JP5155863B2 - 油脂組成物 - Google Patents
油脂組成物 Download PDFInfo
- Publication number
- JP5155863B2 JP5155863B2 JP2008528705A JP2008528705A JP5155863B2 JP 5155863 B2 JP5155863 B2 JP 5155863B2 JP 2008528705 A JP2008528705 A JP 2008528705A JP 2008528705 A JP2008528705 A JP 2008528705A JP 5155863 B2 JP5155863 B2 JP 5155863B2
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- Prior art keywords
- oil
- fat
- fatty acid
- oils
- fats
- Prior art date
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- LGJMUZUPVCAVPU-HRJGVYIJSA-N stigmastanol Chemical compound C([C@@H]1CC2)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]2(C)CC1 LGJMUZUPVCAVPU-HRJGVYIJSA-N 0.000 description 1
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- 208000011580 syndromic disease Diseases 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
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- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
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- 239000011701 zinc Substances 0.000 description 1
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 238000011680 zucker rat Methods 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
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- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
- A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
- A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
- A23D9/013—Other fatty acid esters, e.g. phosphatides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/158—Fatty acids; Fats; Products containing oils or fats
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/115—Fatty acids or derivatives thereof; Fats or oils
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Edible Oils And Fats (AREA)
- Fats And Perfumes (AREA)
- Fodder In General (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
一方、ジアシルグリセロールにも、抗肥満作用等が見出されている(特許文献7、8)。更に、ω3系脂肪酸やリノール酸等の特定の脂肪酸を高含量としたジアシルグリセロールを含む油脂が知られている(特許文献9〜11)。
このほか、ジアシルグリセロールと植物ステロールとを組合せた油脂組成物には、血中コレステロール値改善効果等が見出されている(特許文献12)。
共役リノール酸は、遊離脂肪酸であることから、脂肪酸特有の異味により、そのまま摂取したり、食品に利用するには適していなかった。そこで、共役リノール酸をエステル体にすることで、共役リノール酸の応用範囲を広げる試みがなされている(特許文献13〜18)、(非特許文献2、3)。
