CN108882737A - 乳化组合物及粉末组合物 - Google Patents
乳化组合物及粉末组合物 Download PDFInfo
- Publication number
- CN108882737A CN108882737A CN201780017405.8A CN201780017405A CN108882737A CN 108882737 A CN108882737 A CN 108882737A CN 201780017405 A CN201780017405 A CN 201780017405A CN 108882737 A CN108882737 A CN 108882737A
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- CN
- China
- Prior art keywords
- bitter taste
- menthyl
- fragrance
- composition
- emulsification
- Prior art date
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- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
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Abstract
本发明提供一种乳化组合物及粉末组合物,其是式(1)所表示的薄荷基醚类的乳化组合物或将该乳化组合物进行干燥而获得的粉末组合物,容易调配于饮食品或香妆品中,此外苦味的上升较慢,具有清爽且温和的苦味(如柚皮苷的苦味)。[式(1)中,X表示部分结构式(1‑a)或(1‑b),R1及R2表示甲基、乙基、丙基或异丙基]。
Description
技术领域
本发明是涉及一种乳化组合物及粉末组合物,其是作为具有特异的香气和苦味的香气赋予或香气调变剂或苦味赋予用的香味调变剂而有用且含有特定的薄荷基醚。本发明也是涉及一种含有该等乳化组合物及粉末组合物的饮食品及香妆品。本发明也是涉及一种使用该等乳化组合物及粉末组合物的饮食品或香妆品的香气赋予或香气调变方法及饮食品的苦味赋予方法。
背景技术
人除了通过食物而摄取能量源以外,也感受到食物带来的身体状况的维持、由食物的美味或食感带来的满足感,食物对于人发挥着重要的功能。食物的美味据说是源于饮食品的碳水化合物、脂肪等营养成分,并且其饮食品的味道和香气也为重要的要素。用口所感觉到的味觉、和用鼻所感觉到的嗅觉虽然为独立的感觉,但根据近年的研究,据说在饮食时,味觉和嗅觉在脑内进行整合,作为食物的美味和食物的满足感而被认知。
关于饮食品的香气,据说虽然由鼻所吸入的香气被鼻黏膜所感知的鼻腔香气(前鼻腔香气)也较为重要,但饮食品经口腔刺激味觉,感知由咽喉传入到鼻的香气的口腔香气(后鼻腔香气)最为重要。
自以往,作为有气味的物质,已知刺激嗅觉,同时也对味觉赋予刺激的化合物。作为此种化合物的代表性的例子所知的薄荷脑具有强力的清凉香和分配到黏膜的刺激感,广泛用于各种饮食品、香妆品中。同时,关于味觉,已知具有特有的苦味。在使用薄荷脑的情况下,对于作为对象的饮食品、香妆品,该等性质存在有利地发挥作用的情况、和不利地发挥作用的情况。
例如,在为了获得薄荷脑的清凉感而用于饮食品的情况下,由于挥发性较高,故而指出清凉感不持续、及其特有的苦味为不利的方面。因此,多数创作用以克服作为该薄荷脑所存在的缺点的苦味的掩蔽方法。举一例子,揭示了使用作香料的缩水甘油酸酯成为苦味的掩蔽剂(专利文献1)。
另一方面,为了使薄荷脑的清凉感持续,同时抑制苦味,也广泛进行将薄荷脑的化学结构进行变更的尝试,合成有用的衍生物。为此所开发的化合物是合成利用薄荷脑的羟基的酯衍生物、在薄荷脑的构成碳骨架中导入了羧酸的对薄荷烷羧酸衍生物。作为更具体的化合物,已知:3-羟基丁酸薄荷酯、薄荷脑甘油醚(Coolact 10,高砂香料公司注册商标,专利文献2)、乳酸薄荷酯(Frescolate ML,Symrise AG公司注册商标)、丁二酸单薄荷酯(Physcool,V.Mane fils公司注册商标)、N-乙基对薄荷烷羧酰胺(WS-3)、2-[(5-甲基-2-丙烷-2-基环己烷羰基)胺基]乙酸乙酯(WS-5)、N-(4-甲氧基苯基)对薄荷烷羧酰胺(WS-12)、N,2,3-三甲基-2-异丙基丁酰胺(WS-23)等(专利文献3)。该等化合物是以具有清爽的香气、具有清凉感持续作用、无苦味为特征,以化合物单一成分、或通过和薄荷脑并用而用于各种制品中。
另一方面,苦味是表现食品的特征的重要的构成要素,作为苦味成分,有:涩柿子、葡萄酒等中所含的单宁、茶中所含的儿茶素、咖啡中所含的绿原酸、蛇麻草中所含的具有啤酒的苦味的特征的阿尔法酸等。该等成分分別具有特有的苦味,在构成包含该等的饮食品的方面,被认识为重要的化合物(非专利文献1)。然而,源自天然的苦味原材料由于除了特有的苦味以外,也具有源于原料的天然物特有的香味,故而仅限于在通常的饮食品的应用。因此,期待具有优良品质的苦味的化合物的开发,而不是源于原材料的天然物特有的香气。
应用了薄荷脑特有的刺激和苦味的例子较少,仅揭示了为了防止药物的乱用而添加薄荷脑的例子(专利文献4)。而且,薄荷脑由于具有强力的清凉香,故而以往为了赋予苦味而在通常的饮食品中调配较为困难。尚未知为了克服该缺点而追求薄荷脑特有的苦味作为优良品质的苦味,同时为了抑制强力的清凉香而研究薄荷脑衍生物的尝试。
[以往技术文献]
[专利文献]
[专利文献1]日本专利第5198533号公报
[专利文献2]日本专利特开昭58-88334号公报
[专利文献3]日本专利特开昭47-16648号公报
[专利文献4]日本专利特表2005-500364号公报
[非专利文献]
[非专利文献1]山田恭正,「New Food Industry」2002年,44卷,2号,49~55页
发明内容
[发明要解决的问题]
