HUMULONE

Description

Humulone?and its “cousins” adhumulone, cohumulone, prehumulone, and posthumulone are α-acids found in the resin of hops (Humulus lupulus). They are precursors to iso-α-acids, the predominant contributors to bitterness in beer. H. Bungener isolated humulone from commercial hops in 1886, but it wasn’t until 1970 that D. DeKeukeleire and M. Verzele determined its absolute configuration.

The Uses of HUMULONE

(R)-Humulone (CAS# 26471-41-3) can be used as a chemosensory receptor ligand.

Definition

ChEBI: Humulone is an optically active cyclic ketone consisting of 3,5,6-trihydroxycyclohexa-2,4-dien-1-one bearing two 3-methylbut-2-en-1-yl substituents at positions 4 and 6 as well as a 3-methylbutanoyl group at the 2-position. It has a role as an antibacterial drug, an antioxidant, a cyclooxygenase 2 inhibitor and a metabolite. It is a diketone, a triol, a cyclic ketone, an aromatic ketone and a tertiary alpha-hydroxy ketone.

Purification Methods

Crystallise humulon from Et2O. It dissolves slightly in hot H2O but precipitates on cooling. It has max () 237 (13,760) and 282 (8,330) in EtOH. [Wollmer Chem Ber 49 780 1916, Carson J Am Chem Soc 73 4652 1951, Beilstein 8 II 537, 8 III 4034, 8 IV 3410.]