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    • 专利摘要:
    The present invention discloses a method of preparing beer with an ethanol content of 0 - 1.0 vol.%, Comprising providing a medium with an ethanol content of 0 - 20 vol.%, Which medium comprises beer with limited fermentation; subjecting said medium to a distillation step, whereby the amount of one or more aldehydes selected from the group consisting of 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, 3-methylthiopropionaldehyde, phenylacetaldehyde, hexanal, trans-2-nonenal, benzaldehyde and furfural in the medium is reduced, and also, where present, the ethanol content is reduced to a content in the range of 0-1.0% by volume. The invention also discloses beer obtained by said method.
    公开号:BE1026599B1
    申请号:E20195602
    申请日:2019-09-10
    公开日:2020-04-09
    发明作者:Hilda Els Smit；Eric Richard Brouwer；Augustinus Cornelius Aldegonde Petrus Albert Bekkers；Albert Doderer
    申请人:Heineken Supply Chain Bv；
    IPC主号:
    专利说明:

    (30) Priority data:
    10/09/2018 NL PCT / NL2018 / 050589 (73) Holder (s):
    HEINEKEN SUPPLY CHAIN private company1017 ZD, AMSTERDAMThe Netherlands (72) Inventor (s): SMIT Hilda Els1017 ZD AMSTERDAMThe NetherlandsBREWER Eric Richard1017 ZD AMSTERDAMThe NetherlandsBEAKERS Augustinus Cornelius Aldegonde Petrus Albert1017 ZD AMSTERDAMThe NetherlandsKILLER Albert1017 ZD AMSTERDAMThe Netherlands
    (54) Low alcohol beer (57) The present invention discloses a method of preparing beer with an ethanol content of 0 - 1.0 vol.%, Comprising providing a medium with an ethanol content of 0 - 20 vol.%, Which medium beer with limited fermentation; subjecting said medium to a distillation step, whereby the amount of one or more aldehydes selected from the group consisting of 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, 3-methylthiopropionaldehyde, phenylacetaldehyde, hexanal, trans-2-nonenal, benzaldehyde and furfural in the medium is reduced, and also, if present, the ethanol content is reduced to a content in the range 0-1.0% by volume. The invention also discloses beer obtained by said method.
    BE2019 / 5602
    Low alcohol beer
    The present invention relates to the production of alcohol-free or low-alcohol beer with improved taste. More specifically, the present invention provides a method of producing an alcohol-free fermented beer in which so-called "wort-like" taste notes are reduced. The invention also relates to a fermented alcohol-free beer with a unique pleasant taste profile with reduced unwanted wort-like taste notes, which makes the beer more drinkable.
    Background
    Beer is one of the most popular alcoholic drinks worldwide. It is prepared by fermentation of a sugary aqueous matrix derived from grains, using yeast that converts the sugars into ethanol ("alcohol"). The beer production process is well known, and those skilled in the art are able to obtain beer on the basis of conventional general knowledge and the information disclosed herein.
    Beer is usually made from grain such as barley, although other grain types including but not limited to wheat or sorghum can also be used. Beer is usually produced by a process that includes the following basic steps: mashing a mixture of grain and water to obtain a mash; separating the mash into wort and brewing; cooking the wort to obtain a boiled wort; fermenting the cooked wort with live yeast (such as Saccharomyces pastorianus or Saccharomyces cerevisiae) to produce a fermented wort; subjecting the fermented wort to one or more further process steps (e.g. maturation and filtration) to produce beer; and packaging the beer in a sealed container, e.g. a bottle, can or barrel.
    In an exemplary process of producing a barley malt beer, the barley is malted, meaning it is left
    BE2019 / 5602 germinate and it is then dried ('eesten') to produce malt. This process is important for the formation of flavor and color compounds, and the formation of enzymes that are important for further flavor development and starch breakdown. The malt is then ground and suspended in water ('mashing'). The maize is heated to facilitate starch breakdown. Subsequent filtration results in wort, which is a more or less clarified aqueous solution of fermentable sugars, which also contains various flavors and aromas and many other compounds. Both desirable and undesirable flavor and aroma compounds are present in wort. An exaggerated “wort-like” taste, which comes from excessive presence of aldehyde, is generally considered undesirable.
    The wort is boiled to sterilize it, to precipitate proteins and to concentrate it. Hops are optionally added to add bitterness and flavor. After removal of the precipitant, this mixture is subjected to fermentation. Fermentation results in the conversion of fermentable sugars into ethanol and carbon dioxide, and also results in the formation of various new flavor compounds, including esters. At the same time, fermentation of beer reduces the amount of aldehydes, thereby preventing an exaggerated wort-like taste from the resulting beer. After fermentation, the beer can be filtered and / or stored to optimize appearance and taste.
    Health concerns and increased road safety awareness associated with the alcohol content of beer have heightened interest in low-alcohol or even non-alcoholic beer. Currently, there are two main techniques for the production of low-alcohol or non-alcoholic beer: the de-alcoholization of regular (alcoholic) beer, and the preparation of beer by a method that limits the formation of alcohol by means of an adapted fermentation (“limited alcohol fermentation ”).
    BE2019 / 5602
    De-alcoholization of beer is carried out on regular brewed beer, and is intended to remove ethanol, but as few other flavor components as possible. De-alcoholization can be achieved by, for example, rectification, reverse osmosis or dialysis of regular beer (for general methodology see Mangindaan et al., Trends in Food Science and Technology 71 (2018), 36-45; or Branyik et al., J. Food Eng. 108 (2012), 493506). However, it is a challenge to prevent loss of flavor in the de-alcoholization of beer. A disadvantage of de-alcoholized beer is therefore a bland taste, which can be corrected by adding flavors (taste and smell) in order to obtain an acceptable beer. However, because flavor is complex due to the wide variety of compounds that are responsible for imparting flavor together, de-alcoholized and subsequently flavored beer is generally considered to be less pleasant in taste than regular beer flavor.
    Low-alcohol and non-alcoholic beer can also be prepared by limited alcohol fermentation (see Branyik et al., Cited above). Limited alcohol fermentation is a process in which wort is fermented under conditions where there is little or no ethanol formation (or at least, where the entire fermentation process results in little or no net alcohol formation).
    An important method is cold-contact fermentation. When wort is fermented at a low temperature, yeast hardly produces alcohol, although it does produce a number of flavor components such as esters, although amounts per ester may differ from the amounts obtained from regular fermentation. At a low temperature, the ability of yeast to reduce the aldehyde level responsible for the wort-like taste is reduced. Therefore, low-alcohol or non-alcoholic beer produced using a cold-contact process (or other limited fermentation process) has the disadvantage of a
    BE2019 / 5602 relatively high amount of aldehyde, which imparts the wort-like taste to low-alcohol or non-alcoholic beer. In addition, such beers are generally relatively sweet due to the presence of residual fermentable sugars. Among the various types of limited fermentation beer, cold-contact fermented beer is particularly known to include high amounts of aldehydes.
    In general, the taste of beer is the result of a delicate balance between, among other things, the amount and kind of different sugars, the amount and kind of different flavor compounds such as esters, and the amount and kind of different wort-like (aldehyde) flavors, as well as the amount of alcohol. The presence of alcohol suppresses some of the taste properties, and enhances others. For example, the presence of alcohol suppresses the wort taste. Therefore, the taste of regular (alcoholic) beer cannot simply be imitated by introducing all the compounds responsible for taste in identical quantities, in an alcohol-free beer (see Brânyik et al., Cited above). However, a small base level of aldehydes does add to the flavor of the beer, as described in, for example, US 2012/0207909. In addition, the amount and type of salts, organic acids and amino compounds, such as small peptides and amino acids, affect the taste of the final beer.
    Existing low-alcohol or non-alcoholic beers generally suffer from a lack of drinkability. Most people get satiated by the taste after just one or two glasses, as opposed to drinking regular alcoholic beer. The taste saturation is generally caused by a predominant taste caused by overly intense wort-like flavors due to high aldehyde levels in combination with low alcohol content and / or too high sweetness. In addition, existing low-alcohol or non-alcoholic beers are often unbalanced. The
    BE2019 / 5602 present invention provides a method of overcoming these drawbacks.
