64280-14-4

Basic information

• Product Name: DL-11-NOR-9-CARBOXY-DELTA-9-THC
• Synonyms: NOR-9-CARBOXY-DELTA 9 THC, (+,-)-11-;DL-11-NOR-9-CARBOXY-DELTA-9-THC;11-Nor-9-carboxy-thc;1-Hydroxy-6,6-dimethyl-3-pentyl-6A,7,8,10A-tetrahydro-6H-dibenzo(B,D)pyran-9-carboxylic acid;6H-Dibenzo(B,D)pyran-9-carboxylic acid, 6A,7,8,10A-tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-;delta(1)-Tetrahydrocannabinol-7-oic acid;delta(9)-Tetrahydrocannabinol-11-oic-acid;delta-9-11-Carboxytetrahydrocannabinol
• CAS NO: 64280-14-4
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 344.44
• Mol File: 64280-14-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 466.9°Cat760mmHg
• Flash Point: 158.1°C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 1.62E-09mmHg at 25°C
• Refractive Index: 1.554
• CAS DataBase Reference: DL-11-NOR-9-CARBOXY-DELTA-9-THC(CAS DataBase Reference)
• NIST Chemistry Reference: DL-11-NOR-9-CARBOXY-DELTA-9-THC(64280-14-4)
• EPA Substance Registry System: DL-11-NOR-9-CARBOXY-DELTA-9-THC(64280-14-4)

Safety Data

• Hazardous Substances Data: 64280-14-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C21H28O4/c1-4-5-6-7-13-10-17(22)19-15-12-14(20(23)24)8-9-16(15)21(2,3)25-18(19)11-13/h10-12,15-16,22H,4-9H2,1-3H3,(H,23,24)

Upstream product

• 123408-92-4 (6aR,10aR)-9-[1,3]Dithian-2-yl-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 138285-36-6 (-)-11-oxo-Δ⁹-tetrahydrocannabinol tert-butyldimethylsilyl ether 
• 52663-85-1 (6aR,10aR)-1-Hydroxy-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromene-9-carbaldehyde 
• 124588-22-3 [(6aR,10aR)-1-(tert-Butyl-dimethyl-silanyloxy)-6,6-dimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-9-yl]-methanol 
• 6616-69-9 dl-6aα,7,10,10aα-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9(8H)-on 
• 52195-11-6 (-)-9-Nor-9-oxohexahydrocannabinol 
• 124-38-9 carbon dioxide 
• 949595-94-2 C₃₅H₅₂N₂O₄S 
• 138285-38-8 (-)-11-nor-9-carboxy-Δ⁹-tetrahydrocannabinol tert-butyldimethylsilyl ether 
• 1972-08-3 dronabinol 

Downstream Products

• 848242-78-4 C₂₅H₃₁NO₆ 

Relevant articles and documents

A concise methodology for the synthesis of (-)-Δ9-tetrahydrocannabinol and (-)-Δ9-tetrahydrocannabivarin metabolites and their regiospecifically deuterated analogs

The availability of tetrahydrocannabinols (Δ9-THC), tetrahydrocannabivarins (Δ9-THCV), and their metabolites in both their undeuterated and deuterated forms is critical for the analysis of biological and toxicological samples. We report here a concise methodology for the syntheses of (-)-Δ9-THC and (-)-Δ9-THCV metabolites in significantly improved overall yields using commercially available starting materials. Our approach allowed us to obtain the key intermediates (6aR,10aR)-9-nor-9-oxo-hexahydrocannabinols in four steps from (+)-(1R)-nopinone. This was followed by an optimized Shapiro reaction to give the (-)-11-nor-9-carboxy-metabolites, which were converted to their respective (-)-11-hydroxy analogs. The synthetic sequence involves a minimum number of steps, avoids undesirable oxidative conditions, and incorporates the costly deuterated resorcinols near the end of the synthetic sequence. This methodology enabled us to synthesize eight regiospecifically deuterated (-)-Δ9-THC and (-)-Δ9-THCV metabolites in a preparative scale and high optical purity without deuterium scrambling or loss.

Preparation of Racemic, (-)- And (+)-11-Nor-δ9-Tetrahydrocannabinol-9-carboxylic Acid

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A convenient synthesis of (-)-11-nor-Δ9-tetrahydrocannabinol-9-methanol

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