JP2021166478A - O/d emulsifying composition containing terpenoid glycoside - Google Patents
O/d emulsifying composition containing terpenoid glycoside Download PDFInfo
- Publication number
- JP2021166478A JP2021166478A JP2020070272A JP2020070272A JP2021166478A JP 2021166478 A JP2021166478 A JP 2021166478A JP 2020070272 A JP2020070272 A JP 2020070272A JP 2020070272 A JP2020070272 A JP 2020070272A JP 2021166478 A JP2021166478 A JP 2021166478A
- Authority
- JP
- Japan
- Prior art keywords
- terpenoid glycoside
- emulsified composition
- terpenoid
- polyhydric alcohol
- glycoside
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 terpenoid glycoside Chemical class 0.000 title claims abstract description 97
- 239000000203 mixture Substances 0.000 title claims abstract description 92
- 229930182470 glycoside Natural products 0.000 title claims abstract description 77
- 230000001804 emulsifying effect Effects 0.000 title claims abstract description 20
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 34
- 239000004094 surface-active agent Substances 0.000 claims abstract description 28
- 235000013305 food Nutrition 0.000 claims abstract description 26
- 239000007864 aqueous solution Substances 0.000 claims abstract description 12
- 239000000839 emulsion Substances 0.000 claims abstract description 7
- 239000008385 outer phase Substances 0.000 claims abstract 2
- 239000003921 oil Substances 0.000 claims description 30
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 23
- 229930195729 fatty acid Natural products 0.000 claims description 23
- 239000000194 fatty acid Substances 0.000 claims description 23
- 239000012071 phase Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000008157 edible vegetable oil Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000005720 sucrose Substances 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims 1
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- 235000013616 tea Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000000892 thaumatin Substances 0.000 description 1
- 235000010436 thaumatin Nutrition 0.000 description 1
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- 150000003648 triterpenes Chemical class 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
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- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000001717 vitis vinifera seed extract Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
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- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Edible Oils And Fats (AREA)
- Tea And Coffee (AREA)
- Dairy Products (AREA)
Abstract
Description
本発明は、テルペノイド配糖体含有Ｏ／Ｄ乳化組成物及びその製造方法、さらには該テルペノイド配糖体含有Ｏ／Ｄ乳化組成物を含有した飲食品に関する。 The present invention relates to a terpenoid glycoside-containing O / D emulsified composition and a method for producing the same, and further relates to a food or drink containing the terpenoid glycoside-containing O / D emulsified composition.
飲食品において乳化組成物の使用用途は広く、香料、酸化防止剤、機能性素材等を安定的に飲食品へ添加する目的で乳化組成物とすることが知られている。例えば、香料は、飲食品に風味や香味を付与する添加物として使用されており、酸化防止剤は飲食品の風味劣化を防止する添加物として幅広く使用されている。これらは目的に応じて水溶性、油溶性のものが用いられるが、油溶性の香料成分や酸化防止剤成分はそのままでは水系の飲食品への添加が困難であるため、界面活性剤を用いて水中に分散可能な乳化組成物として調製される。
分子構造に親水基と疎水基を含有する両親媒性の素材は界面活性能力を有すとされている。そして一部の機能性素材も同様の構造を有しており、弱いながらも一定の乳化効果を示すことが知られている。しかしながらその能力は決して強いものではなく単独での乳化安定化は難しい。また自身が界面活性能を有しているため、界面活性剤を共存させての乳化を実施する際、寧ろ不安定化を引き起こし乳化が困難である場合も多い。その一例としてテルペノイド配糖体が挙げられる。テルペノイド配糖体を含有した安定的な乳化組成物を調製した報告は少なく、乳化組成物への配合量に大きく制限が生じているのが実情である。テルペノイド配糖体は有用な機能を有しているものも多く、安定に乳化組成物に配合する調製方法が求められている。
安定な乳化組成物を調製する方法は数多く報告されているが、テルペノイド配糖体を配合したＯ／Ｄ乳化組成物の調製方法は報告されていなかった。
The emulsified composition has a wide range of uses in foods and drinks, and it is known that the emulsified composition is used for the purpose of stably adding flavors, antioxidants, functional materials and the like to foods and drinks. For example, flavors are used as additives that impart flavor and flavor to foods and drinks, and antioxidants are widely used as additives that prevent flavor deterioration of foods and drinks. Water-soluble and oil-soluble materials are used depending on the purpose, but since it is difficult to add oil-soluble flavor components and antioxidant components to water-based foods and drinks as they are, surfactants are used. It is prepared as an emulsified composition that can be dispersed in water.
An amphipathic material containing a hydrophilic group and a hydrophobic group in its molecular structure is said to have surface-active ability. It is known that some functional materials also have a similar structure and show a certain emulsifying effect although they are weak. However, its ability is not strong and it is difficult to stabilize emulsification by itself. In addition, since it has a surface-active ability, when emulsification is carried out in the coexistence of a surfactant, it often causes instability and is difficult to emulsify. One example is a terpenoid glycoside. There are few reports of preparing a stable emulsified composition containing a terpenoid glycoside, and the actual situation is that the amount to be blended in the emulsified composition is greatly limited. Many terpenoid glycosides have useful functions, and a preparation method for stably blending them into an emulsified composition is required.
Although many methods for preparing a stable emulsified composition have been reported, no method for preparing an O / D emulsified composition containing a terpenoid glycoside has been reported.
Ｏ／Ｄ乳化を利用した技術が過去に報告されている（例えば、特許文献１、２参照。）。
しかしながら、単にＯ／Ｄ乳化を実施しているだけでありテルペノイド配糖体を配合した安定的な乳化は達成されていなかった。
さらに、テルペノイドを含有する水中油型エマルションの技術が報告されている（例えば、特許文献３、４参照。）。
しかしながら、何れも水中油型エマルション（Ｏ／Ｗ乳化組成物）であり、本願発明のＯ／Ｄ乳化組成物ではなく、また使用されているのはテルペノイドでありその配糖体ではなかった。
このように、難乳化性物質の乳化組成物調製方法は様々な検討がなされているが、テルペノイド配糖体を含有するＯ／Ｄ乳化組成物に関しては十分な乳化安定性と実用性を有するものはほとんど無く、更なる開発が求められていた。
Techniques using O / D emulsification have been reported in the past (see, for example, Patent Documents 1 and 2).
However, only O / D emulsification was carried out, and stable emulsification containing a terpenoid glycoside was not achieved.
Further, a technique of an oil-in-water emulsion containing a terpenoid has been reported (see, for example, Patent Documents 3 and 4).
