CN1161034C - 1-壬烯-3-酮作为风味剂的用途 - Google Patents
1-壬烯-3-酮作为风味剂的用途 Download PDFInfo
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- CN1161034C CN1161034C CNB97198185XA CN97198185A CN1161034C CN 1161034 C CN1161034 C CN 1161034C CN B97198185X A CNB97198185X A CN B97198185XA CN 97198185 A CN97198185 A CN 97198185A CN 1161034 C CN1161034 C CN 1161034C
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- Prior art keywords
- methyl
- ketone
- nonene
- furanone
- ethyl
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Abstract
1-壬烯-3-酮作为风味剂给食品、化妆品、药物和香水组合物增香的用途。一种基本上由1-壬烯-3-酮和至少一种选自下组的分子组成的组合物,2,3-丁二酮,2,3-戊二酮,二甲硫,methional,2-甲基-四氢噻吩-3-酮,2E-壬烯醛,愈创木酚,甲基丙醛,2-甲基丁醛,3-甲基丁醛,2-和3-甲基-2-丁醛,2-和3-甲基丁酸,3-甲基-2-丁烯硫醇,2-甲基呋喃硫醇,2-糠基硫醇,3-巯基-3-甲基丁基甲酸酯,4-乙基愈创木酚,4-乙烯基愈创木酚,2-异丙基-3-甲氧基吡嗪,2,3-二乙基-5-甲基吡嗪,2-乙基-3,5-二甲基吡嗪,2-异丁基-3-甲氧基吡嗪,β-大马酮,香兰素,4-羟基-2,5-二甲基-3(2H)-呋喃酮,2-乙基-4-羟基-5-甲基-3(2H)-呋喃酮,3-羟基-4,5-二甲基-2(5H)-呋喃酮,和5-乙基-3-羟基-4-甲基-2(5H)呋喃酮。
Description
本发明涉及1-壬烯-3-酮作为风味剂,特别是给乳制品、咖啡提取物和胶囊中的化合物增香的用途。
发明背景技术
从五十年代开始人们就对酸奶挥发物产生了兴趣,至今已经从中确认了不止60种风味化合物(Maars等人,食品中的挥发化合物,TNO-CIVO,食品分析学会,荷兰,1994)。因其特殊结构有关的美味和乳酸菌对人体健康的有益作用,从六十年代起酸奶的消费日趋普遍。液上气体分析和同步蒸馏提取(SDE)通常被用来分析酸奶的风味。由于酸奶气味的强度较低,经常要将试样加热来增进风味的挥发(Ulberth等人,Assoc Off.Anal.Chem.,
74,630-634,1991)。这会改变这一敏感香气的组成,故必须采用温和的取样技术。采用低温净化-捕集取样法Laye和Imhof分别确认了23和33种化合物(Laye等人,食品科学,
58,991-995,1993;Imhof等人,Lebensm.Wiss.u-Technol.,27,265-269,1994),但是没有人测定出对典型的酸奶香气起关键作用的挥发物。最近,Imhof等人提议2,3-丁二酮,2,3-戊二酮,二甲硫和苯甲醛是酸奶香气的最有效成分(Lebensm.Wiss.u-Technol.,28,78-86,1995)。
在咖啡提取物中,Semmelroch等人鉴定出,作为有用的芳香成分,2-甲基丙醛,2-甲基丁醛,2,3-丁二酮,2,3-戊二酮,3-甲基-2-丁醛和愈创木酚(Lebensm-Wiss.u-Technol,
28,310-313,1995)。
另一方面,已由氯铬酸吡啶鎓氧化相应的醇合成出1-壬烯-3-酮(Corey等人,Tetrahedron Letters,31,2647-2650,1975;Nakahira等人,J.有机化学,
57,17-28,1992)。用国际风味工业组织(International Organisation of the Flavour Industry)确认的方法尚未从食品中鉴定出1-壬烯-3-酮(Z.Lebensm.u-Forsch,
192,530-534,1991)。
本发明的目的是提供一种与其他风味剂相结合,包括在食品特别是乳制品和咖啡衍生产品的风味物质中的化合物。
发明概述
因此,本发明提供了1-壬烯-3-酮作为风味剂,特别是给食品、化妆品、药物和香水组合物增香的用途。
本发明还提供了给食品、化妆品、药物和香水组合物增香的方法,包括向组成中添加有效量的1-壬烯-3-酮。
另一方面,本发明提供了一种包括用多糖包胶的1-壬烯-3-酮的粉末组合物。
最后,本发明还提供了任何基本上由1-壬烯-3-酮和至少一种已知包括在乳制品或咖啡芳香物中的分子组成的组合物,这些分子选自2,3-丁二酮,2,3-戊二酮,二甲硫,麦思诺(methional),2-甲基-四氢噻吩-3-酮,2E-壬烯醛(nonenal),愈创木酚,甲基丙醛,2-甲基丁醛,3-甲基丁醛,2-和3-甲基-2-丁醛,2-和3-甲基丁酸,3-甲基-2-丁烯硫醇,2-甲基呋喃硫醇,2-糠基硫醇,3-巯基-3-甲基丁基甲酸酯,4-乙基愈创木酚,4-乙烯基愈创木酚,2-异丙基-3-甲氧基吡嗪,2,3-二乙基-5-甲基吡嗪,2-乙基-3,5-二甲基吡嗪,2-异丁基-3-甲氧基吡嗪,β-大马酮,香兰素,4-羟基-2,5-二甲基-3(2H)-呋喃酮,2-乙基-4-羟基-5-甲基-3(2H)-呋喃酮,3-羟基-4,5-二甲基-2(5H)-呋喃酮,和5-乙基-3-羟基-4-甲基-2(5H)呋喃酮。