因此,本发明者等人鉴于所述课题,对于提供具有无杂味的苦味且以抑制冰凉感及清凉感的薄荷脑衍生物作为有效成分的香味调变剂进行努力研究,其结果为,发现2-甲基-4-薄荷基氧基-2-丁醇等特定的薄荷基醚类较为有用,以往进行过专利申请(日本专利特开2016-84418号公报)。
该等化合物是抑制如薄荷脑及其衍生物中常见的冰凉感及清凉感,香气中具有稍稍木质、辛辣且青草的香气,且关于苦味,具有无杂味的优良品质的苦味且使该苦味持续。然而,为了对饮食品进行苦味赋予而调配,期待通过延迟苦味的上升,制成更清爽且温和的苦味,而在饮食品中取得甜味、酸味等的平衡。而且,该等薄荷基醚类为油溶性,故而在调配于水分较多的食品中的情况下,有难以均匀地混合,在保存中分离等问题方面。
因此,本发明所欲解决的课题在于提供一种乳化组合物及粉末组合物,其容易调配于饮食品或香妆品中,此外苦味的上升较慢,具有清爽且温和的苦味。
[解决问题的技术手段]
本发明者等人此外对于4-薄荷基氧基-2-丁酮等特定的薄荷基醚类进行努力研究,结果发现:可以通过制成含有特定的薄荷基醚类的乳化组合物、或在制成乳化组合物后进行干燥而成为粉末组合物的形态,而容易调配于饮食品或香妆品中,而且,尤其在添加于饮食品中的情况下,一面维持尖锐的苦味特性,一面制成和不制成乳化组合物的情况相比,延迟苦味的上升且更清爽且温和的苦味,从而完成本发明。另外,本发明者等人也发现:可以通过将油脂调配于乳化组合物中而使苦味持续更长时间。
另外,本发明中作为薄荷基醚类所揭示的4-薄荷基氧基-2-丁酮虽然为有机化学研究中所合成的化合物,但关于其香味的特性并无任何记载,关于其衍生物也未发现报告(Tetrahedron Lett.,47,2905(2006))。
如此,本发明是提供以下。
[1]一种乳化组合物,其含有下述(A)~(D):
(A)下述式(1)所表示的薄荷基醚类;
[化1]
[式(1)中,X表示部分结构式(1-a)或(1-b),R1及R2表示甲基、乙基、丙基或异丙基]
(B)水;
(C)选自糖类、一元醇或多元醇中的一种以上;及
(D)乳化剂。
[2]如[1]的乳化组合物,其进一步含有(E)食用油脂类。
[3]如[1]或[2]中记载的乳化组合物,其中薄荷基醚类为下述式(2)所表示的2-甲基-4-薄荷基氧基-2-丁醇。
[化2]
[4]一种粉末组合物,其是使如[1]至[3]中任一项记载的乳化组合物干燥而成。
[5]一种饮食品,其含有如[1]至[3]中任一项记载的乳化组合物或如[4]中记载的粉末组合物。
[6]一种香妆品,其含有如[1]至[3]中任一项记载的乳化组合物或如[4]中记载的粉末组合物。
[7]一种饮食品或香妆品的香气赋予或香气调变方法,其是通过含有如[1]至[3]中任一项记载的乳化组合物或如[4]中记载的粉末组合物而进行。
[8]一种饮食品的苦味赋予方法,其是通过使如[1]至[3]中任一项记载的乳化组合物或如[4]中记载的粉末组合物含有于饮食品中而进行。
[发明的效果]
含有特定的薄荷基醚类的本发明的乳化组合物或粉末组合物无杂味而优良品质且具有锐利苦味,和未进行乳化的所述薄荷基醚类相比,可以制成延迟苦味的上升,更清爽且温和的苦味。其结果为,可以赋予如使人想起柚皮苷等柑橘类的苦味的苦味。
而且,在本发明的优选的形态中,含有特定的薄荷基醚类的本发明的乳化组合物或粉末组合物具有少许的冰凉感及清凉感、和稍稍的木质、辛辣且青草的香气。
而且,在本发明的优选的形态中,通过在所述乳化组合物中调配油脂,可以使所述薄荷基醚类特有的苦味持续更长时间。通过将该等本发明的乳化组合物或粉末组合物作为香气赋予或香气调变剂或苦味赋予用的香味调变剂而调配于香料组合物、饮食品中,可以利用香气和优良品质的苦味开发具有目前所未知的新的香味的饮食品,可以扩展于新的应用范围中。
具体实施方式
本发明是关于一种乳化组合物及粉末组合物,其含有:(A)式(1)所表示的薄荷基醚类、(B)水、(C)选自糖类、一元醇或多元醇中的一种以上、及(D)乳化剂。式(1)所表示的薄荷基醚类是未进行乳化等,显示出作为其自身、香气赋予或香气调变剂或苦味赋予用的香味调变剂、冰凉感赋予剂、苦味赋予剂的效果而具有有用性。另外,所谓「香气赋予或香气调变」的用语中的「或」是和「及/或」为相同意义。
然而,可以通过制成含有(A)式(1)所表示的薄荷基醚类、(B)水、(C)选自糖类、一元醇或多元醇中的一种以上、及(D)乳化剂的乳化组合物或粉末组合物,而提高在水中的分散性,容易调配于饮食品或香妆品中,同时延迟苦味的上升,使其更清爽且温和。而且,可以通过视需要在所述乳化组合物中含有食用油脂类,此外增加食用油脂类的含量,而使薄荷基醚类的苦味持续更长时间。此外,含有式(1)中所表示的薄荷基醚类的乳化组合物或粉末组合物优选在保存时也稳定。
例如,在为了赋予香气和苦味而在葡萄柚风味饮料中调配2-甲基-4-薄荷基氧基-2-丁醇的情况下,若在油溶性香料中调配并添加,则油溶性香料油脂上浮,使油中所含的2-甲基-4-薄荷基氧基-2-丁醇直接作用于口腔内。另一方面,在制成乳化组合物的情况下,2-甲基-4-薄荷基氧基-2-丁醇的微细的粒子均匀地作用于口腔内。其结果为,可以进一步赋予类似葡萄柚的苦味。
制成本发明的乳化组合物或粉末组合物的薄荷基醚类和未进行乳化的薄荷基醚类相比,苦味的上升变慢,使伴随其的苦味感觉更加清爽且温和。
作为本发明的乳化组合物或粉末组合物中所使用的式(1)所表示的薄荷基醚类,并无特別限定,具体而言,可例示:式(3)所表示的4-薄荷基氧基烷基酮,例如4-薄荷基氧基-2-丁酮。而且,可例示:式(4)所表示的烷基-4-薄荷基氧基烷醇,例如式(2)所表示的2-甲基-4-薄荷基氧基-2-丁醇等,但并不限定于此。式(1)中的R1及R2分別独立地表示甲基、乙基、丙基或异丙基,可以相互相同也可以不同。R1及R2优选甲基。
为了获得式(1)所表示的薄荷基醚类,可以依据以下所示的反应式1,通过步骤(1)而合成式(3)所表示的4-薄荷基氧基烷基酮,此外通过步骤(2)而合成式(4)所表示的烷基-4-薄荷基氧基烷醇。
[化3]
反应式1
反应式1:[R1及R2表示甲基、乙基、丙基或异丙基;M表示Li或MgX,X表示卤素原子]