However, all of them are oil-in-water emulsions (O / W emulsified compositions), not the O / D emulsified compositions of the present invention, and terpenoids are used, not glycosides thereof.
As described above, various methods for preparing an emulsifying composition of a refractory substance have been studied, but an O / D emulsifying composition containing a terpenoid glycoside has sufficient emulsification stability and practicality. There was almost no such thing, and further development was required.
本発明は前記従来技術に鑑みてなされたものであり、テルペノイド配糖体を含有する乳化組成物の乳化安定性を向上させることを可能とし、さらには飲食品での分散性に優れ、安定に飲食品に添加することのできる乳化組成物の開発を目的としたものである。 The present invention has been made in view of the above-mentioned prior art, and it is possible to improve the emulsification stability of an emulsified composition containing a terpenoid glycoside, and further, it is excellent in dispersibility in foods and drinks and is stable. The purpose is to develop an emulsified composition that can be added to foods and drinks.
本発明者らは、実用的な量のテルペノイド配糖体を含有し、十分な乳化安定性と、飲食品中への分散性に優れる乳化組成物を開発するため鋭意検討した結果、界面活性剤（Ａ）、テルペノイド配糖体（Ｂ）、及び食用油脂（Ｃ）を含有し、乳化組成物中に含有するＡとＢの質量比率が１：３０〜３０：１、かつＢとＣの質量比率が１：１０〜１０：１であるＯ／Ｄ乳化組成物とすることで、さらには、テルペノイド配糖体（Ｂ）と食用油脂（Ｃ）を混合した油相を調製する工程と、この油相を多価アルコール又は多価アルコール水溶液と界面活性剤（Ａ）を含有する水相中に添加して乳化組成物を調製する工程を有する製造方法とすることで、安定的な乳化組成物を得ることが可能となり、飲食品中への分散性にも優れることを見出し、本発明に至ったものである。 As a result of diligent studies to develop an emulsifying composition containing a practical amount of terpenoid glycoside, which has sufficient emulsion stability and excellent dispersibility in foods and drinks, the present inventors have made a surfactant. It contains (A), a terpenoid glycoside (B), and an edible oil (C), and the mass ratio of A and B contained in the emulsified composition is 1:30 to 30: 1, and the mass of B and C. By preparing an O / D emulsified composition having a ratio of 1:10 to 10: 1, a step of preparing an oil phase in which a terpenoid glycoside (B) and an edible oil (C) are mixed, and this step. A stable emulsified composition can be obtained by adding an oil phase to an aqueous phase containing a polyhydric alcohol or an aqueous polyhydric alcohol solution and a surfactant (A) to prepare an emulsified composition. It has been found that the product can be easily dispersed in foods and drinks, and the present invention has been achieved.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物は、従来の乳化組成物と比較して乳化安定性に優れ、さらには飲食品中への分散性に優れるという利点がある。本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物を用いることにより、長期間保存される飲食品中等、経時的な乳化不安定化が懸念される条件下においても安定的に使用することができ、品質の良好なテルペノイド配糖体を含有する飲食品を提供することが可能となる。 The terpenoid glycoside-containing O / D emulsified composition of the present invention has an advantage that it is excellent in emulsification stability as compared with a conventional emulsified composition, and further is excellent in dispersibility in foods and drinks. By using the terpenoid glycoside-containing O / D emulsification composition of the present invention, it can be stably used even under conditions where there is a concern about emulsification instability over time, such as in foods and drinks stored for a long period of time. It is possible to provide foods and drinks containing terpenoid glycosides of good quality.
以下、本発明を詳細に説明する。
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物は、十分な乳化安定性及び飲食品中での分散性を得るために、界面活性剤、テルペノイド配糖体、及び食用油脂を含有し、乳化組成物中に含有する界面活性剤とテルペノイド配糖体の質量比率と、テルペノイド配糖体と食用油脂の質量比率が一定の範囲内であることを特徴とするＯ／Ｄ乳化組成物であることを特徴とする。
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物の調製方法としては種々の方法が知られているが、その中でも、水相への混合時に微細なＯ／Ｗ乳化組成物を得る方法として界面科学的手法を用いたＤ相乳化法が知られている。Ｄ相乳化法とは、界面活性剤を含有する多価アルコール溶液又は多価アルコール水溶液（Ｄ相）に油相を添加して乳化する方法であり、これによってテルペノイド配糖体含有Ｏ／Ｄ乳化組成物が得られる。このＯ／Ｄ乳化組成物を水相に混合することで微細なＯ／Ｗ乳化組成物を得ることができる。
Hereinafter, the present invention will be described in detail.
The terpenoid glycoside-containing O / D emulsification composition of the present invention contains a surfactant, a terpenoid glycoside, and an edible oil / fat in order to obtain sufficient emulsion stability and dispersibility in foods and drinks. The O / D emulsification composition is characterized in that the mass ratio of the surfactant and the terpenoid glycoside contained in the emulsification composition and the mass ratio of the terpenoid glycoside and the edible oil and fat are within a certain range. It is characterized by that.
Various methods are known as methods for preparing the terpenoid glycoside-containing O / D emulsified composition of the present invention, and among them, as a method for obtaining a fine O / W emulsified composition when mixed with an aqueous phase. A D-phase emulsification method using a surface science method is known. The D-phase emulsification method is a method of adding an oil phase to a polyhydric alcohol solution or a polyhydric alcohol aqueous solution (D phase) containing a surfactant to emulsify, thereby emulsifying O / D containing a terpenoid glycoside. The composition is obtained. A fine O / W emulsified composition can be obtained by mixing this O / D emulsified composition with the aqueous phase.
