CN101139304A - 烯酰胺及其用途 - Google Patents
烯酰胺及其用途 Download PDFInfo
- Publication number
- CN101139304A CN101139304A CNA200710147271XA CN200710147271A CN101139304A CN 101139304 A CN101139304 A CN 101139304A CN A200710147271X A CNA200710147271X A CN A200710147271XA CN 200710147271 A CN200710147271 A CN 200710147271A CN 101139304 A CN101139304 A CN 101139304A
- Authority
- CN
- China
- Prior art keywords
- acid amides
- cyclopropyl
- hexadiene
- consumable material
- hexadiene acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
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Abstract
本发明提供新颖的化合物,它选自:N-乙基E2,E4-己二烯酰胺;N-环丙基E2,E4-己二烯酰胺;N-环丙基Z4-庚烯酰胺;和N-环丙基Z3-己烯酰胺。本发明还涉及这些化合物的用途:增加、增强或赋予消耗材料和/或口腔和/或人体表皮香味、味道、物质感觉作用和/或抗菌作用。
Description
本申请是申请人于2004年10月8日提交的、申请号为“200410083517.8”、发明名称为“共轭二烯酰胺及其制备方法,含共轭二烯酰胺的组合物及其用途”的发明专利申请的分案申请。
技术领域
C10-C11-E2,E4-链二烯酰胺混合物,可合成得到或从干的磨碎的胡椒植物、荜茇(Piper longum Linn)或菩提胡椒(Piper peepuloides)得到,在口腔中和皮肤上散发有益的香味和感觉。
背景技术
众所周知,C10和C12二烯及三烯酰胺衍生物在许多植物性药材中存在,并且,当用在食品、口香糖、口腔护理产品、头发护理产品、科龙香水,局部化装品或药物中时,它们的使用会在口腔和皮肤上产生香味和/或麻刺和/或温热的感觉。还揭示这些C10和C12二烯及三烯酰胺衍生物呈现生物活性,最显著的是抗细菌、抗真菌和杀虫活性。“C10和C12二烯及三烯酰胺衍生物”类成员的最重要化合物揭示如下:
千日菊酰胺的结构:
Nakanatsu等人在欧洲专利申请EP1121927A2中揭示它在口腔护理,皮肤护理和药物产品中的应用。
墙草碱,N-异丁基-2,4-癸二烯酰胺的结构:
Lyeremide A(N-吡咯烷基-2,4-癸二烯酰胺)的结构:
Lyeremide B(N-哌啶基-2,4-癸二烯酰胺)的结构:
Adesina等人在“GC/MS Investigations of the minor constituents ofPiper guineens stem”,Pharmizie 57(2002)9,622-627页中揭示:胡椒碱(N-哌啶基-5(3,4-亚甲二氧基苯基)-2,4-戊二烯酰胺)和N-异丁基-2,4-十二碳二烯酰胺作为Piper guineense stem的组分。在Adesina的文章的引言中表明:“Piper guineens Schum and Thonn,(胡椒科(Piperaceae)...叶子和果实...已用作调味品、食用香料,一般作为食品中的香料。果实的浓烈胡椒味赋予可其接受性,并使用在一些食物和药物制剂中。
