Liquid brewing product and process

Abstract

The present disclosure describes a process of extracting liquid hop extracts from hops with water by vacuum steam distillation at temperatures below the boiling point of water. Also disclosed are liquid hop extracts, compositions comprising the liquid hop extracts, and products comprising the liquid hop extracts or compositions comprising the liquid hop extracts, such as beverages, pharmaceutical products and cosmetic products, are also described herein.

Description

LIQUID BREWING PRODUCT AND PROCESSTECHNICAL FIELD

[0001] The present disclosure relates to a process for preparing a liquid hop extract. The disclosure also relates to a liquid hop extract, a hop oil composition comprising the liquid hop extract, and products comprising the same, such as beverages, pharmaceutical products and cosmetic products.BACKGROUND ART

[0002] The four main ingredients in beer are malt, water, yeast, and hops. Hops are the flowers, also known as hop cones, of the plant species Humulus lupulus. Hops have been cultivated for centuries for use in beer production as they are known to help keep beer fresh over time, retain a head of foam, and add aroma and flavour (e.g. bitterness or “hoppiness”).

[0003] Typically, dried hops (in the form of dried hop cones or pellets) are added at a late stage in the brewing process to avoid the volatile compounds, attributed to hoppiness, from dispersing during the boil or fermentation (hot side) steps. Brewers can vary the amount of hops added to a brew based on the desired flavour-profile, resulting in beers with a strong hoppiness producing a lot of organic waste that must be filtered and disposed.

[0004] The use of wet hops (i.e. hop cones that haven’t been dried before use, also known as “wet-hopping”) is becoming more popular in beer brewing because of the resulting distinct flavour profiles. Wet-hopping is difficult because wet hops spoil quickly, therefore the hops usually must be used on the day of harvest. This presents a challenge for breweries that rely on the import of hop material, rather than self-harvest. One way to overcome the problems of organic by-product and wet-cone spoilage is to extract the components of the hops responsible for hoppiness and use these directly in the brewing process.

[0005] Hop extracts are an alternative product that overcomes some of the disadvantages of dry hops and wet hops. These contain concentrated flavour and / or bittering compounds and / or oils extracted from hops. Hop extracts are typically sold as a liquid that is simply added after the fermentation stage to impart a hop aroma and flavour to the beer, which provides greater ease-of-use compared to dry hops and wet hops. However, the aroma and flavour profile imparted by hop extracts is significantly different from that of dry hops or wet hops.

[0006] Hop extracts are often prepared by a CO2 extraction process involving extracting the hop material with supercritical CO2 at high pressures. Hop extracts prepared by CO2 extraction have a high concentration of alpha acids, e.g., between 25 and 60% depending on the hop variety. The high alpha acid concentration mean CO2 hop extracts are useful for impacting the bitterness of hops to a beer, but lack the complex flavour profile of dry hops or wet hops.

[0007] Another process used to extract hops is steam distillation. This process involves extracting hop material with steam, e.g. in a lavender pot. A variation of this process is vacuum steam distillation, which involves hop material with steam under vacuum at a low temperature. AU487788B describes a hop extract oil from the vacuum distillation of dry hops. The temperature in such extractions must be kept lower than 50°C to prevent the extraction of sulfur-containing compounds that would add an unwanted flavour and / or aroma profile of the resulting oil. Likewise, WO2023229977A1 describes a hop extract oil from a low temperature vacuum distillation process, wherein the temperature is typically kept below 30°C. Another alternative known in the art is to pre-process the hops by contact with organic solvents to obtain a solvated hop extract, which is then further subjected to a steam distillation step to give a purified hop oil (US3436319A).

[0008] Accordingly, it is an object of the present invention to go some way to avoiding the above disadvantages; and / or to at least provide the public with a useful choice.

[0009] Other objects of the invention may become apparent from the following description which is given by way of example only.

[0010] Any discussion of documents, acts, materials, devices, articles or the like which has been included in the present specification is solely for the purpose of providing a context for the present invention. It is not to be taken as an admission that any or all of these matters form part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed before the priority date.SUMMARY OF THE INVENTION

[0011] In a first aspect, the invention provides a process for preparing a liquid hop extract, the process comprising:a. charging a distillation vessel with hops and water,b. heating the water to a temperature of about 70 to 89°C at a reduced pressure to produce a water vapour,c. contacting the water vapour with the hops to produce a hop extract vapour, andd. condensing the hop extract vapour in a condenser to obtain a liquid hop extract comprising a hop oil and a hydrosol.

[0012] In at least one embodiment, the process for preparing a liquid hop extract further comprises:e. separating the hop oil and the hydrosol in the liquid hop extract obtained in step (d).

[0013] In at least one embodiment, the process for preparing a liquid hop extract further comprises:f. collecting the hop oil obtained in step (e) in a collection chamber.

[0014] In at least one embodiment, the hops are wet hop cones, dry hop cones, hop pellets or a mixture of any two or more thereof. In at least one embodiment, the hops are wet hop cones. In at least one embodiment, the hops are dry hop cones. In at least one embodiment, the dry hop cones comprise about 80 to 95% w / w dry matter. In at least one embodiment, the dry hop cones comprise about 85 to 92% w / w dry matter; preferably, about 89 to 91% w / w dry matter. In at least one embodiment, the hop pellets comprise about 80 to 95% w / w dry matter. In at least one embodiment, the hop pellets comprise about 85 to 92% w / w dry matter; preferably, about 89 to 91% w / w dry matter. In at least one embodiment, the wet hop cones comprise about 10 to 40% w / w dry matter. In at least one embodiment, the wet hop cones comprise about 20 to 30% w / w dry matter; preferably, about 20 to 25% w / w dry matter.

[0015] In at least one embodiment, the hops are a hop variety selected from Green Bullet, Motueka, Nelson Sauvin, NZ Cascade, Pacific Sunrise, Pacifica, Rakau, Riwaka, Southern Cross and a mixture of two or more thereof.

[0016] In at least one embodiment, the water is kept at a constant volume by inputting water into the apparatus from an external source.

[0017] In at least one embodiment, the hops and the water in step (a) are mixed together. In at least one embodiment, the distillation vessel comprises a single chamber, wherein the hops and water are mixed and heated in the single chamber.

[0018] In at least one embodiment, the hops and the water in step (a) are in separate chambers of the distillation vessel. In at least one embodiment, the distillation vessel comprises a lower chamber and an upper chamber, wherein the lower chamber is charged with the water and the upper chamber is charged with the hops and the water is heated in the lower chamber to produce the water vapour that flows from the lower chamber to the upper chamber and contacts the hops to produce the hop extract vapour. In at least one embodiment, the lower chamber and the upper chamber are separated by a porous separator (e.g., a mesh or grate). In at least one embodiment, the distillation vessel comprises a first chamber in fluid connection with a second chamber, wherein the first chamber is charged with the water and the second chamber is charged with the hops, and the water is heated in the first chamber to produce water vapour that flows to the second chamber and contacts the hops to produce the hop extract vapour.

[0019] In at least one embodiment, in step (b), the water is heated at a temperature sufficient to product water vapour at the reduced pressure. In at least one embodiment, in step (b) the water is heated to a temperature of about 75 to 89°C, about 80 to 89°C, or about 85 to 89°C. In at least one embodiment, in step (b) the water is heated to a temperature of about 87°C.

[0020] In at least one embodiment, before the process can proceed to step (d), a temperature measured at the top of the distillation vessel is about 45°C.

[0021] In at least one embodiment, during step (d), the temperature measure at the top of the apparatus is about 45 to 96°C. In at least one embodiment, during step (d), the temperature measure at the top of the distillation vessel is about 55 to 95°C. In at least one embodiment, during step (d), the temperature measure at the top of the distillation vessel is about 65 to 95°C. In at least one embodiment, during step (d), the temperature measure at the top of the distillation vessel is about 70 to 89°C.

[0022] In at least one embodiment, the process uses wet hops harvested about 0 to 48 hours prior.

[0023] In at least one embodiment, the reduced pressure in step (b) is between 0.01 to 1.00 bar below atmospheric pressure. In at least one embodiment, the reduced pressure used in step(b) is between about 0.05 to 0.80 bar below atmospheric pressure. In at least one embodiment, the reduced pressure used in step (b) is between about 0.10 to 0.70 bar below atmospheric pressure. In at least one embodiment, the reduced pressure used in step (b) is between about 0.15 to 0.6 bar below atmospheric pressure. In at least one embodiment, the reduced pressure used in step (b) is at least about 0.15 bar below atmospheric pressure. In at least one embodiment, the reduced pressure used in step (b) is at least about 0.2 bar, about 0.25 bar, about 0.3 bar, about 0.35 bar, about 0.4 bar, about 0.45 bar, or about 0.5 bar below atmospheric pressure. In at least one embodiment, the reduced pressure used in step (b) is at least about 0.3 bar below atmospheric pressure.

[0024] In at least one embodiment, the hops are compressed in the distillation vessel before step (b). In at least one embodiment, the hops are compressed until the hops are about 50 to 90%, or about 55 to 85%, or about 60 to 80%, or about 65 to 75% of the volume of the hops before compression. In at least one embodiment, the hops are compressed until the hops are about 65 to 75% the volume of the hops before compression. In at least one embodiment, the hops are compressed until the hops are about 70% the volume of the hops before compression.

[0025] In at least one embodiment, in step (b) the water is heated at a reduced pressure for about 0.5 to 3 hours. In at least one embodiment, in step (b) the water is heated at a reduced pressure for about 0.75 to 2 hours. In at least one embodiment, in step (b) the water is heated to a temperature of about 75 to 89°C, about 80 to 89°C, or about 85 to 89°C for about 0.5 to 3 hours. In at least one embodiment, in step (b) the water is heated to a temperature of about 87°C for about 0.5 to 3 hours. In at least one embodiment, in step (b) the water is heated to a temperature of about 75 to 89°C, about 80 to 89°C, or about 85 to 89°C for about 0.75 to 2 hours. In at least one embodiment, in step (b) the water is heated to a temperature of about 87°C for about 0.75 to 2 hours.