(A)構成脂肪酸中の不飽和脂肪酸含量が80重量%以上で、共役リノール酸含量が2〜92重量%、かつω3系不飽和脂肪酸含量が15重量%未満であるジアシルグリセロールを15重量%以上含有し、モノアシルグリセロール含量が5重量%以下、遊離脂肪酸含量が5重量%以下であり、1,3−ジアシルグリセロール/1,2−ジアシルグリセロールの重量比が1〜5である油脂 100重量部
(B)トコフェロール 0.001〜2重量部
を含有する油脂組成物を提供するものである。
本発明において、油脂中の1,3−DAG/1,2−DAGの重量比は1〜5であるが、好ましくは1.5〜3.8、更に2〜3.5、特に2.1〜3.2であるのが、低温での保存性、生理効果、油脂の工業的生産性の点で好ましい。
DAG中のCLA含量/TAG中のCLA含量 ・・・(1)式
本発明においては、トランス不飽和脂肪酸の含有量は、AOCS法(American Oil Chem.Soc.Official Method:Ce1f−96、2002年)で測定した値のことである。
更に、油脂(A)の原料となる油脂としては、脱臭油の他、予め脱臭されていない未脱臭油脂を用いることができる。本発明の態様においては、原料の一部又は全部に、未脱臭油脂を使用するのが、共役リノール酸以外のトランス不飽和脂肪酸を低減し、原料油脂由来の植物ステロール、植物ステロール脂肪酸エステル、トコフェロールを残存させることができるので好ましい。
本発明の態様において、ビタミンC又はその誘導体の含有量は、油脂(A)100部に対して、アスコルビン酸として0.004〜0.1部であることが好ましく、更に0.006〜0.08部、特に0.008〜0.06部であることが好ましい。
本発明の態様において、植物ステロール類(C)の含有量は、油脂(A)100部に対して0.05〜30部であるのが好ましく、より好ましくは0.3〜20部、更に1〜10部、特に2〜8部、殊更2.5〜4.7部とすることが、コレステロール低下作用、風味、外観、低温での保存性、油脂の工業的生産性の点で好ましい。ここで、成分(C)としてエステル体等の誘導体を含む場合は、遊離体に換算した値を成分(C)の含有量とする。
植物ステロール類(C)中の、カンペステロールの含有量は10〜40%であることが好ましく、更に15〜35%、特に22〜30%であることが、風味、外観、油脂の工業的生産性、結晶析出、低温での保存性、生理効果の点で好ましい。
植物ステロール類(C)中の、スチグマステロールの含有量は3〜30%であることが好ましく、更に5〜25%、特に7〜15%であることが、風味、外観、油脂の工業的生産性、結晶析出、低温での保存性、生理効果の点で好ましい。
植物ステロール類(C)中の、β−シトステロールの含有量は30〜60%であることが好ましく、更に35〜58%、特に40〜56%であることが、風味、外観、油脂の工業的生産性、結晶析出、低温での保存性、生理効果の点で好ましい。
本発明の油脂組成物を応用する食品としては、油脂組成物を食品の一部として含む油脂加工食品が挙げられる。かかる油脂加工食品としては、例えば、特定の機能を発揮して健康増進を図る健康食品、機能性食品、特定保健用食品等が挙げられる。具体的な製品としては、パン、ケーキ、ビスケット、パイ、ピザクラスト、ベーカリーミックス等のベーカリー食品類、スープ、ソース、ドレッシング、マヨネーズ、コーヒーホワイトナー、アイスクリーム、ホイップクリーム等の水中油型乳化物、マーガリン、スプレッド、バタークリーム等の油中水型乳化物、ポテトチップス等のスナック菓子、チョコレート、キャラメル、キャンデー、デザート等の菓子、ハム、ソーセージ、ハンバーグ等の肉加工食品、牛乳、チーズ、ヨーグルト等の乳製品、ドウ、エンローバー油脂、フィリング油脂、麺、冷凍食品、レトルト食品、飲料、ルー等が挙げられる。本発明の油脂組成物の他に、油脂加工食品の種類に応じて一般に用いられる食品原料を添加し製造することができる。本発明の油脂組成物の食品への配合量は、食品の種類によっても異なるが、一般に0.1〜100%、特に1〜80%が好ましい。
肉類としては、例えば、牛、豚、羊(マトン又はラム)、ウサギ、カンガルー等の畜肉、獣肉及びその副生物、加工品(ミートボール、ミートボーンミール、チキンミール等の上記原料のレンダリング物)、マグロ、カツオ、アジ、イワシ、ホタテ、サザエ、魚粉(フィッシュミール)等の魚介類等が挙げられる。蛋白質としては、例えば、カゼイン、ホエー等の乳蛋白質や卵蛋白質等の動物蛋白質、大豆蛋白質等の植物蛋白質が挙げられる。穀物類としては、例えば、小麦、大麦、ライ麦、マイロ、トウモロコシ等が挙げられる。ぬか類としては、例えば、米ぬか、ふすま等が挙げられる。粕類としては大豆粕等が挙げられる。飼料中の肉類、蛋白質、穀物類、ぬか類、粕類の合計量は5〜93.9%であることが好ましい。
(1)共役リノール酸(CLA)の調製
プロピレングリコール1050gと水酸化カリウム350gとを混合した後、攪拌しながら60℃まで昇温し、水酸化カリウムを完全に溶解した。その後、60℃で窒素バブリングを30分間行い、溶存酸素を除いた。次いで、これを130℃まで昇温し、リノール酸(東京化成製)700gを少量ずつ添加した。窒素雰囲気下、157℃まで昇温し、4時間攪拌して共役化反応を行った。これを室温まで冷却後、5N塩酸を1L加え、pHを3に調整した。反応物にヘキサンを加えて溶媒抽出を行い、エバポレーターで溶媒を留去して、CLA700gを得た。
