Emulsion composition and method for producing same

Abstract

[Problem] To provide an emulsion composition in which β-caryophyllene contained is stable and an aroma derived from the β-caryophyllene does not attenuate or deteriorate. [Solution] Provided is an emulsion composition containing the following components (A), (B), and (C): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (C) a phospholipid. Also provided is an emulsion composition containing the following components (A), (B), and (D): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (D) a sucrose fatty acid ester. Further provided is an emulsion composition containing the following components (A), (B), (C), and (D): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, (C) a phospholipid, and (D) a sucrose fatty acid ester.

Description

Emulsion composition and method for producing the same

[0001] The present invention relates to an emulsion composition, and more particularly to at least one of an emulsion composition containing the following components (A), (B), and (C): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (C) a phospholipid; an emulsion composition containing the following components (A), (B), and (D): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (D) a sucrose fatty acid ester; and an emulsion composition containing the following components (A), (B), (C), and (D): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, (C) a phospholipid, and (D) a sucrose fatty acid ester.

[0002] β-caryophyllene (CAS registration number 87-44-5, molecular formula C １５ H ２４ β-Caryophyllene (molecular weight 204.35 or 204.36) is a terpene compound found in essential oils such as black pepper, basil, oregano, cinnamon, hops, rosemary, hemp, cloves, and is approved by the U.S. Food and Drug Administration (FDA) as a food flavoring agent. β-Caryophyllene is a selective agonist of the cannabinoid receptor type 2 (CB2), and has been reported to exhibit antioxidant, anti-inflammatory, analgesic, sleep-promoting, hormone-stabilizing, stress-relieving, and anticonvulsant effects (see, for example, Non-Patent Document 1 listed below).

[0003] As described above, β-caryophyllene is an aroma component with excellent effects, and its effects are exhibited by nasal absorption, etc. However, since it has a double bond in its molecule, it is prone to autoxidation due to the influence of air, etc., and therefore has stability problems, such as the attenuation and deterioration of its aroma over time when stored for a long period of time.

[0004] It is generally known that many fat-soluble components are easily oxidized, and that emulsification can suppress this oxidation. For example, Patent Document 1 below discloses an emulsion composition containing a phospholipid, an oily component, and a surfactant, characterized in that the content of the surfactant is more than 0.5 times the content of the oily component and more than 5 times the content of the phospholipid. Also, Patent Document 2 discloses a stable emulsion composition containing (a) a fat-soluble component, (b) a phospholipid, (c) a polyol, (d) water, (e) a sucrose fatty acid ester, and (f) a polyglycerin fatty acid ester, wherein the content of (b) the phospholipid is 2.0 to 15.0 parts by weight per 100 parts by weight of the entire emulsion composition, and the weight ratio of (f) the polyglycerin fatty acid ester to 1 part by weight of (e) the sucrose fatty acid ester is 0.1 to 0.9 parts by weight.

[0005] Meanwhile, Non-Patent Document 2 below describes an emulsion (emulsion composition) containing lecithin and sucrose monopalmitate (sucrose fatty acid ester) with an essential oil containing β-caryophyllene, such as clove oil or holy basil oil, as the active ingredient, and also describes that the emulsion (emulsion composition) containing lecithin and sucrose monopalmitate stabilizes the active ingredient for a long period of time. Non-Patent Document 3 below also describes a microemulsion (emulsion composition) containing clove oil, soybean lecithin, and sucrose octanoate ester (sucrose fatty acid ester). Given the description in Non-Patent Document 2 that clove oil contains β-caryophyllene, it can be said that the clove oil-containing microemulsion (emulsion composition) of Non-Patent Document 3 contains β-caryophyllene.

[0006] On the other hand, Non-Patent Document 4 below describes that although β-caryophyllene is a useful active ingredient with various physiological activities, it has problems such as its susceptibility to oxidation in air and its low solubility, and that these problems should be solved in formulation. It also describes that nanoemulsions obtained using certain surfactants prevent the oxidation of β-caryophyllene and exhibit good stability.

[0007] Patent Publication No. 2008-154577 International Publication No. 2016 / 031954 Pamphlet

[0008] Ilaria Ceccarelli et al. , Frontiers in Neuroscience, 14:P1-11, 2020Ghada SASSI et al. , Journal of Food Science, Vol. 87, No. 9, p. 3822-3840, 2022 Linhan ZHANG et al. , Food Chemistry, Vol. 165, p. 113-118, 2014 Pauline S. SANTOS et al. , Current Pharmaceutical Design, Vol. 24, No. 29, p. 3440-3453, 2018

[0009] However, β-caryophyllene is easily oxidized due to air, heat, water, metal ions, compounded ingredients, and the like, and even when the above-mentioned emulsification processing techniques are applied, sufficient effects for suppressing the decay, deterioration, and denaturation of the fragrance have not been obtained. Therefore, it is desired to develop an emulsion composition in which the contained β-caryophyllene is stable, has excellent storage properties, and in which the decay and deterioration of the β-caryophyllene fragrance is suppressed.

[0010] On the other hand, the emulsion compositions disclosed in Non-Patent Documents 2 and 3 do not contain polyglycerol fatty acid esters, and the present inventors have clarified that emulsion compositions that do not contain polyglycerol fatty acid esters cannot stabilize the β-caryophyllene contained therein.

[0011] On the other hand, it is not easy to realize that β-caryophyllene contained in an emulsion composition that does not contain a polyglycerol fatty acid ester cannot be stabilized simply by combining Non-Patent Document 4 with well-known technical documents.

[0012] The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide an emulsion composition in which the β-caryophyllene contained therein is stable and the fragrance derived from β-caryophyllene is not attenuated or deteriorated.

[0013] As a result of extensive research, the present inventors have found that an emulsion composition containing β-caryophyllene, a polyglycerol fatty acid ester, and a phospholipid and / or a sucrose fatty acid ester stabilizes the β-caryophyllene contained therein, has excellent storage stability, and inhibits decay and deterioration of the aroma of β-caryophyllene, and have completed the following inventions.

[0014] (1) An emulsion composition containing the following components (A), (B), and (C): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (C) a phospholipid.

[0015] (2) An emulsion composition containing the following components (A), (B), and (D): (A) β-caryophyllene, (B) a polyglycerin fatty acid ester, and (D) a sucrose fatty acid ester.

[0016] (3) The emulsion composition described in (1) containing (D) a sucrose fatty acid ester.

[0017] (4) The emulsion composition according to any one of (1) to (3), wherein the HLB value of the polyglycerol fatty acid ester (B) is 2 to 16.1.

[0018] (5) The emulsion composition according to (2) or (3), wherein the HLB value of the (D) sucrose fatty acid ester is 2 to 19.

[0019] (6) The emulsion composition according to (1), having a weighted average HLB value of 10 to 20.

[0020] (7) The emulsion composition according to (2), having a weighted average HLB value of 10 to 20.

[0021] (8) The emulsion composition according to (3), having a weighted average HLB value of 10 to 20.

[0022] (9) The emulsion composition according to any one of (1) to (3), wherein the weight ratio of the amounts of (A) β-caryophyllene and (B) polyglycerol fatty acid ester is 3 to 200 parts by weight of the (B) polyglycerol fatty acid ester to 100 parts by weight of (A) β-caryophyllene.