若对反应式1的各步骤进行概括说明,则作为步骤(1),在触媒的存在下使薄荷脑和烷基乙烯基酮进行麦可型加成反应,合成式(3)所表示的4-薄荷基氧基烷基酮。作为步骤(2),可以通过在步骤(1)中所获得的式(3)所表示的4-薄荷基氧基烷基酮中,使烷基金属试剂进行反应而合成式(4)所表示的烷基-4-薄荷基氧基烷醇。
以下,详细地说明步骤(1)及步骤(2)。作为步骤(1)的原料所使用的薄荷脑(2-异丙基-5-甲基环己醇)虽然存在8种异构物,但较理想为使用具有优异的香气的天然型的l-薄荷脑,但并不限定于此。作为一个反应模块的烷基乙烯基酮是3-丁烯-2-酮(甲基乙烯基酮)、1-戊烯-3-酮(乙基乙烯基酮)、1-己烯-3-酮(丙基乙烯基酮)或4-甲基-1-戊烯-3-酮(异丙基乙烯基酮),虽然均可以自市场采购,但也可以依据已知的方法进行合成而使用。
用于步骤(1)的反应的烷基乙烯基酮只要相对于薄荷脑为当量以上,则并无特別制约,但就经济性的观点而言,可列举:1.5当量至5当量,优选可列举:2当量至4等量。
在麦可型加成反应中触媒的利用较为有效,可以利用酸性型或碱性型的触媒。关于酸性型触媒,例如作为布忍斯特酸触媒,可列举:硫酸、盐酸、磷酸、对甲苯磺酸等,优选使用对甲苯磺酸。而且,可列举:作为路易斯酸触媒的三氟化硼醚错合物、四氯化钛、三氯化铝等,优选使用三氟化硼醚错合物。也可以使用碱性型的触媒,也可以使用:三级胺类、氢氧化四级烷基胺类。
步骤(1)的反应即使在无溶剂的情况下也进行,但也可以使用溶剂,优选在反应原料的薄荷脑、烷基乙烯基酮及使用的触媒中具有不活性的性质的溶剂,更优选使用:甲苯、庚烷、己烷等烃溶剂、二***等醚系触媒、二氯甲烷等氯系溶剂,更优选使用:二氯甲烷等氯系溶剂。
反应温度虽然受到使用的触媒的使用量及/或活性、及使用的溶剂的影响,但可列举优选-78℃~50℃,进一步优选0℃~30℃的温度条件。而且,反应时间虽然受到使用的触媒的使用量及/或活性、及使用的溶剂的影响,但并无特別限制,可列举:数小时至数天。反应时间可以一面利用气相层析法或薄层层析法等监测反应的进行一面决定反应时间。步骤(1)中所获得的式(3)所表示的4-薄荷基氧基烷基酮可以视需要使用管柱层析法、减压蒸馏等方法进行精制。
在步骤(2)中,通过使式(3)所表示的4-薄荷基氧基烷基酮的羰基和烷基金属试剂进行加成反应,而合成式(4)所表示的烷基-4-薄荷基氧基烷醇。和式(3)所表示的4-薄荷基氧基烷基酮进行反应的碱金属化合物可以使用:甲基锂、乙基锂、丙基锂等烷基锂或氯化甲基镁、溴化甲基镁、氯化乙基镁、溴化乙基镁等烷基格里钠德试剂。该等烷基金属试剂可以为自市场所采购的金属试剂,也可以使用自对应的金属和卤化烷基所制备的试剂。用于反应的烷基金属试剂优选相对于式(3)所表示的4-薄荷基氧基烷基酮使用等莫耳至2倍莫耳,特别优选使用1.05倍莫耳至1.5倍莫耳。
使用的反应溶剂虽然取决于使用的烷基金属试剂的性质,但只要为通常在烷基金属试剂中在不活性的状态下使烷基金属试剂分散于溶剂中,并使作为反应基质的式(3)所表示的4-薄荷基氧基烷基酮进行溶解的溶剂,则并无特別限制,例如优选使用:二***、甲基叔丁醚、四氢呋喃、1,4-二烷。
反应条件虽然受到使用的烷基金属试剂的性质的影响,但由于通常羰基化合物和烷基金属试剂的反应为发热反应,受到溶剂中的水分、在气体中或溶剂中溶存的氧的影响,所以优选在回避该等的反应条件下进行,优选在氮气气体下使用经脱水的溶剂等。
反应温度虽然受到使用的烷基金属试剂的种类、使用的溶剂的影响,但优选-78℃~40℃,进一步优选0℃~30℃的温度条件。而且,反应时间虽然受到使用的烷基金属试剂的种类、使用的溶剂的影响,但以数小时结束反应。优选一面利用气相层析法或薄层层析法等监测反应的进行一面决定反应时间。步骤(2)中所获得的式(4)所表示的烷基-4-薄荷基氧基烷醇优选视需要使用管柱层析、减压蒸馏等方法进行精制。
式(1)所表示的薄荷基醚类可以两种以上任意的比率进行混合而用于本发明的乳化组合物,也可以特别利用和其他清凉感持续剂的并用,而发挥将清凉感的持续和薄荷脑的苦味进行改质的效果。
含有式(1)所表示的薄荷基醚类的本发明的乳化组合物并无特別限定,可以采用利用公知的方式将式(1)所表示的薄荷基醚类进行乳化而成的乳化组合物,例如,可以除了作为(A)的作为香味调变化合物成分的式(1)所表示的薄荷基醚类以外,也包含(B)水、(C)选自糖类、一元醇或多元醇中的一种以上、(D)乳化剂,将该等进行混合、搅拌及乳化而获得。
所述乳化时,例如可以将(A)式(1)所表示的薄荷基醚类作为油相部,将(B)水及(C)选自糖类、一元醇或多元醇中的一种以上作为水相部,而制备为水中油型(Oil-in-water型;O/W型)乳化组合物。
藉此,使式(1)所表示的薄荷基醚类的苦味的上升和不制成乳化组合物的情况相比更慢,使伴随其的苦味感到更清爽且温和。另外,苦味的上升较慢的意思,是指自包含于口腔中开始稍稍迟缓地感到苦味。苦味通常为忌避的味道,当苦味物质进入到口腔中时,立即表现出苦味,赋予较强的冲击的某种不快感的情况较多。然而,苦味物质中也具有表现优选的苦味。例如,柑橘中所含的柚皮苷据说在柑橘果实或柑橘果汁中呈现出清爽且温和的苦味。本发明的乳化组合物具有接近该柑橘中的柚皮苷的苦味的味道特性。
而且,在所述油相部中,除了(A)式(1)所表示的薄荷基醚类以外,也可以含有(E)食用油脂类。通过视需要在所述乳化组合物中含有食用油脂类,可以使苦味持续更长时间。所述食用油脂类的调配量对苦味的持续时间产生影响。即,通过增加食用油脂类的调配量,可以使苦味的持续时间变成更长时间,通过降低食用油脂类的调配量,可以相对地缩短苦味的持续时间。
而且此外,在用以使式(1)所表示的薄荷基醚类溶解的剂(例如油相部)中,也可以除所述食用油脂类以外,含有SAIB(蔗糖·二乙酸酯·六异丁酸酯)作为比重调整剂,或含有通常的各种香料作为式(1)所表示的薄荷基醚类以外的香味成分。
