JP6847515B2 - Cold-resistant triglyceride - Google Patents
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- JP6847515B2 JP6847515B2 JP2017008162A JP2017008162A JP6847515B2 JP 6847515 B2 JP6847515 B2 JP 6847515B2 JP 2017008162 A JP2017008162 A JP 2017008162A JP 2017008162 A JP2017008162 A JP 2017008162A JP 6847515 B2 JP6847515 B2 JP 6847515B2
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- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims description 97
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 114
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 90
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 88
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 86
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 54
- 229930195729 fatty acid Natural products 0.000 claims description 54
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- 239000002253 acid Substances 0.000 claims description 5
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- 125000005457 triglyceride group Chemical group 0.000 claims description 4
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims description 4
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- 150000004668 long chain fatty acids Chemical class 0.000 description 7
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- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
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- 235000020880 diabetic diet Nutrition 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- WLGSIWNFEGRXDF-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O.CCCCCCCCCCCC(O)=O WLGSIWNFEGRXDF-UHFFFAOYSA-N 0.000 description 1
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- 235000020887 ketogenic diet Nutrition 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
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- -1 medium-chain fatty acid triglycerides Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ACXGEQOZKSSXKV-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O.CCCCCCCC(O)=O ACXGEQOZKSSXKV-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- 239000008117 stearic acid Substances 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 125000005472 straight-chain saturated fatty acid group Chemical group 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000003203 triacylglycerol group Chemical group 0.000 description 1
- 229940121343 tricaprilin Drugs 0.000 description 1
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
本発明は、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合、ｎ−デカン酸の割合及び／又はｎ−ドデカン酸の割合が特定の数値範囲となるようにした、耐冷性トリグリセリド、及び、該トリグリセリドの耐冷性を向上させる方法に関する。 The present invention is a triglyceride containing a medium-chain fatty acid as a constituent fatty acid, and the ratio of n-octanoic acid, the ratio of n-decanoic acid and / or n-dodecane to the total amount of the medium-chain fatty acids constituting the triglyceride. The present invention relates to a cold-tolerant triglyceride in which the ratio of an acid is within a specific numerical range, and a method for improving the cold-tolerance of the triglyceride.
高齢者や病中病後の患者は、通常の食事を十分に取ることができないため、低栄養状態に陥る場合がある。このような事態に対処するため、少量の摂取で十分な栄養を摂取できるような食品の開発が行われている。特に、エネルギー（カロリー）の摂取に主眼をおいた場合、このような食品の脂質含量を高めた方が効率がよい。加えて、ケトン食（例えば、特許文献１）や糖尿病食、低炭水化物ダイエットに対応する食品とするには、高脂質、低糖質であることが好ましい。 Elderly people and post-illness patients may become undernourished due to inadequate normal diet. In order to deal with such a situation, foods are being developed so that sufficient nutrition can be obtained with a small amount of intake. In particular, when focusing on energy (calorie) intake, it is more efficient to increase the lipid content of such foods. In addition, high fat and low sugar are preferable in order to prepare a ketogenic diet (for example, Patent Document 1), a diabetic diet, and a food corresponding to a low-carbohydrate diet.
このような食品に利用される脂質としては、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリド（以下、「ＭＴＧ」ともいう。）がよく知られている。ＭＴＧに含まれる中鎖脂肪酸は、消化管内で速やかに吸収され、肝臓で極めて早く分解されエネルギーに変わることから、栄養学的な利点を有している。しかしながら、ＭＴＧを一度に大量に摂取すると、咽頭部や胃上部の刺激、胃もたれやむかつき等の不快感を誘発することがある。 As a lipid used in such foods, a triglyceride containing a medium-chain fatty acid as a constituent fatty acid (hereinafter, also referred to as "MTG") is well known. Medium-chain fatty acids contained in MTG have a nutritional advantage because they are rapidly absorbed in the digestive tract and decomposed very quickly in the liver into energy. However, ingestion of a large amount of MTG at one time may induce irritation of the pharynx and upper stomach, and discomfort such as stomach upset and nausea.
ＭＴＧの中でも、構成脂肪酸中に炭素数が１０であるｎ−デカン酸を多く含むものは、咽頭部や胃上部の刺激、胃もたれやむかつき等の不快感が少ないことが報告されている（例えば、特許文献２）。しかしながら、構成脂肪酸に占めるｎ−デカン酸の含有量が高いＭＴＧにおいては、室温において固化しやすく、もしくは結晶が析出しやすく、一部の食品形態（例えば、乳化食品）では、使い勝手が良いとはいえない問題があった。 Among MTGs, those containing a large amount of n-decanoic acid having 10 carbon atoms in the constituent fatty acids have been reported to have less discomfort such as irritation of the pharynx and upper stomach, stomach upset and nausea (for example). , Patent Document 2). However, in MTG having a high content of n-decanoic acid in the constituent fatty acids, it is easy to solidify at room temperature or crystals are easily precipitated, and it is easy to use in some food forms (for example, emulsified foods). There was a problem I couldn't say.
本発明の課題は、室温（２０℃）においても固化又は結晶化しにくい、耐冷性を備えた、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリド、及び該トリグリセリドの耐冷性を向上させる方法を提供することである。 An object of the present invention is to provide a triglyceride containing a medium-chain fatty acid as a constituent fatty acid, which is hard to solidify or crystallize even at room temperature (20 ° C.) and has cold resistance, and a method for improving the cold resistance of the triglyceride. Is.
