Abstract: A method for preparing a hop acid mixture having an enantiomeric excess of a (+)-tetrahydro-?-acid is disclosed. In the method, a racemate of a tetrahydro-?-acid is contacted with an amine to form a precipitate having an enantiomeric excess of the (+)-tetrahydro-?-acid. A method for preparing a hop acid is also disclosed. In the method, a racemate of a tetrahydro-?-acid is contacted with an amine to form a precipitate comprising a (+)-tetrahydro-?-acid, and the (+)-tetrahydro-?-acid is isomerized to a hop acid selected from the group consisting of (+)-trans-tetrahydro-iso-?-acids, (?)-cis-tetrahydro-iso-?-acids, and mixtures thereof, and reduced to (+)-trans-hexahydroiso-?-acids and (?)-cis-hexahydroiso-?-acids. An additive for flavoring a malt beverage is also disclosed. The additive includes a bittering agent selected from the group consisting of (+)-trans-tetrahydro-iso-?-acids, (?)-cis-tetrahydro-iso-?-acids, (+)-trans-hexahydroiso-?-acids, (?)-cis-hexahydroiso-?-acids, and mixtures thereof.

Abstract: Tetrahydro iso-?-acids and hexahydro iso-?-acids are prepared from ?-acid resins in the presence of ?-acids derivatives without the use of conventional organic solvents. Specifically, the hydrogenation and hydrogenolyzis step is performed using a liquefied hop resin composed of ?-acids and ?-acid derivatives, hydrogen, and a noble metal hydrogenation catalyst to form desoxytetrahydro ?-acids and hydrogenated iso-?-acid derivatives (e. g., tetrahydroiso- and hexahydro iso-?-acids). The desoxytetrahydro ?-acids are subsequently auto-oxidized and isomerized by the spent noble metal catalyst in an aqueous alkaline solution (without adding peracids, lead, calcium, or magnesium salts) into the desired tetrahydro iso-?-acids and hexahydro iso-?-acids.

Abstract: A method for reducing the amount of beverage soluble metal ions in a diatomaceous earth filter aid is disclosed. The beverage soluble metal ions can be copper and/or iron. In the method, the diatomaceous earth filter aid is contacted with a hop compound selected from iso-alpha-acids, dihydroiso-alpha-acids, tetrahydroiso-alpha-acids, hexahydroiso-alpha-acids, alpha-acids, and beta-acids. The diatomaceous earth filter aid can also be contacted with and an acid other than the hop compound such as phosphoric acid. The iso-alpha-acids, dihydroiso-alpha-acids, tetrahydroiso-alpha-acids, hexahydroiso-alpha-acids, alpha-acids, or beta-acids bind the copper and iron metal ions and/or change the form of copper and iron in diatomaceous earth so the copper and iron are rendered substantially insoluble in a beverage such as beer. A method for filtering a beverage using the treated diatomaceous earth filter aid is also disclosed.

Abstract: A method for preparing a hop acid mixture having an enantiomeric excess of a (+)-tetrahydro-?-acid is disclosed. In the method, a racemate of a tetrahydro-?-acid is contacted with an amine to form a precipitate having an enantiomeric excess of the (+)-tetrahydro-?-acid. A method for preparing a hop acid is also disclosed. In the method, a racemate of a tetrahydro-?-acid is contacted with an amine to form a precipitate comprising a (+)-tetrahydro-?-acid, and the (+)-tetrahydro-?-acid is isomerized to a hop acid selected from the group consisting of (+)-trans-tetrahydro-iso-?-acids, (?)-cis-tetrahydro-iso-?-acids, and mixtures thereof, and reduced to (+)-trans-hexahydroiso-?-acids and (?)-cis-hexahydroiso-?-acids. An additive for flavoring a malt beverage is also disclosed. The additive includes a bittering agent selected from the group consisting of (+)-trans-tetrahydro-iso-?-acids, (?)-cis-tetrahydro-iso-?-acids, (+)-trans-hexahydroiso-?-acids, (?)-cis-hexahydroiso-?-acids, and mixtures thereof.

Abstract: A method for preparing a hop acid mixture having an enantiomeric excess of a (+)-tetrahydro-?-acid is disclosed. In the method, a racemate of a tetrahydro-?-acid is contacted with an amine to form a precipitate having an enantiomeric excess of the (+)-tetrahydro-?-acid. A method for preparing a hop acid is also disclosed. In the method, a racemate of a tetrahydro-?-acid is contacted with an amine to form a precipitate comprising a (+)-tetrahydro-?-acid, and the (+)-tetrahydro-?-acid is isomerized to a hop acid selected from the group consisting of (+)-trans-tetrahydro-iso-?-acids, (?)-cis-tetrahydro-iso-?-acids, and mixtures thereof, and reduced to (+)-trans-hexahydroiso-?-acids and (?)-cis-hexahydroiso-?-acids. An additive for flavoring a malt beverage is also disclosed. The additive includes a bittering agent selected from the group consisting of (+)-trans-tetrahydro-iso-?-acids, (?)-cis-tetrahydro-iso-?-acids, (+)-trans-hexahydroiso-?-acids, (?)-cis-hexahydroiso-?-acids, and mixtures thereof.

