64052-90-0

Usage

Uses

Used in Pharmaceutical Applications:
Beta-cannabispiranol is used as a therapeutic agent for its potential anti-inflammatory and anti-cancer properties. It may help in reducing inflammation and fighting cancer cells, offering new avenues for medical treatments.
Used in Aroma and Flavor Industry:
Beta-cannabispiranol is used as a flavoring agent and aromatic component in the cannabis industry to enhance the unique taste and scent of cannabis products, contributing to their overall appeal and consumer experience.
Used in Cannabis Strain Identification:
Beta-cannabispiranol is used as a chemical marker for distinguishing different cannabis strains based on their aroma profiles. This aids in the classification and selection of strains with desired characteristics for both medicinal and recreational purposes.

Upstream product

• 71135-79-0 cannabispiradienone-A 
• 76898-51-6 (+/-)-cannabispirenone-A 
• 880-87-5 5,7-dimethoxyindan-1-one 
• 76842-66-5 C₁₆H₂₀O₄ 
• 76842-65-4 rac-2',3'-dihydro-5',7'-dimethoxyspiro[cyclohex-2-ene-1,1'-[1H]inden]-4-one 
• 83088-36-2 5-methoxy-7-methoxyethoxymethyloxy-1-(3,3-ethylenedioxybutyl)indan-1-carbonitrile 
• 83088-39-5 5-methoxy-7-methoxyethoxymethyloxy-1-(3,3-ethylenedioxybutyl)indan-1-carbaldehyde 
• 76842-69-8 5-methoxy-7-methoxyethoxymethyloxyindan-1-spiro-1'-cyclohex-2'-en-4'-one 
• 83088-41-9 5-methoxy-7-methoxyethoxymethyloxy-1-(3-oxobutyl)indan-1-carbaldehyde 
• 76842-62-1 5,7-dimethoxy-1-(3,3-ethylenedioxybutyl)indan-1-carbonitrile 
• 76842-63-2 5,7-dimethoxy-1-(3,3-ethylenedioxybutyl)indan-1-carbaldehyde 
• 76842-72-3 5-methoxy-7-methoxyethoxymethyloxyindan-1-carbonitrile 
• 76842-64-3 5,7-dimethoxy-1-(3-oxobutyl)indan-1-carbaldehyde 
• 76842-74-5 O-methylcannabispiradienone 

Downstream Products

• 61262-81-5 cannabispirone 

Relevant academic research and scientific papers

Total Synthesis of the Spirans of Cannabis: Cannabispiradienone, Cannabispirenone-A and -B, Cannabispirone, α- and β-Cannabispiranols and the Dihydrophenanthrene Cannithrene-1

O-Methylcannabispirenone has been synthesised (57percent overall from 3,5-dimethoxycinnamic acid) via 5,7-dimethoxyindanone, p-tolylsulphonylmethyl isocyanide conversion into the 1-nitrile, alkylation with 1-iodo-3,3-ethylenedioxybutane, deacetalisation, and spirocyclisation. 5,7-Dimethoxyindanone is 7-deprotected by boron trichloride with high selectivity, and re-protected as the methoxyethoxymethyl ether: following the above route, finally deprotecting by boron trichloride, gives cannabispirenone-A (2) in 21percent overall yield.O-Methylcannabispirenone can be demethylated to give (2) by lithium 1,1-dimethylethanethiolate: demethylation with boron tribromide gives cannabispirenone-B (3).Hydrogenation of synthetic cannabispirenone-A gives cannabispirone (4), reduced by borohydride to the epimeric α-(6) and β-(5) cannabispiranols, separated by h.p.l.c.Dehydrogenation of O-methylcannabispirenone with dichlorodicyanobenzoquinone, followed by lithium 1,1-dimethylethanethiolate demethylation, gives cannabispiradienone (1).Under acidic conditions, the latter undergoes dienone-phenol rearrangement to give cannithrene-1 (8), thus completing the total synthesis of the spiro-cannabinoid group of natural products discussed in the preceding paper.The unsubstituted cannabispirenone parent has also been synthesised.

SYNTHESIS OF THE FIVE NATURAL CANNABIS SPIRANS

An efficient route to the O-protected spirenones (2c) and (2d) is described: from these, the five known natural spirans of cannabis, i.e. cannabispiradienone (1a), cannabispirenone-A (2a), cannabispirenone-B (2b), cannabispirone (3a) and cannabispiranol (4a), are synthesised.

Cannabis. XIII. Two new spiro-compounds, cannabispirol and acetyl cannabispirol

Two new spiro-compounds, cannabispirol and acetyl cannabispirol, were isolated along with cannabispirone and cannabispirenone from the Japanese domestic cannabis and these structures were elucidated. The biogenetic relationship of spiro-compounds and cannabinoids was also discussed.