在美国专利6365601中揭示胡椒碱,N-哌啶基-5(3,4-亚甲二氧基苯基)-2,4-戊二烯酰胺,可从胡椒属果实提取,包括荜茇,这里它以4.5%的浓度存在。Das等人在Natural Prodict Sciences,4(1):23-25(1998)的“One Newand Two Rare Alkamides from Two Samples of the Piper longgum”(“从荜茇的二个样品中得到的一个新的和稀有的烷酰胺”)揭示:相应的2,4-庚二烯酰胺也可从荜茇果实提取。
但是,以前的工艺没有揭示4个或更多个C10-C11-E2,E4-链二烯酰胺的混合物,尤其是以高的浓度,例如,在3%和100%之间,该混合物对口腔中和皮肤上的有益香味和感觉是有用的。而且,以前的工艺也没有揭示这些C10-C11-E2,E4-链二烯酰胺混合物可从胡椒植物,荜茇或菩提胡椒的干果实提取。
发明内容
本发明涉及至少4个C10-C11-E2,E4-链二烯酰胺的混合物,每个链二烯根据下列结构定义:
其中,R表示C1-C2正烷基;R1是2-甲基-1-丙基,R2是氢,或者,R1和R2结合在一起是形成具有分子式-(CH2)n-的部分,这里n是4或5。
在本发明的另一实施例中,发现下列新颖化合物及其混合物,以及它们增加、增强或赋予消料耗材和/或口腔和/或人体表皮以香味、味道、物质感觉(chemesthetic)作用和/或抗菌作用的用途。
N-乙基E2,E4-己二烯酰胺
N-环丙基E2,E4-己二烯酰胺
N-环丙基Z4-庚二烯酰胺
N-环丙基Z4-癸烯酰胺
N-环丙基Z3-己烯酰胺
在本发明的另一实施例中,提供上述新颖化合物以及下列化合物的使用,通过使用有效量下列化合物及其混合物,增加、增强或赋予消耗材料对口腔和/或人体表皮的香味、味道、物质感觉作用和/或抗菌作用:
N-甲基E2,E4-己二烯酰胺
N-烯丙基E2,E4-己二烯酰胺
N,N-二甲基E2,E4-己二烯酰胺
本发明的混合物对增加、增强或赋予消耗材料对口腔和/或人体表皮的芳香,芳香、味道、物质感觉作用和/或抗菌作用,是有用的。这里的术语“物质感觉作用”意指口腔中的感觉,刺激,发热和唾液分泌,包括嘴唇和在人体表皮上的刺激和发热。因此,本发明的混合物在这些材料(比如香水组合物,芳香制品)中是有用的,包括化妆品,肥皂,清洁剂和精致的芳香组合物,食品,口香糖,非酒精饮料,酒精饮料,口腔护理产品,如洗口水,牙膏,咳嗽滴液,咳嗽糖浆和咽喉止咳糖;皮肤护理产品,包括润肤膏和洗液;头发护理产品,包括去屑组合物和香波。
本发明的混合物此后称为“C10-C11-E2,E4-链二烯酰胺混合物”。
本发明的C10-C11-E2,E4-链二烯酰胺的混合物,可以下列方法得到1)胡椒植物、荜茇或之一的提取,2)形成天然产物的合成,或3)形成合成产品的合成。因此发明还针对C10-C11-E2,E4-链二烯酰胺混合物形成的方法。
此外,发明涉及增加、增强或赋予消耗材料和/或口腔和/或人体表皮香味、味道、物质感觉作用和/或抗菌作用方法,其步骤是将所述消耗材料与有效浓度和数量的一个或多个有香味、味道、物质感觉作用和/或抗菌作用的C10-C11-E2,E4-链二烯酰胺混合物相混合和/或把这种混合物引入到口腔和/或涂到人体表皮上。
附图说明
图1是显示过程的示意块流程图,其中本发明的C10-C11-E2,E4-链二烯酰胺混合物通过胡椒植物,荜茇或菩提胡椒之一的提取方法得到。
图2是本方法制备的提取物的GC-质谱部分,其中本发明的C10-C11-E2,E4-链二烯酰胺混合物通过胡椒植物、荜茇的提取方式得到。
图3是本方法制备的提取物的GC-质谱部分,其中本发明的C10-C11-E2,E4-链二烯酰胺混合物,通过提取胡椒植物菩提胡椒的方式得到。
图4是一组比较条形图,显示:(i)含各种浓度的C10-C11-E2,E4-链二烯酰胺混合物的荜茇和菩提胡椒的提取物;(ii)墙草碱;(iii)其他感知物质,图中表示(a)按1-9级给喜欢程度分等;(b)按1-9级给强度分等;(c)持续时间(单位:分钟);。
