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WO1997033971A1 - Compositions constituees de sels d'acides de houblon solides - Google Patents

Compositions constituees de sels d'acides de houblon solides Download PDF

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Publication number
WO1997033971A1
WO1997033971A1 PCT/US1997/004070 US9704070W WO9733971A1 WO 1997033971 A1 WO1997033971 A1 WO 1997033971A1 US 9704070 W US9704070 W US 9704070W WO 9733971 A1 WO9733971 A1 WO 9733971A1
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WO
WIPO (PCT)
Prior art keywords
acids
potassium salts
hhia
dhia
microns
Prior art date
Application number
PCT/US1997/004070
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English (en)
Inventor
James A. Guzinski
Larry J. Stegink
Original Assignee
Kalamazoo Holdings, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kalamazoo Holdings, Inc. filed Critical Kalamazoo Holdings, Inc.
Priority to AU22123/97A priority Critical patent/AU2212397A/en
Publication of WO1997033971A1 publication Critical patent/WO1997033971A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C5/00—Other raw materials for the preparation of beer
    • C12C5/02—Additives for beer
    • C12C5/026—Beer flavouring preparations
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C3/00—Treatment of hops
    • C12C3/12—Isomerised products from hops
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C9/00—Methods specially adapted for the making of beerwort
    • C12C9/02—Beerwort treatment; Boiling with hops; Hop extraction
    • C12C9/025—Preparation of hop extracts ; Isomerisation of these extracts; Treatment of beerwort with these extracts; Surrogates of the hop

Definitions

  • isoalpha acids Four types are used in the art of brewing. These consist of the conventional unreduced isoalpha acids (IA) and three hydrogenated forms thereof: dihydro, also called rho (DHIA), tetrahydro (THIA), and hexahydro (HHIA) .
  • IA unreduced isoalpha acids
  • DHIA dihydro
  • THIA tetrahydro
  • HHIA hexahydro
  • the hydrogenated forms are made by the reduction of the alpha, isoalpha, and beta acids, by procedures practiced in commerce.
  • IA formed during normal wort boil of hops or hop extract, or by iso erization outside the kettle, becomes "light struck” with the formation of odors pronounced of a skunk.
  • Hydrogenated forms of IA are: DHIA: forms less foam, less bitter than IA, light stable. THIA: forms more foam than IA, about twice as bitter, light stable.
  • HHIA forms more foam than IA, about as bitter, light stable.
  • Each analogue is present as six major forms: cis and trans, each with three different alkyl chains on the position two carbon.
  • a mixture of DHIA and HHIA may therefore contain twelve different forms, each of which can exist as mixtures of optically active isomers. This means that twenty-four different structures are potentially present in a mixture of DHIA and HHIA.
  • Lupofresh (D.T. Pat. No. 2,919,232) discloses a solid, granular isohumulate which can be added to wort as is, or from which IA can be extracted for addition to beer.
  • mixtures of these hop acid analogues in commercial brewing, so as to take advantage of the distinguishing properties of each one.
  • a mixture of IA and HHIA may be used, IA being cheaper than HHIA, but HHIA contributing superior foam.
  • a mixture of DHIA and HHIA, or DHIA and THIA, or all three may be used in various ratios to achieve given foam, cling, and mouth feel properties in a given beer.
  • the desired combination will depend upon the protein, alcohol, and per-cent of non-fermented carbohydrates in the beverage, since the properties of the analogues are affected by the levels of these other constituents.
  • hop bitter acids When used in the brewhouse, these hop bitter acids are in the form of their potassium salts in aqueous solution, sometimes containing propylene glycol. Maximum commercial concentrations are limited by solubility characteristics.
  • the preferred aqueous preparations commercially available are as follows: IA-30%; DHIA-35%; THIA-10%. HHIA is not available, since its maximum non-precipitating aqueous solution is only 5%.