[0023] (10) The emulsion composition according to any one of (1) to (3), wherein the content of (B) polyglycerol fatty acid ester in the emulsion composition is 1 to 20 parts by weight per 100 parts by weight of the emulsion composition.

[0024] (11) The emulsion composition according to (1) or (3), wherein the weight ratio of the amounts of (A) β-caryophyllene and (C) phospholipid is 0.5 to 100 parts by weight of (C) phospholipid to 100 parts by weight of (A) β-caryophyllene.

[0025] (12) The emulsion composition according to (1) or (3), wherein the content of the phospholipid (C) in the emulsion composition is 0.1 to 10 parts by weight per 100 parts by weight of the emulsion composition.

[0026] (13) The emulsion composition according to (2) or (3), wherein the weight ratio of the amounts of (A) β-caryophyllene and (D) sucrose fatty acid ester is 0.5 to 200 parts by weight of (D) sucrose fatty acid ester per 100 parts by weight of (A) β-caryophyllene.

[0027] (14) The emulsion composition according to (2) or (3), wherein the content of (D) sucrose fatty acid ester in the emulsion composition is 0.1 to 20 parts by weight per 100 parts by weight of the emulsion composition.

[0028] (15) A composition according to any one of (1) to (3), which contains an antioxidant.

[0029] (16) An emulsion composition described in any one of (1) to (3), which is a pharmaceutical composition or a food or beverage composition.

[0030] (17) A method for producing an emulsion composition, comprising: a step of preparing an oil phase using β-caryophyllene, a polyglycerol fatty acid ester, and a phospholipid; and a step of emulsifying the prepared oil phase, or a step of mixing the prepared oil phase with a separately prepared aqueous phase and emulsifying the mixture.

[0031] (18) A method for producing an emulsion composition, comprising the steps of: preparing an oil phase using β-caryophyllene and a polyglycerol fatty acid ester; preparing an aqueous phase using a sucrose fatty acid ester; mixing the prepared oil phase and aqueous phase; and emulsifying the mixed oil phase and aqueous phase.

[0032] (19) A method for stabilizing β-caryophyllene contained in an emulsion composition, comprising a step of blending β-caryophyllene, a polyglycerol fatty acid ester, and a phospholipid into an oil phase.

[0033] (20) A method for stabilizing β-caryophyllene contained in an emulsion composition, comprising the steps of: blending β-caryophyllene and a polyglycerol fatty acid ester into an oil phase; and blending a sucrose fatty acid ester into an aqueous phase.

[0034] According to the present invention, it is possible to provide an emulsion composition in which the β-caryophyllene contained therein is stable and the fragrance derived from β-caryophyllene does not fade or deteriorate.

[0035] The emulsion composition of the present invention, its production method, and a method for stabilizing β-caryophyllene contained in the emulsion composition are described in detail below. The emulsion composition of the present invention is an emulsion composition containing the following components (A), (B), and (C): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (C) a phospholipid; an emulsion composition containing the following components (A), (B), and (D): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (D) a sucrose fatty acid ester; and an emulsion composition containing the following components (A), (B), (C), and (D): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, (C) a phospholipid, and (D) a sucrose fatty acid ester.

[0036] In the present invention, the term "emulsion" refers to a system in which another liquid that is immiscible with the liquid in question is dispersed as small droplets, and such a state is referred to as an emulsion composition. The emulsion composition of the present invention corresponds to at least one of the following: (A) β-caryophyllene, (B) polyglycerol fatty acid ester, (C) phospholipid; (A) β-caryophyllene, (B) polyglycerol fatty acid ester, (D) sucrose fatty acid ester; and (A) β-caryophyllene, (B) polyglycerol fatty acid ester, (C) phospholipid, (D) sucrose fatty acid ester.

[0037] As described above, the (A) β-caryophyllene used in the present invention is an essential oil component contained in black pepper, basil, oregano, cinnamon, hops, rosemary, cannabis, hemp, cloves, and the like. Therefore, it can be extracted and purified from these materials by a method appropriately selectable by a person skilled in the art and used, or a commercially available product can also be used.

[0038] The β-caryophyllene (A) that can be used in the present invention can be appropriately selected within a range that does not impair the characteristics of the present invention, and is not particularly limited. From the viewpoint of the stability of β-caryophyllene in the emulsion composition, however, the purity of the β-caryophyllene (A) is preferably 50% or more, more preferably 60% or more, even more preferably 70% or more, still more preferably 80% or more, and particularly preferably 90% or more.

[0039] Furthermore, the content of (A) β-caryophyllene in the emulsion composition according to the present invention is preferably 1 to 50 parts by weight, more preferably 2 to 40 parts by weight, more preferably 3 to 40 parts by weight, more preferably 5 to 35 parts by weight, more preferably 7 to 35 parts by weight, more preferably 7 to 30 parts by weight, even more preferably 7 to 25 parts by weight, still more preferably 7 to 20 parts by weight, and particularly preferably 7 to 15 parts by weight, per 100 parts by weight of the emulsion composition. In this specification, numerical ranges expressed using "to" or "from" mean a range that includes the numerical values ​​before and after "to" or "from" as the lower and upper limits.

[0040] Next, the polyglycerol fatty acid ester (B) used in the present invention can be selected within a range that does not impair the characteristics of the present invention, and is not particularly limited. For example, it is an ester of a polyglycerol having an average degree of polymerization of 2 or more with, for example, citric acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, pentastearic acid, monoisostearic acid, diisostearic acid, pentaisostearic acid, and pentaoleic acid, and more specifically, polyglyceryl caprylate, tetraglyceryl monolaurate, tetraglyceryl monostearate, tetraglyceryl monooleate, hexaglyceryl monolaurate, hexaglyceryl monomyristate, hexaglyceryl monopalmitate, hexaglyceryl monostearate, hexaglyceryl monooleate, hexaglyceryl tristearate, isostearic acid, Examples of the polyglycerin fatty acid ester include hexaglyceryl, hexaglyceryl pentastearate, decaglyceryl monocaprylate, decaglyceryl monolaurate, decaglyceryl monomyristate, decaglyceryl monopalmitate, decaglyceryl monostearate, decaglyceryl monooleate, decaglyceryl monolinoleate, glyceryl stearate citrate, tetraglyceryl tristearate, decaglyceryl distearate, decaglyceryl isostearate, decaglyceryl trioleate, decaglyceryl tristearate, decaglyceryl pentastearate, decaglyceryl monoisostearate, decaglyceryl diisostearate, decaglyceryl pentaisostearate, decaglyceryl pentaoleate, etc., and the polyglycerin fatty acid ester may include one or more polyglycerin fatty acid esters selected from the group consisting of these polyglycerin fatty acid esters. Furthermore, commercially available products can be used as these polyglycerin fatty acid esters.

