JP2814676B2 - Oil for confectionery - Google Patents
Oil for confectioneryInfo
- Publication number
- JP2814676B2 JP2814676B2 JP2081157A JP8115790A JP2814676B2 JP 2814676 B2 JP2814676 B2 JP 2814676B2 JP 2081157 A JP2081157 A JP 2081157A JP 8115790 A JP8115790 A JP 8115790A JP 2814676 B2 JP2814676 B2 JP 2814676B2
- Authority
- JP
- Japan
- Prior art keywords
- oil
- fats
- fat
- oils
- reaction
- 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.)
- Expired - Lifetime
Links
- 235000009508 confectionery Nutrition 0.000 title description 3
- 235000019197 fats Nutrition 0.000 claims description 59
- 102000004882 Lipase Human genes 0.000 claims description 23
- 108090001060 Lipase Proteins 0.000 claims description 23
- 239000004367 Lipase Substances 0.000 claims description 23
- 235000019421 lipase Nutrition 0.000 claims description 23
- 238000002844 melting Methods 0.000 claims description 19
- 230000008018 melting Effects 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 17
- 238000005809 transesterification reaction Methods 0.000 claims description 17
- 235000019860 lauric fat Nutrition 0.000 claims description 5
- 235000019841 confectionery fat Nutrition 0.000 claims description 3
- 239000003921 oil Substances 0.000 description 67
- 235000019198 oils Nutrition 0.000 description 66
- 239000003925 fat Substances 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 16
- 244000299461 Theobroma cacao Species 0.000 description 15
- 235000019219 chocolate Nutrition 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 4
- 241000235527 Rhizopus Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 235000009470 Theobroma cacao Nutrition 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 235000019482 Palm oil Nutrition 0.000 description 3
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 3
- 235000008429 bread Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229940110456 cocoa butter Drugs 0.000 description 3
- 235000019868 cocoa butter Nutrition 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- 239000002540 palm oil Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000005496 tempering Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- 241000228212 Aspergillus Species 0.000 description 2
- 241000223198 Humicola Species 0.000 description 2
- 108010093096 Immobilized Enzymes Proteins 0.000 description 2
- 235000021314 Palmitic acid Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 238000004455 differential thermal analysis Methods 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- -1 meltability Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
- 235000019865 palm kernel oil Nutrition 0.000 description 2
- 230000000630 rising effect Effects 0.000 description 2
- 235000020183 skimmed milk Nutrition 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- 240000000064 Penicillium roqueforti Species 0.000 description 1
- 235000002233 Penicillium roqueforti Nutrition 0.000 description 1
- 241000588264 Rhizopus javanicus Species 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- 239000002199 base oil Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000004332 deodorization Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000003248 enzyme activator Substances 0.000 description 1
- 235000013341 fat substitute Nutrition 0.000 description 1
- 239000003778 fat substitute Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 102200004779 rs2232775 Human genes 0.000 description 1
- 102220229106 rs753340463 Human genes 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 238000004808 supercritical fluid chromatography Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000006227 trimethylsilylation reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
Landscapes
- Confectionery (AREA)
- Edible Oils And Fats (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【発明の詳細な説明】 ［産業上の利用分野］ 本発明は酵素で改質した油脂のチョコレート類など菓
子類への利用に適した油脂に関する。Description: FIELD OF THE INVENTION The present invention relates to fats and oils suitable for use in confectionery such as chocolates and the like using fats and oils modified with enzymes.
