Method for preparing a beverage component comprising volatile thiols, beverage component obtained by

专利摘要:
A method for preparing a beverage component, the method comprising the steps of: (a) providing an aqueous hop suspension comprising hopping or hop derivatives, the hopping or hop derivatives comprising thiol precursors; (b) treating the hop suspension in vitro with an enzyme or enzyme mixture with beta-lyase activity.
公开号:BE1025839B1
申请号:E2017/5945
申请日:2017-12-15
公开日:2019-07-30
发明作者:Jacques Gros
申请人:Anheuser-Busch Inbev S.A.；
IPC主号:

专利说明:

Method for preparing a beverage component comprising volatile thiols, beverage component obtained by such method and use of such beverage component
BACKGROUND OF THE INVENTION
The present invention relates to a beverage component comprising volatile thiols derived from hopping or hop derivatives, and a method for preparing such beverage component. BACKGROUND OF THE INVENTION
Drooghoppen is a well-known practice in beer production for adding aromas to beer. Hopping and in particular aromatic hop varieties contain a large amount of flavor components that are separated from the beer during late or dry hopping and provide the beer with a specific flavor profile in the form of volatile and fragrant components.
A disadvantage of the dry hop process is the relatively low yield of flavor components. That is why large quantities of hops are needed to effectively flavor the beer.
Research has shown that hops contain much more flavor components than those that are separated from beer during dry hopping. However, a large proportion of the flavor components are chemically bound to entities in the hops and / or are present as aroma precursors in a non-volatile and non-odorous form that must be released and / or converted into a volatile and odorous form resulting in the effective
BE2017 / 5945 flavoring beer. These hop aroma precursors can be chemically classified into two main types: Conjugates of thiol and glycoside conjugates of aglycones.
Conversion of S-conjugate precursors and glycoside conjugate precursors into, respectively, volatile and fragrant thiols and aglycones can be carried out by beer yeast in the fermentation tank, but in the case of adding hops to the fermentation tank at a late stage of fermentation or even during maturation, as is customary in dry hop processes, no or insufficiently viable yeast is present to perform an effective conversion of the hop aroma precursors. If aromatic hops were added at an earlier stage of fermentation if sufficient viable yeast is present, it is believed that the biotransformation of yeast releases less than 5% of the available hop aromas.
It will be clear from the above that there is still a market need for improving the efficiency and, perhaps more importantly, the potential of dry hopping in terms of the diversity of the type and amount of flavorings to be added to beer. Summary of the invention
The present invention addresses the aforementioned market need by providing a method that provides the ability to unlock an entire class or set of currently overlooked aromas that are provided to the beer during dry hopping. This invention is defined in
BE2017 / 5945 the appended claims. Preferred embodiments are defined in the dependent claims. In particular, the present invention relates to a method for preparing a beverage component, the method comprising the steps of:
(a) providing an aqueous hop suspension comprising hops or hop derivatives, the hops or hop derivatives comprising thiol precursors;
(b) treating the hop suspension in vitro with an enzyme or enzyme mixture with betalyase activity
The aqueous hop suspension can be a hop in beer suspension prepared by directly adding the hops or hop derivatives in the fermentation or maturing tank or can be prepared in-situ at the beer production site or ex-situ in a hop conversion facility by adding hops or hop derivatives to water or a beer-like aqueous solution.
It is preferred to add pyridoxal phosphate to the aqueous hop suspension and / or to select an enzyme or enzyme mixture comprising gamma glutamyl transpeptidase.
In a preferred method of the invention, the suspended hops or hop derivatives are treated with the enzyme or enzyme mixture for a period of at least 10 minutes at a temperature ranging between 5 ° C and 72 ° C, preferably between 15 ° C and 42 ° C and / or at a pH between 3.2 and 8.5.
The aqueous suspension preferably has an alcohol concentration of at least 0.01% by volume
BE2017 / 5945 preferably at least 3 vol% and most preferably at least 5 vol%.