作为可以使用的(E)成分的食用油脂类,优选容易和式(1)所表示的薄荷基醚类进行混和的油脂类,例如可列举:大豆油、芝麻油、玉米油、菜籽油、米糠油、棉籽油、蓖麻油、花生油、橄榄油、棕榈油、红花油、小麦胚芽油、椰子油、葵花籽油、山茶油、可可脂、鲱鱼油、鲑鱼油、青花鱼油、鯊鱼油、鲭科金枪鱼油、鲸油、海豚油、墨鱼油、秋刀鱼油、鲱鱼油、鳕鱼油、牛脂、鸡油、猪油、黄油等动植物油脂类及其等的硬化油类、中链饱和脂肪酸甘油三酸酯(以下,称为MCT)等。特别优选MCT。作为该MCT,例如可列举:己酸三甘油脂、辛酸三甘油脂、癸酸三甘油脂、月桂酸三甘油脂、及如其等的任意的混合物的碳原子数6~12的中链饱和脂肪酸的甘油三酸酯,其等之中,特别优选:辛酸三甘油脂、癸酸三甘油脂及其等的任意的混合物。该等MCT混合物可以在市场上廉价且容易地获得。本发明的乳化组合物中的食用油脂类的含量虽无特別限定,但相对于式(1)所表示的薄荷基醚类1质量份,可以为通常为0.01~2000质量份,优选0.1~500质量份,更优选0.5~100质量份,进一步优选2~50质量份的范围内。
SAIB(蔗糖·二乙酸酯·六异丁酸酯)是用以调整本发明的乳化组合物中的油相部的比重而调配,在调配了本发明的乳化组合物的最终制品(饮食品、香妆品)为水性组合物的情况下,可以调配以防止乳化组合物因比重差而分离。
作为可以使用的SAIB,例如可列举:其比重为约1.13~约1.19,优选约1.14~约1.15的范围内的SAIB。本发明的乳化组合物中的SAIB的含量可以根据使用的SAIB的比重、调配了乳化组合物的饮料的比重等而变化,但通常,较理想为本发明的乳化组合物中的油相部整体的比重、和作为调配了本发明的乳化组合物的最终制品的水性组合物(例如本发明的饮食品或香妆品)的比重差成为0.05以下,尤其成为0.03以下的量。若该比重差为0.05以下,则在将调配了本发明的乳化组合物的水性组合物长期保存的情况下,不易发生环圈或油脂上浮。关于油相部中的SAIB的混合比率,在将含有SAIB的油相部整体设为1质量份的情况下,通常可例示约0.2质量份~约0.6质量份,优选可例示约0.3质量份~约0.5质量份的范围内。然而,较理想为最终一面测定调配了本发明的乳化组合物的水性组合物的比重及该乳化组合物中的油相部的比重一面经验性地发现比重差成为0.05以下的SAIB的含量。
作为式(1)所表示的薄荷基醚类以外的香味成分,作为通常的各种香料(可以和式(1)所表示的薄荷基醚类一同含有的其他通式的各种香料),例如作为清凉感持续剂,可列举:3-羟基丁酸薄荷酯、薄荷脑甘油类(Coolact 10,高砂香料公司的注册商标)、乳酸薄荷酯(Frescolate ML,Symrise AG公司的注册商标)、丁二酸单薄荷酯(Physcool,V.Manefils公司的注册商标)、N-乙基-对薄荷烷羧酰胺(WS-3)、2-[(5-甲基-2-丙烷-2-基环己烷羰基)胺基]乙酸乙酯(WS-5)、N-(4-甲氧基苯基)-对薄荷烷羧酰胺(WS-12)、N,2,3-三甲基-2-异丙基丁酰胺(WS-23)等。
而且,作为可以和式(1)所表示的薄荷基醚类一同含有的所述以外的通常的各种香料,可列举:「专利厅,周知惯用技术集(香料)第II部食品香料,第8-87页,平成12年(2000年)1月14日发行」中所记载的合成香料、天然精油、天然香料、动植物萃取物等。
作为该等香料成分,例如作为烃化合物,可列举:α-蒎烯、β-蒎烯、月桂烯、莰烯、柠檬烯等单萜;朱乐倍半萜、雪松烯、石竹烯、长叶烯等倍半萜;1,3,5-十一碳三烯等。
作为醇化合物,可列举:丁醇、戊醇、异戊醇、己醇等直链·饱和烷醇;戊烯醇、(Z)-3-己烯-1-醇、2,6-壬二烯醇等直链·不饱和醇;沉香醇、香叶草醇、香茅醇、四氢月桂烯醇、金合欢醇、橙花叔醇、雪松醇等萜烯醇;苄醇、苯基乙基醇、呋喃甲醇等芳香族醇。
作为醛化合物,可列举:乙醛、异戊醛、己醛、辛醛、壬醛、癸醛等脂肪族饱和醛;(E)-2-己烯醛、2,4-辛二醛等脂肪族不饱和醛;香茅醛、柠檬醛等萜烯醛;苯甲醛、肉桂醛、香草醛、乙香草醛、糠醛、向日花香醛等芳香族醛。
作为酮化合物,可列举:2-庚酮、2-十一酮、1-辛烯-3-酮等直链·饱和及不饱和酮;乙偶姻、二乙酰、2,3-戊二酮、麦芽醇、乙基麦芽醇、2,5-二甲基-4-羟基-3(2H)-呋喃酮等直链及环状二酮及羟基酮;香旱芹酮、薄荷酮、诺卡酮等萜烯酮;α-紫罗兰酮、β-紫罗兰酮、β-突厥烯酮等源自萜烯分解物的酮;覆盆子酮等芳香族酮。
作为呋喃·醚化合物,可列举:玫瑰醚、氧化芳樟醇、薄荷呋喃、茶螺烷等环状醚类;甲基胡椒酚、大茴香脑等芳香族醚类。
作为酯化合物,可列举:乙酸乙酯、乙酸异戊烷等脂肪族醇的乙酸酯;乙酸沉香酯、乙酸香叶酯、乙酸薰衣草酯等萜烯醇的乙酸酯;丁酸乙酯、己酸乙酯等脂肪酸和低级醇的酯;乙酸苄酯、水杨酸甲酯等芳香族酯。
作为内酯化合物,可列举:γ-癸内酯、γ-十二内酯、δ-癸内酯、δ-十二内酯等饱和内酯;7-癸烯-4-内酯、2-癸烯-5-内酯等不饱和内酯。
作为酸化合物,可列举:丁酸、4-甲基-3-戊烯酸、辛酸、硬脂酸、油酸、亚麻油酸、次亚麻油酸等饱和、不饱和脂肪酸。
作为含氮化合物,可列举:吲哚、粪臭素、吡啶、经烷基取代的吡邻胺苯甲酸甲酯等。
作为含硫化合物,可列举:甲硫醇、糠基硫醇、二甲硫醚、二甲双硫醚、二糠基二硫醚、异硫氰酸烯丙酯等。
作为天然精油,可列举:甜橙、酸橙、卑宁、柠檬、葡萄柚、酸橙(lime)、佛手柑、柑橘、橙花、胡椒薄荷、绿薄荷、熏衣草、黄金菊、迷迭香、桉树、鼠尾草、罗勒、玫瑰、天竺葵、茉莉、香水树、大茴香、小茴香、八角茴香、丁香、肉桂、姜、肉豆蔻、小豆蔻、蛇麻草、柳杉、扁柏、香根草、天竺薄荷、劳丹脂等。
而且,作为各种萃取物,也可列举:花草茶·香辛料萃取物;咖啡·绿茶·红茶·乌龙茶萃取物;乳或乳加工品及其等的脂肪酶·蛋白酶等酶分解物。
在含有式(1)所表示的薄荷基醚类的乳化组合物中,视需要可以含有:通常用于香料组合物中的水、乙醇等溶剂;乙二醇、1,2-丙二醇、甘油、苯甲酸苄酯、柠檬酸三乙酯、脂肪酸甘油三酸酯、脂肪酸甘油二酯等香料保留剂。
本发明中所使用的作为(B)成分的水优选和作为(C)成分的糖类、一元醇或多元醇一同构成所述水相部。在水相部中的含水率通常为50%以下、特别优选约0~25%的范围内的含水状态下使用,若含水率超过50%,则有丧失防腐性的可能性。