(1)で調製したCLA1100部と固定化リパーゼ110部とを混ぜ、窒素雰囲気下40℃に加温した。次いで、グリセリン180.5部を添加し、減圧下(2〜5torr)、40℃にて7時間エステル化反応を行った。ろ過を行って固定化酵素を除去した後、反応終了物(TAG5.7%、DAG73.2%、MAG12.8%、FFA8.3%)をシリカゲルカラムクロマトグラフィー(Wako C−200、和光純薬製)に充填し、有機溶媒で溶出して精製を行った。すなわち、ヘキサン、へキサン−酢酸エチル(97:3、V/V)、へキサン−酢酸エチル(9:1、V/V)、へキサン−酢酸エチル(4:1、V/V)、へキサン−酢酸エチル(3:1、V/V)、へキサン−酢酸エチル(2.5:1、V/V)で順に溶出し、DG画分を得た。エバポレーターで溶媒を留去して得た油脂100部に対して、トコフェロール(ミックストコフェロールMDE−6000、八代製)を0.02部添加したものを油脂Aとした。そのグリセリド組成、脂肪酸組成を表1に示す。なお、油脂Aの1,3−DAG含量は78.7%、1,2−DAG含量は19.7%であった。従って、1,3−DAG/1,2−DAG=4(重量比)であった。
(1)で調製したCLA520部と固定化リパーゼ52部とを混ぜ、窒素雰囲気下40℃に加温した。次いで、グリセリン56.9部を添加し、減圧下(2〜5torr)、50℃にて20時間エステル化反応を行った。ろ過を行って固定化酵素を除去した後、反応終了物(TAG41.8%、DAG36.8%、MAG1.2%、FFA20.2%)をシリカゲルカラムクロマトグラフィー(Wako C−200、和光純薬製)に充填し、有機溶媒(へキサン−酢酸エチル(97:3、V/V))で溶出し、DG画分とMG画分を除いた。これを更にフロリジルカラムクロマトグラフィーにかけ、精製を行った。すなわち、ヘキサン、へキサン−酢酸エチル(30:1、V/V)でTG画分を溶出した後、エバポレーターで溶媒を留去した。得られた油脂100部に対して、トコフェロール(ミックストコフェロールMDE−6000、八代製)を0.02部添加したものを油脂Bとした。そのグリセリド組成、脂肪酸組成を表1に示す。
魚油(花王製)400部とグリセリン16部とを混合し、ナトリウムメチラート1.2部存在下、減圧下にて(0.133kPa)100℃4時間エステル交換反応を行った。得られた反応生成物を、(2)と同様にシリカゲルクロマトグラフィ−で精製し、エバポレーターで溶媒を留去した。次いで、得られた油脂100部に対して、トコフェロール(ミックストコフェロールMDE−6000、八代製)を0.02部添加して、油脂Cを得た。そのグリセリド組成、脂肪酸組成を表1に示す。
中鎖脂肪酸トリグリセリド(ココナードMT、花王製)400部とグリセリン16部とを混合し、ナトリウムメチラート1.2部存在下、減圧下にて(0.133kPa)100℃4時間エステル交換反応を行った。得られた反応生成物を、(2)と同様にシリカゲルクロマトグラフィ−で精製し、エバポレーターで溶媒を留去した。次いで、得られた油脂100部に対して、トコフェロール(ミックストコフェロールMDE−6000、八代製)を0.02部添加して、油脂Dを得た。そのグリセリド組成、脂肪酸組成を表1に示す。
プロピレングリコール225部に、水酸化カリウム75部を完全に溶解し、20分間窒素バブリングした後、窒素雰囲気下120℃まで昇温した。次いで、サフラワー油180部を滴下した後、170℃にて2.5時間反応を行った。得られた反応生成物300部と、グリセリン12部とを、ナトリウムメチラート0.8部存在下、減圧下にて(0.133kPa)100℃4時間エステル交換反応を行った。これを、(2)と同様にシリカゲルクロマトグラフィ−で分画し、エバポレーターで溶媒を留去した。次いで各画分を混合して得られた油脂100部に対して、トコフェロール(ミックストコフェロールMDE−6000、八代製)を0.02部添加することにより、油脂Eを得た。そのグリセリド組成、脂肪酸組成を表1に示す。なお、油脂Eの1,3−DAG/1,2−DAG=2(重量比)であった。
油脂Eとナタネ油を重量比1:2で混合した油脂100部に対し、トコフェロール(ミックストコフェロールMDE−6000、八代製)を0.02部、植物ステロール脂肪酸エステル(CardioAid−S、ADM製)を4部添加し、油脂Fを得た。油脂Fのグリセリド組成、脂肪酸組成を表1に示す。なお、ナタネ油の構成脂肪酸組成を表1脚注(*2)に示す。
大豆油脂肪酸をウィンタリングして飽和脂肪酸を低減したもの455部と菜種油脂肪酸195部とグリセリン107部を、固定化リパーゼ(Lipozyme RM IM、ノボザイムス社)を使用して、エステル化反応を行った(40℃、5時間、0.07hPa)。次いで、固定化リパーゼを濾別し、薄膜蒸留を行った後、水洗、脱臭した。この油脂100部に対して、トコフェロール(ミックストコフェロールMDE−6000、八代製)を0.02部添加した。ここに、植物ステロール(フィトステロールF、タマ生化学製)を0.3部添加したものを油脂G、4部添加したものを油脂Hとした。油脂Gのグリセリド組成、脂肪酸組成を表1に示す。なお、油脂Gの1,3−DAG含量は57.7%、1,2−DAG含量は27.5%であった。従って、1,3−DAG/1,2−DAG=2(重量比)であった。
