CN1929751B - 在挤出过程中稳定的食物产品用多不饱和脂肪酸组合物 - Google Patents
在挤出过程中稳定的食物产品用多不饱和脂肪酸组合物 Download PDFInfo
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- CN1929751B CN1929751B CN2005800081563A CN200580008156A CN1929751B CN 1929751 B CN1929751 B CN 1929751B CN 2005800081563 A CN2005800081563 A CN 2005800081563A CN 200580008156 A CN200580008156 A CN 200580008156A CN 1929751 B CN1929751 B CN 1929751B
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- cereal
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Classifications
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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- A—HUMAN NECESSITIES
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- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
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- A—HUMAN NECESSITIES
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- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P30/00—Shaping or working of foodstuffs characterised by the process or apparatus
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Abstract
本发明涉及含有PUFA的胶囊封装的颗粒用于制备经过挤出的食物的用途，涉及补充有PUFA的经过挤出的食物以及对其进行制备的方法，所述PUFA包埋于蛋白质基质中。
Description
本发明涉及包含PUFA(长链多不饱和脂肪酸)的组合物在制备经过挤出的谷物食品中的用途。更广义地，本发明涉及此类组合物用于制备所有类型的经过挤出的食物(人类或动物的，包括幼儿和宠物食品)的用途。更具体地，本发明涉及胶囊封装的颗粒的用途用于制备食物，所述颗粒包含PUFA，尤其是来自海洋生物油的PUFA，其能在经过挤出的此类食物(优选地，谷物食品)中保持好的口感(sensory)属性，本发明还涉及由此获得的经过挤出的食物。
过去数年间，海洋生物油作为长链多不饱和脂肪酸的来源，已吸引了很大的兴趣，长链多不饱和脂肪酸作为膳食补充剂的重要性日益增加。如今已有合理的证据表明，膳食中PUFA水平的增加可以降低冠心病导致的死亡率，这是通过对血压、动脉硬化以及血栓形成的影响来实现的。
根据双键在分子碳链中的位置，将PUFA分类为n-9、n-6或n-3PUFA。n-6 PUFA的例子是亚油酸(C18:2)、花生四烯酸(C20:4)、γ-亚麻酸(GLA，C18:13)和二高-γ-亚麻酸(DGLA，C20:3)。n-3 PUFA的例子是α-亚麻酸(C18:13)、二十碳五烯酸(EPA，C20:5)和二十二碳六烯酸(DHA，C22:6)。近年来在食品工业方面，EPA和DHA尤其具有吸引力。最容易获得的这两种脂肪酸的来源是鱼和从其中提取的海洋生物油。
随着双键数目的增多，PUFA的氧化降解也会增加，还会发展出人们不想要的“异味”，主要是鱼的气味和味道。对PUFA，例如EPA和DHA的兴趣增加，推动了对鱼油和PUFA浓缩物进行精炼和稳定的方法的研究。
长期以来，人们已知，新鲜精炼的海洋生物油最初是没有异味和鱼的味道及气味的，但是，氧化导致的变质会迅速发生。人们做出了很多尝试，企图对油加以稳定，例如，通过加入不同的抗氧化剂或它们的混合物。但是，目前大多数尝试都失败了，或者至少还都有进一步改善的可能性。直到现在，人们仍需要开发出基于PUFA或含有PUFA的海洋生物油的组合物，所述组合物在长时间都具有好的口感属性，并且因此能用作为膳食补充剂，例如，以干燥的、能自由流动的粉末或珠粒的形式使用。市场上有很多种经过稳定的PUFA油和微胶囊封装的粉末，较之未经过稳定化的油，它们的确显示出口感上的改进。但是，PUFA的口感问题对它们在食品中的应用和用途来说仍是最限制性的因素。对于通过与热、水分、氧和压力相关的激烈(aggressive)工艺生产的食物而言，这点尤其真确。此类工艺的一个重要的例子就是挤出工艺，其广泛应用于对谷物的制备，尤其是被称为早餐谷物的那些。将PUFA以经过稳定的油或微胶囊封装的粉末的形式加入，会使得最终的谷物具有不可被接受的口感属性。