[0041] Furthermore, the polyglycerol fatty acid ester (B) in the emulsion composition according to the present invention preferably has an HLB (Hydrophile-Lipophile Balance) value in the range of 2 to 16.1. Examples of such (B) polyglycerol fatty acid esters include tetraglyceryl monooleate with an HLB value of 2, hexaglyceryl pentastearate with an HLB value of 4, hexaglyceryl tristearate with an HLB value of 7, tetraglyceryl monooleate with an HLB value of 8.8, tetraglyceryl monolaurate with an HLB value of 10, decaglyceryl monooleate with an HLB value of 12, decaglyceryl monolaurate with an HLB value of 14, decaglyceryl monolaurate with an HLB value of 15.5, decaglyceryl monomyristate with an HLB value of 15.7, decaglyceryl monocaprylate with an HLB value of 16.1, polyglyceryl monolaurate with an HLB value of 17.1, glycerol fatty acid esters with an HLB value of 17.3, and polyglyceryl monostearate with an HLB value of 17.5.

[0042] Here, the HLB value refers to a value representing the degree of hydrophilicity and lipophilicity (hydrophobicity) of an emulsifier, and is also referred to as the hydrophilic-lipophilic balance. Regarding the HLB value, if the components used are commercially available, the commercially available product is used, and if the HLB value of the commercially available product is clearly indicated in a document such as a catalog of the commercially available product, the value indicated in the document is used. However, if the components used are not commercially available, or if the HLB value is not clearly indicated in a document such as a catalog, the value calculated by Griffin's formula is used as the HLB value in this specification. In Griffin's formula, the HLB value is calculated using the value of S (the saponification value of the ester) and the value of N (the neutralization value of the fatty acid constituting the ester). The formula is as follows:

[0043] HLB value = 20 (1 - S / N)

[0044] The closer the HLB value is to 20, the greater the hydrophilicity, and the closer it is to 0, the greater the lipophilicity (hydrophobicity). Furthermore, emulsifiers are generally defined as lipophilic (hydrophobic) when their HLB value is less than 7, and as hydrophilic when their HLB value is 7 or greater.

[0045] The weighted average HLB value refers to the average HLB value relative to the total amount of emulsifiers contained in the emulsion composition, and is calculated by the following formula.

[0046] HLB weighted average value = {HLB value of phospholipid × weight (wt%) of phospholipid + HLB value of polyglycerol fatty acid ester × weight (wt%) of polyglycerol fatty acid ester + HLB value of sucrose fatty acid ester × weight (wt%) of sucrose fatty acid ester} / {weight (wt%) of phospholipid + weight (wt%) of polyglycerol fatty acid ester + weight (wt%) of sucrose fatty acid ester}

[0047] The weighted average HLB value of the emulsion composition of the present invention is 10 to 20, preferably 10 to 18, more preferably 10.5 to 17, and even more preferably 10.55 to 16.22, in the case of an emulsion composition containing components (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (C) a phospholipid; it is 10 to 20, preferably 10 to 18, more preferably 10.5 to 17.5, and even more preferably 10.95 to 17.41, in the case of an emulsion composition containing components (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, (C) a phospholipid, and (D) a sucrose fatty acid ester; and it is 10 to 20, preferably 10 to 18, more preferably 10.5 to 17, and even more preferably 10.95 to 16.22, in the case of an emulsion composition containing components (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, (C) a phospholipid, and (D) a sucrose fatty acid ester.

[0048] The weight ratio of the amounts of (A) β-caryophyllene and (B) polyglycerol fatty acid ester according to the present invention can be appropriately set within a range that does not impair the characteristics of the present invention, and is not particularly limited, but can be set, for example, within a range of 100:3 to 1:2. Specifically, the ratio is preferably 3 to 200 parts by weight, more preferably 3 to 180 parts by weight, more preferably 5 to 150 parts by weight, even more preferably 5 to 130 parts by weight, still more preferably 20 to 100 parts by weight, and particularly preferably 20 to 80 parts by weight, per 100 parts by weight of β-caryophyllene.

[0049] The content of the polyglycerol fatty acid ester (B) in the emulsion composition according to the present invention is preferably 1 to 20 parts by weight, more preferably 1.5 to 18 parts by weight, more preferably 1.5 to 15 parts by weight, even more preferably 2 to 15 parts by weight, still more preferably 2 to 13 parts by weight, and particularly preferably 2 to 10 parts by weight, relative to 100 parts by weight of the emulsion composition.

[0050] Next, the phospholipid (C) used in the present invention can be selected within a range that does not impair the characteristics of the present invention, and is not particularly limited. Examples include glycerophospholipids such as phosphatidic acid, bisphosphatidic acid, lecithin (phosphatidylcholine), phosphatidylethanolamine, phosphatidylmethylethanolamine, phosphatidylserine, phosphatidylinositol, phosphatidylglycerin, and diphosphatidylglycerin (cardiolipin), as well as hydrogenated or hydroxylated versions of these; lysolecithin (lysophosphatidylcholine), lysophosphatidic acid, lysophosphatidylglycerin, and glycerophospholipids such as le ... Examples of lyso compounds include phatidylglycerin, lysophosphatidylinositol, lysophosphatidylethanolamine, lysophosphatidylmethylethanolamine, lysophosphatidylcholine (lysolecithin), lysophosphatidylserine, etc.; various lecithins derived from plants such as soybean, corn, peanut, rapeseed, wheat, etc., from animals such as egg yolk, cow, etc., and from microorganisms such as Escherichia coli, etc.; sphingophospholipids such as sphingomyelin, etc., and can include one or more phospholipids selected from the group consisting of these phospholipids, but preferably lecithin or lysolecithin.In addition, these phospholipids can be commercially available products.

[0051] The phospholipid (C) in the emulsion composition according to the present invention preferably has an HLB value of 4 or more, and more preferably has an HLB value in the range of 4 to 13. Examples of such phospholipid (C) include lecithin with an HLB value of 4, lecithin with an HLB value of 6, lecithin with an HLB value of 8, lysolecithin with an HLB value of 8, and lysolecithin with an HLB value of 13.

[0052] The weight ratio of the amounts of (A) β-caryophyllene and (C) phospholipids according to the present invention can be appropriately set within a range that does not impair the characteristics of the present invention, and is not particularly limited, but can be set within a range of, for example, 200:1 to 1:1. Specifically, the ratio is preferably 0.5 to 100 parts by weight, more preferably 0.5 to 80 parts by weight, even more preferably 1 to 80 parts by weight, still more preferably 1 to 50 parts by weight, and particularly preferably 1 to 30 parts by weight, per 100 parts by weight of β-caryophyllene.

[0053] The content of the (C) phospholipid in the emulsion composition according to the present invention is preferably 0.1 to 10 parts by weight, more preferably 0.1 to 8 parts by weight, more preferably 0.1 to 7 parts by weight, more preferably 0.2 to 7 parts by weight, even more preferably 0.2 to 6 parts by weight, still more preferably 0.3 to 6 parts by weight, and particularly preferably 0.3 to 5 parts by weight, relative to 100 parts by weight of the emulsion composition.

[0054] Next, when the emulsion composition according to the present invention contains (D) a sucrose fatty acid ester, the (D) sucrose fatty acid ester can be selected within a range that does not impair the characteristics of the present invention and is not particularly limited, but is preferably one that has high hydrophilicity and excellent water dispersibility, and examples thereof include those in which a fatty acid having 6 to 22 carbon atoms is ester-bonded to one or more hydroxyl groups of sucrose, and specific examples thereof include sucrose laurate, sucrose myristate, sucrose palmitate, sucrose stearate, and sucrose oleate.