  • IA and THIA preparations may separate into two phases, the lower phase being a more concentrated gum, and the upper a more dilute aqueous solution. In the case of IA and THIA, these gums can be reincorporated by gentle warming and stirring. Unlike IA and THIA, the 35% commercial preparations of DHIA will often form crystals of DHIA upon standing at ambient temperatures. The crystals of DHIA will not readily redissolve and, when formed, require prolonged heating at elevated temperatures to redissolve. Unless redissolved, they are unavailable to the beer.
  • HHIA does not form solutions in water of practical concentration. Although solutions of 10% or more may be made by heating, they crystallize over time at ambient temperature and require reheating to 80-90°C. for prolonged periods to effect dissolution.
  • the present invention provides commercially useful concentrated preparations of DHIA and HHIA which are stable as well as easily used in the brewhouse. It also provides stable concentrated mixtures thereof with IA and THIA. Practical concentrations of hop acids of 50% to 60% are achieved by this invention, the upper concentration being limited by viscosity, which in turn limits pour- ability. This reduces the amount of plastic requiring disposal or recycling, as well as shipping and warehouse costs.
  • the invention avoids the hazards associated with prolonged heating at near-boiling temperatures and of handling scalding solutions in the brewhouse, as well as the danger of rupture of the polypropylene container during heating.
  • a particular object is the provision of compositions containing potassium salts of the hop isoalpha acids DHIA and/or HHIA in a non-supersaturated aqueous solution of potassium salts of the same hop isoalpha acids, which are useful for the aforesaid purpose.
  • Another object of the invention is to provide such compositions which are readily convertible to a single- phase solution upon heating to a moderate temperature with agitation for a short time, thereby providing a convenient composition for the introduction of hop isoalpha acids, and especially these particular hop isoalpha acids, into the brew.
  • a still further object of the invention is the provi- sion of a process for the production of such compositions.
  • a composition comprising a mixture of irregularly- shaped particles of compounds selected from potassium salts of dihydroisoalpha acids (DHIA) and potassium salts of hexahydroisoalpha acids (HHIA) in a liquid at least partially aqueous alkaline solution of potassium salts of the corresponding DHIA or HHIA, which solution is non- supersaturated with respect to the potassium salts of dihydroisoalpha acids (DHIA) or potassium salts of hexahydroisoalpha acids (HHIA) present therein, the size of the particles on their greatest dimension being not more than 250 microns, such a composition which also contains hop essential oil, such a composition wherein the size of the particles on their greatest dimension is not more than 25 microns, and preferably not more than about 10 microns, such a composition containing particles of potassium salts of both dihydroisoalpha acids (DHIA) and hexahydro ⁇ isoalpha acids (HHIA), such a
  • a process for forming irregularly-shaped microparticles of compounds selected from potassium salts of dihydroisoalpha acids (DHIA) and potassium salts of hexahydroisoalpha acids (HHIA) in which the particles are not more than 250 microns on their greatest dimension in a liquid at least partially aqueous solution which is non- supersaturated with respect to potassium salts of the corresponding DHIA or HHIA comprising the step of subjecting a starting at least partially aqueous solution which is supersaturated with respect to compounds selected from potassium salts of dihydroisoalpha acids (DHIA) and potassium salts of hexahydroisoalpha acids (HHIA) to agitation, thereby crystallizing out irregularly-shaped microparticles thereof, and maintaining the mixture at ambient temperature until particle formation ceases due to loss of supersaturation by the starting solution, such a process comprising the step of introducing microparticles of the corresponding compounds selected from potassium salts of dihydr
  • HHIA particles of potassium salts of both dihydroisoalpha acids (DHIA) and hexahydroisoalpha acids (HHIA) are produced
  • DHIA dihydroisoalpha acids
  • HHIA hexahydroisoalpha acids
  • microparticles of potassium salts of both dihydro ⁇ isoalpha acids (DHIA) and hexahydroisoalpha acids (HHIA) are introduced into the solution to increase the rate at which supersaturation disappears, such a process wherein the crystal size of the resulting microparticles is reduced by mechanical means to eliminate crystals more than about 25 microns in size on their greatest dimension, such a process wherein the crystal size of
  • the liquid phase in contact with DHIA and/or HHIA be non-supersaturated with these constituents
  • the solid particles of DHIA and/or HHIA have a size not more than 250 microns on their greatest dimension, preferably not more than 25 microns, and even more preferably not more than about 10 microns on their largest dimension, and are irregular in shape
  • the liquid phase must be alkaline and the hop acids in both the liquid and solid phases must be present as their potassium salts.