［従来技術および問題点］ チョコレート等製菓用油脂の代表的なものとして口ど
け性の良いカカオ脂が知られている。カカオ脂の代用油
脂の製造方法といてエステル交換技術を応用する方法が
ある。その一つは反応特異性を持つリパーゼ、すなわ
ち、1,3−位置特異性リパーゼを用い、２−位置にオレ
イン酸を多量に持つ油脂、例えば、オリーブ油、ハイオ
レイックサフラワー油、ハイオレイックサンフラワー油
などとステアリン酸、パルミチン酸などを反応させて構
造的にカカオ脂（トリグリライド）類似のトリグリセラ
イドを得る方法が知られている（特開昭52−104506、特
開昭56−127094、特公昭57−6480、特開昭57−78496、
特公昭57−28519等）。他にヤシ油やパーム油などのラ
ウリン酸系油脂を他の油脂と化学的にエステル交換を行
なわせて物性的に口どけ性の良い油脂を得る方法である
（特開昭52−78203、特開昭55−60599、特開昭60−2314
9、USP2726158、USP2783151等）。[Prior Art and Problems] Cocoa butter having good mouth-drying properties is known as a typical fat and oil for confectionery such as chocolate. There is a method of applying a transesterification technique as a method for producing an oil and fat substitute for cocoa butter. One is a lipase having reaction specificity, that is, a lipase having 1,3-position specificity, and a fat having a large amount of oleic acid at a 2-position, such as olive oil, high oleic safflower oil, high oleic. A method of obtaining a triglyceride structurally similar to cocoa butter (triglylide) by reacting stearic acid, palmitic acid, or the like with sunflower oil or the like is known (JP-A-52-104506, JP-A-56-127094, JP-B-57-6480, JP-A-57-78496,
JP-B-57-28519, etc.). Another method is to chemically transesterify lauric oils and fats such as coconut oil and palm oil with other oils and fats to obtain fats and oils with good physical properties (JP-A-52-78203; Kaisho 55-60599, JP-A-60-2314
9, USP2726158, USP2783151, etc.).
1,3−位置特異性リパーゼを用い、オレイン酸リッチ
の油脂と脂肪酸をエステル交換する方法では、ステアリ
ン酸、パルミチン酸を多量に使用するため、例えば、油
脂：脂肪酸＝1:3の場合には、油脂１を得るために４倍
のスケールの設備が必要であると言うように非常に大き
な設備が必要である。またエステル交換反応して生成し
てくるオレイン酸、反応系に加えた過剰分の脂肪酸など
反応系に加えたのと等量の脂肪酸を反応系から除去、回
収しなければならないため、設備に多額の費用を必要と
する。In the method of transesterifying fatty acids and fatty acids rich in oleic acid using 1,3-regiospecific lipase, a large amount of stearic acid and palmitic acid is used. In order to obtain the fats and oils 1, very large facilities are required. In addition, the same amount of fatty acid as added to the reaction system, such as oleic acid generated by the transesterification reaction and excess fatty acid added to the reaction system, must be removed and recovered from the reaction system. Need cost.
また、触媒としてナトリウムメチラート粉末をノルマ
ルヘキサンに懸濁させて加える方法などを用いるラウリ
ン系油脂と他の油脂との化学的エステル交換反応による
方法はランダムなエステル交換反応である。この場合、
反応系から触媒の除去のため、反応液を水で水洗する必
要があり、その際に加水分解が避けられず、脂肪酸、モ
ノグリセライド、ジグリセライドを副生する。通常の油
脂の精製過程では脂肪酸を除くことはできるが、モノグ
リセライド、ジグリセライドは残留物として油脂中に残
り、油脂の融解性、固体脂含量（以下SFCと略す）、結
晶性等の油脂の物性に悪い影響を及ぼす。Further, a method based on a chemical transesterification reaction between a lauric oil and other fats and oils using a method in which sodium methylate powder is suspended in normal hexane and added as a catalyst is a random transesterification reaction. in this case,
In order to remove the catalyst from the reaction system, it is necessary to wash the reaction solution with water. In this case, hydrolysis is inevitable, and fatty acids, monoglycerides, and diglycerides are by-produced. Fatty acids can be removed during the normal fat and oil refining process, but monoglycerides and diglycerides remain in the fats and oils as residues, and the properties of the fats and oils such as meltability, solid fat content (hereinafter abbreviated as SFC), crystallinity, etc. Have a bad effect.
また原料油脂として、水添脂を用いた場合は、水添臭
特有の臭気が残り、特に日本人には好まれない。Further, when hydrogenated fat is used as a raw material fat, an odor peculiar to hydrogenated odor remains and is not particularly preferred by Japanese.
