521-37-9

Usage

Uses

Used in Pharmaceutical Industry:
2-[(6R)-3-methyl-6-prop-1-en-2-yl-1-cyclohex-2-enyl]-5-pentyl-benzene-1,3-diol is used as a potential candidate for drug development due to its unique molecular structure and properties. Its complex arrangement of functional groups and rings may offer various opportunities for the creation of novel therapeutic agents, targeting a range of medical conditions and diseases. 2-[(6R)-3-methyl-6-prop-1-en-2-yl-1-cyclohex-2-enyl]-5-pentyl-benzene-1,3-diol's potential applications in the pharmaceutical industry are currently under exploration, with the aim of leveraging its distinctive characteristics for the advancement of healthcare and medicine.

Upstream product

• 1686-20-0 p‐mentha‐1,5‐dien‐8‐ol 
• 500-66-3 Olivetol 
• 22972-51-6 (1S,4R)-p-mentha-2,8-dien-1-ol 
• 20053-58-1 (1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide 
• 936-91-4 3-carene epoxide 
• 861892-40-2 (4R)-1-methyl-4-(2-(1-propylene))-2-cyclohexene-2-ol 
• 55658-71-4 methyl (1'R,2'R)-2,6-dihydroxy-5'-methyl-4-pentyl-2'-(prop-1 -en-2- yl)-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-3-carboxylate 
• 3411-09-4 (E)-4-(2,6-dimethoxy-4-pentylphenyl)but-3-en-2-one 
• 3410-84-2 2,6-dimethoxy-4-pentylbenzaldehyde 

Downstream Products

• 43009-38-7 (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 1972-08-3 dronabinol 
• 32209-09-9 2-((1R,2R,5R)-2-Isopropenyl-5-methoxy-5-methyl-cyclohexyl)-5-pentyl-benzene-1,3-diol 
• 32209-08-8 2-((1R,2R,5S)-2-Isopropenyl-5-methoxy-5-methyl-cyclohexyl)-5-pentyl-benzene-1,3-diol 
• 4460-20-2 5-Pentyl-2-((1R)-3c-methyl-6t-isopropyl-cyclohexyl-(1r))-resorcin 
• 17766-02-8 (+)-(3S,4S)-delta-1-tetrahydrocannabinol 

Relevant academic research and scientific papers

Stereoselective Synthesis of Nonpsychotic Natural Cannabidiol and Its Unnatural/Terpenyl/Tail-Modified Analogues

Here, we report a three-step concise and stereoselective synthesis route to one of the most important phytocannabinoids, namely, (-)-cannabidiol (-CBD), from inexpensive and readily available starting material R-(+)-limonene. The synthesis involved the diastereoselective bifunctionalization of limonene, followed by effective elimination leading to the generation of key chiral p-mentha-2,8-dien-1-ol. The chiral p-mentha-2,8-dien-1-ol on coupling with olivetol under silver catalysis provided regiospecific (-)-CBD, contrary to reported ones which gave a mixture. The newly developed approach was further extended to its structural analogues cannabidiorcin and other tail/terpenyl-modified analogues. Moreover, its opposite isomer (+)-cannabidiol was also successfully synthesized from S-(-)-limonene.

CANNABIS EXTRACTS AND USES THEREOF

The present disclosure concerns a group of cannabinoid compounds defined by formulas (I) to (IV), wherein R1 is —H or —COOH, for the first time isolated and fully characterized in structure, absolute stereochemistry by the present applicant. Methods of isolation, characterization, stereoselective synthesis, biological activity, pharmaceutical compositions and therapeutic applications of the present compounds as modulators of the cannabinoid CB1 receptor are also object of the disclosure.

PROCESS FOR THE SYNTHESIS OF CANNABIDIOL AND INTERMEDIATES THEREOF

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

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.

Design of Negative and Positive Allosteric Modulators of the Cannabinoid CB2Receptor Derived from the Natural Product Cannabidiol

Cannabidiol (CBD), the second most abundant of the active compounds found in the Cannabis sativa plant, is of increasing interest because it is approved for human use and is neither euphorizing nor addictive. Here, we design and synthesize novel compounds taking into account that CBD is both a partial agonist, when it binds to the orthosteric site, and a negative allosteric modulator, when it binds to the allosteric site of the cannabinoid CB2 receptor. Molecular dynamic simulations and site-directed mutagenesis studies have identified the allosteric site near the receptor entrance. This knowledge has permitted to perform structure-guided design of negative and positive allosteric modulators of the CB2 receptor with potential therapeutic utility.