油脂Aと油脂Gとを重量比7:3、5:5、3:7で混合し、それぞれ油脂I、油脂J、油脂Kとした。また、油脂Aと油脂Hとを重量比7:3、5:5、3:7で混合し、それぞれ油脂L、油脂M、油脂Nとした。
ナタネ油と油脂Aと油脂Gとを重量比50:25:25で混合し、油脂Oを調製した。また、ナタネ油と油脂Aと油脂Hとを重量比50:25:25で混合し、油脂Pを調製した。なお、ナタネ油は前記油脂Fで使用したのと同じものである。
(i)グリセリド分布
ガラス製サンプル瓶に、サンプル10mgとトリメチルシリル化剤(「シリル化剤TH」、関東化学製)0.5mLとを加え、密栓した後、70℃で15分間加熱した。水1mL添加後、ヘキサンを2mL加え、よく振とうした。静置後、ヘキサン相を抽出し、ガスクロマトグラフィー(GLC)に供して、分析を行った。
GLC条件
装置;Hewlett Packard製 6890型
カラム;DB−1HT(J&W Scientific製) 7m
カラム温度;initial=80℃、final=340℃
昇温速度=10℃/分、340℃にて20分間保持
検出器;FID、温度=350℃
注入部;スプリット比=50:1、温度=320℃
サンプル注入量;1μL
キャリアガス;ヘリウム、流量=1.0mL/分
サンプル約12mgに1/2N水酸化ナトリウム・メタノール溶液0.6mLを添加した。次いで、三ふっ化ほう素メタノール錯体メタノール溶液(和光純薬製)を0.6mL添加後、70℃にて30分間加熱した。飽和食塩水1mLを添加後、へキサン1mLを添加して、よく振とうした。へキサン相を抽出し、無水硫酸ナトリウムを加えて、脂肪酸メチルエステルを調製した。
メチルエステル化した脂肪酸をGLCに供して分析を行った。
GLC条件
装置;Hewlett Packard製 6890型
カラム;CP−Sil88 for Fame(ジーエルサイエンス製)
0.25mm×50m
カラム温度;initial=150℃、final=225℃
150℃にて5分間保持後、2℃/分で昇温し、225℃にて15分間
保持
検出器;FID、温度=250℃
注入部;スプリット比=40:1、温度=250℃
サンプル注入量;1μL
キャリアガス;ヘリウム、流量=1.0mL/分
油脂A、油脂Bを用いて、下記方法にて、保存試験を行った。ガラス製サンプル瓶(50mL容)に、油脂を20g入れ、窒素シールした後、密栓した。これを−20℃の冷凍庫に保存した。5年後に、常温に静置して解凍し、開栓して、臭い、外観を下記基準で官能評価した。結果を表2に示す。
a:劣化臭、ケミカル臭が殆んど感じられず、良好。
b:劣化臭はやや感じられるが、ケミカル臭はなく、やや良好。
c:劣化臭とケミカル臭があり、やや不良。
d:劣化臭とケミカル臭が強く、不良。
a:通常の油(サラダ油)と同じ液状で、良好。
b:通常の油よりもやや粘性が高く、やや良好。
c:ゲル状となっている部分があり、やや不良。
d:ゲル状部分が大半を占め、不良。
表3に示す組成で、飼料を常法に従って製造した。6〜7週齢のZuckerラットを1群6匹ずつ4群に分けた。まず、飼料1で4日間予備飼育した(摂食量一定)。次いで、各飼料を用いてそれぞれ9日間飼育した。この時の摂食量は、毎日測定した。飼料投与最終日に解剖を行い、肝臓、腎周囲脂肪組織、副睾丸周囲脂肪組織を摘出し、その重量を測定した。また、肝臓中のトリグリセリド量を測定した。結果を表4に示す。
油脂Aに、植物ステロール(フィトステロールF、タマ生化学製)を1%、2%、4%添加したものを、それぞれ油脂Aa、油脂Ab、油脂Acとした。また、油脂Aに植物ステロール脂肪酸エステル(CardioAid−S、ADM製)を1%、2%、4%添加したものを、それぞれ油脂Ad、油脂Ae、油脂Afとした。
3点:僅かに濁りや沈殿があるが、流動性がある。
2点:一部で沈殿があり、流動性が損なわれている。
1点:固化して、全く流動性がない。
油脂A、油脂G、油脂H、油脂I〜K、油脂L〜N、油脂O、油脂Pを20mL容のガラス製サンプル瓶に10g入れ、閉蓋して5℃及び10℃の恒温槽に静置した。6時間後、24時間後の各サンプルの状態を、実施例4と同じ評価基準にて目視で観察し、評価を行った。評価結果を表6に示す。なお、表1において、油脂A、油脂Gの全構成脂肪酸組成とDAGの構成脂肪酸組成は同じとして取り扱い、DAG中のCLA量と油脂中のPS量との重量比(CLA/PS)を算出した。
Claims (4)
- 次の成分(A)、(B)及び(C):
(A)構成脂肪酸中の不飽和脂肪酸含量が80重量%以上、共役リノール酸含量が20〜92重量%、かつω3系不飽和脂肪酸含量が15重量%未満であるジアシルグリセロールを20重量%以上含有し、モノアシルグリセロール含量が5重量%以下、遊離脂肪酸含量が5重量%以下であり、1,3−ジアシルグリセロール/1,2−ジアシルグリセロールの重量比が1〜5である油脂 100重量部