    Summary of the invention
    The present invention discloses a method for preparing beer with an ethanol content of 0 - 1.0% by volume, comprising providing a medium with an ethanol content of 0 - 20% by volume, which medium contains beer with limited fermentation, the subjecting the medium to a distillation step, thereby decreasing the amount of one or more aldehydes selected from the group consisting of 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, 3methylthiopropionaldehyde ("methional"), phenylacetaldehyde, hexanal, trans-2- nonenal, benzaldehyde and furfural, and thereby also decreasing the ethanol content, if any, to a content in the range of 0-1.0% by volume.
    The present invention discloses a method in which aldehydes are lowered by distillation of a medium comprising beer obtained from limited fermentation. This has the advantage of removing aldehydes, resulting in favorably low aldehyde amounts, and a favorable aldehyde to sugar ratio. In preferred embodiments, distillation of beer with limited fermentation is performed in the presence of alcohol (ethanol), which confers an even more favorable aldehyde to sugar ratio, and an improved flavor profile. If the distillation is carried out on a mixture of regular beer and beer with limited fermentation, the balance between all flavor compounds can be optimized to obtain an alcohol-free or low-alcohol beer with an improved flavor profile, which is more drinkable than existing commercially available low-alcohol or non-alcoholic beers . The present process allows for the removal of aldehydes which cause so-called "wort-like" unpleasant flavors, while simultaneously lowering the ethanol content to
    BE2019 / 5602 available alcohol-free or low-alcohol beer. In addition, the method allows to reduce the sweet taste of alcohol-free or low-alcohol beer, thereby reducing or eliminating the predominant taste. This leads to a more drinkable beer.
    The present invention further discloses a beer having an ethanol content of 0-1.0 vol%, with a total sugar content, defined as the total of glucose, fructose, sucrose, maltose, and maltotriose, of at least 0.2 g / 100 ml; and a total content of Strecker aldehydes, defined as the total of 2-methylpropanal, 2-methylbutanal, 3methylbutanal, 3-methylthiopropionaldehyde, and phenylacetaldehyde, less than 50 pg / l; and / or with less than 18 pg / l, preferably less than 10 pg / l 2-methylpropanal, preferably 2 - 10 pg / l, less than 3.8 pg / l 2methylbutanal, preferably 0.2 - 2, 5 pg / l, less than 14 pg / l 3methylbutanal, preferably 1 - 10 pg / l, less than 10 pg / l 3methylthiopropionaldehyde, preferably 2 - 8 pg / l, less than 20 pg / l phenylacetaldehyde, preferably 1 8 pg / l, wherein the weight ratio of the total weight of 2-methylpropanal, 2-methylbutanal, 3methylbutanal, 3-methylthiopropionaldehyde, and phenylacetaldehyde, relative to maltose, is less than 15 pg / g maltose.
    It has been found that a beer as defined herein has a less predominant taste, a less sweet taste and a lower wort-like taste, and is therefore more drinkable than existing non-alcoholic beer. Detailed description
    The invention discloses a method for preparing beer with an ethanol content of 0 - 1.0% by volume, comprising • providing a medium with an ethanol content of 0 - 20% by volume, comprising medium beer with limited fermentation;
    Subjecting said medium to a distillation step, thereby reducing the ethanol content, if any, and causing the amount of one or more aldehydes selected from the
    BE2019 / 5602 group consisting of 2-methylpropanal, 2-methylbutanal, 3-methylbutanal,
    3-methylthiopropionaldehyde, phenylacetaldehyde, hexanal, trans-2nonenal, benzaldehyde and furfural is reduced.
    In the present context, beer is to be understood in a broad sense, that is, beer can refer to any type of beer, including but not limited to ale, porter, stout, lager and bock beer. Beer is preferably a malt-based beer, that is, a beer prepared from the fermentation of wort prepared from (inter alia) malt. Preferably, beer is lager, which is a beer obtained by fermentation at 7-15 ° C using a bottom yeast, and subsequent storage at low temperature. Lager, for example, includes pilsner. Most preferably, a beer as described herein is a pilsner. A pilsner is a light lager. It is an object of the invention to provide an alcohol-free beer with the taste and drinkability of a regular beer.
    In the present text, "non-alcoholic or low-alcohol beer" is a beer with an ethanol content of 1.0% by volume ("ABV") or less, preferably 0.5% by volume or less, more preferably 0.2% by volume. % or less. Such beers are called non-alcoholic (NA) beers. NA beer is thus a beer with an ethanol content of 0 - 1.0% by volume, such as preferably 0 - 0.5% by volume.
    In the present context, "aldehydes" or "total aldehydes" refers to the aldehydes 2-methylpropanal, 2-methylbutanal, 3methylbutanal, 3-methylthiopropionaldehyde, phenylacetaldehyde, hexanal, trans-2-nonenal, benzaldehyde and furfural. Among the aldehydes are "Strecker aldehydes", which are the aldehydes 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, 3-methylthiopropionaldehyde, and phenylacetaldehyde.
    The invention discloses a method for the distillation of a medium comprising beer with limited fermentation, which method reduces the amount of aldehydes, including Strecker aldehydes.
    A limited fermentation beer is defined as a fermented beer obtained by limited ethanol fermentation
    BE2019 / 5602 wort. Limited ethanol fermentation of wort is fermentation that does not result in significant net ethanol formation. That is, limited fermentation as defined herein results in 1 vol% or less, preferably 0.5 vol% or less ethanol. Thus, a beer with limited fermentation has an ethanol content of 1.0% by volume or less, preferably 0.5% by volume or less. The person skilled in the art is aware of various techniques of limited fermentation that do not result in significant net ethanol formation. Examples are limited ethanol fermentation of wort characterized by a temperature below 7 ° C, preferably -1 - 4 ° C, such as -0.5 - 2.5 ° C, preferably for a period of 8 - 72 hours, more preferably 12 - 48 hours (“cold-contact fermented beer”); and / or a short (e.g., less than 2 hours) fermentation time, which fermentation quickly stopped by temperature inactivation, such as by rapid cooling to -0.5 - 1 ° C, optionally followed by subsequent pasteurization ("stopped fermentation beer"); and / or fermentation by a yeast strain producing relatively low amounts of ethanol under the fermentation conditions employed, such as, for example, a yeast strain producing less than 0.2 g of ethanol per gram of fermentable sugar in the wort, preferably less than 0.1 g of ethanol per gram fermentable sugar. Suitable strains (e.g. Crabtrenegative strains) are known in the art and the amount of ethanol produced under varying fermentation conditions can be determined by routine experiments ("yeast-limited beer"); and / or fermentation using a first ethanol-producing yeast strain, in the presence of a sufficient amount of a second yeast strain that consumes ethanol, such as Saccharomyces rouxii, to consume substantially all ethanol produced by the first yeast strain; and / or wort with a content of fermentable sugars such that a maximum of 1.0% by volume of alcohol is produced upon completion of the
    BE2019 / 5602 fermentation thereof. In this case, the wort usually has a fermentable sugar content of less than 17.5 g / l, preferably less than 12 g / l, more preferably less than 8 g / l ("low sugar worthier").
    A beer with limited fermentation is a beer that is obtained through limited ethanol fermentation of wort. Limited fermentation is a process in which the product obtained from the fermentation has an ethanol content of 1.0% by volume or less, preferably 0.5% by volume or less. Such beers can be obtained by well known methods such as, for example, described in Brânyik et al., J. Food Eng. 108 (2012), 493-506. Typically, the total amount of Strecker aldehydes in limited fermentation beer is at least 60 pg / l, and the total aldehyde amount is at least 600 pg / l.
    Limited fermentation beer has not been subjected to a deal alcoholization step to achieve said ethanol content of 1.0% by volume or less, preferably 0.5% by volume or less. Those skilled in the art know several suitable techniques for the de-alcoholization of a fermented beer, and none of these techniques has been used to achieve said ethanol content of 1.0% by volume or less, preferably 0.5% by volume or less. A beer with limited fermentation, in the present context, can optionally be subjected to a deal alcoholization step to reduce the ethanol content of 1.0% by volume or less, preferably 0.5% by volume or less, obtained from the fermentation to lower ethanol content. Preferably, however, a limited fermentation beer as defined herein is not subjected to a deal alcoholization step at all.