［発明が解決しようとする課題］ 本発明の課題はラウリン系油脂と他の油脂から融解性
（シャープメルティング性）の優れた、品質の良い製菓
用油脂を得ることである。シャープメルティング性の優
れた油脂を得るにはエステル交換反応において、モノグ
リセライド、ジグリセライドの生成を抑えることであ
る。また、最近はくせのない（例えば、におい、風味
等）油脂が求められている。従って、水添臭がしないほ
うが良い。[Problems to be Solved by the Invention] An object of the present invention is to obtain high-quality confectionery fats and oils having excellent melting properties (sharp melting properties) from lauric fats and fats. In order to obtain an oil and fat having excellent sharp melting properties, it is necessary to suppress the production of monoglyceride and diglyceride in the transesterification reaction. Recently, there is a demand for a habitless fat (eg, smell, flavor, etc.). Therefore, it is better not to have a hydrogenated odor.
［課題を解決するための手段］ 上記課題を達成するためにラウリン系油脂（分別油、
水添油を含む）とその他の油脂の混合物を1,3−位置特
異性リパーゼを用いるエステル交換法によるシャープメ
ルティング性の優れた油脂を得ることができた。すなわ
ち、油脂中の水分が200PPM以下、好ましくは100PPM以下
の微水分系で1,3−位置特異性リパーゼを用いて、選択
的エステル交換反応を行なうことによって、原料混合物
よりはもちろんのこと化学的エステル交換反応生成物よ
りも優れた物性を有する油脂を得ることができた。微水
分系で、位置特異性酵素を用いることによって、加水分
解を抑えることができ、脂肪酸、モノグリセライド、ジ
グリセライドを実質的に含有しない油脂を得ることがで
きた。モノグリセライド、ジグリセライドを実質的に含
有しないため、シャープメルティング性の優れた油脂が
得られた。また、原料に水添脂を用いた場合には、同様
の反応を行なうことによって、水添臭の消失した、ある
いは、非常に弱められた油脂を得ることができた。[Means for Solving the Problems] In order to achieve the above objects, lauric fats and oils (fractionated oil,
A mixture of hydrogenated oil (including hydrogenated oil) and other fats and oils could be obtained by a transesterification method using 1,3-regiospecific lipase to obtain a fat and oil excellent in sharp melting property. That is, by performing a selective transesterification reaction using a 1,3-regiospecific lipase in a slightly water system in which the water content of the fat or oil is 200 PPM or less, preferably 100 PPM or less, it is possible to perform a chemical reaction as well as a raw material mixture. Fats and oils having better properties than the transesterification reaction product could be obtained. By using a regiospecific enzyme in a slightly water system, hydrolysis could be suppressed, and an oil or fat substantially free of fatty acids, monoglycerides and diglycerides could be obtained. Since substantially no monoglyceride or diglyceride was contained, an oil or fat having excellent sharp melting properties was obtained. When hydrogenated fat was used as a raw material, a similar reaction was carried out, whereby a fat or oil with no hydrogenated odor or extremely weakened could be obtained.
原料の油脂の種類や配合比率を種々変更することによ
って、シャープメルティング性の優れた、種々の融点の
油脂を得ることができた。これらの油脂はノーテンパリ
ング型のカカオ代替脂として優れた性質を示した。By variously changing the kind and the mixing ratio of the raw material fats and oils, it was possible to obtain fats and oils having various melting points and excellent sharp melting properties. These fats and oils exhibited excellent properties as no-tempering type cocoa substitute fats.
本発明で用いるリパーゼとして、リゾープス属（Rhiz
opus）、アスペルギルス属（Aspergillus）、ムコール
属（Mucol）、フミコーラ属（Humicola）、ペニシリウ
ム属（Penicillium）由来のリパーゼなどを用いること
ができる。具体的には、天野製薬（株）が販売している
次のリパーゼを用いることができる。すなわち、Rhizop
us delemer由来の「リパーゼＤ」（商品名、以下同
じ）、Rhizopus javanicus由来の「リパーゼＦ−AP1
5］、Rhizopus niger由来の「リパーゼAP」、Mucor j
avanicus由来の「リパーゼＭ−AP」、Humicola lanugi
nosa由来の「リパーゼCE」、Penicillium roqueforti
由来の「リパーゼＲ−20」などである。As the lipase used in the present invention, the genus Rhizopus (Rhiz
opus), lipases derived from Aspergillus, Aspergillus, Mucol, Humicola, Penicillium, and the like. Specifically, the following lipases sold by Amano Pharmaceutical Co., Ltd. can be used. That is, Rhizop
“lipase D” (trade name, the same applies hereinafter) derived from us delemer, and “lipase F-AP1 derived from Rhizopus javanicus”
5], “Lipase AP” from Rhizopus niger, Mucor j
"Lipase M-AP" from avanicus, Humicola lanugi
"lipase CE" from nosa, Penicillium roqueforti
"Lipase R-20" and the like.
