16849-50-6

Basic information

• Product Name: 6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol
• Synonyms: 6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol
• CAS NO: 16849-50-6
• Molecular Formula: C₂₁H₃₀O₂
• Molecular Weight: 314.46
• Mol File: 16849-50-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol(16849-50-6)
• EPA Substance Registry System: 6a,7,8,10a-Tetrahydro-6,6,9-trimethyl-3-pentyl-6H-dibenzo[b,d]pyran-1-ol(16849-50-6)

Safety Data

• Hazardous Substances Data: 16849-50-6(Hazardous Substances Data)

Upstream product

• 22771-44-4 (+)-p-mentha-2,8-dien-1-ol 
• 861892-40-2 (4R)-1-methyl-4-(2-(1-propylene))-2-cyclohexene-2-ol 
• 500-66-3 Olivetol 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 16850-65-0 Methyl tetrahydrocannabinolate 
• 3556-78-3 cannabidiol 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 3411-09-4 (E)-4-(2,6-dimethoxy-4-pentylphenyl)but-3-en-2-one 
• 7663-54-9 2',6'-dimethoxy-1'-((E)-3-methylbuta-1,3-dienyl)-4'-pentylbenzene 
• 3410-84-2 2,6-dimethoxy-4-pentylbenzaldehyde 
• 38862-65-6 2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 139-66-2 diphenyl sulfide 

Downstream Products

• 43009-38-7 (6aS,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol 
• 23978-85-0 Δ⁹-tetrahydrocannabinolic acid 
• 7663-51-6 Δ10-THC 
• 521-35-7 cannabinol 
• 7663-50-5 tetrahydrocannabinol 
• 17766-02-8 (+)-(3S,4S)-delta-1-tetrahydrocannabinol 
• 1972-08-3 dronabinol 
• 408337-98-4 (+/-)-Δ9-THC m-nitrobenzenesulfonate 

Relevant articles and documents

A BIOMIMETIC SYNTHESIS OF 1Δ-TETRAHYDROCANNABIOL

Condensation of 1,3-bis(trimethylsiloxy)-1-methoxybutadiene with the acid chloride 12 gave methyl olivetolate (13).Condensation of 13 with (+)-p-mentha-2,8-dien-1-ol gave methyl 1Δ-tetrahydrocannabiolate (14) in 55percent isolated yield.Alkaline hydrolysis of 14 gave 1Δ-tetrahydrocannabinol (1, 1Δ-THC).The synthesis is patterned after the biogenesis of 1.

Δ9-cis-Tetrahydrocannabinol: Natural Occurrence, Chirality, and Pharmacology

Thecis-stereoisomers of Δ9-THC [(?)- 3 and (+)- 3 ] were identified and quantified in a series of low-THC-containing varieties ofCannabis sativaregistered in Europe as fiber hemp and in research accessions of cannabis. While Δ9-cis-THC ( 3 ) occurs in cannabis fiber hemp in the concentration range of (?)-Δ9-trans-THC [(?)- 1 ], it was undetectable in a sample of high-THC-containing medicinal cannabis. Natural Δ9-cis-THC ( 3 ) is scalemic (ca. 80-90% enantiomeric purity), and the absolute configuration of the major enantiomer was established as 6aS,10aR[(?)- 3 ] by chiral chromatographic comparison with a sample available by asymmetric synthesis. The major enantiomer, (?)-Δ9-cis-THC [(?)- 3 ], was characterized as a partial cannabinoid agonist in vitro and elicited a full tetrad response in mice at 50 mg/kg doses. The current legal discrimination between narcotic and non-narcotic cannabis varieties centers on the contents of “Δ9-THC and isomers” and needs therefore revision, or at least a more specific wording, to account for the presence of Δ9-cis-THCs [(+)- 3 and (?)- 3 ] in cannabis fiber hemp varieties.

Process for production of delta-9- tetrahydrocannabinol

The present invention relates to a process for preparation of a delta-9-tetrahydrocannabinol compound or derivative thereof involving treating a first intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the delta-9-tetrahydrocannabinol compound or derivative thereof. Another aspect of the present invention relates to a process for preparation of a cannabidiol or cannabidiolate compound involving reacting a first starting compound with a second starting compound in the presence of a metal triflate catalyst, under conditions effective to form the cannabidiol or cannabidiolate compound. The present invention also relates to a compound of the formula: where R8, R9, and R10 are the same or different and independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or halo, with R1, R2, and R3 defined herein.

METHODS FOR PURIFYING TRANS-(-)-Δ9-TETRAHYDROCANNABINOL AND TRANS-(+)-Δ9-TETRAHYDROCANNABINOL

Methods for making trans-(-)-Δ9-tetrahydrocannabinoI and trans-(+)-Δ9-tetrahydrocannabinol are disclosed herein. In one embodiment, a trans-(-)-Δ9-tetrahydrocannabinoI composition is prepared by allowing a composition comprising (±)-Δ9-tetrahydrocannabinol to separate on a chiral stationary phase to provide a trans-(-)-Δ9-tetrahydrocannabinoI composition comprising at least about 99% by weight of trans-(-)-Δ9-tetrahydrocannabinol based on the total amount of trans-(-)-Δ9-tetrahydrocannabinol and trans-(+)-Δ9-tetrahydrocannabinol. The invention also relates to methods for treating or preventing a condition such as pain comprising administering to a patient in need thereof an effective amount of a trans-(-)-Δ9-tetrahydrocannabinoI having a purity of at least about 98% based on the total weight of cannabinoids.