本发明中所使用的作为(C)成分的糖类、一元醇或多元醇是为了乳化的稳定而调配。作为糖类,例如可列举:葡萄糖、果糖、蔗糖、海藻糖、纤维双糖、麦芽三糖、鼠李糖、乳糖、麦芽糖、核糖、木糖、***糖及饴糖等,作为一元醇,例如可列举:乙醇、丙醇及异丙醇等,作为多元醇,例如可列举:甘油、丙二醇、1,3-丁二醇、山梨糖醇、麦芽糖醇及淀粉分解还原物等,可列举:该等两种以上的混合物。
本发明的乳化组合物中的所述水相部的使用量优选相对于油相部1质量份,通常为约1质量份~约10质量份,特别为约1.5质量份~约5质量份的范围内。而且,在所述水相部中,为了提高保存性,根据所需也可以添加:乳酸、柠檬酸、苹果酸、酒石酸等有机酸。
另外,(A)式(1)所表示的薄荷基醚类及所述各种香料只要为低浓度,则也可以为了溶解于作为(C)成分的糖类、一元醇或多元醇中,而调配于所述水相部中。
作为本发明中所使用的作为(D)成分的乳化剂,并无特別限制,可以使用自以往用于饮食品等中的各种乳化剂,例如可例示:脂肪酸单甘油酯、脂肪酸甘油二酯、脂肪酸甘油三酸酯、丙二醇脂肪酸酯、蔗糖脂肪酸酯、聚甘油脂肪酸酯、卵磷脂、化工淀粉、山梨糖醇酐脂肪酸酯、皂树萃取物、***胶、黄耆胶、瓜尔胶、刺梧桐树胶、三仙胶、果胶、海藻酸及其盐类、角叉菜胶、明胶、酪蛋白等。
该等乳化剂中,特别优选HLB为8以上的亲水性界面活性剂,在该情况时,在水相部中混合乳化剂。具体而言,可列举:聚甘油脂肪酸酯、山梨糖醇酐脂肪酸酯、蔗糖脂肪酸酯、甘油脂肪酸酯等。作为聚甘油脂肪酸酯类,例如可列举:平均聚合度3以上的聚甘油和碳数8以上的脂肪酸的酯,例如为十甘油单油酸酯、十甘油单硬脂酸酯、十甘油单棕榈酸酯、十甘油单肉豆蔻酸酯等且HLB为8以上、优选为8~14的范围内的聚甘油脂肪酸酯类。在使用HLB为8以上的聚甘油脂肪酸酯的情况下,通常易于制备均匀且粒径较小的乳化粒子,而且,若将乳化组合物稳定地添加于饮料中,则引起沉淀、油分离等分离现象的倾向低。
聚甘油脂肪酸酯醚类的含量相对于油相部1质量份,可以为通常为0.05质量份~0.5质量份,优选0.15质量份~0.3质量份的范围内。
若例示本发明的乳化组合物的制备法的一实施形态,则为如下所示。首先,将所述的油相部中所使用的包含(A)式(1)所表示的薄荷基醚类的原料进行混合,制备油相部1质量份。另外,通过制备将(B)水、(C)选自糖类、一元醇或多元醇中的一种以上、及(D)乳化剂进行混合溶解而成的溶液(水相部)约2~约50质量份(水分含量约0.5质量%~约10质量%),将油相部和水相部进行混合,使用均质搅拌机、胶体磨机、高压均质器等进行乳化处理,可以获得粒径约0.2μm~约2μm的极其微细且稳定性优异的乳化组合物。
在该乳化组合物中,可以该乳化组合物的质量作为基准,通常以0.01%~30%的浓度含有式(1)所表示的薄荷基醚类,作为下限值,优选可例示:0.02%,更优选0.05%,进一步优选可例示:0.1%,而且,作为上限值,优选可例示:10%,更优选可例示:5%,进一步优选可例示:2%,该等下限值和上限值可以任意的组合设定范围。
本发明的粉末组合物可以通过将所述乳化组合物进行干燥而获得。作为干燥方法,可例示:真空干燥、喷雾干燥、冷冻干燥等干燥方法。在干燥时,也可以在所述乳化组合物中进一步添加糊精类、淀粉类、天然胶类、糖类等其他赋形剂作为赋形剂。
在使用含有式(1)所表示的薄荷基醚类的乳化组合物或粉末组合物的情况下,相对于饮食品或香妆品,以质量基准计,作为式(1)所表示的薄荷基醚类,通常可以0.1ppm~300ppm的浓度含有,作为下限值,优选可例示:0.2ppm,更优选可例示:0.5ppm,进一步优选可例示:1ppm,而且,作为上限值,优选可例示:100ppm,更优选可例示:50ppm,进一步优选可例示:20ppm,该等下限值和上限值可以任意的组合而设定范围。通过以该浓度范围添加,可以对饮食品或香妆品赋予稍稍木质、辛辣且青草的香气,而且,可以对饮食品赋予柚皮苷的各种苦味,即和不制成乳化组合物的情况相比,赋予苦味的上升较慢且清爽且温和的苦味。
作为可以通过本发明的乳化组合物或粉末组合物而赋予香味或改良、增强香味的饮食品的具体例,可列举:可乐饮料、加入果汁的碳酸饮料、加入乳类的碳酸饮料等碳酸饮料类;果汁饮料、蔬菜饮料、运动饮料、蜂蜜饮料、豆乳、维生素补给饮料、矿物质补给饮料、营养饮料、滋养饮料、乳酸菌饮料、乳饮料等软饮料类;绿茶、红茶、乌龙茶、花草茶、奶茶、咖啡饮料等嗜好饮料类;烧酒掺苏打水、鸡尾酒饮料、发泡酒、果实酒、药酒等酒精饮料类;黄油、乳酪、牛奶、酸乳酪等乳制品;冰淇淋、乳酸冰淇淋、冰点心、酸乳酪、布丁、果冻、日常甜点等甜点类及用以制造该等的混合物类;焦糖、糖果、模压点心、脆饼、饼干、曲奇、馅饼、巧克力、休闲点心等甜食类及用以制造该等的糕点混合物等混合物类;面包、汤、各种即食食品等通常食品类;洁牙等口腔用组合物,但并无任何限定。
而且,作为可以通过本发明的乳化组合物或粉末组合物而增强稍稍木质、辛辣且青草的香气的香妆品的具体例,例如可列举:香水;洗发精、润丝精、发霜、发蜡等毛发护理制品;白粉、口红等化妆品类;洁面用肥皂、身体用肥皂、洗涤用肥皂、洗涤用洗剂、消毒用洗剂、防臭洗剂等保健、卫生用洗剂类;卫生抽纸、卫生纸等保健、卫生材料类;室内芳香剂、车内香水等芳香制品。
[实施例]
以下,根据实施例对本发明更具体地说明。另外,本发明并不限定于该等。实施例中,只要无特別说明,则记载为「%」为质量基准。
在实施例中,反应粗制物、精制物的测定是使用以下分析机器进行。
GC(Gas chromatography,气相层析)测定:GC-2014(岛津制作所公司制造)及积分仪C-R8A(岛津制作所公司制造)
GC测定用GC管柱:GL Science公司制造的TC-1(长度30m,内径0.53mm,液层膜厚1.50测微计)、GL Science公司制造的TC-1701(长度30m,内径0.53mm,液层膜厚1.00测微计)
GC/MS(Gas chromatography-mass spectrometry,气相层析/质谱仪)测定:5973N(Agilent公司制造)