[0026] In at least one embodiment, step (b) comprises a two-stage heating protocol. In at least one embodiment, in the first stage the water is heated at a reduced pressure until the production of the hop extract vapour substantially slows.

[0027] In at least one embodiment, step (b) comprises a two stage heating protocol, wherein in the first stage the water is heated at a reduced pressure and in the second step the pressure is reduced by about 0.2 to 0.4 bar until the temperature of the water increases by about 5 to 10°C then the pressure is increased by about 0.2 to 0.4 bar to extract further hop oil into the extractvapour. In at least one embodiment, in the first stage the water is heated at a reduced pressure until the production of the hop extract vapour substantially slows.

[0028] In at least one embodiment, step (b) comprises a two stage heating protocol, wherein in the first stage heated at a reduced pressure and in the second step the pressure further reduced 0.2 to 0.4 bar to extract further hop oil into the extract vapour. In at least one embodiment, step (b) comprises a two stage heating protocol, wherein in the first stage heated at a reduced pressure of about 0.3 to 0.5 bar below atmospheric pressure and in the second step the pressure further reduced about 0.2 to 0.4 bar to extract further hop oil into the extract vapour.

[0029] In at least one embodiment, the condenser comprises cooling means, e.g. recirculated cool water.

[0030] In at least one embodiment, step (e) comprises separating the hop oil and the hydrosol in a separator column. In at least one embodiment, step (e) comprises conveying the liquid hop extract obtained in step (d) to a separator column, wherein the separator column comprises a collection port in fluid connection with the collection chamber such that when the liquid hop extract is conveyed into the separator column, the hop oil and hydrosol separate into an oil phase comprising hop oil and an aqueous phase comprising hydrosol and as the level of the oil phase rises, the oil phase flows through the collection port and into the collection chamber. In at least one embodiment, the separator column further comprises an outlet valve below the collection point, wherein the valve is in fluid connection with a hydrosol storage tank. In at least one embodiment, opening the outlet valve allows the liquid hop extract in the separator column to flow into the hydrosol storage tank.

[0031] In at least one embodiment, the liquid hop extract is conveyed from the condenser to the separator column.

[0032] In at least one embodiment, the hydrosol obtained in step (f) is conveyed to the hydrosol storage tank.

[0033] In at least one embodiment, the process further comprises:g. purifying the collected hop oil of step (f).

[0034] In at least one embodiment, step (g) comprises a freeze / thaw purification and / or filtration.

[0035] In a second aspect, the invention provides a hop oil extract obtained by the process of the first aspect.

[0036] In a third aspect, the invention provides a hop oil extract comprising at least about 75% myrcene.

[0037] In a fourth aspect, the invention provides a hop oil extract comprising less than about 1% alpha acids.

[0038] In at least one embodiment, the hop oil extract comprises myrcene.

[0039] In at least one embodiment, the hop oil extract comprises at least about 80% hop essential oils. In at least one embodiment, the hop oil extract comprises at least about 85%, about 90%, about 95%, about 98% or about 99% hop essential oils. In at least one embodiment, the hop oil extract comprises about 100% hop essential oils.

[0040] In at least one embodiment, the hop oil extract further comprises caryophyllene, farnesene, geraniol, linalool, humulene, or a combination of two or more thereof. In at least one embodiment, the hop oil extract comprises caryophyllene, farnesene, and humulene. In at least one embodiment, the hop oil extract comprises caryophyllene, farnesene, geraniol, linalool and humulene.

[0041] In at least one embodiment, the hop oil extract comprises at least about 76%, about 77%, about 78%, about 79%, about 80%, about 81%, about 82%, about 83%, about 84%, about 85%, about 86%, about 87%, about 88%, about 89%, about 90%, about 91%, or about 92% myrcene. In at least one embodiment, the hop oil extract comprises at least about 80% myrcene. In at least one embodiment, the hop oil extract comprises about 75 to 92% myrcene. In at least one embodiment, the hop oil extract comprises about 75 to 92%, about 80 to 92% or about 85 to 92% myrcene. In at least one embodiment, the hop oil extract comprises about 75 to 95%, about 80 to 95% or about 85 to 95% myrcene.

[0042] In at least one embodiment, the hop oil extract comprises about 0.1 to 10% caryophyllene. In at least one embodiment, the hop oil extract comprises about 0.1 to 5%, about 0.1 to 2%, or about 0.1 to 1% caryophyllene. In at least one embodiment, the hop oil extract comprises about 1 to 10% or about 1 to 5% caryophyllene. In at least one embodiment, the hop oil extract comprises less than about 10% caryophyllene. In at least one embodiment, the hop oil extract comprises less than about 5% caryophyllene.

[0043] In at least one embodiment, the hop oil extract comprises about 0.01 to 10% farnesene. In at least one embodiment, the hop oil extract comprises about 0.01 to 5%, about 0.01 to 4%, or about 0.01 to 2% famesene. In at least one embodiment, the hop oil extract comprises about 0.1 to 5%, about 0.1 to 4%, or about 0.1 to 2% famesene. In at least one embodiment, the hop oil extract comprises less than about 5% farnesene. In at least one embodiment, the hop oil extract comprises less than about 2% or less than about 1% farnesene.

[0044] In at least one embodiment, the hop oil extract comprises about 0.1 to 15% humulene. In at least one embodiment, the hop oil extract comprises about 0.1 to 10%, about 0.1 to 5%, about 0.1 to 2% or about 0.1 to 1% humulene. In at least one embodiment, the hop oil extract comprises about 1 to 15%, about 1 to 10% humulene. In at least one embodiment, the hop oil extract comprises less than about 10% humulene. In at least one embodiment, the hop oil extract comprises less than about 5% humulene. In at least one embodiment, the hop oil extract comprises less than about 2% or less than about 1% humulene.

[0045] In at least one embodiment, the hop oil extract comprises at least about 60% myrcene, about 0.1 to 10% caryophyllene, about 0.1 to 10% farnesene, and about 0.1 to 15% humulene. In at least one embodiment, the hop oil extract comprises at least about 80% myrcene, about 0.1 to 5% caryophyllene, about 0.1 to 5% farnesene, and about 0.1 to 5% humulene. In at least one embodiment, the hop oil extract comprises at least about 80% myrcene, less than about 5% caryophyllene, less than about 5% farnesene, and less than about 5% humulene.

[0046] In at least one embodiment, the hop oil extract comprises less than 1% alpha acids. In at least one embodiment, the hop oil extract comprises less than 0.1% alpha acids. In at least one embodiment, the hop oil extract is essentially free of alpha acids. In at least one embodiment, the hop oil extract comprises less than 1% iso-alpha acids. In at least one embodiment, the hop oil extract comprises less than 0.1% iso-alpha acids. In at least one embodiment, the hop oil extract is essentially free of iso-alpha acids. In at least one embodiment, the hop oil extract comprises less than 1% beta acids. In at least one embodiment, the hop oil extract comprises less than 0.1% beta acids. In at least one embodiment, the hop oil extract is essentially free of beta acids. In at least one embodiment, the hop oil extract comprises less than 0.1% alpha acids, less than 0.1% iso-alpha acids and less than 0.1% beta acids.

[0047] In at least one embodiment, the hop oil extract is obtained from wet hop cones, dry hop cones, hop pellets or a mixture of two or more thereof. In at least one embodiment, the hopoil extract is obtained from wet hop cones. In at least one embodiment, the hop oil extract is obtained from dry hop cones.

[0048] In at least one embodiment, the hop oil extract is obtained from a hop variety selected from Green Bullet, Motueka, Nelson Sauvin, NZ Cascade, Pacific Sunrise, Pacifica, Rakau, Riwaka, Southern Cross and a mixture of two or more thereof.

[0049] In at least one embodiment, the hop oil extract is obtained from wet hop cones, wherein hop oil extract is extracted from the wet hop cones within 0-48 hours of being harvested.

[0050] In at least one embodiment, the hop oil extract has a density of about 0.80 to 1.02 g / mL. In at least one embodiment, the hop oil extract has a density of about 0.85 to 1.01 g / mL. In at least one embodiment, the hop oil extract has a density of about 0.89 to 0.95 g / mL.

[0051] In a fifth aspect, the invention provides a hop oil composition comprising the hop oil extract of the third or fourth aspect and at least one solubilising agent.

[0052] In at least one embodiment, the hop oil is for use in a beverage, preferably a beer, a low-alcohol beer, an alcohol-free beer, a hop water, a hop soda, a hop tea, a seltzer, a spirit, or a kombucha.

[0053] In at least one embodiment, the hop oil is for use in healthcare products or cosmetics.

[0054] In a sixth aspect, the invention provides a hop oil composition comprising:a. about 5 to 50% v / v of a hop oil extract, andb. about 50 to 95% v / v of a solubilising agent.

[0055] In at least one embodiment, the solubilising agent is:i. a glycerol , and / orii. a propylene glycol.

[0056] In at least one embodiment, the combination of oil with a solubilising agent increases miscibility of the hop oil with aqueous solutions.

[0057] In at least one embodiment, the hop oil extract is a hop oil extract according to the second or third aspect.

[0058] In at least one embodiment, the composition comprises about 10 to 50%, about 15 to 50%, about 20 to 50%, about 25 to 50%, about 30 to 50%, about 35 to 50%, about 40 to 50% or about 45 to 50% v / v of the hop oil extract. In at least one embodiment, the composition comprises about 5 to 45%, about 5 to 40%, about 5 to 35%, about 5 to 30%, about 5 to 25%, about 5 to 20%, about 5 to 15% or about 5 to 10% v / v hop oil extract. In at least one embodiment, the composition comprises about 10 to 45% v / v hop oil extract. In at least one embodiment, the composition comprises about 15 to 40% v / v hop oil extract. In at least one embodiment, the composition comprises about 20 to 35% v / v hop oil extract. In a preferred embodiment, the composition comprises about 20 to 25% v / v hop oil extract, more preferably about 20% v / v hop oil extract. In at least one embodiment, the composition comprises at least about 5% v / v hop oil extract. In at least one embodiment, the composition comprises at least about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, or about 19% v / v hop oil extract.

