CN1274355A - 作为调味剂释放化合物的二烷氧羰基二氧戊环化合物 - Google Patents
作为调味剂释放化合物的二烷氧羰基二氧戊环化合物 Download PDFInfo
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- CN1274355A CN1274355A CN99801154A CN99801154A CN1274355A CN 1274355 A CN1274355 A CN 1274355A CN 99801154 A CN99801154 A CN 99801154A CN 99801154 A CN99801154 A CN 99801154A CN 1274355 A CN1274355 A CN 1274355A
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- butyl oxide
- carbonyl diurethane
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 235000019505 tobacco product Nutrition 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
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- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
式(Ⅰ)的二烷氧羰基二氧戊环在酸性含水酒精或非酒精饮料中是稳定的。因此它们可用于食品特别是饮料中通过长时间释放柠檬醛而稳定这些产品的柠檬醛特性。
Description
本发明涉及二烷氧羰基二氧戊环及含有这些化合物的柠檬醛释放制剂(citral release preparation)。
醛是一类重要的调味化合物(flavor compound)并且广泛存在。这类化合物在给消费品提供额外的风味或气味中也是非常有价值的。但是,醛如柠檬醛的高反应活性是导致成品稳定性问题的主要因素。醛的化学特性和其对亲核试剂的反应活性是以其末端的羰基为特征的。醛容易被还原为相应的醇,被氧化成羧酸或进行加成反应如羟醛缩合反应。由于共轭双键,不饱和醛具有很强的聚合倾向。这种聚合可以发生在较长的储存期间中。而且,不饱和醛也可以与硫发生1,4-加成反应导致众多的冲击性的调味化合物(impactflavor compounds)(K.-H.Engel,R.Tressl,J.Agric.Food Chem.1991,39,2249)。
作为一系列重要醛如脂肪族的C7-C12醛、柠檬醛和香茅醛很好来源的柑橘油(citrus oils)具有很广的应用范围。柠檬醛即香叶醛和橙花醛的混合物是柑橘油中的一种主要的冲击性成分,其可以从天然原材料如柠檬草中分离或合成得到,如从异戊二烯醇开始合成。除由于其和谐性(harmony)而成为首选的天然柠檬醛外,标准的合成柠檬醛通常用于低成本的大批量产品。合成柠檬醛是美国1985年总消耗约100吨和年产量几千吨的用作调味剂的重要合成成分[P.Z.Bedoukian,in Perfumery and Flavouring synthetics,AlluredPublishing,Wheaton(1986),16-18页]。
柠檬醛在配制柑橘型酒精和非酒精饮料的中也起着主要作用。这些柑橘型饮料(citrus beverage)通常具有范围在2至4的相对低的pH值。关于柠檬醛在这种酸性条件下如柠檬水饮料、柠檬油乳液等的稳定性已有很多研究(H.Friedrich,B.A.Gubler.Lebensm.-Wiss.u.Technol.1978,11,215-218;同前,1978,11,316-318)。研究显示柠檬醛会通过一系列环化和氧化反应而降解产生各种化合物如对繖花烃、对甲酚、香芹酮和对甲基苯乙酮,它们是柑橘型饮料中的产生异味的主要原因(K.Kimura,H.Nishimura,I.Iwata,J.Mizutani,J.Agric.Food Chem.1983,31,801-804;P.Schieberle,W.Grosch,Z.Lebensm.Unters.Forsch.1989,189,26;E.J.Freeburg,B.S.,G.A.Reineccius,J.Scire,Perfumer & Flavorist 1994,19,7月/8月,23-32.)。