    A de-alcoholization step as used for de-alcoholization of beer is well known in the art, and may refer to, for example, a rectification step, a reverse osmosis step, a dialysis step or a freeze concentration step to remove ethanol from the fermented beer. Such techniques are described, for example, in Mangindaan et al., Cited above.
    BE2019 / 5602
    The limited fermentation beer is preferably a sugar-depleted worthier, a yeast-limited beer, a stopped fermentation beer, or a cold-contact fermented beer. In one embodiment, the limited fermentation beer is a low-sugar worthier. In a further embodiment, the limited fermentation beer is a yeast-limited beer. In yet a further embodiment, the limited fermentation beer is a stopped fermentation beer. In yet a further embodiment, the limited fermentation beer is a cold-contact fermented beer. In preferred embodiments, the limited fermentation beer is a cold-contact fermented beer.
    Cold contact fermentation is well known in the art, and those skilled in the art can obtain a cold contact fermented beer by any means known in the art or disclosed herein. An exemplary method of obtaining a cold-contact fermented beer is described, for example, in Brânyik et al., Cited above. Alternatively, cold-contact fermented beer can be obtained commercially.
    The distillation of a medium comprising limited fermentation beer results in the removal (of the medium) of one or more aldehydes selected from the group consisting of 2-methylpropanal, 2methylbutanal, 3-methylbutanal, 3-methylthiopropionaldehyde, and phenylacetaldehyde. These aldehydes will collectively be called “Strecker Aldehydes”. The distillation also accomplishes removal of one or more aldehydes selected from the group consisting of 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, 3methylthiopropionaldehyde, phenylacetaldehyde, hexanal, trans-2-nonenal, benzaldehyde, and furfural. These aldehydes will collectively be called "total aldehydes".
    Distillation is a well-known process, and those skilled in the art can determine suitable distillation conditions based on current general knowledge
    BE2019 / 5602 and the information disclosed herein. In preferred embodiments, the distillation is carried out at a temperature of 10 - 100 ° C, more preferably 20 - 65 ° C, more preferably 30 - 50 ° C, even more preferably 40 - 46 ° C. The distillation is further preferably carried out at reduced pressure, such as at a pressure of 0.01 - 500 mbar, preferably 1 - 200 mbar, more preferably 50 - 150 mbar, and even more preferably 80 - 110 mbar.
    Preferably, the distillation is a vacuum distillation, at a temperature and pressure as described. A vacuum distillation process in accordance with the present invention may comprise one or more of the steps of • preheating the medium, for example, in a heat exchanger • optionally, degassing the medium, for example, in a vacuum degasser • separation of the medium from aldehydes and ethanol, if present, in one or more vacuum columns, for example a packed bed column • cooling and optionally carbonation of the resulting alcohol-free or low-alcohol beer.
    The skilled person can select a suitable device for carrying out the distillation. For example, the distillation can be carried out in a commercially available rectification column. those skilled in the art may select a suitable institution based on common knowledge of the general art, as described in "Chemical Engineering Design", by R. K. Sinnott (part 6, fourth edition, 2005).
    As the skilled person will understand, the distillation can be adjusted to obtain a desired ethanol content. In preferred embodiments, the ethanol content of the beer obtained after distillation is 1% by volume or less, preferably 0.5% by volume or less, even more
    BE2019 / 5602 preferably 0.2 vol.% Or less, even more preferably 0.1 vol.% Or less. A beer with 1 full. % or less ethanol can also be called alcohol-free or low-alcohol beer or NA beer.
    The medium to be distilled is a medium comprising beer with limited fermentation. In one embodiment, the medium comprises only limited fermentation beer, in which embodiment the invention discloses a method for the distillation of beer with limited fermentation, which method accomplishes the removal of aldehydes (and ethanol, if any) from the beer with limited fermentation. Preferred types of beer with limited fermentation are defined above.
    In another embodiment, the medium to be distilled is a medium comprising beer with limited fermentation and an additional amount of ethanol. In this embodiment, the medium preferably comprises beer with limited fermentation and has a total ethanol content of 1 - 15% by volume, preferably 2 - 10% by volume, more preferably 2.5 - 7.5% by volume. In this embodiment, the medium is obtained by a step of adding ethanol to the beer with limited fermentation. In this embodiment, the distillation step further effects the removal of ethanol from the medium.
    Ethanol can be combined with the limited fermentation beer as pure (such as, for example, more than 95%, preferably more than 98%) ethanol, or as an aqueous medium comprising ethanol, such as an aqueous medium comprising at least 2% by volume, at preferably at least 4% by volume ethanol. In highly preferred embodiments, the aqueous medium comprises 2-15 vol.% Ethanol, preferably 4-10 vol.% Ethanol.
    It is an additional advantage of this embodiment that removal of aldehyde in the presence of alcohol becomes less efficient. This is beneficial because a certain base level of aldehydes is preferred to impart full beer flavor, as is, for example
    BE2019 / 5602 described in US 2012/0207909. The basic level of aldehydes, in combination with suitable flavor compounds, results in a beer with low sweetness and low wort-like taste, which is correctly balanced. It has been found to be advantageous with low-alcohol or non-alcoholic beer as defined herein when Strecker aldehydes are present in an amount of at least 10 µg / l; total aldehydes are preferably present in an amount of at least 25 µg / l. By performing the distillation step in the presence of alcohol as disclosed above, the aldehyde to sugar ratio can be optimized, thereby resulting in an alcohol-free or low-alcohol beer with improved taste.
    In highly preferred embodiments, the watering medium comprising ethanol is a regular beer. In this embodiment, the medium comprises a mixture of limited fermentation beer and regular beer. Preferably, the medium is a mixture of limited fermentation beer and regular beer.
    "Regular beer", in this context, is regular brewed beer, obtained using a fermentation process that results in more than 1% by volume of ethanol. Thus, regular beer, as defined herein, has an ethanol content of greater than 1% by volume, and preferably less than 15% by volume. The ethanol content of regular beer is preferably 2.15% by volume, more preferably 2.5-12% by volume, more preferably 3.5-9% by volume. The regular beer is preferably a lager, as described above, most preferably a pilsner. Those skilled in the art are able to obtain regular beer, including regular lager and pilsner, for example, by the methods described in The Brewer's Handbook (second edition) by Ted Goldammer (2008, Apex Publishers). Alternatively, regular beer can be obtained commercially. Regular beer generally includes a total amount of Strecker aldehydes of 50 pg / l or less, and a total amount of aldehydes of 400 pg / l or less.
    BE2019 / 5602
    Embodiments in which the medium comprises regular beer and beer with limited fermentation are highly preferred, because these embodiments have further advantages.
    First of all, creating a mixture of beer with limited fermentation and regular beer means that the beer with limited fermentation is diluted. This, in turn, means that the aldehyde amount to be removed from the medium by distillation is reduced by dilution, because aldehydes are present in higher amounts in beer with limited fermentation than in regular beer. This reduces processing time and energy. However, the dilution step alone does not reduce the aldehydes to the required amounts, so the distillation step is still required to effect sufficient aldehyde removal.
    Second, regular beer includes higher amounts of flavor compounds such as esters than beer with limited fermentation. Mixing beer with limited fermentation and regular beer increases the amount and type of flavor compounds in the medium, resulting in increased amounts and types of flavors in the final beer after distillation.
    In particular, a regular preferred beer used in a method of the invention includes ethyl 2-methylpentanoate, which is important to mask wort (aldehyde) taste, to impart a refreshing taste, and to make the beer more drinkable. (See also pending patent application entitled "Low-alcohol beer with reduced wort flavor" (PCT / NL2018 / 050587) filed the same day).