附图说明
结合附图举例说明本发明的实施方案,其中:
图1:酸奶芳香物的NIF曲线(峰顶保留指数),
图2:1-壬烯-3-酮的质谱(A:EI电离波谱;B:阴极CI波谱)
图3:在m/z 139用SRM从[M-H]-离子得到的子离子69的GC/MS/MS色谱;下面的曲线:50pg参照化合物;上面的曲线:5μl酸奶提取物,
图4:空白试验的NIF曲线(加有蒸馏水的液上气体小室),
图5:1-壬烯-3-酮极限的测定值(C:浓度以ng/kg计),
图6:煮咖啡香味的NIF曲线,
发明详述
用连接的气相色谱-气味测量技术能够直接测定食品中的有效气味物质。最常用的方法是Charm分析(Acree等人,气相色谱洗脱剂中呈味挥发物的分析,挥发物分析,de Gruyter,纽约,1984)和芳香提取物稀释分析法(AEDA),(Ullrich和Grosch;Z.Lebensm.Unters.Forsch.,184,277-282,1987)。这两种方法都基于被稀释到嗅口无可感觉气味的芳香提取物的GC气味测定。最近Grosch集团得到了食品周围的液上气体:其组成更能代表消费者感觉到的气味(Semmelroch和Grosch,Lebensm.Wiss.u-Technol,28,310-313,1995)。
由于在打开酸奶瓶或在咖啡杯上方首先被人感觉到的是蒸汽相的气味,其质量会影响消费者的选择。由于鼻后感觉对酸奶释放出的液上气体气味也敏感,因此最好把注意力集中于液上气体并通过直接测定其中各个有效成分来确定主要的呈味物质。但是,作为至关重要的评价,稀释嗅觉法存在着再现性问题(Abbott等人,J.Agric.食品化学,
41,1698-1703,1993)。
要确定食品中的风味物质只能使用一种稀释浓度,GC-气味测量法可以重复数次。然后各个芳香物质的芳香克数被“平均”以消除上述再现性问题。所得的芳香克数可以使气味曲线按照与气味测定频率有关的峰强来进行对比:“NIF”和“SNIF”(分别是“鼻有效频率”和“鼻表面有效频率”;Ott等人,改进的液上气体-GC-嗅觉技术;呈香物质的筛选,4th Int.Symposium on Hyphenated Techniques inChromatography,Bruges,比利时,1996)。
下文中的“操作1c”方法是对酸奶和煮咖啡中1-壬烯-3-酮和其他风味化合物的第一次测定。1-壬烯-3-酮的气味极限为约8pg/kg。这一极低的极限将1-壬烯-3-酮归为至今从风味物中辨认出来的最有效的一类化合物。
乳制品和煮咖啡中的许多风味分子是已知的。这些分子中的任何一个都不能代表乳品或咖啡的风味。是这些风味分子的结合导致了典型的乳品或咖啡风味。同样,1-壬烯-3-酮代表了蘑菇味,但当与其他的乳品或咖啡风味分子结合时,它增强了最终被消费者感觉到的风味。因此,本发明还包括任何基本上由1-壬烯-3-酮和包括在乳品和咖啡香味中的风味分子所组成的风味组合物,所述的分子可以选自上面列出的风味分子或在实施例中介绍的风味分子。
向乳品中添加0.1ppt-1ppm的1-壬烯-3-酮可以令人惊异地提高乳品的芳香的实际效果。把1-壬烯-3-酮添加到煮咖啡中得到了同样的观察结果。向酸奶中添加0.1ppt-20ppt的1-壬烯-3-酮将得到最好的效果。根据本发明的用途还涉及任何将1-壬烯-3-酮用在经加工形成加工风味的混合物中作为风味成分的用途。
也可以在转化之后,将多糖溶液添加到反应混合物中,然后将混合物冷冻干燥。多糖可以是如环糊精或麦芽糊精。所得的粉末可含有多至10wt%的1-壬烯-3-酮,由于包胶使该化合物稳定,此粉末也是本发明的目的产物。这种粉末有利于,例如以上述的量添加到食品、化妆品、药物或香水组合物中。
下面通过实施例进一步说明本发明,但不对其进行限制。实施例为包括在食品中的风味分子的特征和1-壬烯-3-酮给食品增香的用途。这些实施例通过许多试验来陈述。除非特别说明,所有的份数、比例及百分数均以重量计,并参考附图。
试验-操作1a-动态液上气体/GC/MS:将10g酸奶样品分散到5mL饱和盐水中并装入净化-捕集系统(Tekmar Co.,Cincinnati,OH)的分布器中。在5-99min的时间里以流速为40-60mL/min的超纯氮气将试样净化。从Tenax上将挥发物热解析(180℃,4min),冷凝(cryofocussed)并注射到HP 5995 GC/MS(HewlettPackard,Avondale PA)中,其中装有FFAP(SupelcoInc.,Bellefonte,PA)柱,30m长,内径0.25mm,相厚0.25mm。用流速0.65mL/min的氦气作为载体气体。将柱保持在20℃下1.0min,以4℃/min的速度从20℃升至200℃,在200℃保持1min。端口温度220℃、电离电位70eV下得到质谱。将确定出的化合物质谱和保留指数与用户手册(user-generated libraries)中的作对比。在相同条件下注射正烷烃系列(C5-C17)后测定线性保留指数(Van den Dool和Kratz,J.Chromatogr.,
