Solid delivery system

Abstract

A solid delivery system is described that includes a high terpene-containing essential oil encapsulated in an extruded carbohydrate matrix, as well as a method for producing such a solid delivery system. Such a solid delivery system is useful, for example, for imparting flavor or aroma to consumer products such as brewed beverages.

Description

[Technical field]

[0001] The present invention relates to a solid delivery system for delivering high terpene content essential oils, the system comprising droplets of such essential oils encapsulated in an extruded carbohydrate matrix. [Background technology]

[0002] It is well known in the food and beverage industry that the addition of flavor ingredients, including essential oils, contributes greatly to the palatability of consumable materials. For example, brewed beverages, such as beer, often contain hop products, which provide bitterness, flavor, and aroma to the brewed beverage, in addition to their functional use as stabilizers and antimicrobials. However, high terpene-containing essential oils undergo autoxidation and / or pyrolysis when exposed to air or heat. Thus, there can be significant obstacles when formulating with such essential oils, due to their limited processing temperature and storage stability.

[0003] For example, brewing is a complex process that utilizes harsh conditions, especially with regard to hop oils. Hop products are added at various points during this process and can be adversely affected by these harsh conditions. For example, certain components of the hop products can be stripped off or polymerized during boiling, while others can be absorbed by yeast or filtered out during production. Taking this into account, the amount of hop products remaining at the end of the brewing process is very small. Hop products can be added after brewing to enhance flavor, but they are fairly unstable and easily oxidized in air. Oxidized hop products have undesirable flavors and aromas, which means that hop products and hop derivatives tend to have a limited shelf life. There are currently available means to increase the stability of hop products, but they often contain materials that are undesirable from the standpoint of safety, storage, cost and consumer acceptance, such as ethanol or propylene glycol.

[0004] Summary of the Invention Therefore, the object of the present invention is to deliver high terpene-containing essential oils to consumer products in a safe, effective and consistent manner.For example, in some embodiments, the object of the present invention is to deliver hop products to a brewing process, or in certain preferred embodiments, to a brewed beverage in a safe, effective and consistent manner.Furthermore, it would be advantageous to provide high terpene-containing essential oils, such as hop oils, that are stable during transportation and storage, even at ambient or elevated temperatures, and remain acceptable to consumers after such transportation and storage.To this end, the present teachings relate to a solid delivery system that includes high terpene-containing essential oil droplets encapsulated in an extruded carbohydrate matrix.

[0005] Thus, in certain aspects, the present teachings relate to methods for preparing the solid delivery systems disclosed herein. In general, such methods include: a) blending a high terpene containing essential oil with a carbohydrate matrix material, an emulsifier and optionally a plasticizer under conditions of temperature and agitation to produce a homogeneous melt thereof; b) extruding the homogenous melt through a die; c) optionally cooling the homogeneous melt; d) chopping, cutting, grinding or pulverizing the homogenous melt as it exits the die or after it has cooled to form a solid delivery system; and e) washing excess high terpene containing essential oil from the surface of the solid delivery system; f) optionally drying the solid delivery system; Includes.

[0006] In some embodiments, the carbohydrate matrix comprises at least one carbohydrate selected from the group consisting of sucrose, glucose, lactose, levulose, fructose, maltose, ribose, dextrose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol, pentitol, arabinose, pentose, xylose, galactose, trehalose, hydrogenated corn syrup, hydrogenated starch hydrolysates, maltodextrin, agar, carrageenan, gum, polydextrose, derivatives, and mixtures thereof. In some embodiments, the carbohydrate matrix comprises maltodextrin or a mixture of maltodextrin and at least one substance selected from the group consisting of sucrose, glucose, lactose, levulose, maltose, fructose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol, and hydrogenated corn syrup. In some embodiments, the maltodextrin has a DE equivalent of less than 20. In some embodiments, the carbohydrate matrix comprises at least 70% by weight of maltodextrin based on the total weight of the carbohydrate matrix, hi other embodiments, the carbohydrate matrix consists essentially of or consists of maltodextrin.

[0007] In certain embodiments, the high terpene containing essential oil is at least one essential oil selected from the following essential oils: agarwood, allspice, anise, basil, bay leaf, benzoin, bergamot, black pepper, buco, camphor, cassia, cedarwood, celery, chamomile, cinnamon, clove, copaiba, cumin, cypress, eucalyptus, flax, frankincense, alpinia, ginger, grapefruit, guava, hops, hyssop, jasmine, juniper, labdanum, lavender, lemon, lemongrass, lime, manuka, marjoram, melaleuca, myrrh, nutmeg, orange, oregano, patchouli, peppermint, pine, plumeria, rose, rosemary, rosewood, sage, sandalwood, sassafras, spearmint, tangerine, tea tree, thyme, hemlock, valerian, vetiver, white fir, wintergreen, and ylang-ylang, and mixtures thereof. In some preferred embodiments, the high terpene containing essential oil comprises hops oil.

[0008] In certain embodiments, the high terpene-containing essential oil is present in an amount of about 3% to about 15% based on the total weight of the solid delivery system. In certain embodiments, the emulsifier comprises at least one vegetable lecithin. In some embodiments, the solid delivery system comprises vegetable lecithin and the high terpene-containing essential oil is present in an amount of more than 9% by weight based on the total weight of the solid delivery system. In certain embodiments, the emulsifier is present in an amount of 5% to 50% by weight of the high terpene-containing essential oil.

[0009] In some embodiments, the solid delivery system also includes a flavor, an aroma, a nutrient, or a mixture thereof.

[0010] In some aspects, the present teachings also relate to consumer products comprising the solid delivery systems disclosed herein. In some embodiments, the consumer product is a brewed beverage.