[0059] In at least one embodiment, the solubilising agent comprises one or more polyols. In at least one embodiment, the solubilising agent comprises one or more food grade emulsifiers. In at least one embodiment, the solubilising agent is a glycerol, a glycol, a polysorbate, a sorbitan ester, or a combination of two or more thereof. In at least one embodiment, the solubilising agent is glycerol, glycerol monostearate, polyglycerol polyricinoleate, polypropylene glycol, polysorbate 80, polysorbate 60, sorbitan monostearate, or a combination of two or more thereof. In at least one embodiment, the solubilising agent is a combination of glycerol and polypropylene glycol.

[0060] In at least one embodiment, the composition comprises about 55 to 95%, about 60 to 95%, about 65 to 95%, about 70 to 95%, about 75 to 95%, about 80 to 95%, about 85 to 95% or about 90 to 95% v / v solubilising agent. In at least one embodiment, the composition comprises about 50 to 90%, about 50 to 85%, about 50 to 80%, about 50 to 75%, about 50 to 70%, about 50 to 65%, about 50 to 60% or about 50 to 55% v / v solubilising agent. In at least one embodiment, the composition comprises about 55 to 90% v / v solubilising agent. In at least one embodiment, the composition comprises about 60 to 85% v / v solubilising agent. In at least one embodiment, the composition comprises about 65 to 80% v / v solubilising agent. In a preferred embodiment, the composition comprises about 75 to 80% v / v solubilising agent, more preferably about 80% v / v solubilising agent. In at least one embodiment, the composition comprises at least about 95% v / v solubilising agent. In at least one embodiment, the composition comprises at least about95%, about 94%, about 93%, about 92%, about 91%, about 90%, about 89%, about 88%, about 87%, about 86%, about 85%, about 84%, about 83%, about 82%, or about 81% v / v solubilising agent.

[0061] In at least one embodiment, the composition comprises about 55 to 90% v / v propylene glycol. In at least one embodiment, the composition comprises about 60 to 85% v / v propylene glycol. In at least one embodiment, the composition comprises about 65 to 80% v / v propylene glycol.

[0062] In at least one embodiment, the composition comprises about 0.1 to 5% v / v glycerol. In at least one embodiment, the composition comprises about 0.5 to 2.5% v / v glycerol.

[0063] In at least one embodiment, the composition comprises about 10 to 20% v / v hop oil, about 75 to 90% v / v propylene glycol and about 0.1 to 5% v / v glycerol. In at least one embodiment, the composition comprises about 15 to 20% v / v hop oil, about 75 to 85% v / v propylene glycol and about 0.5 to 2.5% v / v glycerol.

[0064] In at least one embodiment, the composition comprises about 20% v / v hop oil, about 79% propylene glycol and about 1% glycerol.

[0065] In a seventh aspect, a beverage comprising the hop oil extract of any one of the second or third or fourth aspects or the hop oil composition of the fifth or sixth aspect.

[0066] In at least one embodiment, the beverage is an alcoholic beverage, a low alcohol beverage, a non-alcohol beverage, a fermented beverage, a hop tea or a hop water. In at least one embodiment, the beverage is an alcoholic, a low alcohol or a non-alcoholic beer.

[0067] In at least one embodiment, the beverage is a beer comprising about 0.0001% to 0.01% of the hop oil extract.

[0068] In an eighth aspect, a process of preparing a beverage comprising the addition of the hop oil extract of any one of the second or third or fourth aspects, or the hop oil composition of the fifth or sixth aspect.

[0069] In at least one embodiment, the process involves a fermentation step.

[0070] In at least one embodiment, the hop oil extract of the second aspect or third aspect or fourth aspect, or the hop oil composition of the fifth or sixth aspect is added during the fermentation step.

[0071] In at least one embodiment, the hop oil extract of the second aspect or third aspect or fourth aspect, or the hop oil composition of the fifth or sixth aspect is added after the fermentation step.

[0072] Any of the aforementioned features or embodiments or aspects may be combined with one or more of the other features or embodiments or aspects as described herein.

[0073] This invention may also be said broadly to consist in the parts, elements and features referred to or indicated in the specification of the application, individually or collectively, and any or all combinations of any two or more said parts, elements or features, and where specific integers are mentioned herein which have known equivalents in the art to which this invention relates, such known equivalents are deemed to be incorporated herein as if individually set forth.

[0074] As used herein “wet hop cones” are hop bines are harvested in the field and taken to the on-farm harvesting facilities. There hop cones, leaf and stem are mechanically removed from the bines. The leaf and stem are then removed by mechanical sorting to render just hop cones (although there will still most likely be some leaf and stem present with the hop cones). The hop cones are then collected and bagged from an engineered collection and bagging point. The hops are then transported to the oil / solution processing facility and placed in cool store pending processing into oil / solution.

[0075] As used herein “dry hop cones” are hop bines are harvested in the field and taken to the on-farm harvesting facilities. There hop cones, leaf and stem are mechanically removed from the bines. The leaf and stem are then removed by mechanical sorting to render just hop cones (although there will still most likely be some leaf and stem present with the hop cones). The hop cones are then dried in the on-farm kilns to between 89-91% dry matter. The dried hop cones are then conditioned for a period on a concrete floor. They are then pressed and packaged into bales (not unlike wool bales). The baled hop cones are then transported to the oil / solution processing facility and placed in cool store pending processing into oil / solution.

[0076] As used herein “hop bines” are bines are harvested in the field and taken to the on-farm harvesting facilities. There hop cones, leaf and stem are mechanically removed from thebines. The leaf and stem are then removed by mechanical sorting to render just hop cones (although there will still most likely be some leaf and stem present with the hop cones). The hop cones are then dried in the on-farm kilns to between 89-91% dry matter. The dried hop cones are then conditioned for a period on a concrete floor. They are then pressed and packaged into bales. The baled hop cones are then transported to the processing facility where they are ground into a power and then pressed into pellets. They may then be packaged into oxygen purged bags and placed in cool store pending processing into oil / solution.

[0077] As used herein “harvest periods” are the optimum time period to gather crops, for example hop cones. It will be appreciated by a person skilled in the art that the optimum time to gather crops will vary on the crop itself and the geographical location that the crop is cultivated.

[0078] As used herein “early” when referring to harvest periods is the time period within the first third of the harvest period of the crop being harvested.

[0079] As used herein “middle” when referring to harvest periods is the time period within the second third of the harvest period of the crop being harvested.

[0080] As used herein “late” when referring to harvest periods is the time period within the last third of the harvest period of the crop being harvested.

[0081] As used herein “(s)” following a noun means the plural and / or singular forms of the noun.

[0082] As used herein the term “and / or” means “and” or “or” or both.

[0083] The term “comprising” as used in this specification means “consisting at least in part of’. When interpreting each statement in this specification that includes the term “comprising”, features other than that or those prefaced by the term may also be present. Related terms such as “comprise” and “comprises” are to be interpreted in the same manner.

[0084] It is intended that reference to a range of numbers disclosed herein (for example, 1 to 10) also incorporates reference to all rational numbers within that range (for example, 1, 1.1, 2, 3, 3.9, 4, 5, 6, 6.5, 7, 8, 9 and 10) and also any range of rational numbers within that range (for example, 2 to 8, 1.5 to 5.5 and 3.1 to 4.7) and, therefore, all sub-ranges of all ranges expressly disclosed herein are hereby expressly disclosed. These are only examples of what is specifically intended and all possible combinations of numerical values between the lowest value and thehighest value enumerated are to be considered to be expressly stated in this application in a similar manner.

[0085] Although the present invention is broadly as defined above, those persons skilled in the art will appreciate that the invention is not limited thereto and that the invention also includes embodiments of which the following description gives examples.BRIEF DESCRIPTION OF THE DRAWINGS

[0086] The invention will now be described with reference to the Figures in which:

[0087] Figure 1 shows a vacuum distillation system useful in the present invention.DETAILED DESCRIPTION OF THE INVENTION

[0088] Various embodiments of the present technology described herein relates to methods for extraction, separation, recovery and / or purification of various hop materials. The methods aim to provide efficient and cost-effective methods for separation of various components from hops, hop extracts, hop biomass and / or hop by-products. Moreover, the method can be used to extract hops from both dry and wet hop cones.Process of making a hop oil

[0089] In one aspect, a vacuum distillation process for extracting liquid products from hops is provided. The process comprises (a) charging a distillation vessel with hops and water; (b) heating the water at a temperature and reduced pressure sufficient to produce a water vapour, (c) contacting the water vapour with the hops to produce a hop extract vapour; and (d) condensing the hop extract vapour in a condenser to obtain a liquid hop extract comprising a hop oil and a hydrosol.