また、本発明で用いることのできるラウリン系油脂と
しては、ヤシ油、パーム核油、ババス核油、ツクム油な
ど構成脂肪酸がラウシン酸主体の油脂であり、これらの
油脂の種々の水添脂、分別油または水添脂と分別脂とを
配合した混合脂などを用いることができる。その他の油
脂としては、パーム油、パーム水添脂、大豆油、大豆水
添脂、牛脂、ラードなどあらゆる動物油脂、植物油脂お
よびそれらの水添脂、分別油脂などを用いることができ
る。The lauric fats and oils that can be used in the present invention include coconut oil, palm kernel oil, Babas kernel oil, and constituent fatty acids such as tsucum oil, which are mainly lauric acid, and various hydrogenated fats and oils of these fats and oils. Separated oil or mixed fat obtained by mixing hydrogenated fat and fractionated fat can be used. As other fats and oils, all animal fats and oils such as palm oil, palm hydrogenated fat, soybean oil, soybean fat, beef tallow, lard, vegetable fats and oils, and hydrogenated fats, fractionated fats and the like can be used.
本発明の選択的エステル交換反応は次の様に行なう。
反応に使用するリパーゼをレシチンなどの酵素活性化剤
と共に水にとかしてセライトやイオン交換樹脂などの担
体に固定化し・乾燥し、固定化酵素を調製する。この固
定化酵素剤をカラムに充填し、油脂中の水分200PPM以
下、好ましくは100PPM以下に乾燥した混合油脂（基質）
を30〜60℃で連続的にカラムに流して、反応を行なう。
なお、この反応は連続的でなく、バッチ方式で行なって
もよい。The selective transesterification of the present invention is carried out as follows.
The lipase used in the reaction is dissolved in water together with an enzyme activator such as lecithin and immobilized on a carrier such as celite or ion exchange resin and dried to prepare an immobilized enzyme. A mixed oil (substrate) filled with this immobilized enzyme agent in a column and dried to a water content of 200 PPM or less, preferably 100 PPM or less, in the oil or fat
Is passed through the column continuously at 30 to 60 ° C. to carry out the reaction.
This reaction may be performed not in a continuous manner but in a batch system.
実施例１ Rhizopus delemer由来のリパーゼ（天野製薬（株）
商品名「リパーゼＤ」26.6gと精製粉末大豆レシチン8
gを水350mlに溶かし、担体として1000gの陽イオン交換
樹脂「WK−13」（三菱化成（株）製）に加え、約30分間
よく撹拌し、担体の表面にリパーゼが均一にコーティン
グした。リパーゼが均一にコーティングされたセライト
を40℃、60mmHg以下で16〜18時間乾燥処理し、固定化リ
パーゼを調製した。この固定化リパーゼには水分を約１
％を含んでいた。反応基質として、パーム核極硬（パー
ム核極度硬化油の略）とパーム極硬（パーム極度硬化油
の略）を5:1の比率で混合したものを減圧乾燥し、水分
を50PPMに調整した。固定化リパーゼ300gを内径10cm、
長さ50cmのカラムに充填して、カラム全体を60℃に保っ
た。上記の混合原料油脂を60℃に加温し、ポンプで毎分
5gを定量的にカラムに流し、60℃で連続的に酵素反応を
行なった。カラムを通過した反応生成物に２重量％の活
性白土を加えて80℃、20分間20mmHgの減圧下に撹拌した
後、50℃保温下に自然濾過を行ない、脱色油を得た。Example 1 Lipase derived from Rhizopus delemer (Amano Pharmaceutical Co., Ltd.)