[0011] In certain embodiments, the high terpene containing essential oil, carbohydrate matrix material, emulsifier and optionally plasticizer are stirred at a temperature maintained between 90°C and 130°C.

[0012] In some embodiments, step a) comprises: a1) stirring a carbohydrate matrix material at an elevated temperature, preferably at a temperature between 110°C and 120°C, in the presence of a plasticizer, preferably where the plasticizer is water, to form a heated mixture; a2) This heated mixture i) a combination of an emulsifier and a high terpene content essential oil, or ii) Emulsifier followed by high terpene content essential oil and adding Preferably, step b) is carried out within 60 minutes of adding the high terpene containing essential oil, more preferably within 45 minutes of adding the high terpene containing essential oil.

[0013] In certain embodiments, the moisture content is maintained at 5% to 10% by weight based on the total weight of the solid delivery system during preparation of the solid delivery system disclosed herein.

[0014] In yet another aspect, the present teachings provide a method for preparing a solid delivery system, the method comprising: a1) stirring a carbohydrate matrix material at an elevated temperature, preferably at a temperature between 90°C and 130°C, in the presence of a plasticizer, preferably where the plasticizer is water, to form a heated mixture; a2) This heated mixture i) a combination of vegetable lecithin and a high terpene content essential oil, or ii) Plant lecithin followed by high terpene content essential oils to form a homogenous melt; b) extruding the homogenous melt through a die; c) optionally cooling the homogeneous melt; d) chopping, cutting, grinding or pulverizing the homogenous melt as it exits the die or after it has cooled to form a solid delivery system; and e) washing excess high terpene containing essential oil from the surface of the solid delivery system; f) drying the solid delivery system. Includes.

[0015] The present teachings also include solid delivery systems obtainable by the methods disclosed herein, preferably, the solid delivery systems have a shelf life of two years or more when stored at ambient temperature. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0016] It has been discovered that high terpene-containing essential oils can be encapsulated in a solid matrix using hot melt extrusion technology to provide a solid delivery system with excellent storage stability.Therefore, the present disclosure provides a solid delivery system that includes droplets of high terpene-containing essential oils encapsulated in an extruded carbohydrate matrix.Such solid delivery systems are cost-effective, allow the encapsulation of large amounts of high terpene-containing essential oils, and can remain stable in the carbohydrate matrix during transportation or long storage periods, and in some embodiments can be used to great effect during harsh processing techniques such as brewing.

[0017] In some preferred embodiments, the solid delivery system of the present teachings consists essentially of, and more preferably consists of, a high terpene-containing essential oil encapsulated in a carbohydrate matrix. In other particularly preferred embodiments, the solid delivery system of the present teachings consists essentially of, and more preferably consists of, a high terpene-containing essential oil encapsulated in a maltodextrin matrix with an emulsifier. In yet other particularly preferred embodiments, the solid delivery system of the present teachings consists essentially of, and more preferably consists of, a hops oil encapsulated in a maltodextrin matrix with a plant-lecithin emulsifier.

[0018] The solid delivery system disclosed herein provides a uniform distribution of high terpene-containing essential oil in the matrix, which allows for improved stability against degradation and oxidation. The uniform distribution of high terpene-containing essential oil in the matrix (and the associated improved stability) confers a longer shelf life compared to free high terpene-containing essential oil. For example, in some embodiments, the solid delivery system disclosed herein has a shelf life of at least about 6 months, such as at least about 1 year or 2 years or more in preferred embodiments, when stored at ambient temperature. In some embodiments, the solid delivery system disclosed herein has a shelf life of at least 3, 4, 5, or even 6 years or more, when stored at ambient temperature. As used herein, the term shelf life refers to less than 20% degradation, preferably less than 10% degradation, of the high terpene-containing essential oil composition. The term shelf life also refers to the sensory reception of the flavor or aroma of the high terpene-containing essential oil in the solid delivery system. The uniform distribution of high terpene containing essential oils in the matrix also provides a product with a consistent essential oil loading so that the fragrance manufacturer, flavor manufacturer or brewer can be confident in the uniformity of taste or aroma across batches or brews.

[0019] The solid delivery systems disclosed herein are also expected to have improved organoleptic properties, including, for example, enhanced mouthfeel, improved off-note masking effectiveness in consumer products into which they are incorporated, and / or a fuller and more intense impact of high terpene containing essential oils in the mouth and / or when ingested or inhaled.

[0020] High terpene content essential oil The solid delivery system disclosed herein comprises at least one high terpene-containing essential oil. As used herein, the term "high terpene-containing essential oil" refers to an essential oil having a total terpene content of more than 50% by weight based on the weight of the essential oil. Essential oils refer to compounds extracted from various parts of plants (e.g., bark, roots, leaves, flowers, fruits, etc.) that capture the scent and / or flavor from the plant. Typically, essential oils are extracted using distillation, e.g., steam extraction and / or pressure extraction methods, although other methods known to those skilled in the art may be used. "Terpene" as used herein refers to the terpene and terpenoid compounds present in such extracts. In some embodiments, the essential oils used in connection with the present teachings have a terpene content of more than 60%, more than 70%, more than 80%, more than 90%, or even more than 95% by weight based on the weight of the essential oil. In some embodiments, the essential oils used in connection with the present teachings have a mono- and sesquiterpene content of greater than 50%, greater than 60%, greater than 70%, greater than 80%, or even greater than 90% by weight based on the weight of the essential oil. In some embodiments, the essential oils used in connection with the present teachings have a mono- and sesquiterpene content of greater than 50%, greater than 60%, greater than 70%, or even greater than 80% by weight based on the weight of the essential oil. In some embodiments, the essential oils used in connection with the present teachings have a sesquiterpene content of greater than 50%, greater than 60%, greater than 70%, or even greater than 80% by weight based on the weight of the essential oil.

