JP2018115284A - Solidifying or crystalline triglyceride - Google Patents
Solidifying or crystalline triglyceride Download PDFInfo
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- JP2018115284A JP2018115284A JP2017008161A JP2017008161A JP2018115284A JP 2018115284 A JP2018115284 A JP 2018115284A JP 2017008161 A JP2017008161 A JP 2017008161A JP 2017008161 A JP2017008161 A JP 2017008161A JP 2018115284 A JP2018115284 A JP 2018115284A
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- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims abstract description 74
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims abstract description 136
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims abstract description 128
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims abstract description 124
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 57
- 229930195729 fatty acid Natural products 0.000 claims abstract description 57
- 239000000194 fatty acid Substances 0.000 claims abstract description 57
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 57
- 239000000470 constituent Substances 0.000 claims abstract description 48
- 238000007711 solidification Methods 0.000 claims abstract description 22
- 230000008023 solidification Effects 0.000 claims abstract description 22
- 150000004667 medium chain fatty acids Chemical class 0.000 claims description 89
- 150000003626 triacylglycerols Chemical class 0.000 claims description 29
- VMPHSYLJUKZBJJ-UHFFFAOYSA-N trilaurin Chemical compound CCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCC)COC(=O)CCCCCCCCCCC VMPHSYLJUKZBJJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 6
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims description 5
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims description 5
- 229940093633 tricaprin Drugs 0.000 claims description 4
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- 238000000034 method Methods 0.000 abstract description 12
- 230000002708 enhancing effect Effects 0.000 abstract 1
- 235000013305 food Nutrition 0.000 description 10
- 102100034068 Monocarboxylate transporter 1 Human genes 0.000 description 9
- 238000002156 mixing Methods 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 150000004668 long chain fatty acids Chemical class 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- 101710137760 Malonyl-CoA-acyl carrier protein transacylase, mitochondrial Proteins 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 101000937642 Homo sapiens Malonyl-CoA-acyl carrier protein transacylase, mitochondrial Proteins 0.000 description 4
- 101000590830 Homo sapiens Monocarboxylate transporter 1 Proteins 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 125000005457 triglyceride group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- 101000577115 Homo sapiens Monocarboxylate transporter 2 Proteins 0.000 description 2
- 101000577121 Homo sapiens Monocarboxylate transporter 3 Proteins 0.000 description 2
- 101000577126 Homo sapiens Monocarboxylate transporter 4 Proteins 0.000 description 2
- 102100025272 Monocarboxylate transporter 2 Human genes 0.000 description 2
- 102100025276 Monocarboxylate transporter 4 Human genes 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- -1 medium chain fatty acid triglycerides Chemical class 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- HABLENUWIZGESP-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O.CCCCCCCCCC(O)=O HABLENUWIZGESP-UHFFFAOYSA-N 0.000 description 1
- 235000020880 diabetic diet Nutrition 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 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
- 230000002255 enzymatic effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 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
- 235000019421 lipase Nutrition 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000020855 low-carbohydrate diet Nutrition 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- 235000021590 normal diet Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 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
- 235000021313 oleic acid Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003203 triacylglycerol group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Edible Oils And Fats (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fats And Perfumes (AREA)
Abstract
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、固化性又は結晶性トリグリセリド、及び、該トリグリセリドの固化性又は結晶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, the ratio of n-octanoic acid, the ratio of n-decanoic acid and / or n-dodecane in the total amount of the medium chain fatty acid constituting the triglyceride. The present invention relates to a solidifying or crystalline triglyceride in which the ratio of an acid falls within a specific numerical range, and a method for improving the solidifying or crystallinity 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。 Older people and patients after illness may suffer from malnutrition because they cannot eat enough of their normal diet. In order to cope with such a situation, foods that can be ingested with a small amount of sufficient nutrition have been developed. In particular, when the focus is on energy (calorie) intake, it is more efficient to increase the lipid content of such foods. In addition, in order to obtain a food corresponding to a ketone diet (for example, Patent Document 1), a diabetic diet, and a low carbohydrate diet, it is preferably a high lipid and low carbohydrate.