[0033] Preferred are sucrose monolaurate, sucrose monomyristate, sucrose monopalmitate, sucrose monostearate, sucrose monooleate, sucrose dilaurate, sucrose dimyristate, sucrose dipalmitate, sucrose distearate, and sucrose dioleate, more preferred are sucrose monolaurate, sucrose monomyristate, sucrose monopalmitate, sucrose monostearate, and sucrose monooleate, and even more preferred are sucrose monolaurate, sucrose monomyristate, and sucrose monostearate. One or more sucrose fatty acid esters selected from the group consisting of these sucrose fatty acid esters may also be included, and commercially available products may be used as these sucrose fatty acid esters.

[0055] The sucrose fatty acid ester (D) in the emulsion composition according to the present invention preferably has an HLB value in the range of 2 to 19. Examples of such sucrose fatty acid ester (D) include sucrose monostearate with an HLB value of 2, sucrose monostearate with an HLB value of 7, sucrose monostearate with an HLB value of 9, sucrose monostearate with an HLB value of 11, sucrose monostearate with an HLB value of 15, sucrose monomyristate with an HLB value of 17, sucrose monolaurate with an HLB value of 18, and sucrose monostearate with an HLB value of 19.

[0056] When the emulsion composition according to the present invention contains a sucrose fatty acid ester (D), the weight ratio of the amounts of (A) β-caryophyllene and (D) sucrose fatty acid ester can be appropriately set within a range that does not impair the characteristics of the present invention and is not particularly limited, but can be set, for example, within a range of 200:1 to 1:2. Specifically, the weight ratio is preferably 0.5 to 200 parts by weight, more preferably 0.8 to 180 parts by weight, more preferably 1 to 150 parts by weight, more preferably 1 to 130 parts by weight, even more preferably 1.5 to 100 parts by weight, still more preferably 1.5 to 80 parts by weight, and particularly preferably 2 to 80 parts by weight, per 100 parts by weight of β-caryophyllene.

[0057] Furthermore, when the emulsion composition according to the present invention contains (D) a sucrose fatty acid ester, the content of (D) the sucrose fatty acid ester is preferably 0.1 to 20 parts by weight, more preferably 0.1 to 18 parts by weight, more preferably 0.1 to 15 parts by weight, more preferably 0.3 to 15 parts by weight, even more preferably 0.3 to 13 parts by weight, still more preferably 0.5 to 13 parts by weight, and particularly preferably 0.5 to 10 parts by weight, relative to 100 parts by weight of the emulsion composition.

[0058] Next, when the emulsion composition according to the present invention contains water, the water is not particularly limited as long as it is used in foods, pharmaceuticals, and cosmetics, and for example, purified water, pure water, ion-exchanged water, alkaline ionized water, deep sea water, vibration water, natural water, etc. can be used.

[0059] When the emulsion composition according to the present invention contains water, the content of water is preferably 0 to 50 parts by weight, more preferably 0 to 45 parts by weight, more preferably 5 to 40 parts by weight, more preferably 10 to 40 parts by weight, even more preferably 15 to 40 parts by weight, still more preferably 15 to 35 parts by weight, and particularly preferably 20 to 35 parts by weight, relative to 100 parts by weight of the emulsion composition.

[0060] Next, the emulsion composition according to the present invention may contain alcohols. Such alcohols can be selected within a range that does not impair the characteristics of the present invention and are not particularly limited, but examples thereof include lower alcohols, polyhydric alcohols, sugar alcohols, etc. More specifically, examples of monohydric alcohols include methanol, ethanol, propanol, isopropanol, isobutyl alcohol, t-butyl alcohol, etc.; examples of dihydric alcohols include ethylene glycol, propylene glycol, trimethylene glycol, 3-methyl-1,3-butanediol, isoprene glycol, 1,2-butylene glycol, etc. glycol, 1,3-butylene glycol, tetramethylene glycol, 2,3-butylene glycol, 1,2-pentanediol, 1,2-hexanediol, pentamethylene glycol, 2-butene-1,4-diol, hexylene glycol, octylene glycol, etc.; trihydric alcohols such as glycerin and trimethylolpropane; tetrahydric alcohols such as pentaerythritol, e.g., 1,2,6-hexanetriol; pentahydric alcohols such as xylitol; hexahydric alcohols such as sorbitol, mannitol, etc.; polyhydric alcohol polymers such as diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, dipropylene glycol, polypropylene glycol, diglycerin, triglycerin, tetraglycerin, and polyglycerin; sugar alcohols such as glucose, sucrose, fructose, maltose, xylitose, maltitol, lactitol, palatinite, erythritol, xylose, lactose, mannose, galactose, inositol, maltotriose, sorbitan, trehalose, reduced starch syrup, starch hydrolyzed sugars, and starch hydrolyzed sugar reduced alcohols can be mentioned. One or more alcohols selected from the group consisting of these alcohols can be included, but those that increase the uniformity of the emulsifier are preferred. Specifically, monohydric alcohols such as methanol and ethanol, dihydric alcohols such as ethylene glycol and propylene glycol, trihydric alcohols such as glycerin, and sugar alcohols such as xylitol, sorbitol, lactitol, and erythritol are more preferred.

[0061] The content of the alcohols in the emulsion composition according to the present invention can be appropriately set within a range that does not impair the characteristics of the present invention, and is not particularly limited. However, the content is preferably 0.1 to 800 parts by weight, more preferably 0.1 to 750 parts by weight, and even more preferably 0.1 to 700 parts by weight, relative to 100 parts by weight of β-caryophyllene.

[0062] Next, the emulsion composition according to the present invention may further contain an antioxidant. Such antioxidants can be selected within a range that does not impair the characteristics of the present invention, and are not particularly limited. Examples of antioxidants include ascorbic acid or ascorbic acid derivatives or salts thereof, such as L-ascorbic acid, sodium L-ascorbate, potassium L-ascorbate, calcium L-ascorbate, L-ascorbic acid phosphate, magnesium L-ascorbic acid phosphate, L-ascorbic acid sulfate, disodium L-ascorbic acid sulfate, and L-ascorbic acid 2-glucoside; tocopherols, such as tocopherol and tocotrienol; flavonoids (catechin, anthocyanin, flavones, isoflavones, flavans, flavanones, rutin, glycosides thereof, etc.); phenolic acids ( Examples of antioxidants include polyphenols such as chlorogenic acid, ellagic acid, gallic acid, propyl gallate, butyl gallate, octyl gallate, dodecyl gallate, BHT (butylhydroxytoluene), BHA (butylhydroxyanisole), tert-butylhydroquinone (TBHQ), etc.), lignans, curcumins, and coumarins; erythorbic acid or erythorbic acid derivatives or salts thereof such as erythorbic acid, sodium erythorbate, potassium erythorbate, calcium erythorbate, erythorbic acid phosphate, and erythorbic acid sulfate; ubiquinone, glutathione, lipoic acid, uric acid, urobilinogen, and bilirubin, which may be used alone or in combination. Preferred antioxidants include tocopherols.