[0021] Exemplary high terpene containing essential oils may include, but are not limited to, the following essential oils: agarwood, allspice, anise, basil, bay leaf, benzoin, bergamot, black pepper, buco, camphor, cassia, cedarwood, celery, chamomile, cinnamon, clove, copaiba, cumin, cypress, eucalyptus, flax, frankincense, alpinia, ginger, grapefruit, guava, hops, hyssop, jasmine, juniper, labdanum, lavender, lemon, lemongrass, lime, manuka, marjoram, melaleuca, myrrh, nutmeg, orange, oregano, patchouli, peppermint, pine, plumeria, rose, rosemary, rosewood, sage, sandalwood, sassafras, spearmint, tangerine, tea tree, thyme, hemlock, valerian, vetiver, white fir, wintergreen, and ylang-ylang.

[0022] Terpene and terpenoid compounds present in such essential oils may include, but are not limited to, monoterpenes such as limonene, pinene, terpinene, sabinene, myrcene, carene, phellandrene and thujene; ​​sesquiterpenes such as cedrene, thujopsene, bulnesene, humulene, guayene, vatirenene, seichelan, cubene, valencene, zingiberene, sesquiphellandrene, curcumene, germacrene, caryophyllene, farnesene, elemene, bisabolene, zingiberene; and hemiterpenes, diterpenes, and the like.

[0023] In some embodiments, the high terpene containing essential oil does not include a high terpene containing essential oil selected from the group consisting of grapefruit, lemon, lime and orange.

[0024] In some embodiments, the solid delivery system disclosed herein comprises at least one hop oil. As used herein, the term "hop oil" refers to at least one of whole hop oil, hop oil fractions, single hop oil components, blends of hop oil components, multifunctional thiols, and hop oil derivatives. Whole hop oil can be obtained from hops using any of the methods known in the art. Hop oil fractions and components can be obtained by separation methods known in the art, including distillation, chromatography, and / or partitioning. Similarly, hop oil can be derivatized by methods known in the art.

[0025] Hop oil may contain the monoterpene myrcene, sesquiterpenes such as humulene, β-caryophyllene or farnesene, monoterpene alcohols such as linalool and geraniol, oxygenated sesquiterpenoids such as cadinol, caryophyllene oxide and humulenol II. Other hop components may also be present in hop oil, including flavor or aroma compounds such as esters, ketones, alcohols and ethers.

[0026] The amount of high terpene-containing essential oil present in the solid delivery system can vary. Generally speaking, the solid delivery system can be formulated to contain an effective amount of high terpene-containing essential oil. As used herein, the term "effective amount" refers to an amount sufficient to modify the aroma and / or flavor of the consumer product in which the solid delivery system is incorporated. For example, an effective amount of hop oil refers to an amount of hop oil sufficient to modify the aroma and / or flavor of the brewed beverage in which the solid delivery system is incorporated.

[0027] In some embodiments, the solid delivery system comprises a high terpene-containing essential oil in an amount of up to about 25% by weight, e.g., 1% to 25% by weight, based on the total weight of the delivery system. In some embodiments, the solid delivery system comprises a high terpene-containing essential oil in an amount of 3% to 15% by weight, e.g., 5% to 13% by weight, based on the total weight of the delivery system.

[0028] emulsifier During the manufacture of the solid delivery system disclosed herein, emulsifiers are used to stabilize the high terpene-containing essential oil and matrix components, thus facilitating the inclusion of the high terpene-containing essential oil in the matrix. As used herein, the term "emulsifier" refers to an agent or compound that forms or preserves an emulsion. Suitable emulsifiers are known to those skilled in the art and include materials found in documents such as GL Hasenhuettl and RW Hartel, Food emulsifiers and their applications, 1997. Emulsifiers that are particularly useful with essential oils can be found, for example, in Chilton et al. J Inst Brew, May-June 1978, 84:177-178. Fatty acid esters can also be used as emulsifiers in this context, including, for example, diacetyl tartaric acid esters of mono- and diglycerides (DATEM) and citric acid esters of mono- and diglycerides (CITREM). Additional emulsifiers useful in the context of the present invention are described, for example, in Patent Publication Nos. US20220000136, US20200246245, US20170051236, WO2020104478, US20160073663, US20150351430, US20150282508, US2014015435, to name just a few. 7, US20090041901, US20070009643, US4,242,366, US3,486,906, US20050026999, US20050220914, US20040151805, US20030096026 and US20020061354, US20020065328. The contents of these publications on emulsification are incorporated herein by reference. In some embodiments, the emulsifier is a plant-based emulsifier. In some embodiments, it may be beneficial to use an emulsifier that is present in the target consumer product or that is sourced from the same or similar materials used in the target consumer product. For example, in some embodiments, the consumer product is a brewed beverage and the emulsifier is sourced from wheat or barley.

[0029] Particularly suitable emulsifiers include animal or vegetable lecithins, such as soybean lecithin or sunflower lecithin, and its components, such as one or a combination of glycerophospholipids. In one embodiment, the emulsifier is soybean lecithin or sunflower lecithin. Sunflower lecithin may provide certain benefits because it is not considered an allergen. In some embodiments, the emulsifier is selected from one or more vegetable lecithins, and the solid delivery system includes high terpene-containing essential oil in an amount of more than 8% by weight, for example, in some embodiments, 9% by weight or more, based on the total weight of the delivery system.