11,463-471,1963)。
试验-操作1b-液上气体-捕集/GC/MS:将100g酸奶和16g蒸馏水倒入容积500mL的3颈容器中,恒温到30℃并迅速用磁棒搅拌。用流速为30mL/min的超纯氦气净化挥发物并捕集在Tenax管上60min。于250℃用TD-2热解析塔(Scientific Instruments ServicesInc.,Ringoes,NJ)从Tenax上将挥发物热解析(250℃,5min)。冷凝并注射到HP 5890 GC(Hewlett Packard,Avondale PA)中,其中装有DB-wax柱(J&W Scientific,folsom,CA),(30m长,内径0.25mm,相厚0.25mm)。用流速0.65mL/min的氦气作为载体气体。将柱保持在20℃下5min,以4℃/min的速度升至200℃,保持10min。直接将柱与在上述相同条件下以扫描或SIM模式操作的HP5971质谱仪的EI端口连接。化合物的确定标准与上述的相同。
试验-操作1c-顶部空间小室/GC/嗅觉或/FID:使用Chaintreau等人阐述的测定分隔系数的顶部空间小室(Anal.Chem.,
67,3300-3304,1995)。由模板混合物建立起再现性,当用来定量测定气相时系统具有很好的精确度。在端口处,将25g酸奶或1g煮咖啡放在顶部空间小室的试样槽中,在30℃水浴下平衡2小时。小室(160mL)的气体通过含有250mg以流速40mL/min的Tenax的捕集器。用ATD400热解析塔(Perkin-Elmer Corp.,Norwalk,CT)从Tenax上将挥发物热解析(300℃,15min)。挥发物重新集中在内部冷却的Tenax捕集器中(-30℃)并在300℃下解析3分钟到HP 5890 GC(HewlettPackard,Ayondale PA)中,其中装有DB-wax柱(J&W Scientific,folsom,CA),(60m长,内径0.53mm,相厚1.00mm)。用流速10.6mL/min的氦气作为载体气体。将柱保持在20℃下5min,以4℃/min的速度升至200℃,保持10min。柱的出口或与FID相连或与配有湿空气补偿的嗅闻端口(Brechbuhler SA,Plan-les-Ouates,Switzerland)相连。每次取样之后,在50℃、100mbar的真空箱内将槽清洁至少一小时。Tenax样品管在使用之前加热到300℃在氦气流(50mL/min)下清洁一小时。
选择八位对GC气味测定法有经验的人。色谱的嗅闻分为约25分钟的两部分。每个人都参加两部分的色谱的嗅闻,但分在两个感觉部分里。在整个感觉印象中通过按按钮来记录洗脱的有关气味的风味物质。方块记号由HP Pascal工作站记录。此外,气味仪将每个峰记录在记录纸上。用国产软件将8个单独试样的芳香克数汇总成一个色谱图,得到平均的芳香克数。按上述方法计算线性保留指数。由GC/MS确认的化合物再注射到GC/嗅觉系统中核对它们的保留指数。如果需要可对它们的气味质量进行对比。
试验-操作2-真空转移:根据Bemelmans的方法(风味研究的方法,D.G.Land & H.E.Nursten,应用科学,伦敦,79-98,1979),用700mL新蒸馏的二乙醚在Soxhlet设备中提取100g冷冻干燥的酸奶30h。在10-3mbar下通过高真空转移从提取物中脱出脂肪并在液氮温度下收集。在Vigreux柱上将冷凝物浓缩到3mL。用1mL 0.5M Na2CO3溶液提取浓缩物3遍并用1mL饱和NaCl溶液洗涤3遍。用Na2SO4干燥该醚提取物并用微蒸馏设备(Bemelmans)浓缩到100mL。用1N HCl酸化含水馏分,并用10mL蒸馏二乙醚提取3次。用3×10mL饱和NaCl溶液洗涤醚提取物,Na2SO4干燥。用微蒸馏设备将提取物浓缩到100mL。
试验-操作3-真空SDE:将2kg酸奶分散在事先脱气并用盐饱和的水中。按报道的连续进样方法(Chaintreau等人,欧洲专利申请952034965),用预备设备在40mbar下SDE提取分散液7小时。用新蒸馏的丁基乙基醚(5ml)(Fluka AG,Buchs Switzerland)作为溶剂。样品瓶、样品槽和溶剂瓶中的操作温度分别为39℃、15℃和9.5℃。所得的有机提取物(约1ml)不经预浓缩直接用于GC-MS。
试验-气相色谱串联质谱GC/MS/MS:用Finnigan MAT TSQ-700质谱仪(San Jose,CA)得到质谱,连接一个HP-5890气相色谱。柱为DB-wax柱(J&W Scientific,folsom,CA),30m长,内径0.32mm,相厚0.25mm。在10psi下用氦气作为载体气体。将柱在60℃下保持1min,以15℃/min的速度升至240℃,保持2min。用氨水作为试剂进行正负化学电离分别产生[M+NH4]+离子或[M-H]-离子,用碰撞引诱离解试验来进行分析。实验室碰撞能量为6eV,氩气作为碰撞气体设为1mTorr。
对比例
在从本地零售商购得的经巴氏消毒的全脂乳(OrlaitSA,Lausanne,Switzerland)中增加2.5%的脱脂乳粉并在98℃下加热处理15分钟,立即在水浴中冷却到约35℃,接种唾液链球菌嗜热亚种和德氏乳杆菌保加利亚亚种发酵剂培养物。将所得溶液放在150mL无菌罐中,密封并在41℃下发酵5小时(直至pH=4.2)。终止发酵后立即将酸奶样品冷却到4℃并在分析前于此温度下储存2周。