(B)トコフェロール 0.001〜2重量部
(C)植物ステロール類 0.05〜4.7重量部
を含有し、
(A)油脂に含まれるジアシルグリセロールを構成する共役リノール酸と、(C)植物ステロール類との重量比(共役リノール酸/植物ステロール類)が1〜400である、油脂組成物。 - 請求項1記載の油脂組成物を含有する食品。
- 請求項1記載の油脂組成物を含有する飼料。
- 請求項1記載の油脂組成物を含有する医薬品。
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Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2428678B (en) * | 2005-08-02 | 2010-01-27 | Univ Keele | Glyceride compounds and uses thereof |
US20090264520A1 (en) * | 2008-04-21 | 2009-10-22 | Asha Lipid Sciences, Inc. | Lipid-containing compositions and methods of use thereof |
JP5220566B2 (ja) * | 2008-11-19 | 2013-06-26 | 花王株式会社 | ペットフード |
JP5316160B2 (ja) * | 2009-03-27 | 2013-10-16 | 日油株式会社 | 水中油型食用乳化組成物 |
WO2011074575A1 (ja) * | 2009-12-15 | 2011-06-23 | 花王株式会社 | 油脂組成物 |
BRPI0905607A2 (pt) | 2009-12-24 | 2011-08-23 | Companhia Refinadora Da Amazonia | processo para a produção de diacilgliceróis através de reações de hidrólise de oléo de palma catalisadas pelas enzimas amano ps e amano im |
JP5706094B2 (ja) * | 2010-03-31 | 2015-04-22 | 花王株式会社 | 油脂組成物 |
WO2011148829A1 (ja) * | 2010-05-25 | 2011-12-01 | 花王株式会社 | ペットフード |
US9017753B2 (en) | 2011-05-20 | 2015-04-28 | Kao Corporation | Oil or fat composition containing diglycerides |
JP6166984B2 (ja) * | 2012-09-04 | 2017-07-19 | 花王株式会社 | 油脂組成物 |
BR102014012953A2 (pt) | 2014-05-29 | 2018-04-17 | Universidade Estadual De Campinas - Unicamp | Processo de obtenção de composições estruturadas de gorduras, composições estruturadas assim obtidas e seus usos |
JP6797269B2 (ja) * | 2018-11-20 | 2020-12-09 | 花王株式会社 | 油脂組成物 |
CN110141564A (zh) * | 2019-06-06 | 2019-08-20 | 广东省农业科学院蚕业与农产品加工研究所 | 一种富含多不饱和脂肪酸的甘油酯混合物及其制备方法和应用 |
CN111040875A (zh) * | 2020-01-06 | 2020-04-21 | 武汉轻工大学 | 一种抗氧化剂及其制备方法和应用 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002265374A (ja) * | 2001-03-06 | 2002-09-18 | Taiyo Kagaku Co Ltd | 体脂肪減少用組成物 |
JP2003160794A (ja) * | 2001-09-13 | 2003-06-06 | Kao Corp | 油脂組成物 |
WO2005052102A1 (en) * | 2003-11-28 | 2005-06-09 | Onbio Corporation | A composition enriched in diglyceride with conjugated linoleic acid |
WO2005104865A1 (ja) * | 2004-04-28 | 2005-11-10 | Kao Corporation | 油脂組成物 |
JP2006075164A (ja) * | 2004-09-10 | 2006-03-23 | Cognis Ip Management Gmbh | 不飽和脂肪酸及びそのエステルを含むエマルション |
