36557-05-8

Basic information

• Product Name: (+/-)-11-HYDROXY-DELTA9-THC
• Synonyms: 11-HYDROXY-DELTA(9)-TETRAHYDROCANNABINOL;(+/-)-11-HYDROXY-DELTA9-THC;RACEMIC DRONABINOL METABOLITE;(6ar-trans)--pentyl;11-hydroxy-delta(sup9)tetrahydrocannabinol;11-hydroxytetrahydrocannabinol;6h-dibenzo(b,d)pyran-9-methanol,6a,7,8,10a-tetrahydro-6,6-dimethyl-1-hydroxy-3;7-hydroxy-delta(sup1)tetrahydrocannabinol
• CAS NO: 36557-05-8
• Molecular Formula: C₂₁H₂₈O₄
• Molecular Weight: 330.46
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Heterocycles
• Mol File: 36557-05-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 136-138°C
• Boiling Point: 437.1 °C at 760 mmHg
• Flash Point: 218.2 °C
• Appearance: /
• Density: 1.071 g/cm³
• Vapor Pressure: 2.06E-08mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: −20°C
• PKA: 9.78±0.60(Predicted)
• CAS DataBase Reference: (+/-)-11-HYDROXY-DELTA9-THC(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-11-HYDROXY-DELTA9-THC(36557-05-8)
• EPA Substance Registry System: (+/-)-11-HYDROXY-DELTA9-THC(36557-05-8)

Safety Data

• Hazard Codes: Xn
• Statements: 22-63
• Safety Statements: 36-45
• RTECS: HP6910000
• Hazardous Substances Data: 36557-05-8(Hazardous Substances Data)

Usage

Description

(+/-)-11-HYDROXY-DELTA9-THC, also known as a metabolite of Delta9-Tetrahydrocannabinol (Delta9-THC), is a phytocannabinoid that has undergone hydroxylation of the methyl group at the C-11 position. It is a major metabolite of Delta9-Tetrahydrocannabinol and is characterized by its off-white to pale yellow solid appearance.

Uses

Used in Pharmaceutical Applications:
(+/-)-11-HYDROXY-DELTA9-THC is used as a pharmaceutical compound for its potential therapeutic effects. As a metabolite of Delta9-THC, it may play a role in the overall pharmacological activity of cannabis, contributing to the various medicinal properties associated with its use.
Used in Research and Development:
(+/-)-11-HYDROXY-DELTA9-THC is used as a research compound for studying the effects of cannabinoids on the human body. Its chemical properties and metabolic relationship with Delta9-THC make it a valuable tool for understanding the mechanisms of action and potential applications of cannabis-based medications.
Used in the Cannabis Industry:
In the cannabis industry, (+/-)-11-HYDROXY-DELTA9-THC is used as a component in the development of new cannabis products, particularly those aimed at providing medicinal benefits. Its presence in cannabis extracts may contribute to the overall efficacy of these products, making it an important factor in product formulation and development.
Used in Analytical Chemistry:
(+/-)-11-HYDROXY-DELTA9-THC is used as a reference compound in analytical chemistry for the identification and quantification of cannabinoids in various samples, such as biological fluids, plant materials, and cannabis products. Its unique chemical properties make it a useful marker for detecting and measuring the presence of other related compounds in these samples.

InChI:InChI=1/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3/t16-,17-/m1/s1

Upstream product

• 500-66-3 Olivetol 
• 936001-98-8 Acetic acid (R)-1-hydroxy-4-isopropenyl-cyclohex-2-enylmethyl ester 
• 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 

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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