根据美国专利(USP)4,670,247和EP 285 682 B2，通过下述方法来制备脂溶性珠粒：用水、明胶和糖来乳化脂溶性物质，例如，多不饱和脂肪酸，然后进一步地将所述乳液转化为液滴，将液滴收集到收集粉末中，形成颗粒，将这些颗粒与收集粉末加以分离，对得到的产物进行热处理，以形成水不溶性珠粒。糖是还原糖，其可以选自由果糖、葡萄糖、乳糖、麦芽糖、木糖及其混合物所组成的组。根据USP 4670247，所用的收集粉末是淀粉粉末。热处理导致明胶基质的交联。根据传统加热方法，交联步骤通过下述过程来进行：在电炉中预热过的不锈钢槽上，开始在大约90℃的温度下加热2小时，最后在大约180℃的温度下加热小于一分钟。
根据USP 6,444,227，含有脂溶性物质，例如PUFA的珠粒是通过如下方法获得的：(a)使所述物质、明胶、还原糖，以及可选地，抗氧化剂和/或保湿剂形成水性乳液，(b)可选地，加入交联酶，(c)将所述乳液转变为干燥粉末以及(d)通过辐射或通过孵育(在酶存在的情况下)使得明胶基质在被包被的颗粒中交联。
根据EP 494 417 B1，在交联的明胶基质中包含水可乳化的活性成分的稳定的、热水不可溶的粉末是通过下述方法获得的：(a)在明胶、葡萄糖和/或果糖以及有机或无机酸的碱金属或碱土金属盐的水溶液中制备所述活性成分的乳液，(b)将该乳液的水含量减少至15-4％(w/w)，将组合物加热至55-180℃的温度，同时将组合物的水含量保持为至少3％(w/w)的水平。
根据EP 547 422 B1，包含脂溶性维生素或类胡萝卜素(包埋于基于明胶的基质中)的稳定的、热水不可溶的粉末是通过如下方法来制备的：
(a)制备一种水分散体系，其主要含有这些脂溶性的活性物质、还原糖以及(作为膜形成胶体的)明胶，其与生理可承受的有机氨基化合物(其含有碱性伯氨基以及，此外，另一种氨基、羟基、烷氧基或羧基)组合，所述有机氨基化合物是游离形式的或结合为盐的形式的，和/或与一定量的碱性碱金属或碱土金属化合物组合，使得该分散体系的pH为7.5至10，
(b)将该分散体系转化为以粉末形式存在的干燥的维生素和/或类胡萝卜素产品，以及(c)在60至180℃下对该粉末进行热固化。
现已发现，含有PUFA、按照上文所述交联的明胶基质的珠粒或粉末(例如，分别见USP 4,670,247以及USP 6,444,227或EP 494 417 B1和EP547 442 B1中)可被加入到将经历挤出的食物，优选地，谷物，并且最终产品会具有非常好的口感属性。现在也已发现，除明胶之外，还有其它植物和动物来源的能被交联的蛋白质可用作为基质。植物蛋白质的来源可以是，例如，大豆、豌豆、羽扁豆、豆(bean)、蚕豆、鹰嘴豆和其它豆科植物，麦麸(gluten)、小麦、燕麦、大麦、水稻、苞谷(corn)、玉米(maize)和其它谷物，或芥菜籽(canola)、油菜籽、向日葵等。术语“蛋白质”还包含通过化学方法、酶方法或热降解得到的蛋白质水解产物。
术语“珠粒”包含任何胶囊封装的(尤其是微胶囊封装的)颗粒和粉末，其中含有活性油溶性物质，例如，维生素、类胡萝卜素、PUFA等。所述颗粒可以通过粉末捕捉工艺(具有一层水不溶性物质，例如，淀粉、硅酸钙、硅酸等的珠粒)、通过喷雾干燥或喷雾团聚得到。颗粒尺寸可以在大约10-10000微米的范围内，优选地，大约10-1000微米：对喷雾干燥的产物的而言，大约10-200微米，对于粉末捕捉的产物而言，大约125-850微米，以及对于团聚的产物而言，大约10-300微米。
本发明因此涉及以珠粒形式存在的组合物的用于制备经过挤出的食物(优选地，谷物)的用途，所述组合物包含包埋于经交联的蛋白质基质(优选地，明胶或明胶糖基质)中的PUFA，本发明还涉及包含此类珠粒的经过挤出的食物，优选地，谷物，此外，本发明还涉及制备它们的方法。
以珠粒形式存在的、包含经交联的明胶糖基质的组合物及其制备方法在例如U.S.专利说明书No.4,670,247、5,126,328、5,153,177、5,356,636和6,444,227中有所描述，上述说明书的内容通过引用被并入本申请。上述参考文献中没有具体提到但是等同于(尤其是在其稳定性的方面)它们的组合物及其制备方法也是本发明的实施方式。
本发明的组合物还可额外含有用作为保护性胶体的蛋白质或蛋白质水解产物，例如，来自大豆或羽扁豆的蛋白质或蛋白质水解产物。术语“PUFA”涉及多不饱和脂肪酸，其单独或作为混合物被用作为膳食补充剂，其可以是通过合成来制备的，或从天然来源纯化、浓缩或分离的，其可以是游离酸、其盐、甘油单/双或三酯或其它酯类(例如，乙酯，其可例如通过酯交换作用从甘油酯获得)的形式。
优选的PUFA是n-3和n-6 PUFA，特别是食品级质量的EPA、DPA和DHA，优选地，以其甘油三酯形式存在的，特别是作为从海洋生物油(优选地，从鱼类)获得的浓缩物的组分存在。可通过本领域已知的方法，例如，加入抗氧化剂、乳化剂、调味品或香草，例如迷迭香或鼠尾草提取物来使对其进行稳定和/或脱臭。