本発明の界面活性剤とは、特に限定されるものではないが、例えば、ポリグリセリン脂肪酸エステル、モノグリセリン脂肪酸エステル、ショ糖脂肪酸エステル、有機酸モノグリセリド（酢酸モノグリセリド、乳酸モノグリセリド、クエン酸モノグリセリド、ジアセチル酒石酸モノグリセリド、コハク酸モノグリセリド）、ポリオキシエチレン誘導体、プロピレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、レシチン（大豆レシチン、菜種レシチン、卵黄レシチン、ひまわりレシチン）、酵素分解レシチン（大豆酵素分解レシチン、菜種酵素分解レシチン、卵黄酵素分解レシチン）等が挙げられ、これらの群より選ばれる１種又は２種以上を併用してもよい。各種の乳化不安定化要因による乳化破壊に対し安定な乳化構造を維持するといった観点から、ポリグリセリン脂肪酸エステルを含有することが望ましく、その他の界面活性剤を１種又は２種以上を併用してもよいが、界面活性剤全量中のポリグリセリン脂肪酸エステル含有割合は、好ましくは５０質量％以上の割合であり、より好ましくは７５質量％以上である。 The surfactant of the present invention is not particularly limited, but for example, polyglycerin fatty acid ester, monoglycerin fatty acid ester, sucrose fatty acid ester, organic acid monoglyceride (acetic acid monoglyceride, lactic acid monoglyceride, citric acid monoglyceride, diacetyl). Tartrate monoglyceride, succinic acid monoglyceride), polyoxyethylene derivative, propylene glycol fatty acid ester, sorbitan fatty acid ester, lecithin (soy lecithin, rapeseed lecithin, egg yolk lecithin, sunflower lecithin), enzymatically degraded lecithin (soybean enzymatically degraded lecithin, rapeseed enzymatically degraded lecithin) , Egg yolk enzyme-degraded lecithin) and the like, and one or more selected from these groups may be used in combination. From the viewpoint of maintaining a stable emulsified structure against emulsification destruction due to various emulsification destabilizing factors, it is desirable to contain polyglycerin fatty acid ester, and one or more other surfactants may be used in combination. However, the content ratio of the polyglycerin fatty acid ester in the total amount of the surfactant is preferably 50% by mass or more, and more preferably 75% by mass or more.
本発明のポリグリセリン脂肪酸エステルは、特に限定されるものではないが、好ましくは構成する脂肪酸の炭素数が１２以上及び構成するポリグリセリン平均重合度が３以上であり、より好ましくは構成する脂肪酸の炭素数が１２〜１８及び構成するポリグリセリンの平均重合度が３以上、水酸基価が７７０以上１２００以下であり、かつ全ての水酸基のうち１級水酸基が５０％以上である。炭素数１２〜１８の脂肪酸とはラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、オレイン酸等を挙げられる。一方で、炭素数が１２に満たない脂肪酸で構成されるポリグリセリン脂肪酸エステルでは乳化力に劣る場合や、このようなポリグリセリン脂肪酸エステルを含有するテルペノイド配糖体含有Ｏ／Ｄ乳化組成物では、その香味が飲食品の風味に影響する場合があり、炭素数が１８を超える脂肪酸で構成されるポリグリセリン脂肪酸エステルを含有するテルペノイド配糖体含有Ｏ／Ｄ乳化組成物では、乳化安定性が不十分となる場合がある。 The polyglycerin fatty acid ester of the present invention is not particularly limited, but preferably the constituent fatty acids have 12 or more carbon atoms and the constituent polyglycerin average degree of polymerization is 3 or more, and more preferably the constituent fatty acids. The average degree of polymerization of polyglycerin having 12 to 18 carbon atoms and the constituent polyglycerin is 3 or more, the hydroxyl value is 770 or more and 1200 or less, and the primary hydroxyl group is 50% or more among all the fatty acids. Examples of fatty acids having 12 to 18 carbon atoms include lauric acid, myristic acid, palmitic acid, stearic acid, and oleic acid. On the other hand, when the polyglycerin fatty acid ester composed of a fatty acid having less than 12 carbon atoms is inferior in emulsifying power, or in the terpenoid glycoside-containing O / D emulsifying composition containing such a polyglycerin fatty acid ester, The flavor may affect the flavor of foods and drinks, and the emulsification stability is poor in the terpenoid glycoside-containing O / D emulsified composition containing a polyglycerin fatty acid ester composed of fatty acids having more than 18 carbon atoms. May be sufficient.
本発明のポリグリセリン脂肪酸エステルを構成するポリグリセリンの平均重合度は次式によって算出できる。原料となるポリグリセリンの水酸基価は基準油脂分析試験法（２，３，６，２−１９９６ヒドロキシル価（ピリジン−無水酢酸法））を用いて測定することができる。
ｍ＝７４ｎ＋１８
ＯＨＶ＝５６１１０（ｎ＋２）／ｍ
ｎ：ポリグリセリンの平均重合度
ｍ：ポリグリセリンの平均分子量
ＯＨＶ：ポリグリセリンの水酸基価
The average degree of polymerization of polyglycerin constituting the polyglycerin fatty acid ester of the present invention can be calculated by the following formula. The hydroxyl value of polyglycerin as a raw material can be measured using a standard fat analysis test method (2,3,6,2-1996 hydroxyl value (pyridine-acetic anhydride method)).
m = 74n + 18
OHV = 56110 (n + 2) / m
n: Average degree of polymerization of polyglycerin m: Average molecular weight of polyglycerin OHV: Hydroxyl value of polyglycerin
本発明のポリグリセリン脂肪酸エステルを構成するポリグリセリンにおける全ての水酸基のうちの１級水酸基の割合は、以下のようにして炭素原子に対する核磁気共鳴スペクトル（ＮＭＲ）の測定方法を用いて測定することができる。ポリグリセリン５００ｍｇを重水２．８ｍｌに溶解し、ろ過後ゲートつきデカップリングにより１３Ｃ−ＮＭＲ（１２５ＭＨｚ）スペクトルを得る。ゲートデカップルド測定手法によりピーク強度は炭素数に比例する。１級水酸基と２級水酸基の存在を示す１３Ｃ化学シフトはそれぞれメチレン炭素（ＣＨ２ＯＨ）が６３ｐｐｍ付近、メチン炭素（ＣＨＯＨ）が７１ｐｐｍ付近であり、２種それぞれのシグナル強度の分析により、１級水酸基と２級水酸基の存在比を算出する。但し、２級水酸基を示すメチン炭素（ＣＨＯＨ）は、１級水酸基を示すメチレン炭素に結合するメチン炭素にさらに隣接するメチレン炭素ピークと重なり、それ自体の積分値を得られないため、メチン炭素（ＣＨＯＨ）と隣り合うメチレン炭素（ＣＨ２）の７４ｐｐｍ付近のシグナル強度により積分値を算出する。 The ratio of primary hydroxyl groups to all hydroxyl groups in the polyglycerin constituting the polyglycerin fatty acid ester of the present invention shall be measured by using a method for measuring a nuclear magnetic resonance spectrum (NMR) with respect to carbon atoms as follows. Can be done. 500 mg of polyglycerin is dissolved in 2.8 ml of heavy water, and after filtration, a 13 C-NMR (125 MHz) spectrum is obtained by decoupling with a gate. The peak intensity is proportional to the number of carbon atoms by the gate decoupled measurement method. The 13 C chemical shifts indicating the presence of primary and secondary hydroxyl groups were around 63 ppm for methylene carbon (CH 2 OH) and around 71 ppm for methine carbon (CHOH), respectively. Calculate the abundance ratio of the secondary hydroxyl group to the secondary hydroxyl group. However, the methine carbon (CHOH) showing a secondary hydroxyl group overlaps with the methylene carbon peak further adjacent to the methine carbon bonded to the methylene carbon showing a primary hydroxyl group, and the integrated value of itself cannot be obtained. The integrated value is calculated from the signal intensity near 74 ppm of methylene carbon (CH 2) adjacent to CHOH).