    In addition, regular beer includes free amino nitrogen, including amino acids, which also contribute to the flavor of the final beer. By mixing beer with limited fermentation and regular beer, the medium is enriched with, among other things, free amino nitrogen. It of distillation
    BE2019 / 5602 beer thus preferably comprises 20 - 250 mg / l of free amino nitrogen (FAN), more preferably 50 - 200 mg / l, more preferably 75 - 150 mg / l.
    In addition, regular beer includes ethyl 2-methylpentanoate, which in turn becomes part of the final beer. Thus, the final beer usually comprises at least 0.001 µg / l ethyl 2-methylpentanoate, which imparts a refreshing taste, and has been found to be particularly effective in masking aldehyde flavor. Preferably, the amount of ethyl 2-methylpentanoate is in the range of 0.001-1000 pg / L.
    Third, regular beer includes foam-negative factors. An important foam-negative factor is AcHFA. The effects of AcHFA as a foam negative factor are described in also pending patent application entitled "foam stability" (PCT / NL2018 / 050588), filed the same day.
    AcHFA ("acetylated hydroxy fatty acid" [acetylated hydroxy fatty acid]) is a C12-C22 fatty acid, comprising a carboxylic acid group and a C11-C21 linear alkyl group, which alkyl group may be partially unsaturated and which alkyl group is substituted with at least one hydroxyl group and at least one acetate group. An acetate group (HsCCO2 ~) is abbreviated (as is common in the art) as ~ OAc.
    AcHFA can be defined as structure 1
    where n = an integer in the range of 4-9, and where each
    A, B, C and / or D can be the same or different, with either
    a) is a single bond, in which case:
    one of A and B is H, OH or OAc and the other of A and B is H;
    BE2019 / 5602 is one of C and D H, OH or OAc and the other of C and D is H; or
    b) is a double bond, in which case:
    one of A and BH is, while the other of A and B is not present (meaning that the other of A and B is nothing), and one is of C and DH, while the other of C and D is not present ( meaning that the other of A and B is nothing);
    provided that in structure 1 at least one of all A, B, C, D is OH and at least one of all A, B, C, D is OAc.
    As is well known, the double bond can have a cis or trans configuration, but the configuration is preferably cis. Furthermore, as is usual for organic acids, the acid group can be in neutral form (as shown; -CO2H), but can also be in ionic form (~ CO2 ')> or in salt form ((~ CO2) X M, where M any metal ion can be, and preferably a metal ion available in beer, such as, for example, an ion of Na, K, Ca, Mg, Fe, Cu, Zn or Mn, and where x = 1 if M is monovalent (Na or K), and wherein x may be 1, 2 or 3 for higher valency ions Carbon atoms bearing OH or OAc may independently have an R or S configuration, but adjacent carbon atoms bearing an OH and an OAc group have both preferably have a // configuration, or both have an S configuration (RR and SS) Alternatively, one carbon atom of adjacent carbon atoms carrying an OH and an OAc group has an S configuration, and the other carbon of the two adjacent carbon atoms a // configuration (RS or SR).
    Preferably, AcHFA includes one hydroxyl group and one acetate group located on adjacent carbon atoms, among the optional multiple hydroxyl and / or acetate groups. Furthermore, AcHFA is preferably a C16-C20 fatty acid (n = 6-8 in structure 1), most preferably a Cl8 fatty acid (n = 7 in structure 1). It is very preferred if AcHFA comprises 1 or 2 double bonds, preferably one double bond. Double bonds are preferably located on the 6th, 9th, 12th or 15th
    BE2019 / 5602 carbon atom, counting (as usual) from the carboxylic acid group. Most preferably, a double bond is located on the 9th carbon atom.
    In highly preferred embodiments, AcHFA is represented by structure 2:
    a
    wherein n = 1, 2 or 3, preferably 2 or 3, most preferably 3; m = 1 or 2, preferably 2;
    one of A and B is OH, and the other of A and B is OAc.
    Also for structure 2, the double bond can have a cis or trans configuration (depicted by the line format. ' ΜΜηηηΜΛ ., Which indicates that the orientation of a single carbon-carbon bond extending from a double carbon-carbon bond can be in any direction ), but preferably the configuration is cis. The acid group in structure 2 may be in neutral form as shown, but may also be in ionic or salt form as defined above.
    In highly preferred embodiments, AcHFA is represented by structure 3:
    where one of A and B is OH, and the other of A and B is OAc. In these embodiments, AcHFA is (cis or trans; RR, SS, RS, or SR) 12-acetoxy-13hydroxyoctadec-9-enoic acid (3a), or (cis or trans; RR, SS, RS, or SR) 13 acetoxy-12-hydroxyoctadec -9-enoic acid (3b):
    BE2019 / 5602
    By mixing beer with limited fermentation and regular beer, the amount of AcHFA in regular beer is reduced by dilution. The amount of foam-negative factors in the beer obtained by the present process can be kept at acceptably low levels. This has a positive effect on foaming, in particular foam stability. In addition, the amount of AcHFA can be reduced, such as by adsorption on a zeolite, a hydrophobic adsorbent, or a hydrophilic adsorbent, as described in the co-pending patent application cited above. This results in a beer with less than 2 mg / l AcHFA, preferably less than 1.5 mg / l AcHFA, preferably less than 1.0 mg / l, more preferably less than 0.5 mg / l, still more preferably less than 0.25 mg / l. Beer with lower amounts of AcHFA has improved foam stability.
    When the present method is carried out on a medium comprising a mixture of beer with limited fermentation and regular beer, the medium is preferably a mixture of (only) beer with limited fermentation and regular beer. The volumetric ratio between the limited fermentation beer and the regular beer is preferably 1:99 99: 1, preferably 5:95 - 50:50. Distillation of a mixture at this ratio has been found to be the presence of several
    BE2019 / 5602 optimizes flavor compounds, wort-like flavors, sugars and foam factors, as described herein.
    The above-mentioned method results in a low-alcohol or non-alcoholic beer with an improved taste. The beer obtained has an ethanol content of 0 - 1.0% by volume. The ethanol content of the beer obtained by the present process may be less than 0.5% by volume, preferably less than 0.2% by volume, more preferably less than 0.1% by volume.
    In preferred embodiments, the total of 2methylpropanal, 2-methylbutanal, 3-methylbutanal, 3methylthiopropionaldehyde, and phenylacetaldehyde (“Strecker aldehydes”) in the resulting beer is less than 50 pg / l. The total of 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, 3-methylthiopropionaldehyde, phenylacetaldehyde, hexanal, trans-2-nonenal, benzaldehyde and furfural ("total aldehydes") is preferably less than 80 pg / l.
    In highly preferred embodiments, the beer obtained comprises • an amount of 2-methylpropanal of less than 18 pg / l, preferably less than 10 pg / l, more preferably 2-10 pg / l, and / or • a amount of 2-methylbutanal of less than 3.8 pg / l, preferably 0.2 - 2.5 pg / l, and / or • an amount of 3-methylbutanal of less than 14 pg / l, preferably 1 - 10 pg / l, and / or • an amount of 3-methylthiopropionaldehyde of less than 10 pg / l, preferably 2-8 pg / l, and / or • an amount of phenylacetaldehyde of less than 20 pg / l, preferably 1 - 8 pg / l.
    In preferred embodiments, all Strecker aldehydes are present in these preferred amounts.
    BE2019 / 5602
    Preferably, the total sugar content of the obtained NA beer, defined as the total of glucose, fructose, sucrose, maltose, and maltotriose, is at least 0.2 g / 100 ml. Preferably, the total sugar content is relatively low, such as a maximum of 3 g / 100 ml, preferably a maximum of 2 g / 100 ml. In preferred embodiments, the total sugar content is 0.5 - 2.0 g / 100 ml, preferably 1.2 - 2.0 g / 100 ml.
    The beer obtained preferably comprises at least 0.2 g / 100 ml of maltotriose. Preferably, the beer further comprises at least 0.05 g / 100 ml of glucose and / or at least 0.05 g / 100 ml of fructose. It is further preferred if the total sugar content of the beer obtained comprises 50-100% by weight of maltose, preferably 50-80% by weight, more preferably 50-65% by weight. The maltose content of the final beer is preferably at least 0.5 g / 100 ml.