本発明者は、上記課題を解決すべく鋭意研究を行った結果、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドにおいて、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合、ｎ−デカン酸の割合及び／又はｎ−ドデカン酸の割合を特定の数値範囲となるようにすることで、本課題を解決できることを見いだし、本発明を完成させた。 As a result of diligent research to solve the above problems, the present inventor has found that, among triglycerides containing medium-chain fatty acids as constituent fatty acids, the ratio of n-octanoic acid to the total amount of medium-chain fatty acids constituting the triglyceride. We have found that this problem can be solved by setting the ratio of n-decanoic acid and / or the ratio of n-dodecanoic acid within a specific numerical range, and completed the present invention.
すなわち、本発明は、以下のものを提供する。
〔１〕構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が１１〜２４質量％であり、ｎ−デカン酸の割合が７６〜８９質量％である、前記トリグリセリド。
〔２〕前記中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が２０質量％であり、ｎ−デカン酸の割合が８０質量％である、〔１〕に記載のトリグリセリド。
〔３〕構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−デカン酸の割合が９１〜９９質量％であり、ｎ−ドデカン酸の割合が１〜９質量％である、前記トリグリセリド。
〔４〕前記中鎖脂肪酸の全量に占める、ｎ−デカン酸の割合が９５質量％であり、ｎ−ドデカン酸の割合が５質量％である、〔３〕に記載のトリグリセリド。
〔５〕構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が１〜２５質量％であり、ｎ−デカン酸の割合が７５〜９０質量％であり、ｎ−ドデカン酸の割合が５〜１４質量％であり、前記中鎖脂肪酸の全量に占めるｎ−オクタン酸、ｎ−デカン酸およびｎ−ドデカン酸の割合の総計が１００質量％である、前記トリグリセリド。
〔６〕構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が５〜１５質量％であり、ｎ−デカン酸の割合が７５〜８５質量％であり、ｎ−ドデカン酸の割合が５〜１４質量％であり、前記中鎖脂肪酸の全量に占めるｎ−オクタン酸、ｎ−デカン酸およびｎ−ドデカン酸の割合の総計が１００質量％である、前記トリグリセリド。
〔７〕前記中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が１０質量％であり、ｎ−デカン酸の割合が８０質量％であり、ｎ−ドデカン酸の割合が１０質量％である、〔５〕又は〔６〕に記載のトリグリセリド。
〔８〕前記構成脂肪酸が中鎖脂肪酸のみである、〔１〕ないし〔７〕のいずれか１項に記載のトリグリセリド。
〔９〕前記トリグリセリドが、トリカプリリン、トリカプリン及び／又はトリラウリンの混合物からなる、〔１〕ないし〔８〕のいずれか１項に記載のトリグリセリド。
〔１０〕構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドにおいて、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合を１１〜２４質量％、ｎ−デカン酸の割合を７６〜８９質量％とすることにより、前記トリグリセリドの耐冷性を向上させる方法。
〔１１〕構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドにおいて、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−デカン酸の割合を９１〜９９質量％、ｎ−ドデカン酸の割合を１〜９質量％とすることにより、前記トリグリセリドの耐冷性を向上させる方法。
〔１２〕構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドにおいて、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合を１〜２５質量％、ｎ−デカン酸の割合を７５〜９０質量％、ｎ−ドデカン酸の割合を５〜１４質量％（ただし、前記中鎖脂肪酸の全量に占めるｎ−オクタン酸、ｎ−デカン酸およびｎ−ドデカン酸の割合の総計は１００質量％である）とすることにより、前記トリグリセリドの耐冷性を向上させる方法。
That is, the present invention provides the following.
[1] A triglyceride containing a medium-chain fatty acid as a constituent fatty acid, wherein the proportion of n-octanoic acid in the total amount of the medium-chain fatty acid constituting the triglyceride is 11 to 24% by mass, and that of n-decanoic acid. The triglyceride having a proportion of 76-89% by mass.
[2] The triglyceride according to [1], wherein the proportion of n-octanoic acid in the total amount of the medium-chain fatty acid is 20% by mass, and the proportion of n-decanoic acid is 80% by mass.
[3] A triglyceride containing a medium-chain fatty acid as a constituent fatty acid, wherein the proportion of n-decanoic acid in the total amount of the medium-chain fatty acid constituting the triglyceride is 91 to 99% by mass, and that of n-dodecanoic acid. The triglyceride having a proportion of 1-9% by mass.
[4] The triglyceride according to [3], wherein the proportion of n-decanoic acid in the total amount of the medium-chain fatty acid is 95% by mass, and the proportion of n-dodecanoic acid is 5% by mass.
[5] A triglyceride containing a medium-chain fatty acid as a constituent fatty acid, wherein the proportion of n-octanoic acid in the total amount of the medium-chain fatty acid constituting the triglyceride is 1 to 25% by mass, and that of n-decanoic acid. The ratio is 75 to 90% by mass, the ratio of n-dodecanoic acid is 5 to 14% by mass, and the ratio of n-octanoic acid, n-decanoic acid and n-dodecanoic acid to the total amount of the medium-chain fatty acids. The triglyceride having a total of 100% by mass.