[0030] The amount of emulsifier used is not particularly limited, but depends on the nature and amount of other components in the delivery system, as well as the effectiveness of the emulsifier itself. Generally speaking, the amount of emulsifier is selected relative to the weight of the high terpene-containing essential oil used. In certain embodiments, the emulsifier is present in an amount of 5% to 50% by weight relative to the weight of the high terpene-containing essential oil. In the case of vegetable lecithin, it is possible to use a small amount of emulsifier, for example 5 to 15% by weight, relative to the weight of the high terpene-containing essential oil. In some embodiments, the emulsifier is vegetable lecithin, such as soybean lecithin or preferably sunflower lecithin, present in an amount of 5% to 15% by weight relative to the weight of the high terpene-containing essential oil.

[0031] Carbohydrate Matrix The matrix composition is based on the use of common polymeric sugars, i.e., sugars and their derivatives. The solid delivery system disclosed herein comprises a carbohydrate matrix. Any carbohydrate that can be processed by extrusion techniques to form a dry extruded solid can be used as a matrix material in connection with the present teachings. Particularly useful carbohydrates include, but are not limited to, sucrose, glucose, lactose, levulose, fructose, maltose, ribose, dextrose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol, pentitol, arabinose, pentose, xylose, galactose, trehalose, hydrogenated corn syrup, hydrogenated starch hydrolysate, maltodextrin, agar, carrageenan, gum, polydextrose, derivatives and mixtures thereof.

[0032] According to certain preferred embodiments, the matrix material comprises maltodextrin or a mixture of maltodextrin and at least one of sucrose, glucose, lactose, levulose, maltose, fructose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol and hydrogenated corn syrup.

[0033] In some embodiments, maltodextrins having a specific dextrose equivalent are used. Dextrose equivalent, or "DE", is a measure of the amount of reducing sugars present in a sugar product, from which the average degree of polymerization of the material is derived. In some embodiments, the maltodextrin has a dextrose equivalent (DE) of 20 or less, such as less than 20, preferably 18.

[0034] In some embodiments, the carbohydrate matrix comprises at least 70% by weight of maltodextrin based on the total weight of the carbohydrate matrix, hi other embodiments, the carbohydrate matrix consists essentially of or consists of maltodextrin.

[0035] In some embodiments, the carbohydrate matrix material does not include hydrogenated starch hydrolysates.

[0036] In some embodiments, the carbohydrate matrix material does not include agar.

[0037] Manufacturing method The solid delivery systems of the present invention can be manufactured by an extrusion process. In some embodiments, the present teachings provide a process for preparing a solid delivery system, the process comprising: a) blending a high terpene containing essential oil with a carbohydrate matrix material, an emulsifier and optionally a plasticizer under conditions of temperature and agitation to produce a homogeneous melt thereof; b) extruding the homogenous melt through a die; c) optionally cooling the homogeneous melt; d) chopping, cutting, grinding or pulverizing the homogenous melt as it exits the die or after it has cooled to form a solid delivery system; and e) washing excess high terpene containing essential oil from the surface of the homogeneous melt or solid delivery system; f) optionally drying the solid delivery system; Includes.

[0038] Typical conditions for this process are similar to those for the processes for encapsulating hydrophobic flavors described, for example, in U.S. Pat. Nos. 4,610,890 and 4,707,367, the contents of which are incorporated herein by reference.

[0039] In certain embodiments of step a), the carbohydrate matrix material, the high terpene-containing essential oil, the emulsifier and an optional plasticizer (e.g., a certain amount of water) are mixed at a temperature near the melting point of the mixture to form a homogeneous melt.

[0040] In another embodiment of step a), some of the ingredients are added stepwise to the heated mixture, for example, one or more ingredients may be heated, e.g., in the presence of a plasticizer, followed by the addition (stepwise or in a bolus) of one or more of the remaining ingredients.

[0041] In some embodiments, step a) comprises: a1) stirring a carbohydrate matrix material at an elevated temperature, preferably at a temperature between 110°C and 120°C, in the presence of a plasticizer, preferably where the plasticizer is water, to form a heated mixture; a2) This heated mixture i) a combination of an emulsifier and a high terpene content essential oil, or ii) Emulsifier followed by high terpene content essential oil Adding Includes. In this embodiment, conditions can be selected to minimize exposure of the high terpene-containing essential oil to moisture and heat. In certain embodiments, the addition of the high terpene-containing essential oil occurs at least about 2 minutes, such as at least about 3, 4, 5, 6, 7, 8 minutes, or later, after the addition of the emulsifier. For example, in some preferred embodiments, the addition of the high terpene-containing essential oil occurs about 4 to about 8 minutes after the addition of the emulsifier. In certain preferred embodiments, step b) occurs within 60 minutes of adding the high terpene-containing essential oil to the heated mixture. In other embodiments, step b) occurs within 45 minutes, or even 30 minutes, of adding the high terpene-containing essential oil to the heated mixture. In these embodiments, the carbohydrate matrix material, plasticizer, and emulsifier mixture are typically stirred prior to the addition of the high terpene-containing essential oil.

[0042] In certain embodiments of a1), the carbohydrate matrix material is combined with excess water (e.g., to produce a moisture content of 15% to 20% by weight) and the mixture is heated to remove some of the excess water to obtain the desired or required moisture content (e.g., a moisture content of 5% to 8% by weight).

[0043] Steps a) and b) are carried out at a temperature appropriate to maintain a homogeneous melt until the desired cooling. Typically, the temperature is raised to, for example, at or above the boiling point of water, or slightly above the boiling point of water, but preferably not exceeding 130°C. Thus, in certain embodiments, the high terpene-containing essential oil, carbohydrate matrix material, emulsifier and optionally plasticizer in step a) are stirred at a temperature maintained between 90°C and 130°C. In some embodiments, the temperature of steps a) and b) is maintained between 110°C and 120°C, for example between 110°C and 120°C. In some embodiments, the temperature is maintained within + / - 5°C of the boiling point of the molten mixture. In some embodiments, the temperature is maintained above the glass transition temperature of the carbohydrate matrix.