(+)-TRANS TETRAHYDROCANNABINOL ((+)-TRANS-THC) FOR USE AS A MEDICAMENT

The present invention relates to a tetrahydrocannabinol (THC) type cannabinoid compound for use as a medicament. The THC-type cannabinoid is an enantiomer of the (-)-trans- tetrahydrocannabinol which is a naturally occurring cannabinoid that can be found in cannabis plant strains which have been bred to yield THC as the dominant cannabinoid. The particular enantiomer (+)-trans tetrahydrocannabinol has been found to have properties which are different from the naturally occurring (-)-trans-THC. The cannabinoid (+)-trans-THC has been found to occur in low concentrations in particular cannabis plant strains. Furthermore, the cannabinoid can be produced by synthetic means.

(+)-trans-Cannabidiol-2-hydroxy pentyl is a dual CB1R antagonist/CB2R agonist that prevents diabetic nephropathy in mice

Natural cannabidiol ((-)-CBD) and its derivatives have increased interest for medicinal applications due to their broad biological activity spectrum, including targeting of the cannabinoid receptors type 1 (CB1R) and type 2 (CB2R). Herein, we synthesized the (+)-enantiomer of CBD and its derivative (+)-CBD hydroxypentylester ((+)-CBD-HPE) that showed enhanced CB1R and CB2R binding and functional activities compared to their respective (-) enantiomers. (+)-CBD-HPE Ki values for CB1R and CB2R were 3.1 ± 1.1 and 0.8 ± 0.1 nM respectively acting as CB1R antagonist and CB2R agonist. We further tested the capacity of (+)-CBD-HPE to prevent hyperglycemia and its complications in a mouse model. (+)-CBD-HPE significantly reduced streptozotocin (STZ)-induced hyperglycemia and glucose intolerance by preserving pancreatic beta cell mass. (+)-CBD-HPE significantly reduced activation of NF-κB by phosphorylation by 15% compared to STZ-vehicle mice, and CD3+ T cell infiltration into the islets was avoided. Consequently, (+)-CBD-HPE prevented STZ-induced apoptosis in islets. STZ induced inflammation and kidney damage, visualized by a significant increase in plasma proinflammatory cytokines, creatinine, and BUN. Treatment with (+)-CBD-HPE significantly reduced 2.5-fold plasma IFN-γ and increased 3-fold IL-5 levels compared to STZ-treated mice, without altering IL-18. (+)-CBD-HPE also significantly reduced creatinine and BUN levels to those comparable to healthy controls. At the macroscopy level, (+)-CBD-HPE prevented STZ-induced lesions in the kidney and voided renal fibrosis and CD3+ T cell infiltration. Thus, (+)-enantiomers of CBD, particularly (+)-CBD-HPE, have a promising potential due to their pharmacological profile and synthesis, potentially to be used for metabolic and immune-related disorders.

Using (+)-carvone to access novel derivatives of (+)-ent-cannabidiol: The first asymmetric syntheses of (+)-ent-CBDP and (+)-ent-CBDV

(?)-Cannabidiol [(?)-CBD] has recently gained prominence as a treatment for neuro-inflammation and other neurodegenerative disorders; interest is also developing in its synthetic enantiomer, (+)-CBD, which has a higher affinity to CB1/CB2 receptors than the natural stereoisomer. We have developed an inexpensive, stereoselective route to access ent-CBD derivatives using (+)-carvone as a starting material. In addition to (+)-CBD, we report the first syntheses of (+)-cannabidivarin, (+)-cannabidiphorol as well as C-6/C-8 homologues.

STABLE CANNABINOID COMPOSITIONS

The present application discloses powder and aqueous formulations. These include but are not limited to water dispersible cannabinoid formulations, especially those comprising cannabidiol (CBD), cannabigerol (CBG), and cannabinol (CBN) as well as other cannabinoids. Generally, these embodiments do not include major amounts of Tetrahydrocannabinol (THC), but certain embodiments are envisioned that do contain measurable concentrations of THC. Embodiments may include one or more emulsifiers selected from the group consisting of Tween (polysorbate) 20, Tween 60, Tween 80, Span 20, Span 60, Span 80, Poloxamer 188, Vit E-TPGS (TPGS), TPGS-1000, TPGS-750-M, Solutol HS 15, PEG-40 hydrogenated castor oil, PEG-35 Castor oil, PEG-8-glyceryl capylate/caprate, PEG-32-glyceryl laurate, PEG-32-glyceryl palmitostearate, Polysorbate 85, polyglyceryl-6-dioleate, sorbitan monooleate, Capmul MCM, Maisine 35-1, glyceryl monooleate, glyceryl monolinoleate, PEG-6-glyceryl oleate, PEG-6-glyceryl linoleate, oleic acid, linoleic acid, propylene glycol monocaprylate, propylene glycol monolaurate, polyglyceryl-3 dioleate, polyglyceryl-3 diisostearate and lecithin.

BIOACTIVE PHENOLATE IONIC COMPLEXES

The invention provides an isolated material, or a phenolate form of at least one phenol- containing active material, wherein the isolated material comprises one or more phenolate species and a counter ion (a cation) in the form of a metal salt, a phosphonium or an ammonium.