[6] A triglyceride containing a medium-chain fatty acid as a constituent fatty acid, wherein the proportion of n-octanoic acid in the total amount of the medium-chain fatty acid constituting the triglyceride is 5 to 15% by mass, and that of n-decanoic acid. The ratio is 75 to 85% by mass, the ratio of n-dodecanoic acid is 5 to 14% by mass, and the ratio of n-octanoic acid, n-decanoic acid and n-dodecanoic acid to the total amount of the medium-chain fatty acids. The triglyceride having a total of 100% by mass.
[7] The proportion of n-octanoic acid in the total amount of the medium-chain fatty acid is 10% by mass, the proportion of n-decanoic acid is 80% by mass, and the proportion of n-dodecanoic acid is 10% by mass. , [5] or [6].
[8] The triglyceride according to any one of [1] to [7], wherein the constituent fatty acid is only a medium chain fatty acid.
[9] The triglyceride according to any one of [1] to [8], wherein the triglyceride comprises a mixture of tricapryrin, tricaprin and / or trilaurin.
[10] Among triglycerides containing medium-chain fatty acids as constituent fatty acids, the proportion of n-octanoic acid in the total amount of the medium-chain fatty acids constituting the triglyceride is 11 to 24% by mass, and the proportion of n-decanoic acid is 76 to A method for improving the cold resistance of the triglyceride by adjusting the content to 89% by mass.
[11] Among triglycerides containing medium-chain fatty acids as constituent fatty acids, the proportion of n-decanoic acid in the total amount of the medium-chain fatty acids constituting the triglyceride is 91 to 99% by mass, and the proportion of n-dodecanoic acid is 1 to 1. A method for improving the cold resistance of the triglyceride by adjusting the content to 9% by mass.
[12] Among triglycerides containing medium-chain fatty acids as constituent fatty acids, the proportion of n-octanoic acid in the total amount of the medium-chain fatty acids constituting the triglyceride is 1 to 25% by mass, and the proportion of n-decanoic acid is 75 to 25. 90% by mass, the ratio of n-dodecanoic acid is 5 to 14% by mass (however, the total ratio of n-octanoic acid, n-decanoic acid and n-dodecanoic acid to the total amount of the medium-chain fatty acid is 100% by mass. A method for improving the cold resistance of the triglyceride.
本発明によれば、室温（２０℃）において固化又は結晶化しにくく、耐冷性に優れた、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドを提供することができる。これにより、これまで固化しやすく、又は結晶が析出しやすかった、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドを、例えば、乳化食品などの一部の食品形態においても使用しやすくなる。また、本発明では、何らの添加剤を加えることなく、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合、ｎ−デカン酸の割合及び／又はｎ−ドデカン酸の割合を特定の数値範囲となるように調整するだけでよいため、中鎖脂肪酸の栄養学的な利点を活かしつつ、使い勝手の良い該トリグリセリドを提供することができる。
さらに、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドは、食品のみならず、化粧品や医薬品の原料としても使用されるため、耐冷性に優れたものが得られれば、その使用用途がさらに拡大することが期待できる。
According to the present invention, it is possible to provide a triglyceride containing a medium-chain fatty acid as a constituent fatty acid, which is difficult to solidify or crystallize at room temperature (20 ° C.) and has excellent cold resistance. This makes it easier to use triglycerides containing medium-chain fatty acids as constituent fatty acids, which have been easily solidified or crystals are easily precipitated, in some food forms such as emulsified foods. Further, in the present invention, the ratio of n-octanoic acid, the ratio of n-decanoic acid and / or the ratio of n-dodecanoic acid to the total amount of the medium-chain fatty acids constituting the triglyceride without adding any additive. Since it is only necessary to adjust the amount to a specific numerical range, it is possible to provide the triglyceride that is easy to use while taking advantage of the nutritional advantages of medium-chain fatty acids.
Furthermore, triglycerides containing medium-chain fatty acids as constituent fatty acids are used not only as foodstuffs but also as raw materials for cosmetics and pharmaceuticals. Therefore, if a product having excellent cold resistance is obtained, its use will be further expanded. Can be expected.
本発明の一態様は、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合、ｎ−デカン酸の割合及び／又はｎ−ドデカン酸の割合が特定の数値範囲になっていることを特徴とする。以下、詳しく説明する。
［構成脂肪酸として中鎖脂肪酸を含有するトリグリセリド］
本発明において、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリド（以下、「ＭＴＧ」とも表す）とは、中鎖脂肪酸を構成脂肪酸の一部もしくは全部とするトリグリセリドを意味する。構成脂肪酸のすべてが中鎖脂肪酸であるトリグリセリドは、中鎖脂肪酸トリグリセリド（以下、「ＭＣＴ」とも表す）といい、ＭＴＧの中に含まれる。また、本発明において、中鎖脂肪酸とは、炭素数８〜１２の脂肪酸であり、直鎖の飽和脂肪酸であることが好ましい。具体的には、ｎ−オクタン酸（カプリル酸）、ｎ−デカン酸（カプリン酸）、ｎ−ドデカン酸（ラウリン酸）である。
また、本発明において、構成脂肪酸は中鎖脂肪酸のみであることが好ましく、具体的には、構成脂肪酸は、ｎ−オクタン酸、ｎ−デカン酸、ｎ−ドデカン酸のみであることが好ましい。
One aspect of the present invention is a triglyceride containing a medium-chain fatty acid as a constituent fatty acid, and the ratio of n-octanoic acid, the ratio of n-decanoic acid, and / or the total amount of the medium-chain fatty acids constituting the triglyceride. It is characterized in that the ratio of n-dodecanoic acid is in a specific numerical range. The details will be described below.