JP2006513307A (ja) * | 2003-04-25 | 2006-04-20 | イルシンウェルズ コーポレーション リミティッド | 共役リノール酸を含む高純度ジグリセリド油脂組成物及びその製造方法 |
JP2006137923A (ja) * | 2004-04-28 | 2006-06-01 | Kao Corp | 油脂組成物 |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3098560B2 (ja) | 1991-03-28 | 2000-10-16 | 花王株式会社 | 体重増加抑制剤 |
US5554646A (en) | 1992-04-29 | 1996-09-10 | Wisconsin Alumni Research Foundation | Method for reducing body fat in animals |
ES2133655T3 (es) | 1994-03-31 | 1999-09-16 | Unilever Nv | Aceites con bajo contenido de acidos grasos saturados. |
US5814663A (en) | 1994-08-29 | 1998-09-29 | Wisconsin Alumni Research Foundation | Method for maintaining an existing level of body fat |
JP3569116B2 (ja) | 1996-10-18 | 2004-09-22 | 花王株式会社 | 液状汎用型油脂組成物 |
US6004611A (en) * | 1996-10-18 | 1999-12-21 | Kao Corporation | General-purpose oils composition |
US6139897A (en) * | 1998-03-24 | 2000-10-31 | Kao Corporation | Oil or fat composition containing phytosterol |
US6025348A (en) * | 1998-04-30 | 2000-02-15 | Kao Corporation | Oil and fat composition containing phytosterol |
DE69940629D1 (ja) * | 1998-03-24 | 2009-05-07 | Kao Corp | |
FR2784268B1 (fr) | 1998-10-12 | 2000-12-29 | Gervais Danone Sa | Nouvelle composition alimentaire, a base de matiere issue du lait, sous la forme d'une emulsion huile dans eau |
US20050013907A1 (en) * | 1998-10-12 | 2005-01-20 | Compagnie Gervais Danone | Food composition based on a substance derived from milk comprising conjugate linoleic acid glycerides |
JP4565750B2 (ja) * | 1999-04-27 | 2010-10-20 | 株式会社ヤクルト本社 | 共役リノール酸エステルの製造法 |
US6762203B2 (en) * | 1999-08-03 | 2004-07-13 | Kao Corporation | Oil composition |
JP4098927B2 (ja) | 1999-08-03 | 2008-06-11 | 花王株式会社 | 油脂組成物 |
EP1097708B1 (en) | 1999-11-02 | 2003-09-17 | Loders Croklaan B.V. | Use of trans-trans isomers of conjugated linoleic acid |
US6225910B1 (en) * | 1999-12-08 | 2001-05-01 | Gentex Corporation | Smoke detector |
JP2004505041A (ja) | 2000-08-02 | 2004-02-19 | ファーマニュートリエンツ | シンドロームxの予防及び治療のための方法及び組成物 |
WO2002009693A1 (en) | 2000-08-02 | 2002-02-07 | Pharmanutrients | Method and compositions for prevention and/or treatment of diabetes and glucose modulation |