在制备2周之后对酸奶进行分析,因为已知风味主要是在发酵步骤中产生的且在4℃下冷藏不会明显变化。用上述的3种不同的温和取样方法即操作1a,操作1b,操作2从基质中分离出风味物质。
结果显示出所确认出的86种化合物是已知存在于酸奶配方中的酸奶、乳或脱脂乳粉中的成分。在新确认出的化合物中,有一些对总的香味有贡献:1-戊烯-3-醇,3-辛酮,2-甲基四氢呋喃-3-酮,3-甲基-2-丁烯醇,2-甲基四氢噻吩-3-酮,和2-甲基丙酸。但是这些方法不足以确定1-壬烯-3-酮。
实施例1
使用对比例中所述的酸奶,用液上气体取样操作1c经8次嗅闻,如上所述,建立酸奶风味的SNIF图。对每个液上气体试样进行相同的发酵方法产生酸奶。结果列于图1和表1。
测出了21种对总香气有贡献的主要物质。其中,只有11种与对比例中提到的用3种操作方法确定的挥发物相对应。在GC和感觉中枢的特点基础上,通过对比保留指数和气味描述提议了7种其他化合物的特性,它们的保留指数通过在相同条件下用FID测定仪重注射真实试样来核对。
表1
保留指数(l) | 保留指数(ref) | 描述 | 数据库提出的识别和描述 |
716 | 710 | 新鲜,生,刺激 | 乙醛:新鲜,水果,刺激,醚 |
757 | 754 | 乳,内酯状,硫磺气,温暖 | 二甲硫:硫,烘烤的 |
995 | 993 | 奶油,二乙醚,香兰素 | 2,3-丁二酮:奶油,脂肪,油,香兰素 |
1082 | 1082 | 奶油,香兰素,柔和 | 2,3-戊二酮:奶油,焦糖 |
1120 | 1109 | 汽油,塑料,苯乙烯 | 2-甲基-噻吩:汽油,洋葱状,石蜡 |
1221 | 1222 | 金属,醛,草 | 3-甲基-2-丁醛:醛酸,辛酸,刺激 |
1322 | 1324 | 蘑菇,土 | 1-壬烯-3-酮:蘑菇 |
1406 | 1403 | 硫,H2S,faecal | 二甲基三硫化物:强硫味,卷心菜,葱 |
1424 | 1425 | 蘑菇,土 | 无数据 |
1462 | 1460 | 刺激,酸,醋 | 乙酸:酸,像醋 |
1479 | 1479 | 汤,蒸煮过的蔬菜,刺激,硫 | methional:醛酸,辛酸,像蒸煮过的土豆,生,硫 |
表1(续)
1551 | 1557 | 生,皮革,硫 | 2E-壬烯醛+2-甲基四氢噻吩-3-酮:脂肪,生,刺激,皮革 |
1680 | 1678 | 花 | 2-苯基乙醛:花,像蜜 |
1684 | 1688 | 汗,花,奶酪,酱油 | 3-甲基丁酸:酸,像奶酪 |
1715 | 无数据 | 花,温暖,焦糖 | 无数据 |
1750 | 无数据 | 金属的 | 无数据 |
1882 | 1862-1885 | 酸败,花 | 己酸:酸,辛酸,脂肪 |
1896 | 1894 | 腌肉,酚,烟熏,辛辣 | 愈创木酚:芳香,烧过,酚的,辛辣 |
2002 | 2000 | 烧过,橡胶 | 苯并噻唑:烘烤,橡胶 |
2043 | 无数据 | 碳氢化合物,化学物,烧过的橡胶 | 无数据 |
(1)在DBWAX相上的保留指数,用液上气体注射(操作1c)。
感觉数据库的识别意见被表2中描述的方法制备试样,然后通过操作1a的GC/MS试验或上述GC/MS/MS试验所证实。结果列于表2。
由于每种化合物的量较低,不能在每一情况下用质谱获得完全的扫描谱。因此,用电子碰撞后产生的特殊离子的选择性离子监视(SIM)或通过碰撞引诱离解来对化合物进行选择性的分析。原始的[M+NH4]+或[M-H]-分别是正负化学电离产生的。此时,如果在相同保留时间时从GC柱上洗脱,记录每个化合物的特征子离子(选择性反应监视(SRM)试验)作为参考分子。
表2
化合物 | 保留指数(a) | 取样(b) | 质谱试验 |
1-辛烯-3-酮 | 1322 | 操作3 | GC/MS/MS,CI上SIM |
1-壬烯-3-酮 | 1424 | 操作3 | GC/MS/MS,CI上SIM |
Methional | 1479 | 操作3 | GC/MS,EI上SIM |
2-甲基-四氢噻吩-3-酮 | 1551 | 操作1b | GC/MS,EI上完全扫描 |
2E-壬烯醛 | 1551 | 操作1c | DBWAX上保留指数和 |
SPB-1 | |||
苯基乙醛 | 1682 | 操作2和3 | GC/MS-EI上SIM |
愈创木酚 | 1896 | 操作3 | GC/MS/MS,EI上SIM |
(a)嗅闻得到的指数。
(b)制备试样的方法。
作为例子图2A示意了1-壬烯-3-酮的电子碰撞电离质谱,图2B是它的碰撞引诱[M-H]-离解后的质谱。从其在m/z 139的母离子监视m/z 69的子离子后在酸奶提取物中找1-壬烯-3-酮。所得的酸奶提取物和参照的标准化合物的GC/MS/MS踪迹示于图3。
表2的7种风味物中,5种(1-壬烯-3-酮,methional,2-甲基-四氢噻吩-3-酮,2E-壬烯醛和愈创木酚)是首次从酸奶风味中辨认出来的。
将蒸馏水代替酸奶放在顶部空间槽中进行空白试验。测定出某些与酸奶中发现的物质相应的峰,但强度较低(图4)。由于不用Tenax捕集(取样操作2和3)也发现了3-甲基丁酸和己酸,所以它们不是人为的。此外,所有的空白试验峰,除了1-壬烯-3-酮,都已经在乳和/或酸奶中提到了。所以,图1的气味贡献物是从酸奶风味本身中产生的。