Product name "Lipase D" 26.6g and purified soybean lecithin 8
g was dissolved in 350 ml of water, added to 1000 g of a cation exchange resin "WK-13" (manufactured by Mitsubishi Chemical Corporation) as a carrier, and stirred well for about 30 minutes to uniformly coat the surface of the carrier with lipase. Celite coated with lipase uniformly was dried at 40 ° C. and 60 mmHg or less for 16 to 18 hours to prepare immobilized lipase. The immobilized lipase contains about 1
%. As a reaction substrate, a mixture of palm core hardened (abbreviated palm hardened oil) and palm hardened hard (abbreviated palm hardened oil) at a ratio of 5: 1 was dried under reduced pressure to adjust the water content to 50 PPM. . Immobilized lipase 300 g inner diameter 10 cm,
The column was packed in a 50 cm long column and the entire column was kept at 60 ° C. Heat the above mixed raw material fats and oils to 60 ° C and pump it every minute
5 g was quantitatively passed through the column, and the enzyme reaction was continuously performed at 60 ° C. After adding 2% by weight of activated clay to the reaction product passed through the column, the mixture was stirred at 80 ° C. for 20 minutes under a reduced pressure of 20 mmHg, followed by natural filtration while keeping the temperature at 50 ° C. to obtain a decolorized oil.
得られた脱色油を220℃、40分間、2mmHg、吹込み水蒸
気量2.6重量％で真空水蒸気蒸留（脱臭）を行なって精
製油を得た。エステル交換率100％の反応生成物の精製
油について物性を測定し、その結果を表１、図１及び図
２に示した。The resulting decolorized oil was subjected to vacuum steam distillation (deodorization) at 220 ° C. for 40 minutes, 2 mmHg, and a blown steam amount of 2.6% by weight to obtain a purified oil. Physical properties of the purified oil of the reaction product having a transesterification rate of 100% were measured, and the results are shown in Table 1, FIG. 1 and FIG.
その結果、モノグリセリド、ジグリセリドなど副生物
の少ない、上昇融点38.8℃の、原料油に比べて著しく融
解性が改良された（シャープメルティング性の優れ
た）、しかも水添臭の消失した油脂を得ることができ
た。その結果を図１および図２に示した。As a result, fats and oils with little by-products such as monoglyceride and diglyceride, with a rising melting point of 38.8 ° C, with remarkably improved meltability (excellent sharp melting property) as compared with the base oil, and with no hydrogenated odor are obtained. I was able to. The results are shown in FIGS.
なお、エステル交換率とは反応によって炭素数別組成
比の変化の大きなトリグリセリドに関し、反応前と反応
終了時（組成比の経時変化が平衡に達したところ）の変
化量を（組成％の差）エステル交換率100％とし、それ
に対する反応物の変化量の割合を意味する。また各物性
の測定方法は次の様に行なった。The transesterification rate refers to the amount of change before and after the end of the reaction (where the change in the composition ratio over time reaches equilibrium) with respect to the triglyceride having a large change in the composition ratio depending on the number of carbon atoms due to the reaction (the difference in the composition%). The transesterification rate is defined as 100%, and the ratio of the change amount of the reactant to the transesterification rate is meant. The measuring method of each physical property was performed as follows.
上昇融点:0℃１時間テンパリングした後常法によって
測定した。Rising melting point: Measured by an ordinary method after tempering for 1 hour at 0 ° C.
モノグリセリド、ジグリセリド：油脂をトリメチルシ
リル化し、ガスクロマトグラムを用いて行なった。Monoglyceride, diglyceride: Trimethylsilylation of fats and oils was performed using a gas chromatogram.
固体脂含量（SFC）:PRAXIS MODEL SFC−900を用い
て10℃、21.1℃、26.7℃、33.3℃、37.8℃のSFCを求め
た。Solid fat content (SFC): SFCs at 10 ° C, 21.1 ° C, 26.7 ° C, 33.3 ° C, and 37.8 ° C were determined using PRAXIS MODEL SFC-900.
示差熱分析（DSC）：初温度100℃から毎分10℃づつ低
下させ、−100℃に達したところで昇温（毎分10℃）
し、吸熱パターンを測定した。Differential thermal analysis (DSC): Decrease by 10 ° C per minute from the initial temperature of 100 ° C, and when it reaches -100 ° C, raise the temperature (10 ° C per minute)
Then, the endothermic pattern was measured.
