861892-40-2Relevant academic research and scientific papers
PROCESS FOR THE SYNTHESIS OF CANNABIDIOL AND INTERMEDIATES THEREOF
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Paragraph 0059, (2021/09/17)
The present invention relates to process for the preparation of cannabidiol (A) from the coupling of (D) and (E) through the intermediates (C) and (D) starting from compound (B). The invention further relates to the novel compounds (B), (C), (D) and (E) and reagents used in this process. More specifically, this invention provides the manufacturing of Cannabidiol (A) in milligram to gram or kilogram scale.
Method for continuously preparing cannabidiol intermediate through green photooxidation
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Paragraph 0077-0112, (2021/05/19)
The invention provides a method for continuously preparing a cannabidiol intermediate compound (4R)-1-methyl-4-(2-(1-propylene))-2-cyclohexene-2-ol (formula III) through photooxidation, which comprises the following steps: taking (R)-(+)-limonene (formula I-a) as an initial raw material, carrying out continuous photooxidation reaction in a photoreactor to obtain peroxide, and then carrying out reduction reaction to obtain an intermediate III. The technical route is simple and easy to implement, conditions are mild, column separation and purification are not needed, the production cost is greatly reduced, and industrial production is convenient to implement. The cannabidiol intermediate compound III is prepared by using a simple synthesis route, and the method has the advantages of simple process, less pollution, easiness in purification and the like.
Method for continuously preparing cannabidiol intermediate through green photooxidation
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Paragraph 0016; 0028-0029; 0038-0051, (2021/07/31)
The invention relates to a novel method for synthesizing cannabidiol (-)-Cannabidiol (CBD, formula I), aiming at solving the defects in the prior art. The production process is characterized by comprising the following steps that: (R)-(+)-Limonene (compound I-a) is adopted as an initial raw material; the initial raw material and a photocatalyst are subjected to an oxidation reaction under illumination,and then a reduction reaction is performed; and a pure key intermediate I-e is obtained through purification. The reaction formula involved in the steps is shown in the specification. The reaction and purification are simple; The method of the invention has the advantages of simple and easy-to-implement technical route, wide raw material source range, mild conditions, low production cost, high yield and environment-friendly performance, and provides a more effective synthesis method for industrial production.
Selective Catalytic Synthesis of 1,2- and 8,9-Cyclic Limonene Carbonates as Versatile Building Blocks for Novel Hydroxyurethanes
Maltby, Katarzyna A.,Hutchby, Marc,Plucinski, Pawel,Davidson, Matthew G.,Hintermair, Ulrich
supporting information, p. 7405 - 7415 (2020/05/25)
The selective catalytic synthesis of limonene-derived monofunctional cyclic carbonates and their subsequent functionalisation via thiol–ene addition and amine ring-opening is reported. A phosphotungstate polyoxometalate catalyst used for limonene epoxidation in the 1,2-position is shown to also be active in cyclic carbonate synthesis, allowing a two-step, one-pot synthesis without intermittent epoxide isolation. When used in conjunction with a classical halide catalyst, the polyoxometalate increased the rate of carbonation in a synergistic double-activation of both substrates. The cis isomer is shown to be responsible for incomplete conversion and by-product formation in commercial mixtures of 1,2-limomene oxide. Carbonation of 8,9-limonene epoxide furnished the 8,9-limonene carbonate for the first time. Both cyclic carbonates underwent thiol–ene addition reactions to yield linked di-monocarbonates, which can be used in linear non-isocyanate polyurethanes synthesis, as shown by their facile ring-opening with N-hexylamine. Thus, the selective catalytic route to monofunctional limonene carbonates gives straightforward access to monomers for novel bio-based polymers.