[Triglyceride containing medium-chain fatty acid as constituent fatty acid]
In the present invention, the triglyceride containing a medium-chain fatty acid as a constituent fatty acid (hereinafter, also referred to as "MTG") means a triglyceride in which the medium-chain fatty acid is a part or all of the constituent fatty acids. Triglycerides in which all of the constituent fatty acids are medium-chain fatty acids are referred to as medium-chain fatty acid triglycerides (hereinafter, also referred to as "MCT") and are contained in MTG. Further, in the present invention, the medium-chain fatty acid is a fatty acid having 8 to 12 carbon atoms, and is preferably a straight-chain saturated fatty acid. Specifically, they are n-octanoic acid (caprylic acid), n-decanoic acid (caprylic acid), and n-dodecanoic acid (lauric acid).
Further, in the present invention, the constituent fatty acids are preferably only medium-chain fatty acids, and specifically, the constituent fatty acids are preferably n-octanoic acid, n-decanoic acid, and n-dodecanoic acid only.
本発明において、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が１１〜２４質量％であり、ｎ−デカン酸の割合が７６〜８９質量％であれば、室温（２０℃）における耐冷性が向上するので好ましい。また、ｎ−オクタン酸の割合が１２〜２３質量％であり、ｎ−デカン酸の割合が７７〜８８であることがより好ましく、ｎ−オクタン酸の割合が１５〜２２質量％であり、ｎ−デカン酸の割合が７８〜８５質量％であることがさらに好ましく、ｎ−オクタン酸の割合が２０質量％であり、ｎ−デカン酸の割合が８０質量％であることが殊更好ましい。 In the present invention, a triglyceride containing a medium-chain fatty acid as a constituent fatty acid, wherein the proportion of n-octanoic acid in the total amount of the medium-chain fatty acid constituting the triglyceride is 11 to 24% by mass, and n-decanoic acid. When the ratio of is 76 to 89% by mass, the cold resistance at room temperature (20 ° C.) is improved, which is preferable. Further, the ratio of n-octanoic acid is 12 to 23% by mass, the ratio of n-decanoic acid is more preferably 77 to 88, the ratio of n-octanoic acid is 15 to 22% by mass, and n. The proportion of −decanoic acid is more preferably 78 to 85% by mass, the proportion of n-octanoic acid is 20% by mass, and the proportion of n-decanoic acid is even more preferably 80% by mass.
別の態様では、本発明において、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−デカン酸の割合が９１〜９９質量％であり、ｎ−ドデカン酸の割合が１〜９質量％であれば、室温（２０℃）における耐冷性が向上するので好ましい。また、ｎ−デカン酸の割合が９２〜９８質量％であり、ｎ−ドデカン酸の割合が２〜８質量％であることがより好ましく、ｎ−デカン酸の割合が９３〜９６質量％であり、ｎ−ドデカン酸の割合が４〜７質量％であることがさらに好ましく、ｎ−デカン酸の割合が９５質量％であり、ｎ−ドデカン酸の割合が５質量％であることが殊更好ましい。 In another aspect, in the present invention, the triglyceride containing a medium-chain fatty acid as a constituent fatty acid, and the ratio of n-decanoic acid to the total amount of the medium-chain fatty acid constituting the triglyceride is 91 to 99% by mass. When the ratio of n-dodecanoic acid is 1 to 9% by mass, the cold resistance at room temperature (20 ° C.) is improved, which is preferable. Further, the ratio of n-decanoic acid is 92 to 98% by mass, the ratio of n-dodecanoic acid is more preferably 2 to 8% by mass, and the ratio of n-decanoic acid is 93 to 96% by mass. , The proportion of n-dodecanoic acid is more preferably 4 to 7% by mass, the proportion of n-decanoic acid is 95% by mass, and the proportion of n-dodecanoic acid is particularly preferably 5% by mass.