比較例１ 実施例１と同じ組成の原料配合油400gを乾燥後（脱水
後）800mlの３ツ口フラスコにとり、0.8gのナトリウム
メチラートを5mlのｎ−ヘキサンに懸濁して加え、80℃
に加熱保温下で30分間撹拌し、エステル交換を行なっ
た。次いで水40mlを加え、さらに10分間撹拌し、エステ
ル交換反応を停止した。反応液を遠心分離機に付し、反
応停止に用いた水を分離した。反応生成液について実施
例１と同様に脱色、脱臭して精製油を得た。エステル交
換率100％の反応生成物の精製油について、実施例１と
同様の物性値を測定し、その結果を表１、図１および図
２に示した。この油脂はシャープメルティング性を示す
が、副生物のジグリセリドが比較的多く残存し、SFCが
チョコレート用油脂としてやや低く、水添臭も残った。Comparative Example 1 400 g of the raw material blended oil having the same composition as in Example 1 was dried (after dehydration), placed in an 800 ml three-necked flask, and 0.8 g of sodium methylate was suspended in 5 ml of n-hexane and added.
The mixture was stirred for 30 minutes while keeping the temperature under heat to carry out transesterification. Then, 40 ml of water was added, and the mixture was further stirred for 10 minutes to stop the transesterification reaction. The reaction solution was centrifuged to separate water used for stopping the reaction. The reaction product was decolorized and deodorized in the same manner as in Example 1 to obtain a purified oil. Physical properties similar to those in Example 1 were measured for the purified oil of the reaction product having a transesterification rate of 100%, and the results are shown in Table 1, FIG. 1 and FIG. Although this fat and oil showed sharp melting properties, a relatively large amount of diglyceride as a by-product remained, the SFC was slightly lower as fat for chocolate, and a hydrogenated odor remained.
実施例２ 実施例１によって得た精製油脂を下記の比率で配合
し、ロールで磨砕・混合し、さらにコンチングし、テン
パリング（温調）をすることなく成型固化し、板チョコ
レートを得た。 Example 2 The refined fats and oils obtained in Example 1 were blended at the following ratio, ground and mixed by a roll, further conched, and solidified without tempering (temperature control) to obtain a plate chocolate.
板チョコレートの配合： 実施例１で得た精製油脂 300g ココアパウダー 90 粉 糖 180 脱脂粉乳 30 また、コンチング後のチョコレート溶融物を48℃に保
ち、パンを浸したパンコーティングのテストを行なっ
た。Formulation of chocolate plate: 300 g of the purified fat or oil obtained in Example 1 cocoa powder 90 powder sugar 180 skim milk powder 30 Further, the chocolate melt after conching was kept at 48 ° C., and a bread coating test in which bread was dipped was performed.
比較例２ 比較例１によって得たエステル交換油脂を実施例２と
同様の条件で精製し、実施例２と同様の配合で、同様の
板チョコレートを調製しパンコーティングテストを行な
った。Comparative Example 2 The transesterified oil and fat obtained in Comparative Example 1 was purified under the same conditions as in Example 2, and the same composition as in Example 2 was used to prepare the same plate chocolate, and a pan coating test was performed.
その結果、実施例２は原料油脂及び比較例２に比べて
硬さ、口どけ性、味、風味等が良好な板チョコレート、
乾きが早く、垂れ程度、硬さ等良好なパンコーティング
チョコレートであることが判明した。As a result, Example 2 had a hardness, mouth-drying property, taste, and plate chocolate that were favorable in comparison with the raw material fat and oil and Comparative Example 2,
It was found that the bread-coated chocolate dries quickly and has good dripping degree and hardness.
実施例３ パーム核油とパーム油の比率が4:1の混合物を実施例
で用いた1,3−位置特異性酵素を、実施例１と同様の条
件で用いて得た酵素改質油脂を実施例１と同様の方法で
精製し、その物性を測定した。上昇融点は24.7℃でSFC
およびDSCパターンからシャープメルティング性である
ことが判明した。すなわち低融点のシャープメルテイン
グ性油脂が得らた（図示せず）。 Example 3 Enzyme-modified fats and oils obtained by using a 1,3-regiospecific enzyme using a mixture of palm kernel oil and palm oil at a ratio of 4: 1 in the examples under the same conditions as in Example 1 Purification was performed in the same manner as in Example 1, and the physical properties were measured. SFC at 24.7 ° C
And it was found from the DSC pattern that it had sharp melting properties. That is, a low melting point sharp melting oil was obtained (not shown).