特别注意了1-壬烯-3-酮,因为从来没有这一化合物存在于任何风味中的具体证据。还没有肯定地从任何食品风味中鉴定出1-壬烯-3-酮,这一化合物也不能商购到。即使是相应的醇,1-壬烯-3-醇,似乎也不是普遍的风味成分:只有三种天然存在的情况被报道过:香叶芹,牛肉脂肪和香蕉(Maarse等人,1994,见上)。
然后制备参照样品来说明其感官和分析性质。通过用氯铬酸吡啶鎓氧化相应的醇制得1-壬烯-3-酮(Corey和Suggs,1975,见上),并用制备性HPLC提纯。MS,1H和13C NMR波谱与已公开的数据(Nakahira等人,1992,见上)一致。
除了质谱(图2),还测定它在不同相上的保留指数(表3)。根据图3中参照化合物的量,酸奶中1-壬烯-3-酮的浓度似乎为2-5ppt。由于还在空白嗅闻试验中测定1-壬烯-3-酮,因此可以假定Tenax降解可以产生这一化合物,就像在Bravo的聚乙烯降解试验(J.Agric.Food.Chem.,40,1881-1885,1992)中那样。又由于在SDE提取(操作3)上进行的肯定的特别鉴定,这一假设被排除了。
表3:在某些食品风味中1-壬烯-3-酮的保留指数和气味描述
试样 | DB-Wax | SE-54 | FFAP | OV-1701 | SPB1 | 描述 |
1-壬烯-3-酮(真实) | 1400(a)1425(b) | 1080(a) | 1398(a) | 1171(a) | 1070(a)1065(b) | 蘑菇,土味 |
酸奶 | 1424(b) | - | - | - | 1065(b) | 蘑菇,土味 |
煮咖啡(见实施例4) | 1427(b) | - | - | - | 1061(b) | 蘑菇,土味 |
(a)以溶液形式注射的1-壬烯-3-酮
(b)Tenax上吸收的1-壬烯-3-酮,用ATD400系统注射
实施例2
用三角试验形式测量1-壬烯-3-酮的嗅觉极限。将几组三个样品一组的、装有35ml液体的65ml容积称量瓶给21位有经验的人员。一个试样是刺激物溶解在矿泉水中(Vittel),另外两个是矿泉水。对每一评价,给五组提高了刺激物浓度的不同组,评价人必须指出哪个试样与另两个不同。全部过程在室温下(21℃)进行。玻璃容器在使用之前用2%RBS(Fluka AG Buchs,Switzerland)水溶液洗涤,然后用去离子水和蒸馏水漂洗。使用之前所有的玻璃材料在50℃、100mbar的真空箱内至少储藏过夜。用曲线拟合软件Windows“表格曲线2D”(Jandel scientific,Erkrath,Germany)将表示浓度对数函数的机率等式调节到实验数据。
通过嗅闻水溶液的几组三角试验测定极限值,按报道的方法整理评价人的意见(Voirol和Daget,Lebensm.Wiss.u-Technol.,
19,316-319,1986)。在被迫选择回答的情况下,某些正确回答是偶然的。因此用下式校正结果:
%感觉=%正确回答-(1-%正确回答)/2
用Bliss建立的表(Bliss,Statistics in Biology。McGraw-Hill:伦敦,1967)将感觉百分数转化成机率值。将机率值对浓度对数画图。经计算得出定义为感觉极限值的50%感觉值(或机率值5)为8pg/kg(图5)。
这一极低的极限值将1-壬烯-3-酮归为至今从食品风味和异味中辨认出来的最有效的一类化合物(表4)。所以,它在任何风味剂中的浓度必须非常低,这也就是为什么它的确认至今没有得到证实。
表4:最有效的风味物和异味物
化合物 | 气味极限值(pg/kg) | 参考 |
2,3,6-三氯茴香醚 | 0.3 | Bwender等人,1995 |
2,3,6-三溴茴香醚 | 8 | Bwender等人,1995 |
1-壬烯-3-酮 | 8 | 本发明 |
2(5H)-呋喃酮,5-乙基,3-羟基,4-甲基 | 10 | Kobayashi等人,1989 |
2-异丁基-3-甲基吡嗪 | 20 | Ewender等人,1995 |
Kobayashi等人,1989:Sotolon鉴定,形成和对风味的影响,风味化学,趋势和发展,ACS Symp.series 388,ACS,华盛顿DC,49-59。
Ewender等人,1995:食品包装反应引起的感觉问题:目前情况研究的综述和处理。食品和包装材料。Ackermann.Royal Society ofChemistry。伦敦:1995,33-44。
实施例3
将通过用氯铬酸吡啶鎓氧化相应的醇制得(Corey和Suggs,1975,见上),并用制备性HPLC提纯的1-壬烯-3-酮以水溶液(1ppb)的形式加入到发酵产生了柔和的弱酸味的全脂酸奶中得到最终在终产品的浓度:为0.5、10和20ppt。所有的试样加水校正并随机地与没有添加1-壬烯-3-酮的标准试样配组。请13位品评人给出他们对试样的感觉,按1-5排列。
结果表明添加0.5、5和10ppt给出了令人愉快的、奶油状酸奶,比标准的更让人喜欢。20ppt的浓度对于获得好效果来说是太高了。
实施例4
咖啡混合物的组成如下:50%哥伦比亚咖啡豆,50%Honduras咖啡豆。
