20675-51-8Relevant articles and documents
Constituents of Cannabis sativa L. An improved method for the synthesis of dl-cannabichromene
ElSohly,Boeren,Turner
, p. 699 - 700 (1978)
A new procedure was developed for the synthesis of cannabichromene (III) which involves reflux of equimolar amounts of olivetol (I), citral (II) and t-butylamine in toluene for 9 hours. The purification of III was best achieved by sodium borohydride reduction of unreacted II followed by column chromatography on 1% sodium hydroxide impregnated silica gel 60-PF. The yield of III (62.0%) was much higher than that reported in the literature.
Cannabichromene is a cannabinoid CB2 receptor agonist
Udoh, Michael,Santiago, Marina,Devenish, Steven,McGregor, Iain S.,Connor, Mark
, p. 4537 - 4547 (2019)
Background and Purpose: Cannabichromene (CBC) is one of the most abundant phytocannabinoids in Cannabis spp. It has modest antinociceptive and anti-inflammatory effects and potentiates some effects of Δ9-tetrahydrocannabinol in vivo. How CBC exerts these effects is poorly defined and there is little information about its efficacy at cannabinoid receptors. We sought to determine the functional activity of CBC at cannabinoid CB1 and CB2 receptors. Experimental Approach: AtT20 cells stably expressing haemagglutinin-tagged human CB1 and CB2 receptors were used. Assays of cellular membrane potential and loss of cell surface receptors were performed. Key Results: CBC activated CB2 but not CB1 receptors to produce hyperpolarization of AtT20 cells. This activation was inhibited by a CB2 receptor antagonist AM630, and sensitive to Pertussis toxin. Application of CBC reduced activation of CB2, but not CB1, receptors by subsequent co-application of CP55,940, an efficacious CB1 and CB2 receptor agonist. Continuous CBC application induced loss of cell surface CB2 receptors and desensitization of the CB2 receptor-induced hyperpolarization. Conclusions and Implications: CBC is a selective CB2 receptor agonist displaying higher efficacy than tetrahydrocannabinol in hyperpolarizing AtT20 cells. CBC can also recruit CB2 receptor regulatory mechanisms. CBC may contribute to the potential therapeutic effectiveness of some cannabis preparations, potentially through CB2 receptor-mediated modulation of inflammation.
A Total Synthesis of (±)-Rhododaurichromanic Acid A via an Oxa-[3+3] Annulation of Resorcinols
Luo, Guo-Ying,Wu, Hao,Tang, Yu,Li, Hui,Yeom, Hyun-Suk,Yang, Ka,Hsung, Richard P.
, p. 2713 - 2720 (2015)
Development of an oxa-[3+3] annulation of vinyliminium salts with resorcinols as a 1,3-diketo equivalent is described. This annulation constitutes a cascade of Knoevenagel condensation-oxa-electrocyclization leading to a direct access to chromenes. A series of attempts was made to demonstrate its synthetic utility in natural product synthesis, culminating in a total synthesis of (±)-rhododaurichromanic acid A that also featured an intramolecular Gassman-type cationic [2+2] cycloaddition.
CANNABICHROMENE COMPOSITIONS AND METHODS OF SYNTHESIZING CANNABICHROMENE
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Paragraph 0079; 0081; 0082; 0083; 0084-0087, (2021/07/02)
Compositions having enhanced cannabichromene (CBC) and abnormal cannabichromene (CBCab) concentrations are disclosed herein as are methods of synthesizing CBC and CBCab. Relative to conventional methods, the methods of the present disclosure may: (i) be better suited to large-scale conditions in that they do not require dangerous and/or toxic solvents and/or reagents; (ii) provide product mixtures with enhanced CBCab concentrations; (iii) provide CBC at higher yield; (iv) provide easier to purify product mixtures comprising CBC; (v) provide product mixtures that comprise unique ratios of CBCab relative to other cannabinoids; and/or (vi) provide product mixtures with reduced THC concentrations.
METHODS OF SYNTHESIZING HIGH-PURITY CANNABICYCLOL AND ARTIFICIAL RESINS COMPRISING CANNABICYCLOL
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Paragraph 00171, (2021/07/02)
Compositions having enhanced cannabicyclol (CBL) or CBL derivative concentrations are disclosed herein as are methods of synthesizing CBL and CBL derivative in high-purity form. Relative to conventional methods, the methods of the present disclosure may: (i) be better suited to large-scale conditions in that they do not require dangerous and/or toxic solvents and/or reagents; (ii) be more tolerant of complex starting compositions, such as cannabinoid extracts, isolates and/or distillates; (iii) provide CBL and/or CBL derivative at higher yield; (iv) provide easier methods to purify product mixtures comprising CBL and/or CBL derivative; (v) provide product mixtures that comprise unique ratios of CBL or CBL derivative relative to other cannabinoids; (vi) provide product mixtures with reduced THC concentrations and/or (vii) provide artificial resins having of a mixture cannabinoids that cannot be produced by extracting cannabis plant material.
