11-Nor-9-carboxy-delta-9-tetrahydrocannabinol

Base Information

• Chemical Name: 11-Nor-9-carboxy-delta-9-tetrahydrocannabinol
• CAS No.: 56354-06-4
• Molecular Formula: C21H28 O4
• Molecular Weight: 344.451
• European Community (EC) Number: 690-035-3
• UNII: 4TPC9E4A32
• DSSTox Substance ID: DTXSID20204907,DTXSID701344925
• Nikkaji Number: J356.101A
• Wikipedia: 11-Nor-9-carboxy-THC
• Wikidata: Q27146854
• ChEMBL ID: CHEMBL3263381
• Mol file: 56354-06-4.mol

Synonyms:(6aR-trans)-isomer of 11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid;11-nor-9-carboxy-delta(9)-tetrahydrocannabinol;11-nor-9-carboxy-delta-9-tetrahydrocannabinol;11-nor-9-carboxy-THC;11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid;delta(1)-tetrahydrocannabinol-7-oic acid;delta(9)-tetrahydrocannabinol-11-oic-acid;delta-9-11-carboxytetrahydrocannabinol;hexadeutero-11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid;tetrahydrocannabinol-7-oic acid;THC-11-oic acid

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of 11-Nor-9-carboxy-delta-9-tetrahydrocannabinol

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.62E-09mmHg at 25°C
• Melting Point: 211
• Boiling Point: 466.9 °C at 760 mmHg
• PKA: 4.66±0.40(Predicted)
• Flash Point: 158.1 °C
• PSA: 66.76000
• Density: 1.14 g/cm³
• LogP: 4.80050
• Storage Temp.: −20°C
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 344.19875937
• Heavy Atom Count: 25
• Complexity: 524

Purity/Quality:

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC1=CC(=C2C3C=C(CCC3C(OC2=C1)(C)C)C(=O)O)O
• Isomeric SMILES: CCCCCC1=CC(=C2[C@@H]3C=C(CC[C@H]3C(OC2=C1)(C)C)C(=O)O)O

Technology Process of 11-Nor-9-carboxy-delta-9-tetrahydrocannabinol

There total 12 articles about 11-Nor-9-carboxy-delta-9-tetrahydrocannabinol 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: 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

Reference yield:

(-)-9-Nor-9-oxohexahydrocannabinol (52195-11-6) → 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:

Multi-step reaction with 2 steps

1: ethanol / 0.08 h / 27 °C

2: 54 percent / n-BuLi, TMEDA / hexane / 1.) -78 deg C to 0 deg C, 30 min, 2.) 3 min

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; In ethanol; hexane;

DOI:10.1021/jo970969e

upstream raw materials:

dronabinol

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

carbon dioxide

C₃₅H₅₂N₂O₄S

Downstream raw materials:

C₂₅H₃₁NO₆

Δ⁹-Tetrahydrocannabinol-11-oic acid glucuronide