本発明のＩＯＢとは、「Ｉｎｏｒｇａｎｉｃ／Ｏｒｇａｎｉｃ Ｂａｌａｎｃｅ（無機性／有機性比）」の略であって、化合物の有機値に対する化合物の無機値の比に対応する値であり、有機化合物の極性の度合いを示す指標である。具体的には、ＩＯＢ＝無機性値／有機性値として表される。
無機性値、有機性値のそれぞれについては、甲田らの報告（甲田善生著、有機概念図―基礎と応用―１１頁〜１７頁、三共出版、１９８４年発行参照。）に基づき、分子中の炭素原子１個について有機性値が２０、同水酸基１個について無機性値が１００といったように、各種原子又は官能基に応じた無機性値、有機性値が設定されており、有機化合物中の全ての原子及び官能基の無機性値、有機性値を積算することによって、当該有機化合物のＩＯＢが算出することができる。
The IOB of the present invention is an abbreviation for "Inorganic / Organic Balance (inorganic / organic ratio)", which is a value corresponding to the ratio of the inorganic value of a compound to the organic value of the compound, and is a value corresponding to the ratio of the inorganic value of the compound to the organic value of the compound. It is an index showing the degree. Specifically, it is expressed as IOB = inorganic value / organic value.
For each of the inorganic and organic values, refer to the report by Koda et al. (See Yoshio Koda, Organic Conceptual Diagram-Basics and Applications-pages 11 to 17, Sankyo Publishing, 1984). Inorganic values and organic values are set according to various atoms or functional groups, such as an organic value of 20 for one carbon atom and an inorganic value of 100 for one hydroxyl group. The IOB of the organic compound can be calculated by integrating the inorganic and organic values of all the atoms and functional groups.
本発明の界面活性剤のＩＯＢは、好ましくは１以上であり、より好ましくは１．２以上である。ＩＯＢが１より小さい場合、油溶性の素材を水中に安定的に分散することが困難となる場合がある。 The IOB of the surfactant of the present invention is preferably 1 or more, more preferably 1.2 or more. If the IOB is less than 1, it may be difficult to stably disperse the oil-soluble material in water.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物中の界面活性剤の含有割合は、界面活性剤の種類やその他の成分量によっても異なり一概には決定できないが、Ｏ／Ｄ乳化組成物を構成し、及び十分な乳化安定性を得るため、好ましくは０．５質量％以上である。０．５質量％未満では安定な乳化粒子を維持することが困難となる場合があり、水系の飲食品へ添加時に油溶性成分が分離する場合がある。 The content ratio of the surfactant in the terpenoid glycoside-containing O / D emulsified composition of the present invention varies depending on the type of the surfactant and the amount of other components and cannot be unconditionally determined, but the O / D emulsified composition It is preferably 0.5% by mass or more in order to form the above and obtain sufficient emulsification stability. If it is less than 0.5% by mass, it may be difficult to maintain stable emulsified particles, and oil-soluble components may be separated when added to water-based foods and drinks.
本発明におけるテルペノイド配糖体とは、テルペノイドと糖にて構成され、構成するテルペノイドとは、一般的には五炭素化合物であるイソプレンユニットを構成単位とする一群の天然物化合物であり、特に限定されるものではないが、例えば、リモネン、シメン、テルピネン、テルピノレン、ピネン、リナロール、シトラール、ゲラニオール、メントール、チモール、カルバクロール、チオテルピネオール等のモノテルペン類及びその誘導体、バレンセン、ノートカトン、カリオフィレン、フムレン、ビサボレン、クベベン、ファルネセン、カジネン等のセスキテルペン類及びその誘導体、カーウェオール、カフェストール、ステビオール、レチノール、レチナール、フィトール等のジテルペン類及びその誘導体、スクアレン、ラノステロール、ククルビタン等のトリテルペン類及びその誘導体が挙げられ、テルペノイド配糖体とはこれらテルペノイドに糖が付加した化合物を指す。本発明におけるテルペノイド配糖体の組成は限定されるものではないが、好ましくはテルペノイド配糖体の平均分子量が５００〜１５００であり、より好ましくはテルペノイド配糖体を構成するテルペノイドが炭素数１０、１５、２０、３０のいずれかのイソプレノイドを含有するものであり、最も好ましくはテルペノイド配糖体を構成するテルペノイドと糖のモル比率が１：１〜１：５である。 The terpenoid glycoside in the present invention is composed of a terpenoid and a sugar, and the terpenoid constituting the terpenoid is a group of natural compounds having an isoprene unit, which is generally a pentacarbon compound, as a constituent unit, and is particularly limited. Although not, for example, monoterpenes such as limonene, simene, terpinen, terpinolene, pinen, linalol, citral, geraniol, menthol, timol, carbachlor, thioterpineol and their derivatives, valensen, notecaton, cariophyllene, humlen. , Visaborene, Kubeben, Farnesen, Kadinen and other sesquiterpenoids and their derivatives, Kawaol, Cafestol, Steviol, Retinol, Retinal, Fitol and other diterpenoids and their derivatives, Squalene, lanosterol, Kukurubitane and other triterpenoids and their derivatives. Derivatives are mentioned, and the terpenoid glycoside refers to a compound in which a sugar is added to these terpenoids. The composition of the terpenoid glycoside in the present invention is not limited, but the average molecular weight of the terpenoid glycoside is preferably 500 to 1500, and more preferably, the terpenoid constituting the terpenoid glycoside has 10 carbon atoms. It contains any of 15, 20, and 30 isoprenoids, and most preferably, the molar ratio of terpenoids and sugars constituting the terpenoid glycoside is 1: 1 to 1: 5.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物中のテルペノイド配糖体の含有割合は、特に限定されるものではないが、好ましくは０．１〜３０質量％であり、より好ましくは０．５〜２０質量％であり、最も好ましくは１〜１０質量％である。 The content ratio of the terpenoid glycoside in the terpenoid glycoside-containing O / D emulsifying composition of the present invention is not particularly limited, but is preferably 0.1 to 30% by mass, more preferably 0. .5 to 20% by mass, most preferably 1 to 10% by mass.
