US 11,505,770 B2Granted

Production of hulupones and hulupones products

AssigneeIfast NV, Innovative Flavor & Aroma Science & Technology

InventorsPascal Mertens, Laurens Claes

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Abstract

The invention relates to a method for the production of hulupones, in particular for the production of hulupones products, suitable for beer bittering, essentially free of compounds, typically formed as side-products during the lupulones oxidation, that can cause negative impact in terms of aroma, taste or haze upon brewing application. The invention also relates to hulupones products, suitable for beer bittering and obtainable by the method of the invention, essentially free of compounds with negative aroma, taste or haze impact upon addition of the hulupones products during the brewing process. The invention also relates to beer bittering with hulupones products, obtainable by the method of the invention, not causing an undesirable or unacceptable aroma, taste or haze impact in the bittered beer.

Claims31

Dependent claims

A method for the production of a hulupones product, comprising the oxidation of one or more lupulones, wherein the hulupones product has a summed mass fraction of 2-methyl-propanoic acid, 3-methyl-butanoic acid, 2-methyl-butanoic acid, lupuloxinic acid, (dehydro)lupulenol, 5-(3-methyl-2-butenyl)-isohumulones, lupulones derivatives with a retained six-membered ring from the original lupulone(s) with a molecular weight higher than the lupulone(s), and bi- and tricyclic lupulones derivatives with a retained six-membered ring from the original lupulone(s) below 20 weight %, relative to the mass of hulupones present,

comprising carrying out the oxidation of one or more lupulones thereby forming one or more hulupones in a solvent medium comprising at least 50 volume % alcohol solvent, in the presence of one or more alkaline earth metal cations, provided as alkaline earth metal complexes or salts,
transforming one or more alkaline earth metal hulupates into one or more hulupones in the free acid form, and
dissolving one or more hulupones, from a precipitated phase comprising hulupones in the free acid form, by selective extraction with an aqueous medium, having a pH in the range of 3-7 whereas one or more lupulones oxidation side-products selected from the group of lupuloxinic acid, (dehydro)lupulenol, 5-(3-methyl-2-butenyl)-isohumulones, lupulones derivatives with a retained six-membered ring from the original lupulones with a molecular weight higher than the lupulones, and bi- and tricyclic lupulones derivatives with a retained six-membered ring from the original lupulones remain precipitated.

A method for the production of a hulupones product, comprising:

the oxidation of one or more lupulones, wherein the hulupones product has a summed mass fraction of 2-methyl-propanoic acid, 3-methyl-butanoic acid, 2-methyl-butanoic acid, lupuloxinic acid, (dehydro)lupulenol, 5-(3-methyl-2-butenyl)-isohumulones, lupulones derivatives with a retained six-membered ring from the original lupulone(s) with a molecular weight higher than the lupulone(s), and bi- and tricyclic lupulones derivatives with a retained six-membered ring from the original lupulone(s), below 20 weight %, relative to the mass of hulupones present,
carrying out the oxidation of one or more lupulones in an aqueous alkaline medium comprising at least 50 volume % water, thereby forming one or more hulupones and one or more lupulones oxidation side-products selected from the group of 2-methyl-propanoic acid, 3-methyl-butanoic acid, 2-methyl-butanoic acid, lupuloxinic acid, (dehydro)lupulenol, 5-(3-methyl-2-butenyl)-isohumulones, lupulones derivatives with a retained six-membered ring from the original lupulone(s) with a molecular weight higher than the lupulone(s), and bi- and tricyclic lupulones derivatives with a retained six-membered ring from the original lupulone(s),
separating one or more hulupones from said lupulones oxidation side-product(s);
precipitating one or more hulupones as one or more alkali metal hulupates from the aqueous medium in which the oxidation of the lupulones is carried out,
separating the precipitated alkali metal hulupates from the aqueous medium,
transforming the alkali metal hulupates into hulupones in the free acid form obtained as a precipitated phase, also comprising lupulones oxidation side-products selected from the group of 2-methyl-propanoic acid, 3-methyl-butanoic acid, 2-methyl-butanoic acid, lupuloxinic acid, (dehydro)lupulenol, 5-(3-methyl-2-butenyl)-isohumulones, lupulones derivatives with a retained six-membered ring from the original lupulones with a molecular weight higher than the lupulones, and bi- and tricyclic lupulones derivatives with a retained six-membered ring from the original lupulones, and
transforming the precipitated alkali metal hulupates into hulupones in the free acid form by subjecting the alkali metal hulupates to an acidification.

4 more elements

Dependencies are inferred from the claim text.