JP3569116B2 - Liquid general-purpose fat composition - Google Patents
Liquid general-purpose fat composition Download PDFInfo
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- JP3569116B2 JP3569116B2 JP27882797A JP27882797A JP3569116B2 JP 3569116 B2 JP3569116 B2 JP 3569116B2 JP 27882797 A JP27882797 A JP 27882797A JP 27882797 A JP27882797 A JP 27882797A JP 3569116 B2 JP3569116 B2 JP 3569116B2
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- 239000007788 liquid Substances 0.000 title claims description 45
- 239000000203 mixture Substances 0.000 title claims description 33
- 239000003925 fat Substances 0.000 claims description 105
- 239000003921 oil Substances 0.000 claims description 66
- 235000019198 oils Nutrition 0.000 claims description 66
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 30
- 229930195729 fatty acid Natural products 0.000 claims description 30
- 239000000194 fatty acid Substances 0.000 claims description 30
- 150000004665 fatty acids Chemical class 0.000 claims description 21
- -1 fatty acid ester Chemical class 0.000 claims description 10
- 239000000779 smoke Substances 0.000 claims description 10
- 239000003963 antioxidant agent Substances 0.000 claims description 9
- 235000006708 antioxidants Nutrition 0.000 claims description 9
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 9
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 9
- 239000003549 soybean oil Substances 0.000 claims description 8
- 235000012424 soybean oil Nutrition 0.000 claims description 8
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 6
- 150000004671 saturated fatty acids Chemical class 0.000 claims description 6
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 5
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 5
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- 239000000470 constituent Substances 0.000 claims description 5
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 5
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- 238000009825 accumulation Methods 0.000 description 8
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
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- 150000003626 triacylglycerols Chemical class 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
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- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
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- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 description 1
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Description
【0001】
【発明の属する技術分野】
本発明は、一般に使用されている食用油脂と比較して、食後の血中トリグリセリド(中性脂肪)の増加が抑制され、体への蓄積性が少なく、しかも保存安定性及び風味が良好で汎用性(低温でも液状であって、通常の調理油に代えて使用可能)がある食用油脂組成物に関するものである。
【0002】
【従来の技術】