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に含まれている中鎖脂肪酸は、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。特に、ｎ−オクタン酸は体内でのエネルギーへの変換が速く、効率的である。しかし、ｎ−オクタン酸を構成脂肪酸とするＭＴＧの多くは室温で液状であるため、流動性が高く、一部の食品形態（例えば、粉体状食品）によってはハンドリング性に問題があった。 As lipids used in such foods, triglycerides (hereinafter, also referred to as “MTG”) containing medium chain fatty acids as constituent fatty acids are well known. The medium chain fatty acids contained in MTG are absorbed rapidly in the digestive tract and are decomposed very quickly in the liver to turn into energy, which has a nutritional advantage. In particular, n-octanoic acid is fast and efficient in converting into energy in the body. However, since many MTGs containing n-octanoic acid as a constituent fatty acid are liquid at room temperature, they have high fluidity, and there are problems in handling properties depending on some food forms (for example, powdery foods).
本発明の課題は、室温（２０℃）において固化又は結晶化しやすい、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固化性又は結晶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 easily solidified or crystallized at room temperature (20 ° C.), and a method for improving the solidification or crystallinity of the triglyceride.
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 earnest research to solve the above problems, the present inventor, as a result of triglycerides containing medium chain fatty acids as constituent fatty acids, the proportion of n-octanoic acid in the total amount of medium chain fatty acids constituting the triglycerides, It was found that the problem can be solved by adjusting the ratio of n-decanoic acid and / or the ratio of n-dodecanoic acid within a specific numerical range, and the present invention has been completed.
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８０〜９０質量％であり、ｎ−デカン酸の割合が６〜１４質量％でありｎ−ドデカン酸の割合が１〜１０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。
〔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、８０〜９０質量％であり、ｎ−デカン酸の割合が６〜１４質量％であり、ｎ−ドデカン酸の割合が１〜５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、〔１〕に記載のトリグリセリド。
〔３〕前記中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が８５質量％であり、ｎ−デカン酸の割合が１０質量％であり、ｎ−ドデカン酸の割合が５質量％である、〔１〕又は〔２〕に記載のトリグリセリド。
〔４〕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７５〜９０質量％であり、ｎ−デカン酸の割合が１〜１４質量％であり、ｎ−ドデカン酸の割合が６〜１４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。
〔５〕前記中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が７５〜９０質量％であり、ｎ−デカン酸の割合が１〜１４質量％であり、ｎ−ドデカン酸の割合が６〜１０質量％であり、前記中鎖脂肪酸の全量に占める割合の総計が１００質量％である、〔４〕に記載のトリグリセリド。
〔６〕前記中鎖脂肪酸の全量に占める、ｎ−オクタン酸の割合が８０〜８５質量％であり、ｎ−デカン酸の割合が５〜１０質量％であり、ｎ−ドデカン酸の割合が１０質量％である、〔４〕又は〔５〕に記載のトリグリセリド。
〔７〕前記構成脂肪酸が中鎖脂肪酸のみである、〔１〕ないし〔６〕のいずれか１項に記載のトリグリセリド。
〔８〕前記トリグリセリドが、トリカプリリン、トリカプリン、トリラウリンの混合物からなる、〔１〕ないし〔７〕のいずれか１項に記載のトリグリセリド。
〔９〕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８０〜９０質量％、ｎ−デカン酸の割合を６〜１４質量％、ｎ−ドデカン酸の割合を１〜１０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固化性又は結晶性を向上させる方法。
〔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７５〜９０質量％、ｎ−デカン酸の割合を１〜１４質量％、ｎ−ドデカン酸の割合を６〜１４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固化性又は結晶性を向上させる方法。
That is, the present invention provides the following.
[1] Triglycerides containing medium chain fatty acids as constituent fatty acids, wherein the proportion of n-octanoic acid in the total amount of medium chain fatty acids constituting the triglycerides is 80 to 90% by mass, The ratio is 6 to 14% by mass, the ratio of n-dodecanoic acid is 1 to 10% by mass, and the total ratio of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total amount of the medium chain fatty acids The triglyceride, wherein is 100% by mass.
[2] The ratio of n-octanoic acid in the total amount of the medium chain fatty acid is 80 to 90% by mass, the ratio of n-decanoic acid is 6 to 14% by mass, and the ratio of n-dodecanoic acid is The triglyceride according to [1], which is 1 to 5% by mass, and the total ratio of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total amount of the medium chain fatty acid is 100% by mass.
