11-Hydroxy-delta(8)-thc

Base Information

• Chemical Name: 11-Hydroxy-delta(8)-thc
• CAS No.: 25952-85-6
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.467
• DSSTox Substance ID: DTXSID70948864
• Wikidata: Q82926694
• ChEMBL ID: CHEMBL3277903
• Mol file: 25952-85-6.mol

Synonyms:11-hydroxy-delta(8)-tetrahydrocannabinol;11-hydroxy-delta(8)-tetrahydrocannabinol, (6aR-trans)-isomer;11-hydroxy-delta(8)-THC

Chemical Property of 11-Hydroxy-delta(8)-thc

Chemical Property:

• Vapor Pressure: 3.77E-08mmHg at 25°C
• Boiling Point: 429.8°C at 760 mmHg
• Flash Point: 213.7°C
• PSA: 49.69000
• Density: 1.071g/cm³
• LogP: 4.70820
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 330.21949481
• Heavy Atom Count: 24
• Complexity: 456

Purity/Quality:

11-HYDROXY-DELTA(8)-TETRAHYDROCANNABINOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=CC(=C2C3CC(=CCC3C(OC2=C1)(C)C)CO)O

Technology Process of 11-Hydroxy-delta(8)-thc

There total 8 articles about 11-Hydroxy-delta(8)-thc 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: 88.0%

11-oxo-6a,10a-trans-Δ8-THC (53865-18-2,83944-93-8) → 11-hydroxy-6a,10a-trans-Δ8-THC (25952-85-6,28646-40-4,83944-94-9,113301-07-8,25952-63-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Ambient temperature;

DOI:10.1139/v82-403

Reference yield:

4-(1-hydroxy-1-methylethyl)-1-methoxy-1,4-cyclohexadiene (61597-37-3) → 11-hydroxy-6a,10a-trans-Δ8-THC (25952-85-6,28646-40-4,83944-94-9,113301-07-8,25952-63-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 24 percent / water, stannic chloride / CH₂Cl₂ / 7 h / 0 °C

2: 58 percent / aluminium chloride / CH₂Cl₂ / 5 h / Ambient temperature

3: 1) benzyltriethylammonium chloride, aq. sodium hydroxide; 2) magnesium bromide / 1) acetonitrile, 2 h; 2) THF, 2 d, r.t.

4: 90 percent / lithium carbonate, lithium bromide (0.50 mmol) / dimethylformamide / 6 h / 100 °C

5: 88 percent / lithium aluminium hydride / tetrahydrofuran / 3 h / Ambient temperature

With sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; N-benzyl-N,N,N-triethylammonium chloride; water; tin(IV) chloride; lithium carbonate; lithium bromide; magnesium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1139/v82-403

Reference yield:

11-nor-9-keto-6a,10a-cis-HHC (6616-69-9,16964-48-0,16964-51-5,52195-11-6,60761-09-3,63790-37-4,138383-58-1) → 11-hydroxy-6a,10a-trans-Δ8-THC (25952-85-6,28646-40-4,83944-94-9,113301-07-8,25952-63-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 58 percent / aluminium chloride / CH₂Cl₂ / 5 h / Ambient temperature

2: 1) benzyltriethylammonium chloride, aq. sodium hydroxide; 2) magnesium bromide / 1) acetonitrile, 2 h; 2) THF, 2 d, r.t.

3: 90 percent / lithium carbonate, lithium bromide (0.50 mmol) / dimethylformamide / 6 h / 100 °C

4: 88 percent / lithium aluminium hydride / tetrahydrofuran / 3 h / Ambient temperature

With sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; N-benzyl-N,N,N-triethylammonium chloride; lithium carbonate; lithium bromide; magnesium bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1139/v82-403

upstream raw materials:

11-oxo-6a,10a-trans-Δ⁸-THC

4-(1-hydroxy-1-methylethyl)-1-methoxy-1,4-cyclohexadiene

11-nor-9-keto-6a,10a-cis-HHC

dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on

Refernces

• 1、 Nilsson,Nilsson,Agurell. "Metabolism of cannabis. XI. Synthesis of -tetra-hydrocannabinol and 7-hydroxy-tetrahydrocannabinol.". . p. 768 - 769. Retrieved 2007/10/10.