The hop or hop derivatives are preferably selected from the group comprising aromatic hop cultivars or dual-purpose hop cultivars, in particular from one or more of the following hop varieties: Sorachi Ace, Nelson Sauvin, Tomahawk, Citra, SAAZ, Mozaik, Centennial.
The method preferably comprises a step of filtering or centrifuging the suspension after enzyme treatment to obtain a retentate and a permeate, and collecting the permeate as the aforementioned beverage component. This permeate can then be used as an ingredient in beverage or food production or can be further concentrated or fractionated to obtain purified flavor components.
The present invention further relates to a beverage component comprising at least one or more of the following components:
(a) 3-sulfanylhexane-1-ol;
(b) 3-sulfanylhexyl acetate;
(c) 4-sulfanyl-methylpentane-2-one;
(d) 3-sulfanyl-4-heptane-1-ol;
(e) 3-sulfanylheptylacetate;
characterized in that the total concentration of the combined components (a) + (b) + (c) + (d) + (e) is at least 200 ppt or at least three of the components (a) to (e) ) are present in a concentration of at least 5 ppt.
The present invention also relates to the use of the above defined
BE2017 / 5945 beverage component as a dry-hop ingredient or as an ingredient for addition to a malt-based beverage such as beer, including non-alcoholic (> 0.05% ABV) or low-alcoholic beer (> 0.5% ABV) or cider-based beverage.
Definitions
Hops or hop derivatives are defined herein as all types of hop products known to impart aromas to beer and include whole hop bubbles, hop extracts, hop oils, hop resins as well as pelletized or otherwise compacted hops or hop products.
Hops or hop derivatives comprising all or a large part of the hop oils of the original hop bubbles are preferred.
Also preferred are hopping or hop derivatives that result from so-called aromatic hop cultivars or double-purpose hop cultivars
Ace, Nelson
Sauvin, Tomahawk
Detailed description of a preferred embodiment
The present invention focuses in particular on the digestion of S-conjugates of thiol, by allowing efficient conversion of the
Sconjugates bound to hops or hop derivatives in volatile and fragrant aromas that enrich the organoleptic profile of the beer.
It has been established that in the chemical route of converting S-conjugates to volatile and fragrant thiols, the conversion of cystein-bound thiols to volatile thiols is an important bottleneck.
BE2017 / 5945
It has been found that when treating a suspension of aqueous hops or hop derivatives with an enzyme or enzyme mixture exhibiting a beta-lyase activity, the efficiency of converting S-conjugates into polyfunctional thiols that give beer a taste can be increased.
It is preferred to add pyridoxal phosphate (e.g., PLP 30) to the aqueous hop suspension as a co-factor for the betalyase activity.
Sufficiently high beta lyase activity is achieved by providing the enzyme or enzyme mixture in a manner that the enzyme or enzyme mixture is readily available from binding substrate, in particular by providing the enzyme or enzyme mixture in vitro wherein the enzyme ( or the enzymes of the enzyme mixture are not (are) in microbiological cells, but are (are) freely suspended in the aqueous hop suspension. In that case, the cysteine-conjugate is efficiently converted to a volatile thiol by the enzyme (s).
It is believed that the conversion efficiency can be further improved when the aqueous hop suspension is treated with an enzyme or enzyme mixture with gamma glutamyl transpeptidase activity prior to or simultaneously with treatment with the beta lyase. If the enzyme or enzyme mixture with the gamma glutamyl transpeptidase activity also exhibits aminopeptidase, dipeptidase and / or carboxypeptidase activity, the conversion efficiency can be even further improved.
BE2017 / 5945
During operation, the hops or hop derivatives are preferably suspended in water, in beer or in a beer-like solution to obtain a solution with [concentration] and treated with the enzyme or enzyme mixture for a period of at least 10 minutes at a temperature varying between
5 ° C and 72 ° C Bee preferably between 15 ° C and 42 ° C. It pH range from the solution Bee preferred enforced in a range between 3.2 and 8.5 during the
therapy. After treatment, the suspension is preferably filtered and / or centrifuged to obtain a retentate and a permeate, and to collect the permeate as a beverage component that can be added to green beer or a matured beer as a concentrated hop aroma solution.
