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

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

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

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

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.

TETRAHYDROCANNABINOID ANTIGENS AND METHOD OF USE

The present invention is directed to Δ8-THC and Δ9-THC compounds useful for the covalent attachment to immunogenic molecules to form antigens for the preparation of specific binding molecules to Δ9-Tetrahydrocannabinol, Δ9-Tetrahydrocannabinoids, Δ8-Tetrahydrocannabinol, and Δ8-Tetrahydrocannabinoids, and their derivatives and metabolites. The present invention is directed to the compounds, their method of preparation, cell lines producing the specific binding molecules, methods of using the antigens to produce the specific binding molecules, and test devices containing the antigens, haptens, or specific binding molecules of the invention.

Studies on the synthesis of (-)-11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THC) and related compounds: An improved oxidative procedure

A facile procedure is described whereby Δ9-THC aldehydes 4, as their tert-butyldimethylsilyl derivatives, are conveniently oxidized to the corresponding acids with sodium chlorite in the presence of a large excess of 2-methyl-2-butene without isomerization of the Δ9-double bond. Deprotection of the O-protecting group with tetrabutylammonium fluoride in tetrahydrofuran gave the acids 2 in an overall yield of ≥80%. A study of other oxidizing agents and protecting groups demonstrated that this is the procedure of choice for the preparation of 9-carboxy-Δ9-tetrahydrocannabinols.

Glucuronic acid conjugate of Δ1-tetrahydrocannabinol identified in the urine of man

A Δ1-tetrahydrocannabinol (Δ1-THC) metabolite has been identified as an O-glucuronide of Δ1-THC in the human urine after oral administration of Δ1-THC. The metabolite was present in small amounts and its identify was confirmed by comparison of its mass spectrum to that of a reference compound.