术语“经过挤出的食物”和“经过挤出的谷物”的含义就是本领域技术人员所熟悉的含义，其包含通过压缩获得的所有食物或谷物，所述压缩是对其进行制备的一部分，该术语涉及基于苞谷、小麦、黑麦、大麦、燕麦、水稻、小米等的挤出产品，其可选地包含添加剂，例如调味剂、维生素和矿物质。经过挤出的谷物和用于对其进行制备的技术在例如“Extrusion Cooking”，R.Guy，editor，Woodhead Publ.Ltd.，Cambridge，GB，2001中有详细描述，其通过引用被并入本申请说明书中。因此，术语“挤出”包含挤出烹煮以及在相对低的温度下进行的挤出。低温挤出被用于制备意大利粉和面条，而高温下的挤出被用于制备即食(ready-to-eat)谷物，例如早餐谷物或点心。在一种优选的实施方式中，本发明涉及即食谷物。典型地，经过挤出的谷物包括玉米片、麦片、麦麸片(bran flake)、脆米条(rice crispy)、爆米花(rice flake)、麦圈、玉米膨化食品、小麦膨化食品、玉米球和小麦球。它们中的很多都以熟知的商标名在市场上有售。
本发明的食物或谷物制品可以从各种各样不同的主体谷类成分制得，其包括：整个谷粒，例如全麦、水稻、苞谷、燕麦、大麦、小米和黑麦；谷粒的组分，例如，小麦胚芽和麦麸，包括燕麦麦麸、小麦麦麸等；面粉，例如，小麦面粉、玉米面粉等；豆类，例如，大豆、豌豆、豆等；以及非麦麸类纤维来源，例如，梅脯(prune)纤维、甜菜纤维和柑橘类果肉以及其它传统上被包含于即食谷物中的原材料成分。
对根据本发明的经过挤出的食物的制备是根据本领域内公知的方法来进行的。该方法通常可被概括为包括如下步骤：
(a)向挤出机中加入食物材料、含PUFA的珠粒以及可选地，内部润滑剂和/或其它成分，
(b)将这些组分在挤出机中混合，获得均质混合物，
(c)将所述混合物挤出，并切割为小块，以及，可选地
(d)对所述小块进行包被和/或干燥。
在本发明的一种具体的实施方式中，即，对经过挤出的谷物进行的制备中，所述方法包括如下步骤：
(a)向螺杆挤出机中加入谷物、含PUFA的珠粒以及可选地，内部润滑剂和/或其它成分，
(b)将这些组分在挤出机中混合，获得均质混合物，
(c)将所述混合物挤出，并切割为小块，以及，可选地
(d)对所述小块进行包被和/或干燥。
使用合适的挤出螺杆构造的任何挤出机都可使用，传统地，使用水平螺杆挤出机，优选地，使用具有用于获得低剪切混合的构造的挤出机。例如，可以使用交替式窄节距(alternative small pitch)运输元件和分布式混合元件(其相互之间错开一个角度)的组合，用于在挤出机桶的内部提供轴向定向的漏流。交替式运送元件和分布式混合元件和捏合元件的组合使得材料流被连续打断，而没有对物质的剪切，由此使得对物质的混合以低的机械能量输入方式来进行。同向啮合双螺杆挤出机(例如，可从Bühler，Switzerland；Clextral，France；Werner and Pfleiderer，Germany；APV，Englandor Wenger，USA获得的)；或共捏合机(Co-Kneader)(可从Buss，Switzerland获得)是优选的，因为它们较之单螺杆挤出机能提供更好的混合作用。
组分可以作为预混合物被加入到挤出机中，或在挤出机的不同位置单独加入。其它成分包含通常用于制备经过挤出的谷物的添加剂，例如，调味剂、抗氧化剂、维生素、矿物质、保护性胶体和能增加食物产品的营养或膳食价值的其它成分。
为被成功包括进食物产品，以及为了在通常的贮藏条件下稳定，PUFA珠粒的颗粒尺寸应当从50μm(微米)至1600μm。优选的颗粒尺寸范围从大约160μm至840μm，更优选的范围为从180-450μm。尤其优选的是200-300μm之间的颗粒尺寸范围。
根据公开的数据值，经交联的珠粒中PUFA的含量可以在1-80％或20-40％之间变动，优选的范围分别为10-60％或25-35％，但是该含量可以总是随着消费者的特定趋势和需求，以及特定的最终产品而变动。
在经过挤出的谷物中，PUFA的含量还可以在很宽的限制内变动，可以选用取决于需求的剂量。因此，强化含量可以在从0.1％至10％的范围内，优选是1-3％。
在好的口感质量方面，经PUFA强化的经过挤出的谷物的稳定性预期能在通常的贮藏条件下保持数周直到数月。
下述实施例详细说明了本发明。
实施例
将118.5g干燥鱼胶、23.4g果糖、20.9g甘油和17.2g抗坏血酸钠置于1000ml双层壁容器中，加入140ml去离子水，在用搅拌盘(micerdisc)以500转/分钟(rpm)和大约40℃下进行搅拌的同时，使混合物称为溶液。该溶液被称为基质溶液。之后，将132.2g ROPUFA‘30’n-3Food Oil(精炼的鱼油混合物，具有最少30％的以甘油三酯形式存在的n-3PUFA[至少25％DHA、EPA和DPA]，用混合的生育酚、棕榈酸抗坏血酸酯加以稳定，含有迷迭香提取物)乳化于该基质中，搅拌10分钟。在乳化和搅拌期间，搅拌盘被设置为4800rpm。在该乳化之后，乳液的内部相的平均颗粒尺寸为大约254nm(通过激光衍射测量)。用310ml去离子水稀释乳液，温度被保持为70℃。
随后，将1300g玉米淀粉(用硅酸流化)放置到实验室用喷雾盘上，冷却至至少0℃。用旋转喷雾嘴分两部分将乳液喷雾到喷雾盘上。由此获得的包被有玉米淀粉的颗粒被过筛(筛级为0.125至0.63mm)，筛去多余的玉米淀粉，用空气流在室温下进行干燥。由此获得了389g包被有玉米淀粉的颗粒，其具有非常好的流动性，已被完全干燥，并能对其很好地加以操作。