[0090] Any suitable variety of hop may be used in the invention. For example, the invention may be carried out with any hop variety containing hop oils that are useful, e.g., in the preparation of a beverage such as a beer. Suitable hop varieties include, but are not limited to, Admiral, Agnus, Antanum, Amarillo, Apollo, Bohemie, Bor, Bramling Cross, Brewer’s Gold, Bullion, Cascade, Centennial, Challenger, Chinook, Citra, Cluster, Columbus, Crystal, Eroica, First Gold, Feux-Coeur Francais, Fuggle, Galaxy, Galena, Glacier, Goldings, Green Bullet, Greenburg, Hallertau, Harmonie, Herald, Herkules, Hersbrucker, Horizon, Kazbek, Liberty, Lublin, Magnum, Merkur, Millennium, Motueka, Mosaic, Mount Hood, Mount Rainier, NelsonSauvin, Newport, Northdown, Northern Brewer, Nugget, Opal, Pacifica, Pacific Gem, Pacific Jade, Palisade, Perle, Phoenix, Pligrim, Pilot, Pioneer, Polnischer Lublin, Premiant, Pride of Ringwood, Progress, Rakau, Riwaka, Rubin, Saaz, Saaz Late, San Juan Ruby Red, Santiam, Saphir, Satus, Select, Simcoe, Sladek, Smaragd, Sorachi Ace, Southern Cross, Spalt, Sterling, Strisselspalt, Styrian Aurora, Styrian Bobek, Styrian Goldings, Styrian Celeia, Summit, Tardif de Bourgogne, Target, Taurus, Tettnang, Tomahawk, Tomyski, Tradition, Ultra, Vanguard, Vital, Waimea, Warrior, Whitbread Golding Variety (WGV), Willamette, Zeus, or a combination of two or more varieties.

[0091] Various forms of hops may be extracted with the process of the invention. For example, the hops may be provided in the form of wet hop cones, dry hop cones, hop pellets or a mixture of two or more thereof. In at least one embodiment, the hops are wet hop cones. Wet hops (also called fresh hops) are hops that have not been dried. Preferably, wet hops are extracted soon after harvesting (e.g. within 24 hours) because wet hops spoil quickly. Advantageously, extraction of wet hops provides a hop oil extract with a sensory profile similar to wet hops and, therefore, is a long shelf-life alternative to wet hops.

[0092] In at least one embodiment, the hops are dry hop cones. In at least one embodiment, the dry hop cones comprise about 80 to 95% w / w dry matter. In at least one embodiment, the dry hop cones comprise about 85 to 92% w / w dry matter; preferably, about 89 to 91% w / w dry matter. In at least one embodiment, the hop pellets comprise about 80 to 95% w / w dry matter. In at least one embodiment, the hop pellets comprise about 85 to 92% w / w dry matter; preferably, about 89 to 91% w / w dry matter. In at least one embodiment, the wet hop cones comprise about 10 to 40% w / w dry matter. In at least one embodiment, the wet hop cones comprise about 20 to 30% w / w dry matter; preferably, about 20 to 25% w / w dry matter.

[0093] The process comprises charging a distillation vessel with water and hops. The distillation vessel is suitable for heating the water under reduced pressure to produce a water vapour. Accordingly, the vessel is preferably a closed system. For example, the distillation vessel may comprise a distillation pot or chamber. The processes may use a heat source (e.g. burners applied to the vessel) and a means for reducing the pressure within the vessel (e.g. a vacuum pump) to control the temperature and pressure within the distillation vessel. Those persons skilled in the art will appreciate other means for heating water under reduced pressure may be suitable for use in the invention.

[0094] The distillation vessel is configured to allow the water vapour to contact the hops and thereby produce a hop extract vapour. For example, the distillation vessel may comprise a single chamber. In these embodiments, the water and hops are mixed within the single chamber of the distillation vessel. The mixture is heated under reduced pressure to product the hop extract vapour.

[0095] Alternatively, the distillation vessel may have two or more chambers. The two chambers may be divided by a separator, e.g., a porous separator. The inventors have found that it is advantageous to have a separate chamber for water and the hop material. In this case the distillation vessel has water in a lower chamber and hop material in an upper chamber. The two chambers may be separated by porous material, such as a metallic mesh. The hops sit on top of the mesh and the water is heated under reduced pressure until water vapour is generated. The water vapour moves through the mesh to contact the hops. Preferably, the water vapour passes through a layer of the hops situated on the porous separator.

[0096] The distillation vessel can alternatively comprise two or more separate chambers in fluid communication. For example, the water can be in a first chamber and the hops can be in a second chamber. The water vapour generated by heating the water in the first chamber under pressure may be conveyed, e.g., through a pipe or tubing, to the second chamber, where it can contact the hops. Accordingly, the first chamber may be any container suitable for heating the water under reduced pressure. The second chamber may be any suitable container for contacting the water vapour produced in the first chamber with the hops. For example, the second chamber may be a column or cartridge containing the hops, such as where the water vapour enters one end of the second chamber, passes through the hops to produce a hop extract vapour that exits a distal end of the second chamber.

[0097] The distillation vessel may be a single vessel comprising one or more chambers, or two or more vessels (comprising one or more chambers) in series or parallel.

[0098] The inventors have found that the process is suitable for the extraction of hop oils from hops, preferably, wet hop cones, dried hop cones, hop pellets, or a combination of two or more thereof.

[0099] Preferably the liquid that is heated during the extraction is water.

[0100] When the apparatus is charged with wet hop cones, the inventors have found that it is preferable, albeit optional, to compress the wet hop cones to reduce the volume of the wet hop cones in the apparatus. The wet hops can be compressed to at least 50% of their original volume. Most preferably, the wet hop cones are compressed to 70% of their original volume.

[0101] The inventors have found that this compression was advantageous as it resulted in greater efficiency of contact of water vapour with the hops. Without compression, it is possible for a larger volume of water vapour to pass through the empty gaps between the hops without making sufficient contact with said material to extract the essential oils.

[0102] The inventors have also found that this compression is advantageous when dried hop cones are used, especially when the hops are newly dried and have not been compressed into bales. It is appreciated that the benefit of this compression is for extraction efficiency as detailed above.

[0103] When baled dried hop cones or hop pellets are used in the process, the inventors have found that it is advantageous to disrupt the dried hop cones or hop pellets into smaller pieces. Preferably, the hops are disrupted manually using rakes or paddles, so the individual cones are free. However, it is appreciated that any other method for breaking up a dried plant material known in the art can be employed. It is appreciated that the benefit of this disruption is for extraction efficiency as detailed above. It will also be appreciated that the hop pellets do not necessarily require disruption as they can be small enough to extract directly. The hop pellets could also be ground into a powder prior to extraction.

[0104] Through extensive trail, the inventors have also found that if the chamber housing the hop material is filled to more than 70% of the available volume, the efficiency of the extraction is negatively affected. Overfilling the chamber results in overheating the lower portion of the hop material. This overheating has the effect of the resulting oil from the extraction being produced slower and having a darker hue. The flavour profile and aroma of the resulting darker oils were also found to have more unpleasant aroma notes including, but not limited to vegetable-aroma, tomato leaf, rubber, toast, and hay. The flavour profile and aroma of the resulting darker oils were also found to have less of the favourable aroma notes, including but not limited to fresh fruit, grassy aromas, citrus, diesel, and attractive sulphur compounds. Overall, the darker hue oils were less aromatically vibrant and fresh smelling than their lighter counterparts.

[0105] Once a desired volume of water has been added to the apparatus, the efficiency of the process is maintained if the volume of water is kept at that level. This can be achieved by recycling the water through a condensation process or adding more water into the system either manually or automatically.

[0106] The inventors have found that it is advantageous to heat the water at a high temperature. Heating at high temperatures allows for the efficient extraction of compounds which contribute to the taste and aroma profile associated with the hops being extracted. The inventors have found that heating at higher temperatures surprisingly does not result in the extraction of unpleasant sulfur-containing compounds, or the chemical degradation of compounds which contribute to the taste and aroma profile associated with the hops.

[0107] The extraction of hops can be achieved when the water is heated at temperatures between about 71 to 89°C. For example, in step (b) the water may be heated to a temperature of about 75 to 89°C, 80 to 89°C or 85 to 89°C. The extraction temperature is most preferably between 85 to 989°C. When lower temperatures are used, a greater pressure reduction must be applied to the system to boil the liquid. Surprisingly, producing water vapour at a temperature at 55°C or above and below 100°C results in a hop oil extract with desirable sensory profile.

[0108] The inventors have found that it is advantageous to extract liquid hop extracts at a temperature of about 71 to 89°C. more preferably about 85 to 89°C. At these temperatures, the flowability of the extract passing through the system is most efficient for extraction. Greater efficiency allows the liquid hop extract to be extracted without exposing the hop plant matter to adverse conditions that might result in the loss of desirable aromatic compounds. Moreover, using higher temperatures can lead to undesirable liquid hop extracts, such as darker oil with unwanted odours. Whereas, using temperatures lower than this can lead to poor flow rate and poor extraction of the desirable aromatic compounds from the hops, for example resulting in oils with lower myrcene concentration.

[0109] The reduced pressure to boil the extraction liquid is between 0.01 to 1.00 bar below atmospheric pressure. In at least one embodiment, the reduced pressure used in step (b) is between 0.05 to 0.80 bar below atmospheric pressure. In at least one embodiment, the reduced pressure used in step (b) is between 0.10 to 0.70 bar below atmospheric pressure. In at least one embodiment, the reduced pressure used in step (b) is between 0.15 to 0.6 bar below atmospheric pressure.

[0110] The extraction vapour can be condensed by contacting the extraction vapour with any cooling apparatus known to a person skilled in the art. Most preferably the extraction vapour is conveyed from the distillation vessel to an interconnected cooling chamber, whereby the extraction vapour is condensed.

[0111] The condensed extraction vapour is collected in a collection chamber. The collection chamber can be optionally interconnected to the cooling chamber by a sight-glass or directly.

[0112] The collection chamber can optionally include an oil reservoir glass, collection pipe and collection port. The inventors have found it advantageous to configure the collection pipe such that the condensed extraction vapour is able to be separated into hop oil and hydrosol by overflow density separation. The hop oil typically has a relatively lower density than the hydrosol layer, so can be extracted as the upper layer of the overflow liquid.

[0113] The hydrosol layer can be optionally removed by opening a hydrosol valve and emptying the hydrosol into a container.

