22972-55-0

Basic information

• Product Name: 4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL
• Synonyms: (e)-(-)-4-p-mentha-1,8-dien-3-yl-5-pentylresorcinol;8-dien-3-yl-5-pentyl-4-p-mentha-(-)-(e)-resorcino;ABN-CBD;4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL;1-Hydroxy-3-n-Pentylcannabidiol;4-(p-Mentha-1,8-dien-3-yl)-5-pentylresorcinol;Resorcinol, 4-p-mentha-1,8-dien-3-yl-5-pentyl-, (-)-(E)-
• CAS NO: 22972-55-0
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.46
• Product Categories: Cannabinoid receptor
• Mol File: 22972-55-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 446.4 °C at 760 mmHg
• Flash Point: 196.7 °C
• Appearance: Amber oil
• Density: 1.025 g/cm³
• Vapor Pressure: 1.39E-08mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: Desiccate at -20°C
• CAS DataBase Reference: 4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL(22972-55-0)
• EPA Substance Registry System: 4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL(22972-55-0)

Safety Data

• Hazardous Substances Data: 22972-55-0(Hazardous Substances Data)

Usage

Description

4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL is a complex organic compound characterized by its unique molecular structure. It is a derivative of benzenediol, featuring a cyclohexenyl and a pentyl group attached to its structure. 4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL holds potential for various applications across different industries due to its distinct chemical properties.

Uses

Used in Pharmaceutical Industry:
4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL is used as an active pharmaceutical ingredient for its potential therapeutic effects. The compound's unique structure may allow it to interact with specific biological targets, making it a candidate for the development of new drugs.
Used in Chemical Synthesis:
In the chemical industry, 4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL can be used as a key intermediate in the synthesis of more complex molecules. Its reactive functional groups make it a versatile building block for creating a variety of compounds with different applications.
Used in Material Science:
4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL may also find applications in material science, where its unique structure could be utilized to develop new materials with specific properties. These materials could have potential uses in various fields, such as electronics, coatings, or adhesives.
Used in Flavor and Fragrance Industry:
Due to its complex structure, 4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL could be used in the flavor and fragrance industry to create unique scents or flavors. Its chemical properties may allow it to contribute distinct sensory characteristics to various products.
Used in Research and Development:
The compound's unique structure and potential applications make it an interesting subject for research and development. Scientists and researchers may use 4-[(1R,6R)-3-METHYL-6-(1-METHYLETHENYL)-2-CYCLOHEXEN-1-YL]-5-PENTYL-1,3-BENZENEDIOL to study its properties, interactions, and potential uses in various fields.

Biological Activity

Neurobehaviorally inactive cannabinoid that acts as a selective agonist for GPR55 (EC 50 values are 2.5, >30 and >30 μ M at GPR55, CB 1 and CB 2 receptors respectively). Increases phosphorylation of protein kinases in, and migration of, human umbilical vein endothelial cells.

InChI:InChI=1/C21H30O2/c1-5-6-7-8-16-12-17(22)13-20(23)21(16)19-11-15(4)9-10-18(19)14(2)3/h11-13,18-19,22-23H,2,5-10H2,1,3-4H3/t18-,19+/m0/s1

Upstream product

• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 500-66-3 Olivetol 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 22972-51-6 (1S,4R)-p-mentha-2,8-dien-1-ol 
• 936-91-4 3-carene epoxide 
• 20053-58-1 (1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide 
• 1305300-50-8 1,5-bis(tert-butyldimethylsilyloxy)-2-(6-isopropenyl-3-methyl-2-cyclohexenyl)-3-pentylbenzene 
• 1305300-48-4 5-(4-bromobutyl)-3,5-bis(tert-butyldimethylsilyloxy)-2-(6-isopropenyl-3-methyl-2-cyclohexenyl)benzene 
• 1260669-54-2 5-(4-bromobutyl)-4-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-1,3-benzenediol 
• 1260669-57-5 4-(3,5-dihydroxyphenyl)-1-bromobutane 
• 111319-95-0 (5R)-2-methyl-5-(1-methylethenyl)-1,3-cyclohexadiene 
• 111540-03-5 4-(3,5-dimethoxyphenyl)-1-bromobutane 

Relevant articles and documents

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).

The preparation of [pentane-5,5,5-3H3]-abnormal- cannabidiol

A bromoalkane precursor was synthesized in six steps, and its copper catalysed coupling with methylmagnesium chloride to provide unlabelled abnormal-cannabidiol (1a) was optimized. The methodology was used for an analogous coupling using [3Hsu

Acid-catalysed Terpenylations of Olivetol in the Synthesis of Cannabinoids

Examination of the toluene-p-sulphonic acid-catalysed reaction of (1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide with olivetol shows that, inconsistently with the accepted mechanism, (3R,4R)-(-)-o- and -p-cannabidiols are produced as well as (3R,4R)-(-)-Δ1- and Δ6-tetrahydrocannabinols.Evidence is now presented that, as in Petrzilka's reaction employing chiral p-mentha-2,8-dien-1-ols, the reacting species is the delocalised (4R)-p-mentha-2,8-dien-1-yl cation (9).Similar terpenylation using (1S,3S,4R,6R)-(+)-trans-car-3-ene epoxide shows that besides the reported (-)-Δ6-THC, o- and p-cannabidiols, Δ1-THC and Δ4,8-iso-THC can also be produced.The nature of the products, the chirality, and the characteristics of the reaction implicate again the delocalised cation (9).Its formation via Kropp-type rearrangement is excluded and a pathway leading to (4R)-p-mentha-2,6,8-triene, which on protonation gives (9), is proposed.Protonated on C-8, the triene can be trapped and isolated as (4R)-p-mentha-2,6-dien-8-ol.The latter, made in (+/-)-form from citral, proved to be an excellent terpenylating agent for producing cannabinoids.Terpenylation of olivetol by the pinanes (1S,4S,5S)-(-)-cis-verbenol and (1R,5S,7R)-(+)-cis-chrysanthenol is compared.A major drawback of the latter is partial racemisation which occurs in the verbenone-chrysanthenone isomerisation during its photochemical preparation.Whilst Δ1-THC cannot be directly obtained from verbenol, its tertiary allylic cation permits a much higher yielding terpenylation than the secondary cation from chrysanthenol.