    The method disclosed here results in a low-alcohol or non-alcoholic beer that has an optimized aldehyde to sugar ratio. Preferably, the total weight of Strecker aldehydes relative to maltose is less than 15 pg / g maltose, and the total aldehyde weight, relative to maltose, is less than 90 pg / g maltose, preferably less than 50 pg / g maltose . A lower preferred limit of the total weight of Strecker aldehydes to maltose is 0.01 µg / g maltose, preferably 0.1 µg / g maltose. A lower preferred limit of total aldehydes, relative to maltose, is 0.1 µg / g maltose, preferably 0.5 µg / g maltose. In particular, the weight of 2-methylpropanal, relative to maltose, is between 0.1 and 11, preferably between 0.2 and 5, more preferably between 0.25 and 2 µg / g maltose; and / or • the weight of 2-methylbutanal, relative to maltose, is between 0.05 and 6, preferably between 0.1 and 2.5, more preferably between 0.1 and 0.5 µg / g maltose ; and / or
    BE2019 / 5602 • the weight of 3-methylbutanal, relative to maltose, is between 0.05 and 25, preferably between 0.1 and 16, more preferably between 0.12 and 2 µg / g maltose; and / or • the weight of 3-methylthiopropionaldehyde, relative to maltose, is between 0.1 and 5, preferably between 0.2 and 4, more preferably between 0.25 and 0.8 µg / g maltose; and / or • the weight of phenylacetaldehyde, relative to maltose, is between 0.1 and 10, preferably between 0.2 and 5, more preferably between 0.45 and 2.8 µg / g maltose.
    In a highly preferred embodiment, the weight of 2-methylpropanal, relative to maltose, is between 0.1 and 11, preferably between 0.2 and 5, more preferably between 0.3 and 2 µg / g maltose .
    In another highly preferred embodiment, the weight of 2-methylbutanal, relative to maltose, is between 0.05 and 6, preferably between 0.1 and 2.5, more preferably between 0.1 and 0, 5 µg / g maltose.
    In another highly preferred embodiment, the weight of 3-methylbutanal, relative to maltose, is between 0.05 and 25, preferably between 0.1 and 16, more preferably between 0.12 and 2 pg / g maltose.
    In another highly preferred embodiment, the weight of 3-methylthiopropionaldehyde, relative to maltose, is between 0.1 and 5, preferably between 0.2 and 4, more preferably between 0.25 and 0.8 µg / g maltose.
    In another highly preferred embodiment, the weight of phenylacetaldehyde, relative to maltose, is between 0.1 and 10, preferably between 0.2 and 5, more preferably between 0.45 and 2.8 pg / g maltose.
    The beer obtained from the distillation preferably comprises ethyl 2-methylpentanoate, such as in an amount of at least 0.001 pg / l, at
    BE2019 / 5602 preferred 0.001 - 1000 pg / l, which ensures that the beer obtained has an improved taste, compared to other non-alcoholic or non-alcoholic beers, due to the masking effect of the ethyl-2-methylpentanoate root flavor. refreshing taste it imparts to the final beer. The amount of EMP in the NA beer is at least 0.001 pg / l, preferably at least 0.004 pg / l, more preferably at least 0.01 pg / l, even more preferably 0.1 pg / l. Preferred amounts of EMP are 0.1 - 1000 pg / l, preferably 1 - 800 pg / l, more preferably 10 - 500 pg / l. In preferred embodiments, the amount of EMP is 50-600 pg / l.
    The beer obtained from the distillation preferably comprises 1 - 20 pg / l, preferably 1.5 - 5 pg / l ethyl propanoate, which is important for imparting flavor. It is an advantage of the present process that the esters ethyl 2-methylpentanoate and ethyl propanoate remain in the beer at least in part during distillation.
    The beer obtained from the distillation further preferably comprises 0.05-30 mg / l ethyl acetate, preferably 0.1-15 mg / l ethyl acetate, more preferably 0.1-1 mg / l. Dis is also important for imparting flavor. The beer obtained from the distillation further preferably comprises isoamyl acetate in an amount of 0.05-7.5 mg / l, preferably 0.08-4.5 mg / l. Isoamyl acetate makes an important contribution to the taste of beer.
    A preferred beer obtained by the present method further comprises 20 - 250 mg / l of free amino nitrogen (FAN), more preferably 50 - 200 mg / l, more preferably 75 - 150 mg / l. Free amino nitrogen, as used herein, refers to the total amount of free amino compounds as determined by the NOPA method. This method results in quantification of primary amino compounds, such as free amino acids, small peptides and ammonia. The amount of FAN cited is an important aspect of the final taste and color of beer.
    BE2019 / 5602
    A preferred beer obtained by the present method further comprises less than 5 mg / l acetaldehyde, preferably less than 3 mg / l. This is important for the flavor profile of the beer obtained.
    In optional embodiments, the beer can be further flavored with a flavoring agent, as is known in the art. Suitable flavoring components can be, for example, different esters, acids and higher alcohols.
    Advantages of the present beer are reduced flavor intensity, because the beer has a less predominant taste, in particular less sweetness and less wort-like taste. The present beer is less sweet, and has favorable aldehyde levels even over this reduced sweetness. The result of this is that with less sweetness and flavor intensity, the beer is not considered wort-like, and consumers are not saturated by the taste after just a few glasses of beer. In addition, the beer is generally considered to be less thick and more refreshing. Thus, a beer of the present invention is more drinkable than existing non-alcoholic or low-alcohol beers.
    For the purpose of clarity and brief description, features are described herein as part of the same or separate embodiments, however, it will be well known that the scope of the invention may include embodiments with combinations of all or some of the features described.
    The invention will now be further illustrated by the following non-limiting examples.
    Methods
    Determination of aldehydes in beer using fiber derivatization, solid phase microextraction and gas chromatography mass spectrometry.
    BE2019 / 5602
    Sample preparation
    Under a CO2 atmosphere, 30.0 g of beer sample was weighed into a 40 ml bottle. With a 50 μΐ gastight syringe, 30 μΐ of internal standard solution was added to each sample. Then, still under a CO2 atmosphere, two 10 ml gas space bottles were filled with 4.0 g of the sample. Thus, the beer sample was analyzed in duplicate.
    Derivatization procedure
    A stock solution of about 200 mg / L of 0- (2,3,4,5,6-pentafluorobenzyl) -hydroxylamine (PFBHA) in deionized water was prepared. A standard 20 ml clear glass crimp-cap gas-clearing vial was charged with 14 g of the PFBHA solution. Then, an SPME fiber (Supelco) was placed in the gas chamber of the derivatization vial for 10 minutes at 30 ° C to impregnate the PDMS / DVB phase of the SPME fiber with the derivatizing agent. The SPME fiber infused with PFBHA was then placed in the gas space of a beer sample (4.0 g in 10 ml vial, filled under a CO2 atmosphere) leading to PFBHA derivatives of the aldehydes of interest. The extraction conditions were chosen at 30 ° C for 30 minutes.
    GC conditions
    An Agilent 7890A gas chromatograph, equipped with a “split-splitless” inlet, was used for this method. Optimal separation of the PFBHA / aldehyde compounds was achieved with a 30 m x 0.25 mm x 0.25 μm VF17MS column (Agilent). Some compounds co-elute, but in these cases the selectivity of the MS could circumvent the need for chromatographic separation. Certain aldehydes can coelute, but the mass spectrometer focuses on selective ions for each compound.
    BE2019 / 5602
    Helium at 1 ml / min is used as the carrier gas. A split ratio of 5 used to optimize peak width and sensitivity. The oven was programmed to 50 ° C (2 minutes) with a 10 ° C / min rise to 230 ° C, followed by a 30 ° C / min rise to 290 ° C (2 minutes hold).
    MS conditions
    The Agilent 5975C MSD was set for negative chemical ionization (NCI).
    For all aldehydes targeted by this methodology, a suitable ion fragment was chosen. In most cases, a compound-specific fragment was chosen instead of the most common fragment. This allows the selective determination of the target compounds of interest. In most cases, the molecular ion Mw minus m / z 20 (loss of H-F) is most suitable.