人は必要なカロリーを主に糖質及び脂質から摂取しているが、現代のようにともすれば栄養の摂取の仕方が偏り、しかも摂取カロリー量が過剰となるような状態では、肥満を助長し、成人病などの問題を引き起こす原因となる。特に近年、先進諸国の食生活においては脂質の摂取量は増大しており、このことは血中トリグリセリド(中性脂肪)濃度の増加、肥満を招き、成人病の大きな原因となっている。血中トリグリセリド(中性脂肪)値及び血中コレステロール値は動脈硬化と密接に関係しているため、これらの値を低く保つことは成人病予防の点で特に大切なことであり、先進諸国においてはこれらの値を低くするよう指導が行われている。しかし、それにもかかわらず実際には循環器系の成人病による死亡者数は増加の一途を辿っている。
これは脂質(油脂)を多く使用した食事はおいしく、しかも現代人はこれら食事に慣れてしまった点に問題がある。実際、脂質摂取量が少なかったはずの日本人においてもこの傾向は現れており、ここ50年で摂取エネルギーにおける脂質の占める割合は3倍に増加している。そのため、これまで脂質摂取量を減らす目的で、蛋白や糖を物性的に油脂に近づけ、低カロリーにした油脂代替物が開発されてきた。しかし、これら代替物は、油脂が有する風味、食感及び物理的特性を完全に代替するには至っていない。しかもこれらは、油脂が有するもう一つの役割である調理時の熱媒体としての役割を代替することは不可能である。そこで、現在使用している油脂と同等の風味、食感及び物理的性質を有し、しかも熱媒体として使用でき、さらに食後の血中トリグリセリド(中性脂肪)増加を抑えることが出来る油脂が開発できれば、肥満を防ぎさらには成人病の発病率を低下させることが可能になると考えられる。
この様な油脂としては近年開発が盛んに行われている非吸収性油脂がある。たとえばショ糖脂肪酸ポリエステル(マットソンら:米国特許第3,600,186号明細書)があり、これは体内で吸収されず排泄されるため油脂由来のカロリーは0となる。しかし、非吸収性の油脂であるため、液体状態の脂肪酸ショ糖ポリエステルは、肛門漏洩、脂溶性ビタミン吸収阻害等の問題を一方で引き起こす。本物質は1996年1月30日、FDAにより使用を許可された。しかし、一定量のビタミンA、D、E及びKを添加した融点が37.8℃〜71.1℃の半固体もしくは固体のショ糖ポリエステルを塩味スナック菓子のみに使用するという限定付きでである。これは脂溶性ビタミン吸収阻害防止及び肛門漏洩防止のためである。このことにより現時点において本油脂代替物は汎用性がないことがわかる。
中鎖脂肪酸トリグリセリド(MCT)は、体内で非蓄積であることが公知のこととして知られている。しかし、加熱調理に使用した際、低い発煙点(160 ℃以下)が問題となり、調理油として使用することは困難である。
【0003】
長鎖飽和脂肪酸(たとえばベヘン酸)及び炭素数10以下の中鎖脂肪酸を含有したトリグリセリド(セイデン:特開平2−1799号公報)及び長鎖飽和脂肪酸(たとえばステアリン酸)及び短鎖脂肪酸を含有したトリグリセリド(クリサム:特表平6−506106号公報)は、生体内で難吸収性の長鎖飽和脂肪酸と体内非蓄積性の中鎖脂肪酸もしくは短鎖脂肪酸を含有しているため、食後の血中トリグリセリド(中性脂肪)増加を抑え、成人病予防用油脂代替物としての使用が期待できるが、性状が固体脂であるため汎用性が乏しくなる。
米国特許第4,976,984号明細書には、リン脂質と5〜100%のジグリセリドを含有するグリセリド混合物とを含有する食用油組成物が開示されている。また、特開平4−300825号公報及び特開平4−300826号公報には、ジグリセリドを有効成分とする血清トリグリセリド濃度低下剤及び体重増加抑制剤が開示されている。
また、特開平8−60180号公報には、構成脂肪酸が長鎖脂肪酸及び中鎖脂肪酸からなるジグリセリドを油脂成分中に含む油脂組成物が開示されている。
【0004】
【発明が解決しようとする課題】
本発明の目的は、従来の油と同等の汎用性(低温でも液状であって、通常の調理油に代えて使用可能)を有しながら、動脈硬化の原因の一つである血中トリグリセリド(中性脂肪)の増加を抑制し、体内への蓄積性が少なく、しかも保存安定性及び風味が良好である食用油脂組成物を提供することである。
【0005】
【課題を解決するための手段】
そこで本発明者らは、上記課題を解決すべく種々検討した結果、油脂中に 1,3−ジグリセリドを40重量%以上、好ましくは45重量%以上、より好ましくは50重量%以上含有し、モノグリセリドを1.5重量%未満、好ましくは1重量%未満含有する油脂組成物であって、且つ油脂中のジグリセリドの構成脂肪酸中、93重量%以上、好ましくは95重量%以上が不飽和脂肪酸である油脂組成物が、通常の食用油より食後の血中トリグリセリド(中性脂肪)の増加が起こりにくく、しかも体脂肪蓄積及び内臓脂肪への蓄積が軽減され、さらに通常の食用油が有するあらゆる用途にも使用出来る液状油脂組成物であることを発見し本発明に至った。
【0006】
【発明の実施の形態】
以下、本発明について詳細に説明する。
1,3−ジグリセリドはトリグリセリド(通常の油脂の構造)と異なり、摂取後、十二指腸で加水分解されると、主に1−モノグリセリドを生じる(トリグリセリドからは2−モノグリセリドが主に生じる)。その結果、小腸上皮細胞でのトリグリセリドの再合成が抑制され、リンパ管中の血中トリグリセリド(中性脂肪)が低下し、体脂肪蓄積及び内臓脂肪への蓄積軽減効果につながる。 1,2−ジグリセリドは十二指腸で分解されると2−モノグリセリドを主に生じるため、このような効果は発揮しない。よって、「血中トリグリセリド(中性脂肪)の増加抑制」、「体脂肪蓄積軽減」及び「内臓脂肪蓄積軽減」という効果を発現するためには、油脂中に40重量%以上の 1,3−ジグリセリドを含有することが必須である。
【0007】
本発明においては、汎用性の液状油脂であるという観点より、用途としては汎用型食用油(例えば調理油)が考えられる。そのため、通常調理が行われる温度(170 ℃)以上の発煙点を有することが好ましい(より好ましくは180 ℃以上、更に好ましくは190 ℃以上)。また風味の点より、油脂組成物中のモノグリセリド含量が1.5重量%未満、好ましくは1重量%未満、酸価(AV)は 1.0以下であることが望ましい。
【0008】
さらに、保存時及び調理時の酸化安定性の点より、抗酸化剤を油脂に対して50〜2000ppm 、特に400 〜1000ppm 添加することが好ましく、天然抗酸化剤、トコフェロール、アスコルビルパルミテート、アスコルビルステアレート、BHT、BHA及びリン脂質等から選ばれる1種類もしくは2種類以上の抗酸化剤の添加が好ましく、特に好ましい例としては、天然抗酸化剤、トコフェロール、アスコルビルパルミテート及びリン脂質等から選ばれる1種類もしくは2種類以上の抗酸化剤がある。アスコルビルパルミテートとトコフェロールの併用が最も好ましい。