  • Such a composition is heretofore unknown to the art. We have found that the single-phase solutions from which crystals of DHIA and HHIA form are supersaturated, and that at unpredictable times crystallization may be spontaneously initiated.
  • composition can then only be liquified by prolonged heating at temperatures in the range of 90°C.
  • the process for overcoming supersaturation preferably involves adding seed particles to a supersaturated solution, thereby initiating formation of microparticles in the supersaturated solution.
  • the seed may be prepared by the reduction of crystal size from the large crystals, which develop in the DHIA and HHIA solutions now commer- cially available, to microcrystals of not greater than 250 microns, and preferably not greater than 25 microns in size.
  • the seed may be a previously-prepared micropar- ticle suspension.
  • the present invention has its greatest present utility in overcoming the deficiencies of aqueous solutions, but it is equally applicable to such solutions which also contain propylene glycol and/or glycerine.
  • DHIA Dihydro—isoalpha acids
  • THIA tetrahydro—isoalpha acids
  • HHIA hexahydro—isoalpha acids
  • IA isoalpha acids
  • HHIA and 10% THIA was prepared. It required heating to 80°C. and stirring for several hours to dissolve the crystals which were present. This mixture was separated into three portions.
  • the second portion was seeded with crystals of the potassium salts of HHIA and THIA acids having a maximum dimension of less than 25 microns, made as above, and stirred for 24 hours at ambient. A large quantity of micro ⁇ particles formed. This portion was stored at room tempera ⁇ ture for two months. Examination under a microscope revealed that the particles were less than about 250 microns and most were less than 25 microns in size. The microparticles occurred in a mixture of shapes unlike the shapes of the parent seed crystals: platelets, irregular needles, irregular rhomboids, and amorphous solids were observed. This mixture completely dissolved when heated to 58°C for five minutes with gentle agitation.
  • Example (IA) The third portion of the original supersaturated mixture was stored at room temperature for two months. During this time a thick layer of crystals of the hop acids formed, as in Example (IA) above. This portion was then milled to reduce the particle size to less than 25 microns. The mixture was then stirred at room temperature for 24 hours. During the stirring time, there was a large increase in the number of visible particles. Microscopic examination of the particles showed a mixture of different particle types as in Example IB. The mixture completely dissolved when heated to 60°C. for five minutes with gentle stirring. This solid-liquid mixture containing microparticles is, like the product of Example IB, very easy to use in a brewery.
  • Example 2 A soluble mixture of reduced hop bitter acids of 45% concentration.
  • a mixture of 20% DHIA, 20% HHIA and 5% THIA was dissolved at 90°C. in alkaline water with the pH adjusted to
  • Example 3 A mixture of reduced hop bitter acids with propylene glycol, a common edible adjuvant.
  • the mixture from Example 2 was diluted by the addition of 5% by weight of propylene glycol. There was no change in appearance of the mixture except for a decrease in viscosity. This mixture redissolved upon warming similarly to the mixture of Example 2, from which it was derived.
  • a cosolvent such as propylene glycol or glycerine can be used as part of the composition if reduction of viscosity or freezing point is desirable. A minor proportion of such solvent, e.g., less than about 40% by volume of the aqueous solution, is preferred.
  • Example 4 A mixture containing HHIA with high solubility.
  • HHIA is a mixture of six major forms of the acids, differing in alkyl side chains and being present as cis and trans isomers. It contains optical isomers of all these forms. Rapid crystallization or precipitation may not allow fractional crystallization and separation of analogs and isomers, thereby inhibiting the formation of crystals with uniform surfaces which are resistant to redissolution. Surprisingly, the microparticles did not have the same sharp edges as the original, ground, seed crystals.
