding water to the terpenes . dry powder creates a liquid cannabinoid composition com comprises7. The methodreverse micellesof claim . 6, wherein the dry powder 30 prising Vitamin E TPGS and between 5 to 20 mg of the one 8. The method of claim 6 , wherein the first temperature is or more purified cannabinoids and one or more terpenes per between 70-90 degrees Celsius; and wherein the second mL of water. temperature is between 0-50 degrees Celsius .