按通方法常焙烤咖啡混合物5分钟。用Minolta和Neubaus设备分别测定其颜色为9.1和75.用4%水淬火。在-40℃下储存焙烤咖啡直至使用。分析之前用国产咖啡机(Turmix,“Gold Filter 720”)将咖啡豆磨碎和煮制(17g加200ml Vittel水,“Grande Source”)。
用上述的液上气体取样操作1c建立煮咖啡的SNIF曲线。感觉数据的识别建议被上述GC/MS/MS试验所证实。结果列于下面的表5和图6。
表5
保留指数(1) | 描述 | 化合物 |
755 | 芳香,塑料 | |
821 | 酮,醛,气体,etheral,choco-麦芽,咖啡 | 2-甲基丙醛 |
826 | 胶 | |
923 | 巧克力,麦芽,脚,醛 | 2-甲基丁醛 |
927-30 | 巧克力,麦芽,脚,醛 | 3-甲基丁醛 |
994-7 | 花,奶油 | 2,3-丁二酮 |
1072 | 咖啡 | |
1081 | 奶油,焦糖 | 2,3-戊二酮 |
1120 | etheral,塑料,丙烯酸的,1-戊烯-3-酮 | |
1223 | 刺激 | 3-甲基-2-丁醛 |
1322 | 蘑菇 | 1-辛烯-3-酮 |
1325 | 气体 | 2-甲基-3-呋喃硫醇 |
1329 | 发霉,吡嗪,烤杏仁 | |
1406 | 硫,新鲜,塑料,气体 | 二甲基-三硫化物 |
1427 | 塑料,蘑菇 | 1-壬烯-3-酮 |
1457-8 | 豌豆,发霉,吡嗪,烧过的面包皮 | 糠基硫醇+2-MeO-3-i-Pr-吡嗪 |
1481 | 发霉 | Methional |
1519 | 烤杏仁,吡嗪,etheral,发霉的纸 | 2,3-二乙基,5-甲基吡嗪 |
1529 | 吡嗪,噻唑 | |
1551 | 汽油,灰尘,土,噻唑/硫,吡嗪 | 2-异丁基,3-甲氧基吡嗪 |
1560 | 脂肪,生 | |
1587 | 吡嗪,噻唑 |
表5(续)
1622 | Etheral,发霉 | |
1586 | 蜜,花,蘑菇,硫 | 2和3-甲基丁酸 |
1715 | 气体,硫,煮硬的蛋,穆哈上等咖啡,苯 | |
1729-34 | 脂肪,炸制食品,碎屑 | |
1750 | 烯烃,蘑菇,发霉,鱼-胺,etheral | |
1858 | 变褐苹果,酒,水果minty | |
1885 | Etheral,咖啡 | |
1896 | 烟,药物 | 愈创木酚 |
2006 | 酒,过氧化氢 |
(1)在DBWAX相上的保留指数,用液上气体注射(操作1c)。
Claims (7)
1.1-壬烯-3-酮作为风味剂的用途。
2.根据权利要求1的用途,给食品组合物增香。
3.根据权利要求2的用途,给乳制品和咖啡提取物增香。
4.给食品组合物增香的方法,包括向组合物中添加1-壬烯-3-酮。
5.根据权利要求4的方法,其中向组合物中添加0.1ppt-1ppm。
6.根据权利要求1的用途,包括用多糖包胶的1-壬烯-3-酮。
7.根据权利要求1的用途,基本上由1-壬烯-3-酮和至少一种选自下组的分子组成,2,3-丁二酮,2,3-戊二酮,二甲硫,麦思诺,2-甲基-四氢噻吩-3-酮,2E-壬烯醛,愈创木酚,甲基丙醛,2-甲基丁醛,3-甲基丁醛,2-和3-甲基-2-丁醛,2-和3-甲基丁酸,3-甲基-2-丁烯硫醇,2-甲基呋喃硫醇,2-糠基硫醇,3-巯基-3-甲基丁基甲酸酯,4-乙基愈创木酚,4-乙烯基愈创木酚,2-异丙基-3-甲氧基吡嗪,2,3-二乙基-5-甲基吡嗪,2-乙基-3,5-二甲基吡嗪,2-异丁基-3-甲氧基吡嗪,β-大马酮,香兰素,4-羟基-2,5-二甲基-3(2H)-呋喃酮,2-乙基-4-羟基-5-甲基-3(2H)-呋喃酮,3-羟基-4,5-二甲基-2(5H)-呋喃酮,和5-乙基-3-羟基-4-甲基-2(5H)呋喃酮。
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CNB97198185XA Expired - Fee Related CN1161034C (zh) | 1996-08-02 | 1997-07-22 | 1-壬烯-3-酮作为风味剂的用途 |
CNA2004100485140A Pending CN1575790A (zh) | 1996-08-02 | 1997-07-22 | 1-壬烯-3-酮作为风味剂的用途 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
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CNA2004100485140A Pending CN1575790A (zh) | 1996-08-02 | 1997-07-22 | 1-壬烯-3-酮作为风味剂的用途 |
Country Status (13)
Country | Link |
---|---|
US (1) | US6296889B1 (zh) |
EP (1) | EP1006813B1 (zh) |
JP (1) | JP2000516645A (zh) |
CN (2) | CN1161034C (zh) |
AR (1) | AR008145A1 (zh) |
AT (1) | ATE288207T1 (zh) |
AU (1) | AU735054B2 (zh) |