さらに別の態様では、本発明において、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が１〜２５質量％であり、ｎ−デカン酸の割合が７５〜９０質量％であり、ｎ−ドデカン酸の割合が５〜１４質量％であれば、室温（２０℃）における耐冷性が向上するので好ましい（なお、前記中鎖脂肪酸の全量に占めるｎ−オクタン酸、ｎ−デカン酸およびｎ−ドデカン酸の割合の総計は１００質量％である。以下同様。）。また、ｎ−オクタン酸の割合が４〜２０質量％であり、ｎ−デカン酸の割合が７７〜８６質量％であり、ｎ−ドデカン酸の割合が７〜１３質量％であることがより好ましく、ｎ−オクタン酸の割合が７〜１５質量％であり、ｎ−デカン酸の割合が７８〜８３質量％であり、ｎ−ドデカン酸の割合が８〜１２質量％であることがさらに好ましい。 In still another aspect, in the present invention, a triglyceride containing a medium-chain fatty acid as a constituent fatty acid, wherein the ratio of n-octanoic acid to the total amount of the medium-chain fatty acid constituting the triglyceride is 1 to 25% by mass. If the ratio of n-decanoic acid is 75 to 90% by mass and the ratio of n-dodecanoic acid is 5 to 14% by mass, the cold resistance at room temperature (20 ° C.) is improved, which is preferable (note that the above). The total ratio of n-octanoic acid, n-decanoic acid and n-dodecanoic acid to the total amount of medium-chain fatty acids is 100% by mass. The same shall apply hereinafter). Further, it is more preferable that the ratio of n-octanoic acid is 4 to 20% by mass, the ratio of n-decanoic acid is 77 to 86% by mass, and the ratio of n-dodecanoic acid is 7 to 13% by mass. , N-octanoic acid is 7 to 15% by mass, n-decanoic acid is 78 to 83% by mass, and n-dodecanoic acid is 8 to 12% by mass.
また、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が５〜１５質量％であり、ｎ−デカン酸の割合が７５〜８５質量％であり、ｎ−ドデカン酸の割合が５〜１４質量％であれば、室温（２０℃）における耐冷性が向上するので好ましい（なお、前記中鎖脂肪酸の全量に占めるｎ−オクタン酸、ｎ−デカン酸およびｎ−ドデカン酸の割合の総計は１００質量％である。以下同様。）。また、ｎ−オクタン酸の割合が６〜１４質量％であり、ｎ−デカン酸の割合が７６〜８４質量％であり、ｎ−ドデカン酸の割合が６〜１３質量％であることがより好ましく、ｎ−オクタン酸の割合が７〜１３質量％であり、ｎ−デカン酸の割合が７７〜８３質量％であり、ｎ−ドデカン酸の割合が７〜１２質量％であることがさらに好ましく、ｎ−オクタン酸の割合は８〜１２質量％であり、ｎ−デカン酸の割合が７８〜８２質量％であり、ｎ−ドデカン酸の割合が８〜１１質量％であることが殊更好ましく、ｎ−オクタン酸の割合は１０質量％であり、ｎ−デカン酸の割合が８０質量％であり、ｎ−ドデカン酸の割合が１０質量％であることが最も好ましい。 Further, it is a triglyceride containing a medium-chain fatty acid as a constituent fatty acid, and the proportion of n-octanoic acid in the total amount of the medium-chain fatty acid constituting the triglyceride is 5 to 15% by mass, and the proportion of n-decanoic acid. Is 75 to 85% by mass, and the proportion of n-dodecanoic acid is 5 to 14% by mass, which is preferable because the cold resistance at room temperature (20 ° C.) is improved (note that n accounts for the total amount of the medium-chain fatty acid). The total ratio of −octanoic acid, n-decanoic acid and n-dodecanoic acid is 100% by mass; the same shall apply hereinafter). Further, it is more preferable that the ratio of n-octanoic acid is 6 to 14% by mass, the ratio of n-decanoic acid is 76 to 84% by mass, and the ratio of n-dodecanoic acid is 6 to 13% by mass. , N-octanoic acid is 7 to 13% by mass, n-decanoic acid is 77 to 83% by mass, and n-dodecanoic acid is 7 to 12% by mass, more preferably. The proportion of n-octanoic acid is 8 to 12% by mass, the proportion of n-decanoic acid is 78 to 82% by mass, and the proportion of n-dodecanoic acid is 8 to 11% by mass, more preferably n. Most preferably, the proportion of −octanoic acid is 10% by mass, the proportion of n-decanoic acid is 80% by mass, and the proportion of n-dodecanoic acid is 10% by mass.
本発明で使用される構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドは、従来公知の方法で製造できる。例えば、ｎ−デカン酸（必要に応じて他の脂肪酸も含み得る）とグリセロールとを、触媒下、好ましくは無触媒下、また、好ましくは減圧下で、５０〜２５０℃、より好ましくは１２０〜１８０℃に加熱し、脱水縮合させること（エステル合成）により製造できる。
ここで、触媒としては、特に限定されるものではなく、例えば、通常のエステル合成に用いられる酸触媒又は塩基触媒等を使用することができる。減圧下とは、例えば、０．０１〜１００Ｐａ、好ましくは、０．０５〜７５Ｐａ、より好ましくは、０．１〜５０Ｐａである。このとき系内の水分は少ない方が好ましく、更に好ましくは０．２質量％以下である。
The triglyceride containing a medium-chain fatty acid as a constituent fatty acid used in the present invention can be produced by a conventionally known method. For example, n-decanoic acid (which may also contain other fatty acids if desired) and glycerol are catalyzed, preferably uncatalyzed, and preferably under reduced pressure, at 50-250 ° C, more preferably 120-. It can be produced by heating to 180 ° C. and dehydrating and condensing (ester synthesis).
Here, the catalyst is not particularly limited, and for example, an acid catalyst or a base catalyst used in ordinary ester synthesis can be used. Under reduced pressure is, for example, 0.01 to 100 Pa, preferably 0.05 to 75 Pa, and more preferably 0.1 to 50 Pa. At this time, it is preferable that the water content in the system is small, and more preferably 0.2% by mass or less.