本発明の食用油脂とは、食用に用いられる油脂であれば特に限定されるものではないが、例えば、パーム油、カカオ脂、ヤシ油、パーム核油、大豆油、菜種油、コーン油、綿実油、サフラワー油、ヒマワリ油、米油、ゴマ油、オリーブ油、グレープシード油、落花生油、亜麻仁油、乳脂、ラード、牛脂、魚油、中鎖脂肪酸含有トリグリセリド等の油脂、これら油脂を、混合、分別、水素添加、及びエステル交換等の群より選ばれる１種又は２種以上の加工を行った油脂が挙げられる。より安定な乳化構造を維持するといった観点から、好ましくは食用油脂が中鎖脂肪酸含有トリグリセリドを含有し、より好ましくは食用油脂を構成する脂肪酸の全量中のカプリル酸の含有割合が２０質量％以上となる食用油脂が望ましい。 The edible oil and fat of the present invention is not particularly limited as long as it is an edible oil and fat, but for example, palm oil, coconut oil, palm oil, palm kernel oil, soybean oil, rapeseed oil, corn oil, cotton seed oil, etc. Oils such as saflower oil, sunflower oil, rice oil, sesame oil, olive oil, grape seed oil, peanut oil, flaxseed oil, milk fat, lard, beef fat, fish oil, medium chain fatty acid-containing triglyceride, etc. Examples thereof include oils and fats that have been processed by one or more types selected from the group of addition and ester exchange. From the viewpoint of maintaining a more stable emulsified structure, edible fats and oils preferably contain medium-chain fatty acid-containing triglycerides, and more preferably caprylic acid content in the total amount of fatty acids constituting edible fats and oils is 20% by mass or more. Edible fats and oils are desirable.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物中の食用油脂の含有割合は、特に限定されるものではないが、好ましくは５〜３０質量％であり、より好ましくは１０〜２０質量％である。 The content ratio of the edible oil / fat in the terpenoid glycoside-containing O / D emulsified composition of the present invention is not particularly limited, but is preferably 5 to 30% by mass, more preferably 10 to 20% by mass. Is.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物に含有される界面活性剤、テルペノイド配糖体、食用油脂の質量比率は、乳化組成物の乳化安定性の観点から次式を満たすことを必要とする。
界面活性剤：テルペノイド配糖体＝１：３０〜３０：１
テルペノイド配糖体：食用油脂＝１：３０〜３０：１
The mass ratio of the surfactant, the terpenoid glycoside, and the edible oil / fat contained in the terpenoid glycoside-containing O / D emulsification composition of the present invention satisfies the following equation from the viewpoint of emulsification stability of the emulsified composition. I need.
Surfactant: Terpenoid glycoside = 1:30 to 30: 1
Terpenoid glycosides: edible fats and oils = 1:30 to 30: 1
本発明における多価アルコールとは、１つの分子内に２個以上の水酸機を有する化合物の総称であり特に限定されるものではないが、例えば、グリセリン、プロピレングリコール、ソルビトール、マルチトール、キシリトール、エリスリトール、ラクチトール、ソルビタン、キシロース、アラビノース、マンノース、乳糖、砂糖、カップリングシュガー、ブドウ糖、酵素水飴、酸糖化水飴、麦芽糖水飴、麦芽糖、異性化糖、果糖、還元麦芽糖、還元澱粉水飴、蜂蜜等が挙げられる。Ｏ／Ｄ乳化組成物を構成すること、及び十分な乳化安定性を得るために、好ましくは多価アルコールにグリセリン、ソルビトール、マルチトールのいずれかを含有する。
本発明における多価アルコール水溶液中の水の含有割合は、好ましくは多価アルコールに対して５０質量％以下であり、より好ましくは３０質量％以下である。
The polyvalent alcohol in the present invention is a general term for compounds having two or more hydroxide machines in one molecule and is not particularly limited, but for example, glycerin, propylene glycol, sorbitol, maltitol, xylitol. , Erythritol, lactitol, sorbitol, xylitol, arabinose, mannose, lactose, sugar, coupling sugar, glucose, enzyme water candy, acid saccharified water candy, maltose water candy, maltose, isomerized sugar, fructose, reduced maltose, reduced starch water candy, honey, etc. Can be mentioned. In order to compose the O / D emulsification composition and obtain sufficient emulsification stability, the polyhydric alcohol preferably contains any one of glycerin, sorbitol, and maltitol.