根据目前的主要策略,通过与一种减慢或阻止产品在被热解、加热、咀嚼或润湿前释放醛的基质掺混,从而使醛在消费品中稳定。另外,可以将醛以共价键与辅助成分键合以形成低挥发性的高分子量分子。然后可以通过热解、加热或溶剂分解而释放醛。乙缩醛(acetal)可以用作共价结合醛调味剂的载体。例如US-A4,296,137公开了用醋酸1-乙氧基-1-乙醇酯作为很多消费材料的增香剂和增味剂。US-A-4,280,011公开了乙缩醛在食品中作为醛产生剂的应用。US-A-3,625,709公开了含有与碳水化合物结合的乙醛的食品调味和增香剂组合物。这些组合物当遇热或冷水时会释放乙醛。EP-Al-0501 645公开了在香烟组合物中用作风味-释放添加剂的酒石酸醛缩醇(tartrate acetals)或酮缩醇(ketals)制剂,当在抽烟条件下,其释放挥发性的醛或酮香味进入香烟中。US-A-5,144,048公开了作为释放有气味分子的前体的二烷氧羰基二氧戊环衍生物。它们可用于烟草制品、烹饪食品和口香糖中。
由于所有这些使不稳定的醛稳定的方法均是已知的,试验柠檬醛二甲基乙缩醛和柠檬醛丙二醇乙缩醛作为可能的柠檬醛前体似乎是显而易见的(A.Sharama,S.Nagarajan,K.N.Gurudutt,J.Agric.Food Chem.1998,46,654-656)。但是,这些化合物在含水溶液和酸性含水酒精和非酒精饮料中会迅速水解。由于它们的半衰期(halflife)短,这些化合物不能被考虑用于消费品中,柠檬醛在酸性含水酒精和非酒精饮料中的不稳定性仍然未解决。
本发明通过提供式I的二烷氧羰基二氧戊环衍生物解决了这个问题:其中R1和R2相同或不同并且代表H、直链或支链烷基、链烯基、环烷基、芳基、芳烷基。
令人惊奇地发现式I的二烷氧羰基二氧戊环,与柠檬醛二甲基乙缩醛(citral dimethyl acetal)和柠檬醛丙二醇乙缩醛(citral propylene glyco acetal)(A.Sharama,S.Nagarajan,K.N.Gurudutt,J.Agric.Food Chem.1998,46,654-656)相比,在酸性含水酒精和非酒精饮料中有较长的半衰期。与柠檬醛二甲基乙缩醛和柠檬醛丙二醇乙缩醛相比,式I的二烷氧羰基二氧戊环的半衰期在消费品中应用范围之内。令人惊奇地是式I的二烷氧羰基二氧戊环可以在较长时间内释放柠檬醛(香叶醛和橙花醛)。更令人惊奇的是释放速度可以通过改变酯基R1和R2来调节。小的R1和R2基团可以使其具有短的半衰期,而较大基团和长的烷基链可以使式I的二烷氧羰基二氧戊环具有长的半衰期。因此,可以设计具有不同释放特性(release profile)的柠檬醛释放制剂。这特别适用于具有不同保质期的酸性含水酒精或非酒精饮料。例如具有短半衰期的柠檬醛释放制剂适宜作即饮饮料,而具有长半衰期的柠檬醛释放制剂更适宜作有一定保质期的消费饮料。
式I化合物没有任何具体的异构体限制并且所有异构体都包括在本发明范围内。
式I化合物可用于消费品中,如食品,特别是含水的,酒精或非酒精柑橘型饮料中。它们通过在长时间内释放柠檬醛而使这些产品的柠檬醛特征稳定。该释放制剂特别适用于由饮料粉与水混合而制备的即饮饮料。
柠檬醛释放制剂可以含有单个的式I的二烷氧羰基二氧戊环衍生物或几个式I的二氧戊环衍生物的混合物。本发明的制剂也可以包括(附加的)调味剂(flavor)。干制剂是稳定的。在与水接触后调味剂迅速从制剂中释放,而通式I化合物缓慢释放柠檬醛。由于其长期持续的柠檬醛味,因此所得饮料优于没有柠檬醛释放制剂的饮料。
本发明的柠檬醛释放制剂可用于在长时间内能够提供特有的柠檬醛气味的消费品中。柠檬醛释放制剂可以与柠檬醛联合使用,它们可以部分地替代通常出现在柠檬/酸柠檬或其它调味料中的柠檬醛并且它们可以完全替代调味料中的柠檬醛。优选释放制剂与柠檬醛联合使用。
本发明的释放制剂可以是粉末并可用本领域已知的方法制备。粉末形式的释放制剂可以通过将含有一种或多种通式I衍生物的乳液喷雾干燥而制备。通式I化合物可以就这样或溶解在亲脂性食品级溶剂中加入要干燥的乳液中。优选使用种植物油(plant oil),如植物油(vegetable oil)。具有乳化特性的乳化剂和载体材料可用于制备乳液。用于乳液的载体材料选自常用于该目的的材料。优选的载体材料是碳水化合物、改性淀粉、降解淀粉(糊精、麦芽糖糊精)、天然树脂、渗出物,例如阿拉伯树胶、植物提取物,如角叉藻聚糖(carragenan)、藻酸盐等等,蛋白质,如牛奶蛋白或明胶,以及上述或其它常用载体材料的组合。对于用于这些乳液的溶剂,能够使用例如水或水/乙醇混合物。常用添加剂,如人造甜味剂、食品着色剂、维生素、抗氧化剂、止泡剂、味道改性剂,如柠檬酸也可以加入乳液中。与式I的二烷氧羰基二氧戊环衍生物一起,可向乳液中加入调味组合物以提供含有调味香料的释放制剂。然后将该乳液喷雾干燥得到通常为粉末形式的含有1%-30%,优选5%-20%式I的二烷氧羰基二氧戊环衍生物的释放制剂。