【0009】
本油脂組成物の主なる使用目的は汎用型食用油(例えば調理油)であるため、保存状態において結晶生成及び固化が起こっては都合が悪い。このことより、冷蔵庫内で保存した場合、結晶生成及び固化が起こらない条件として、油脂中の 1,3−ジグリセリドの含有量が90重量%以下(好ましくは80重量%以下、より好ましくは75重量%以下)とすることが好ましく、またジグリセリド中の不飽和脂肪酸含有量を93重量%以上、好ましくは95重量%以上とすることが必須となる。
ジグリセリドを構成する脂肪酸の炭素数は12〜24、好ましくは16〜22である。
【0010】
さらに不飽和脂肪酸中のオレイン酸などのモノ不飽和脂肪酸含有量が60重量%以下、好ましくは、50重量%以下であることが望ましい。残部はリノール酸、リノレン酸などの高度不飽和脂肪酸である。
さらに特定するとジグリセリド中の不飽和脂肪酸含有量が93重量%以上、不飽和脂肪酸中のモノ不飽和脂肪酸含有量が60重量%以下である油脂組成物が好ましい。
最も好ましいのはジグリセリド中の不飽和脂肪酸含有量が95重量%以上、不飽和脂肪酸中のオレイン酸含有量が50重量%以下の油脂組成物である。
このような組成の油脂組成物は、例えばナタネ油、大豆油などを加水分解して得た脂肪酸をウインタリングして飽和脂肪酸を除去した脂肪酸を原料とすることにより得ることができる。
また、HLB(それぞれの化合物に適した経験式より求めたHLB値を使用。例えばポリグリセリン脂肪酸エステルならばGriffin の経験式)が4以下、好ましくは3以下の結晶抑制剤(例えば、ポリグリセリン脂肪酸エステル、ショ糖脂肪酸エステル、ソルビタン脂肪酸エステル等)を油脂に対して200 〜5000ppm 、特に500 〜2000ppm 添加し、低温での安定性を改善する方法も好ましい。
【0011】
【実施例】
以下に実施例をもって本発明の効果をより詳細に説明するが、本発明はこれらの例に限定されるものではない。尚、例中の%は特記しない限り重量基準である。
〔油脂の調製〕
固定化1,3位選択的リパーゼである市販リパーゼ製剤(リパーゼ商品名:「Lipozyme 3A 」、ノボインダストリーA.S.社製)を触媒として、ナタネ油由来脂肪酸又は大豆油由来脂肪酸(もしくはウインタリングにより飽和脂肪酸を除去した脂肪酸)およびグリセリンを40℃で反応させた。リパーゼ製剤を濾別した後、反終品を分子蒸留にかけ、常法により精製を行って液状油脂Aを得た。さらに反応時間をコントロールした同様の方法で液状油脂B、液状油脂C、液状油脂F、液状油脂G、液状油脂I及び液状油脂Jを得た。
さらにナタネ油由来脂肪酸に適当量の飽和脂肪酸(パルミチン酸及び/又はステアリン酸)を添加し、同様の方法で液状油脂D及び液状油脂Eを得た。
また、同様の方法で合成した液状油脂をカラムクロマトグラフ(和光純薬工業社製ワコーゲルC−200とヘキサン/エーテル=70/30にてトリグリセリド画分とジグリセリド画分を得た)により脂肪酸画分、モノグリセリド画分を除去し、溶媒を除去することにより液状油脂Hを得た。
【0012】
尚、各油脂のグリセリド組成及びジグリセリドの構成脂肪酸組成は、以下に示す方法により分析した。
・グリセリド組成分布の測定
油脂をシリル化剤(関東化学社製、シリル化剤TH)にてシリル化した後、キャピラリーカラム(例えばJ&W社、DBTM−1)を装備した、水素炎イオン検出器付きのガスクロマトグラフィーにて分析し、そのリテンションタイム及びピーク面積比よりグリセリド組成分布及び 1,3−ジグリセリド含有量を求めた。
・ジグリセリドの構成脂肪酸分析
カラムクロマトグラフ(和光純薬工業社製ワコーゲルC−200とヘキサンでトリグリセリド画分を落とした後、ヘキサン/エーテル=70/30にてジグリセリド画分を得た)により油脂中のジグリセリド画分を集め、その後「日本油化学協会編、基準油脂分析法」中の「2.4.20.2−77 脂肪酸メチルエステルの調整法」、「2.4.21.2−73 脂肪酸組成」の方法に従い、ガスクロマトグラフィーにて分析した。得られたチャートのリテンションタイム及びピークエリア比よりジグリセリド中の脂肪酸分布を求めた。
使用する油脂の組成を表1に示す。また、通常油の組成を表2に示す。
【0013】
【表1】
【0014】
【表2】
【0015】
実施例1
各種油脂10%、牛血清アルブミン2%、卵黄レシチン 0.2%及び蒸留水87.8%を含む混合液を高圧乳化機を用いて乳化し、平均粒径0.25mmの乳剤を得た。本乳剤を18時間絶食させた13週齢SDラットにラット体重 100g当たり0.73mlとなるように経口投与し、各採血時間群(0、0.7 、1.0 、1.7 、3.3 時間)(各群4匹)ごとに採血し、血中トリグリセリド量変化を観察した。結果を表3に示す。
【0016】
【表3】
【0017】
液状油脂A及び液状油脂Bで飼育したラット群は、ナタネ油及び大豆油を投与したラット群と比較し、有意(t<0.01)に血中トリグリセリド(中性脂肪)増加が抑制されており、液状油脂A及び液状油脂Bは、食後の血中トリグリセリド(中性脂肪)増加を抑制する油脂であることがわかる。一方、液状油脂Cは、ナタネ油及び大豆油を投与したラット群と比較し、有意(t<0.01)に血中トリグリセリド(中性脂肪)増加が抑制されなかった。
【0018】
実施例2
各食餌とも6週齢SD系ラットを10匹用い、表4に示す餌をラットに与えて3週間飼育した時の体重変化と体脂肪率変化を表5に示す。なお、体脂肪率の測定は、電導率を利用した小動物用体脂肪率測定装置(EM−SCAN Model SA−2、EM−SCAN社製)を用い、ネンブタール麻酔下で測定することにより行った。
【0019】
【表4】
【0020】
【表5】
【0021】
液状油脂Aで飼育したラット群は、ナタネ油及び大豆油で飼育したラット群と比較し、有意(t<0.01)に体脂肪率が低下し、また、液状油脂Bで飼育したラット群も、ナタネ油及び大豆油で飼育したラット群と比較し、有意(t<0.05)に体脂肪率が低下した。このことから、液状油脂A及び液状油脂Bは、内臓や脂肪組織(脂肪細胞)への脂肪蓄積が小さい油脂であることがわかる。一方、液状油脂Cは、ナタネ油及び大豆油を投与したラット群と比較し、有意に体脂肪率が低下していないことがわかった。
【0022】
実施例3
調理評価により調製油の汎用性を評価した。
新たに調製した油脂の内容を表6に示す。
【0023】
【表6】
【0024】