[0063] Furthermore, when the emulsion composition according to the present invention contains an antioxidant, the weight ratio of the blend amounts of (A) β-caryophyllene to the antioxidant can be appropriately set within a range that does not impair the characteristics of the present invention and is not particularly limited, and is set, for example, in the range of 1000:1 to 10:1. Specifically, the weight ratio is preferably 0.1 to 10 parts by weight, more preferably 0.1 to 8 parts by weight, even more preferably 0.1 to 7 parts by weight, still more preferably 0.1 to 6 parts by weight, and particularly preferably 0.1 to 5 parts by weight, per 100 parts by weight of β-caryophyllene.

[0064] Next, the emulsion composition according to the present invention may contain fats and oils as fat-soluble components. Such fats and oils can be selected within a range that does not impair the characteristics of the present invention, and are not particularly limited, but include fats and oils that are liquid at room temperature, solid fats and oils, and mixtures thereof. Examples of liquid fats and oils include olive oil, camellia oil, macadamia nut oil, castor oil, avocado oil, evening primrose oil, turtle oil, corn oil, mink oil, rapeseed oil, egg yolk oil, sesame oil, persic oil, wheat germ oil, camellia oil, linseed oil, sunflower oil, cottonseed oil, perilla oil, soybean oil, peanut oil, tea seed oil, kaya oil, rice bran oil, Chinese ginger oil, Japanese tung oil, jojoba oil, germ oil, glycerin trioctanoate, glycerin triisopalmiate, salad oil, safflower oil, and the like. Examples of the solid fats and oils include beef tallow, hardened beef tallow, beef leg fat, beef bone fat, mink oil, egg yolk oil, lard, horse fat, mutton tallow, hardened oil, cacao butter, coconut oil, hardened coconut oil, palm oil, hardened palm oil, Japan wax, Japan wax kernel oil, and hardened castor oil, and the oil composition may contain one or more fats and oils selected from the group consisting of these fats and oils.

[0065] As the fat or oil, medium-chain fatty acid triglycerides are preferably used. Medium-chain fatty acid glycerides are lipids formed by esterifying glycerol with saturated fatty acids having 6 to 12 carbon atoms, specifically caproic acid, caprylic acid, capric acid, or lauric acid. The number of fatty acids esterified with glycerol may be one to three, or a mixture thereof. Specifically, monoglycerides, diglycerides, triglycerides, or mixtures thereof may be used. Oils rich in unsaturated fatty acids (e.g., olive oil and safflower oil) are liquid at room temperature, while oils rich in saturated fatty acids (e.g., coconut oil and palm oil) are solid. Since medium-chain fatty acid glycerides are contained in, for example, palm oil and coconut oil, these are also suitable for use.

[0066] Furthermore, the emulsion composition according to the present invention may contain any substance as long as it does not impair the characteristics of the present invention. For example, it may contain minerals such as calcium, magnesium, phosphorus, zinc, etc., vitamins such as vitamin B1, vitamin B2, vitamin V12, vitamin C, etc., radical scavengers, various flavorings, sweeteners, acidulants, coloring agents, etc., and these may be used alone or in combination of two or more types.

[0067] Next, the emulsion composition according to the present invention is preferably a pharmaceutical composition or a food or drink composition.

[0068] The pharmaceutical composition may be prepared in a conventional dosage form, for example, by a method appropriately selectable by a person skilled in the art, such as oral preparations including solutions, tablets, capsules, granules, fine granules, powders, chewable preparations, suspensions, emulsions, syrups, elixirs, solid oral preparations, and liquid oral preparations, as well as parenteral preparations including injections, topical preparations, suppositories, inhalants, nasal preparations, and transdermal preparations, with oral preparations being preferred. The above-mentioned preparations can be prepared by conventional methods using the emulsion composition of the present invention and other pharmaceutically acceptable ingredients such as excipients.

[0069] The food and beverage composition can be prepared, for example, by a method appropriately selected by a person skilled in the art, into foods and beverages such as supplements, solid foods, liquid foods, beverages, etc., and can also be ingested as special purpose foods such as foods for specified health uses (FOSHU), functional foods, foods with nutrient function claims, infant formula, infant formula, foods such as powdered milk for young children, foods such as powdered milk for nursing mothers, foods with health claims, foods for the sick, dairy products, fermented milk, etc. Furthermore, the composition can be incorporated into various foods and beverages, regardless of their form, such as liquid, paste, powder, solid, tablet, or capsule, and can be ingested as a food or beverage. When the emulsion composition of the present invention is formulated into an acidic agent or food or beverage, the pH can be set to 2.0 to 6.0, preferably 3.0 to 5.0.

[0070] Next, the method (1) for producing an emulsion composition according to the present invention includes the steps of (i) preparing an oil phase using β-caryophyllene, a polyglycerol fatty acid ester, and a phospholipid (oil phase preparation step), and (ii) emulsifying the prepared oil phase, or mixing the prepared oil phase with a separately prepared aqueous phase and emulsifying the mixture (emulsification step).

[0071] The "separately prepared aqueous phase" in the emulsification step (ii) may be an aqueous phase prepared using water and / or a sucrose fatty acid ester.

[0072] The method (2) for producing an emulsion composition according to the present invention includes the steps of (iii) preparing an oil phase using β-caryophyllene and a polyglycerol fatty acid ester (oil phase preparation step), (iv) preparing an aqueous phase using a sucrose fatty acid ester (aqueous phase preparation step), (v) mixing the prepared oil phase and aqueous phase (mixing step), and (vi) emulsifying the mixed oil phase and aqueous phase (emulsification step).

[0073] In the aqueous phase preparation step (iv), a sucrose fatty acid ester may be used, and it is optional whether or not water is used.

[0074] The above-mentioned oil phase preparation steps (i) and (iii), aqueous phase preparation step (iv), mixing step (v), and emulsification steps (ii) and (vi) can all be carried out by methods that can be appropriately selected by those skilled in the art.

[0075] The temperature in the above steps (i) to (vi) may be set appropriately depending on the thermal stability, viscosity, solubility, and mixability of the fat-soluble component, and may be any temperature in the range of room temperature to 80° C. Furthermore, a conventional mixer or emulsifier may be used as the mixer or emulsifier used in the mixing step (v) and the emulsification steps (ii) and (vi). Examples of such a mixer or emulsifier include a conventional stirrer, homomixer, continuous flow shearing device, high-pressure homogenizer, and ultrasonic disperser. However, when it is desired to set the emulsion diameter of the fat-soluble component to 300 nm, particularly 150 nm, and to impart higher transparency, permeability, and the like to the emulsion composition, a strong stirrer such as a high-pressure homogenizer can be used.

[0076] Next, the method (1) for stabilizing β-caryophyllene contained in the emulsion composition of the present invention includes (vii) a step of blending β-caryophyllene, a polyglycerol fatty acid ester, and a phospholipid into an oil phase (oil phase blending step).

[0077] Furthermore, the method (2) for stabilizing β-caryophyllene contained in the emulsion composition according to the present invention includes the steps of (viii) blending β-caryophyllene and a polyglycerol fatty acid ester into an oil phase (oil phase blending step), and (ix) blending a sucrose fatty acid ester into an aqueous phase (aqueous phase blending step).