颗粒形式的柠檬醛释放制剂可以按WO-Al-9716078所述的方法制备。由此将流体化的芯材料雾化并与含有一种或多种式I的二烷氧羰基二氧戊环的乳液制粒。将具有直径为0.02-3.0mm,优选0.2-1.5mm的食品或药品级固体材料用作芯材料。优选的芯材料是碳水化合物,例如糖如蔗二糖(sucrose)、葡萄糖、蔗糖(saccharose)或具有复杂组成的材料,例如果汁粉、水解植物蛋白(HVP)、无机盐如氯化钠或柠檬酸盐。被雾化的乳液含有载体材料如碳水化合物,例如改性淀粉、降解淀粉(糊精、麦芽糖糊精)、天然树脂、渗出物如阿拉伯树胶、植物提取物,如角叉藻聚糖、藻酸盐等等,蛋白质,如牛奶蛋白或明胶,或这些材料的组合。水或水/乙醇混合物能够用作这些乳液的溶剂。乳液中也可以含有常用添加剂,如人造甜味剂、食品着色剂、维生素、抗氧化剂、止泡剂、味道改性剂,如柠檬酸。
所得颗粒可以另外包衣,如喷上常用于这些目的的材料,如脂肪、改性纤维素、明胶或植物提取物的溶液或乳液。
此外,式I的二烷氧羰基二氧戊环还可以单独包封或与其它香味成分一起包封。因此,可以得到含有一种或多种式I化合物和调味剂的包封的释放制剂(encapsulated release preparation)。本发明的包封的释放制剂通常含有1%至30%式I的二烷氧羰基二氧戊环衍生物,优选5%至20%。
柠檬醛释放制剂的用量应该足以给食品提供柠檬醛典型的新鲜的、类-柠檬特征,并且用量取决于成品所需要的精确的传入感觉器官的特征。当柠檬醛释放制剂是给未调味的材料提供全面的柠檬/酸柠檬风味时需要量大,并且当增强已经调过味的材料的柠檬醛特征为目的时需要量较少。
式I的二烷氧羰基二氧戊环衍生物可以用本领域已知的方法容易地制备(T.W.Greene,P.G.M.Wuts,”Protective Group in Organic Synthesis”2nd Ed,John Wiley & Sons,Inc.,New York 1991.)。制备这类化合物的常规方法包括使柠檬醛二甲基乙缩醛与酒石酸低级烷基酯在惰性有机溶剂中在酸催化剂存在下缩合。在缩合反应中甲醇被共沸地除去。催化量或等摩尔量的质子或路易斯酸可用于缩合反应中。可使用的酸是对甲苯磺酸、硫酸、磷酸、盐酸、甲磺酸、对甲基磺酸吡啶鎓、三氯化铁、酸性离子交换树脂、氯化锌、四氯化钛。优选的酸包括对甲苯磺酸和甲磺酸。最优选的酸是对甲基吡啶鎓。
为了除去甲醇,可以使用多种溶剂如甲苯、苯、环己烷、二甲苯、己烷、氯苯、二甲基甲酰胺和甲基叔丁醚。优选的溶剂是环己烷和二甲基甲酰胺。最优选的溶剂是甲基叔丁醚。
反应中形成的甲醇可以通过共沸蒸馏或通过分子筛净化除去。
根据这些方法可以得到稳定的粘性油状的本发明二烷氧羰基二氧戊环衍生物。将粗品在高真空下干燥并在高温下除去未反应的起始原料可得到高纯度的式I化合物(>90%)。它们可以直接使用或可以通过闪式色谱进一步纯化。
本发明的柠檬醛释放制剂以使成品产生可感知量柠檬醛的有效的用量单独使用。但是,更一般地,式I化合物可以与足以使食品产生所需风味的量与调味化合物混合使用。达到产品所需的全部作用的用量根据释放制剂的具体形式、在其中使用的食品和所需的具体作用而变化。
下列实施例用于说明本发明但不限制本发明。
实施例1
(E/Z)-(4R,5R)-2-(2,6-二甲基-庚-1,5-二烯基)-[1,3]二氧戊 环-4,5-二羧酸二异丙酯(1):
将20.0g(85.5mmol)(R,R)酒石酸二异丙酯、33.85g(170.9mmol)柠檬醛二甲缩醛(citral dimethyl acetl)和0.5g对甲苯磺酸吡啶 的350mlMTBE溶液在回流温度(55℃)加热5小时。将澄清的黄色反应混合物冷却至室温再加入150ml饱和NaHCO3溶液。分离水层并用150mlMTBE洗涤两次。将合并的有机层用100ml盐水洗涤,干燥(MgSO4)并真空浓缩(旋转蒸发)。用Buchi-Kugelrohrofen仪将油状残余物(47.1g)在高真空度(0.1torr)和110℃的温度下干燥得到25.5g(81%)柠檬醛酒石酸二异丙酯(citral diisopropyl tartrate)1。
1H-NMR:1.30(d,CH3),1.31(d,CH3),1.61(s,CH3),1.68(s,CH3),1.79(d,CH3),2.0-2.2(m,4H,CH2),4.61(m,1H),4.67(m,1H),5.0-5.2(m,3H),5.36(m,1H),5.91(dd,1H);MS:368(3,M′),281(5),245(8),69(100),41(83).