本油脂組成物の調理油としての評価を、やきそばを作ることにより行った。評価は、調理時における発煙、調理作業性、やきそばの風味と、油っぽさについて、5人によるパネラーで評価する方法によって行った。結果を表7に示した。
・発煙
◎ 発煙全くなし
○ 発煙ほとんどなし
△ 発煙やや有り
× 発煙有り
・調理作業性
◎ 非常に良い
○ よい
△ やや悪い
× 悪い
・風味
◎ 非常に良い
○ よい
△ やや悪い
× 悪い
一人分の材料
液状油脂 30g
豚肉 50g
キャベツ 50g
たけのこ 25g
たまねぎ 25g
しいたけ 15g
中華そば 180g
【0025】
【表7】
【0026】
上記結果より液状油脂1、液状油脂2及び液状油脂5は、発煙が起こらず、調理作業性も良好で、しかも風味も良い油脂で、通常油と同等に使用できる油脂であることがわかった。一方、液状油脂3及び液状油脂4は、風味が悪く、しかも発煙が起こり、炒め物料理には使用できず、しかも風味が悪いことが判明した。
【0027】
実施例4
次にこの油脂を用いて揚げ物料理を行った結果を示す。
調理油としての評価は、下記の材料を用いて天ぷらを作り、そのときの発煙の仕方、調理作業性、風味を5人によるパネラーで評価した(評価基準は実施例3の場合と同じ)。結果を表8に示した。
調理評価に使用した材料
油 300g
海老 2尾
南瓜 2切れ
バッター組成
卵 50g
水 150g
小麦粉 100g
【0028】
【表8】
【0029】
上記結果より、液状油脂1、液状油脂2及び液状油脂5は、発煙が起こらず、調理作業性も良好で、風味も良く、しかも油っぽくない油脂で、通常油と同等に使用できる油脂であることがわかった。一方、液状油脂3及び液状油脂4は、風味が悪く、しかも発煙が起こり、揚げ物料理には使用出来ないことが判明した。
【0030】
実施例5
油脂の低温耐性(結晶生成抑制)を5℃の冷蔵庫中に1週間放置し、その時生成した油脂結晶状態より低温耐性を評価した。結果を表9に示す。
・低温耐性
◎ 結晶生成観察されず(透明)
○ わずかに濁るが結晶生成は観察されず
△ 結晶生成
× 油脂全体が固化
【0031】
【表9】
【0032】
以上の結果より、液状油脂A、液状油脂B、液状油脂I及び液状油脂Jには低温耐性(結晶生成抑制)効果が観察されたが、液状油脂D、液状油脂E及び液状油脂Hでは結晶生成及び固化が起こり低温耐性がないことが判明した。
【0033】
実施例6
液状油脂BにHLB2のポリグリセリン脂肪酸エステルを油に対し1000ppm 添加した油脂、同様に液状油脂BにHLB5のポリグリセリン脂肪酸エステルを油に対し1000ppm 添加した油脂、および液状油脂1にHLB2のポリグリセリン脂肪酸エステルを油に対し1000ppm 添加した油脂の低温耐性(結晶生成抑制)を実施例5と同様の方法で観察した(評価基準は実施例5の場合と同じ)。結果を表10に示す。
【0034】
【表10】
【0035】
これらの結果より、これら油脂の低温耐性(結晶生成抑制)はHLB4以下の油脂結晶抑制剤で改良できることが判明した。[0001]
TECHNICAL FIELD OF THE INVENTION
INDUSTRIAL APPLICABILITY The present invention suppresses an increase in postprandial blood triglyceride (neutral fat) as compared with commonly used edible fats and oils, has less accumulation in the body, and has good storage stability and flavor, and is generally used. The present invention relates to an edible oil / fat composition having a property (which is liquid even at a low temperature and can be used in place of ordinary cooking oil).
[0002]
[Prior art]
People consume the calories they need mainly from carbohydrates and fats, but they promote obesity when the nutritional intake is biased and the calorie intake is excessive as in modern times. And cause problems such as adult illness. In particular, in recent years, the dietary intake of developed countries has increased the intake of lipids, which leads to an increase in triglyceride (neutral fat) concentration in blood and obesity, which is a major cause of adult diseases. Since blood triglyceride (triglyceride) and blood cholesterol levels are closely related to arteriosclerosis, keeping these levels low is particularly important in the prevention of adult diseases. Has been instructed to lower these values. Nevertheless, the number of deaths from adult diseases of the circulatory system is nevertheless increasing.