图5是一组表明持续时间的条形图(单位:分钟),(i)含各种浓度本发明C10-C11-E2,E4-链二烯酰胺混合物的荜茇和菩提胡椒的提取物,(ii)墙草碱,(iii)其他感知物质。
具体实施方式
在本发明实践中,优选应用本发明C10-C11-E2,E4-链二烯酰胺混合物的浓度大约为3%-100重量%的混合物产物。另外,本发明的C10-C11-E2,E4-链二烯酰胺混合物优选包括下列组分:
A.N-异丁基-E2,E4-癸二烯酰胺;
B.N-异丁基-E2,E4-十一碳二烯酰胺;
C.N-吡咯烷基-E2,E4-癸二烯酰胺;
D.N-哌啶基-E2,E4-癸二烯酰胺。
结构:
当本发明的C10-C11-E2,E4-链二烯酰胺混合物通过胡椒植物、荜茇或菩提胡椒之一的提取得到时,所用的方法包括以下步骤:
i.研磨至少一种胡椒植物的干果实,它们选自荜茇和菩提胡椒,以便形成荜茇或菩提胡椒的平均粒度范围约300微米-800微米的粉末;
ii.提供装备多孔提取板的提取器,优选装备筛子的篮渗滤器;
iii.将一部分研磨的荜茇或菩提胡椒粉末放到每个所述多孔提取板上;
iv.用第一循环量的所给极性或非极性溶剂,如正己烷,在约30-50℃的温度范围,紧密接触这样支承着的研磨的荜茇或菩提胡椒粉末约10小时-20小时,溶剂与固体重量的比在约2.75∶1至3.25∶1,这样形成第一份提取液和初次提取了的研磨荜茇粉末;
v.从抽出器取出所述的第一份提取液;
vi.用第二循环量的所给极性或非极性溶剂,例如正己烷,在约30-50℃的温度范围,接触初次提取了的研磨荜茇或菩提胡椒粉末约10小时-20小时,溶剂与固体重量的比在约1.75∶1至2.25∶1,这样形成第二份提取液和两次提取了的研磨荜茇或菩提胡椒粉末;
vii.从抽出器取出所述的第二份提取液;
viii.用第三循环量的所给极性或非极性溶剂,例如正己烷,在约30-50℃的温度范围,接触两次提取了的研磨荜茇或菩提胡椒粉末约10小时-20小时,溶剂与固体重量的比在约0.75∶1至1.25∶1,这样形成第三份提取液和三次提取了的研磨荜茇或菩提胡椒粉末;
ix.从抽出器取出所述的第三份提取液;
x.合并所述的第一份,第二份和第三份提取液,形成合并的提取液;
xi.对形成的合并提取液进行蒸发单元操作,形成浓缩的提取液;
xii.在蒸汽温度约55-76℃范围,液体温度约109-203℃的范围和压力约30-60毫米汞柱的范围,任选分馏所形成的浓缩提取液,形成馏出液。
上述过程的优选变化如下:
(a)对作为进行第xi步的结果形成的浓缩提取液,用95%含水乙醇提取,对形成的乙醇提取液进行蒸发单元操作,形成浓缩的提取液;
(b)循环提取溶剂是95%含水乙醇,不进行任选分馏步骤,xii,;
(c)循环提取溶剂是95%含水乙醇,紧接着在进行蒸发单元操作(步骤xi)后,浓缩的提取液用正己烷提取,形成第四份提取液;对第四份正己烷提取液进行蒸发单元操作,形成浓缩提取液,在蒸汽温度约55-76℃,液体温度约109-203℃,压力约30-60毫米汞柱,分馏这些浓缩的提取液,形成馏出液。
另外,在不使用蒸馏步骤时,上面提到的过程还可包括另外的混合形成的提取液或馏出液与食品级稀释剂的步骤。
当本发明的C10-C11-E2,E4-链二烯酰胺的混合物组分,以天然产物形成的合成方式得到时,应用的方法包括以下步骤:
i.形成天然胺,选自异丁基胺,哌啶和吡咯烷;
ii.形成它的天然胺酸盐;
iii.任选中和形成的胺盐,形成相应的胺;
iv.提供天然E2,E4-二烯醛,选自E2,E4-癸二烯醛和E2,E4-十一碳二烯醛;
v.空气氧化或微生物氧化形成的E2,E4-二烯醛,从而形成相应的E2,E4-二烯酸;