实施例2
(E/Z)-(4R,5R)-2-(2,6-二甲基-庚-1,5-二烯基)-[1,3]二氧 戊环-4,5-二羧酸二丁酯(2):
按照实施例1中所述的酒石酸二异丙酯的制备方法,得到收率为78%的柠檬醛酒石酸二丁酯2。1H-NMR:0.95(m,2 CH3),1.41(m,4H,CH2),1.55-1.75(m,4H,CH2),1.60(s,CH3),1.68(s,CH3),1.80(s,CH3),2.0-2.2(m,4H,CH2),4.22(m,4H,OCH2),4.68(m,1H),4.76(m,1H),5.1(m,1H),5.46(m,1H),5.91(dd,1H);MS:396(3,M+),339(7),273(11),83(32),69(93),57(38),41(100).
实施例3
(E/Z)-(4R,5R)-2-(2,6-二甲基-庚-1,5-二烯基)-[1,3]二氧
戊环-4,5-二羧酸二乙酯(3):
按照实施例1中所述的柠檬醛酒石酸二异丙酯的制备方法,得到收率为80%的柠檬醛酒石酸二乙酯3。1H-NMR:1.32(m,2 CH3),1.61(s,CH3),1.67(s,CH3),1.80(d,CH3),2.0-2.2(m,4H,CH2),4.28(m,4H,OCH2),4.68(m,1H),4.76(m,1H),5.1(m,1H),5.36(m,1H),5.91(dd,1H);MS:340(3,M+),267(5),217(22),69(100),41(80).
实施例4
(E/Z)-(4R,5R)-2-(2,6-二甲基-庚-1,5-二烯基)-[1,3]二氧
戊环-4,5-二羧酸二甲酯(4):
按照实施例1中所述的柠檬醛酒石酸二异丙酯的制备方法,得到收率为56%的柠檬醛酒石酸二甲酯4。1H-NMR:1.61(s,CH3),1.70(s,CH3),1.80(t,CH3),),2.0-2.2(m,4H,CH2),3.85(t,CH3),4.72(m,1H),4.81(m,1H),5.1(m,1H),5.30(m,1H),5.90(dd,1H);MS:312(2,M+),189(17),69(100),41(97).
实施例5
(E/Z)-(4R,5R)-2-(2,6-二基-庚-1,5-二烯基)-[1,3]二氧
戊环-4,5-二羧酸二丙酯(5):
按照实施例1中所述的柠檬醛酒石酸二异丙酯的制备方法,得到收率为74%的柠檬醛酒石酸二丙酯5。1H-NMR:0.96(t,CH3),1.60(s,CH3),1.70(s,CH3),1.80(d,CH3),1.60-1.80(m,4H,CH2),2.0-2.2(m,4H,CH2),4.20(t,4H,OCH2),4.70(m,1H),4.77(m,1H),5.10(m,1H),5.37(m,1H),5.90(dd,1H);MS:368(l,M+),281(3),245(13),69(100),41(82).