[3] The proportion of n-octanoic acid in the total amount of the medium chain fatty acid is 85 mass%, the proportion of n-decanoic acid is 10 mass%, and the proportion of n-dodecanoic acid is 5 mass%. , [1] or [2].
[4] Triglycerides containing medium chain fatty acids as constituent fatty acids, wherein the proportion of n-octanoic acid in the total amount of medium chain fatty acids constituting the triglycerides is 75 to 90% by mass, The ratio is 1 to 14% by mass, the ratio of n-dodecanoic acid is 6 to 14% by mass, and the ratio of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total amount of the medium chain fatty acids. The said triglyceride whose sum total is 100 mass%.
[5] The ratio of n-octanoic acid to the total amount of the medium chain fatty acid is 75 to 90% by mass, the ratio of n-decanoic acid is 1 to 14% by mass, and the ratio of n-dodecanoic acid is 6 The triglyceride according to [4], in which the total proportion of the medium chain fatty acid is 100% by mass.
[6] The proportion of n-octanoic acid in the total amount of the medium chain fatty acid is 80 to 85 mass%, the proportion of n-decanoic acid is 5 to 10 mass%, and the proportion of n-dodecanoic acid is 10 The triglyceride according to [4] or [5], which is% by mass.
[7] The triglyceride according to any one of [1] to [6], wherein the constituent fatty acid is only a medium chain fatty acid.
[8] The triglyceride according to any one of [1] to [7], wherein the triglyceride is a mixture of tricaprylin, tricaprin, and trilaurin.
[9] In triglycerides containing medium chain fatty acids as constituent fatty acids, the proportion of n-octanoic acid in the total amount of medium chain fatty acids constituting the triglycerides is 80 to 90% by mass, and the proportion of n-decanoic acid is 6 to 14% by mass, and the proportion of n-dodecanoic acid is 1 to 10% by mass (however, the total proportion of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total amount of the medium chain fatty acid is 100% by mass) A method for improving the solidification or crystallinity of the triglyceride.
[10] In 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 triglycerides is 75 to 90% by mass, and the ratio of n-decanoic acid is 1 to 14 mass%, the ratio of n-dodecanoic acid is 6-14 mass% (however, the total ratio of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total amount of the medium chain fatty acid is 100 mass%) A method for improving the solidification or crystallinity of the triglyceride.
本発明によれば、室温（２０℃）において固化性又は結晶性に優れた、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、これまで液状であり、使い勝手があまり良くなかった、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のハンドリング性を向上させることができ、様々な食品（例えば粉体状食品）に対しても混合しやすくなる。また、本発明では、トリグリセリドを固化又は結晶化させるために、増粘剤などの他の成分を加える必要がなく、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、固化性又は結晶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 excellent in solidification or crystallinity at room temperature (20 ° C.). As a result, the handling properties of triglycerides containing medium-chain fatty acids as constituent fatty acids, which have been liquid and not easy to use, can be improved, and for various foods (for example, powdery foods) Easy to mix. In the present invention, in order to solidify or crystallize the triglyceride, it is not necessary to add other components such as a thickener, and the ratio of n-octanoic acid to the total amount of the medium chain fatty acid constituting the triglyceride, Since it is only necessary to adjust the ratio of n-decanoic acid and / or the ratio of n-dodecanoic acid to be within a specific numerical range, the triglyceride which is easy to use while taking advantage of the nutritional advantages of medium chain fatty acids Can be provided.
Furthermore, triglycerides containing medium chain fatty acids as constituent fatty acids are used not only for foods but also as raw materials for cosmetics and pharmaceuticals. It can be expected to expand.
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, the ratio of n-octanoic acid, the ratio of n-decanoic acid and / or the total amount of the medium chain fatty acid constituting the triglyceride. The ratio of n-dodecanoic acid is in a specific numerical range. This will be described in detail below.
[Triglycerides containing medium chain fatty acids as constituent fatty acids]
In the present invention, a triglyceride containing medium chain fatty acid as a constituent fatty acid (hereinafter also referred to as “MTG”) means a triglyceride having the medium chain fatty acid as a part or all of the constituent fatty acid. Triglycerides in which all of the constituent fatty acids are medium chain fatty acids are called medium chain fatty acid triglycerides (hereinafter also referred to as “MCT”), and are included in MTG. Moreover, in this invention, a medium chain fatty acid is a C8-C12 fatty acid, and it is preferable that it is a linear saturated fatty acid. Specifically, n-octanoic acid (caprylic acid), n-decanoic acid (capric acid), and n-dodecanoic acid (lauric acid).