[0078] In the oil phase blending step (viii) of the method (2) for stabilizing β-caryophyllene contained in the emulsion composition according to the present invention, a phospholipid can be blended into the oil phase.

[0079] The oil phase blending steps (vii) and (viii) and the aqueous phase blending step (ix) can all be carried out by a method that can be appropriately selected by a person skilled in the art.

[0080] The method (1) for producing an emulsion composition according to the present invention may include not only the oil phase preparation step (i) and the emulsification step (ii) but also other steps as long as the characteristics of the present invention are not impaired. The method (2) for producing an emulsion composition according to the present invention may include not only the oil phase preparation step (iii), the aqueous phase preparation step (iv), the mixing step (v), and the emulsification step (vi) but also other steps as long as the characteristics of the present invention are not impaired. The method (1) for stabilizing β-caryophyllene contained in an emulsion composition according to the present invention may include not only the oil phase blending step (vii) but also other steps as long as the characteristics of the present invention are not impaired. The method (2) for stabilizing β-caryophyllene contained in an emulsion composition according to the present invention may include not only the oil phase blending step (viii) and the aqueous phase blending step (ix) but also other steps as long as the characteristics of the present invention are not impaired.

[0081] In the following examples, the present invention will be described in more detail using test examples, but the technical scope of the present invention is not limited to the following examples.

[0082] 1. Preparation of emulsion compositions First, Test Examples 1 to 38 were prepared as follows using the components shown in Table 1 below. The decaglyceryl monolaurate and sucrose monostearate used in the following Test Examples were commercially available products. Furthermore, a commercially available high-pressure homogenizer was used for high-pressure emulsification in the following Test Examples.

[0083]

[0084] [1-1] Preparation of Test Example 1 3.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, and 2.0 g of lecithin having an HLB value of 4 were added to 48.8 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 1. The weighted average HLB value was 15.32.

[0085] [1-2] Preparation of Test Example 2 3.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 2. The weighted average HLB value was 15.32.

[0086] [1-3] Preparation of Test Example 3 3.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 6 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 3. The weighted average HLB value was 15.68.

[0087] [1-4] Preparation of Test Example 4 3.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 8 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 4. The weighted average HLB value was 16.05.

[0088] [1-5] Preparation of Test Example 5 4.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 47.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 5. The weighted average HLB value was 15.33.

[0089] [1-6] Preparation of Test Example 6 4.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 34.0 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 25.0 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 6. The weighted average HLB value was 15.33.

[0090] [1-7] Preparation of Test Example 7 4.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 50.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 3.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 7. The weighted average HLB value was 14.11.

[0091] [1-8] Preparation of Test Example 8 4.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 0.5 g of lecithin having an HLB value of 4 were added to 51.8 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 3.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 8. The weighted average HLB value was 16.13.

[0092] [1-9] Preparation of Test Example 9 7.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 0.5 g of lecithin having an HLB value of 4 were added to 61.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 4.0 g of sucrose monostearate having an HLB value of 19 was added to 15.0 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 9. The weighted average HLB value was 16.22.

[0093] [1-10] Preparation of Test Example 10 4.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 51.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 2.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 10. The weighted average HLB value was 13.50.

[0094] [1-11] Preparation of Test Example 11 5.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 1.5 g of lecithin having an HLB value of 4 were added to 46.8 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 11. The weighted average HLB value was 15.80.

[0095] [1-12] Preparation of Test Example 12 5.0 g of decaglyceryl monolaurate (with an HLB value of 15.5), 11.7 g of β-caryophyllene, and 0.5 g of mixed tocopherols were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate (with an HLB value of 19) was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 12. The weighted average HLB value was 17.41.

[0096] [1-13] Preparation of Test Example 13 4.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 47.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 15 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 13. The weighted average HLB value was 13.33.

[0097] [1-14] Preparation of Test Example 14 3.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 11 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 14. The weighted average HLB value was 10.95.

[0098] [1-15] Preparation of Test Example 15 4.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 47.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monolaurate having an HLB value of 18 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 15. The weighted average HLB value was 14.83.

[0099] [1-16] Preparation of Test Example 16 4.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 47.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monomyristate having an HLB value of 17 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 16. The weighted average HLB value was 14.33.

[0100] [1-17] Preparation of emulsion composition according to Test Example 17 5.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 1.5 g of lecithin having an HLB value of 4 were added to 46.8 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monomyristate having an HLB value of 17 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 17. The weighted average HLB value was 14.84.

[0101] [1-18] Preparation of Test Example 18 4.0 g of decaglyceryl monolaurate having an HLB value of 14, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 47.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 18. The weighted average HLB value was 14.83.

[0102] [1-19] Preparation of Test Example 19 4.0 g of decaglyceryl monomyristate having an HLB value of 15.7, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 47.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 19. The weighted average HLB value was 15.40.

[0103] [1-20] Preparation of Test Example 20 4.0 g of decaglyceryl monocaprylate with an HLB value of 16.1, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin with an HLB value of 4 were added to 50.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 3.0 g of sucrose monostearate with an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 20. The weighted average HLB value was 14.38.

[0104] [1-21] Preparation of Test Example 21 3.0 g of decaglyceryl monocaprylate with an HLB value of 16.1, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin with an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate with an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 21. The weighted average HLB value was 15.48.

[0105] [1-22] Preparation of Test Example 22 4.0 g of decaglyceryl monooleate having an HLB value of 12, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 47.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 22. The weighted average HLB value was 14.17.

[0106] [1-23] Preparation of Test Example 23 3.0 g of tetraglyceryl monolaurate having an HLB value of 10, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 23. The weighted average HLB value was 13.82.

[0107] [1-24] Preparation of Test Example 24 3.0 g of tetraglyceryl monooleate having an HLB value of 8.8, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 24. The weighted average HLB value was 13.49.

[0108] [1-25] Preparation of Test Example 25 3.0 g of tetraglyceryl monooleate having an HLB value of 2, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 25. The weighted average HLB value was 11.64.

[0109] [1-26] Preparation of Test Example 26 3.0 g of hexaglyceryl tristearate having an HLB value of 7, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 26. The weighted average HLB value was 13.00.

[0110] [1-27] Preparation of Test Example 27 3.0 g of hexaglyceryl pentastearate having an HLB value of 4, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 6.0 g of sucrose monostearate having an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 27. The weighted average HLB value was 12.18.

[0111] [1-28] Preparation of Test Example 28 9.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. The oil phase and 28.5 g of water were mixed, and high-pressure emulsified using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 28. The weighted average HLB value was 13.41.

[0112] [1-29] Preparation of Test Example 29 9.0 g of decaglyceryl monolaurate having an HLB value of 14, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 48.3 g of glycerin, mixed, and dissolved to prepare an oil phase. The oil phase and 28.5 g of water were mixed, and high-pressure emulsified using a high-pressure homogenizer to obtain an emulsion composition, designated Test Example 29. The weighted average HLB value was 12.18.