The content ratio of water in the aqueous solution of the polyhydric alcohol in the present invention is preferably 50% by mass or less, more preferably 30% by mass or less, based on the polyhydric alcohol.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物は、多価アルコール又は多価アルコール水溶液中で調製する場合において、多価アルコール又は多価アルコール水溶液中に界面活性剤を溶解させた後、テルペノイド配糖体と食用油脂を添加し、乳化装置を用い乳化することにより得られる。テルペノイド配糖体の添加方法は特に限定されるものではないが、例えば、界面活性剤を溶解させた多価アルコール又は多価アルコール水溶液中に添加する方法、又は食用油脂中に混合して油相として添加する方法等が挙げられ、より安定な乳化組成物を得る観点で、好ましくは食用油脂中に混合して油相として添加する方法である。 When the terpenoid glycoside-containing O / D emulsified composition of the present invention is prepared in a polyhydric alcohol or an aqueous solution of a polyhydric alcohol, the surfactant is dissolved in the polyhydric alcohol or the aqueous solution of the polyhydric alcohol, and then the surfactant is dissolved in the polyhydric alcohol or the aqueous solution of the polyhydric alcohol. It is obtained by adding a terpenoid glycoside and edible oil and fat and emulsifying using an emulsifying device. The method of adding the terpenoid glycoside is not particularly limited, but for example, it is added in a polyhydric alcohol or an aqueous solution of a polyhydric alcohol in which a surfactant is dissolved, or the oil phase is mixed in an edible oil or fat. From the viewpoint of obtaining a more stable emulsified composition, it is preferably a method of mixing with an edible oil and fat and adding as an oil phase.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物は、十分な乳化安定性と分散性を得ることを可能とするため、好ましくは水中分散時に平均粒子径１．０μｍ以下の乳化粒子径となるように調製する。乳化粒子径の粒度分布測定法としては、特に限定されるものではないが、例えば、光学顕微鏡法、共焦点レーザー顕微鏡法、電子顕微鏡法、原子間力顕微鏡法、静的光散乱法、動的光散乱法、レーザー回折法等が挙げられ、それぞれの原理に対応した市販の粒度分布計等を用いることができる。本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物を水中に分散させた時の乳化粒子径は、例えば、ベックマンコールター社の粒度分布測定器（Ｌ−２３０）を用いることで容易に測定することができる。 The terpenoid glycoside-containing O / D emulsified composition of the present invention preferably has an emulsified particle size of 1.0 μm or less when dispersed in water, because it enables sufficient emulsification stability and dispersibility. Prepare to be. The particle size distribution measurement method for the emulsified particle size is not particularly limited, but is, for example, optical microscopy, confocal laser microscopy, electron microscopy, interatomic force microscopy, static light scattering, and dynamic light scattering. Examples include a light scattering method and a laser diffraction method, and a commercially available particle size distribution meter or the like corresponding to each principle can be used. The emulsified particle size when the terpenoid glycoside-containing O / D emulsified composition of the present invention is dispersed in water can be easily measured by using, for example, a particle size distribution measuring device (L-230) manufactured by Beckman Coulter. be able to.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物には必要に応じて公知の酸化防止剤を併用してもよい。特に限定されるものではないが、例えば、油溶性酸化防止剤（カンゾウ油抽出物、ゴマ油不けん化物、γ−オリザノール、ナタネ油抽出物、トコフェロール）、水溶性酸化防止剤（Ｌ−アスコルビン酸、Ｌ−アスコルビン酸エステル、Ｌ−アスコルビン酸ナトリウム、エリソルビン酸、エリソルビン酸ナトリウム、没食子酸、クロロゲン酸、ブドウ種子抽出物、ヒマワリ抽出物、ヤマモモ抽出物、食用カンナ抽出物、ブルーベリー葉抽出物等）、水や油に難溶である酸化防止剤（ドクダミ抽出物、アオイ花抽出物、ピメンタ抽出物等）、金属封鎖剤（グルコン酸、コウジ酸、フィチン酸、ポリリン酸、キチン、キトサン等）、アミノ酸類、クエン酸等の有機酸類又その塩類、リン酸等の無機酸類又その塩類、ヘスペリジン、ヘスペレチン等が挙げられ、これらの群より選ばれる１種又は２種以上を併用してもよい。 A known antioxidant may be used in combination with the terpenoid glycoside-containing O / D emulsified composition of the present invention, if necessary. Although not particularly limited, for example, an oil-soluble antioxidant (kanzo oil extract, sesame oil unsaponifiable matter, γ-orizanol, rapeseed oil extract, tocopherol), a water-soluble antioxidant (L-ascorbic acid, L-ascorbic acid ester, L-ascorbic acid sodium, erythorbic acid, sodium erythorbic acid, gallic acid, chlorogenic acid, grape seed extract, sunflower extract, yamamomo extract, edible canna extract, blueberry leaf extract, etc.), Antioxidants that are sparingly soluble in water and oil (Dokudami extract, Aoi flower extract, Pimenta extract, etc.), metal sequestering agents (gluconic acid, kodiic acid, phytic acid, polyphosphate, chitin, chitosan, etc.), amino acids Examples include organic acids such as citric acid and salts thereof, inorganic acids such as phosphoric acid and salts thereof, hesperidin, hesperetin and the like, and one or more selected from these groups may be used in combination.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物には必要に応じて公知の香料を併用してもよい。特に限定されるものではないが、例えば、精油、エキストラクト、オレオレジン、回収フレーバー、単離香料等の天然香料素材やアルコール類、エステル類、アルデヒド類、ケトン類、ラクトン類等の合成香料素材の群より選ばれる１種又は２種以上を混合したものが挙げられ、形態として、油溶性香料、水溶性香料、乳化香料、粉末香料等の香料が挙げられ、これらの群より選ばれる１種又は２種以上併用してもよい。 A known fragrance may be used in combination with the terpenoid glycoside-containing O / D emulsified composition of the present invention, if necessary. Although not particularly limited, for example, natural fragrance materials such as essential oils, extracts, oleoledins, recovered flavors, and isolated fragrances, and synthetic fragrance materials such as alcohols, esters, aldehydes, ketones, and lactones. One or a mixture of two or more selected from the group of fragrances, and examples thereof include fragrances such as oil-soluble fragrances, water-soluble fragrances, emulsified fragrances, and powdered fragrances. Alternatively, two or more types may be used in combination.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物には必要に応じて公知の高甘味度甘味料を併用してもよい。特に限定されるものではないが、例えば、アセスルファムカリウム、スクラロース、アスパルテーム、サッカリン、ネオテーム、ソーマチン、グリチルリチン、甘草、羅漢果等が挙げられ、これらの群より選ばれる１種又は２種以上併用してもよい。 A known high-sweetness sweetener may be used in combination with the terpenoid glycoside-containing O / D emulsified composition of the present invention, if necessary. Although not particularly limited, for example, acesulfame potassium, sucralose, aspartame, saccharin, neotame, thaumatin, glycyrrhizin, licorice, Luo Han Guo and the like can be mentioned, and one or more selected from these groups may be used in combination. good.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物を調製する乳化装置は、特に限定されるものではないが、例えば、ホモミキサー、コロイドミル、高圧ホモジナイザー、超高圧ホモジナイザー等が挙げられる。 