BR (1) | BR9711001A (zh) |
CA (1) | CA2262462C (zh) |
DE (1) | DE69732435T2 (zh) |
ES (1) | ES2237799T3 (zh) |
NZ (1) | NZ333966A (zh) |
WO (1) | WO1998005220A1 (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102584653A (zh) * | 2011-12-15 | 2012-07-18 | 华宝食用香精香料(上海)有限公司 | 一种新型烤香香料的制作方法、其产品及用途 |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19837066A1 (de) * | 1998-08-17 | 2000-02-24 | Haarmann & Reimer Gmbh | Odorierung von Gas |
ATE288686T1 (de) * | 1998-11-04 | 2005-02-15 | Firmenich & Cie | Festes zuführsystem für aromazutaten |
GB9903216D0 (en) * | 1999-02-13 | 1999-04-07 | Zylepsis Ltd | Preservative compounds,compositions and methods of making and using the same |
JP2003079336A (ja) * | 2001-09-10 | 2003-03-18 | Ajinomoto Co Inc | 風味原料素材、及びそれを含有する飲食品 |
US20030165587A1 (en) * | 2002-02-28 | 2003-09-04 | Givaudan Sa | Production of 2-furfurylthiol in brassica seed and use of same |
EP1859685A1 (en) * | 2006-05-22 | 2007-11-28 | Drie Mollen Holding B.V. | Coffee bag |
US20090305943A1 (en) * | 2006-07-18 | 2009-12-10 | Sven Siegel | Cyclodextrin blends with crystal growth inhibitors |
AU2007313630B2 (en) | 2006-10-31 | 2013-07-04 | Bio-Tec Environmental, Llc | Chemical additives to make polymeric materials biodegradable |
US8513329B2 (en) | 2006-10-31 | 2013-08-20 | Bio-Tec Environmental, Llc | Chemical additives to make polymeric materials biodegradable |
WO2008138547A2 (en) * | 2007-05-11 | 2008-11-20 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Improved infant formula containing an aroma composition for use as fragrance |
US20100102142A1 (en) * | 2008-10-28 | 2010-04-29 | Daria Tagliareni | Scent dispenser assembly |
WO2010125770A1 (ja) * | 2009-04-28 | 2010-11-04 | 花王株式会社 | 濃縮コーヒー抽出液 |
WO2013080357A1 (ja) * | 2011-12-01 | 2013-06-06 | アサヒビール株式会社 | 非発酵ビールテイスト飲料及びその製造方法 |
EP2958441A1 (en) | 2013-02-21 | 2015-12-30 | Mars, Incorporated | Mango flavor compositions |
JP2017112880A (ja) * | 2015-12-22 | 2017-06-29 | アサヒ飲料株式会社 | 容器詰めコーヒー飲料、コーヒー飲料の製造方法およびコーヒー飲料の呈味改善方法 |
JP6458192B1 (ja) * | 2018-07-09 | 2019-01-23 | 小川香料株式会社 | 練乳風味増強剤 |
JP6932226B1 (ja) * | 2020-07-29 | 2021-09-08 | キユーピー株式会社 | 食酢、飲食品、燻製香の付加方法、及び不快臭のマスキング方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3904780A (en) * | 1973-05-30 | 1975-09-09 | Suntory Ltd | Method for giving and increasing the flavor resembling to dairy product |