BRPI0113105B1 (pt) | 2000-08-08 | 2018-03-27 | Kao Corporation | Composição de óleo/gordura, alimento, ração e produto farmacêutico compreendendo dita composição e processo de preparação de uma composição de alimento compreendendo uma gordura ou óleo |
US6432453B1 (en) | 2000-08-26 | 2002-08-13 | Metagenics, Inc. | Dietary supplement containing glycerol ester of conjugated linoleic acid and rosemary extract containing carnosic acid |
WO2002041706A2 (en) | 2000-11-21 | 2002-05-30 | Alpha Foods Ingredients, Inc. | Bioactive compositions comprising conjugated linoleic acid glycerides and methods for producing bioactive conjugated linoleic acid |
JP2002194387A (ja) | 2000-12-27 | 2002-07-10 | Kanegafuchi Chem Ind Co Ltd | 油脂の安定化方法 |
JP4995377B2 (ja) * | 2001-04-26 | 2012-08-08 | 花王株式会社 | 油脂組成物 |
JP3970669B2 (ja) | 2001-08-02 | 2007-09-05 | 日清オイリオグループ株式会社 | 共役脂肪酸含有モノグリセリドおよびその製造方法 |
JP2003171272A (ja) | 2001-12-07 | 2003-06-17 | Rinoru Oil Mills Co Ltd | 10トランス,12シス−共役リノール酸を有効成分とする抗腫瘍剤 |
-
2006
- 2006-08-11 CN CN2006800555988A patent/CN101505609B/zh not_active Expired - Fee Related
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Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002265374A (ja) * | 2001-03-06 | 2002-09-18 | Taiyo Kagaku Co Ltd | 体脂肪減少用組成物 |
JP2003160794A (ja) * | 2001-09-13 | 2003-06-06 | Kao Corp | 油脂組成物 |
JP2006513307A (ja) * | 2003-04-25 | 2006-04-20 | イルシンウェルズ コーポレーション リミティッド | 共役リノール酸を含む高純度ジグリセリド油脂組成物及びその製造方法 |
WO2005052102A1 (en) * | 2003-11-28 | 2005-06-09 | Onbio Corporation | A composition enriched in diglyceride with conjugated linoleic acid |
WO2005104865A1 (ja) * | 2004-04-28 | 2005-11-10 | Kao Corporation | 油脂組成物 |
JP2006137923A (ja) * | 2004-04-28 | 2006-06-01 | Kao Corp | 油脂組成物 |
JP2006075164A (ja) * | 2004-09-10 | 2006-03-23 | Cognis Ip Management Gmbh | 不飽和脂肪酸及びそのエステルを含むエマルション |
Also Published As
Publication number | Publication date |
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US20100267681A1 (en) | 2010-10-21 |
CN101505609A (zh) | 2009-08-12 |
KR101297921B1 (ko) | 2013-08-19 |
JPWO2008018147A1 (ja) | 2009-12-24 |
US8853192B2 (en) | 2014-10-07 |
KR20090037927A (ko) | 2009-04-16 |
WO2008018147A1 (en) | 2008-02-14 |
CN101505609B (zh) | 2013-07-17 |
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