1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol

Base Information

• Chemical Name: 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol
• CAS No.: 112924-45-5
• Deprecated CAS: 182269-82-5
• Molecular Formula: C25H38O3
• Molecular Weight: 386.575
• European Community (EC) Number: 675-766-8
• UNII: R6VT8U5372
• DSSTox Substance ID: DTXSID40150235
• Nikkaji Number: J442.047K
• Wikipedia: Dexanabinol
• Wikidata: Q962504
• NCI Thesaurus Code: C99381
• Pharos Ligand ID: DXK64F6H31Z4
• Metabolomics Workbench ID: 149781
• ChEMBL ID: CHEMBL334533
• Mol file: 112924-45-5.mol

Synonyms:6H-Dibenzo[b,d]pyran-9-methanol,3-(1,1-dimethylheptyl)-6a,7,10,10a-tetrahydro-1-hydroxy-6,6-dimethyl-,(6aS-trans)-;Dexanabinol;HU 211;PRS 211007-000;Sinnabidiol;

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Chemical Property of 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol

Chemical Property:

• Vapor Pressure: 1.22E-09mmHg at 25°C
• Melting Point: 141-142°
• Refractive Index: 1.525
• Boiling Point: 470.1 °C at 760 mmHg
• PKA: 9.72±0.60(Predicted)
• Flash Point: 238.1 °C
• PSA: 49.69000
• Density: 1.03g/cm³
• LogP: 6.22350
• Storage Temp.: −20°C
• Solubility.: DMSO: soluble
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 386.28209507
• Heavy Atom Count: 28
• Complexity: 550

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC(C)(C)C1=CC(=C2C3CC(=CCC3C(OC2=C1)(C)C)CO)O
• Isomeric SMILES: CCCCCCC(C)(C)C1=CC(=C2[C@H]3CC(=CC[C@@H]3C(OC2=C1)(C)C)CO)O
• Recent ClinicalTrials: Dexanabinol in Patients With Brain Cancer

Technology Process of 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol

There total 20 articles about 1,1-Dimethylheptyl-11-hydroxytetrahydrocannabinol 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: 96.0%

dexanabinol pivalate (113449-78-8) → (6aS-trans)-6,6-dimethyl-3-(1,1-dimethylheptyl)-1-hydroxy-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran-9-methanol (112924-45-5)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1016/S0957-4166(00)86322-3

Reference yield:

5-(1',1'-dimethyl-n-heptyl)-1,3-dihydroxybenzene (56469-10-4) → dexanabinol (112924-45-5,137428-19-4,112830-95-2)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride etherate / CH₂Cl₂ / -20 °C

2: lithium aluminum hydride

With lithium aluminium tetrahydride; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/S0957-4166(00)86322-3

Reference yield:

(1R)-Myrtenol (19894-97-4) → dexanabinol (112924-45-5,137428-19-4,112830-95-2)

Guidance literature:

Multi-step reaction with 5 steps

2: sodium chromate / acetic acid; acetic anhydride / 72 h / 35 °C

3: lithium tri-tert-butoxyaluminohydride / tetrahydrofuran

4: boron trifluoride etherate / CH₂Cl₂ / -20 °C

5: lithium aluminum hydride

With lithium aluminium tetrahydride; sodium chromate(VI); lithium tri(t-butoxy)aluminum hydride; boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; acetic anhydride; acetic acid;

DOI:10.1016/S0957-4166(00)86322-3

upstream raw materials:

2,2-Dimethyl-propionic acid (6aR,10aR)-3-(1,1-dimethyl-heptyl)-1-hydroxy-6,6-dimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-9-ylmethyl ester

5-(1',1'-dimethyl-n-heptyl)-1,3-dihydroxybenzene

(1R)-Myrtenol

(1R,5S)-2-[(2,2-dimethylpropoyloxy)methyl]-6,6-dimethylbicyclo[3.1.1]hept-2-ene

Downstream raw materials:

[3H]-HU 243

Refernces

• 1、 -. "High enantiomeric purity dexanabinol for pharmaceutical compositions". Page/Page column 10. . Retrieved 2010/02/07.
• 2、 Mechoulam,Breuer,Feigenbaum,Devane. "Nonpsychotropic synthetic cannabinoids as therapeutic agents". . p. 267 - 276. Retrieved 2007/10/02.