In the present invention, the constituent fatty acid is preferably only a medium chain fatty acid, and specifically, the constituent fatty acid is preferably only n-octanoic acid, n-decanoic acid, and n-dodecanoic acid.
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８０〜９０質量％であり、ｎ−デカン酸の割合が６〜１４質量％であり、ｎ−ドデカン酸の割合が１〜１０質量％であれば、室温（２０℃）における固化性又は結晶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。以下のいずれの場合も同様。）。また、ｎ−オクタン酸の割合が８２〜８８質量％であり、ｎ−デカン酸の割合が７〜１２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−オクタン酸の割合が８３〜８７質量％であり、ｎ−デカン酸の割合が８〜１２質量％であり、ｎ−ドデカン酸の割合が３〜６質量％であることがさらに好ましい。 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 80 to 90% by mass, and n-decanoic acid Is preferably 6 to 14% by mass and n-dodecanoic acid is 1 to 10% by mass because the solidification or crystallinity at room temperature (20 ° C.) is improved. The total of the proportions of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total amount of is 100% by mass (the same applies in any of the following cases). Moreover, it is more preferable that the ratio of n-octanoic acid is 82-88 mass%, the ratio of n-decanoic acid is 7-12 mass%, and the ratio of n-dodecanoic acid is 2-8 mass%. More preferably, the ratio of n-octanoic acid is 83 to 87 mass%, the ratio of n-decanoic acid is 8 to 12 mass%, and the ratio of n-dodecanoic acid is 3 to 6 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８０〜９０質量％であり、ｎ−デカン酸の割合が６〜１４質量％であり、ｎ−ドデカン酸の割合が１〜５質量％であれば、室温（２０℃）における固化性又は結晶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。以下のいずれの場合も同様。）。また、ｎ−オクタン酸の割合が８２〜８８質量％であり、ｎ−デカン酸の割合が７〜１２質量％であり、ｎ−ドデカン酸の割合が２〜５質量％であることがより好ましく、ｎ−オクタン酸の割合が８３〜８７質量％であり、ｎ−デカン酸の割合が８〜１２質量％であり、ｎ−ドデカン酸の割合が３〜５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８５質量％であり、ｎ−デカン酸の割合が１０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。 Moreover, 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 80 to 90% by mass, and the proportion of n-decanoic acid 6 to 14% by mass and the ratio of n-dodecanoic acid is preferably 1 to 5% by mass because the solidification or crystallinity at room temperature (20 ° C.) is improved (the total amount of the medium-chain fatty acids). The total of the proportions of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total is 100% by mass (the same applies in any of the following cases). Moreover, it is more preferable that the ratio of n-octanoic acid is 82-88 mass%, the ratio of n-decanoic acid is 7-12 mass%, and the ratio of n-dodecanoic acid is 2-5 mass%. More preferably, the ratio of n-octanoic acid is 83 to 87 mass%, the ratio of n-decanoic acid is 8 to 12 mass%, and the ratio of n-dodecanoic acid is 3 to 5 mass%, It is particularly preferable that the ratio of n-octanoic acid is 85% by mass, the ratio of n-decanoic acid is 10% by mass, and the ratio of n-dodecanoic acid is 5% 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−オクタン酸の割合が７５〜９０質量％であり、ｎ−デカン酸の割合が１〜１４質量％であり、ｎ−ドデカン酸の割合が６〜１４質量％であれば、室温（２０℃）における固化性又は結晶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。以下のいずれの場合も同様。）。また、ｎ−オクタン酸の割合が７７〜８８質量％であり、ｎ−デカン酸の割合が３〜１２質量％であり、ｎ−ドデカン酸の割合が７〜１２質量％であることがより好ましく、ｎ−オクタン酸の割合が７９〜８６質量％であり、ｎ−デカン酸の割合が４〜１１質量％であり、ｎ−ドデカン酸の割合が８〜１１質量％であることがさらに好ましい。 