    Since most of the PFBHA-aldehyde compound consists of two peaks (syn- and anti-), the peak areas are added. Quantification of all aldehyde compounds was possible by setting appropriate calibration curves based on standard Heineken beer addition.
    Determination of ester compounds in beer using Stir Bar Sorptive Extraction and gas chromatography - mass spectrometry
    Due to the large concentration range of the analytes, the samples must be analyzed twice using different GCMS methods; one for the determination of compounds with high concentrations, and one for the compounds with low concentrations. The difference between the two methods is the mode of operation of the mass selective detector. The amount of extract injected is adapted to the mode of operation of the detector, as is known in the art. Isoamyl acetate was determined using the
    BE2019 / 5602 method for high concentrations, and ethyl acetate was determined using the low concentration method.
    Sample preparation
    In duplicates, 30.0 g of beer sample was weighed into a 40 ml bottle. Using a 50 μΐ gastight syringe, 30 μΐ of internal standard solution was added to each sample. A pure and already conditioned twister was then added to each sample. A 60-position stir plate was used to extract the samples. Extraction time is one hour. In order to prevent the formation of light-induced compounds, the samples are covered. Instrument conditions
    The Agilent 7890B gas chromatograph was coupled to an Agilent 5977A MSD. Sample entry is performed by a Gerstel MPS2-XT robot, in combination with a TDU-2 thermal desorption unit and CIS-4 controlled temperature inlet (both from Gerstel). The main capillary column was a 50m x 0.25mm x 0.25pm DB-5MS UI. Helium at 1.5 ml / min was used for carrier gas. The thermal desorption of the twisters was performed in solvent vent mode, which collects the eluents at -20 ° C on a tenax filled liner. During the heating step, the injector switched to a split ratio of 100: 1 and 6: 1 for the high and low concentration process, respectively. The oven was programmed at 40 ° C (2 minutes) with a 10 ° C / min rise to 280 ° C (1 minute hold). The MSD was set for scan mode (33,300 m / z) in the high concentration method, and in single ion mode for the low concentration method.
    Quantification of all compounds was made possible by the preparation of calibration curves (standard addition to a suitable matrix beer, (eg Heineken beer)). All calibrations are performed in both alcoholic and 0.0% alcoholic drinks.
    BE2019 / 5602
    Determination of sugar content in wort, beer and cider
    Sugar content was measured by Ultra Performance Liquid Chromatography (UPLC). UPLC can conveniently be performed at a temperature of 65 ° C. A suitable choice for the eluent is a mixture of acetonitrile / water, for example in a volume ratio of 75/25. The detector used is typically a Refractive Index (RI) detector. The sugar content of a sample was determined by comparing the UPLC curve of the sample with calibration curves of standard samples with known sugar concentrations.
    The samples for UPLC were prepared as follows. A beer or wort sample was diluted a factor of 5 by adding acetonitrile / water mixture (50/50 - equal parts by volume). If present, CO2 was removed prior to dilution (e.g., by shaking or stirring the sample). After dilution, the sample was filtered to obtain a clear solution. The filtered sample was injected into the UPLC at 65 ° C using the above eluent.
    Determination of free amino nitrogen (FAN)
    The amount of free amino nitrogen (such as amino acids, small peptides and ammonia) was measured according to the "Nitrogen by OPhthaldialdehyde Assay" (NOPA) method. The NOPA method was performed using a photometric analyzer (eg, Gallery ™ Plus Photometric Analyzer). According to the NOPA method, a test sample is subjected to treatment with orthophthalaldehyde [orthophthalialdehyde] (OPA) and N-acetylcysteine (NAC). This treatment results in the derivatization of primary amino groups present in the test sample to form isoindoles. The content of the isoindoles is then determined using the photometric analyzer at a wavelength of 340 nm. The free amino nitrogen (expressed in mg FAN / 1) can then become
    BE2019 / 5602 calculated on the basis of the measured content of the isoindoles. If necessary, the beer or wort sample is first subjected to centrifugation before analysis to clarify the sample and / or to a CO2 removal step (e.g. by stirring or shaking the sample).
    Determination of ethanol in beer
    The ethanol content was measured using a photometric analyzer (eg, Gallery ™ Plus Photometric Analyzer). The test sample is subjected to an enzymatic method, in which the ethanol contained in the sample is converted into acetaldehyde with alcohol dehydrogenase (ADH). The acetaldehyde content is then determined using the photometric analyzer at a wavelength of 340 nm. The ethanol content can be calculated on the basis of the acetaldehyde content. If necessary, the beer or wort sample is first centrifuged before analysis to clarify the sample and / or subjected to a CO2 removal step (e.g. by stirring or shaking).
    Example 1
    Multi-media distillation including limited fermentation beer
    A cold contact fermented beer and a regular beer were obtained by well known methods. The regular beer was a lager, which can be obtained commercially. Wort, as a comparative example, was obtained as known in the art.
    A continuous vacuum distillation device was provided which can process beer at a rate of 4 hl / hour. The apparatus included a preheater, a degassing system, two vacuum distillation columns including a condenser, an evaporator, and a plate heat exchanger cooling system. The device also included a carbonation system. The plant was set to deliver 90 mbar absolute pressure, resulting in a temperature of 43 ° C in the vacuum distillation columns.
    BE2019 / 5602
    Media comprising, as a beer with limited fermentation, the cold-contact fermented beer were subjected to distillation. The distilled media were wort (comparative), cold contact fermented beer (CC), and mixtures of cold contact fermented beer and regular beer (LB) in different volumetric proportions. The amounts of various aldehydes, esters and sugars were determined before and after distillation. The results are shown in Table 1.
    The results show that the amount of aldehydes is reduced by the distillation. Distillation of CC, 50/50 LB / CC, 80/20 LB / CC and 90/10 LB / CC results in reduction of Strecker aldehydes to 20, 40, 67 and 76% of the amount prior to distillation, respectively. The same examples show reduction of total aldehydes to 7, 11, 19 and 22% of the amount prior to distillation, respectively. From the results, it is clear that aldehydes can be effectively removed from a medium comprising beer with limited fermentation by distillation, and that this removal functions somewhat less efficiently in mixtures comprising ethanol. The slightly lower efficiency is advantageous because small threshold amounts of aldehydes are important for imparting the beer flavor. The results further show that it is beneficial to carry out the distillation on a mixture of regular beer and beer with limited fermentation, for example to obtain FAN levels that cannot otherwise be obtained, or to incorporate esters from a natural fermentation source including ethyl 2-methylpentanoate and ethyl propanoate.