[0114] Once the flow of hop oil being collected in the collection chamber slows, further hop oil extract may be obtained by doing a flash flow step. Flash flow is the rapid evaporation of the liquid phase in the distillation vessel caused by a sharp change in pressure and / or temperature. The flash flow step can comprise of either:a. Opening the vacuum release valve, allowing the reduced pressure in the system to decrease from about 0.3 to 0.5 bar below atmospheric pressure towards about 0.2 bar below atmospheric pressure. While the vacuum in the system is being reduced, the temperature of the extraction liquid can be increased by at least about 5 °C. The flow with initially stop, at which point the reduced pressure is increased back to about 0.3 to 0.5 bar below atmospheric pressure to begin the flash flow; orb. Slowly, in small increments, reduce further the pressure of the apparatus from about 0.3 to 0.5 bar below atmospheric pressure towards about 0.5 to 0.7 bar below atmospheric pressure, keeping the heating temperature of the extraction liquid constant.Hop oils

[0115] The hop oil obtained from the above-described process could be used directly, for example for preparing a beverage, cosmetic product or therapeutic product.

[0116] The hop oil extracted may contain some particulate matter that would be undesirable for entry into end-user products. Therefore, it is advantageous to remove said particulate matter.

[0117] The particulate matter can be removed by any chemical or mechanical techniques known to a person skilled in the art. For example, exposing the hop oils to freezing conditions (i.e. less than 0°C) for about 10 hours and running the frozen oil through a filter will remove the undesirable particulate matter. This process can be repeated as many times as required.

[0118] The filtered oil can be used directly. The filtered oil may contain some volatile components, some of which can be optionally removed. The removal of some of the volatile components result in a more stable odour and / or flavour profile.

[0119] The volatile components can be removed by any chemical or mechanical techniques known to a person skilled in the art. For example, storing the filtered hop oils in a loosely sealed container at a temperature between 0 and 4°C for about 24 hours allows for enough volatiles to dissipate.

[0120] The hop oils can be decanted into a container for storage. The oil will have an increased shelf-life if the bottle in flushed with an inert gas before sealing. The inert gas can be any inert gas suitable for food-storage, such as nitrogen or carbon dioxide.

[0121] The hop oils remain stable when stored at room temperature for about 12 months. The hop oils remain stable when refrigerated for about 24 months.Hop oil characteristics

[0122] The hop oils produced by the above process are unique both in their chemical composition and in their physical properties.

[0123] In an aspect, the invention provides a hop oil extract comprising at least about 75% myrcene.

[0124] The hop oils may additionally comprise of one or more other hop essential oils, for example: camphene, P-pinene, limonene, terpinene, p-cymene, methyl-4-methylex-2-enoate, a-capaene, linalool, 2-undecanone, methyl decanoate, caryophyllene, methyl dec-4-enoate, farnesene, humulene, muurolene, a-selinene, P -selinene, geranyl acetate, 8-cadinene, y-cadinene, geranyl isobutyrate, 2-tridecanone, geraniol, limonene- lO-ol, caryophyllene oxide, humulene epoxides, caryolan-l-ol, humulol, humulene di epoxide A.

[0125] In at least one embodiment, the hop oil extract comprises at least about 80% hop essential oils. In at least one embodiment, the hop oil extract comprises at least about 85%, about 90%, about 95%, about 98% or about 99% hop essential oils. In at least one embodiment, the hop essential oil extract comprises about 100% hop oils.

[0126] In at least one embodiment, the hop oil extract further comprises caryophyllene, farnesene, geraniol, linalool, and / or humulene, or a combination of two or more thereof. In at least one embodiment, the hop oil extract comprises caryophyllene, famesene, and humulene. In at least one embodiment, the hop oil extract comprises caryophyllene, famesene, geraniol, linalool and humulene.

[0127] In at least one embodiment, the hop oil extract comprises at least 76%, about 77%, about 78%, about 79%, about 80%, about 81%, about 82%, about 83%, about 84%, about 85%, about 86%, about 87%, about 88%, about 89%, about 90%, about 91%, or about 92% myrcene. In at least one embodiment, the hop oil extract comprises at least about 80% myrcene. In at least one embodiment, the hop oil extract comprises about 75 to 92% myrcene. In at least one embodiment, the hop oil extract comprises about about 80 to 92% or about 85 to 92% myrcene. In at least one embodiment, the hop oil extract comprises about 80 to 92% myrcene.

[0128] The inventors have found the concentrations of myrcene extracted from hops using the aforementioned vacuum steam distillation process are surprisingly higher than can be obtained from the same hops using other extraction techniques. Hop oils with higher concentrations of myrcene are advantageous as they impart various desirable flavour profiles to the foodstuff that they are added to, such as: hoppiness, earthy, musky, spicy, fruity, or sweet flavour profiles. Specifically, myrcene can impart flavours likened to mangoes, thyme, bay leaves, lemongrass and / or basil. Such flavours are particularly desirable in the manufacture of beverages, such as beers. The hop oils can be added at any stage in the manufacture of beverages, including in the manufacture of non-alcoholic beverages.

[0129] In at least one embodiment, the hop oil extract comprises about 0.1 to 10% caryophyllene. In at least one embodiment, the hop oil extract comprises about 0.1 to 5%, about 0.1 to 2%, or about 0.1 to 1% caryophyllene. In at least one embodiment, the hop oil extract comprises about 1 to 10% or about 1 to 5% caryophyllene. In at least one embodiment, the hop oil extract comprises less than about 10% caryophyllene. In at least one embodiment, the hop oil extract comprises less than about 5% caryophyllene.

[0130] In at least one embodiment, the hop oil extract comprises about 0.01 to 10% farnesene. In at least one embodiment, the hop oil extract comprises about 0.01 to 5%, about 0.01 to 4%, or about 0.01 to 2% famesene. In at least one embodiment, the hop oil extract comprises about 0.1 to 5%, about 0.1 to 4%, or about 0.1 to 2% famesene. In at least one embodiment, the hop oil extract comprises less than about 5% farnesene. In at least one embodiment, the hop oil extract comprises less than about 2% or 1% farnesene.

[0131] In at least one embodiment, the hop oil extract comprises about 0.1 to 15% humulene. In at least one embodiment, the hop oil extract comprises about 0.1 to 10%, 0.1 to 5%, 0.1 to 2% or 0 / 1 to 1% humulene. In at least one embodiment, the hop oil extract comprises about 1 to 15%, 1 to 10% humulene. In at least one embodiment, the hop oil extract comprises less than about 10% humulene. In at least one embodiment, the hop oil extract comprises less than about 5% humulene. In at least one embodiment, the hop oil extract comprises less than about 2% or 1% humulene.

[0132] In at least one embodiment, the hop oil extract comprises at least about 60% myrcene, about 0.1 to 10% caryophyllene, about 0.1 to 10% farnesene, and about 0.1 to 15% humulene. In at least one embodiment, the hop oil extract comprises at least about 80% myrcene, about 0.1 to 5% caryophyllene, about 0.1 to 5% farnesene, and about 0.1 to 5% humulene. In at least one embodiment, the hop oil extract comprises at least about 80% myrcene, less than about 5% caryophyllene, less than about 5% farnesene, and less than about 5% humulene.

[0133] The concentration of chemical components, such as myrcene, may be determined by convention techniques known in the art. For example, in some embodiments, the percentage chemical components, such as myrcene, is determined as the total analysed area under the curve of a gas chromograph.

[0134] In one aspect, the invention provides a hop oil extract comprising a low concentration of alpha acids, iso-alpha acids and / or beta acids.

[0135] In at least one embodiment, the hop oil extract comprises less than 1% by weight alpha acids. In at least one embodiment, the hop oil extract comprises less than 0.1% by weight alpha acids. The alpha acids known to usually be present in hop extracts include, but are not limited to humulone, adhumulone, cohumulone, and prehumulone. In at least one embodiment, the hop oil extract is essentially free of alpha-acids.

[0136] In at least one embodiment, the hop oil extract comprises less than 1% by weight isoalpha acids. In at least one embodiment, the hop oil extract comprises less than 0.1% by weight iso-alpha acids. The iso-alpha acids known to usually be present in hop extracts include, but are not limited to cv.s-isohumulone and / ra / z.s-humulone. In at least one embodiment, the hop oil extract is essentially free of iso-alpha acids.

[0137] In at least one embodiment, the hop oil extract comprises less than 1% by weight beta acids. In at least one embodiment, the hop oil extract comprises less than 0.1% by weight beta acids. The beta acids known to usually be present in hop extracts include, but are not limited to lupulone, colupulone, adlupulone, prelupulone, and postlupulone. In at least one embodiment, the hop oil extract is essentially free of beta acids.

[0138] The analysis of alpha, iso-alpha and / or beta acids in the hop oil extracts can be determined by any analytical method known to a person of ordinary skill in the art. For example, methods described by the American Society of Brewing Chemists

[0139] In at least one embodiment, the hop oil extract is obtained from wet hop cones, dry hop cones, hop pellets or a mixture of two or more thereof. In at least one embodiment, the hop oil extract is obtained from wet hop cones. In at least one embodiment, the hop oil extract is obtained from dry hop cones.

[0140] In at least one embodiment, the hop oil extract is obtained from a hop variety selected Admiral, Agnus, Antanum, Amarillo, Apollo, Bohemie, Bor, Bramling Cross, Brewer’s Gold, Bullion, Cascade, Centennial, Challenger, Chinook, Citra, Cluster, Columbus, Crystal, Eroica, First Gold, Feux-Coeur Francais, Fuggle, Galaxy, Galena, Glacier, Goldings, Green Bullet, Greenburg, Hallertau, Harmonie, Herald, Herkules, Hersbrucker, Horizon, Kazbek, Liberty, Lublin, Magnum, Merkur, Millennium, Motueka, Mosaic, Mount Hood, Mount Rainier, Nelson Sauvin, Newport, Northdown, Northern Brewer, Nugget, Opal, Pacifica, Pacific Gem, Pacific Jade, Palisade, Perle, Phoenix, Pligrim, Pilot, Pioneer, Polnischer Lublin, Premiant, Pride of Ringwood, Progress, Rakau, Riwaka, Rubin, Saaz, Saaz Late, San Juan Ruby Red, Santiam, Saphir, Satus, Select, Simcoe, Sladek, Smaragd, Sorachi Ace, Southern Cross, Spalt, Sterling, Strisselspalt, Styrian Aurora, Styrian Bobek, Styrian Goldings, Styrian Celeia, Summit, Tardif de Bourgogne, Target, Taurus, Tettnang, Tomahawk, Tomyski, Tradition, Ultra, Vanguard, Vital,Waimea, Warrior, Whitbread Golding Variety (WGV), Willamette, Zeus, or a combination of two or more varieties.