vi.用天然链烷醇或天然的甘油,酯化形成的E2,E4-二烯酸,形成相应的E2,E4-二烯酸酯;
vii.在酯形成酶(如脂肪酶)的存在下,将形成的E2,E4-二烯酸酯与步骤ii中形成的天然胺盐反应,或与步骤iii中形成的天然胺反应;
viii.回收形成的酰胺。
然后将形成的各个酰胺相互混合,形成本发明的C10-C11-E2,E4-链二烯酰胺的混合物。
在上面所述方法中,在最初形成的胺是异丁基胺时,优选通过天然缬氨酸与天然芳香族酮或芳香族醛反应,形成亚胺羧酸;使形成的亚胺羧酸异构化和脱羧,形成脱羧亚胺;在pH约1.5-3.5,水解形成的脱羧亚胺,形成天然异丁基胺盐。
上面的E2,E4-二烯酸,在步骤vi中的酯化,优选用天然乙醇进行。
因此,例如,根据上面所述的普用方法,制备具有下列结构的天然N-异丁基E2,E4-癸二烯酰胺的具体方法,包括以下步骤:
i.形成天然异丁基胺酸盐,通过(a)天然缬氨酸与天然茴香醛反应形成亚胺;(b)异构化亚胺和进行脱羧,形成脱羧亚胺;(c)脱羧亚胺进行酸水解,形成异丁基胺的酸盐;(d)任选中和异丁基胺的酸盐,形成异丁基胺;
ii.形成天然2E,4E-癸二烯酸乙酯,通过(a)天然2Z,4E-癸二烯酸乙酯的热异构化;(b)在与乙醇的混合物中,天然2E,4E-癸二烯醛的空气氧化;或(c)天然2E,4E-癸二烯醛的微生物氧化;
iii.将形成的2E,4E-癸二烯酸乙酯与天然异丁基胺或它的盐,在酯化酶的存在下反应,癸二烯酸酯∶胺或盐的摩尔比从1∶1到3∶1,温度约30-80℃,时间约20-100小时,根据以下反应式:
iv.回收形成的天然N-异丁基-E2,E4-癸二烯酰胺。
在本发明的C10-C11-E2,E4-链二烯酰胺混合物组分,通过合成的产品形成合成方法得到时,使用的方法包括将E2,E4-二烯酸,选自E2,E4-癸二烯酸和E2,E4-十一碳二烯酸,溶解在兼容的溶剂中,形成E2,E4-二烯酸溶液;使形成的E2,E4-二烯酸溶液与约1-2当量的酸活化剂,选自:卤代甲酸低级烷酯,N,N-二脂族的或环脂族的偶氮二碳二亚胺,二卤代草酸酯,在约0-20℃混合,形成中间体;把形成的含中间体的溶液冷却到约-10℃至+10℃;当使用卤代甲酸低级烷酯或二卤代草酸酯反应时,在+10℃以下使其与三低级烷胺混合;然后,在室温条件下陈化形成的含中间体的产物约0.5-3小时,根据以下反应式:
过滤形成的产物;分离形成的滤液,并冷却形成滤液至-5到+5℃;在室温条件下,把形成的冷却滤液与约1-4当量的胺混合,选自:异丁基胺,哌啶和吡咯烷,进行酰胺化反应,形成根据下列结构定义的酰胺:
回收形成的酰胺。
然后把形成的各个酰胺相互混合,形成本发明的C10-C11-E2,E4-链二烯酰胺组分的混合物。
在使用酸活化剂氯甲酸乙酯时,反应进行如下:
这样形成的本发明的C10-C11-E2,E4-链二烯酰胺组分的混合物可分别与足够量和浓度的麻刺感觉剂混合,例如,一种或多种感觉剂选自具有如下结构的基本上纯的千日菊酰胺:
Acmella ciliata,Acmella(Spilanthes)Oppositifolia,南欧派利吞草(Anacyclus PyrethrumD.C.),天文草(Spilanthesacmella L.var oleraceae(Jambu))和赛菊芋(Heliopsis longipes S.F.Blake(Chilcuan)),形成的混合物然后用于增加、增强或赋予消耗材料和/或口腔和/或人体表皮香味、味道、物质感觉作用和/或抗菌作用方法,其步骤是将所述消耗材料与有效浓度和数量的有香味、味道、物质感觉作用和/或抗菌作用的形成混合物相混合和/或把这种混合物引入到口腔和/或涂到人体表皮上。
下表I阐明利用本发明的C10-C11-E2,E4-链二烯酰胺组分混合物的方法和组合物的例子。在引用的美国专利中提出每个有用成分和专利申请参考,包括它们的实施例,在本发明的实践中是可用的,结合在此供参考。