Abstract: A method for preparing a hop acid mixture having an enantiomeric excess of a (+)-tetrahydro-?-acid is disclosed. In the method, a racemate of a tetrahydro-?-acid is contacted with an amine to form a precipitate having an enantiomeric excess of the (+)-tetrahydro-?-acid. A method for preparing a hop acid is also disclosed. In the method, a racemate of a tetrahydro-?-acid is contacted with an amine to form a precipitate comprising a (+)-tetrahydro-?-acid, and the (+)-tetrahydro-?-acid is isomerized to a hop acid selected from the group consisting of (+)-trans-tetrahydro-iso-?-acids, (?)-cis-tetrahydro-iso-?-acids, and mixtures thereof, and reduced to (+)-trans-hexahydroiso-?-acids and (?)-cis-hexahydroiso-?-acids. An additive for flavoring a malt beverage is also disclosed. The additive includes a bittering agent selected from the group consisting of (+)-trans-tetrahydro-iso-?-acids, (?)-cis-tetrahydro-iso-?-acids, (+)-trans-hexahydroiso-?-acids, (?)-cis-hexahydroiso-?-acids, and mixtures thereof.

Abstract: A method for reducing the amount of beverage soluble metal ions in a diatomaceous earth filter aid is disclosed. The beverage soluble metal ions can be copper and/or iron. In the method, the diatomaceous earth filter aid is contacted with a hop compound selected from iso-alpha-acids, dihydroiso-alpha-acids, tetrahydroiso-alpha-acids, hexahydroiso-alpha-acids, alpha-acids, and beta-acids. The diatomaceous earth filter aid can also be contacted with and an acid other than the hop compound such as phosphoric acid. The iso-alpha-acids, dihydroiso-alpha-acids, tetrahydroiso-alpha-acids, hexahydroiso-alpha-acids, alpha-acids, or beta-acids bind the copper and iron metal ions and/or change the form of copper and iron in diatomaceous earth so the copper and iron are rendered substantially insoluble in a beverage such as beer. A method for filtering a beverage using the treated diatomaceous earth filter aid is also disclosed.

Abstract: Disclosed are methods for the production of light stable hop products, useful for the brewing of beer or ale to be stored in clear or green glass containers, which beer or ale will not develop objectionable flavor as a result of exposure to light. Light stable hop products are prepared by double extraction of liquid/supercritical CO2 extracted hop solids with ethanol to remove alpha/iso-alpha-acids. Such alpha/iso-alpha-acids may be further removed from the ethanol extraction filtrate obtained in the double extraction process by subjecting such filtrate to an ion exchange medium, or precipitation by a metal ion, heavy metal ion, or alkali metal ion, or hydrogenation to provide an alpha/iso-alpha-acids free filtrate which may be added to the light stable double extracted hop solid residues obtained in the initial double extraction process.

Abstract: Disclosed are methods for the production of light stable hops, useful for the brewing of beer or ale to be stored in clear or green glass containers, which beer or ale will not develop objectionable flavor as a result of exposure to light. Light stable hops are prepared by double extraction of liquid/supercritical CO2 extracted hop solids with ethanol to remove alpha/iso-alpha-acids. Such alpha/iso-alpha-acids may be further removed from the ethanol extraction liquor obtained in the double extraction process by subjecting such liquor to an ion exchange medium, or precipitation by a metal ion, heavy metal ion, or alkali metal ion, to provide an alpha/iso-alpha-acid is free extraction liquor which may be added to the light stable hops residue obtained in the initial double extraction process.

Abstract: A method of making a fully hop flavored beverage employs a hop flavoring agent comprising an extract of hop solids, the hop solids being the residue of a first extraction of hops to remove the alpha acids. Preferably, liquid carbon dioxide is used for the first extraction of the hops and a polar solvent, such as ethanol or water, is used to extract the hop solids. Beverages made by the method and novel compositions for use in the method are also disclosed.

Abstract: Disclosed are methods and compositions for reducing staling that develops during extended storage of fermented malt beverages, beverages, foodstuffs, and cosmetics. In one method, hop solids are extracted with aqueous C1-C6 alcohol to create an extract which is added to wort, the wort is boiled, and thereafter fermented to form a beverage. In another method, hop solids are extracted with aqueous C1-C6 alcohol followed by a mixture of 25% to 75% water and 25% to 75% of C1-C6 alcohol to create an extract, and the extract is added before or after fermentation or directly to a fermented beverage, beverages, foodstuffs, and cosmetics. In another method, hops are extracted with a mixture of 25% to 75% water and 25% to 75% of C1-C6 alcohol to create an extract, and the extract is added in wort, before or after wort boiling, the wort is boiled and thereafter fermented to form a beverage.

