69636-83-5

Basic information

• Product Name: α-Cannabispiranol
• Synonyms: α-Cannabispiranol;alpha-Cannabispiranol;trans-2',3'-Dihydro-5'-methoxyspiro[cyclohexane-1,1'-[1H]indene]-4,7'-diol
• CAS NO: 69636-83-5
• Molecular Formula: C15H20O3
• Molecular Weight: 248.3175
• Mol File: 69636-83-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: α-Cannabispiranol(CAS DataBase Reference)
• NIST Chemistry Reference: α-Cannabispiranol(69636-83-5)
• EPA Substance Registry System: α-Cannabispiranol(69636-83-5)

Safety Data

• Hazardous Substances Data: 69636-83-5(Hazardous Substances Data)

Usage

General Description

α-Cannabispiranol is a unique chemical compound isolated from the cannabis plant. It is a phytocannabinoid that has been found to possess potential pharmacological effects, particularly in its ability to activate cannabinoid receptors in the body. α-Cannabispiranol has been studied for its potential as a therapeutic agent, showing promise in treating conditions such as pain, inflammation, and mood disorders. Its structure and activity suggest that it may have a role in the medicinal properties of cannabis, and further research is needed to fully understand its potential benefits and safety profile. Overall, α-Cannabispiranol represents an important area of research in the study of cannabinoids and their potential applications in medicine.

Upstream product

• 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 
• 76842-71-2 5-methoxy-7-methoxyethoxymethyloxyindan-1-one 
• 76842-61-0 5,7-dimethoxyindan-1-carbonitrile 
• 76842-70-1 7-hydroxy-5-methoxy-2,3-dihydro-1H-inden-1-one 

Relevant articles and documents

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.

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.