11-Hydroxytetrahydrocannabinol

Base Information

• Chemical Name: 11-Hydroxytetrahydrocannabinol
• CAS No.: 36557-05-8
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.451
• European Community (EC) Number: 636-821-1,803-555-4
• UNII: 9VY04N5SLB
• DSSTox Substance ID: DTXSID50190061
• Nikkaji Number: J113.237G
• Wikipedia: 11-Hydroxy-THC
• Wikidata: Q722962
• Metabolomics Workbench ID: 73599
• ChEMBL ID: CHEMBL3229459
• Mol file: 36557-05-8.mol

Synonyms:11-hydroxy-delta(9)-tetrahydrocannabinol;11-hydroxy-delta(9)-tetrahydrocannabinol, (6aR-trans)-isomer;11-hydroxy-delta(9)-tetrahydrocannabinol, (trans)-isomer;11-hydroxy-delta(9)-THC;11-hydroxytetrahydrocannabinol;7-hydroxy-delta(1)-tetrahydrocannabinol

Chemical Property of 11-Hydroxytetrahydrocannabinol

Chemical Property:

• Vapor Pressure: 2.06E-08mmHg at 25°C
• Melting Point: 136-138°C
• Boiling Point: 437.1 °C at 760 mmHg
• PKA: 9.78±0.60(Predicted)
• Flash Point: 218.2 °C
• PSA: 49.69000
• Density: 1.071 g/cm³
• LogP: 4.70820
• Storage Temp.: −20°C
• XLogP3: 5.7
• 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:

99% ^*data from raw suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22-63
• Safety Statements: 36-45

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)CO)O
• Isomeric SMILES: CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)CO)O
• Uses: A metabolite of ?9-Tetrahydrocannabinol (?9-THC) (T293200).

Technology Process of 11-Hydroxytetrahydrocannabinol

There total 17 articles about 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: 94.0%

Acetic acid (6aR,10aR)-1-hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-9-ylmethyl ester → 11-hydroxy-Δ-9-tetrahydrocannabinol (36557-05-8,34675-49-5,362044-74-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1039/c39890000062

Reference yield: 54.0%

carbon dioxide (124-38-9,18923-20-1) + C35H52N2O4S (949595-94-2) → 11-nor-9-carboxt-Δ-9-tetrahydrocannabinol (36557-05-8,56354-06-4,64280-14-4,104874-50-2,114028-39-6,122797-75-5)

Guidance literature:

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In hexane; 1.) -78 deg C to 0 deg C, 30 min, 2.) 3 min;

DOI:10.1021/jo970969e

Reference yield:

(-)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol tert-butyldimethylsilyl ether (138285-38-8) → 11-nor-9-carboxt-Δ-9-tetrahydrocannabinol (36557-05-8,56354-06-4,64280-14-4,104874-50-2,114028-39-6,122797-75-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1055/s-1991-26590

upstream raw materials:

Olivetol

Acetic acid (R)-1-hydroxy-4-isopropenyl-cyclohex-2-enylmethyl ester

dronabinol

(-)-11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol tert-butyldimethylsilyl ether

Downstream raw materials:

C₂₅H₃₁NO₆

Refernces

• 1、 -. "TETRAHYDROCANNABINOID ANTIGENS AND METHOD OF USE". Page/Page column Figure 8. . Retrieved 2010/10/20.
• 2、 Siegel,Gordon,Razdan. "Studies on the synthesis of (-)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THC) and related compounds: An improved oxidative procedure". . p. 851 - 853. Retrieved 2007/10/02.