In another aspect, in the present invention, 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 75 to 90% by mass. When the ratio of n-decanoic acid is 1 to 14% by mass and the ratio of n-dodecanoic acid is 6 to 14% by mass, the solidification or crystallinity at room temperature (20 ° C.) is improved. The total ratio of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total amount of the medium chain fatty acid is 100% by mass. Moreover, it is more preferable that the ratio of n-octanoic acid is 77 to 88 mass%, the ratio of n-decanoic acid is 3 to 12 mass%, and the ratio of n-dodecanoic acid is 7 to 12 mass%. More preferably, the ratio of n-octanoic acid is 79 to 86% by mass, the ratio of n-decanoic acid is 4 to 11% by mass, and the ratio of n-dodecanoic acid is 8 to 11% 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７５〜９０質量％であり、ｎ−デカン酸の割合が１〜１４質量％であり、ｎ−ドデカン酸の割合が６〜１０質量％であれば、室温（２０℃）における固化性又は結晶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。以下のいずれの場合も同様。）。また、ｎ−オクタン酸の割合が７７〜８８質量％であり、ｎ−デカン酸の割合が３〜１２質量％であり、ｎ−ドデカン酸の割合が７〜１０質量％であることがより好ましく、ｎ−オクタン酸の割合が７９〜８６質量％であり、ｎ−デカン酸の割合が４〜１１質量％であり、ｎ−ドデカン酸の割合が８〜１０質量％であることがさらに好ましい。
加えて、ｎ−オクタン酸の割合が８０〜８５質量％であり、ｎ−デカン酸の割合が５〜１０質量％であり、ｎ−ドデカン酸の割合が１０質量％であることが好ましく、特に、ｎ−オクタン酸の割合が８５質量％であり、ｎ−デカン酸の割合が５質量％であり、ｎ−ドデカン酸の割合が１０質量％であるか、もしくは、ｎ−オクタン酸の割合が８０質量％であり、ｎ−デカン酸の割合が１０質量％であり、ｎ−ドデカン酸の割合が１０質量％であることが好ましい。
Moreover, 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 75 to 90% by mass, and the proportion of n-decanoic acid Is 1 to 14% by mass, and the ratio of n-dodecanoic acid is preferably 6 to 10% by mass because the solidification or crystallinity at room temperature (20 ° C.) is improved (the total amount of the medium chain fatty acids). The total of the proportions of n-octanoic acid, n-decanoic acid and n-dodecanoic acid in the total is 100% by mass (the same applies in any of the following cases). Moreover, it is more preferable that the ratio of n-octanoic acid is 77 to 88 mass%, the ratio of n-decanoic acid is 3 to 12 mass%, and the ratio of n-dodecanoic acid is 7 to 10 mass%. More preferably, the ratio of n-octanoic acid is 79 to 86% by mass, the ratio of n-decanoic acid is 4 to 11% by mass, and the ratio of n-dodecanoic acid is 8 to 10% by mass.
In addition, it is preferable that the ratio of n-octanoic acid is 80 to 85% by mass, the ratio of n-decanoic acid is 5 to 10% by mass, and the ratio of n-dodecanoic acid is 10% by mass, The ratio of n-octanoic acid is 85 mass%, the ratio of n-decanoic acid is 5 mass%, the ratio of n-dodecanoic acid is 10 mass%, or the ratio of n-octanoic acid is It is preferably 80% by mass, the ratio of n-decanoic acid is 10% by mass, and the ratio 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−オクタン酸（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-octanoic acid (which may contain other fatty acids as necessary) and glycerol are added at 50 to 250 ° C., more preferably 120 to 120 ° C. under a catalyst, preferably without a catalyst, and preferably under reduced pressure. It can be produced by heating to 180 ° C. and dehydrating condensation (ester synthesis).
Here, the catalyst is not particularly limited, and for example, an acid catalyst or a base catalyst used for 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, the amount of water in the system is preferably 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 containing medium chain fatty acid as the constituent fatty acid of the present invention (MTG) may also be a triglyceride containing medium chain fatty acid and long chain fatty acid (hereinafter also referred to as “MLCT”). MLCT is a triglyceride in which at least one medium-chain fatty acid and long-chain fatty acid are bonded to each other among the three fatty acids bonded to glycerol. Here, the long chain fatty acid is a fatty acid having 14 or more carbon atoms, and is preferably a linear fatty acid. Specific examples include myristic acid, palmitic acid, stearic acid, arachidic 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 in the total amount of the long-chain fatty acid of 70 to 100% by mass (more preferably 80 to 100% by mass).