为进行热处理，将上述颗粒中的100g的部分放置到流化床干燥机(Retsch)上，加热到135℃，20分钟。该热处理使得明胶基质交联(Maillard反应)。最终产物的DHA/EPA含量为9.0％(DHA：5.3％；EPA：3.7％)，交联度94％，干燥损失1.2％。交联度是通过下述方法来测量的：15分钟内将产物分散到55℃水中，浓度为20％，测定释放的PUFA油。
具有该挤出稳定形式的早餐谷物是根据本领域公知的方法在水平双螺杆挤出机(Bühler，Switzerland)上制备的。
下述组合物被用于制备经过挤出的谷物产品：
| ％(w/w) | |
| 米粉 | 65 |
| 玉米面粉 | 20 |
| 糖 | 10 |
| NaCl | 1 |
| PUFA珠粒 | 1 |
| 水 | 定容至100 |
工艺参数：
I/d＝16；螺杆转速380rpm；压力67bar；口模温度156℃。
挤出之后，在包被盘中用糖浆(水中75％蔗糖)包被谷物，随后在流化床干燥机上干燥。
通过经过培训的品尝小组对由此获得的未被包被的早餐谷物加以评价。用关于鱼味的分级机制，通过描述性分析来进行口感分析。
与补充有含有未交联的基质PUFA的珠粒的谷物相比，上述谷物的口感属性明显更好。
Claims (14)
1.包含包埋于经交联的鱼胶基质中的含PUFA的海洋生物油的、以胶囊封装的颗粒形式存在的组合物用于制备经过挤出的食物的用途，其中，对所述鱼胶基质的交联是在对包含鱼胶基质溶液和含PUFA的海洋生物油的乳液干燥之后进行热处理来实现的。
2.如权利要求1所述的组合物的用途，所述组合物以珠粒形式存在。
3.如权利要求1或2所述的组合物的用途，其中所述食物是谷物。
4.如权利要求1或2所述的组合物的用途，其中所述含PUFA的海洋生物油是经过纯化和稳定的海洋生物油。
5.如权利要求1或2所述的组合物的用途，其中主要的PUFA含量由EPA和DHA所代表。
6.经过挤出的食物，其特征在于，其含有在权利要求1-2、4和5中任意一项中所定义的组合物。
7.如权利要求6所述的经过挤出的食物，其中所述食物是谷物。
8.一种方法，用于制备如权利要求6所述的经过挤出的食物，所述方法是通过本身已知的方式来进行的。
9.一种方法，用于制备如权利要求6或7所述的经过挤出的食物，所述方法包括如下步骤：
(a)向挤出机中加入食物材料和根据权利要求1-2、4和5中任意一项中所定义的组合物，
(b)将这些组分在所述挤出机中混合，获得均质混合物，以及
(c)将所述混合物挤出，并切割为小块。
10.如权利要求9所述的方法，在步骤(a)中，还向所述挤出机中加入内部润滑剂和/或其它成分。
11.如权利要求9或10所述的方法，还包括如下步骤：
(d)对所述小块进行包被和/或干燥。
12.如权利要求9所述的方法，用于制备经过挤出的谷物，所述方法包括如下步骤：
(a)向螺杆挤出机中加入谷物和根据权利要求1-2、4和5中任意一项中所定义的组合物，
(b)将这些组分在所述挤出机中混合，获得均质混合物，以及
(c)将所述混合物挤出，并切割为小块。
13.如权利要求12所述的方法，在步骤(a)中，还向所述螺杆挤出机中加入内部润滑剂和/或其它成分。
14.如权利要求12或13所述的方法，还包括如下步骤：
(d)对所述小块进行包被和/或干燥。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP04006502 | 2004-03-18 | ||
| EP04006502.1 | 2004-03-18 | ||
| PCT/EP2005/002486 WO2005089569A1 (en) | 2004-03-18 | 2005-03-09 | Extrusion-stable poly-unsaturated fatty-acid compositions for food products |
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| Publication Number | Publication Date |
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| CN1929751A CN1929751A (zh) | 2007-03-14 |
| CN1929751B true CN1929751B (zh) | 2011-06-22 |
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| CN2005800081563A Active CN1929751B (zh) | 2004-03-18 | 2005-03-09 | 在挤出过程中稳定的食物产品用多不饱和脂肪酸组合物 |
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| JP (2) | JP2007529209A (zh) |
| KR (1) | KR101285501B1 (zh) |
| CN (1) | CN1929751B (zh) |
| CA (1) | CA2559473C (zh) |
