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

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

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

• 22972-51-6 (1S,4R)-p-mentha-2,8-dien-1-ol 
• 500-66-3 Olivetol 
• 20053-58-1 (1S,2S,3R,6R)-(+)-trans-car-2-ene epoxide 
• 936-91-4 3-carene epoxide 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 22976-40-5 1,3-dimethoxy-5-pentylbenzene 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 1260669-57-5 4-(3,5-dihydroxyphenyl)-1-bromobutane 
• 1260669-54-2 5-(4-bromobutyl)-4-[(1R,6R)-3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl]-1,3-benzenediol 
• 1305300-48-4 5-(4-bromobutyl)-3,5-bis(tert-butyldimethylsilyloxy)-2-(6-isopropenyl-3-methyl-2-cyclohexenyl)benzene 
• 1305300-50-8 1,5-bis(tert-butyldimethylsilyloxy)-2-(6-isopropenyl-3-methyl-2-cyclohexenyl)-3-pentylbenzene 
• 107153-18-4 4-(3,5-dimethoxyphenyl)-1-butanol 
• 111540-02-4 1-(but-3-en-1-yl)-3,5-dimethoxybenzene 

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).

ONE-STEP FLOW-MEDIATED SYNTHESIS OF CANNABIDIOL (CBD) AND DERIVATIVES

Herein are described apparatus and processes for the preparation of cannabinoids, such as cannabidiol (CBD) and derivatives thereof. The apparatus and processes described can be used for the one-step, flow-mediated synthesis of cannabidiol and derivatives with improved overall yield, material throughput, and product purity relative to batch processes.

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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

Tetrahydrocannabinol revisited: Synthetic approaches utilizing molybdenum catalysts

Δ9-Tetrahydrocannabinol 1 and its isomers were synthesized via domino-type methodology. The first approach, leading to (±)-1, relies on the Mo(IV)-catalyzed, one-pot cascade reaction of citral (4) with olivetol (15), affording (±)-Δ9-tetrahydrocannabinol as a 69 : 31 mixture of the trans-(natural) and cis-isomers in 20% yield. The alternative approach, leading to natural (-)-1, commenced with epoxidation of (+)-limonene (R)-(+)-16; opening of the resulting cis-epoxide 17 with PhSeNa, followed by elimination, afforded tertiary alcohol 21, whose acetate 22 was treated with olivetol 15 in the presence of Mo(II) catalyst IV to afford (-)-1 in 52% yield.

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.

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