This is a problem in that meals containing a large amount of lipids (oils and fats) are delicious, and modern people have become accustomed to these meals. In fact, this tendency is apparent also in Japanese who should have had low lipid intake, and the proportion of lipid in the energy intake has increased three-fold in the last 50 years. Therefore, in order to reduce the amount of fat taken in, fat and oil substitutes have been developed in which proteins and sugars are physically reduced to fats and oils to reduce calories. However, these substitutes have not completely replaced the flavor, texture and physical properties of fats and oils. Moreover, they cannot replace the role of a heating medium during cooking, which is another role of fats and oils. Therefore, an oil and fat that has the same flavor, texture and physical properties as the oils and fats currently used, can be used as a heat medium, and can suppress an increase in blood triglyceride (neutral fat) after eating has been developed. If possible, it would be possible to prevent obesity and further reduce the incidence of adult diseases.
Such fats and oils include non-absorbable fats and oils that have been actively developed in recent years. For example, there is a sucrose fatty acid polyester (Mattson et al .: US Pat. No. 3,600,186), which is excreted without being absorbed in the body, and therefore has zero calories derived from fats and oils. However, since it is a non-absorbable fat, the fatty acid sucrose polyester in a liquid state causes problems such as anal leakage and inhibition of fat-soluble vitamin absorption. This substance was approved for use by the FDA on January 30, 1996. However, there is a limitation that a semi-solid or solid sucrose polyester having a melting point of 37.8 ° C. to 71.1 ° C. to which a certain amount of vitamins A, D, E and K is added is used only for salty snacks. This is for preventing the absorption of fat-soluble vitamins and preventing anal leakage. This shows that the present fat and oil substitute is not versatile at present.
Medium chain fatty acid triglycerides (MCT) are known to be non-accumulating in the body. However, when used for heating cooking, a low smoke point (160 ° C. or less) becomes a problem, and it is difficult to use it as cooking oil.
[0003]
Triglycerides containing long-chain saturated fatty acids (for example, behenic acid) and medium-chain fatty acids having 10 or less carbon atoms (Seiden: JP-A-2-1799) and long-chain saturated fatty acids (for example, stearic acid) and short-chain fatty acids were contained. Triglycerides (chrysam: Japanese Patent Application Laid-Open No. 6-506106) contain long-chain saturated fatty acids that are hardly absorbed in vivo and medium- or short-chain fatty acids that do not accumulate in the body. It can be expected to be used as a substitute for fats and oils for the prevention of adult diseases by suppressing an increase in triglycerides (neutral fats), but it is poor in versatility because it is a solid fat.