本発明の構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドは（ＭＴＧ）は、また、中鎖脂肪酸及び長鎖脂肪酸を含有するトリグリセリド（以下、「ＭＬＣＴ」とも表す）であってもよい。ＭＬＣＴは、グリセロールに結合する３個の脂肪酸のうち、中鎖脂肪酸と長鎖脂肪酸とがそれぞれ少なくとも１個結合したトリグリセリドである。ここで、長鎖脂肪酸とは、炭素数が１４以上の脂肪酸であり、直鎖脂肪酸であることが好ましい。具体的には、ミリスチン酸、パルミチン酸、ステアリン酸、アラキン酸、ベヘン酸、パルミトオレイン酸、オレイン酸、リノール酸、リノレン酸等が挙げられる。ＭＬＣＴを構成する長鎖脂肪酸は、長鎖脂肪酸の全量に占める不飽和脂肪酸の含有量が７０〜１００質量％（より好ましくは８０〜１００質量％）であることが好ましい。 The triglyceride (MTG) containing a medium-chain fatty acid as a constituent fatty acid of the present invention may also be a triglyceride containing a medium-chain fatty acid and a long-chain fatty acid (hereinafter, also referred to as “MLCT”). MLCT is a triglyceride in which at least one medium-chain fatty acid and one long-chain fatty acid are bound to each of the three fatty acids bound to glycerol. Here, the long-chain fatty acid is a fatty acid having 14 or more carbon atoms, and is preferably a straight-chain fatty acid. Specific examples thereof include myristic acid, palmitic acid, stearic acid, araquinic acid, behenic acid, palmitooleic acid, oleic acid, linoleic acid, and linolenic acid. The long-chain fatty acid constituting the MLCT preferably has an unsaturated fatty acid content of 70 to 100% by mass (more preferably 80 to 100% by mass) in the total amount of the long-chain fatty acid.
上記ＭＬＣＴは、ＭＣＴと同様に、エステル合成により製造されてもよい。ＭＬＣＴは、また、ＭＣＴと長鎖脂肪酸トリグリセリド（以下、「ＬＣＴ」とも表す）の混合物をエステル交換することにより製造されてもよい。ここで、ＬＣＴとは、構成脂肪酸のすべてが長鎖脂肪酸であるトリグリセリドである。ＬＣＴとしては、構成脂肪酸に占める不飽和脂肪酸の含有量が７０質量％以上である油脂が好ましい。
上記ＭＣＴとＬＣＴの混合物のエステル交換は、ＭＣＴとＬＣＴとが、質量比で１０：９０〜９０：１０（より好ましくは２０：８０〜８０：２０）の割合で混合された混合物のエステル交換であることが好ましい。エステル交換する方法としては、特に限定されるものではなく、ナトリウムメトキシドを触媒とした化学的エステル交換や、リパーゼを触媒とした酵素的エステル交換など、通常行われる方法でよい。
The MLCT may be produced by ester synthesis as in the case of MCT. MLCT may also be produced by transesterifying a mixture of MCT and long chain fatty acid triglyceride (hereinafter, also referred to as "LCT"). Here, the LCT is a triglyceride in which all of the constituent fatty acids are long-chain fatty acids. As the LCT, fats and oils in which the content of unsaturated fatty acids in the constituent fatty acids is 70% by mass or more are preferable.
The transesterification of the mixture of MCT and LCT is a transesterification of the mixture of MCT and LCT mixed at a mass ratio of 10:90 to 90:10 (more preferably 20:80 to 80:20). It is preferable to have. The method for transesterification is not particularly limited, and usual methods such as sodium methoxide-catalyzed chemical transesterification and lipase-catalyzed enzymatic transesterification may be used.
［トリグリセリドの耐冷性を向上させる方法］
構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドにおいて、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合、ｎ−デカン酸の割合及び／又はｎ−ドデカン酸の割合が特定の数値範囲にすると、耐冷性が向上することから、本発明は、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドにおいて、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合を１１〜２４質量、ｎ−オクタン酸の割合を７６〜８９質量％とすることにより、前記トリグリセリドの耐冷性を向上させる方法にも関する。
また、別の態様では、本発明は、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドにおいて、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−デカン酸の割合を９１〜９９質量％、ｎ−ドデカン酸の割合を１〜９質量％とすることにより、前記トリグリセリドの耐冷性を向上させる方法にも関する。
さらに、別の態様では、本発明は、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドにおいて、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合を１〜２５質量％、ｎ−デカン酸の割合を７５〜９０質量％、ｎ−ドデカン酸の割合を５〜２５質量％（ただし、前記中鎖脂肪酸の全量に占めるｎ−オクタン酸、ｎ−デカン酸およびｎ−ドデカン酸の割合の総計は１００質量％である。）とすることにより、前記トリグリセリドの耐冷性を向上させる方法にも関する。
なお、本明細書において、「耐冷性」とは、一旦、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドを溶解した後、室温（２０℃）で１０日間保存した場合であっても、固化又は結晶化状態にならず、清澄状態を維持していることをいう。
[How to improve the cold resistance of triglyceride]
Among triglycerides containing medium-chain fatty acids as constituent fatty acids, the proportion of n-octanoic acid, the proportion of n-decanoic acid, and / or the proportion of n-dodecanoic acid in the total amount of the medium-chain fatty acids constituting the triglyceride is specific. In the numerical range, the cold resistance is improved. Therefore, in the present invention, in the triglyceride containing the medium-chain fatty acid as the constituent fatty acid, the ratio of n-octanoic acid to the total amount of the medium-chain fatty acid constituting the triglyceride is 11. It also relates to a method for improving the cold resistance of the triglyceride by setting the ratio of n-octanoic acid to 76 to 89% by mass to 24% by mass.