[0113] [1-30] Preparation of Test Example 30 9.0 g of decaglyceryl monomyristate having an HLB value of 15.7, 11.7 g of β-caryophyllene, and 2.0 g of lecithin having an HLB value of 4 were added to 48.8 g of glycerin, mixed, and dissolved to prepare an oil phase. The oil phase and 28.5 g of water were mixed, and high-pressure emulsification was performed using a high-pressure homogenizer to obtain an emulsion composition, which was designated Test Example 30. The weighted average HLB value was 13.57.

[0114] [1-31] ​​Preparation of Test Example 31 9.0 g of decaglyceryl monooleate having an HLB value of 12, 17.2 g of β-caryophyllene, and 2.0 g of lecithin having an HLB value of 4 were added to 43.3 g of glycerin, mixed, and dissolved to prepare an oil phase. The oil phase and 28.5 g of water were mixed, and high-pressure emulsified using a high-pressure homogenizer to obtain an emulsion composition designated as Test Example 31. The weighted average HLB value was 10.55.

[0115] [1-32] Preparation of Test Example 32 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 5.0 g of lecithin with an HLB value of 4 were added to 46.3 g of glycerin, mixed, and dissolved to prepare an oil phase. Subsequently, 8.0 g of sucrose monostearate with an HLB value of 19 was added to 28.5 g of water to prepare an aqueous phase, and the oil phase and aqueous phase were mixed and subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated Test Example 32. The weighted average HLB value was 13.23.

[0116] [1-33] Preparation of Test Example 33 9.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 1.0 g of lecithin having an HLB value of 4 were added to 76.8 g of glycerin, mixed, and dissolved to prepare an oil phase. This oil phase was mixed with 1.0 g of sucrose monostearate having an HLB value of 19, and the mixture was subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated as Test Example 33. The weighted average HLB value was 14.77.

[0117] [1-34] Preparation of Test Example 34 9.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 1.0 g of lecithin having an HLB value of 4 were added to 76.8 g of glycerin, mixed, and dissolved to prepare an oil phase. This oil phase was mixed with 1.0 g of sucrose monostearate having an HLB value of 9, and the mixture was subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated as Test Example 34. The weighted average HLB value was 13.86.

[0118] [1-35] Preparation of Test Example 35 9.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 1.0 g of lecithin having an HLB value of 4 were added to 76.8 g of glycerin, mixed, and dissolved to prepare an oil phase. This oil phase was mixed with 1.0 g of sucrose monostearate having an HLB value of 7, and the mixture was subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated as Test Example 35. The weighted average HLB value was 13.68.

[0119] [1-36] Preparation of Test Example 36 9.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 1.0 g of lecithin having an HLB value of 4 were added to 76.8 g of glycerin, mixed, and dissolved to prepare an oil phase. This oil phase was mixed with 1.0 g of sucrose monostearate having an HLB value of 2, and the mixture was subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition designated as Test Example 36. The weighted average HLB value was 13.23.

[0120] [1-37] Preparation of Test Example 37 9.0 g of decaglyceryl monolaurate having an HLB value of 15.5, 11.7 g of β-caryophyllene, 0.5 g of mixed tocopherols, and 2.0 g of lecithin having an HLB value of 4 were added to 76.8 g of glycerin, mixed, and dissolved to prepare an oil phase. The oil phase was subjected to high-pressure emulsification using a high-pressure homogenizer to obtain an emulsion composition, which was designated Test Example 37. The weighted average HLB value was 13.41.

[0121] [1-38] Preparation of Test Example 38 β-caryophyllene was used as Test Example 38.

[0122] The formulations and weighted average HLB values ​​of Test Examples 1 to 38 are shown in Tables 2 to 6 below.

[0123]

[0124]

[0125]

[0126]

[0127]

[0128] As shown in Tables 1 to 6, the weighted average HLB values ​​of emulsion compositions containing (A) β-caryophyllene, (B) polyglycerol fatty acid ester, and (C) phospholipid were 10.55 to 16.22, the weighted average HLB values ​​of emulsion compositions containing (A) β-caryophyllene, (B) polyglycerol fatty acid ester, and (D) sucrose fatty acid ester were 10.95 to 17.41, and the weighted average HLB values ​​of emulsion compositions containing (A) β-caryophyllene, (B) polyglycerol fatty acid ester, (C) phospholipid, and (D) sucrose fatty acid ester were 10.95 to 16.22.

[0129] 2. Evaluation of the Effect of Oxidation of β-Caryophyllene Contained in the Emulsion Composition on the Fragrance As described above, β-caryophyllene is an aroma component, but due to the double bond contained in the molecule, it is easily oxidized, resulting in a deterioration in the fragrance. Therefore, the effect of oxidation on the fragrance of Test Examples 1 to 38 was evaluated by sensory testing.

[0130] 10 mL of each of Test Examples 1 to 38 was placed in a 20 mL sample bottle, which was then filled with sufficient oxygen gas to replace any voids with oxygen gas and sealed. The 38 sample bottles were stored in a constant temperature bath at 60°C for 7 days, after which a sensory evaluation was conducted by 13 people of all ages and genders. The sensory evaluation was conducted on "(1) fragrance strength" and "(2) changes in fragrance."

[0131] Regarding "(1) fragrance strength," five samples were prepared for each of Test Examples 1 to 38, one immediately after preparation and one after storage in a 60°C thermostatic chamber for seven days (expired product), and the fragrance strength of the expiring product compared to the immediately prepared product was evaluated on a scale of 10 (0 points (very weak) to 10 points (very strong)). Meanwhile, regarding "(2) change in fragrance," the degree of change in fragrance of the expiring product compared to the immediately prepared product was evaluated on a scale of 5 (0 points (no change) to 5 points (very great change)). The results are shown in Table 7.

[0132]

[0133] The characteristics of each Test Example are summarized as follows: (i) Emulsion compositions prepared from an oil phase and an aqueous phase, wherein the oil phase is prepared from β-caryophyllene, mixed tocopherols, lecithin, a polyglycerol fatty acid ester, and glycerin, and the aqueous phase is prepared from a sucrose fatty acid ester and water: Test Example 2, Test Example 3, Test Example 4, Test Example 5, Test Example 6, Test Example 7, Test Example 8, Test Example 9, Test Example 10, Test Example 11, Test Example 13, Test Example 14, Test Example 15, Test Example 16, Test Example 17, Test Example 18, Test Example 19, Test Example 20, Test Example 21, Test Example 22, Test Example 23, Test Example 24, Test Example 25, Test Example 26, and Test Example 27.

[0134] (ii) An emulsified composition prepared from an oil phase and an aqueous phase, wherein the oil phase is prepared from β-caryophyllene, lecithin, a polyglycerol fatty acid ester, and glycerin, and the aqueous phase is prepared from a sucrose fatty acid ester and water: Test Example 1.

[0135] (iii) An emulsified composition prepared from an oil phase and an aqueous phase, wherein the oil phase is prepared from β-caryophyllene, mixed tocopherols, a polyglycerol fatty acid ester, and glycerin, and the aqueous phase is prepared from a sucrose fatty acid ester and water: Test Example 12.

[0136] (iv) An emulsion composition prepared from an oil phase and water, wherein the oil phase is prepared from β-caryophyllene, mixed tocopherols, lecithin, a polyglycerol fatty acid ester, and glycerin: Test Example 28 and Test Example 29.

