2808-33-5

Usage

InChI:InChI=1/C21H32O2/c1-5-6-7-11-18-14-20(22)19(21(23)15-18)13-12-17(4)10-8-9-16(2)3/h9,12,14-15,22-23H,5-8,10-11,13H2,1-4H3/b17-12+

Upstream product

• 106-24-1 Geraniol 
• 500-66-3 Olivetol 
• 106-25-2 Nerol 
• 6138-90-5 trans-geranyl bromide 
• 2808-41-5 Cannabigerolinsaeure-methylester 
• 58016-28-7 methyl 2,6-dihydroxy-6-pentylbenzoate 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 108-73-6 3,5-dihydroxyphenol 
• 308796-10-3 (1-pentyl)zinc(II) bromide 
• 94450-80-3 1,3-Bis(methoxymethoxy)-5-pentylbenzene 
• 25555-57-1 CBGA 

Downstream Products

• 25555-57-1 CBGA 
• 1040411-87-7 C₂₅H₃₆O₄ 

Relevant academic research and scientific papers

PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

METHODS OF SYNTHESIZING CANNABIGERGOL, CANNABIGEROLIC ACID, AND ANALOGS THEREOF

Disclosed are methods for preparing carmabigerol (CBG) or a CBG analog, embodiments of the method comprising providing a compound (I); combining the compound (I) with geraniol and a solvent to form a reaction mixture; and combining the reaction mixture with an acid catalyst to form a product mixture comprising CBG or the CBG analog. The method may further comprise separating the CBG or the CBG analog for the product mixture and may further comprise purifying the CBG or CBG analog. Methods for preparing cannabigerolic acid (CBGA) or a CBGA analog are also disclosed. The present disclosure also provides high purity CBG, CBGA and analogs thereof. CBG can be useful as a neuroprotectant, an antibacterial agent, etc.

PREPARING AND MODIFYING MEROTERPENE POLYKETIDES, KETONES, AND LACTONES FOR CANNABINOID SEMISYNTHESIS

Provided herein are processes, including semi-synthetic, and synthetic processes for preparing cannabinoids, and cannabinoid compositions provided thereby.

Syntheses of Amorfrutins and Derivatives via Tandem Diels-Alder and Anionic Cascade Approaches

We describe two complementary approaches based on a convergent [4+2] logic toward the synthesis of amorfrutins, cannabinoids, and related plant metabolites. An anionic cascade cyclization employing β-methoxycrotonates and β-chloro-α,β-unsaturated esters yielded amorfrutins in four linear steps and demonstrated utility of β-alkoxycrotonate-derived nucleophiles as functional equivalents of β-ketoester-derived dianions. Analogously, tandem Diels-Alder/retro-Diels-Alder cycloaddition of dimedone-derived bis(trimethylsiloxy)-dienes and α,β-alkynyl ester dienophiles provided facile access to resorcinol precursors of amorfrutins and cannabinoids, avoiding late-stage installation of prenyl or geranyl moieties as in previous approaches.

CATALYTIC CANNABIGEROL PROCESSES AND PRECURSORS

The present disclosure relates to cannabigerol sulfonate esters and processes for their use to prepare cannabigerol (CBG) and related compounds, including cannabigerobutol (CBGB), cannabigerovarin (CBGV), and cannabigerophorbol (CBGP). In a preferred embodiment, the cannabigerol sulfonate ester is (E)-4-(3, 7-5 dimethylocta-2,6-dienyl)-3,5-bis(trimetbylsilyloxy)phenyl trifluoromethanesulfonate. In a preferred process, the trifluoromethansulfonate leaving group is replaced by an alkyl group. The disclosure also relates to the use of catalysts and catalytic processes for the preparation of cannabigerol and related compounds from the cannabigerol sulfonate esters.

PROCESS FOR THE PRODUCTION OF CANNABINOIDS AND CANNABINOID ACIDS

The present invention relates to a process for the preparation of diverse known and novel cannabinoids 5, which include cannabigerol (CBG, 1), cannabigerolic acid (CBGA, 2), cannabigerovarin (CBGV, 3), cannabigerovarinic acid (CBGVA, 4) and other naturally occurring monocyclic cannabinoids and other analogues from simple inexpensive starting materials using a cascade sequence of allylic rearrangement and aromatization. Novel cannabinoids of series 5 are also claimed as part of the invention. These synthesized cannabinoids, unlike the minor cannabinoids isolated from Cannabis saliva or synthesized from the condensation reactions such as the reactions of substituted resorcinols with monoterpenes, are much easier to obtain at high purity levels. In particular, these cannabinoids, including but not limited to cannabigerol (CBG, 1), cannabigerolic acid (CBGA, 2), cannabigerovarin (CBGV, 3) and cannabigerovarinic acid (CBGVA, 4) are obtained without contamination with impurities with variation in RA and RB (e.g. contamination of CBG with CBGV).

Uncovering the Hidden Antibiotic Potential of Cannabis

The spread of antimicrobial resistance continues to be a priority health concern worldwide, necessitating the exploration of alternative therapies. Cannabis sativa has long been known to contain antibacterial cannabinoids, but their potential to address antibiotic resistance has only been superficially investigated. Here, we show that cannabinoids exhibit antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA), inhibit its ability to form biofilms, and eradicate preformed biofilms and stationary phase cells persistent to antibiotics. We show that the mechanism of action of cannabigerol is through targeting the cytoplasmic membrane of Gram-positive bacteria and demonstrate in vivo efficacy of cannabigerol in a murine systemic infection model caused by MRSA. We also show that cannabinoids are effective against Gram-negative organisms whose outer membrane is permeabilized, where cannabigerol acts on the inner membrane. Finally, we demonstrate that cannabinoids work in combination with polymyxin B against multidrug resistant Gram-negative pathogens, revealing the broad-spectrum therapeutic potential for cannabinoids.

SYNTHESIS OF CANNABIGEROL

Multiple methods of synthesizing cannabigerol are presented. Combining olivetol with geraniol derivatives are provided. Cross-coupling methods of combing functionalized resorcinols are provided. Useful intermediates are formed during such cross-coupling steps.

Efficient synthesis of cannabigerol, grifolin, and piperogalin via alumina-promoted allylation

The synthesis of three phenolic natural products has been accomplished with unprecedented efficiency using a new alumina-promoted regioselective aromatic allylation reaction. Cannabigerol and grifolin were prepared in one step from the inexpensive 5-alkyl-resorcinols olivetol and orcinol. Piperogalin was synthesized, for the first time, via two sequential allylations of orcinol with geraniol and prenol.

SYNTHESIS AND PURIFICATION OF CANNABIGEROL AND ITS APPLICATION

The present invention relates to a method for producing cannabigerol and purifying it from a reaction mixture. The present invention also relates to the cosmetic use of cannabigerol for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, in particular for reducing pigmentation of the skin, preferably for the improvement of the appearance of the skin in case of hyperpigmentation, lentigo or vitiligo. Furthermore, the present invention relates to cannabigerol for use in a therapeutic method for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, preferably for use in a therapeutic method for the treatment and/or prevention of malign skin disorders, in particular skin cancer.