| ES (1) | ES2549258T3 (zh) |
| PL (1) | PL1732405T3 (zh) |
| WO (1) | WO2005089569A1 (zh) |
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| AU2007260873B2 (en) | 2006-06-22 | 2013-05-02 | Dsm Ip Assets B.V. | Encapsulated labile compound compositions and methods of making the same |
| US8221809B2 (en) | 2006-06-22 | 2012-07-17 | Martek Biosciences Corporation | Encapsulated labile compound compositions and methods of making the same |
| TW200820913A (en) * | 2006-08-25 | 2008-05-16 | Martek Biosciences Corp | Food fortification with polyunsaturated fatty acids |
| US20090155447A1 (en) * | 2007-12-12 | 2009-06-18 | Solae, Llc | Protein extrudates comprising omega-3 fatty acids |
| WO2010132060A1 (en) * | 2009-05-15 | 2010-11-18 | Tate And Lyle Ingredients Americas, Inc. | Low-temperature extrusion process using instant starch to produce puffed/expanded food product |
| CL2012002056A1 (es) * | 2012-07-24 | 2014-01-24 | Map Chile SpA | Proteina animal micrencapsulada para consumo humano que comprende particulas proteicas, y una matriz de gelatina de origen animal; y particula de proteina animal microencapsulada para consumo humano. |
| CN109965328A (zh) * | 2013-03-15 | 2019-07-05 | 麦克考米克有限公司 | 包含香辛料、香草、水果和蔬菜粉的包囊化组合物 |
| KR20180117136A (ko) * | 2016-02-26 | 2018-10-26 | 디에스엠 아이피 어셋츠 비.브이. | 신규 코팅 시스템 (ii) |
| US20210077446A1 (en) * | 2016-12-13 | 2021-03-18 | Dsm Ip Assets B.V. | Pufa salt formulations (ii) |
| CN108851154A (zh) * | 2017-05-11 | 2018-11-23 | 康师傅饮品控股有限公司 | 包埋颗粒及其制备方法 |
| RU2020128641A (ru) * | 2018-02-02 | 2022-02-28 | Сосьете Де Продюи Нестле С.А. | Стабилизация омега-3 жирных кислот с помощью отрубей |
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| US5143737A (en) * | 1989-10-13 | 1992-09-01 | The Regents Of The University Of California | Method to produce unsaturated milk fat and meat from ruminant animals |
| CN1422123A (zh) * | 2000-04-04 | 2003-06-04 | 澳大利亚食品工业科学中心 | 食品成分的包封 |
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| US4217370A (en) * | 1977-08-25 | 1980-08-12 | Blue Wing Corporation | Lipid-containing feed supplements and foodstuffs |
| JPH0568501A (ja) * | 1991-07-15 | 1993-03-23 | Terumo Corp | 膨化食品およびスープ様食品ならびに膨化食品の製造方法 |