    BE2019 / 5602
    3 / CC after 3.64 (48.7%) 1.38 (49.2%) 1.45 (37.2%) 3.83 (125.5%) 7.03 (128.3%) 60'0 (52.3%) 17.98 HH X O00 oo O1X5ooooO O o 0005O i — 1 ÜJ CO Qi >£<NCOco1X5O ι-d © ^© ^ © ^© ^© ^00CO© ^ 05 i — 1 00 1X5 05 05<N CD £ «_ O <N tF 1X5 00 τ— | Tt < CO^ H CO 05O O CO co, co. 1X5CDO(M or M-1X O CN Fh£ · ^Ocooo1X5 O O oOCNco1X5ooCN cc 00 >0500Tji 1X5O 1—1* 5 ^ © ^© ^© ^© ^© ^© ^ O CD 00 co 00 oo 1X5 1X5 OCO 1X5 00 O after qq CN, CN (26 q 00 00 (77 O O 22. w Xco O1X5 1X5 FhO000500 05- o o o05[>1X51—1 O 1X5 >i — 1COXCD1X5O CO 1X5X ©X ©X ©X ©X © © ^© ^© ^© ^© ^ 1X5 © ^ 05 CN 05 00 [* <· 00 £>, —1 1X5 CD Ooo 1X5 ^ - | ^ - | (N (N1 (N O O1X5, OT — 1 i — 1 1X5CD iS O 00 co O [>105 1 05 O00OCDO o o00ooO(NO<N 1X5 C> >i — 11X5i — 1T — 1T — 1O 1X5 xO *X after q x © '© ^00 0.91 X ' © ^ œ xS 00 xp '© ^ œ xS 22.01 O 1X5 (16.7 ° / 0.21 (11.99 29.04 ooTt <05OTj < 57 Si o oqq2.5 alsoOoq 50.>(N00coTbCD1—1 O 6060 zLzL Φ ^ H d ^ —1^ —1 >> O CDCDCD OO " Λ CDCD O Z! «5 O bio 60 Fh s i — you ” CD ±. zLΦ• fH & XXSö Φzi. Φ^ H X XX O <H Sh IjXa ITSωΦ with §withwithH nyla Sexai cH3 H Q <N <N05E cS œ
    BE2019 / 5602
    (12.9%) 0.01(98.8%) 0.22(55.3%) 17.34(76.3%) 35.65(21.8%)0.000.21 0.10 00Ό0.01 0.41 22.72 163.194.900.15 0.07 00Ό (12.0%) 0.01(91.4%) 0.26(60.1%) 18.01(66.5%) 40.52(19.1%)0.020.29 0.13 0.000.01 0.43 27.08 212.214.360.21 0.09 00Ό (7.6%) 0.02(105.7%) 0.26(86.8%) 13.47(39.8%) 36.65(10.9%)00Ό0.43 0.18 00Όo ó 0.30 33.84 335.88co0.30 0.13 00Ό %) 0.03(108.0%) 0.25(66.0%) 11.58(20.2%) 43.71(7.1%)0.000.47 0.16 0.13co q ó 0.38 57.24 613.06q ó0.41 0.14 OO (3.9%) 0.14(92.6%) 0.24(7.6%) 37.28(15.7%) 66.91 (6.7%)00'00.44 O 0.100.15 3.13 237.44 993.090.100.36 0.15 0.02trans-2-nonenal (gg / l) benzaldehyde (gg / l) sum of Strecker(pg / i) sum of total aldehydes (gg / l)Ethanol (vol.%)Glucose (g / 100ml) Fructose (g / 100ml) Sucrose (g / 100 ml)
    BE2019 / 5602
    0.75 0.39 1.450.23 2.8 66Ό 0.1730.55 0.30 1.0730.82q 6.0394 3.91 O 0.44 q0.35 3.6 2.12 O109 1.1 0.81 0.34 1.4526.89 125.3 103.65 5.5485 3.68 1.69 0.55 2.85O (N 0.54 90Ό5> 0.6 1.30 0.42 2.1616.75 74.2 67.59 3.7871 2.63 2.20 0.64 3.600.046.17 q Ó80 O 2.01 0.59 3.250.14 2.5 CO 60Όco 2.35 2.10 0.62 3.420.04 2.3 0.24 0.0100 0.02 1.58 0.47 2.59oi 13.2 15.98 0.9363 0.43 Maltose (g / 100 ml) Maltotriose (g / 100 ml) Total sugars (g / 100ml)ethyl acetate (mg / 1) ethyl propanoate (pg / l) ethyl butanoate (pg / l) isoamyl acetate (mg / 1)free amino nitrogen(mg / 1) acetaldehyde (mg / 1)
    BE2019 / 5602
    Example 2
    Comparison of the beer obtained with commercially available non-alcoholic or low-alcohol beers
    A beer obtained using the present method was compared to existing non-alcoholic beers by a tasting group of 17 skilled panelists. Beers were evaluated for specific taste characteristics, including sweetness, wort-like taste and total flavor intensity, as well as other flavor notes. For each characteristic, the observed intensity was indicated on a line scale. All panelists evaluated all beers for all characteristics, and results were averaged. The results are shown in Table 2.
    A beer obtained by the present method has a less wort-like taste and less sweet taste, and a lower flavor intensity, and therefore a less predominant taste, than commercially available non-alcoholic or low-alcohol beers. Thus, the likelihood of consumers getting satiated with the taste in just a few beers is lower. In addition, the beer is generally considered to be less thick, and more refreshing. For this reason, the present beer is considered to be more drinkable than existing commercially available non-alcoholic or low-alcohol beers.
    commercially available beer E38 16 12 17 10 5 36 29 cn BEm commercially available beer D 23 33 20 15 CM CM 11 rd 43 cn 28 in 23 commercially available beer C 23 28 33 21 19 m 24 m 46 32 29 m 23 commercially available beer B 26 42 18 12 rs00 O 45 35 32 CM 25 commercially available beer A 28 39 vH 14 ΙΛ CM 1044 33 32 m 25 current beer 1831 29 σι 11 14 CM 40 42 27 m 18 Table 2 Sweet taste Wort flavor Fruity / ester-like taste > Pear flavor > Taste of tropical fruit > Taste of green apple Hop flavor Vinegar flavor Total intensity Refreshing taste in the mouth Thick taste in the mouth Warm taste in the mouth Sweet aftertaste
    BE2019 / 5602
    权利要求:
    Claims (4)
    [1]
    1. applicant The applicant is hereby notified that the international search report and the written opinion of the International Searching
    I — I Authority have been established and are transmitted herewith.
    Filing of amendments and statement under Article 19:
    The applicant is entitled, if he so wishes, to amend the claims of the International Application (see Rule 46):
    When The time limit for filing such amendments is normally two months from the date of transmittal of the International Search Report.
    How Directly to the International Bureau of WIPO, 34 chemin des Colombettes
    1211 Geneva 20, Switzerland, Fascimile No .: (41-22) 338.82.70
    For more detailed instructions, see PCT Applicant's Guide, International Phase, paragraphs 9.004 - 9.011.
    A method of preparing beer with an ethanol content of 0-1.0% by volume, comprising • providing a medium with an ethanol content of 0-20% by volume, which medium comprises beer with limited fermentation;
    Subjecting said medium to a distillation step, whereby the amount of one or more aldehydes selected from the group consisting of 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, 3methylthiopropionaldehyde, phenylacetaldehyde, hexanal, trans-2nonenal, benzaldehyde and furfural in the medium is reduced, and thereby also, if present, the ethanol content is reduced to a content in the range of 0 - 1.0% by volume
    [2]
    2. I I The applicant is hereby notified that no international search report will be established and that the declaration under
    I — I Article 17 (2) (a) to that effect and the written opinion of the International Searching Authority are transmitted herewith.
    A method according to claim 1, wherein the distillation is carried out at a temperature of 10 - 100 ° C, preferably 20 - 65 ° C, most preferably 30 - 50 ° C, even more preferably 40 - 46 ° C.
    [3]
    3. I I With regard to any protest against payment of (an) additional fee (s) under Rule 40.2, the applicant is notified that:
    I I the protest together with the decision thereon has been transmitted to the International Bureau together with any
    I — I applicant's request to forward the texts of both the protest and the decision thereon to the designated Offices.
    I I no decision has been made yet on the protest; the applicant will be notified as soon as a decision is made.
    A method according to claim 1 or 2, wherein the distillation is carried out at a pressure of 0.01 - 500 mbar, preferably 1 - 200 mbar, most preferably 50 - 150 mbar, and even more preferably 80 - 110 mbar .
    A method according to any one of claims 1 to 3, wherein the medium comprises beer with limited fermentation and 1 - 15% by volume ethanol, preferably 2.5 - 10% by volume ethanol.
    A method according to any one of claims 1 to 4, wherein • the amount of 2-methylpropanal is reduced to less than 18 µg / L, preferably less than 10 µg / L, most preferably 2-10 µg / L; and / or • the amount of 2-methylbutanal is reduced to less than 3.8 µg / l, preferably 0.2-2.5 µg / l; and / or • the amount of 3-methylbutanal is reduced to less than 14 µg / l, preferably 1-10 µg / l; and / or
    BE2019 / 5602 • the amount of 3-methylthiopropionaldehyde is reduced to less than 10 µg / l, preferably 2-8 µg / l; and / or • the amount of phenylacetaldehyde is reduced to less than 20 µg / l, preferably 1-8 µg / l.
    A method according to any one of claims 1 to 5, wherein the total of 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, 3methylthiopropionaldehyde, and phenylacetaldehyde is reduced to less than 50 µg / l.