In another aspect, in the present invention, in the triglyceride containing a medium-chain fatty acid as a constituent fatty acid, the ratio of n-decanoic acid to the total amount of the medium-chain fatty acid constituting the triglyceride is 91 to 99% by mass, n. It also relates to a method for improving the cold resistance of the triglyceride by setting the ratio of -dodecanoic acid to 1 to 9% by mass.
Further, in another aspect, in the triglyceride containing a medium-chain fatty acid as a constituent fatty acid, the ratio of n-octanoic acid to the total amount of the medium-chain fatty acid constituting the triglyceride is 1 to 25% by mass, n. -Decanic acid ratio is 75 to 90% by mass, n-dodecanoic acid ratio is 5 to 25% by mass (however, of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total amount of the medium-chain fatty acids. The total ratio is 100% by mass.) It also relates to a method for improving the cold resistance of the triglyceride.
In the present specification, "cold resistance" means solidification or crystallization even when triglyceride containing a medium-chain fatty acid as a constituent fatty acid is once dissolved and then stored at room temperature (20 ° C.) for 10 days. It means that it does not become a crystallized state and maintains a clear state.
構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドにおいて、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合、ｎ−デカン酸の割合及び／又はｎ−ドデカン酸の割合を特定の数値範囲になるように調整する方法は、従来公知の方法を用いることができる。例えば、市販されているトリカプリリン（トリカプリル酸グリセロール）、トリカプリン（トリカプリン酸グリセロール）、トリラウリン（トリラウリン酸グリセロール）を適当量混合して、特定の数値範囲になるように調整することができる。また、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドをエステル合成する際に、原料となるｎ−オクタン酸、ｎ−デカン酸、ｎ−ドデカン酸を適当量混合することにより、特定の数値範囲になるように調整することができる。
なお、トリグリセリドの耐冷性を向上させる方法において、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリド、前記トリグリセリドを構成する中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合、ｎ−デカン酸の割合及び／又はｎ−ドデカン酸の割合等については、上述で定義したとおりである。
Among triglycerides containing medium-chain fatty acids as constituent fatty acids, the ratio of n-octanoic acid, the ratio of n-decanoic acid and / or the ratio of n-dodecanoic acid to the total amount of the medium-chain fatty acids constituting the triglyceride is specified. As a method for adjusting so as to be within the numerical range, a conventionally known method can be used. For example, commercially available tricapriline (glycerol tricaprylate), tricaprin (glycerol tricaprate), and trilaurin (glycerol trilaurate) can be mixed in appropriate amounts and adjusted to a specific numerical range. Further, when an ester synthesis of a triglyceride containing a medium-chain fatty acid as a constituent fatty acid is performed, an appropriate amount of n-octanoic acid, n-decanoic acid, and n-dodecanoic acid, which are raw materials, is mixed to obtain a specific numerical range. Can be adjusted as follows.
In the method for improving the cold resistance of triglyceride, a triglyceride containing a medium-chain fatty acid as a constituent fatty acid, a ratio of n-octanoic acid, a ratio of n-decanoic acid, and a ratio of n-decanoic acid to the total amount of the medium-chain fatty acids constituting the triglyceride. / Or the ratio of n-dodecanoic acid and the like are as defined above.
次に、実施例及び比較例を挙げ、本発明を更に詳しく説明する。本発明はこれらに何ら制限されるものではない。 Next, the present invention will be described in more detail with reference to Examples and Comparative Examples. The present invention is not limited to these.
以下において「％」とは、特別な記載がない場合、質量％を意味する。
油脂に含まれるトリアシルグリセロールの組成の分析は、ガスクロマトグラフ法（ＪＡＯＣＳ，ｖｏｌ７０，１１，１１１１−１１１４（１９９３）準拠）を用いて行った。
油脂に含まれるトリアシルグリセロール（ＴＡＧ）の有する構成脂肪酸の分析は、ガスクロマトグラフ法（ＡＯＣＳ Ｃｅ１ｆ−９６準拠）を用いて行った。
In the following, "%" means mass% unless otherwise specified.
The composition of triacylglycerol contained in fats and oils was analyzed by gas chromatography (based on JAOCS, vol70, 11, 1111-1114 (1993)).
The constituent fatty acids of triacylglycerol (TAG) contained in fats and oils were analyzed by gas chromatography (based on AOCS Ce1f-96).