GC/MS测定用GC管柱:GL Science公司制造的TC-1701(长度30m,内径0.25mm,液层膜厚0.25测微计)
NMR(nuclear magnetic resonance,核磁共振)测定:ECX-400A(JEOL RESONANCE公司制造)。
参考例1:4-薄荷基氧基-2-丁酮的制备
向经氮气置换的100mL烧瓶中添加l-薄荷脑(7.81g,50mmol)、二氯甲烷(50.0g)、三氟化硼二***错合物(0.71g,5mmol)并搅拌混合后,向其中添加甲基乙烯基酮(10.51g,,150mmol),直接在20℃下搅拌4天。将反应液注入到5%碳酸氢钠水溶液(30.0g)中并停止反应。使有机层分离后,将水层利用二氯甲烷(15.0g)提取2次,将对应的有机层利用饱和食盐水进行洗净,利用无水硫酸镁进行干燥。进行吸引过滤而将硫酸镁去除后,利用旋转蒸发器将溶剂蒸馏去除。通过将所获得的粗产物12.99g进行减压蒸馏,而获得4-薄荷基氧基-2-丁酮(参考品1:产量7.28g,产率64.3%,纯度99.1%)。
4-薄荷基氧基-2-丁酮(参考品1)的物性资料
沸点:85~88℃/0.1kPa
1H NMR(CDCl3,400MHz)δ0.74(d,3H,J=7.2Hz),0.81(m,1H),0.85(d,3H,J=7.2Hz),0.89(d,3H,J=6.4Hz),0.95(m,1H),1.16(m,1H),1.32(m,1H),1.60(m,2H),2.09(m,2H),2.16(s,3H),2.64(m,2H),3.01(dt,1H,J=4.0,6.4Hz),3.54(ddd,1H,J=9.6,6.8,6.0Hz),3.84(dt,1H,J=9.2,6.0Hz).
13C NMR(CDCl3,100MHz)δ16.30,20.97,22.39,23.41,25.66,30.57,31.55,34.60,40.29,44.24,48.24,63.51,79.58,207.69。
MS(EI,70eV)m/z 41(29),43(96),55(44),71(100),81(44),83(26),87(23),95(39),123(18),138(30),141(40),155(25),169(1),211(1),226(M+,0.2).
[α](20℃,D射线,c=2.04于CHCl3)=-80.8。
实施例1:含有4-薄荷基氧基-2-丁酮的乳化组合物的制备
作为油相部,将4-薄荷基氧基-2-丁酮(1.0g)、SAIB 9.0g及MCT(中链脂肪酸甘油三酸酯)9.0g混合溶解。另一方面,作为水相部,将甘油66g、离子交换水11g及十甘油单油酸酯(4.0g)混合溶解。将水相部和油相部通过乳化机MARKII(PRIMIX公司制造)以8000rpm进行搅拌混合,进行10分钟的乳化。利用离子交换水制作如2000倍稀释时的波长680nm下的吸光度成为0.2Abs的O/W型乳胶(本发明品1:4-薄荷基氧基-2-丁酮浓度1.0%)。
香气评价
在样品瓶中准备本发明品1的1%水溶液(本说明书中,在水溶液中也包含将本发明的乳化组合物添加于水中的水分散液),通过5名官能检查员,进行来自瓶口的香气评价及对香气评价用的含浸本发明品1的1%水溶液通过纸进行香气评价。
根据5名官能检查员的平均的评价结果:稍微木质且青草的香气
苦味评价
制备将4-薄荷基氧基-2-丁酮相对于99.5%乙醇溶解10(W/W)%而成的溶液(参考品2)。将本发明品1及参考品2利用纯水稀释,制备使4-薄荷基氧基-2-丁酮成为下述表1所示的浓度的溶液。对于各溶液,通过5名官能检查员,对直接放入口中时、进一步喝下时的苦味综合地评价。将苦味的强度设为以下的基准(完全感觉不到苦味=0点,稍稍感觉苦味=2点,有些感觉苦味=4点,明显感到苦味=6点,强烈感到苦味=8点,非常强烈感到苦味=10点),对于苦味的品质附上评价。将5名官能检查员的平均的评价结果示于下述表1。
[表1]
如所述表1所示,4-薄荷基氧基-2-丁酮的水溶液是评价为乙醇稀释品及乳化组合物均在1ppm~200ppm的范围感到苦味。在将乳化组合物稀释于水中的情况、和将乙醇溶液稀释于水中的情况的比较中,在同一浓度的4-薄荷基氧基-2-丁酮的水溶液中,苦味的强度虽然不那样有差,但将乳化组合物稀释于水中的情况和将乙醇溶液稀释于水中的情况相比,苦味的上升较慢,苦味更清爽且温和。而且,乳化组合物的苦味是使人想起柚皮苷的苦味的苦味的评价。
实施例2:含有4-薄荷基氧基-2-丁酮的乳化组合物的制备
作为水相部,将甘油81g、离子交换水14g及十甘油单油酸酯(4.0g)混合溶解。将水相部和4-薄荷基氧基-2-丁酮(1.0g)通过乳化机MARKII(PRIMIX公司制造)以8000rpm搅拌混合,进行10分钟的乳化。利用离子交换水制作如2000倍稀释时的波长680nm下的吸光度成为0.2Abs的O/W型乳胶(本发明品2:4-薄荷基氧基-2-丁酮浓度1.0%)。
实施例3:调配了食用油脂类的含有4-薄荷基氧基-2-丁酮的乳化组合物的制备
(2)
作为油相部,将4-薄荷基氧基-2-丁酮(1.0g)、SAIB 17.5g及MCT(中链脂肪酸甘油三酸酯;食用油脂类)17.5g混合溶解。另一方面,作为水相部,将甘油50g、离子交换水8g及十甘油单油酸酯(6.0g)混合溶解。将水相部和油相部通过乳化机MARKII(PRIMIX公司制造)以8000rpm搅拌混合,进行10分钟的乳化。利用离子交换水制作如2000倍稀释时的波长680nm下的吸光度成为0.2Abs的O/W型乳胶(本发明品3:4-薄荷基氧基-2-丁酮浓度1.0%)。
苦味评价
将所述本发明品1及参考品2及本发明品2及本发明品3利用纯水进行稀释,制备使4-薄荷基氧基-2-丁酮成为10ppm的溶液。对于各溶液,通过5名官能检查员,将直接含入口中时、进一步喝下时的苦味的上升和持续进行比较评价。将其平均的评价结果示于下述表2。
[表2]
如所述表2所示,确认到伴随乳化组合物中的食用油脂类的含量的增加,苦味的持续时间变长。
参考例2:2-甲基-4-薄荷基氧基-2-丁醇的制备