[0044] Extrusion of the homogeneous melt can be carried out using several techniques, depending on the size and properties desired in the final product. The methods described herein do not require special extruder equipment and can be carried out, for example, using single or twin screw extruders typically used in known "wet extrusion" or "dry blend" (also called "flash flow") techniques. Twin screw, single screw, and ram extruders are commercially available, including those equipped with extrudate chopping cutters and / or temperature control mechanisms to gradually increase the temperature of the mixture as it progresses through the extruder and into the die holes.

[0045] Additionally, the extruded solid may take one or more of a variety of forms known in the art of extrusion, including, for example, powders of various particle size distributions, rods, flakes, strands, filaments, etc. The extruded solid may also be further processed, for example, by grinding (or cryogenic grinding), pulverizing, crushing, shredding, or sieving, to reduce its size. Such further processing may be appropriate, for example, when a finely atomized powder is desired.

[0046] In some embodiments, the homogeneous melt is cooled to a temperature below the glass transition temperature of the matrix as it is extruded through the die. In yet other embodiments, the homogeneous melt is extruded through the die at a temperature above its glass transition temperature and cooled in a liquid solvent to reduce the temperature below its glass transition temperature (e.g., to form a glassy material). These embodiments produce solid extruded material in the form of filaments or strands. The shape and size of these filaments or strands can be adjusted as a function of the extrusion parameters. The extruded granules or particles can then be made, for example, by chopping, cutting, grinding, or otherwise breaking or crushing the cooled extruded material. However, breaking or crushing can result in material with a large size distribution and can also damage the encapsulation around the high terpene-containing essential oil, thus adversely affecting the high terpene-containing essential oil loading in the matrix.

[0047] In other embodiments, the homogeneous melt is chopped or cut when extruded through a die in a plastic state above its glass transition temperature. Such techniques advantageously provide encapsulation materials with uniform sizes that allow for a more uniform and dynamically well-defined release of the encapsulated high terpene-containing essential oil. In some embodiments, when significant amounts of plasticizers (e.g., water) are used in the so-called "wet granulation" technique, the method may require an additional drying step to remove the water / plasticizer. Thus, the solid delivery system may be dried to the desired (depending on the application or required) moisture content. Efficient drying may be aided by the use of anti-caking agents, such as silicon oxide.

[0048] In some embodiments, the method includes a washing step to wash the high terpene-containing essential oil from the surface of the product. The high terpene-containing essential oil may be washed from the surface of the homogeneous melt as it is extruded from the die or solid delivery system (i.e., once the homogeneous melt has cooled), or this step may be performed as the material cools from the melt to a solid. For example, in some embodiments, the homogeneous melt is extruded, cooled in a solvent, chopped, cut, ground or otherwise divided into particles, and the particles (i.e., particles of a solid delivery system) are washed. In other embodiments, the homogeneous melt passes through a wash, e.g., a spray, as it is extruded from the die. In some embodiments, the high terpene-containing essential oil is washed from the surface of the homogeneous melt and / or the solid delivery system using a solvent. The solvent is not particularly limited, but a solvent that does not significantly dissolve the carbohydrate matrix is ​​preferred. In some embodiments, the solvent is cooled. Suitable solvents include alcohols, such as methanol, ethanol, or isopropanol.

[0049] The temperature and pressure conditions under which the extrusion process is carried out are known to the skilled artisan and can be adjusted without particular effort to the particular extrudate as a function of the nature of the components present in the melt and also as a function of the quality of the product desired to be obtained, i.e. its particle size distribution, shape and size. In a particular embodiment, the homogeneous melt is heated in an extruder, for example a twin-screw extruder, and extruded through a die of suitable size. Extrusion dies known in the art are typically thick circular discs containing one or more openings with a diameter suitable for forming the desired profile. However, "die" is also used herein to refer to a nozzle or any other applicable opening located in a suitable position relative to the extruder. The diameter typically ranges from about 0.250 to about 10 mm, preferably 0.7 to 2.0 mm. However, much larger diameters of the die are also possible. The die orifice is at the same temperature as the rest of the apparatus and can be equipped with a cutting device for chopping the melt as it leaves the die.

[0050] In some embodiments, the extruder assembly maintains the temperature of the mixture at a predetermined temperature above the glass transition temperature of the carbohydrate matrix to keep the mixture in the form of a molten mass. Preferably, the extruder assembly maintains the temperature of the mixture at between 90°C and 130°C. In some embodiments, the extruder applies a predetermined pressure to the material moving through the die, which is adjusted to a value appropriate to maintain homogeneity of the melt. A typical pressure used for extrusion is 100 bar (10 7 The preferred pressure is generally between 1 bar and 20 bar (10 Pa). 5 ~2×10 6 Pa).

[0051] In certain embodiments, little or no plasticizer is required for the methods described herein. In such embodiments where little or no plasticizer is present, it may be necessary to pump the mixture (which may be in a substantially solid form) into an extruder (e.g., under higher pressure) under efficient mixing to ensure the formation of a homogenous melt and to obtain a stable extruded product.

[0052] The glass transition temperature of the high terpene-containing essential oil / carbohydrate mixture depends on the amount of water added to the initial mixture. It is well known in the art that an increase in the proportion of water reduces the Tg. Thus, in certain embodiments, a small amount of water is used as a plasticizer in the methods described herein. The addition of a small amount of water can provide a homogeneous melt with a glass transition temperature (Tg) close to, and preferably substantially the same as, the desired Tg of the final product. This is in contrast to other methods such as wet granulation, where the Tg of the mixture is quite different from the desired Tg of the final product. In some embodiments, water is added to obtain a Tg above room temperature, preferably above 40° C. Having a Tg above room temperature allows for storage of the solid delivery system at ambient temperature in the form of free-flowing granules. In embodiments where the Tg of the homogeneous melt is close to or substantially the same as the desired Tg of the final product, it is possible to omit an additional drying step after extrusion.

