56354-06-4

Basic information

• Product Name: (-)-11-NOR-9-CARBOXY-DELTA9-THC
• Synonyms: (-)-11-NOR-9-CARBOXY-DELTA9-THC;11-nor-D9-tetrahydrocannabinol-9-*carboxylic acid;11-nor-delta9-tetrahydrocannabinol-9-*carboxylic;11-NOR-D9-TETRAHYDROCANNABINOL-9- CARBOX;11-NOR-DELTA9-TETRAHYDROCANNABINOL-9-*CA RBOXYLIC AC;11-nor-delta(sup 9)-tetrahydrocannabinol-9-carboxylic acid;11-Nor-Δ9-tetrahydrocannabinol-9-carboxylic acid solution;11-Nor-Δ9-tetrahydrocannabinol-9-carboxylic acid
• CAS NO: 56354-06-4
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 348.43
• EINECS: 200-659-6
• Product Categories: Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Isotope Labelled Compounds
• Mol File: 56354-06-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 206-209 °C
• Boiling Point: 466.9 °C at 760 mmHg
• Flash Point: 11 °C
• Appearance: /vacuum-dried powder
• Density: 1.14 g/cm³
• Vapor Pressure: 1.62E-09mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: −20°C
• PKA: 4.66±0.40(Predicted)
• CAS DataBase Reference: (-)-11-NOR-9-CARBOXY-DELTA9-THC(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-11-NOR-9-CARBOXY-DELTA9-THC(56354-06-4)
• EPA Substance Registry System: (-)-11-NOR-9-CARBOXY-DELTA9-THC(56354-06-4)

Safety Data

• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45-7
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 56354-06-4(Hazardous Substances Data)

Usage

Description

(-)-11-NOR-9-CARBOXY-DELTA9-THC, also known as a phytocannabinoid, is a derivative of Delta9-tetrahydrocannabinol (THC) in which the C-11 methyl group has been fully oxidized to a carboxy group. It is a further enzymatic oxidation product of 11-hydroxy-Delta9-tetrahydrocannabinol. (-)-11-NOR-9-CARBOXY-DELTA9-THC is found in the cannabis plant and has potential applications in various industries due to its unique properties.

Uses

Used in Pharmaceutical Industry:
(-)-11-NOR-9-CARBOXY-DELTA9-THC is used as a therapeutic agent for various medical conditions. Its application in the pharmaceutical industry is due to its potential to modulate the endocannabinoid system, which plays a role in regulating various physiological processes such as pain, mood, and appetite. (-)-11-NOR-9-CARBOXY-DELTA9-THC may offer relief for patients suffering from chronic pain, anxiety, and other conditions that can be alleviated by targeting the endocannabinoid system.
Used in Cosmetic Industry:
In the cosmetic industry, (-)-11-NOR-9-CARBOXY-DELTA9-THC is used as an active ingredient in skincare and hair care products. Its application in this industry is due to its potential anti-inflammatory and antioxidant properties, which can help soothe irritated skin, reduce redness, and promote overall skin health. Additionally, it may contribute to hair growth and improve hair health by targeting the endocannabinoid receptors present in the scalp.
Used in Research and Development:
(-)-11-NOR-9-CARBOXY-DELTA9-THC is also used as a research compound for studying the effects of cannabinoids on the human body. Its application in research and development is due to its unique structure and potential to provide insights into the endocannabinoid system's role in various physiological processes. (-)-11-NOR-9-CARBOXY-DELTA9-THC can be used to develop new drugs and therapies targeting the endocannabinoid system for a wide range of medical conditions.

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)/t15-,16-/m1/s1

Upstream product

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

Downstream Products

• 848242-78-4 C₂₅H₃₁NO₆ 
• 1362113-32-3 Δ⁹-Tetrahydrocannabinol-11-oic acid glucuronide 

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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