VIEW ARTICLE    DOI: 10.1094/ASBCJ-47-0004

The Structures of Humulene Diepoxides Found in Hops and Beer. Val E. Peacock and Max L. Deinzer, Department of Agricultural Chemistry, Oregon State University, Corvallis, OR97331. J. Am. Soc. Brew. Chem. 47:0004, 1989.

Three isomeric humulene epoxides (I-III) were oxidized with m-chloroperbenzoic acid to their corresponding diepoxides (A-E) to determine the positions of the epoxide rings of the five known diepoxides. Humulene epoxide I gives three diepoxides designated A, B, and C. Epoxide II gives diepoxides A, B, D, and E. Epoxide III gives C, D, and E. Therefore, diepoxides A and B have epoxide rings in the positions of the monoepoxides I and II, diepoxide C in positions I and III, and diepoxides D and E in positions II and III. X-ray analysis of purified humulene diepoxide A showed it to have the epoxide rings trans, therefore the rings of B must be cis.

Keywords: Humulene diepoxide, Humulene epoxide