実施例４ 実施例３で得た油脂40g、ココアパウダー27g、粉砂糖
54g、脱脂粉乳9gを配合し、ロールで磨砕混合した後さ
らに実施例３で得た油脂170gを加えてコンチング（精
練）した。Example 4 40 g of the oil and fat obtained in Example 3, 27 g of cocoa powder, powdered sugar
54 g and 9 g of skim milk powder were blended, and the mixture was ground and mixed with a roll, and then 170 g of the fat or oil obtained in Example 3 was further added thereto for conching (scouring).
コンチング後のチョコレート溶融物を40℃に保ち、こ
れにアイスバーを浸してコーティングテストを行なっ
た。その結果、乾きが速く、ひび割れのない歯ざわりの
良好なアイスコーティングチョコレートであることが判
明した。The chocolate melt after conching was kept at 40 ° C., and an ice bar was immersed in the melt to perform a coating test. As a result, it was found that the ice-coated chocolate dries quickly and has good texture without cracks.
［発明の効果］ 本発明により油脂は、原料の油脂組成を代えることに
より、種々の融点においてシャープメルティング性を有
する油脂が得られる。天然物では得られないような温度
のシャープメルティングな油脂が得られたり、また高価
なカカオ油脂と同等な性能を有する油脂が安価に得られ
る。これらのシャープメルティングな油脂を含有する高
性能な製菓用油脂組成物が得られる。 [Effects of the Invention] According to the present invention, fats and oils having sharp melting properties at various melting points can be obtained by changing the composition of the fat or oil as a raw material. It is possible to obtain sharp melting fats and oils at a temperature that cannot be obtained with natural products, and to obtain inexpensively fats and oils having performance equivalent to expensive cocoa fats and oils. A high-performance confectionery fat / oil composition containing these sharp-melting fats / oils is obtained.
図１は油脂のSFC（固体脂含量）と温度との関係を示
し、縦軸はSFC（％）、横軸は温度を示す。また図２は
油脂のDSC（示差熱分析）パターンを示す。FIG. 1 shows the relationship between the SFC (solid fat content) of oils and fats and temperature, the vertical axis shows SFC (%), and the horizontal axis shows temperature. FIG. 2 shows a DSC (differential thermal analysis) pattern of the fat or oil.
フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) A23D 9/00 500 A23G 1/00 C12P 7/64Continuation of front page (58) Field surveyed (Int.Cl. 6 , DB name) A23D 9/00 500 A23G 1/00 C12P 7/64
Claims (1)
脂とその他の油脂との混合物を1,3−位置特異性リパー
ゼを用い、選択的エステル交換反応によって得られるシ
ャープメルティング性を有する製菓用油脂1. A confectionery fat or oil having a sharp melting property obtained by selective transesterification of a lauric fat or a mixture of a lauric fat and another fat with a 1,3-regiospecific lipase.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2081157A JP2814676B2 (en) | 1990-03-30 | 1990-03-30 | Oil for confectionery |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2081157A JP2814676B2 (en) | 1990-03-30 | 1990-03-30 | Oil for confectionery |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03280830A JPH03280830A (en) | 1991-12-11 |
| JP2814676B2 true JP2814676B2 (en) | 1998-10-27 |
Family
ID=13738609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2081157A Expired - Lifetime JP2814676B2 (en) | 1990-03-30 | 1990-03-30 | Oil for confectionery |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2814676B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3388838B2 (en) * | 1993-11-18 | 2003-03-24 | 旭電化工業株式会社 | Method for producing fat composition for confectionery |
| JP5216277B2 (en) * | 2007-08-22 | 2013-06-19 | 株式会社カネカ | Method for producing edible fats and oils |
-
1990
- 1990-03-30 JP JP2081157A patent/JP2814676B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03280830A (en) | 1991-12-11 |
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