| DE4141351A1 (de) * | 1991-12-14 | 1993-06-17 | Basf Ag | Stabile pulverfoermige vitamin- und/oder carotinoid-praeparate und verfahren zu deren herstellung |
| US5853761A (en) * | 1995-02-13 | 1998-12-29 | Fujisawa Pharmaceutical Co., Ltd. | Stabilizing agent for oleaginous, physiologically active substances |
| WO1998018610A1 (en) * | 1996-10-28 | 1998-05-07 | Lengerich Bernhard H Van | Embedding and encapsulation of controlled release particles |
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2005
- 2005-03-09 KR KR1020067019164A patent/KR101285501B1/ko active IP Right Grant
- 2005-03-09 JP JP2007503238A patent/JP2007529209A/ja active Pending
- 2005-03-09 US US10/592,860 patent/US20080241336A1/en not_active Abandoned
- 2005-03-09 WO PCT/EP2005/002486 patent/WO2005089569A1/en not_active Application Discontinuation
- 2005-03-09 CN CN2005800081563A patent/CN1929751B/zh active Active
- 2005-03-09 ES ES05715875.0T patent/ES2549258T3/es active Active
- 2005-03-09 EP EP05715875.0A patent/EP1732405B1/en active Active
- 2005-03-09 PL PL05715875T patent/PL1732405T3/pl unknown
- 2005-03-09 CA CA2559473A patent/CA2559473C/en active Active
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2010
- 2010-10-08 JP JP2010228836A patent/JP2011045376A/ja active Pending
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2011
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5143737A (en) * | 1989-10-13 | 1992-09-01 | The Regents Of The University Of California | Method to produce unsaturated milk fat and meat from ruminant animals |
| CN1422123A (zh) * | 2000-04-04 | 2003-06-04 | 澳大利亚食品工业科学中心 | 食品成分的包封 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1732405B1 (en) | 2015-07-22 |
| CN1929751A (zh) | 2007-03-14 |
| US20170105443A1 (en) | 2017-04-20 |
| JP2007529209A (ja) | 2007-10-25 |
| WO2005089569A8 (en) | 2005-11-24 |
| EP1732405A1 (en) | 2006-12-20 |
| CA2559473C (en) | 2015-07-21 |
| PL1732405T3 (pl) | 2015-12-31 |
| US20080241336A1 (en) | 2008-10-02 |
| KR101285501B1 (ko) | 2013-07-12 |
| US20110223289A1 (en) | 2011-09-15 |
| WO2005089569A1 (en) | 2005-09-29 |
| JP2011045376A (ja) | 2011-03-10 |
| CA2559473A1 (en) | 2005-09-29 |
| KR20060131903A (ko) | 2006-12-20 |
| ES2549258T3 (es) | 2015-10-26 |
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