NL8104274A (nl) * | 1981-09-16 | 1983-04-18 | Naarden International Nv | Parfumcomposities en geparfumeerde produkten die alifatische ketonen als parfumgrondstof bevatten alsmede alifatisch keton geschikt voor gebruik als parfumgrondstof. |
-
1997
- 1997-07-22 DE DE69732435T patent/DE69732435T2/de not_active Expired - Fee Related
- 1997-07-22 JP JP10507346A patent/JP2000516645A/ja active Pending
- 1997-07-22 CN CNB97198185XA patent/CN1161034C/zh not_active Expired - Fee Related
- 1997-07-22 CN CNA2004100485140A patent/CN1575790A/zh active Pending
- 1997-07-22 AT AT97935535T patent/ATE288207T1/de not_active IP Right Cessation
- 1997-07-22 BR BR9711001-9A patent/BR9711001A/pt not_active Application Discontinuation
- 1997-07-22 EP EP97935535A patent/EP1006813B1/en not_active Expired - Lifetime
- 1997-07-22 WO PCT/EP1997/003964 patent/WO1998005220A1/en active IP Right Grant
- 1997-07-22 AU AU38493/97A patent/AU735054B2/en not_active Ceased
- 1997-07-22 CA CA002262462A patent/CA2262462C/en not_active Expired - Fee Related
- 1997-07-22 US US09/230,677 patent/US6296889B1/en not_active Expired - Fee Related
- 1997-07-22 ES ES97935535T patent/ES2237799T3/es not_active Expired - Lifetime
- 1997-07-22 NZ NZ333966A patent/NZ333966A/xx unknown
- 1997-08-01 AR ARP970103496A patent/AR008145A1/es unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102584653A (zh) * | 2011-12-15 | 2012-07-18 | 华宝食用香精香料(上海)有限公司 | 一种新型烤香香料的制作方法、其产品及用途 |
CN102584653B (zh) * | 2011-12-15 | 2014-05-28 | 华宝食用香精香料(上海)有限公司 | 一种新型烤香香料的制作方法、其产品及用途 |
Also Published As
Publication number | Publication date |
---|---|
CA2262462A1 (en) | 1998-02-12 |
EP1006813B1 (en) | 2005-02-02 |
EP1006813A1 (en) | 2000-06-14 |
ES2237799T3 (es) | 2005-08-01 |
CN1231581A (zh) | 1999-10-13 |
ATE288207T1 (de) | 2005-02-15 |
US6296889B1 (en) | 2001-10-02 |
CA2262462C (en) | 2009-01-13 |
CN1575790A (zh) | 2005-02-09 |
WO1998005220A1 (en) | 1998-02-12 |
AR008145A1 (es) | 1999-12-09 |
NZ333966A (en) | 2000-07-28 |
BR9711001A (pt) | 2000-01-11 |
JP2000516645A (ja) | 2000-12-12 |
AU3849397A (en) | 1998-02-25 |
DE69732435T2 (de) | 2006-01-05 |
AU735054B2 (en) | 2001-06-28 |
DE69732435D1 (de) | 2005-03-10 |
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