Cannabidiol

Base Information

• Chemical Name: Cannabidiol
• CAS No.: 13956-29-1
• Deprecated CAS: 35542-48-4,18436-46-9,20547-66-4,521-37-9
• Molecular Formula: C21H30 O2
• Molecular Weight: 314.468
• European Community (EC) Number: 689-176-3
• UNII: 19GBJ60SN5
• DSSTox Substance ID: DTXSID00871959,DTXSID301038839
• Nikkaji Number: J10.356J
• Wikipedia: Cannabidiol
• Wikidata: Q422917
• NCI Thesaurus Code: C118452
• RXCUI: 2045371
• Pharos Ligand ID: MFUZD2HFWKAA
• Metabolomics Workbench ID: 152117
• ChEMBL ID: CHEMBL190461
• Mol file: 13956-29-1.mol

Synonyms:1,3-Benzenediol, 2-(3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-yl)-5-pentyl-, (1R-trans)-;Cannabidiol;Epidiolex

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Chemical Property of Cannabidiol

Chemical Property:

• Vapor Pressure: 3.14E-09mmHg at 25°C
• Melting Point: 62-63°C
• Refractive Index: nD20 1.5404
• Boiling Point: 463.9 °C at 760 mmHg
• Flash Point: 206.3 °C
• PSA: 40.46000
• Density: 1.025 g/cm³
• LogP: 5.84650
• Storage Temp.: 2-8°C
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 414

Purity/Quality:

Safty Information:

• Pictogram(s): FT
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 36/37-45-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Anticonvulsants
• Canonical SMILES: CCCCCC1=CC(=C(C(=C1)O)C2C=C(CCC2C(=C)C)C)O
• Isomeric SMILES: CCCCCC1=CC(=C(C(=C1)O)[C@@H]2C=C(CC[C@H]2C(=C)C)C)O
• Recent ClinicalTrials: Cannabidiol for Bipolar Depression (CBD-BD)
• Recent EU Clinical Trials: Pilot study on the effect of cannabinoids THC + CBD on resistant spasticity in patients with chronic spinal cord injury.
• General Description: Cannabidiol (CBD) is a nonpsychotropic compound derived from cannabis, notable for its lack of binding to psychoactive receptors, distinguishing it from Δ9-tetrahydrocannabinol (Δ9-THC). It exhibits therapeutic potential and can be synthesized through methods such as nickel-catalyzed allylation, achieving high regioselectivity and yield. CBD and its analogues, including metabolites like 7-hydroxy-CBD, are of interest for their pharmacological properties, with synthetic pathways enabling modifications such as extended alkenyl side chains.

Technology Process of Cannabidiol

There total 129 articles about Cannabidiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(1′R,2′R)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl bis(2,2-dimethylpropanoate) → CBD (13956-29-1,521-37-9)

Guidance literature:

With methylmagnesium bromide; In diethyl ether; toluene; at 110 ℃; for 12h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;

DOI:10.1021/acs.joc.9b02880

Reference yield: 97.0%

O-2797 (1242-67-7,22198-90-9) → CBD (13956-29-1,521-37-9)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 ℃; for 2h; Solvent;

Reference yield: 94.0%

C30H47NO4 → CBD (13956-29-1,521-37-9)

Guidance literature:

With sodium hydroxide; In methanol; at 90 ℃; for 4h; Inert atmosphere;

upstream raw materials:

(+)-p-mentha-2,8-dien-1-ol

Olivetol

(+)-limonene oxide

diphenyl sulfide

Downstream raw materials:

(6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol

(-)-bis-O-(3.5-dinitro-benzoyl)-cannabidiol

(1′R,2′R)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl diacetate

C₃₃H₅₂N₂O₆

Refernces

Synthesis of cannabidiols via alkenylation of cyclohexenyl monoacetate

10.1021/ol060692h

The research focuses on developing a method to synthesize cannabidiol (CBD) and its analogues. The study highlights the potential of CBD as a nonpsychotropic drug due to its lack of binding to receptors responsible for psychoactivity, unlike ?9-tetrahydrocannabinol (?9-THC). The key reaction involves nickel-catalyzed allylation of 2-cyclohexene-1,4-diol monoacetate using a new reagent system, (alkenyl)ZnCl/TMEDA, achieving 94% regioselectivity and good yield. This method allows for the synthesis of CBD and its analogues, including those with longer alkenyl side chains. The research also explores the synthesis of metabolites like 7-hydroxy-CBD and demonstrates the transformation of synthesized compounds into CBD and ?9-THC. Chemicals such as lithium isopropenyl borate, alkenyl Grignard reagents, and various metal catalysts (e.g., NiCl2(tpp)2) play crucial roles in achieving the desired products with high regioselectivity and yield.