[0141] In at least one embodiment, the hop oil extract is obtained from wet hop cones, wherein hop oil extract is extracted from the wet hop cones within 24 hours of being harvested.

[0142] In at least one embodiment, the hop oil is for use in a beverage, preferably beer, low-alcohol beer, alcohol-free beer, hop water, seltzer, spirits, kombucha.Solubilised oils

[0143] Another aspect of the invention involves preparing a solubilised hop oil composition by mixing the hop oil extract with a solubilising agent.

[0144] Such hop oil compositions are advantageous as they improve the solubility of hop oils when combined with another aqueous solution.

[0145] The inventors have found that the hop oils have the surprising characteristic of being stable at a higher concentration of hop oil extract than currently known in the art.

[0146] In at least one embodiment, about 5 to 50% v / v of a hop oil extract can be combined with about 50 to 95% v / v of solubilising agent.

[0147] In at least one embodiment, the composition comprises about 10 to 45% v / v hop oil extract. In at least one embodiment, the composition comprises about 15 to 40% v / v hop oil extract. In at least one embodiment, the composition comprises about 20 to 35% v / v hop oil extract. In a preferred embodiment, the composition comprises about 20 to 25% v / v hop oil extract, more preferably about 20% v / v hop oil extract. In at least one embodiment, the composition comprises at least about 5% v / v hop oil extract. In at least one embodiment, the composition comprises at least about 5%, 6%, 7%, 8%, 9%, 10%, 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, or 19% v / v hop oil extract.

[0148] In at least one embodiment, the composition comprises about 55 to 90% v / v solubilising agent. In at least one embodiment, the composition comprises about 60 to 85% v / v solubilising agent. In at least one embodiment, the composition comprises about 65 to 80% v / v solubilising agent. In a preferred embodiment, the composition comprises about 75 to 80% v / v solubilising agent, more preferably about 80% v / v solubilising agent. In at least one embodiment, the composition comprises at least about 95% v / v solubilising agent. In at least oneembodiment, the composition comprises at least about 95%, 94%, 93%, 92%, 91%, 90%, 89%, 88%, 87%, 86%, 85%, 84%, 83%, 82%, or 81% v / v solubilising agent.

[0149] The solubilising agent used could be any one or more known solubilising agents known to a person skilled in the art.

[0150] In at least one embodiment, the solubilising agent comprises one or more polyols. In at least one embodiment, the solubilising agent comprises one or more food grade emulsifiers. In at least one embodiment, the solubilising agent is a glycerol, a glycol, a polysorbate, a sorbitan ester, or a combination of two or more thereof. In at least one embodiment, the solubilising agent is glycerol, glycerol monostearate, polyglycerol polyricinoleate, polypropylene glycol, polysorbate 80, polysorbate 60, sorbitan monostearate, or a combination of two or more thereof. In at least one embodiment, the solubilising agent is a combination of glycerol and polypropylene glycol.

[0151] The inventors have found that a combination of propylene glycol and glycerol are suitable solubilising agents for the dissolution of up to about 20% hop oil.

[0152] In at least one embodiment, the composition comprises about 55 to 90% v / v propylene glycol. In at least one embodiment, the composition comprises about 60 to 85% v / v propylene glycol. In at least one embodiment, the composition comprises about 65 to 80% v / v propylene glycol.

[0153] In at least one embodiment, the composition comprises about 0.1 to 5% v / v glycerol. In at least one embodiment, the composition comprises about 0.5 to 2.5% v / v glycerol.

[0154] In at least one embodiment, the composition comprises about 10 to 20% v / v hop oil, about 75 to 90% v / v propylene glycol and about 0.1 to 5% v / v glycerol. In at least one embodiment, the composition comprises about 15 to 20% v / v hop oil, about 75 to 85% v / v propylene glycol and about 0.5 to 2.5% v / v glycerol.

[0155] In at least one embodiment, the composition comprises about 20% v / v hop oil, about 79% propylene glycol and about 1% glycerol.

[0156] The hop oil compositions can be decanted into a container for storage. The hop oil compositions will have an increased shelf-life if the bottle in flushed with an inert gas beforesealing. The inert gas can be any inert gas suitable for food-storage, such as nitrogen or carbon dioxide.Hop oil uses

[0157] The hop oil extract and hop oil composition of the present invention are useful in various applications.

[0158] The hop oil extract may be used to prepare a beverage having a hop characteristic. Unless stated otherwise, the hop oil extract may be used as the pure extract or any other suitable form, e.g. in the hop oil composition. Suitable beverages include, but are not limited to, an alcoholic beverage, a low alcohol beverage, a non-alcohol beverage, a fermented beverage or a hop water. In at least one embodiment, the beverage is an alcoholic, a low alcohol or a nonalcoholic beer.

[0159] In at least one embodiment, the beverage is a beer comprising about 0.0001 to 0.01% of the hop oil extract. In at least one embodiment, the beverage is a beer comprising about 0.0005 to 0.01%, 0.001 to 0.01% or 0.005 to 0.01% of the hop oil extract.

[0160] Accordingly, the present invention also provides a process of preparing a beverage comprising the addition of the hop oil extract or the hop oil composition. The process may involve adding the hop oil extract during the preparation of the beverage (e.g. during fermentation) or adding the hop oil extract as a flavouring component to the beverage.

[0161] The beverage may be a fermented beverage. In these embodiments, the hop oil extract may be added, before, during and / or after the fermentation step.

[0162] The hop oils can be combined with other liquid products to introduce a hoppiness to the liquid product.

[0163] A non-exhaustive list of liquid products that the hop oils can be added include: alcoholic beer, low-alcohol beer, non-alcoholic beer, alcoholic pale ales, low-alcohol pale ales, non-alcoholic pale ales, alcoholic stout, low-alcohol stout, non-alcoholic stout, alcoholic pilsner, low-alcohol pilsner, non-alcoholic pilsner, alcoholic lager, low-alcohol lager, non-alcoholic lager, alcoholic dark ales, low-alcohol dark ales, non-alcoholic dark ales, alcoholic bitter, low-alcohol bitter, non-alcoholic bitter, alcoholic barley wine, low-alcohol barley wine, nonalcoholic barley wine, hop water, and hop teas.

[0164] It is well known that hops can be used for therapeutic purposes, for example see: Kyrou et al. Hormones 2017, 16(2): 171-180; Sun et al. Food and Energy Security 2022, 11(2): e367; Bolton et al. Chem. Res. Toxicol. 2019, 32(2): 222-233; http s : / / www . l antandfood . com / en-

[0165] Therefore, it will be appreciated that the hops oils can be used alone or in a therapeutic composition for use in prevention and / or treatment of depression, stress, anxiety, metabolic syndromes, cancers, weight gain, insulin resistance, menopausal symptoms, diabetes, osteoporosis and venous thrombosis.

[0166] Furthermore, the hop oils can be used alone or in a therapeutic composition for use as an antimicrobial agent, an inhibitor of proteolytic enzymes and a stimulator for fibrillar collagen.

[0167] The hop oils can also be used as in other aspects of the food industry as a preservative agent, functional food ingredient and health promoter.

[0168] The hop oils can be used in cosmetics, for example in hair care or skin care products.

[0169] The following non-limiting examples are provided to illustrate the present invention and in no way limit the scope thereof.EXAMPLES

[0170] Examples 1 and 2 relate to the extraction of hop oils from wet and dry hop cones. These extractions were achieved using the vacuum distillation apparatus as shown in Figure 1. It will be appreciated by a person skilled in the art that small modifications could be made to this apparatus without impacting the procedural methods given in Examples 1 or 2.

[0171] Figure 1 shows the distillation pot comprising the main pot (1) and the heating pot (2). The main pot (1) is connected to the condenser (3), which is cooled by passing cool water (4a, 4b) across the condenser. The condenser (3) optionally can have a sight glass (10) at the end of the condenser that is not adjoined to the main pot (1). The condenser (3) is connected to the separator column (5) wherein the liquid hop extract will collect and can be removed from the collection port (9) into a container. The separator column (5) is connected to a hydrosol storage tank (6), which itself is connected to the vacuum pumps (7). The separator column (5), hydrosol storage tank (6) and vacuum pumps (7) can be controlled from the manifold (11). Water from hydrosol storage tank (6) can be pressurized to move around the system by passage throughwater pump (12). In the set up shown, there is additionally a 3-way tap (8) controlling the flow of water between the heating pot (2), condenser (3) and hydrosol storage tank (6).Example 1: Process of extracting hop oil from wet hop cones

[0172] Fresh hops (90-110 kg) are added to the main pot and compressed until the hops are at approximately 70% of the original volume added to the pot. The heating pot is manually filled with 60-80 L of water, after which the water supplying is configured to keep the distillation pot at this level of water. A vacuum is applied (reducing the pressure between 0.3 to 0.45 bar below atmospheric pressure) and the heating pot is heated to 85-89°C. When the top temperature (read at the probe above the condenser pipe) has reached 45°C, the flow state will begin. Peak flow state is achieved at temperatures between 70-89°C. The vacuum is held for a total of 45 min, this time starting from once the flow state begins.