使安装了温度计、滴液漏斗的200mL烧瓶经氮气置换后,注入四氢呋喃(利用分子筛5A进行干燥,50mL)和氯化甲基镁的3.0M四氢呋喃溶液(21.7mL,65mmol),利用水浴进行冷卻。自滴液漏斗以将内温保持为30℃以下的速度向其中滴加将4-薄荷基氧基-2-丁酮(11.32g,50mmol)溶解于四氢呋喃(50mL)中的溶液。滴加结束后,直接在室温下搅拌3小时后,将反应液注入到25%氯化铵水溶液(100g)中,利用分液漏斗将有机相和水相部分离。将水相部利用叔丁基甲醚(30g)提取2次后,将对应的有机相利用饱和食盐水洗净。利用无水硫酸镁进行干燥后,利用旋转蒸发器将溶剂蒸馏去除。通过向所获得的粗产物12.54g中少量添加碳酸钠并减压蒸馏而获得2-甲基-4-薄荷基氧基-2-丁醇(参考品3:产量10.25g,产率84.6%,纯度98.2%)。
2-甲基-4-薄荷基氧基-2-丁醇(参考品3)的物性资料
沸点:87℃/0.1kPa
1H NMR(CDCl3,400MHz)δ0.76(d,3H,J=6.8Hz),0.79-0.88(m,2H),0.86(d,3H,J=6.8Hz),0.90(d,3H,J=6.8Hz),0.96(m,1H),1.18(m,1H),1.22(s,3H),1.22(s,3H),1.33(m,1H),1.61(m,2H),1.69(ddd,1H,J=14.4,6.8,4.4Hz),1.77(ddd,1H,J=14.4,7.6,4.4Hz),2.13(m,2H),3.03(dt,1H,J=4.4,10.8Hz),3.50(ddd,1H,J=9.2,6.8,4.4Hz),3.68(s,1H),3.89(ddd,1H,J=9.2,7.6,4.4Hz)。
13C NMR(CDCl3,100MHz)δ16.13,21.03,22.37,23.25,25.77,29.07,29.44,31.57,34.53,40.10,41.68,48.23,65.71,70.49,79.89。
MS(EI,70eV)m/z 41(63),43(59),55(73),57(49),59(55),67(20),69(100),71(90),81(50),83(96),87(21),89(23),95(37),97(22),101(23),123(17),138(39),139(55),155(17),157(22),167(1),181(1),224(1),227(1),242(M+,0.1)。
[α](20℃,D射线,c=2.05于CHCl3)=-85.4。
实施例4:含有2-甲基-4-薄荷基氧基-2-丁醇的乳化组合物的制备
作为油相部,将2-甲基-4-薄荷基氧基-2-丁醇(1.0g)、SAIB 9.0g及MCT(中链脂肪酸甘油三酸酯)9.0g混合溶解,作为水相部,将甘油66g、离子交换水11g及十甘油单油酸酯(4.0g)混合溶解,将两种溶液通过乳化机MARKII(PRIMIX公司制造)以8000rpm搅拌混合,进行10分钟的乳化。利用离子交换水制作如2000倍稀释时的波长680nm下的吸光度成为0.2Abs的O/W型乳胶(本发明品4:2-甲基-4-薄荷基氧基-2-丁醇浓度1.0%)。
香气评价
在样品瓶中准备本发明品4的1%水溶液,通过5名官能检查员,进行来自瓶口的香气评价及对含浸了香气评价液通过纸进行香气评价。
根据5名官能检查员的平均的评价结果:辛辣且青草的香气
苦味评价
制备将2-甲基-4-薄荷基氧基-2-丁醇在99.5%乙醇中溶解10(W/W)%而成的溶液(参考品4)。将本发明品4及参考品4利用纯水进行稀释,制备使2-甲基-4-薄荷基氧基-2-丁醇成为下述表3所示的浓度的溶液。针对各溶液,通过5名官能检查员,将直接含入口中时、进一步喝下时的苦味综合地评价。将苦味的强度设为以下的基准(完全感觉不到苦味=0分,稍稍感觉苦味=2分,有些感觉苦味=4分,明显感到苦味=6分,强烈感到苦味=8分,非常强烈感到苦味=10分),对于苦味的品质附上评价。将5名官能检查员的平均的评价结果示于下述表3。
[表3]
如所述表3所示,2-甲基-4-薄荷基氧基-2-丁醇的水溶液是评价为乙醇稀释品及乳化组合物均在0.5ppm~100ppm的范围感到苦味。在将乳化组合物稀释于水中的情况、和将乙醇溶液稀释于水中的情况的比较时,在同一浓度的4-薄荷基氧基-2-丁醇的水溶液中,苦味的强度不那样有差,将乳化组合物稀释于水中的情况和将乙醇溶液稀释于水中的情况相比,苦味的上升较慢、苦味更清爽且温和。而且,乳化组合物的苦味是让人想起柚皮苷的苦味的苦味的评价。
实施例5:对啤酒风味饮料的添加效果
向市售的啤酒风味饮料中,将本发明品1添加0.1%(4-薄荷基氧基-2-丁酮浓度10ppm)或将本发明品4添加0.1%(2-甲基-4-薄荷基氧基-2-丁醇浓度10ppm),分別通过5名官能检查员,就苦味、饮用口感、入喉、味道的爽口、余味的观点进行官能评价。其平均的官能评价结果是如下所述。
添加了本发明品1的啤酒风味饮料和无添加品相比,感到良好的苦味,而且,关于入喉及味道的爽口,感到显著的效果。而且,关于饮用口感,稍许增加,余味也改善一些。
添加了本发明品4的啤酒风味饮料和无添加品相比,感到良好的苦味,而且,关于入喉及味道的爽口,感到显著的效果。而且,关于饮用口感,稍许增加,余味也改善一些。
实施例6:橘子味调制香料组合物的乳化组合物
根据下述表4,制备参考品5~7的橘子味调制香料组合物。
[表4]
橘子味调制香料组合物配方(质量%)
参考品5 | 参考品6 | 参考品7 | |
酸橙油 | 70 | 70 | 70 |
卑宁油 | 5 | 5 | 5 |
橙花油 | 5 | 5 | 5 |
乙酸薰衣草酯 | 1 | 1 | 1 |
柠檬醛二甲缩醛 | 2 | 2 | 2 |
戊烯醇 | 1 | 1 | 1 |
朱乐倍半萜 | 0.5 | 0.5 | 0.5 |
四氢月桂烯醇 | 0.2 | 0.2 | 0.2 |
参考品1 | - | 50 | - |
参考品3 | - | - | 50 |
SAIB | 400 | 400 | 400 |
中链饱和脂肪酸甘油三酸酯 | 515.3 | 465.3 | 465.3 |