U.S. Pat. No. 4,976,984 discloses an edible oil composition containing a phospholipid and a glyceride mixture containing 5-100% diglycerides. JP-A-4-300825 and JP-A-4-300826 disclose a serum triglyceride concentration lowering agent and a weight gain inhibitor containing diglyceride as an active ingredient.
Further, JP-A-8-60180 discloses an oil / fat composition in which a diglyceride in which a constituent fatty acid is composed of a long-chain fatty acid and a medium-chain fatty acid is contained in a fat / oil component.
[0004]
[Problems to be solved by the invention]
It is an object of the present invention to provide a blood triglyceride (one of the causes of arteriosclerosis) while having versatility equivalent to conventional oils (which is liquid even at a low temperature and can be used in place of ordinary cooking oil). It is an object of the present invention to provide an edible oil / fat composition which suppresses an increase in neutral fat), has a low accumulation in the body, and has good storage stability and flavor.
[0005]
[Means for Solving the Problems]
The inventors of the present invention have conducted various studies to solve the above-mentioned problems, and have found that fats and oils contain 1,3-diglyceride in an amount of 40% by weight or more, preferably 45% by weight or more, more preferably 50% by weight or more. And less than 1.5% by weight, preferably less than 1% by weight, and 93% by weight or more, preferably 95% by weight or more of the fatty acids constituting diglyceride in the fats and oils are unsaturated fatty acids. The oil and fat composition is less likely to increase postprandial blood triglyceride (neutral fat) than normal edible oil, and further reduces the accumulation of body fat and visceral fat. The present invention was also found to be a liquid fat composition that can be used as well, and the present invention has been achieved.
[0006]
BEST MODE FOR CARRYING OUT THE INVENTION
Hereinafter, the present invention will be described in detail.
1,3-Diglyceride differs from triglyceride (the structure of normal fats and oils), and when ingested and hydrolyzed in the duodenum, mainly produces 1-monoglyceride (triglyceride mainly produces 2-monoglyceride). As a result, the resynthesis of triglyceride in the small intestinal epithelial cells is suppressed, and the blood triglyceride (neutral fat) in the lymphatic vessels is reduced, leading to an effect of reducing the accumulation of body fat and the accumulation of visceral fat. Since 1,2-diglyceride mainly produces 2-monoglyceride when decomposed in the duodenum, such an effect is not exerted. Therefore, in order to exhibit the effects of “suppression of increase in blood triglyceride (neutral fat)”, “reduction of body fat accumulation” and “reduction of visceral fat accumulation”, 40% by weight or more of 1,3- It is essential to contain diglycerides.
[0007]
In the present invention, general-purpose edible oil (for example, cooking oil) is considered as a use from the viewpoint of being a general-purpose liquid oil and fat. Therefore, it is preferable to have a smoke point higher than the temperature at which normal cooking is performed (170 ° C.) (more preferably 180 ° C. or higher, further preferably 190 ° C. or higher). From the viewpoint of flavor, it is desirable that the monoglyceride content in the oil / fat composition is less than 1.5% by weight, preferably less than 1% by weight, and the acid value (AV) is 1.0 or less.
[0008]
Further, from the viewpoint of oxidative stability during storage and cooking, it is preferable to add 50 to 2000 ppm, particularly 400 to 1000 ppm, of an antioxidant to fats and oils, and natural antioxidants, tocopherol, ascorbyl palmitate, ascorbyl steer are added. It is preferable to add one or more antioxidants selected from the group consisting of natural antioxidants, tocopherol, ascorbyl palmitate, and phospholipids. There are one or more antioxidants. Most preferred is a combination of ascorbyl palmitate and tocopherol.
[0009]
Since the main purpose of use of the present fat and oil composition is a general-purpose edible oil (for example, cooking oil), it is inconvenient if crystal formation and solidification occur in a stored state. From this, as a condition under which crystallization and solidification do not occur when stored in a refrigerator, the content of 1,3-diglyceride in fats and oils is 90% by weight or less (preferably 80% by weight or less, more preferably 75% by weight or less). % Or less), and it is essential that the unsaturated fatty acid content in the diglyceride be 93% by weight or more, preferably 95% by weight or more.
The fatty acid constituting the diglyceride has 12 to 24 carbon atoms, preferably 16 to 22 carbon atoms.
[0010]
Further, the content of monounsaturated fatty acid such as oleic acid in the unsaturated fatty acid is desirably 60% by weight or less, preferably 50% by weight or less. The balance is polyunsaturated fatty acids such as linoleic acid and linolenic acid.
More specifically, a fat or oil composition in which the content of unsaturated fatty acids in diglycerides is 93% by weight or more and the content of monounsaturated fatty acids in unsaturated fatty acids is 60% by weight or less is preferable.
