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+% This file is public domain.
+%
+\input eplain
+
+\headline = {headline\hfil}
+\topinsert
+topinsert
+\endinsert
+
+\parskip = 0pt
+
+\centerline{Xiaogen Yang and Max L. Deinzer}
+\smallskip
+\centerline{Department of Agricultural Chemistry}
+\centerline{Oregon State University, Corvallis, Oregon 97331}
+
+\doublecolumns
+Humulene monoepoxides exist in hop essential oil and were suggested
+as one of the important contributors of hop flavor to fermented
+malt beverages [1-3]. However, it is more possible that the ``noble
+hop'' aroma compounds are produced from certain hop components
+during the brewing process, because the ``noble hop'' aroma is
+distinct from ``dry hop'' aroma. The aging of hops, during which the
+amount of oxidation products of humulene increases [4], is also
+necessary to develop the ``noble hop'' aroma. One approach to find
+out the flavor compounds and their origin is to examine the brewing
+products of the oxygenated sesquiterpenes. The reactions of the
+brewing process can be simplified to hydrolyzation and fermentation
+as the first step. We have been investigated the hydrolysis of
+humulene monoepoxides.
+\singlecolumn
+To simulate the hydrolyzation effect in the ``late hop'' brewing
+process, humulene monoepoxides were boiled in water at
+pH\thinspace 4 for 10 minutes. After boiling, a large amount of
+the epoxides remain unreacted. When the solution was kept at
+ambient temperature for several weeks, humulene epoxides were
+then almost completely hydrolyzed. To accelerate the hydrolysis
+process, humulene epoxides were suspended in a aqueous solution
+buffered at pH\thinspace 4 and boiled for three hours under
+reflux. All three humulene monoepoxides produced a complex
+mixture after the reaction (Figure 1). The hydrolysis products
+can be easily separated into two groups by extraction with
+pentane and dichloro\-me\-thane subsequently. The pentane
+extracts are less polar, more volatile and smell stron\-ger than
+the dichloro\-methane extracts. Sensory evaluation of the
+hydrolysis products of humulene epoxide II and III by sniffing
+gas chromatography effluent indicates that some of the compounds
+have the flavor notes which are close to the ``noble hop'' aroma
+character described as ``spicy, citrus, floral'' (Table 1).
+
+\bye