80797-01-9

Upstream product

• 6753-98-6 α-caryophyllene 
• 531492-87-2 (9E)-humulene-2,3;6,7-diepoxide 

Relevant academic research and scientific papers

Rearrangement of humulene-8,9-epoxide

Rearrangement of humulene-8,9-epoxide with tin(IV) chloride leads to the formation of a bicyclic alcohol, the structure of which is related to a rearrangement product of humulene itself.

Where is the Oxygen? Structural Analysis of α-Humulene Oxidation Products by the Crystalline Sponge Method

Crystal structures of α-humulene, a cyclic sesquiterpene, and its oxidized subproducts, were analyzed by the crystalline sponge method. Regio- and stereochemistry, including absolute configuration when a chiral oxidant was applied, and the stable conformations of all the scaffold-related compounds were successfully determined for samples on a 5-50 μg scale.

Monoepoxidation of humulene 2,3-epoxide to humulene 2,3;6,7-diepoxides. Observation of the rotation of the double bond plane by 1H NMR spectral analysis and conformation

The reaction of (6E,9E)-humulene 2,3-epoxide (7) with m-CPBA produced two known humulene 2,3;6,7-diepoxides (8 and 9), and careful analysis of the 1H NMR of 7 at various temperatures suggested an equilibrium of four possible conformations, CT,

Transformations of α-Humulene and Some Its Monoepoxy Derivatives over Solid Acid Catalysts. Epoxidation of α-Humulene

2,3- and 6,7-Epoxy derivatives of α-humulene in liquid superacids at low temperatures and over solid catalysts at room temperature undergo isomerizations whose direction is determined by conformational factors.

Diethyl ether-boron trifluoride (1/1) induced transannular cyclization reaction of humulene 2,3-epoxide

The treatment of (6E, 9E)-2,3-epoxy-3,7,11,11-tetramethylcycloundeca-6,9-diene with Et2O·BF3 produced four novel transannular cyclized compounds of (4E)-(1S*, 8S*, 9S*)-8-acetoxy-6,6,9-trimethyl-2-methylenebicyclo[7.2.0]undec-4-ene (13), (2Z, 4E)-(1S*, 8S*, 9S*)-8-acetoxy-2,6,6,9-tetramethylbicyclo[7.2.0]undeca-2,4-diene (14), (6E)-(1R*, 2R*, 3S*, 10R*)-3-acetoxy-2,5,5-trimethyl-9-methylenebicyclo[8.1.0]undec-6-ene (15), and (4E)-(1S*, 2S*, 8S*, 9S*)-2,8-diacetoxy-2,6,6,9-tetramethylbicyclo[7.2.0]undec-4-ene (16) together with three new acetates: (2E, 5E, 8E)-1-acetoxy-2, 6,10,10-tetramethylcycloundeca-2,5,8-triene, (1E, 6E)-3,9-diacetoxy-2,5,5,9-tetramethylcycloundeca-1,6-diene, and (4E, 7E)-1-acetoxy-3,3,7-trimethyl-11-methylenecycloundeca-4,7-diene. The configurations of the bicyclo[7.2.0]undecane skeletons (13, 14, and 16) and 15 maintained the shape of TC and CT conformers of the original epoxide, respectively.