实施例6
化合物1的稳定性:
实施例1中化合物1的稳定性试验在通过1+5方式将柠檬/酸柠檬-柠檬饮料浓缩物(210g)用水(835g)稀释后得到的不起泡的柠檬饮料(still lemonbeverage)中进行。柠檬/酸柠檬-柠檬饮料浓缩物的配方是:
表1
成分 用量
糖浆65Bx 1033g
苯甲酸钠 1g
柠檬酸钠 2g
柠檬酸,在水中50%w/w 50g
水 193g
制备三份100ml各含100ppm化合物1的溶液并且化合物1在5天内的分解通过用加有100ppm肉豆蔻酸乙酯的己烷萃取5ml试验溶液样品而确定。萃取液通过GC(Hewlett Packard 6890;柱:DB-5,30m,0.32mm i.d)分析并在三个测定的基础上计算每个数据点的平均值。假设衰退遵循一次动力学(first order kinetic),
计算化合物1的半衰期t1/2=4天。
实施例7
化合物5的稳定性:
实施例5中化合物5的稳定性按照实施例6所述的化合物1稳定性的测定方法进行并且计算的半衰期为11天。
实施例8
化合物3的稳定性:
实施例3中化合物3的稳定性按照实施例6所述的化合物1稳定性的测定方法进行并且计算的半衰期为21小时。
实施例9
含有化合物3的柠檬醛释放制剂A)的制备。
将按照表2制备的乳液按照WO-Al 9716078的方法喷雾干燥得到含有1%柠檬醛酒石酸二乙酯3的粉末。
表2
成分 份数 固体干重
化合物(3),5%在植物油中 90.90 20
丙二酸藻酸酯类(Kelcoloids) 1.6 0.35
改性淀粉(Capsul) 68.2 15
麦芽糖糊精 293.8 64.65
水 545.50 00
实施例10
将表3中的成分在2夸脱水中混合并将其储存在冰箱中直至试验。将一组专业为饮料的食品技术人员制备的样品进行24小时或72小时试验。
表3
成分 对照 样品1
糖 175.0g 175.0g
柠檬酸 4.0g 4.0g
人造柠檬调味剂#1835551) 1.06g 1.06g
释放制剂A) 0g 0.53g
1)Givaudan Rour Flavors有限公司售出为柠檬香料的香料。
专家小组成员判定样品1在24小时后略优于对照的柠檬饮料并在48小时和72小时后大大优于对照品。
实施例11
将表4中的成分在2夸脱水中混合并将其储存在冰箱中直至试验。将样品让通过经过训练来评定柠檬的不同属性的专家小组评估。
表4
成分 对照 样品1 样品2
糖 175.0g 175.0g 175.0g
柠檬酸 4.0g 4.0g 4.0g
人造柠檬调味剂#1835551) 1.06g 1.06g 1.06g
释放制剂A) 0g 0.53g 1.06g
1)Givaudan Rour Flavors有限公司售出为柠檬香料的香料。
专家小组发现使用释放制剂A)可以增强柠檬的某些所期望的属性,特别是当以样品1的水平使用时。
样品1,24小时后:与对照相比显示增强的甜味。
样品1,72小时后:显示强烈的糖果(candy)、柠檬果皮味(lemon peelynotes)(柠檬香料的两个重要的正性属性)。
样品2,24小时后:与对照相比显示增强的甜味。
样品2,72小时后:与对照相比显示较强的香茅醛味(柠檬的特性)。
在样品2水平,也观察到某些负面属性如苦味和涩味的增强。
Claims (13)
2.根据权利要求1的二烷氧羰基二氧戊环,其中R1和/或R2是C1-C10烷基。
3.根据上述任一权利要求的二烷氧羰基二氧戊环,其中R1和/或R2是乙基。
4.含有根据上述任一权利要求的二烷氧羰基二氧戊环和固体载体的柠檬醛释放制剂。
5.含有根据权利要求1至3任一项的二烷氧羰基二氧戊环的混合物的柠檬醛释放制剂。
6.根据权利要求4或5的柠檬醛释放制剂,含有固体载体。
7.根据权利要求4或5的柠檬醛释放制剂,含有包封剂。
8.物根据权利要求4至7任一项的柠檬醛释放制剂,含有调味化合物。
9.根据权利要求4至8任一项的柠檬醛释放制剂,其中固体载体材料是麦芽糖糊精。
10.根据权利要求4至9任一项的柠檬醛释放制剂,其中固体载体材料是改性淀粉。
11.根据权利要求4至10任一项的柠檬醛释放制剂,其中固体载体材料是阿拉伯胶。
12.制备根据权利要求5至11任一项的柠檬醛释放制剂的方法,包括通过将式I的二烷氧羰基二氧戊环乳液喷到流化的芯材料上并将式I的二烷氧羰基二氧戊环制粒。
13.根据权利要求4至11任一项的柠檬醛释放制剂在柑橘型饮料中延长其柠檬醛特征的应用。
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US (1) | US6387431B1 (zh) |
EP (1) | EP1023280A1 (zh) |
JP (1) | JP2002520405A (zh) |
CN (1) | CN1274355A (zh) |
BR (1) | BR9906621A (zh) |
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JP4689106B2 (ja) * | 2000-10-13 | 2011-05-25 | 花王株式会社 | シトラールアセタール |
US6506793B2 (en) * | 2000-10-13 | 2003-01-14 | Kao Corporation | Citral acetal |
DE10140786A1 (de) * | 2001-08-20 | 2003-03-06 | Haarmann & Reimer Gmbh | Depotpräparate |
DE10140787A1 (de) * | 2001-08-20 | 2003-03-06 | Haarmann & Reimer Gmbh | Depotpräparate |
EP1487815A1 (en) * | 2002-03-28 | 2004-12-22 | Firmenich Sa | Compounds for the controlled release of active aldehydes |