  • a 1% HHIA solution was made by diluting the mixture in 19 parts of distilled water to which sufficient dilute potassium hydroxide had been added to increase the pH to 11.0. Although fine particles were visible at ambient temperature, all the particles promptly dissolved when the 1% dilution was heated to about 50 to 55°C. In contrast, the parent large crystals, when added to alkaline water so as to effect a 1% concentration, did not dissolve at 75 C C. when stirred for four hours.
  • Example 5 shows that microparticles of HHIA can be made without seeding, in practice seeding is desirable to assure that supersaturation does not occur. Furthermore, it has been observed that the rate of micro- particle formation, in the absence of seeding, is unpre- dictable. Therefore seeding is preferred in practice. Example 5.
  • aqueous solution was made containing 50% IA and 33% glycerine at a pH of 9.2, using aqueous KOH.
  • One part by weight of this solution was added to one part of the microparticle-containing mixture of Example IB.
  • This gave a mixture containing 25% IA, 10% HHIA, 5% THIA and 16.5% glycerine, the glycerine effectively reducing the viscos ⁇ ity.
  • This microparticle-containing mixture promptly dissolved at 59°C. and, when so dissolved, readily and completely dissolved in pH 10 water to form a convenient 1% solution of hop acids.
  • Such a composition enables a brewer to use a highly concentrated product for both bitterness and improved foam.
  • Example 6 This Example also demonstrates the use of the novel products of microparticulate hop acids when added to and used in conjunction with a hop acid that does not readily form crystals or solid particles. Commercial 30% IA is not known to form crystals, although separation of the hop acid as a thick gum from refrigerated product is common.
  • Example 6 A mixture of microparticulate and liquid hop bitter acids containing hop oil. An aqueous mixture was made containing 20% HHIA, 10%
  • hop oil is entrained in the microparticles, adsorbed on the surface of the particles, hydrophobically bonded to dissolved hop acids, or otherwise held in the mixture, the hop oil does not separate out and can, therefore, be incorporated into beer simultaneously with the hop acids.
  • This provides a convenient, novel, and useful form of total hop flavor, both bitterness and aroma, in brewery applications.
  • Example 7
  • This product was milled, using procedure known to the art, to reduce particle size to essentially less than 250 microns, with an average particle size of 23 microns. It was agitated for a day, a sample withdrawn, and agitation continued for another two days. Viscosity increased as more microparticles formed.
  • the liquid-solid mixture contained 29.8% hop acids, the same as the original assay.
  • a high performance liquid chro atogram (HPLC) of the solids showed a distribution of analogues and isomers of HHIA different from the original supersaturated mixture, with only a trace of THIA.
  • the solids had irregular shapes and did not show clean linear crystal faces.
  • the analysis of particle size was performed on a Lasentec MlOO FBRM (Focused Beam Reflectance Measurement) System. Focal depth was set at 0.0 (focused at the windows) for all measure ⁇ ments. The stirrer was set at 500, and measurements were made at ambient temperature. Distributions were reported as unweighted mean chord lengths. Particle sizes are considered to be two-thirds of the measured chord length, an approximation considered valid for systems of particles which are roughly spherical in shape.
  • Example 8 A 51.3% mixture of DHIA microparticles in a non-supersaturated solution of DHIA.
  • a 51.3% non-supersaturated solution of DHIA was prepared by heating it to 85°C. in water, with the pH adjusted to 9.2 with KOH. This solution became supersatur ⁇ ated upon cooling, but did not immediately form solids. Upon stirring at ambient for four days, it became opales ⁇ cent with the appearance of liquid crystals in a mother liquor. Examination under a microscope showed that it contained a mixture of particle shapes. Some particles had the appearance of needles, a few of about 25 microns in length, but most less than 10 microns in length. The majority of the particles were amorphous, with an average largest dimension of less than 10 microns. The mixture was stable over a six-week period, the microparticles being so small that little settling was observed.