＜原料油脂＞
（１）構成脂肪酸として中鎖脂肪酸を含有するトリグリセリド
ＭＣＴ１（日清オイリオグループ株式会社製、商品名：スコレー８（構成脂肪酸がｎ−オクタン酸のみであるトリグリセリド：トリカプリリン）、融点９〜１０℃）
ＭＣＴ２（日清オイリオグループ株式会社製、ラボ調製品（構成脂肪酸がｎ−デカン酸のみであるトリグリセリド：トリカプリン）、融点３１〜３２℃）
ＭＣＴ３（日清オイリオグループ株式会社製、ラボ調製品（構成脂肪酸がｎ−ドデカン酸のみであるトリグリセリド：トリラウリン）、融点４６〜４７℃）
<Raw material fats and oils>
(1) Triglyceride MCT1 containing medium-chain fatty acid as a constituent fatty acid (manufactured by Nisshin Oillio Group Co., Ltd., trade name: Scola 8 (triglyceride having only n-octanoic acid as a constituent fatty acid: tricaprylin), melting point 9 to 10 ° C. )
MCT2 (manufactured by Nisshin Oillio Group Co., Ltd., laboratory preparation (triglyceride containing only n-decanoic acid: tricaprin), melting point 31-32 ° C)
MCT3 (manufactured by Nisshin Oillio Group Co., Ltd., laboratory preparation (triglyceride containing only n-dodecanoic acid: trilaurin), melting point 46-47 ° C)
＜トリグリセリドの配合比率及び目視による固化状態の結果＞
下記表１に示した配合比率で、ＭＣＴ１、ＭＣＴ２およびＭＣＴ３を合計５０ｇ（グラム）となるように５０ｍｌ（ミリリットル）のサンプル瓶の中に加えて混合し、実施例１〜３のトリグリセリド、比較例１〜１２のトリグリセリドを調製した。
なお、実施例１〜３、比較例１〜１２のトリグリセリドは、構成脂肪酸として中鎖脂肪酸を含有するトリグリセリドであって、前記トリグリセリドを構成する中鎖脂肪酸の全量に占めるｎ−オクタン酸の割合、ｎ−デカン酸の割合、及び／又はｎ−ドデカン酸の割合が、前記配合比率と同じ値になっているトリグリセリドである。
また、上記のごとく調製したトリグリセリドを８０℃で一旦溶解（清澄化）した後、徐冷で２０℃の恒温装置にて０日間、３日間、５日間、１０日間保存して、目視により固化状態（清澄のままであるか、固化又は結晶化しているか）をそれぞれ測定した。以上の結果を表１〜３に記した（なお、表１には、１０日後の目視による固化状態の結果のみを●で示し、表２〜３には、上記０日〜１０日後の目視による固化状態の結果を示した）。
なお、上述したように、ＭＣＴ２は融点が３１〜３２℃なので、ＭＣＴ２を５０質量％以上の配合比率で含む、表１のトリグリセリドは、２０℃で１０日間保存した場合、清澄状態から固化又は結晶化状態になることが予測される。
<Results of triglyceride compounding ratio and visual solidification state>
MCT1, MCT2 and MCT3 were added to and mixed in a 50 ml (milliliter) sample bottle so as to have a total of 50 g (grams) at the blending ratios shown in Table 1 below, and the triglycerides of Examples 1 to 3 and Comparative Examples were mixed. 1-12 triglycerides were prepared.
The triglycerides of Examples 1 to 3 and Comparative Examples 1 to 12 are triglycerides containing a medium-chain fatty acid as a constituent fatty acid, and the ratio of n-octanoic acid to the total amount of the medium-chain fatty acids constituting the triglyceride. A triglyceride in which the ratio of n-decanoic acid and / or the ratio of n-dodecanoic acid is the same as the above-mentioned compounding ratio.
In addition, the triglyceride prepared as described above is once dissolved (clarified) at 80 ° C., then slowly cooled and stored in a constant temperature device at 20 ° C. for 0 days, 3 days, 5 days, 10 days, and visually solidified. (Whether it remains clear, solidified or crystallized) was measured respectively. The above results are shown in Tables 1 to 3 (Note that Table 1 shows only the results of the state of solidification by visual inspection after 10 days, and Tables 2 to 3 show the results by visual inspection after 0 to 10 days. The result of the solidified state is shown).
As described above, since MCT2 has a melting point of 31 to 32 ° C., the triglycerides in Table 1 containing MCT2 in a blending ratio of 50% by mass or more are solidified or crystallized from a clarified state when stored at 20 ° C. for 10 days. It is predicted that it will be in a state of crystallization.
表１〜３に示したように、実施例１〜３に示した特定の配合比率においては、予想に反して意外にも、清澄（透明で液状）を維持する現象が見られた。一方、比較例１〜１２の配合比率では、予想通り、固化もしくは結晶化する現象が見られたことから、実施例１〜３の配合比率及びその周辺の配合比率においては、２０℃で１０日間保存しても清澄性を維持することが期待できる。そして、このような清澄状態のトリグリセリドは、様々な食品形態や医薬品及び化粧品等に幅広く応用することができる。 As shown in Tables 1 to 3, unexpectedly, a phenomenon of maintaining clarity (transparent and liquid) was observed at the specific compounding ratios shown in Examples 1 to 3. On the other hand, in the compounding ratios of Comparative Examples 1 to 12, as expected, a phenomenon of solidification or crystallization was observed. It can be expected to maintain clarity even when stored. And, such a triglyceride in a clarified state can be widely applied to various food forms, pharmaceuticals, cosmetics and the like.
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