[0053] As the nature and amount of carbohydrate matrix material, emulsifier and high terpene-containing essential oil vary, the water content utilized to achieve the desired Tg also varies widely. In some embodiments, a water content of less than 10% by weight based on the total weight of the solid delivery system is used during mixing and maintained during extrusion of the homogeneous melt. In some embodiments, the carbohydrate matrix comprises a material having a DE (dextrose equivalent) of 18 and a water content of 5% to 10% by weight based on the total weight of the solid delivery system is used during mixing and maintained during extrusion of the homogeneous melt.

[0054] Purpose The present teachings also relate to consumer products that at least in part comprise the solid delivery system described herein.Relevant consumer products depend on the nature and identity of the high terpene-containing essential oil that is encapsulated in the solid delivery system.For example, wood oil (e.g., sandalwood oil) may be more suitable for personal care products, while fruit oil (e.g., lemon oil or orange oil) may be more suitable for food products such as beverages.

[0055] In some embodiments, the high terpene containing essential oil is hops oil and the consumer product is a brewed beverage, such as beer. In some embodiments, the high terpene containing essential oil is hops oil and the consumer product is not a brewed or alcoholic beverage, but the solid delivery system is added to impart a beer-like flavor thereto.

[0056] The concentrations at which the disclosed solid delivery systems can be incorporated into such consumer products vary widely and depend on the nature of the consumer product and the particular solid delivery system itself (e.g., the nature of the high terpene-containing essential oil incorporated into the solid delivery system).Typical concentrations include, but are not limited to, concentrations ranging from parts per million (ppm) to several percent by weight of the final consumer product in which they are included.

[0057] For example, one skilled in the art of brewing technology can select an appropriate concentration based on consumer preferences for hoppy levels. In some embodiments, the solid delivery systems disclosed herein partially or completely replace sugar components when present in consumer products.

[0058] At least in part, as a result of the high terpene-containing essential oil being homogeneously and uniformly distributed and encapsulated within the carbohydrate matrix, the solid delivery system disclosed herein provides stability against moisture and oxygen, preventing the degradation of the high terpene-containing essential oil.The high terpene-containing essential oil can be loaded in the carbohydrate matrix at a relatively high concentration, and the encapsulated high terpene-containing essential oil is not susceptible to oxidation / degradation, so the solid delivery system disclosed herein can be easily transported, handled, stored, and then added to consumer products as needed.For example, encapsulated hop oil can be added directly to brewed beverages after fermentation.

[0059] In certain embodiments, the solid delivery system disclosed herein can also withstand harsh processing and / or manufacturing conditions better than non-encapsulated essential oils. As used herein, "withstand" refers to the ability to maintain the essential oil in a consumer product in its desired form, whether it is identical (or functionally the same) as the original essential oil or modified in a targeted manner. For example, the solid delivery system, in certain embodiments, can withstand heat and / or chemical treatments when incorporated into a consumer product. With respect to hop oils in particular, the solid delivery system disclosed herein can withstand the brewing process in certain embodiments better than non-encapsulated hop oils. Thus, in some embodiments, the solid delivery system disclosed herein is added to the brewing process, for example, to the brew kettle, whirlpool, fermenter, bright beer tank, before filtration, or any combination thereof. The brewer will be able to determine the type and amount of hop oil that will be most beneficial at any targeted stage of the brewing process. For example, humulene and β-caryophyllene terpenes in hop oils can be easily oxidized during the brewing process to form epoxides such as caryophyllene epoxide and humulene epoxide, among other oxidation products. Such epoxides can be further reorganized into allylic alcohols such as humulenol II, caryophyllenol, and caryophylladienol. These oxidation and reorganization products are more polar and can survive the brewing process and ultimately end up in the finished beer, typically imparting a spicy and herbal hop aroma characteristic of the "kettle hop" or "noble hop" aromas found in traditional pilsner-type beers. A solid delivery system can then be produced with the specific type and amount of hop oil and added to the brewing process at the specific targeted stage.

[0060] In some embodiments, the solid delivery system also contains additional hydrophobic flavorings, aromatic oils, nutrients, or mixtures thereof. Such materials can be, for example, spices, herbs, fruit oils and extracts, vegetable oils and extracts, or mixtures thereof. Flavors used in brewing include anise, chamomile, cardamom, chili, cinnamon, clove, coriander, fennel, fenugreek, ginger root, ginseng, hibiscus, lavender, lemongrass, juniper, lemon (peel), licorice root, lime (peel), peppercorn, peppermint, sweet orange (peel), bitter orange (peel), rooibos, rosehip, sage, stevia, turmeric, and yerba mate.

[0061] If desired, adjuvants (e.g., food grade colorants, etc.) may be added in a commonly known manner to the solid delivery systems disclosed herein to provide colored solid delivery systems.

[0062] In certain embodiments, the present disclosure provides a kit or flavor formulation intended for flavoring consumer products.The kit or formulation comprises at least one solid delivery system disclosed herein, optionally in combination with one or more additional hydrophobic flavors, aroma oils or nutrients, which can also be separately incorporated into solid matrix, for example carbohydrate matrix. EXAMPLES

[0063] The present invention will now be described in further detail by the following examples, which should not be construed as limiting. Example 1. Encapsulation of hop oil in a carbohydrate matrix using soy lecithin [Table 1]

[0064] A syrup mixture of sucrose and maltodextrin was prepared by dissolving the solids in demineralized water in a solid / water ratio of 80 / 20 (by weight). The syrup mixture was heated to boiling. The temperature was increased to 115°C-118°C to reduce the water content to 7-8% w / w. While the hot melt was kept at this elevated temperature, a mixture of oil and soy lecithin (ratio 10 / 1) was added to the hot melt and dispersed into small oil droplets by mechanical agitation.