  • Example 9 Direct Dosing of microparticulate mixtures into beer.
  • Example 7 The 30% THIA-HHIA microparticle mixture of Example 7 was diluted to 1% in pH 10 water at ambient temperature, forming a hazy solution. This was immediately dosed into a beer in a clear glass bottle at a rate to add 15 ppm of hop acids to the beer. The bottle was recapped and inverted to mix the injecta, which made the beer hazy. It was then pasteurized. Upon removal from pasteurization it had become clear, and remained clear upon cooling to ambient.
  • Hop acid crystals were removed from the bottom of the warehouse-stored containers of Example 7. 10 mg of these crystals were added to a bottle of the beer used above, the bottle recapped, and pasteurized. The crystals had not gone into solution, and could be seen suspended in the beer.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Engineering & Computer Science (AREA)
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  • Genetics & Genomics (AREA)
  • Food Science & Technology (AREA)
  • Wood Science & Technology (AREA)
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Abstract

Compositions contenant sous forme de microparticules des sels de potassium des acides isoalpha de houblon réduits, DHIA et/ou HHIA, dans une solution aqueuse non sursaturée de sels de potassium des mêmes acides isoalpha de houblon, pouvant également contenir d'autres acides isoalpha de houblon tels que IA et/ou THIA, qu'on peut facilement transformer en une solution en une seule phase en la chauffant à température modérée avec agitation pendant une durée brève, ce qui donne une composition adaptée à l'introduction de ces acides de houblon particuliers dans une bière sans les inconvénients que présentent les compositions utilisées jusqu'à présent pour effectuer cette introduction, et procédé de production de ces compositions.
PCT/US1997/004070 1996-03-15 1997-03-14 Compositions constituees de sels d'acides de houblon solides WO1997033971A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU22123/97A AU2212397A (en) 1996-03-15 1997-03-14 Solid hop acid salt compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US61666896A 1996-03-15 1996-03-15
US08/616,668 1996-03-15

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Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000052212A1 (fr) * 1999-03-05 2000-09-08 Haas Hop Products, Inc. Methode de controle des micro-organismes dans un procede en milieu aqueux
WO2000053814A1 (fr) * 1999-03-05 2000-09-14 Betatec Hopfenprodukte Gmbh Procede de lutte contre des micro-organismes dans un milieu de processus aqueux contenant du sucre
WO2001006877A1 (fr) * 1999-07-27 2001-02-01 Rhodia Inc. Compositions antibacteriennes a base d'acides de houblon
WO2000065632A3 (fr) * 1999-04-22 2001-02-15 Miller Brewing Procede de decontamination de la levure
US6475537B1 (en) 2000-07-27 2002-11-05 Rhodia Inc. Hops acid antibacterial compositions
US6521796B2 (en) 2000-02-25 2003-02-18 Kalamazoo Holdings, Inc. Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same
WO2004072291A3 (fr) * 2003-02-10 2005-11-10 Haas Inc John I Utilisation d'acides de houblon dans la production d'ethanol combustible
WO2007130736A1 (fr) 2006-05-04 2007-11-15 S.S. Steiner, Inc. Améliorations du goût amer de la bière
US7361374B2 (en) 2002-05-17 2008-04-22 S.S. Steiner, Inc. Application for hop acids as anti-microbial agents
EP2015762A4 (fr) * 2006-03-29 2010-07-28 Haas John I Compositions antimicrobiennes comprenant des sels alcalins d'acide de houblon et leurs utilisations
US8414934B2 (en) 2008-02-08 2013-04-09 John I. Haas, Inc. Compositions and methods for arachnid control