[0173] Once the flow state has started, the liquid will move from the condenser, through the sight glass, and accumulate in the collection port and oil reservoir glass. The first batch of oil is physically separated from the hydrosol by overflow density separation. The remaining oil is obtained either by flash evaporation of the system or achieved by reducing the pressure of the system to 0.6 bar below atmospheric pressure, followed by overflow density separation. The process is complete when the hop oil has been transferred to the collection port and the hydrosol is at the top of the collection port.

[0174] Typically, the output of oil extracted from the fresh hops is 0.5-1.2 L per 100 kg of hops.

[0175] During the extraction process, the pot temperature is observed to ensure the temperature does not exceed 96°C.

[0176] Table 1 shows analysis of the hop oils extracted by the process described in example 1 above. The example hop oils were obtained from NZ Cascade, Motueka, Riwaka, and Nelson Sauvin hops. Data has also been provided from Motueka and Riwaka hops harvested in the early, middle and late harvest.

[0177] The oils were analysed by gas chromatography using a Shimadzu GC2010 chromograph fitted with a PAL autosampler. The analysed area (%) and total peak area for each known chemical component of the hop oils are given below.Table 1Example 2: Process of extracting hop oil from dried hop cones

[0178] Dry hops (50 kg) are broken up into smaller parts and added to the main pot. The heating pot is manually filled with 60-80 L of water, after which the water supplying is configured to keep the heating pot at this level of water. A vacuum is applied (reducing the pressure between 0.3 to 0.45 bar below atmospheric pressure) and the heating pot is heated to 85-89°C. When the top temperature (read at the probe above the condenser pipe) has reached 45°C, the flow state will begin. Peak flow state is achieved at temperatures between 70-89°C. The vacuum is held for a total of 1-2 hours, this time starting from once the flow state begins.

[0179] Once the flow state has started, the liquid will move from the condenser, through the sight glass, and accumulate in the collection port and oil reservoir glass. The first batch of oil is physically separated from the hydrosol by overflow density separation. The remaining oil is obtained by flash evaporation of the system; achieved by reducing the pressure of the system to 0.6 bar below atmospheric pressure, followed by overflow density separation. The process is complete when the aqueous phase is almost at the top of the collection port.

[0180] Typically, the output of oil extracted from the fresh hops is 0.4-1.1 L per 50 kg of hops.

[0181] During the extraction process, the pot temperature is observed to make sure the temperature does not exceed 96°C.

[0182] Table 2 shows analysis of the hop oils extracted by the process described in example 2 above. The example hop oils were obtained from Motueka and Nelson Sauvin hops.

[0183] The oils were analysed by gas chromatography using a Shimadzu GC2010 chromograph fitted with a PAL autosampler. The analysed area (%) and total peak area for each known chemical component of the hop oils are given below.Table 2Example 3 - Purification of hop oils

[0184] The extracted oil from Example 1 or 2 is frozen using at around -20°C in a conventional freezer) for 10-16 hours. The frozen oil is covered in a container, but the container is not sealed allowing for volatile compound dispersion. The frozen oil is filtered to remove any debris, ice and other unwanted particulates. The process is repeated up to three times.

[0185] The filtered oil is stored in cool conditions, between 0-4°C, for 24 hours in a covered, unsealed container. The cooled oil is transferred to a container flushed with nitrogen, carbon dioxide, or another inert gas and sealed.

[0186] The hop oils obtained by this process had the following characteristics:<<<Example 4 - Solubilized hop oil

[0187] The oil from Example 3 can be mixed with emulsifiers to make a soluble hop oil product.

[0188] An example composition of a diluted hop oil product uses 20% hop oil, 79% propylene glycol and 1% glycerine.

[0189] The diluted hop oil product is stored in a sealed nitrogen-flushed container and can be kept at up to 25°C for up to (12 months), until required for brewing. The solubilised hop oils are creamy white and opaque. The solubilised oils have a similar viscosity and density to water and are easily dispersed in other liquid solutions, which is especially advantageous for adding the oils to beer.

[0190] It is not the intention to limit the scope of the invention to the abovementioned examples only. As would be appreciated by a skilled person in the art, many variations are possible without departing from the scope of the invention as set out in the accompanying claims.

Claims

CLAIMS1. A process for preparing a liquid hop extract, the process comprising:a. charging a distillation vessel with hops and water,b. heating the water to a temperature of about 71 to 89°C at a reduced pressure to produce a water vapour,c. contacting the water vapour with the hops to produce a hop extract vapour, andd. condensing the hop extract vapour in a condenser to obtain a liquid hop extract comprising a hop oil and a hydrosol.

2. The process of claim 1, wherein the hops are wet hop cones, dry hop cones, hop pellets or a mixture of any two or more thereof.

3. The process of claim 1 or 2, wherein the process further comprises:e. separating the hop oil and the hydrosol in the liquid hop extract obtained in step (d).

4. The process of any one of claims 1 or 3, wherein the process further comprises:f. collecting the hop oil obtained in step (e) in a collection chamber.

5. The process of any of claims 1 to 2, whereina. the wet hop cones comprise about 10 to 40% w / w dry matter;b. the dry hop cones comprise about 80 to 95% w / w dry matter;c. the hop pellets comprise about 80 to 95% w / w dry matter; ord. any combination of two or more of a to c.

6. The process of any of claims 1 to 5, wherein the hops are a hop variety selected from: from Green Bullet, Motueka, Nelson Sauvin, NZ Cascade, Pacific Sunrise, Pacifica, Rakau, Riwaka, Southern Cross and a mixture of two or more thereof.

7. The process of any of claims 1 to 6, wherein the water is kept at a constant volume by inputting water into the apparatus from an external source.

8. The process of any of claims 1 to 7, wherein the distillation vessel comprises a single chamber and the hops and the water in step (a) are mixed together.

9. The process of any of claims 1 to 7, wherein the distillation vessel comprises more than one chamber and the hops and the water in step (a) are in separate chambers of the distillation vessel.

10. The process of claim 9, wherein the distillation vessel comprises a lower chamber and an upper chamber, wherein the lower chamber is charged with the water and the upper chamber is charged with the hops and the water is heated in the lower chamber to produce the water vapour that flows from the lower chamber to the upper chamber and contacts the hops to produce the hop extract vapour.

11. The process of claim 10, wherein the lower chamber and the upper chamber are separated by a porous separator (e.g., a mesh or grate).

12. The process of claim 9, the distillation vessel comprises a first chamber in fluid connection with a second chamber, wherein the first chamber is charged with the water and the second chamber is charged with the hops, and the water is heated in the first chamber to produce water vapour that flows to the second chamber and contacts the hops to produce the hop extract vapour.

13. The process of any of claims 1 to 12, wherein the water is heated at a temperature sufficient to product water vapour at the reduced pressure.

14. The process of any of claims 1 to 13, wherein in step (b) the water is heated to a temperature of about 75 to 89°C, or about 80 to 89°C, or about 85 to 89°C.

15. The process of any of claims 1 to 14, wherein in step (b) the water is heated to a temperature of about 87°C.

16. The process of any of claims 1 to Error! Reference source not found., wherein before the process can proceed to step (d), a temperature measured at the top of the distillation vessel is about 45°C.

17. The process of any of claims 1 to 16, wherein during step (d), the temperature measure at the top of the apparatus is about 45 to 96°C, about or 55 to 95°C, or about 65 to 95°C, or about 70 to 89°C.

18. The process of any of claims 1 to 17, wherein the process uses wet hops harvested about 0 to 48 hours prior.

19. The process of any of claims 1 to 18, wherein the reduced pressure in step (b) is between 0.01 to 1.00 bar below atmospheric pressure.

20. The process of any of claims 1 to 19, wherein the hops are compressed in the distillation vessel before step (b).

21. The process of claim 20, wherein the hops are compressed until the hops are about 50 to 90%, or about 55 to 85%, or about 60 to 80, or about 65 to 75% of the volume of the hops before compression.

22. The process of any of claims 1 to 21, wherein in step (b) the water is heated at a reduced pressure for about 0.5 to 3 hours or about 0.75 to 2 hours.

23. The process of any of claims 1 to 22, wherein step (b) comprises a two-stage heating protocol.

24. The process of claim 23, wherein in the first stage the water is heated at a reduced pressure until the production of the hop extract vapour substantially slows.

25. The process of claim 23 or 24, wherein in the first stage the water is heated at a reduced pressure and in the second step the pressure is reduced by about 0.2 to 0.4 bar until the temperature of the water increases by about 5 to 10°C then the pressure is increased by 0.2 to 0.4 bar to extract further hop oil into the extract vapour.

26. The process of claim 23 or 24, wherein in the first stage heated at a reduced pressure and in the second step the pressure further reduced 0.2 to 0.4 bar to extract further hop oil into the extract vapour.

27. The process of claim 23 or 24, wherein in the first stage heated at a reduced pressure of about 0.3 to 0.5 bar below atmospheric pressure and in the second step the pressure further reduced 0.2 to 0.4 bar to extract further hop oil into the extract vapour.

28. The process of any one of claims 1 to 27, wherein the condenser comprises cooling means.

29. The process of claim 28, wherein the cooling means is cool water.

30. The process of any one of claim 3 to 29, wherein step (e) comprises separating the hop oil and the hydrosol in a separator column.

31. The process of any one of claims 3 to 30, wherein step (e) comprises conveying the liquid hop extract obtained in step (d) to a separator column, wherein the separator column comprises a collection port in fluid connection with the collection chamber such that when the liquid hop extract is conveyed into the separator column, the hop oil and hydrosol separate into an oil phase comprising hop oil and an aqueous phase comprising hydrosol and as the level of the oil phase rises, the oil phase flows through the collection port and into the collection chamber.

32. The process of claim 30 or 32, wherein the separator column further comprises an outlet valve below the collection point, wherein the value is in fluid connection with a hydrosol storage tank.

33. The process of claim 32, wherein opening the outlet valve allows the liquid hop extract in the separator column to flow into the hydrosol storage tank.