DE10333379A1 (de) | 2003-07-23 | 2005-02-10 | Symrise Gmbh & Co. Kg | Acetale, ihre Verwendung als Reichstoffe und Verfahren zu ihrer Herstellung |
US20080300314A1 (en) * | 2003-11-21 | 2008-12-04 | Givaudan Sa | Cooling Compounds |
BRPI0607270B1 (pt) * | 2005-01-25 | 2015-12-29 | Givaudan Sa | método de encapsulação para compostos |
WO2006119660A1 (en) * | 2005-05-11 | 2006-11-16 | Givaudan Sa | Encapsulation method |
EP1917074B1 (en) | 2005-08-15 | 2018-02-28 | Givaudan SA | Cooling compounds |
WO2007022651A1 (en) * | 2005-08-22 | 2007-03-01 | Givaudan Sa | Substituted bicyclo [2.2.2] oct/5-ene compounds and their use as cooling agents |
DE602006009290D1 (de) * | 2005-10-25 | 2009-10-29 | Givaudan Sa | Organische verbindungen |
BRPI0709393A2 (pt) * | 2006-03-15 | 2011-07-05 | Givaudan Sa | compostos 2-alcoxifenóis para -substituìdos, uso dos mesmos, método de fornecer um efeito refrescante à boca ou pele e produto contendo ditos compostos |
WO2008134908A1 (en) * | 2007-05-08 | 2008-11-13 | Givaudan Sa | Wax encapsulation |
ATE540667T1 (de) | 2007-06-13 | 2012-01-15 | Givaudan Sa | Verbindungen mit kühlender wirkung |
US7880011B2 (en) * | 2007-07-23 | 2011-02-01 | Givandan, S.A. | Amide addition reaction |
US20100297038A1 (en) * | 2008-01-17 | 2010-11-25 | Givaudan S.A. | Benzimidazole Derivatives And Their Use As Cooling Agents |
US8939388B1 (en) | 2010-09-27 | 2015-01-27 | ZoomEssence, Inc. | Methods and apparatus for low heat spray drying |
US9332776B1 (en) | 2010-09-27 | 2016-05-10 | ZoomEssence, Inc. | Methods and apparatus for low heat spray drying |
SI2680712T1 (sl) * | 2011-03-04 | 2019-08-30 | International Flavors & Fragrances Inc. | Postopek izdelave s pršenjem sušenih spojin, zmožnih zadrževanja hlapnih spojin |
MX2017008973A (es) | 2015-01-21 | 2017-11-09 | Firmenich & Cie | Compuestos de acetal y cetal fotolabiles para la liberacion controlada de compuestos de carbonilo volatiles activos. |
US10155234B1 (en) | 2017-08-04 | 2018-12-18 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
US9993787B1 (en) | 2017-08-04 | 2018-06-12 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
WO2019028446A1 (en) | 2017-08-04 | 2019-02-07 | ZoomEssence, Inc. | APPARATUS AND METHOD FOR HIGH-PERFORMANCE SPRAY DRYING |
US9861945B1 (en) | 2017-08-04 | 2018-01-09 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
US10486173B2 (en) | 2017-08-04 | 2019-11-26 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
US10569244B2 (en) | 2018-04-28 | 2020-02-25 | ZoomEssence, Inc. | Low temperature spray drying of carrier-free compositions |
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1999
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