[0065] The hot melt emulsion was extruded through a nozzle to form strands, which were then rapidly solidified by contact with an agitated bath of cold isopropyl alcohol. Mechanical agitation in the isopropyl alcohol was used to wash out the solid strands (in the form of small irregular rods). The resulting solid material was then recovered from the isopropyl alcohol bath and dried.

[0066] The final products had a water content of 4.4-5.0 wt.% (measured using Karl Fischer titration techniques). Low-field NMR techniques confirmed that the final products, which were stable against oxidative degradation, contained 9.4-10.0 wt.% oil.

[0067] Example 2. Encapsulation of high terpene content essential oils in a carbohydrate matrix The same process as described in Example 2 is used, except that the hops oil is replaced with one or more of the following high terpene containing essential oils: Lemon oil; Grapefruit oil; Orange oil; Bergamot oil; Cedarwood oil; Patchouli oil; Vetiver oil; or Ginger oil.

[0068] The resulting solid delivery system has comparable loading and properties to Example 1, is easy to handle as a solid, and is stable against oxidative degradation.

[0069] Example 3 Encapsulation of hop oil into a carbohydrate matrix using sunflower lecithin [Table 2]

[0070] A syrup mixture of sucrose and maltodextrin was prepared by dissolving the solids in demineralized water in a solid / water ratio of 80 / 20 (by weight). The syrup mixture was heated to boiling. The temperature was increased to 115°C-118°C to reduce the water content to 7-8% w / w. While the hot melt was kept at this elevated temperature, a mixture of hop oil and sunflower lecithin (ratio 10 / 1) was added to the hot melt and dispersed into small oil droplets by mechanical agitation.

[0071] The hot melt emulsion was extruded through a nozzle to form strands, which were then rapidly solidified by contact with an agitated bath of cold isopropyl alcohol. Mechanical agitation in the isopropyl alcohol was used to wash out the solid strands (in the form of small irregular rods). The resulting solid material was then recovered from the isopropyl alcohol bath and dried.

[0072] Low-field NMR techniques confirmed that the final product, which was stable against oxidative degradation, contained 9.3 wt. % oil.

[0073] Example 4 Encapsulation of Hops Oil Components The same process as described in Example 1 is used, except that the hops oil is replaced with one or more of the following hops ingredients, each of which can be supplied, for example, by Kalsec USA: ·Liquid hop oil sesquiterpene fraction consisting of 31% β-caryophyllene and 36% humulene. A liquid hop oil fraction containing 55% sesquiterpene epoxides including caryophyllene epoxide, humulene epoxide I, II and III. A liquid hop oil blend consisting of monoterpene and sesquiterpene hydrocarbons, monoterpene alcohols, epoxides, esters and ketones.

[0074] The resulting solid delivery system has comparable loading and properties to Example 1, is easy to handle as a solid, and is stable against oxidative degradation.

[0075] Example 5 Encapsulation of Hops Oil and Plant Extract Blends The same process is used as described in Example 1, except that hops oil is replaced with a liquid hops oil monoterpene fraction and a blood orange plant extract blend. The resulting solid delivery system has comparable loadings and properties to Example 1, is an easy to handle solid, and is stable to oxidative degradation.

[0076] Example 6 Encapsulation of Hop Oil Ingredients and Natural Flavors The same process as described in Example 1 is used, except that the hops oil is replaced by a liquid hops oil blend consisting of hops monoterpene and sesquiterpene hydrocarbons, hops monoterpene alcohols, hops epoxides, hops esters, hops ketones and other natural flavors derived from non-hops plant sources. The resulting solid delivery system has comparable loadings and properties to Example 1, is an easy to handle solid, and is stable to oxidative degradation.

[0077] Example 7 Brewing with a Solid Delivery System A solid delivery system substantially as described in Examples 1 or 3-6, or combinations and variations thereof, is added to a wort produced from malted barley, wheat, other brewing grains, extracts of these brewing raw materials, or any combination thereof. The hopped wort is then converted to finished beer by traditional methods known to those skilled in the art, which may include boiling, separation of insoluble species, cooling the hopped wort, fermentation with yeast, conditioning, filtering, and other operations. The resulting beverage is characterized by a pronounced hop aroma and flavor without significant bitterness imparted by the encapsulated product. Alternatively, the encapsulated hop components are added to the wort solution at any time after the boiling step and / or before the sugars are fermented with yeast.

[0078] Example 8 Post-fermentation addition of solid delivery systems To a fermented beverage produced by traditional processes known to those skilled in the art is added an appropriate amount of a solid delivery system substantially as described in Examples 1 or 3-6, or combinations or variations thereof. The addition of the encapsulated hops component is performed either before or after final filtration of the beverage by methods known to those skilled in the art. The resulting beverage is characterized by a pronounced hop aroma and flavor without significant bitterness imparted by the encapsulated product.

[0079] Example 9. Stability of solid delivery systems containing high terpene content essential oils Encapsulated essential oils prepared according to the methods described in Examples 1-6 are stored at ambient temperature for two years. The same essential oil blends (non-encapsulated) having the same monoterpene and sesquiterpene compositions are diluted to 0.1% in propylene glycol and 1% in ethanol and stored at ambient temperature for two years. The data show that the encapsulated hop oil compositions surprisingly have significantly higher oxidative stability compared to liquid formulations containing the same essential oil blends.

[0080] After a two-year storage period, both the solid encapsulated product and the liquid product in propylene glycol and ethanol are evaluated by analytical and sensory evaluation methods. Sensory evaluation by trained panelists demonstrated oxidized flavors in the liquid products, while the flavor and aroma of the encapsulated essential oils remained identical to the flavor and aroma of the same essential oils stored in a freezer for the same period of time.