表I
本发明的C10-C11-E2,E4-链二烯酰胺组分的混合物的使用性质 | 包括可用于本发明的C10-C11-E2,E4-链二烯酰胺组分的混合物例子的参考 |
皮肤护理 | 美国专利6,096324 |
皮肤护理湿润剂和清洁剂 | 美国专利6,099,849 |
化妆品组合物 | 美国专利6,190,679 |
口感觉剂,增香剂和增效剂 | 美国专利申请2002/0122778A12002年9月5日公布 |
食品和口腔卫生的香味组合物 | 美国专利申请2002/0152682A12003年8月14日公布 |
阿魏酸酰胺用作香料化合物 | 欧洲公开申请EP1,121,927A22001年8月8日公布 |
食品,药品和个人护理产品 | 美国专利申请2002/0152682A12003年8月14日公布 |
去头屑和止痒组合物 | 美国专利申请系列号10/067,5962002年2月5日归档 |
滋味和感觉作用组合物 | 美国专利申请系列号10/411,6722003年4月11日归档 |
如这里使用的嗅觉有效量,理解为:在香料组合物,口腔护理组合物,鼻护理组合物,皮肤护理组合物,头发和头皮护理组合物,化妆品组合物和其他消耗材料组合物中化合物的量,如上面定义的,各组分将贡献其特殊的嗅觉特性,但整个组合物的香味、味道和芬芳作用,将是每个香料成分作用的总和。如在此所用的味觉作用包括苦味和麻刺作用。因此,通过改进组合物中另一成分贡献的味道反应,本发明化合物可用于改变香料组合物的味道特性。量的变化,根据许多因素,包括其他成分,它们相对的量和希望的作用。
本发明还提供通过结合感官可接受量的这里所述化合物的水平,增强或改良食品盐香料。化合物可单独使用或与本发明其他增强化合物的盐结合使用。另外,本发明盐增强材料可与工艺上已知的其他盐增强组合物结合使用,包括但不限于,十六烷基氯化吡啶鎓,溴苄胺托西酸盐,各种多肽,抗坏血酸钙盐,氯化钠和氯化钾的混合物,如美国专利4,997,672;5,288,510;6,541,050和美国专利申请2003/0091721中所述。
本发明的咸味增强化合物,可应用于增强感知咸味的任何盐,这些盐使用在食品或饮料产品中。本发明化合物优选增强咸味的盐是:氯化钠,主要因为发现摄入大量的钠会对人体有不良的影响,希望在保持咸味的同时,减少盐含量。
另外,本发明化合物也可用于增强用作盐代用品的已知咸味化合物的感知咸味。这些化合物包括阳离子氨基酸和低分子量的二肽。这些化合物的特殊例子是盐酸精氨酸,盐酸赖氨酸和盐酸赖氨酸-鸟氨酸。这些化合物呈现咸味,但一般只在低浓度时使用,因为它们在高浓度时呈现苦味。因此,可在配制食品或饮料时先使用比达到要求咸味少一些的氯化钠,然后把足以加强所述咸食品或饮料达到要求味道的本发明化合物,加入所述食品或饮料。另外,通过用咸味阳离子氨基酸,低分子量二肽或它们的混合物,至少可部分代替盐,可进一步减少氯化钠的含量。
结合到食品中的本发明化合物的盐增强水平,约100份/十亿至100份/百万;优选约0.1份/百万至50份/百万;最优选约0.5份/百万至10份/百万。
这里使用的术语“食品”包括人类和动物可摄取的固体和液体材料,这些材料通常,但不必须,有营养价值。因此,食品包括食物制品,如:肉类,肉汁,汤,方便食品,麦芽,酒精和其他饮料,牛奶和奶制品,海产品,包括:鱼,甲壳类,软体动物等,甜品,蔬菜,谷类,软饮料,快餐,狗食和猫食,其他兽产品等。
在产品中,本发明的C10-C11-E2,E4-链二烯酰胺组分混合物的使用水平(按重量)大于10份/十亿,一般在最终产品中提供的水平约50份/十亿——200份/百万,更优选约100份/十亿——100份/百万。