Most preferred is an oil or fat composition having an unsaturated fatty acid content of 95% by weight or more in diglycerides and an oleic acid content of 50% by weight or less in unsaturated fatty acids.
The oil / fat composition having such a composition can be obtained by, for example, using a fatty acid obtained by wintering a fatty acid obtained by hydrolyzing rapeseed oil, soybean oil and the like to remove a saturated fatty acid as a raw material.
Further, a crystal inhibitor (for example, polyglycerin fatty acid) having an HLB (employed by an empirical formula suitable for each compound, for example, a Griffin empirical formula for a polyglycerin fatty acid ester) of 4 or less, preferably 3 or less is used. Esters, sucrose fatty acid esters, sorbitan fatty acid esters, etc.) are added to fats and oils in an amount of 200 to 5000 ppm, particularly 500 to 2000 ppm, to improve the stability at low temperatures.
[0011]
【Example】
Hereinafter, the effects of the present invention will be described in more detail with reference to Examples, but the present invention is not limited to these Examples. The percentages in the examples are on a weight basis unless otherwise specified.
(Preparation of fats and oils)
A lipase-derived fatty acid or a soybean oil-derived fatty acid (or wintering) is used as a catalyst with a commercially available lipase preparation (lipase trade name: "Lipozyme 3A", manufactured by Novo Industry AS Co.) which is an immobilized 1,3-position selective lipase. Glycerin was reacted at 40 ° C. After filtering off the lipase preparation, the final product was subjected to molecular distillation and purified by a conventional method to obtain a liquid oil A. Further, a liquid fat B, a liquid fat C, a liquid fat F, a liquid fat G, a liquid fat I, and a liquid fat J were obtained in the same manner with the reaction time being controlled.
Further, an appropriate amount of saturated fatty acid (palmitic acid and / or stearic acid) was added to the rapeseed oil-derived fatty acid, and liquid oils D and E were obtained in the same manner.
The fatty acid fraction was obtained by column chromatography (a triglyceride fraction and a diglyceride fraction were obtained with a Wako Pure Chemical Industries, Ltd. Wakogel C-200 and hexane / ether = 70/30) from the liquid oil / fat synthesized in the same manner. Then, the liquid oil and fat H was obtained by removing the monoglyceride fraction and removing the solvent.
[0012]
The glyceride composition of each fat and oil and the constituent fatty acid composition of diglyceride were analyzed by the following methods.
・ Measurement of glyceride composition distribution After silylation of fats and oils with a silylating agent (manufactured by Kanto Chemical Co., Inc., silylating agent TH), equipped with a capillary column (for example, J & W, DBTM-1) equipped with a flame ion detector. Analysis was performed by gas chromatography, and the glyceride composition distribution and the 1,3-diglyceride content were determined from the retention time and the peak area ratio.
Constituent fatty acid analysis of diglyceride In fats and oils by column chromatography (after removing the triglyceride fraction with Wako Gel C-200 manufactured by Wako Pure Chemical Industries, Ltd. and hexane, a diglyceride fraction was obtained with hexane / ether = 70/30). Diglyceride fractions were collected, and then "2.4.20.2-77 Preparation method of fatty acid methyl ester" and "2.4.21.2-73" in "Standard Oil and Fat Analysis Method, edited by Japan Oil Chemical Association". According to the method of "Fatty acid composition", analysis was performed by gas chromatography. The fatty acid distribution in diglyceride was determined from the retention time and peak area ratio of the obtained chart.
Table 1 shows the composition of the fats and oils used. Table 2 shows the composition of the normal oil.
[0013]
[Table 1]
[0014]
[Table 2]
[0015]
Example 1
A mixed solution containing 10% of various fats and oils, 2% of bovine serum albumin, 0.2% of egg yolk lecithin and 87.8% of distilled water was emulsified using a high-pressure emulsifier to obtain an emulsion having an average particle size of 0.25 mm. This emulsion was orally administered to a 13-week-old SD rat fasted for 18 hours at a concentration of 0.73 ml per 100 g of rat body weight, and each blood collection time group (0, 0.7, 1.0, 1.7, 3. Blood was collected every 3 hours (4 animals per group), and changes in blood triglyceride levels were observed. Table 3 shows the results.
[0016]
[Table 3]
[0017]
In the rat group bred with the liquid fat A and the liquid fat B, the increase in triglyceride (neutral fat) in blood was significantly (t <0.01) significantly suppressed compared to the rat group to which rapeseed oil and soybean oil were administered. Thus, it can be seen that the liquid fat A and the liquid fat B are fats and oils that suppress an increase in blood triglyceride (neutral fat) after eating. On the other hand, the liquid fat C did not significantly (t <0.01) inhibit the blood triglyceride (neutral fat) increase as compared with the rat group to which rapeseed oil and soybean oil were administered.