34. The process of any one of claims 4 to 33, wherein the hydrosol obtained in step (f) is conveyed to the hydrosol storage tank.

35. The process of any one of claims 4 to 34, wherein the process further comprises:g. purifying the collected hop oil of step (f).

36. The process of claim 35, wherein step (g) comprises a freeze / thaw purification and / or filtration.

37. A hop oil extract obtained by the process of any one of claims 1 to 36.

38. A hop oil extract comprising at least about 75% myrcene.

39. The hop oil extract of claims 37 or 38, wherein the hop oil extract comprises at least about 80% hop essential oils.

40. The hop oil extract of any one of claims 37 to 39, wherein the hop oil extract further comprises caryophyllene, farnesene, geraniol, linalool, humulene or a combination of two or more thereof.

41. The hop oil extract of any one of claims 37 to 40, wherein the hop oil extract comprises caryophyllene, farnesene and humulene.

42. The hop oil extract of any one of claims 37 to 41, wherein the hop oil extract comprises caryophyllene, farnesene, geraniol, linalool and humulene.

43. The hop oil extract of any one of claims 37 to 42, wherein the hop oil comprises at least 76%, or about 77%, or about 78%, or about 79%, or about 80%, or about 81%, or about 82%, or about 83%, or about 84%, or about 85%, or about 86%, or about 87%, or about 88%, or about 89%, or about 90%, or about 91%, or about 92% myrcene.

44. The hop oil extract of any one of claims 37 to 43, wherein the hop oil extract comprises about 0.1 to 10% caryophyllene.

45. The hop oil extract of any one of claims 37 to 44, wherein the hop oil extract comprises about 0.01 to 10% famesene.

46. The hop oil extract of any one of claims 37 to 45, wherein the hop oil extract comprises about 0.1 to 15% humulene.

47. The hop oil extract of any one of claims 37 to 46, wherein the hop oil extract comprises at least about 80% myrcene, about 0.1 to 5% caryophyllene, about 0.1 to 5% farnesene, and about 0.1 to 15% humulene.

48. The hop oil extract of any one of claims 37 to 47, wherein the hop oil extract comprises at least about 80% myrcene, less than about 5% caryophyllene, less than about 5% and famesene, and less than about 5% humulene.

49. The hop oil extract of any one of claims 37 to 48, wherein the hop oil extract comprises less than 0.1% alpha acids.

50. The hop oil extract of any one of claims 37 to 49, wherein the hop oil extract is essentially free of alpha acids.

51. The hop oil extract of any one of claims 37 to 50, wherein the hop oil extract comprises less than 1% iso-alpha acids.

52. The hop oil extract of any one of claims 37 to 51, wherein the hop oil extract comprises less than 0.1% iso-alpha acids.

53. The hop oil extract of any one of claims 37 to 52, wherein the hop oil extract is essentially free of iso-alpha acids.

54. The hop oil extract of any one of claims 37 to 53, wherein the hop oil extract comprises less than 1% beta acids.

55. The hop oil extract of any one of claims 37 to 54, wherein the hop oil extract comprises less than 0.1% beta acids.

56. The hop oil extract of any one of claims 37 to 55, wherein the hop oil extract is essentially free of beta acids. In at least one embodiment,57. The hop oil extract of any one of claims 37 to 56, wherein the hop oil extract comprises less than 0.1% alpha acids, less than 0.1% iso-alpha acids and less than 0.1% beta acids.

58. The hop oil extract of any one of claims 37 to 57, wherein the hop oil extract is obtained from wet hop cones, dry hop cones, hop pellets or a mixture of two or more thereof.

59. The hop oil extract of any one of claims 37 to 58, wherein the hop oil extract is obtained from a hop variety selected from Green Bullet, Motueka, Nelson Sauvin, NZ Cascade, Pacific Sunrise, Pacifica, Rakau, Riwaka, Southern Cross and a mixture of two or more thereof.

60. The hop oil extract of any one of claims 37 to 59, wherein the hop oil extract is obtained from wet hop cones, wherein hop oil extract is extracted from the wet hop cones within 24 hours of being harvested.

61. The hop oil extract of any one of claims 37 to 60, wherein the hop oil extract has a density of about 0.80 to 1.02 g / mL or about 0.85 to 1.01 g / mL or about 0.89 to 0.95 g / mL.

62. The hop oil extract of any one of claims 37 to 61 for use in a beverage, preferably a beer, a low-alcohol beer, an alcohol-free beer, a hop water, a hop tea, a seltzer, a spirit, or a kombucha.

63. The hop oil extract of any one of claims 37 to 62 for use in healthcare products or cosmetics.

64. A hop oil composition comprising the hop oil extract of any one of claims 37 to 63 and at least one solubilising agent.

65. A hop oil composition comprising:a. about 5 to 50% v / v of a hop oil extract, andb. about 50 to 95% v / v of a solubilising agent.

66. The hop oil composition of claim 64 or 66, wherein the solubilising agent is:i. a glycerol , and / orii. a propylene glycol.

67. The hop oil composition of any one of claims 64 to 66, wherein the combination of oil with a solubilising agent increases miscibility of the hop oil with aqueous solutions.

68. The hop oil composition of any of claims 64 to 67, wherein the hop oil extract is a hop oil extract according to any of any one of claims 37 to 61.

69. The hop oil composition of any one of claims 64 to 68, wherein the composition comprises about 10 to 50%, about 15 to 50%, about 20 to 50%, about 25 to 50%, about 30 to 50%, about 35 to 50%, about 40 to 50% or about 45 to 50% v / v of the hop oil extract70. The hop oil composition of any one of claims 64 to 69, wherein the composition comprises about 5 to 45%, about 5 to 40%, about 5 to 35%, about 5 to 30%, about 5 to 25%, about 5 to 20%, about 5 to 15% or about 5 to 10% v / v hop oil extract.

71. The hop oil composition of any one of claims 64 to 70, wherein the composition comprises at least about 5%, about 6%, about 7%, about 8%, about 9%, about 10%, about 11%, about 12%, about 13%, about 14%, about 15%, about 16%, about 17%, about 18%, or about 19% v / v hop oil extract.

72. The hop oil composition of any one of claims 64 to 71, wherein the solubilising agent comprises one or more polyols.

73. The hop oil composition of any one of claims 64 to 72, wherein the solubilising agent comprises one or more food grade emulsifiers.

74. The hop oil composition of any one of claims 64 to 65 or 67 to 73, wherein the solubilising agent is a glycerol, a glycol, a polysorbate, a sorbitan ester, or a combination of two or more thereof.

75. The hop oil composition of any one of claims 64 to 65 or 67 to 74, wherein the solubilising agent is glycerol, glycerol monostearate, polyglycerol polyricinoleate, polypropylene glycol, polysorbate 80, polysorbate 60, sorbitan monostearate, or a combination of two or more thereof.

76. The hop oil composition of any one of claims 64 to 65 or 67 to 75, wherein the solubilising agent is a combination of glycerol and polypropylene glycol.

77. The hop oil composition of any one of claims 64 to 76, wherein the composition comprises about 55 to 95%, about 60 to 95%, about 65 to 95%, about 70 to 95%, about 75 to 95%, about 80 to 95%, about 85 to 95% or about 90 to 95% v / v solubilising agent.

78. The hop oil composition of any one of claims 64 to 77, wherein the composition comprises about 50 to 90%, about 50 to 85%, about 50 to 80%, about 50 to 75%, about 50 to 70%, about 50 to 65%, about 50 to 60% or about 50 to 55% v / v solubilising agent.

79. The hop oil composition of any one of claims 64 to 78, wherein the composition comprises at least about 95%, about 94%, about 93%, about 92%, about 91%, about 90%, about 89%, about 88%, about 87%, about 86%, about 85%, about 84%, about 83%, about 82%, or about 81% v / v solubilising agent.

80. The hop oil composition of any one of claims 64 to 74 or 77 to 79, wherein the composition comprises about 55 to 90% v / v propylene glycol.

81. The hop oil composition of any one of claims 64 to 80, wherein the composition comprises about 0.1 to 5% v / v glycerol.

82. The hop oil composition of any one of claims 64 to 74 or 77 to 81, wherein the composition comprises about 10 to 20% v / v hop oil, about 75 to 90% v / v propylene glycol and about 0.1 to 5% v / v glycerol.

83. The hop oil composition of any one of claims 64 to 74 or 77 to 82, wherein the composition comprises about 15 to 20% v / v hop oil, about 75 to 85% v / v propylene glycol and about 0.5 to 2.5% v / v glycerol.

84. The hop oil composition of any one of claims 64 to 74 or 77 to 83, wherein the composition comprises about 20% v / v hop oil, about 79% propylene glycol and about 1% glycerol.

85. A beverage comprising the hop oil extract of any one of claims 37 to 61, or the hop oil composition of any one of claims 64 to 84.

86. The beverage of claim 85, wherein the beverage is an alcoholic beverage, a low alcohol beverage, a non-alcohol beverage, a fermented beverage, a hop tea, a hop soda, or a hop water. In at least one embodiment, the beverage is an alcoholic, a low alcohol or a nonalcoholic beer.

87. The beverage of claim 85 or 86, wherein the beverage is an alcoholic, a low alcohol or a nonalcoholic beer.

88. The beverage of any one of claims 85 to 87, wherein the beverage is a beer comprising about 0.0001% to 0.01% of the hop oil extract.

89. A process of preparing a beverage comprising the addition of the hop oil extract of any one claims 37 to 63, or the hop oil composition of any one of claims 64 to 84.

90. A process of claim 89, wherein the process involves a fermentation step.

91. A process of claim 89 or 90, wherein the hop oil extract of any one of claims 37 to 63, or the hop oil composition of any one of claims 64 to 84 is added during the fermentation step.

92. A process of any one of claims 89 to 91, wherein the hop oil extract of any one of claims 37 to 63, or the hop oil composition of any one of claims 64 to 84 is added after the fermentation step.

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