合计 | 1000 | 1000 | 1000 |
制备将作为油相部的所述表4的橘子风味调制香料组合物(参考品5、参考品6或参考品7)100g、作为水相部的甘油312.5g、离子交换水65g溶解于十甘油单硬脂酸酯22.5g中,将两种溶液通过乳化机MARKII(PRIMIX公司制造)以8000rpm搅拌混合,进行10分钟的乳化。获得利用离子交换水制作如2000倍稀释时的波长680nm下的吸光度成为0.2Abs的O/W型乳胶的橘子味调制香料组合物的乳化组合物。将参考品5的乳化组合物设为比较品1,将参考品6的乳化组合物设为本发明品5,将参考品7的乳化组合物设为本发明品6。
将各橘子味调制香料组合物的乳化组合物(比较品1、本发明品5及本发明品6)添加于下述表5所示的配方的饮料基材中,制备橘子果汁饮料。
[表5]
橘子果汁饮料(果汁30%)的配方
在香味评价中,选定熟练的官能检查员5名,对于饮食添加了比较品1、本发明品5或本发明品6的橘子果汁饮料时的苦味、和作为香味评价项目的橘子果汁饮料的果肉感、新鲜感、果皮感、成熟感进行评价。评价是以比较品1的香味作为基准,综合地评价将果汁饮料直接含入口中时、进一步喝下时的香味。苦味是设为以下的基准(完全未感到苦味=-分,未明确感到苦味=+/-分,感到苦味=+分,强烈感到苦味=++分,苦味过强=+++分),作为饮食时的香味评价,对于果肉感、新鲜感、果皮感、成熟感,用以下的基准(未感到=-分,未明确感到=+/-分,感到=+分,强烈感到=++分)进行评价。而且,记载香味评价的评价。将其平均的香味评价结果示于下述表6。
[表6]
橘子果汁饮料的香味评价
如所述表6所示,添加了本发明品5或6的橘子果汁饮料是再现具有天然感的橘子的风味。即,为赋予橘子的果皮感,强调联想到食用新鲜的生橘子时的香味的评价。
实施例7:薄荷味调制香料组合物的乳化组合物
依据下述表7,制备参考品8~10的薄荷味调制香料组合物(薄荷香料)。
[表7]
薄荷味调制香料组合物配方(质量%)
制备在作为油相部的所述表7的薄荷味调制香料组合物(参考品8、参考品9或参考品10)100g、作为水相部的甘油312.5g、离子交换水65g中溶解十甘油单硬脂酸酯22.5g,将两种溶液通过乳化机MARKII(PRIMIX公司制造)以8000rpm搅拌混合,进行10分钟的乳化,获得制成O/W型乳胶的薄荷味调制香料组合物的乳化组合物。将参考品8的乳化组合物设为比较品2,将参考品9的乳化组合物设为本发明品7,将参考品10的乳化组合物设为本发明品8。
将各薄荷味调制香料组合物的乳化组合物(本发明品7、8或比较品2)添加至下述表8所示的配方的橡胶基材中,依据常法制备薄荷风味口香糖。
[表8]
薄荷风味口香糖的调配配方:单位为质量%
在香味评价中,选定熟练的官能检查员5名,作为咀嚼添加了本发明品7、8或比较品2的薄荷风味口香糖时的香味评价项目,对薄荷风味口香糖的苦味、清凉感、花草茶感、天然感、化学品感进行评价。评价是以添加了比较品2作为基准,对开始咀嚼口香糖时、进一步咀嚼10分钟咀嚼时的香味综合地评价。苦味是设为以下的基准(完全未感到苦味=-分,未明确感到苦味=+/-分,感到苦味=+分,强烈感到苦味=++分,苦味过强=+++分),作为咀嚼时的香味评价,对清凉感、花草茶感、天然感、化学品感,用以下的基准(未感到=-分,未明确感到=+/-分,感到=+分,强烈感到=++分)进行评价。将香味评价示于下述表9。
[表9]
薄荷风味口香糖的香味评价
如所述表9所示,添加了比较品2的薄荷风味口香糖虽然清凉感较强,但苦味、花草茶感较弱,也有化学品感,缺乏天然感。相对于此,添加了本发明品7或8的薄荷风味口香糖是清爽的苦味和薄荷的清凉感一体化,赋予天然感,抑制了比较品2中所感到的化学品感的评价。
Claims (8)
1.一种乳化组合物,其含有下述(A)~(D):
(A)下述式(1)所表示的薄荷基醚类;
[化1]
[式(1)中,X表示部分结构式(1-a)或(1-b),R1及R2表示甲基、乙基、丙基或异丙基]
(B)水;
(C)选自糖类、一元醇或多元醇中的一种以上;及
(D)乳化剂。
2.根据权利要求1所述的乳化组合物,其进一步含有(E)食用油脂类。
3.根据权利要求1或2所述的乳化组合物,其中所述薄荷基醚类为下述式(2)所表示的2-甲基-4-薄荷基氧基-2-丁醇;
[化2]
4.一种粉末组合物,其是将根据权利要求1至3中任一项所述的乳化组合物干燥而成。
5.一种饮食品,其含有根据权利要求1至3中任一项所述的乳化组合物或根据权利要求4所述的粉末组合物。
6.一种香妆品,其含有根据权利要求1至3中任一项所述的乳化组合物或根据权利要求4所述的粉末组合物。
7.一种饮食品或香妆品的香气赋予或香气调变方法,其是通过含有根据权利要求1至3中任一项所述的乳化组合物或根据权利要求4所述的粉末组合物而进行。
8.一种饮食品的苦味赋予方法,其是通过根据权利要求1至3中任一项所述的乳化组合物或根据权利要求4所述的粉末组合物含有于饮食品中而进行。
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JP2016074574A JP6391179B2 (ja) | 2016-04-01 | 2016-04-01 | 乳化組成物および粉末組成物 |
PCT/JP2017/009371 WO2017169606A1 (ja) | 2016-04-01 | 2017-03-09 | 乳化組成物および粉末組成物 |
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TW201735898A (zh) | 2017-10-16 |
JP6391179B2 (ja) | 2018-09-19 |
US20190093047A1 (en) | 2019-03-28 |
WO2017169606A1 (ja) | 2017-10-05 |
JP2017184636A (ja) | 2017-10-12 |
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