The emulsifying device for preparing the terpenoid glycoside-containing O / D emulsifying composition of the present invention is not particularly limited, and examples thereof include a homomixer, a colloid mill, a high-pressure homogenizer, and an ultra-high-pressure homogenizer.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物は、親水性乳化剤を含有する多価アルコール又は多価アルコール水溶液に、油相を添加・攪拌することにより得ることができる。例えば、界面活性剤を含有する多価アルコールを、４０〜８０℃の温度で、ホモミキサーを用い５００〜２００００ｒｐｍ、好ましくは１０００〜１００００ｒｐｍで攪拌し、この中に油相を少量ずつ添加した後、上記の温度を保持したまま１〜６０分間、好ましくは５〜３０分間の条件下にて攪拌する。攪拌後、好ましくは高圧ホモジナイザー等を使用する。ホモジナイザーの均質化圧力は５ＭＰａ以上であり、好ましくは２０ＭＰａ以上であり、より好ましくは５０ＭＰａ以上であり、最も好ましくは１００ＭＰａ以上である。テルペノイド配糖体は多価アルコール又は多価アルコール水溶液、油相いずれに添加してもよいが、好ましくは油相に添加する。 The terpenoid glycoside-containing O / D emulsified composition of the present invention can be obtained by adding and stirring an oil phase to a polyhydric alcohol or a polyhydric alcohol aqueous solution containing a hydrophilic emulsifier. For example, a polyhydric alcohol containing a surfactant is stirred at a temperature of 40 to 80 ° C. using a homomixer at 500 to 20000 rpm, preferably 1000 to 10000 rpm, and an oil phase is added little by little to the mixture. Stir under the conditions of 1 to 60 minutes, preferably 5 to 30 minutes while maintaining the above temperature. After stirring, a high-pressure homogenizer or the like is preferably used. The homogenizer homogenization pressure is 5 MPa or more, preferably 20 MPa or more, more preferably 50 MPa or more, and most preferably 100 MPa or more. The terpenoid glycoside may be added to the polyhydric alcohol, the polyhydric alcohol aqueous solution, or the oil phase, but is preferably added to the oil phase.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物を含有する飲食品とは、特に限定されるものではないが、例えば、柑橘果汁や野菜果汁等の果実飲料又は野菜ジュース、コーラ、ジンジャエール、サイダー等の炭酸飲料、スポーツドリンク、ビタミン含有飲料等の清涼飲料水、アルコール飲料、ミネラル含有飲料、コーヒー、ココア、緑茶、紅茶、抹茶等の嗜好性飲料及びそれらに乳性分を配合した乳含有嗜好性飲料、乳酸菌飲料、ヨーグルト、ゼリー、プディング、ムース等のデザート類、ケーキ、クラッカー、ビスケット、パイ、饅頭等といった洋菓子及び和菓子を含有する焼菓子や蒸菓子等の菓子類、米菓、スナック類、アイスクリームやシャーベット等の冷菓並びに氷菓、チューインガム、ハードキャンディ、ヌガーキャンデー、ゼリービーンズ等を含有する糖菓一般、果実フレーバーソースやチョコレートソース等のソース類、バタークリーム、フラワーペーストやホイップクリーム等のクリーム類、イチゴジャムやマーマレード等のジャム、菓子パン等のパン、焼き肉、焼き鳥、鰻蒲焼き等に用いられるタレ、トマトケチャップ、ソース、麺つゆ等の調味料、蒲鉾等の練り製品、ソーセージ等の食肉加工品、レトルト食品、漬け物、佃煮、珍味、惣菜、冷凍食品等が挙げられる。食品への使用においては、食品原料及び各種食品添加物に適当な濃度となるように混合し使用してもよい。
以下、本発明の態様を実施例によりさらに記載し、開示する。この実施例は、単なる本発明の例示であり、何ら限定を意味するものではない。
The food or drink containing the terpenoid sugar-containing O / D emulsified composition of the present invention is not particularly limited, but for example, a fruit beverage such as citrus fruit juice or vegetable fruit juice, or vegetable juice, cola, ginger ale, etc. Carbonated beverages such as cider, sports drinks, soft drinks such as vitamin-containing beverages, alcoholic beverages, mineral-containing beverages, favorite beverages such as coffee, cocoa, green tea, tea, matcha, and milk-containing beverages containing dairy ingredients. Beverages such as palatable beverages, lactic acid bacteria beverages, yogurt, jelly, pudding, mousse, etc., Western confectionery such as cakes, crackers, biscuits, pies, buns, etc. , Cold confectionery such as ice cream and sherbet, general sugar confectionery containing ice confectionery, chewing gum, hard candy, nouga candy, jelly beans, etc., sauces such as fruit flavor sauce and chocolate sauce, butter cream, flower paste, whipped cream, etc. Creams, jams such as strawberry jam and marmalade, bread such as confectionery bread, grilled meat, grilled chicken, sauce used for grilled eel, tomato ketchup, sauce, seasonings such as noodle soup, paste products such as sesame seeds, meat processing such as sausage Products, retort foods, pickles, boiled foods, delicacies, side dishes, frozen foods, etc. can be mentioned. When used in foods, it may be mixed with food raw materials and various food additives so as to have an appropriate concentration.
Hereinafter, aspects of the present invention will be further described and disclosed by way of examples. This example is merely an example of the present invention and does not mean any limitation.
実施例１、比較例１
表１、２に記載の界面活性剤とテルペノイド配糖体を用い、下記記載のＯ／Ｄ乳化組成物調製方法にて、本発明品１〜２０のＯ／Ｄ乳化組成物、比較品１、２を調製した。
Example 1, Comparative Example 1
Using the surfactants and terpenoid glycosides shown in Tables 1 and 2, the O / D emulsified compositions of the present invention products 1 to 20 and Comparative Products 1 and 2 were prepared by the O / D emulsified composition preparation method described below. 2 was prepared.
Ｏ／Ｄ乳化組成物調製方法１
全量１０００ｇのＯ／Ｄ乳化組成物を調製するため、表３又は４に記載の配合割合にて、多価アルコールに界面活性剤及びテルペノイド配糖体を２Ｌのビーカーに添加し６０℃に加温した。ホモミキサーを用い適宜攪拌し、この中に食用油脂を少量ずつ添加した後、上記の温度を保持したまま３０分間攪拌し、本発明品又は比較品を調製した。
O / D emulsified composition preparation method 1
In order to prepare an O / D emulsified composition having a total amount of 1000 g, a surfactant and a terpenoid glycoside were added to a polyhydric alcohol in a 2 L beaker at the blending ratios shown in Table 3 or 4, and the mixture was heated to 60 ° C. bottom. The product of the present invention or a comparative product was prepared by appropriately stirring with a homomixer, adding edible oils and fats to the mixture little by little, and then stirring for 30 minutes while maintaining the above temperature.
Ｏ／Ｄ乳化組成物調製方法２
全量１０００ｇのＯ／Ｄ乳化組成物を調製するため、表３又は４に記載の配合割合にて、テルペノイド配糖体と食用油脂を１Ｌのビーカーに添加し、ホモミキサーを用い適宜攪拌し、この中にテルペノイド配糖体を添加した油相を調製した。別途多価アルコールに界面活性剤を２Ｌのビーカーに添加し６０℃に加温した。ホモミキサーを用い適宜攪拌し、この中にテルペノイド配糖体を添加した油相を少量ずつ添加した後、上記の温度を保持したまま３０分間攪拌し、本発明品又は比較品を調製した。
O / D emulsified composition preparation method 2
In order to prepare an O / D emulsified composition having a total amount of 1000 g, terpenoid glycosides and edible oils and fats were added to a 1 L beaker at the blending ratios shown in Table 3 or 4, and the mixture was appropriately stirred using a homomixer. An oil phase was prepared by adding a terpenoid glycoside therein. Separately, a surfactant was added to a polyhydric alcohol in a 2 L beaker and heated to 60 ° C. The product of the present invention or a comparative product was prepared by appropriately stirring with a homomixer, adding the oil phase to which the terpenoid glycoside was added little by little, and then stirring for 30 minutes while maintaining the above temperature.