本发明的C10-C11-E2,E4-链二烯酰胺组分的混合物的使用水平,根据产品而变化。例如,酒精饮料的使用水平(按重量)约0.5-25份/百万,优选约2-10份/百万,最优选约5-10份/百万。非酒精饮料的水平(按重量)约25份/十亿——2份/百万,优选约100份/十亿——0.5份/百万,更优选约150-400份/十亿。快餐食品使用本发明的C10-C11-E2,E4-链二烯酰胺组分的混合物水平约5-250份/百万,优选约25-200份/百万,最优选约35-75份/百万。
当本发明的C10-C11-E2,E4-链二烯酰胺组分混合物用在调味组合物中时,它们与传统调味材料或佐料结合使用。这种工艺上共-成分或调味佐料是众所周知的,并在文献中有大量的描述。这些辅佐材料的要求是:
(1)它们与本发明的C10-C11-E2,E4-链二烯酰胺组分的混合物是非反应性的;
(2)它们与本发明的C10-C11-E2,E4-链二烯酰胺组分的混合物在感官知觉上是相容的,因此,本发明的C10-C11-E2,E4-链二烯酰胺组分的混合物加入到最终消耗材料的味道,不会不利地受佐料的使用的影响;
(3)它们是摄取可接受的,无毒性的或无害的。
除了这些要求外,可使用常规材料,并广泛地包括其他香料,赋形剂,稳定剂,增厚剂,表面活性剂,调节剂和增香剂。
这些常规调味料包括饱和脂肪酸,不饱和脂肪酸和氨基酸;醇,包括伯醇和仲醇;酯;羰基化合物,包括酮,内酯;其他环状有机材料,包括苯衍生物;无环化合物;杂环化合物,如呋喃,吡啶,吡嗪等;含硫化合物,包括硫醇,硫化物,二硫化物等;蛋白质;脂质;碳水化合物;所谓增味剂的,如谷氨酸单钠;谷氨酸镁,谷氨酸钙,鸟苷酸盐和肌苷酸盐;天然调味料,如:水解液,可可粉,香草和焦糖;香精油和提取物,如茴芹油,丁香油等,人造调味料,如香草基丁基醚,乙基香草醛等。
特殊的优选调味佐料包括但不限于下列物品:茴芹油;2-甲基-丁酸乙酯;香草醛;顺式-3-庚烯醇;顺式-3-己烯醇;反式-2-庚烯醛;戊酸丁酯;2,3-二乙基吡嗪;甲基环戊烯酮(methyl cyclopentenolone);苯甲醛;缬草油;3,4-二甲氧基苯酚;乙酸戊酯;肉桂酸戊酯;γ-丁酸内酯;糠醛;三甲基吡嗪;苯基乙酸;异戊醛;乙基麦芽酚;乙基香草醛;戊酸乙酯;丁酸乙酯;可可提取液;咖啡提取液;胡椒薄荷油;荷兰薄荷油;丁香油,茴香脑;小豆蔻油;冬青油;肉桂醛;2-甲基戊酸乙酯;γ-己烯基内酯;2,4-癸二烯醛;2,4-庚二烯醛;甲基噻唑醇(4-甲基-5-β-羟乙基噻唑);2-甲基丁硫醇;4-巯基-2-丁酮;3-巯基-2-戊酮;1-巯基-2-丙烷;苯甲醛;糠醛;糠醇;2-巯基丙酸;烷基吡嗪;甲基吡嗪;2-乙基-3-甲基吡嗪;四甲基吡嗪;多硫化物;二丙基二硫化物;甲基苄基二硫化物;烷基噻吩;2,3-二甲基噻吩;5-甲基糠醛;乙酰基呋喃;2,4-癸二烯醛;邻甲氧基苯酚;苯基乙醛;β-癸内酯;d-柠檬油精;3-羟基-2-丁酮;乙酸戊酯;麦芽糖醇;丁酸乙酯;乙酰丙酸;胡椒醛;乙酸乙酯;正辛醛;正戊醛;正己醛;丁二酮;谷氨酸单钠;谷氨酸单钾;含硫氨基酸,例如,半胱氨酸;水解蔬菜蛋白;2-甲基呋喃-3-硫醇;2-甲基二氢呋喃-3-硫醇;2,5-二甲基呋喃-3-硫醇;水解鱼蛋白;四甲基吡嗪;丙基丙烯基二硫化物;丙基丙烯基三硫化物;二烯丙基二硫化物;二烯丙基三硫化物;二丙烯基二硫化物;二丙烯基三硫化物;4-甲基-2-[(甲硫基)-乙基]-1,3-二硫戊环;4,5-二甲基-2-(甲硫基甲基)-1,3-二硫戊环;和4-甲基-2-(甲硫基甲基)-1,3-二硫戊环。
本发明的C10-C11-E2,E4-链二烯酰胺混合物的组分或它们的组合物,如上面提到的,可与一个或多个赋形剂或载体结合一起,加入到具体产品中。赋形剂可以是水溶性或油溶性可食用的,或者是适合的材料,如:三醋精,植物油,柠檬酸三乙酯,乙醇,丙二醇,水等。载体包括的材料,如阿拉伯树胶,角叉胶,黄原胶,瓜耳胶等。