The aqueous suspension preferably has an alcohol concentration of at least 0.01% by volume, preferably at least 3% by volume and most preferably at least 5% by volume.
The method according to the invention allows the preparation of a beverage component comprising one or more of the following components:
(a) 3-sulfanylhexane-1-ol;
(b) 3-sulfanylhexyl acetate;
(c) 4-sulfanyl-methylpentane-2-one;
(d) 3-sulfanyl-4-heptane-1-ol;
(e) 3-sulfanylheptylacetate;
wherein the total concentration of the combined components (a) + (b) + (c) + (d) + (e) comprises at least 200 ppt or wherein at least three of said
BE2017 / 5945 components (a), (b), (c), (d) and (e) present a concentration of at least 5 ppt.
The beverage component of the invention can be used to prepare a beverage by adding the beverage component to another beverage component or diluent 1/3 to 1/30, such as, for example, a hop ingredient during beer or cider production. As an example, one could use a beverage component according to the invention by mixing it with a so-called beer concentrate and a diluent. The beverage component can also be added to a finished beverage such as hop water, malt water, fruit juices, beer or cider-based, including non-alcoholic (> 0.05% ABV) or low-alcoholic drinks (including beers) (> 0.5% ABV).
The beverage component according to the invention can also be further concentrated, fractionated or purified by means of chromatography, adsorption, distillation or other selective concentration techniques which are known in the art for obtaining one or more purified or concentrated components (a) to (e) which can be used as a flavor component in food, in particular drinks such as beer or cider, or other industries.
Examples
Example 1
Hop variety: Citra liter of hydro-alcoholic medium (10% ABV) pyridoxal 5-phosphate (0.1 mM).
g of hops was suspended in the hydroalcoholic medium.
BE2017 / 5945 mg beta lyase (75-150 units / mg) (in vitro) was added to the hop suspension and the suspension was kept at 28 ° C for 30 minutes, with continuous stirring at 100 rpm. The pH of the solution was 7.7.
After 30 minutes, the suspension was filtered through a filter, whereby the solid hop material was removed and the permeate was found to include:
(a) w% 3-sulfanylhexane-1-ol;
(b) w% 3-sulfanylhexyl acetate;
(c) w% 4-sulfanyl-methylpentane-2-one;
(d) w% 3-sulfanyl-4-heptane-1-ol;
(e) w% 3-sulfanylpentan-1-ol wherein the total concentration of the combined components (a) + (b) + (c) + (d) + (e) was more than 500 ppt.
Example 2
Hop variety: Centennial liter of hydroalcoholic medium (10% ABV) pyridoxal 5-phosphate (0.1 mM) g of hop pellets were suspended in the hydroalcoholic medium.
mg of gamma-glutamyl transpeptidase (35-60 units / mg) and 40 mg of carboxypeptidase (50-120 units / mg) were added to the suspension (in vitro) and the suspension was incubated at 28 ° C for 3 minutes with continuous stirring at 100 rpm. The pH of the suspension was 7.3.
BE2017 / 5945
After 30 minutes, the suspension was centrifuged at 500 rpm for 10 minutes and 950 ml of supernatant was collected.
Then 50 mg beta-lyase (75-150 units / mg) was added to the supernatant in vitro and the mixture was stored at 28 ° C for 30 minutes with continuous stirring at 100 rpm. The pH of the mixture was 7.3.
After 30 minutes, the mixture was filtered through a filter whereby the solid hop material was removed and the permeate (the beverage component) was found to include:
(a) w% 3-sulfanylhexane-1-ol;
(b) w% 3-sulfanylhexyl acetate;
(c) w% 4-sulfanyl-methylpentane-2-one;
(d) w% 3-sulfanyl-4-heptane-1-ol;
(e) w% 3-sulfanylpentan-1-ol wherein the total concentration of the combined components (a) + (b) + (c) + (d) + (e) was more than 1200 ppt.
Example 3
Hops Variety: Mosaik liter of beer or cider (5% ABV) - pyridoxal 5-phosphate (0.1 mM) g hop concentration was suspended in 1 liter of beer or cider (5% ABV) - pyridoxal-5 phosphate (0.1 mM) mg beta lyase (75-150 units / mg) was added to the supernatant in vitro and the mixture was kept at 24 ° C for 40 minutes with continuous stirring at 50 rpm. (pH 7.3)
BE2017 / 5945
After 30 minutes, the mixture was filtered through a filter whereby the solid hop material was removed and the permeate (the beverage component) was found to include:
(a) w% 3-sulfanylhexane-1-ol;
(b) w% 3-sulfanylhexyl acetate;
(c) w% 4-sulfanyl-methylpentane-2-one;
(d) w% 3-sulfanyl-4-heptane-1-ol;
(e) w% 3-sulfanylpentan-1-ol wherein the total concentration of the combined components (a) + (b) + (c) + (d) + (e) is more than 200 ppt.