[0137] (v) An emulsified composition prepared from an oil phase and water, wherein the oil phase is prepared from β-caryophyllene, lecithin, a polyglycerol fatty acid ester, and glycerin: Test Example 30 and Test Example 31.

[0138] (vi) An emulsified composition prepared from an oil phase and an aqueous phase, wherein the oil phase is prepared from β-caryophyllene, mixed tocopherols, lecithin, and glycerin, and the aqueous phase is prepared from a sucrose fatty acid ester and water: Test Example 32.

[0139] (vii) An emulsion composition prepared from an oil phase and a sucrose fatty acid ester, wherein the oil phase is prepared from β-caryophyllene, mixed tocopherols, lecithin, a polyglycerol fatty acid ester, and glycerin: Test Example 33, Test Example 34, Test Example 35, and Test Example 36.

[0140] (viii) An emulsified composition prepared from an oil phase, wherein the oil phase was prepared from β-caryophyllene, mixed tocopherols, lecithin, polyglycerol fatty acid ester, and glycerin: Test Example 37.

[0141] (ix) β-caryophyllene only: Test Example 38.

[0142] As a result of the sensory evaluation of "(1) fragrance strength" and "(2) fragrance change," as shown in Table 7, Test Examples 1 to 31 and Test Examples 33 to 37, which contained a polyglycerol fatty acid ester during the preparation of the emulsion composition, were rated "good," i.e., the fragrance did not deteriorate. Therefore, it was revealed that an emulsion composition containing (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (C) a phospholipid; an emulsion composition containing (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (D) a sucrose fatty acid ester; and an emulsion composition containing (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, (C) a phospholipid, and (D) a sucrose fatty acid ester have the effect of suppressing deterioration of the fragrance of the β-caryophyllene contained therein. From this, it can be said that an emulsion composition containing (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (C) a phospholipid; an emulsion composition containing (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (D) a sucrose fatty acid ester; and an emulsion composition containing (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, (C) a phospholipid, and (D) a sucrose fatty acid ester have the effect of stabilizing the (A) β-caryophyllene they contain.

[0143] 3. Conversion of β-caryophyllene contained in emulsion compositions to oxides (headspace analysis) For Test Examples 1, 5, 8, 19, 28, and 38, the conversion of β-caryophyllene to oxides when oxygen was added and the compositions were allowed to stand for a certain period of time was evaluated by quantifying the oxides using headspace analysis using gas chromatography.

[0144] Ten mL of each of Test Examples 1, 5, 8, 19, 28, and 38 was placed in a 20 mL sample bottle, which was then filled with sufficient oxygen gas to replace the voids with oxygen gas and sealed. The six sample bottles were stored in a constant temperature bath at 60°C for 7 days, after which the amount of caryophyllene oxide was quantified by headspace analysis using gas chromatography. The quantification by headspace analysis using gas chromatography was performed using solid-phase microextraction (SPME). For gas chromatography, an Agilent Technologies 8890 / 5977C and a Gestel MPS robotic pro were used. The results are shown in Table 8.

[0145]

[0146] As a result, as shown in Table 8, it was found that the above-mentioned "3(1) fragrance intensity" and "3(2) change in fragrance" correlate with the transformation to oxides when oxygen is added and left for a certain period of time. This result further supports the idea that an emulsion composition containing (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (C) a phospholipid; an emulsion composition containing (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (D) a sucrose fatty acid ester; and an emulsion composition containing (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, (C) a phospholipid, and (D) a sucrose fatty acid ester have the effect of stabilizing the β-caryophyllene contained therein.

Claims

1. An emulsion composition containing the following components (A), (B) and (C): (A) β-caryophyllene, (B) a polyglycerol fatty acid ester, and (C) a phospholipid.

2. An emulsion composition containing the following components (A), (B) and (D): (A) β-caryophyllene, (B) polyglycerin fatty acid ester, (D) sucrose fatty acid ester.

3. The emulsion composition according to claim 1, containing (D) sucrose fatty acid ester.

4. An emulsion composition described in any one of claims 1 to 3, wherein the HLB value of the polyglycerol fatty acid ester (B) is 2 to 16.

1.

5. An emulsion composition according to claim 2 or 3, wherein the HLB value of the sucrose fatty acid ester (D) is 2 to 19.

6. The emulsion composition according to claim 1, having a weighted average HLB value of 10 to 20.

7. The emulsion composition according to claim 2, wherein the weighted average HLB value is 10 to 20.

8. The emulsion composition according to claim 3, wherein the weighted average HLB value is 10 to 20.

9. An emulsion composition according to any one of claims 1 to 3, wherein the weight ratio of the amounts of (A) β-caryophyllene and (B) polyglycerol fatty acid ester is 3 to 200 parts by weight of (B) polyglycerol fatty acid ester per 100 parts by weight of (A) β-caryophyllene.

10. An emulsion composition according to any one of claims 1 to 3, wherein the content of (B) polyglycerol fatty acid ester in the emulsion composition is 1 to 20 parts by weight per 100 parts by weight of the emulsion composition.

11. An emulsion composition according to claim 1 or 3, wherein the weight ratio of the amounts of (A) β-caryophyllene and (C) phospholipid is 0.5 to 100 parts by weight of (C) phospholipid to 100 parts by weight of (A) β-caryophyllene.

12. An emulsion composition according to claim 1 or 3, wherein the content of the phospholipid (C) in the emulsion composition is 0.1 to 10 parts by weight per 100 parts by weight of the emulsion composition.

13. An emulsion composition according to claim 2 or 3, wherein the weight ratio of the amounts of (A) β-caryophyllene and (D) sucrose fatty acid ester is 0.5 to 200 parts by weight of (D) sucrose fatty acid ester per 100 parts by weight of (A) β-caryophyllene.

14. The emulsion composition according to claim 2 or 3, wherein the content of the sucrose fatty acid ester (D) in the emulsion composition is 0.1 to 20 parts by weight per 100 parts by weight of the emulsion composition.

15. A composition according to any one of claims 1 to 3, containing an antioxidant.

16. An emulsion composition described in any one of claims 1 to 3, which is a pharmaceutical composition or a food or beverage composition.

17. A method for producing an emulsion composition, comprising: preparing an oil phase using β-caryophyllene, a polyglycerol fatty acid ester, and a phospholipid; and emulsifying the oil phase prepared, or mixing and emulsifying the oil phase prepared with a separately prepared aqueous phase.

18. A method for producing an emulsion composition, comprising the steps of: preparing an oil phase using β-caryophyllene and a polyglycerol fatty acid ester; preparing an aqueous phase using a sucrose fatty acid ester; mixing the prepared oil phase and aqueous phase; and emulsifying the mixed oil phase and aqueous phase.

19. A method for stabilizing β-caryophyllene contained in an emulsion composition, comprising the step of blending β-caryophyllene, a polyglycerol fatty acid ester, and a phospholipid in an oil phase.

20. A method for stabilizing β-caryophyllene contained in an emulsion composition, comprising the steps of blending β-caryophyllene and a polyglycerin fatty acid ester into an oil phase, and blending a sucrose fatty acid ester into an aqueous phase.

Images