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(12) Patent Application Publication (10) Pub. No.: US 2004/0121040 A1 Forster Et Al US 20040121040A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0121040 A1 Forster et al. (43) Pub. Date: Jun. 24, 2004 (54) METHOD OF PRODUCING A (21) Appl. No.: 10/724,237 XANTHOHUMOL-CONCENTRATED HOP EXTRACTED AND USE THEREOF (22) Filed: Dec. 1, 2003 (75) Inventors: Adrian Forster, Wolnzach (DE); Josef (30) Foreign Application Priority Data Schulmeyr, Wolnzach (DE); Roland Schmidt, Wolnzach (DE); Karin Nov. 30, 2002 (DE)..................................... 102 56 O31.5 Simon, Pfaffenhofen (DE); Martin O O Ketterer, Wolnzach (DE); Birgit Publication Classification Forchhammer, Neustadt (DE); Stefan 7 Geyer, Wolnzach (DE); Manfred s - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - close Gehrig, Woln Zach (DE) ( ) O O - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - f Correspondence Address: (57) ABSTRACT BROWDY AND NEIMARK, P.L.L.C. 624 NINTH STREET, NW SUTE 300 In a method of producing a Xanthohumol-concentrated hop WASHINGTON, DC 20001-5303 (US) extract, the Xanthohumol-containing hop extract is extracted from a Xanthohumol-containing hop raw material by highly (73) Assignee: NATECO2 GMBH & CO. KG, Woln compressed CO as a solvent at pressures above 500 bar and Zach (DE) temperatures above 60° C. US 2004/O121040 A1 Jun. 24, 2004 METHOD OF PRODUCING A the finished beer or other kinds of food or used by itself as XANTHOHUMOL-CONCENTRATED HOP a chemo-preventive preparation. EXTRACTED AND USE THEREOF 0010 Presently, there are two prior art solutions. DE 199 39350 A1 describes a method of producing a xanthohumol BACKGROUND OF THE INVENTION enriched hop extract, with combinations of water and etha nol being used preferably in two steps of extraction. 5 to 15 0001) 1. Field of the Invention percent by weight of Xanthohumol are specified as being 0002 The invention relates to a method of producing a typical. Apart from Xanthohumol, other hop tannins are Xanthohumol-concentrated hop extract as well as the use of extracted as well, having the known clouding tendencies. Such an extract. 0011) Another publication describes how any bitterings 0003 2. Background Art and flavorings that are Soluble with Supercritical CO2 are extracted from a commercial Xanthohumol-containing hop 0004. The background of the invention will be explained extract obtained by the aid of ethanol after the addition of a at the outset by a short explanation of the basic idea of the solid substrate. What is retained after this purification pro invention in terms of dietary physiology. Hop is an indis ceSS is a mix of the Substrate, various resins that are not pensable raw material in beer preparation. It contains three Soluble in CO2 and Xanthohumol of only a weak concentra essential groups of agents in dried form. Hop resins confer tion of 2 percent by weight as against hop. the characteristic bitterness to beer. With its variety of flavor components, hop oil confers a typical flavor to the beer. Hop tannins comprise numerous polyphenols Such as flavanols, SUMMARY OF THE INVENTION proanthocyanides, flavanoids of the kaempherol and quer 0012. It is an object of the invention to specify a method cetin, benzoic acids and cinnamic acid. The evaluation of producing a Xanthohumol-concentrated hop extract, in thereof is not homogeneous as regards beer quality. which to obtain high concentration rates without organic Solvents or multistage extraction processes relating to the 0005 Most hop polyphenols are excellently soluble in Xanthohumol. hot water. They are anti-oxidative and contribute to the taste. However, they tend to forming cloudy protein complexes in 0013 A fundamental solution of this object is specified finished beer during Storage So that the estimation thereof by the invention, according to which the Xanthohumol varies. Lots of breweries deliberately do without the addi containing hop extract is extracted from a Xanthohumol tion of hop polyphenols in order to improve the shelf life of containing hop raw material by highly compressed CO as a their beer and to reduce the Susceptibility thereof to cloud solvent at pressures above 500 bar and temperatures above Ing. 60° C. 0006 Tannin-free hop products are obtained by the 0014 Proceeding from presently available prior art extraction of hop with Solvents. In doing So, fluid and in knowledge, the method according to the invention treads on particular Supercritical CO has proved Successful world a path that deviates entirely from the prior art. In literature, wide; it will dissolve any bittering and flavoring Substances, nonpolar, Supercritical CO has always been described as but no polyphenols. Extracts produced by using ethanol are being totally inept for Xanthohumol eXtraction. All the more of minor importance. Surprisingly, Supercritical CO2, when used in a So far totally unusual combination of pressure and temperature upon 0007 Hop contains a very specific polyphenol, namely extraction, will be able to dissolve Xanthohumol. The result Xanthohuimol, a