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 in the same manner as MCT. MLCT may also be produced by transesterification of a mixture of MCT and long chain fatty acid triglycerides (hereinafter also referred to as “LCT”). Here, LCT is a triglyceride in which all of the constituent fatty acids are long chain fatty acids. As LCT, fats and oils in which the content of unsaturated fatty acids in the constituent fatty acids is 70% by mass or more are preferred.
Transesterification of the mixture of MCT and LCT is transesterification of a mixture in which MCT and LCT are mixed at a mass ratio of 10:90 to 90:10 (more preferably 20:80 to 80:20). Preferably there is. The method for transesterification is not particularly limited, and a commonly performed method such as chemical transesterification using sodium methoxide as a catalyst or enzymatic transesterification using lipase as a catalyst may be used.
［トリグリセリドの固化性又は結晶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、固化性又は結晶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８０〜９０質量％、ｎ−デカン酸の割合を６〜１４質量％、ｎ−ドデカン酸の割合を１〜１０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固化性又は結晶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−オクタン酸の割合を７５〜９０質量％、ｎ−デカン酸の割合を１〜１４質量％、ｎ−ドデカン酸の割合を５〜１５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固化性又は結晶性を向上させる方法にも関する。
なお、本明細書において、「固化性又は結晶性」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、清澄状態から固化又は結晶化状態になることをいう。
[Method for improving solidification or crystallinity of triglyceride]
In the triglyceride containing medium chain fatty acid as a constituent fatty acid, the ratio of n-octanoic acid, the ratio of n-decanoic acid and / or the ratio of n-dodecanoic acid in the total amount of the medium chain fatty acid constituting the triglyceride is specified. Since the solidification or crystallinity is improved in the numerical range, the present invention is a triglyceride containing a medium chain fatty acid as a constituent fatty acid, and the n-octanoic acid accounts for the total amount of the medium chain fatty acid constituting the triglyceride. 80-90% by mass, 6-14% by mass of n-decanoic acid, 1-10% by mass of n-dodecanoic acid (however, n-octanoic acid, n -The total ratio of decanoic acid and n-dodecanoic acid is 100% by mass), thereby improving the solidification or crystallinity of the triglyceride. Also relates to a method.
In another aspect, the present invention relates to 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 75 to 90% by mass, n -The proportion of decanoic acid is 1 to 14% by mass and the proportion of n-dodecanoic acid is 5 to 15% by mass (provided that n-octanoic acid, n-decanoic acid and n-dodecanoic acid account for the total amount of the medium chain fatty acids) (The total ratio is 100% by mass), whereby the solidification or crystallinity of the triglyceride is improved.
In this specification, “solidification or crystallinity” refers to solidification from a clarified state when a triglyceride containing a medium chain fatty acid is dissolved as a constituent fatty acid and then stored at room temperature (20 ° C.) for 10 days. Or, it means to be in a crystallized 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、特定の数値範囲と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、トリグリセリドの固化性又は結晶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。
In the triglyceride containing medium chain fatty acid as a constituent fatty acid, the ratio of n-octanoic acid, the ratio of n-decanoic acid and / or the ratio of n-dodecanoic acid in the total amount of the medium chain fatty acid constituting the triglyceride is specified. A conventionally known method can be used for adjusting the numerical value range. For example, commercially available tricaprylin (glycerol tricaprylate), tricaprin (glycerol tricaprate), and trilaurin (glycerol trilaurate) can be mixed so as to adjust to a specific numerical range. In addition, when synthesizing triglycerides containing medium chain fatty acids as constituent fatty acids, a specific numerical range is obtained by mixing appropriate amounts of n-octanoic acid, n-decanoic acid, and n-dodecanoic acid as raw materials. Can be adjusted as follows.
In the method for improving the solidification or crystallinity of triglycerides, triglycerides containing medium chain fatty acids as constituent fatty acids, the proportion of n-octanoic acid in the total amount of medium chain fatty acids constituting the triglycerides, n-decanoic acid The ratio of and / or the ratio of n-dodecanoic acid 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, an Example and a comparative example are given and this invention is demonstrated in more detail. 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.