Ｏ／Ｄ乳化組成物調製方法３
全量１０００ｇのＯ／Ｄ乳化組成物を調製するため、表３又は４に記載の配合割合にて、テルペノイド配糖体と食用油脂を１Ｌのビーカーに添加し、ホモミキサーを用い適宜攪拌し、この中にテルペノイド配糖体を添加した油相を調製した。別途多価アルコールに界面活性剤を２Ｌのビーカーに添加し６０℃に加温した。ホモミキサーを用い適宜攪拌し、この中にテルペノイド配糖体を添加した油相を少量ずつ添加した後、上記の温度を保持したまま３０分間攪拌した。攪拌終了後水を加え、６０℃で高圧ホモジナイザー処理をし、本発明品又は比較品を調製した。
O / D emulsified composition preparation method 3
In order to prepare an O / D emulsified composition having a total amount of 1000 g, terpenoid glycosides and edible oils and fats were added to a 1 L beaker at the blending ratios shown in Table 3 or 4, and the mixture was appropriately stirred using a homomixer. An oil phase was prepared by adding a terpenoid glycoside therein. Separately, a surfactant was added to a polyhydric alcohol in a 2 L beaker and heated to 60 ° C. The mixture was appropriately stirred using a homomixer, and the oil phase to which the terpenoid glycoside was added was added little by little, and then the mixture was stirred for 30 minutes while maintaining the above temperature. After the stirring was completed, water was added and treated with a high-pressure homogenizer at 60 ° C. to prepare the product of the present invention or a comparative product.
乳化安定性評価方法
得られた本発明品１〜２０のＯ／Ｄ乳化組成物、比較品１、２について、２５℃の恒温槽に１ヶ月保管、又は５５℃の恒温槽に１週間保管し乳化安定性を評価した。性状については、乳化又は分離の状態を目視で観察することで、下記評価基準にて評価した。その結果を表３又は４に記載した。
Emulsification Stability Evaluation Method The obtained O / D emulsification compositions 1 to 20 of the present invention and Comparative Products 1 and 2 were stored in a constant temperature bath at 25 ° C. for 1 month or in a constant temperature bath at 55 ° C. for 1 week. Emulsification stability was evaluated. The properties were evaluated according to the following evaluation criteria by visually observing the state of emulsification or separation. The results are shown in Table 3 or 4.
評価基準
２０：外観に変化は見られない。
１５：外観に大きな変化は見られないが下層部に濃度勾配が見られる。
１０：油相の分離は見られないが全体的に濃度勾配が見られる。
５：上部に若干の油滴が観察される。
１：油相と水相が完全に分離している。
Evaluation Criteria 20: No change in appearance.
15: No significant change in appearance is seen, but a concentration gradient is seen in the lower layer.
10: No separation of the oil phase is observed, but an overall concentration gradient is observed.
5: Some oil droplets are observed on the upper part.
1: The oil phase and the aqueous phase are completely separated.
処方例１ 缶コーヒー
コーヒー抽出液（Ｂｘ３．０） ３０．０ｇ
牛乳 ２０．０ｇ
乳化剤 ０．１ｇ
重曹 ０．１ｇ
本発明品８ ０．１ｇ
水 残部
合計 １００．０ｇ
上記処方に従って各成分を混合し、加熱溶解後、ホモジナイザー（１５ＭＰａ）にて均質化した。缶に充填後、１２１℃で３０分間レトルト殺菌した。得られた缶コーヒーは油脂の分離もなく安定な状態であった。
Prescription example 1 Canned coffee Coffee extract (Bx3.0) 30.0 g
Milk 20.0g
Emulsifier 0.1g
Baking soda 0.1g
Product of the present invention 8 0.1 g
Water balance total 100.0g
Each component was mixed according to the above formulation, dissolved by heating, and homogenized with a homogenizer (15 MPa). After filling the cans, they were retort-sterilized at 121 ° C. for 30 minutes. The obtained canned coffee was in a stable state without separation of fats and oils.
処方例２ ヨーグルト
Ａ：水 ３５．３ｇ
脱脂粉乳 ９．０ｇ
無塩バター ５．０ｇ
Ｂ：水 ４７．０ｇ
ＨＭペクチン ０．５ｇ
本発明品９ ０．２ｇ
Ａの各成分を混合して５０℃で加熱溶解した。これを、８０℃で１０分間加熱して調製したＢの混合物に配合して、全量を水にて９７ｇに調製した。次いでホモジナイザー（１５ＭＰａ）にて均質化し、９０℃で５分間殺菌した。４０℃まで冷ました後、スターターヨーグルト３ｇを加え容器に充填し、４０℃恒温器にて６時間発酵させてヨーグルトを調製した。得られたヨーグルトは油脂の分離もなく安定な状態であった。
Prescription example 2 Yogurt A: 35.3 g of water
Skim milk powder 9.0g
Unsalted butter 5.0g
B: Water 47.0 g
HM pectin 0.5g
Product of the present invention 9 0.2 g
Each component of A was mixed and dissolved by heating at 50 ° C. This was added to the mixture of B prepared by heating at 80 ° C. for 10 minutes, and the total amount was adjusted to 97 g with water. It was then homogenized with a homogenizer (15 MPa) and sterilized at 90 ° C. for 5 minutes. After cooling to 40 ° C., 3 g of starter yogurt was added, filled in a container, and fermented in a 40 ° C. incubator for 6 hours to prepare yogurt. The obtained yogurt was in a stable state without separation of fats and oils.
本発明のテルペノイド配糖体含有Ｏ／Ｄ乳化組成物を用いることにより、長期間保存される飲食品中等、経時的な乳化不安定化が懸念される条件下においても安定的に使用することができ、品質の良好なテルペノイド配糖体を含有する飲食品を提供することが可能となる。 By using the terpenoid glycoside-containing O / D emulsification composition of the present invention, it can be stably used even under conditions where there is a concern about emulsification instability over time, such as in foods and drinks stored for a long period of time. It is possible to provide foods and drinks containing terpenoid glycosides of good quality.
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