    A method according to any one of claims 1 to 6, wherein the total of 2-methylpropanal, 2-methylbutanal, 3-methylbutanal, 3methylthiopropionaldehyde, phenylacetaldehyde, hexanal, trans-2-nonenal, benzaldehyde and furfural is reduced to less than 80 gg / l.
    A method according to any one of claims 1 to 7, wherein the medium comprises beer with limited fermentation and regular beer, preferably a lower beer, most preferably a lager.
    A method according to any one of claims 1 to 8, wherein the limited fermentation beer and the regular beer are present in a volumetric ratio of 1:99 - 99: 1, preferably 5:95 - 50:50.
    A method according to any one of claims 1 to 9, wherein the beer with limited fermentation is a fermented beer obtained by limited ethanol fermentation of wort, resulting in an ethanol content of less than 1.0% by volume, such as a fermentation of wort characterized by a temperature below 7 ° C, preferably -1 - 4 ° C, such as -0.5 - 2.5 ° C, preferably for a period of 8 - 72 hours, more preferably 12 - 48 hours ( "Cold-contact fermented beer"); and / or • a short (eg less than 2 hours) fermentation time, which fermentation quickly stopped due to temperature inactivation, such as by rapid cooling to -0.5 - 1 ° C, optionally followed by subsequent pasteurization ("beer with stopped fermentation" ); and / or
    BE2019 / 5602 • fermentation by a yeast strain producing relatively low amounts of ethanol under the fermentation conditions used, such as for example a yeast strain producing less than 0.2 g ethanol per gram fermentable sugar in the wort, preferably less than 0.1 g ethanol per grams of fermentable sugar, with suitable strains (e.g., Crabtree negative strains) known in the art, and the amount of ethanol produced under varying fermentation conditions can be determined by routine experiments ("yeast limited beer"); and / or • fermentation using a first ethanol-producing yeast strain, in the presence of a sufficient amount of a second yeast strain consuming ethanol, such as Saccharomyces rouxii, to consume essentially all ethanol produced by the first yeast strain; and / or • wort with a fermentable sugar content such that a maximum of 1.0% by volume of alcohol is produced upon completion of the fermentation, the wort usually having a fermentable sugar content of less than 17.5 g / l, at preferably less than 12 g / l, more preferably less than 8 g / l (“low-sugar wort beer”).
    11. A beer with an ethanol content of 0-1.0% by volume with:
    a) a total sugar amount, defined as the total of glucose, fructose, sucrose, maltose, and maltotriose, of at least 0.2 g / 100 ml; and
    b) a total of Strecker aldehydes, defined as the total of 2methylpropanal, 2-methylbutanal, 3-methylbutanal, 3methylthiopropionaldehyde, and phenylacetaldehyde, less than 50 pg / l; and / or with
    a) less than 18, preferably less than 10 µg / L 2-methylpropanal, preferably 2-10 µg / L;
    b) less than 3.8 µg / L 2-methylbutanal, preferably 0.2-2.5 µg / L;
    c) less than 14 pg / l 3-methylbutanal, preferably 1 - 10 pg / l;
    BE2019 / 5602
    d) less than 10 µg / l 3-methylthiopropionaldehyde, preferably 2-8 µg / l;
    e) less than 20 pg / l phenylacetaldehyde, preferably 1 - 8 pg / l, the total weight ratio of 2-methylpropanal, 2methylbutanal, 3-methylbutanal, 3-methylthiopropionaldehyde, and phenylacetaldehyde, relative to maltose, less than 15 pg / g maltose.
    A beer according to claim 11, wherein the total of aldehydes, defined as the total of 2-methylpropanal, 2-methylbutanal, 3methylbutanal, 3-methylthiopropionaldehyde, phenylacetaldehyde, hexanal, trans-2-nonenal, benzaldehyde and furfural less than 80 pg / l is.
    A beer according to claims 11 or 12, wherein the sugar content comprises 50-100 wt% maltose.
    A beer according to any one of claims 11-13, further comprising an amount of less than 2 mg / l AcHFA, wherein AcHFA is a C12-C22 fatty acid, comprising a carboxylic acid group and a C11-C21 linear alkyl group, which alkyl group may be partially unsaturated and which alkyl group is substituted with at least one hydroxyl group and at least one acetate group.
    A beer according to any of claims 11-14, further comprising at least 0.001 µg / l ethyl 2-methylpentanoate.
    A beer according to any one of claims 11-15, further comprising 20-250 mg / l free amino nitrogen (FAN), more preferably 50-200 mg / l, more preferably 75-150 mg / l.
    A beer according to any one of claims 11-16, further comprising less than 5 mg / l acetaldehyde, preferably less than 3 mg / l.
    2019/5602
    PATENT COOPERATION TREATY
    From the INTERNATIONAL SEARCHING AUTHORITY
    To:
    Jansen, C.m.
    V.O.
    Carnegieplein 5
    2517 KJ The Hague
    PAYS-BAS
    PCT
    NOTIFICATION OF TRANSMITTAL OF
    THE INTERNATIONAL SEARCH REPORT AND THE WRITTEN OPINION OF THE INTERNATIONAL SEARCHING AUTHORITY, OR THE DECLARATION
    Applicant's or agent's file reference P120407PC00
    International application No.
    PCT / NL2018 / 050589
    Applicant
    HEINEKEN SUPPLY CHAIN B.V.
    (PCT Rule 44.1)
    Date of mailing (day / month / year)
    8 May 2019 (08-05-2019)
    FOR FURTHER ACTION See paragraphs 1 and 4 below
    International filing date (day / month / year)
    September 10, 2018 (10-09-2018)
    [4]
    4. Reminders
    The applicant may submit comments on an informal basis on the written opinion of the International Searching Authority to the International Bureau. These comments will be made available to the public after international publication. The International Bureau will send a copy of such comments to all designated Offices unless an international preliminary examination report has been or is to be established.
    Shortly after the expiration of 18 months from the priority date, the international application will be published by the International Bureau. If the applicant wishes to avoid or postpone publication, a notice of withdrawal of the international application, or of the priority claim, must reach the International Bureau before the completion of the technical preparations for international publication (Rules 90 £> /s.1 and 905 / S.3).
    Within 19 months from the priority date, but only in respect of some designated Offices, a demand for international preliminary examination must be filed if the applicant wishes to postpone the entry into the national phase until 30 months from the priority date (in some Offices even later); otherwise, the applicant must, within 20 months from the priority date, perform the prescribed acts for entry into the national phase before those designated Offices. In respect of other designated Offices, the time limit of 30 months (or later) will apply even if no demand is filed within 19 months. For details about the applicable time limits, Office by Office, see www.wipo.int/pct/en/texts/time_limits.html and the PCT Applicant's Guide, National Chapters.
    Within 22 months from the priority date, the applicant may request that a supplementary international search be carried out by a different International Searching Authority that offers this service (Rule 45 £> /s.1). The procedure for requesting supplementary international search is described in the PCT Applicant's Guide, International Phase, paragraphs 8.006-8.032.
    Name and mailing address of the International Searching Authority

    European Patent Office, P.B. 5818 Patentlaan 2 NL-2280 HV Rijswijk
    Tel. (+ 31-70) 340-2040
    Fax: (+ 31-70) 340-3016
    Authorized officer
    BUTER, Johannes
    Tel: +31 (0) 70 340-2901
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US20120207909A1|2009-01-08|2012-08-16|Kirin Beer Kabushiki Kaisha|Unfermented beer-flavored malt beverage having reduced unpleasant wort flavor and method for producing the same|
    EP2385100A1|2010-05-07|2011-11-09|Anheuser-Busch InBev S.A.|Low alcohol or alcohol free beer and method for producing it|
    CN105007762A|2013-03-12|2015-10-28|朝日啤酒株式会社|Method for producing non-alcoholic beer-flavored malt beverage|
    法律状态:
    2020-05-29| FG| Patent granted|Effective date: 20200409 |
    优先权:
    申请号 | 申请日 | 专利标题
    PCT/NL2018/050589|WO2020055236A1|2018-09-10|2018-09-10|Low-alcohol beer|
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