Analysis of the composition of triacylglycerol contained in the fats and oils was performed using a gas chromatographic method (based on JAOCS, vol 70, 11, 1111-1114 (1993)).
Analysis of the constituent fatty acid possessed by triacylglycerol (TAG) contained in the fats and oils was performed using a gas chromatographic method (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 oil and fat>
(1) Triglyceride containing medium chain fatty acid as a constituent fatty acid MCT1 (manufactured by Nisshin Oillio Group, trade name: Scoley 8 (triglyceride whose constituent fatty acid is only n-octanoic acid: tricaprylin), melting point 9-10 ° C. )
MCT2 (manufactured by Nissin Oilio Group, Lab preparation (triglyceride whose constituent fatty acid is only n-decanoic acid: tricaprin), melting point 31 to 32 ° C.)
MCT3 (manufactured by Nisshin Oilio Group, Lab-prepared product (triglyceride whose constituent fatty acid is 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１〜１５のトリグリセリドを調製した。
なお、実施例１〜３、比較例１〜１５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、ＭＣＴ１は融点が９〜１０℃なので、ＭＣＴ１を７０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日間保存しても、清澄（透明で液状）状態を保ったままであることが予測される。
<Results of blending ratio of triglyceride and solidified state visually>
In the mixing ratio shown in Table 1 below, MCT1, MCT2 and MCT3 were added to a 50 ml (milliliter) sample bottle so as to be a total of 50 g (grams), and mixed. 1-15 triglycerides were prepared.
The triglycerides of Examples 1 to 3 and Comparative Examples 1 to 15 are triglycerides containing medium chain fatty acids as constituent fatty acids, and the ratio of n-octanoic acid in the total amount of medium chain fatty acids constituting the triglycerides. The ratio of n-decanoic acid and / or the ratio of n-dodecanoic acid is a triglyceride having the same value as the blending ratio.
The triglyceride prepared as described above is once dissolved at 80 ° C. and then stored for 0 days, 3 days, 5 days, 10 days in a constant temperature apparatus at 20 ° C. by gradual cooling. Whether it remains solid, solidified or crystallized). The above results are shown in Tables 1 to 3 (in Table 1, only the results of the solidified state visually after 10 days are indicated by ●, and in Tables 2 to 3 are visually observed after the above 0 days to 10 days. The result of solidification state is shown).
As described above, since MCT1 has a melting point of 9 to 10 ° C., the triglycerides in Table 1 containing MCT1 in a blending ratio of 70% by mass or more can be clarified (clear and liquid even when stored at 20 ° C. for 10 days. ) Is expected to remain in the state.
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、固化又は結晶化する現象が見られた。一方、比較例１〜１５の配合比率では、予想通り、清澄状態を維持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日間保存すると固化又は結晶化することが期待できる。そして、このような固化又は結晶化したトリグリセリドは、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, in the specific blending ratios shown in Examples 1 to 3, unexpectedly, a phenomenon of solidification or crystallization was observed contrary to expectation. On the other hand, in the blending ratios of Comparative Examples 1 to 15, as expected, a phenomenon of maintaining a clear state was observed. It can be expected to solidify or crystallize upon storage. Such solidified or crystallized triglycerides can be widely applied to various food forms, pharmaceuticals, cosmetics, and the like.
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| JP2006306864A (en) * | 2005-03-31 | 2006-11-09 | Suntory Ltd | Lignan compound-containing composition |
| JP2015510010A (en) * | 2012-03-01 | 2015-04-02 | プロメティック・バイオサイエンシーズ・インコーポレイテッドＰｒｏＭｅｔｉｃ ＢｉｏＳｃｉｅｎｃｅｓ Ｉｎｃ． | Method for producing medium-chain fatty acid triglycerides |
| WO2016121675A1 (en) * | 2015-01-26 | 2016-08-04 | 日清オイリオグループ株式会社 | Oil or fat |
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| JP2015510010A (en) * | 2012-03-01 | 2015-04-02 | プロメティック・バイオサイエンシーズ・インコーポレイテッドＰｒｏＭｅｔｉｃ ＢｉｏＳｃｉｅｎｃｅｓ Ｉｎｃ． | Method for producing medium-chain fatty acid triglycerides |
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