权利要求:
Claims (14)
[1]
A method for preparing a beverage component, the method comprising the steps of:
(a) providing a hop suspension comprising hops or hop derivatives, aqueous hops or hop derivatives comprising thiol precursors;
(b) treating the hop suspension in vitro with an enzyme or enzyme mixture with betalyase activity
[2]
A method according to claim 1, comprising the step of adding pyridoxal phosphate to the aqueous hop suspension.
[3]
The method of claim 1, wherein the enzyme or enzyme mixture has gamma glutamyl transpeptidase.
[4]
Method according to any of the preceding claims, wherein the suspended hops or hop derivatives are treated with the enzyme or enzyme mixture for a period of at least
[5]
The method according to any of the preceding claims, wherein the suspended hops or hop derivatives are treated with the enzyme or enzyme mixture at a pH ranging between 3.2 and 8.5.
[6]
The method of any one of the preceding claims, wherein the aqueous suspension has an alcohol concentration of at least 0.01% by volume.
[7]
A method according to any one of the preceding claims, wherein the hop or hop derivatives are preferably selected from the group comprising aromatic
BE2017 / 5945 hop cultivars or double-purpose hop cultivars, in particular from one or more of the following hop varieties: Sorachi Ace, Nelson Sauvin,
Tomahawk,
Citra, SAAZ, Mozaik, Centennial, Cascade.
[8]
A method according to any one of the preceding claims, comprising filtering or centrifuging the suspension after enzyme treatment to obtain a retentate and a permeate, and collecting the permeate as said beverage component.
[9]
9.- Beverage component comprising at least one or more of the following components:
(a) 3-sulfanylhexane-1-ol;
(b) 3-sulfanylhexyl acetate;
(c) 4-sulfanyl-methylpentane-2-one;
(d) 3-sulfanyl-4-heptane-1-ol;
(e) 3-sulfanylheptylacetate;
wherein the total concentration of the combined components (a) + (b) + (c) + (d) + (e) is at least 200 ppt; or wherein at least three of said components (a), (b), (c), (d) and (e) are present in a concentration of at least 5 ppt.
[10]
The beverage component of claim 9, comprising 5 ppt of three or more of the following components:
(a) w% 3-sulfanylhexane-1-ol;
(b) w% 3-sulfanylhexyl acetate;
(c) w% 4-sulfanyl-methylpentane-2-one;
(d) w% 3-sulfanyl-4-heptane-1-ol;
(e) w% 3-sulfanylheptylacetate;
BE2017 / 5945 where the total concentration of the combined components (a) + (b) + (c) + (d) + (e) is at least 200 ppt.
10 minutes at a temperature ranging between 5 ° C and
72 ° C, preferably between 15 ° C and 42 ° C.
[11]
11. - Use of a beverage component as identified in any one of claims 9-10 or as prepared by a method as identified in any one of claims 1-8 for preparing a beverage by adding the beverage component to another beverage component or diluent .
[12]
12. Use of a beverage component as identified in any one of claims 9-10 or as prepared by a method as identified in any one of claims 1-8 as a hop ingredient during beer or cider production.
[13]
13.- Use according to claim 11 or 12, encompassing it adding the beverage component to a finished beer or a finished one cider; and / or before or after filtration from the beer or the cider; and / or while
fermentation; and / or during maturation of the beer or cider.
[14]
A method according to any of claims 1 to 8, comprising the step of concentrating or fractionating the beverage component.

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同族专利:

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公开号 | 公开日

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AR110342A1|2019-03-20|

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BE1025839A1|2019-07-23|

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WO2018109186A1|2018-06-21|

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EP3336166A1|2018-06-20|

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法律状态:
2019-08-28| FG| Patent granted|Effective date: 20190730 |

优先权:

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申请号 | 申请日 | 专利标题

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EP16204231.1A|EP3336166A1|2016-12-15|2016-12-15|Method for preparing a beverage component comprising volatile thiols, beverage component obtained by such method and use of such beverage component|

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EP16204231.1|2016-12-15|

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