[0081] Analytical evaluation indicates that the essential oil composition of the encapsulated essential oil after two years is identical to the profile of the essential oil blend at the time of encapsulation. There is no sign of polymerization, oxidation or degradation of the essential oil components. Meanwhile, both liquid forms show evidence of polymerization and oxidation products of terpenes.

Claims

1. 1. A method for preparing a solid delivery system, the method comprising: a) blending a high terpene containing essential oil with a carbohydrate matrix material, an emulsifier and optionally a plasticizer under temperature and agitation conditions to produce a homogeneous melt thereof; b) extruding the homogenous melt through a die; c) optionally cooling the homogeneous melt; d) chopping, cutting, grinding or pulverizing the homogenous melt as it exits the die or after it has cooled to form the solid delivery system; e) washing excess high terpene containing essential oil from the surface of said solid delivery system; f) optionally drying the solid delivery system; A method comprising:

2. 10. The method of claim 1, wherein the high terpene containing essential oil, carbohydrate matrix material, emulsifier and optionally plasticizer are stirred at a temperature maintained between 90°C and 130°C.

3. Step a) is a1) stirring said carbohydrate matrix material at an elevated temperature, preferably at a temperature between 110°C and 120°C, in the presence of a plasticizer, preferably wherein the plasticizer is water, to form a heated mixture; a2) Adding the heated mixture i) a combination of said emulsifier with said high terpene content essential oil, or ii) the emulsifier followed by the high terpene content essential oil Adding Including, Preferably, step b) is carried out within 60 minutes of adding the high terpene content essential oil. The method according to claim 1 or 2.

4. The method of any one of claims 1 to 3, wherein the moisture content is maintained between 5% and 10% by weight based on the total weight of the solid delivery system.

5. 5. The method according to any one of claims 1 to 4, wherein the carbohydrate matrix comprises at least one carbohydrate selected from the group consisting of sucrose, glucose, lactose, levulose, fructose, maltose, ribose, dextrose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol, pentitol, arabinose, pentose, xylose, galactose, trehalose, hydrogenated corn syrup, hydrogenated starch hydrolysates, maltodextrin, agar, carrageenan, gums, polydextrose, derivatives and mixtures thereof, preferably the carbohydrate matrix comprises maltodextrin or a mixture of maltodextrin and at least one material selected from the group consisting of sucrose, glucose, lactose, levulose, maltose, fructose, isomalt, sorbitol, mannitol, xylitol, lactitol, maltitol and hydrogenated corn syrup.

6. The method according to any one of claims 1 to 5, wherein the carbohydrate matrix comprises at least 70% by weight of maltodextrin relative to the total weight of the carbohydrate matrix, preferably the carbohydrate matrix consists of maltodextrin.

7. The high terpene-containing essential oil is selected from the group consisting of agarwood, allspice, anise, basil, bay leaf, benzoin, bergamot, black pepper, bucco, camphor, cassia, cedarwood, celery, chamomile, cinnamon, clove, copaiba, cumin, cypress, eucalyptus, flax, frankincense, alpinia speciosa, ginger, grapefruit, guava, hops, hyssop, jasmine, juniper, labdanum, lavender, lemon, lemongrass, lime, manuka, marjoram, melaleuca, myrrh, and jujube.

7. The method of any one of claims 1 to 6, wherein the high terpene containing essential oil is at least one essential oil selected from the group consisting of essential oils of laurel, orange, oregano, patchouli, peppermint, pine, plumeria, rose, rosemary, rosewood, sage, sandalwood, sassafras, spearmint, tangerine, tea tree, thyme, hemlock, valerian, vetiver, white fir, wintergreen and ylang ylang and mixtures thereof, preferably said high terpene containing essential oil comprises hops oil.

8. 8. The method of any one of claims 1 to 7, wherein the high terpene containing essential oil is present in an amount of 3% to 15% by weight, based on the total weight of the solid delivery system.

9. The method of any one of claims 1 to 8, wherein the emulsifier comprises one or more vegetable lecithins.

10. 10. The method of any one of claims 1 to 9, wherein the emulsifier is present in an amount of 5% to 50% by weight of the high terpene containing essential oil.

11. The method of any one of claims 1 to 10, further comprising a flavour, an aroma, a nutrient, or a mixture thereof.

12. 1. A method for preparing a solid delivery system, the method comprising: a1) stirring a carbohydrate matrix material at an elevated temperature, preferably at a temperature between 90°C and 130°C, in the presence of a plasticizer, preferably where the plasticizer is water, to form a heated mixture; a2) Adding the heated mixture i) a combination of vegetable lecithin and a high terpene-containing essential oil, or ii) Plant lecithin followed by said high terpene-containing essential oil to form a homogenous melt; b) extruding the homogenous melt through a die; c) optionally cooling the homogeneous melt; d) chopping, cutting, grinding or pulverizing the homogenous melt as it exits the die or after it has cooled to form the solid delivery system; e) washing excess high terpene containing essential oil from the surface of said solid delivery system; f) drying the solid delivery system; A method comprising:

13. A solid delivery system obtainable by the method according to any one of claims 1 to 12, preferably said solid delivery system having a shelf life of 2 years or more when stored at ambient temperature.

14. 14. The solid delivery system of claim 13, wherein the emulsifier comprises at least one plant lecithin and the high terpene containing essential oil comprises hops oil present in an amount greater than 9% by weight based on the total weight of the solid delivery system, and preferably the solid delivery system has a shelf life of 3 years or more when stored at ambient temperature.

15. 15. A consumer product comprising the solid delivery system of claim 13 or claim 14, preferably said consumer product being a brewed beverage.

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