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.
METHODS FOR PREPARING CANNABINOIDS AND RELATED INSTRUMENTS
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Paragraph 0046, (2021/10/15)
Methods and instrumentation for converting cannabidiol (CBD) and CBD-like compounds to other naturally-occurring or synthetic cannabinoids, such as THC, CBN and/or CBC, which processes may be solvent-free, Generally, the conversion of CBD is carried out in the presence of a Lewis acid, an oxidant or both, which may be present in catalytic amounts. A reaction may be a two-phase reaction with the Lewis acid present on a support material in a column or similar chamber through which CBD passes and is converted to the cannabinoids. The reactions allow direction of relative yields of certain cannabinoid products by altering the identity of the acid reagent.
Antioxidant function of phytocannabinoids: Molecular basis of their stability and cytoprotective properties under UV-irradiation
Vacek, Jan,Vostalova, Jitka,Papouskova, Barbora,Skarupova, Denisa,Kos, Martin,Kabelac, Martin,Storch, Jan
, p. 258 - 270 (2021/02/05)
In this contribution, a comprehensive study of the redox transformation, electronic structure, stability and photoprotective properties of phytocannabinoids is presented. The non-psychotropic cannabidiol (CBD), cannabigerol (CBG), cannabinol (CBN), cannabichromene (CBC), and psychotropic tetrahydrocannabinol (THC) isomers and iso-THC were included in the study. The results show that under aqueous ambient conditions at pH 7.4, non-psychotropic cannabinoids are slight or moderate electron-donors and they are relatively stable, in the following order: CBD > CBG ≥ CBN > CBC. In contrast, psychotropic Δ9-THC degrades approximately one order of magnitude faster than CBD. The degradation (oxidation) is associated with the transformation of OH groups and changes in the double-bond system of the investigated molecules. The satisfactory stability of cannabinoids is associated with the fact that their OH groups are fully protonated at pH 7.4 (pKa is ≥ 9). The instability of CBN and CBC was accelerated after exposure to UVA radiation, with CBD (or CBG) being stable for up to 24 h. To support their topical applications, an in vitro dermatological comparative study of cytotoxic, phototoxic and UVA or UVB photoprotective effects using normal human dermal fibroblasts (NHDF) and keratinocytes (HaCaT) was done. NHDF are approx. twice as sensitive to the cannabinoids’ toxicity as HaCaT. Specifically, toxicity IC50 values for CBD after 24 h of incubation are 7.1 and 12.8 μM for NHDF and HaCaT, respectively. None of the studied cannabinoids were phototoxic. Extensive testing has shown that CBD is the most effective protectant against UVA radiation of the studied cannabinoids. For UVB radiation, CBN was the most effective. The results acquired could be used for further redox biology studies on phytocannabinoids and evaluations of their mechanism of action at the molecular level. Furthermore, the UVA and UVB photoprotectivity of phytocannabinoids could also be utilized in the development of new cannabinoid-based topical preparations.
