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

• 22771-44-4 (+)-p-mentha-2,8-dien-1-ol 
• 500-66-3 Olivetol 
• 139-66-2 diphenyl sulfide 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 38862-65-6 2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester 
• 52154-82-2 (1R,4R)-p-mentha-2,8-dien-1-ol 
• 140633-48-3 Phosphoric acid (5R,6R)-6-(2,6-dimethoxy-4-pentyl-phenyl)-5-isopropenyl-2-methyl-cyclohex-1-enyl ester diethyl ester 
• 1686-20-0 p‐mentha‐1,5‐dien‐8‐ol 
• 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 
• 40525-15-3 (1′R,2′R)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl diacetate 
• 10293-10-4 3-endo-9-dibromo-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one 
• 705-76-0 3,5-dimethoxybenzyl alcohol 

Downstream Products

• 62461-69-2 cannabidiol 
• 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 
• 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 
• 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 
• 32209-10-2 4-Cyclohexyl-2-((1R,6R)-6-isopropenyl-3-methyl-cyclohex-2-enyl)-5-pentyl-benzene-1,3-diol 
• 4460-20-2 5-Pentyl-2-((1R)-3c-methyl-6t-isopropyl-cyclohexyl-(1r))-resorcin 
• 5957-75-5 delta-8-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.

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.

Method for preparing cannabinoids

Provided is a method for preparing synthetic cannabidiol, including hydrolysis-decarboxylation of a compound represented by formula (II) in a solvent-free state under atmospheric pressure. The method further includes preparation of the compound represented by formula (II). The method provides a safe, economical, environmentally friendly and scalable method for synthetic preparation of cannabidiol.

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.

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.

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.

Preparation method of cannabidiol

The invention discloses a preparation method of cannabidiol. To the method, malonate type compounds and hexanal serve as starting materials, Knoevenagel condensation reaction is carried out under basic conditions to obtain compound (3). The obtained compound (3) and the acetoacetate compound undergo Michael addition and intramolecular Aldol condensation reaction under basic conditions to obtain compound (5). Compound (5) is subjected to oxidative aromatization to give compound (6). Compound (6) and (+) - trans - are subjected to -2-8 - alkylation to give compound (-1 -) under acidic conditions to mint Friedel, Crafts diene 8 alcohol. The finally obtained compound (8) is subjected to high-temperature hydrolysis decarboxylation to obtain the target compound cannabidiol (CBD) under an alkaline condition, and has the CBD) high reaction selectivity, no isomer formation, high total yield, less byproducts, easy purification of the product, low process cost and easy realization of industrial production.

Synthetic method of cannabidiol

The invention discloses a synthetic method of cannabidiol, wherein the synthetic method specifically comprises the steps: carrying out a coupling reaction on a raw material A and (1S,4R)-1-methyl-4-(1-methyl vinyl)-2-cyclohexene-1-ol under the catalysis of an acid catalyst to obtain an intermediate I or an intermediate II; converting hydroxyl in the intermediate II into a halide-like compound to obtain an intermediate III; and carrying out Suzuki coupling on the intermediate I or the intermediate III and pentyl boride to obtain the final product cannabidiol. The reaction system is simple, thereaction temperature is within 100 DEG C, the reaction conditions are easy to control, and large-scale production is easy; the cannabidiol intermediate prepared by the method disclosed by the invention can be recrystallized and purified by a conventional method, the yield is up to 86.5%, the purity is up to 98.7%, and the chemical purity and single impurity index requirements of the cannabidiol intermediate serving as a key intermediate of a crude drug can be met; the yield of the cannabidiol prepared by the method is as high as 80.7%, the purity is as high as 97%, the raw material indexes arecompletely met, and a new method and thought are provided for industrial production of the cannabidiol.

A Novel and Practical Continuous Flow Chemical Synthesis of Cannabidiol (CBD) and its CBDV and CBDB Analogues

Cannabidiol is one of the main non-psychoactive cannabinoids present in Cannabis sativa and, in the last decade, it is gaining great interest among the scientific community for its pharmaceutical, nutraceutical, and cosmetic applications. Herein, we report the first continuous flow chemical synthesis of cannabidiol (CBD) and its analogues cannabidivarin (CBDV) and cannabidibutol (CBDB). This approach permits to synthesize products in very good yields (55–59 %), limiting the formation of psychoactive and illegal cannabinoids such as tetrahydrocannabinol (THC).