[0018]
Example 2
Table 6 shows changes in body weight and body fat percentage when 10 rats of the 6-week-old SD type were used for each diet and the rats were fed the diets shown in Table 4 and reared for 3 weeks. In addition, the measurement of the body fat percentage was performed by using an electrical conductivity to measure the body fat percentage for a small animal (EM-SCAN Model SA-2, manufactured by EM-SCAN) under Nembutal anesthesia.
[0019]
[Table 4]
[0020]
[Table 5]
[0021]
The group of rats bred with liquid fat A had significantly (t <0.01) lower body fat percentage than the group of rats bred with rapeseed oil and soybean oil, and the group of rats bred with liquid fat B. Also, the body fat percentage was significantly (t <0.05) lower than that in the rat group bred with rapeseed oil and soybean oil. From this, it can be seen that the liquid fat A and the liquid fat B are fats and oils that have a small accumulation of fat in visceral organs and adipose tissue (adipocytes). On the other hand, it was found that the liquid fat C did not significantly reduce the body fat percentage as compared with the rat group to which rapeseed oil and soybean oil were administered.
[0022]
Example 3
The versatility of the prepared oil was evaluated by cooking evaluation.
Table 6 shows the contents of the newly prepared fats and oils.
[0023]
[Table 6]
[0024]
The oil and fat composition of the present invention was evaluated as cooking oil by making yakisoba. The evaluation was performed by a method in which five panelists evaluated smoke emission during cooking, cooking workability, flavor of yakisoba, and oiliness. The results are shown in Table 7.
・ No smoke at all ○ No smoke at all ○ No smoke at all △ No smoke at all × No smoke at all ・ Cooking workability ◎ Very good ○ Good △ Slightly bad × Bad ・ Flavor ◎ Very good ○ Good △ Slightly bad × Poor material for one person 30g fat
50g of pork
50g cabbage
25 g bamboo shoots
25g onion
Shiitake mushroom 15g
180g Chinese soba
[0025]
[Table 7]
[0026]
From the above results, it was found that the liquid fat 1, the liquid fat 2, and the liquid fat 5 did not generate smoke, had good cooking workability, and had a good flavor, and could be used as well as normal oil. On the other hand, it was found that the liquid fats and oils 3 and 4 had a bad flavor, smoked, could not be used for stir-fry cooking, and had a bad flavor.
[0027]
Example 4
Next, the results of fried food cooking using this fat are shown.
For evaluation as cooking oil, a tempura was prepared using the following materials, and the manner of smoking, cooking workability, and flavor at that time were evaluated by a panel of five persons (the evaluation criteria were the same as in Example 3). Table 8 shows the results.
Material oil used for cooking evaluation 300g
Shrimp 2 tail pumpkin 2 slices batter composition egg 50g
150 g of water
100g flour
[0028]
[Table 8]
[0029]
From the above results, the liquid fat 1, the liquid fat 2, and the liquid fat 5 are smoke-free, have good cooking workability, have a good taste, and are not greasy. I found it. On the other hand, it was found that the liquid fats 3 and 4 had a poor flavor, smoked, and could not be used for fried foods.
[0030]
Example 5
The low-temperature resistance of the fats and oils (crystal formation suppression) was left in a refrigerator at 5 ° C. for one week, and the low-temperature resistance was evaluated from the state of the fats and oils crystal formed at that time. Table 9 shows the results.
・ Low temperature resistance ◎ No crystal formation observed (transparent)
○ Slightly turbid, but no crystal formation was observed. ◆ Crystal formation × solidification of whole fats and oils.
[Table 9]
[0032]
From the above results, it was observed that the liquid fat A, the liquid fat B, the liquid fat I, and the liquid fat J had a low-temperature resistance (crystal formation suppression) effect, but the liquid fat D, the liquid fat E, and the liquid fat H formed crystals. It was found that solidification occurred and there was no low temperature resistance.
[0033]
Example 6
Oil and fat obtained by adding 1000 ppm of HLB2 polyglycerin fatty acid ester to liquid oil B to oil, oil and fat similarly obtained by adding 1000 ppm of HLB5 polyglycerin fatty acid ester to liquid oil and fat B, and polyglycerin fatty acid of HLB2 to liquid oil 1 The low-temperature resistance (suppression of crystal formation) of the oil or fat to which the ester was added at 1000 ppm relative to the oil was observed in the same manner as in Example 5 (the evaluation criteria were the same as in Example 5). Table 10 shows the results.
[0034]
[Table 10]
[0035]
From these results, it was found that the low-temperature resistance (crystal formation suppression) of these fats and oils can be improved by a fat and oil crystal inhibitor having an HLB of 4 or less.
Claims (10)
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