43009-38-7

Basic information

• Product Name: (6aS)-6,6,9-Trimethyl-3-pentyl-6aα,7,8,10aα-tetrahydro-6H-dibenzo[b,d]pyran-1-ol
• Synonyms: (6aS)-6,6,9-Trimethyl-3-pentyl-6aα,7,8,10aα-tetrahydro-6H-dibenzo[b,d]pyran-1-ol
• CAS NO: 43009-38-7
• Molecular Formula: C21H30O2
• Molecular Weight: 314.4617
• Mol File: 43009-38-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (6aS)-6,6,9-Trimethyl-3-pentyl-6aα,7,8,10aα-tetrahydro-6H-dibenzo[b,d]pyran-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (6aS)-6,6,9-Trimethyl-3-pentyl-6aα,7,8,10aα-tetrahydro-6H-dibenzo[b,d]pyran-1-ol(43009-38-7)
• EPA Substance Registry System: (6aS)-6,6,9-Trimethyl-3-pentyl-6aα,7,8,10aα-tetrahydro-6H-dibenzo[b,d]pyran-1-ol(43009-38-7)

Safety Data

• Hazardous Substances Data: 43009-38-7(Hazardous Substances Data)

Upstream product

• 16850-65-0 Methyl tetrahydrocannabinolate 
• 141-27-5 3,7-dimethyl-2,6-octadienal 
• 500-66-3 Olivetol 
• 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 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 16849-50-6 tetrahydrocannabinol 
• 38862-65-6 2,4-dihydroxy-6-n-pentylbenzoic acid ethyl ester 
• 3556-78-3 cannabidiol 
• 945-51-7 1,1'-sulfinylbisbenzene 
• 139-66-2 diphenyl sulfide 
• 22771-44-4 (+)-p-mentha-2,8-dien-1-ol 
• 31684-93-2 (+)-limonene oxide 

Relevant articles and documents

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.

(-)-CIS TETRAHYDROCANNABINOL ((-)-CIS-THC) FOR USE AS A MEDICAMENT

The present invention relates to a tetrahydrocannabinol (THC) type cannabinoid compound for use as a medicament. The THC-type cannabinoid is an enantiomer of the (-)-trans- tetrahydrocannabinol which is a naturally occurring cannabinoid that can be found in cannabis plant strains which have been bred to yield THC as the dominant cannabinoid. The particular enantiomer (-)-cis tetrahydrocannabinol has been found to have properties which are different from the naturally occurring (-)-trans-THC. The cannabinoid (-)-cis-THC has been found to occur in low concentrations in particular cannabis plant strains which have been bred to produce cannabidiol (CBD) as the dominant cannabinoid. Furthermore, the cannabinoid can be produced by synthetic means.

Stereodivergent total synthesis of Δ9-tetrahydrocannabinols

All four stereoisomers of Δ9-tetrahydrocannabinol (Δ9-THC) were synthesized in concise fashion using stereodivergent dual catalysis. Thus, following identical synthetic sequences and applying identical reaction conditions to the same