8,9-Dihydrocannabidiol

Base Information

• Chemical Name: 8,9-Dihydrocannabidiol
• CAS No.: 877660-90-7
• Molecular Formula: C21H32O2
• Molecular Weight: 316.484
• UNII: K2X8KX5UDK
• DSSTox Substance ID: DTXSID501132586
• Wikidata: Q66311060
• Wikipedia: 8,9-Dihydrocannabidiol
• Mol file: 877660-90-7.mol

Synonyms:8,9-dihydrocannabidiol;877660-90-7;K2X8KX5UDK;SCHEMBL13626352;DTXSID501132586;PDSP2_000228;PD167687;Q66311060;1,3-Benzenediol, 2-[(1S,6S)-3-methyl-6-(1-methylethyl)-2-cyclohexen-1-yl]-5-pentyl-;2-((1S,6S)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-yl)-5-pentyl-1,3-benzenediol;(1'S,2'S)-2'-isopropyl-5'-methyl-4-pentyl-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol

Chemical Property of 8,9-Dihydrocannabidiol

Chemical Property:

• XLogP3: 6.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 316.240230259
• Heavy Atom Count: 23
• Complexity: 375

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• 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

Technology Process of 8,9-Dihydrocannabidiol

There total 13 articles about 8,9-Dihydrocannabidiol 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: 97.5%

CBD (13956-29-1,521-37-9) → (-)-(1'S,2'S)-2'-isopropyl-5'-methyl-4-pentyl-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol (877660-90-7)

Guidance literature:

With hydrogen; platinum; In ethyl acetate; for 0.5h; under 517.162 Torr;

Reference yield: 60.0%

Phosphoric acid (5R,6R)-6-(2,6-dimethoxy-4-pentyl-phenyl)-5-isopropenyl-2-methyl-cyclohex-1-enyl ester diethyl ester (140633-48-3) → (-)-(1'S,2'S)-2'-isopropyl-5'-methyl-4-pentyl-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol (877660-90-7)

Guidance literature:

With lithium; ethylamine; In tetrahydrofuran; tert-butyl alcohol; at 0 ℃;

DOI:10.1021/jo00039a022

Reference yield: 48.0%

(1S,4S)-4-isopropyl-1-methyl-2-cyclohexen-1-ol (117556-62-4) + Olivetol (500-66-3) → (-)-(1'S,2'S)-2'-isopropyl-5'-methyl-4-pentyl-1',2',3',4'-tetrahydro-[1,1'-biphenyl]-2,6-diol (877660-90-7)

Guidance literature:

With silver(I) bis(trifluoromethanesulfonyl)imide; In 1,2-dichloro-ethane; at 20 ℃; Inert atmosphere; Darkness;

DOI:10.1021/acs.joc.1c02571

upstream raw materials:

Phosphoric acid (5R,6R)-6-(2,6-dimethoxy-4-pentyl-phenyl)-5-isopropenyl-2-methyl-cyclohex-1-enyl ester diethyl ester

(R)-(-)-α-phellandren-8-ol

Olivetol

3-endo-9-dibromo-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one

Downstream raw materials:

(-)-8,9-dihydro-CBD diacetate

(-)-8,9-dihydro-CBD-7-oic acid diacetate

(-)-8,9-dihydro-CBD-7-oic acid

Refernces

• 1、 Seccamani, Paolo,Franco, Chiara,Protti, Stefano,Porta, Alessio,Profumo, Antonella,Caprioglio, Diego,Salamone, Stefano,Mannucci, Barbara,Merli, Daniele. "Photochemistry of Cannabidiol (CBD) Revised. A Combined Preparative and Spectrometric Investigation". supporting information. p. 2858 - 2865. Retrieved 2021/11/12.
• 2、 -. "PROCESS FOR THE SYNTHESIS OF CANNABIDIOL AND INTERMEDIATES THEREOF". . . Retrieved 2021/09/17.