flavanoid of the chalcone group. Worldwide ing contents of Xanthohumol in the extracts obtained are examinations over the last years have shown that Xantho Stupefyingly high, this also implying a total extract of resin humol possesses highly interesting anti-cancerigenous prop and flavor Substances that are relevant to brewing and erties. Research has meanwhile been extended to live cells. Xanthohumol. There is a hope of using Xanthohumol as a cancer-chemo preventive Substance in the future, which shows there is a 0015 All the patents and literature so far available con demand for concentrating Xanthohumol from hop. sider and describe the extraction properties of Supercritical CO at pressures up to 500 bar. In this context, German 0008 For a polyphenol, the solubility of Xanthohumol is patent 2127618 (production of hop extracts) is cited by way extraordinary. It is So nonpolar that it is hardly Soluble in hot of example. Since no improved extraction properties were water, but excellently soluble in alcohol or alcohol-water found at pressures above 300 to 500 bar, those skilled in the mixes. On the other hand, nonpolar Solvents Such as hexane art assumed that no additional effect could be accomplished are not able to dissolve Xanthohumol. Depending on the by further augmented extraction preSSures. Improved extrac grade, dried hop contains a quantity of 0.2 to 1.0 percent by tion properties of Supercritical CO were assumed to be due weight of Xanthohumol. only to increased temperature, as known from German 0009. During beer preparation, xanthohumol transforms patent 33 46 776. Thus, however, Xanthohumol could not be into isoxanthohumol. Isoxanthohumol possesses clearly leSS dissolved. anti-cancerigenous properties. Moreover, most of the Xan 0016. In the development of the invention it has however thohumol and of the isoxanthohumol is eliminated by yest, been found that using CO at pressures above the 300 to 500 cloud and filtration during beer preparation. Commercial bar so far described will have unexpected results. For beer is not going to be an especially appropriate means of instance, extraction pressures of approximately 600 to 1000 utilizing the cancer-inhibiting potential of Xanthohumol. bar have proved suitable to dissolve Xanthohumol. If for What is absolutely desirable would be a suitable, Xantho example flavoring and bittering Substances are extracted humol-concentrated extract that can be added for example to from the hop at conventional Supercritical conditions of US 2004/O121040 A1 Jun. 24, 2004 approximately 200 to 300 bar and 40 to 60° C., and if the So, bitterings and flavorings that are valuable in brewing are residue is Subjected to another CO extraction at between dissolved. The extraction residue is extracted with CO at 600 to 1000 bar and 70 to 90° C., a hop extract is obtained, 800 bar for three hours on the same or a separate installation. ranging from 10 to 20 percent by weight of Xanthohuimol The extract obtained upon Subsequent extraction is retained contents. By clever Selection of Separating conditions, this in a separator and withdrawn after termination of the extrac extract can be taken in dried form from the Separator. The tion. It contains 5 to 20 percent by weight Xanthohumol, hop extract thus obtained is particularly rich in Xanthohu depending on the raw material. The extract obtained is Solid mol, further containing chlorophyll and moderately bittering and can easily be ground into powder. hop resin components. It is free from undesirable clouding polyphenols Such as flavanols and proanthocyanidines. It Example 2 does not contain any protein, carbon hydrates and in par 0023 10 kg of hop residues, pre-extracted at usual Super ticular any undesired Salts. Such as for instance nitrate. It critical CO conditions, are extracted with CO at 800 bar needs no further processing Such as drying and does not and 80 C. for three hours. The richly green extract gained contain any hop impurities. is collected at 65 bar and 50° C. in a separating vessel. 0017 Pressures higher than 1000 bar might work as well. Xanthohumol contents amount to 5 to 20 percent by weight, They could not be tested for technical reasons. The Xantho depending on the raw material. humol-concentrated hop extract can also be produced with out the utilization of extraction promoters in the CO2. It is Example 3 known from various publications that Supercritical CO2, by 0024. The two steps of extraction can be combined by the addition of entrainers of predominantly more polar having CO2 pass through a bed of hop pellets at 800 bar and character, Such as water or alcohols, changes its extraction 80 C. right from the beginning. By two-stage separation, properties So that more polar Substances can also be dis the Xanthohumol-concentrated extract can be separated at Solved from a Solid. For instance water is used as an 250 bar and 60° C.; the hop extract that is relevant to extraction promoter for eliminating caffeine in coffee or tea brewing is obtained at 65 bar and approximately 50 C.
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