Abstract: The isolation and characterization of a group of odorless and non-volatile glycosides from extracted hops (hop solids which have been previously extracted with non-polar solvents) is disclosed. These glycosides are water soluble and consist of a group of aromatic compounds conjugated to mono-, di-, and trisaccharides. These glycosides are responsible for the formation of kettle hop flavor and taste through both chemical and biological transformations. When these glycosides are transformed, they yield an essence and flavorant which imparts a kettle hop flavor and taste when the essence and flavorant is added to an unhopped beer. These kettle hop flavor essences and flavorants provide economy, consistency, flexibility, quality, and convenience to the brewing process because only one unhopped wort is required to brew a stock of unhopped beer. The unhopped beer can then be dosed with the desired amount of kettle hop flavor essence and flavorant.

Abstract: Disclosed are methods for the production of light stable hops, useful for the brewing of beer or ale to be stored in clear or green glass containers, which beer or ale will not develop objectionable flavor as a result of exposure to light. Light stable hops are prepared by double extraction of liquid/supercritical CO2 extracted hop solids with ethanol to remove alpha/iso-alpha-acids. Such alpha/iso-alpha-acids may be further removed from the ethanol extraction liquor obtained in the double extraction process by subjecting such liquor to an ion exchange medium, or precipitation by a metal ion, heavy metal ion, or alkali metal ion, to provide an alpha/iso-alpha-acid is free extraction liquor which may be added to the light stable hops residue obtained in the initial double extraction process.

Abstract: Disclosed are methods for the production of light stable hop products, useful for the brewing of beer or ale to be stored in clear or green glass containers, which beer or ale will not develop objectionable flavor as a result of exposure to light. Light stable hop products are prepared by double extraction of liquid/supercritical CO2 extracted hop solids with ethanol to remove alpha/iso-alpha-acids. Such alpha/iso-alpha-acids may be further removed from the ethanol extraction filtrate obtained in the double extraction process by subjecting such filtrate to an ion exchange medium, or precipitation by a metal ion, heavy metal ion, or alkali metal ion, or hydrogenation to provide an alpha/iso-alpha-acids free filtrate which may be added to the light stable double extracted hop solid residues obtained in the initial double extraction process.

Abstract: The isolation and characterization of a group of odorless and non-volatile glycosides from extracted hops (hop solids which have been previously extracted with non-polar solvents) is disclosed. These glycosides are water soluble and consist of a group of aromatic compounds conjugated to mono-, di-, and trisaccharides. These glycosides are responsible for the formation of kettle hop flavor and taste through both chemical and biological transformations. When these glycosides are transformed, they yield an essence and flavorant which imparts a kettle hop flavor and taste when the essence and flavorant is added to an unhopped beer. These kettle hop flavor essences and flavorants provide economy, consistency, flexibility, quality, and convenience to the brewing process because only one unhopped wort is required to brew a stock of unhopped beer. The unhopped beer can then be dosed with the desired amount of kettle hop flavor essence and flavorant.

Abstract: A method of making a fully hop flavored beverage employs a hop flavoring agent comprising an extract of hop solids, the hop solids being the residue of a first extraction of hops to remove the alpha acids. Preferably, liquid carbon dioxide is used for the first extraction of the hops and a polar solvent, such as ethanol or water, is used to extract the hop solids. Beverages made by the method and novel compositions for use in the method are also disclosed.

Abstract: A method of preparing tetrahydroiso-&agr;-acids from iso-&agr;-acids is disclosed wherein the reaction medium is a buffered, aqueous alcoholic solution. The method can also employ up to 85% w/w spent hydrogenation catalyst. The method advantageously avoids the formation of undesirable side products.

Abstract: Carbon dioxide is used as a reaction solvent in the hydrogenation of organic compounds. The carbon dioxide is preferably a liquid or a supercritical fluid. The hydrogenation method can be used advantageously in methods for making tetrahydroiso-alpha-acids from alpha-acids, iso-alpha-acids, or beta-acids. If beta-acids are used to make tetrahydroiso-alpha-acids, an acidic lower alcohol is preferably added to the carbon dioxide reaction medium to act as a promoter.

Abstract: The isolation and characterization of a group of odorless and non-volatile glycosides from extracted hops (hop solids which have been previously extracted with non-polar solvents) is disclosed. These glycosides are water soluble and consist of a group of aromatic compounds conjugated to mono-, di-, and trisaccharides. These glycosides are responsible for the formation of kettle hop flavor and taste through both chemical and biological transformations. When these glycosides are transformed, they yield an essence and flavorant which imparts a kettle hop flavor and taste when the essence and flavorant is added to an unhopped beer. These kettle hop flavor essences and flavorants provide economy, consistency, flexibility, quality, and convenience to the brewing process because only one unhopped wort is required to brew a stock of unhopped beer. The unhopped beer can then be dosed with the desired amount of kettle hop flavor essence and flavorant.

Abstract: Unsaturated organic compounds, in particular .alpha.-acids and .beta.-acids, are purified prior to hydrogenation by mixing them with an adsorbent capable of adsorbing catalyst poisons, preferably activated carbon, and separating the adsorbent containing the catalyst poisons to recover the thus purified unsaturated organic compounds. A significant reduction in the use of hydrogenation catalyst is realized.