US9545110B2 (en) 2013-01-07 2017-01-17 John I. Haas, Inc. Compositions and methods for controlling a honey bee parasitic mite infestation
US11229211B2 (en) 2018-05-14 2022-01-25 John I. Haas, Inc. Compositions and methods for controlling a honey bee parasitic mite infestation
US12054697B2 (en) 2021-01-22 2024-08-06 John I. Haas, Inc. Hop acids formulations and methods

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3765903A (en) * 1970-09-17 1973-10-16 Carton And United Breweries Lt Isomerised hop extract
US5200227A (en) * 1992-05-11 1993-04-06 Kalamazoo Holdings, Inc. Stable aqueous solutions of tetrahydro and hexahydro iso-alpha acids

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3765903A (en) * 1970-09-17 1973-10-16 Carton And United Breweries Lt Isomerised hop extract
US5200227A (en) * 1992-05-11 1993-04-06 Kalamazoo Holdings, Inc. Stable aqueous solutions of tetrahydro and hexahydro iso-alpha acids

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CONCISE ENCYCLOPEDIA CHEMISTRY, WALTER DE GRUYTER, New York, 1994, pp. 286-87. *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000053814A1 (fr) * 1999-03-05 2000-09-14 Betatec Hopfenprodukte Gmbh Procede de lutte contre des micro-organismes dans un milieu de processus aqueux contenant du sucre
US6893857B1 (en) * 1999-03-05 2005-05-17 Beta Tec Hopfenprodukte Gmbh Method for using hops acid for controlling microorganisms in a sugar-containing aqueous process medium
WO2000052212A1 (fr) * 1999-03-05 2000-09-08 Haas Hop Products, Inc. Methode de controle des micro-organismes dans un procede en milieu aqueux
WO2000065632A3 (fr) * 1999-04-22 2001-02-15 Miller Brewing Procede de decontamination de la levure
US6326185B1 (en) 1999-04-22 2001-12-04 Miller Brewing Company Method for decontaminating yeast
WO2001006877A1 (fr) * 1999-07-27 2001-02-01 Rhodia Inc. Compositions antibacteriennes a base d'acides de houblon
US6521796B2 (en) 2000-02-25 2003-02-18 Kalamazoo Holdings, Inc. Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same
US6583322B1 (en) 2000-02-25 2003-06-24 Kalamazoo Holdings, Inc. Dihydro and hexahydro isoalpha acids having a high ratio of trans to cis isomers, production thereof, and products containing the same
US6475537B1 (en) 2000-07-27 2002-11-05 Rhodia Inc. Hops acid antibacterial compositions
US7361374B2 (en) 2002-05-17 2008-04-22 S.S. Steiner, Inc. Application for hop acids as anti-microbial agents
US7910140B2 (en) 2002-05-17 2011-03-22 S.S. Steiner, Inc. Application for hop acids as anti-microbial agents
AU2004210945B2 (en) * 2003-02-10 2011-05-19 John I. Haas, Inc. Use of hop acids in fuel ethanol production
WO2004072291A3 (fr) * 2003-02-10 2005-11-10 Haas Inc John I Utilisation d'acides de houblon dans la production d'ethanol combustible
EP2015762A4 (fr) * 2006-03-29 2010-07-28 Haas John I Compositions antimicrobiennes comprenant des sels alcalins d'acide de houblon et leurs utilisations
EP2013327A4 (fr) * 2006-05-04 2009-09-23 Steiner Inc S S Améliorations du goût amer de la bière
WO2007130736A1 (fr) 2006-05-04 2007-11-15 S.S. Steiner, Inc. Améliorations du goût amer de la bière
AU2007248389B2 (en) * 2006-05-04 2011-12-01 S.S. Steiner, Inc. Improvements to the bittering of beer
US8414934B2 (en) 2008-02-08 2013-04-09 John I. Haas, Inc. Compositions and methods for arachnid control
US9545110B2 (en) 2013-01-07 2017-01-17 John I. Haas, Inc. Compositions and methods for controlling a honey bee parasitic mite infestation
US11229211B2 (en) 2018-05-14 2022-01-25 John I. Haas, Inc. Compositions and methods for controlling a honey bee parasitic mite infestation
US12054697B2 (en) 2021-01-22 2024-08-06 John I. Haas, Inc. Hop acids formulations and methods

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