OXIDATION OF LIMONENE
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Paragraph 0043; 0045; 0046, (2018/06/15)
The invention discloses a process for the oxidation of limonene, comprising the reaction of limonene with hydrogen peroxide in the presence of a catalyst containing atoms and/or ions of at least one metal, selected from the group consisting of molybdenum, tungsten, scandium, vanadium, titanium, lanthanum, zirconium, praseodymium, neodymium, samarium, europium, terbium, dysprosium, erbium or ytterbium, characterised in that the molecular weight of the catalyst is less than 2,000 g/mol and that the reaction is performed at a pH value of more than 7.5.
Photooxidation and phototoxicity of π-extended squaraines
Rapozzi, Valentina,Beverina, Luca,Salice, Patrizio,Pagani, Giorgio A.,Camerin, Monica,Xodo, Luigi E.
experimental part, p. 2188 - 2196 (2010/08/06)
This paper describes the synthesis of π-extended squaraines and their photooxidation properties and gives an in-depth characterization of these molecules as photosensitizing agents. Squaraines show a strong absorption in the tissue transparency window (600-800 nm), and upon irradiation, they undergo a photooxidation process, leading to the formation of peroxide and hydroperoxide radicals according to a type I radical chain process. Confocal laser microscopy demonstrates that the designed squaraines efficiently internalize in the cytoplasm and not in the nucleus of the cell. In the dark, they are scarcely cytotoxic, but after irradition, they promote a strong dose-dependent phototoxic effect in four different cancer cells. In HeLa and MCF-7 cells, squaraines 4 and 5, thanks to their hydrocarbon tails, associate to the membranes and induce lipid peroxidation, as indicated by a marked increase of malonyldialdehyde after photodynamic treatment, in agreement with in vitro photooxidation studies. FACS, caspase-3/7 assays and time-lapse microscopy demonstrate that the designed squaraines cause cell death primarily by necrosis.
FLUORINATION OF ORGANIC COMPOUNDS
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Page/Page column 69;70, (2010/07/10)
Methods for fluorinating organic compounds are described herein.
Antibody-catalyzed oxidation of Δ9-tetrahydrocannabinol
Brogan, Andrew P.,Eubanks, Lisa M.,Koob, George F.,Dickerson, Tobin J.,Janda, Kirn D.
, p. 3698 - 3702 (2008/01/01)
Marijuana abuse continues to plague society and the lack of effective treatments warrants concern. Catalytic antibodies capable of oxidatively degrading the major psychoactive component of marijuana, Δ9- tetrahydrocannabinol (Δ9-THC), are presented. The antibodies generate reactive oxygen species from singlet oxygen (1O 2*), using riboflavin (vitamin B2) and visible light as the 1O2*source. Cannabitriol was identified as the major degradation product of this reaction, demonstrating the ability of an antibody to catalyze a complex chemical transformation with therapeutic implications for treating marijuana abuse.
Δ9-tetrahydrocannabinol immunochemical studies: Haptens, monoclonal antibodies, and a convenient synthesis of radiolabeled Δ9-tetrahydrocannabinol
Qi, Longwu,Yamamoto, Noboru,Meijler, Michael M.,Altobell III, Laurence J.,Koob, George F.,Wirsching, Peter,Janda, Kim D.
, p. 7389 - 7399 (2007/10/03)
Immunopharmacotherapy as an approach to combat drugs of abuse has become an active area of investigation. Marijuana is the most commonly used illicit drug in the U.S. The main active chemical in marijuana is Δ9- tetrahydrocannabinol (Δ9-THC); hence, monoclonal antibodies with high affinity and specificity for Δ9-tetrahydrocannabinol could be valuable immunopharmacotherapeutic intervention and diagnostic tools. We have synthesized immunoconjugates that induce an effective immune response to Δ9-THC and describe a convenient synthesis of radiolabeled Δ9-THC. We demonstrate the value and use of this probe to select anti-Δ9-THC antibodies that bind Δ9-THC with good affinity. The synthetic route to radiolabeled Δ9-THC has enabled the correct assessment of the affinity of these antibodies to their ligand and may facilitate future binding studies between Δ9- THC and its analogues and the cannabinoid receptors.