根据本发明制备的C10-C11-E2,E4-链二烯酰胺混合物的组分,通过常规的方法与载体结合,比如喷雾干燥,挤压,滚筒干燥等。这些载体还包括将C10-C11-E2,E4-链二烯酰胺混合物的组分凝聚的材料,提供装入胶囊的产品,如前面提到的。当载体是乳状液时,调味料组合物也可含有乳化剂,如单和二甘油酯或脂肪酸等。用这些载体或赋形剂,可制备组合物要求的物理形式。
使用的本发明C10-C11-E2,E4-链二烯酰胺混合物的组分的量,应足以赋予产品要求的调味特性,但在另一方面,过量使用不仅浪费而且不经济,但在有些情况下,太大的量可能使香味或消费产品的其他特殊感觉的性质失去平衡。根据最终食品,可变化使用的量;最初出现在食品中香料的量和类型,食品经受进一步加工或处理的步骤;地区和其他偏好因素;如果有,产品储存的类型;由最终消费者赋予产品的消费前(preconsumption)处理,如烤,煎等。所以,术语“有效量”和“足够量”在本发明文本中理解为:数量上适合改变食品的香味。
参考图1,在位置10的干荜茇或菩提胡椒果实,经传送带11运到碾磨装置12,在那里碾磨成粒径约300-800微米。经碾磨的颗粒,经管线13传送到抽提器14上支撑筛子15上(起抽提柱台作用)。抽提器(抽出器)14中的温度曲线和热传递速率,通过在入口24和出口23的进、出加热夹套抽吸的液体控制。提取溶剂(例如正己烷)从溶剂供应容器16,经控制阀18,通过管线17流进抽提器(抽出器)14,用循环溶剂泵21,使提取溶剂通过支撑的筛子,通过管线19经阀门20再循环。在10-20小时后,以溶剂∶固体比例约2.75∶1至3.25∶1,泵21的操作暂时停止,同时含提取产品的液体提取液从抽提器,通过控制阀26,经管线25,进入提取液容器90取出。然后,第二次,提取溶剂,如正己烷,用循环溶剂泵21,从溶剂供应容器16,通过管线17,经控制阀18,流进抽提器14,提取溶剂通过支撑筛子和管线19,通过阀门20再循环。10-20小时后,以溶剂∶固体比例约1.75∶1至2.25∶1,泵21的操作暂时停止,同时含提取产品的液体提取液从抽提器,通过控制阀26,经管线25,进入提取液容器90而取出。然后,第三次,提取溶剂,如正己烷,用循环溶剂泵21,从溶剂供应容器16,通过管线17,经控制阀18,流进抽提器(也称为抽出器)14,提取溶剂通过支撑筛子和管线19,通过阀门20再循环。在10-20小时后,以溶剂∶固体比例约0.75∶1至1.25∶1,泵21的操作暂时停止,同时含提取产品的液体提取液从抽提器,通过控制阀26,经管线25,进入提取液容器90而取出。容器90中的混合的提取液,经管线27,经控制阀28,进入过滤装置29,在这里沉淀通过传送带30丢弃到排出装置31,滤液经管线32,通过阀门33,进入蒸发器34。在蒸发器34的操作时,顶部溶剂蒸汽经管线35,通过控制阀36,回到溶剂供应容器16而再循环。浓缩的提取液通过管线37,经控制阀38,进入储存容器40。或者,浓缩的提取液通过管线41,经控制阀42,进入分馏柱43,在此,残留物通过管线44取出并进到排出装置45,顶部蒸馏液(含本发明C10-C11-E2,E4-链二烯酰胺混合物)通过管线46和热交换器47,经控制阀48,通过管线49,经控制阀50,进入产品容器53,;及通过管线51,经控制阀52,进入‘废料部分’容器54。或者,当通过抽提器14的循环提取溶剂是乙醇时,浓缩的提取液通过管线55,经控制阀56,进入液体-液体多级提取柱57(用于正己烷∶乙醇交换),而同时正己烷从储存容器58,通过管线59,经控制阀60,进入多级抽提器57,与从管线34进入多级抽提器57的浓缩提取液流逆向流。乙醇馏分从抽提器57流出,经管线71进入乙醇馏分储存容器72。通过管线61、经控制阀62、流出抽提器57的正己烷,在蒸发器63中浓缩。从蒸发器63流出的正己烷溶剂通过管线67、经阀门66进入容器68,在那里溶液经管线69通过控制阀70回收到替换溶液供应容器16(它与作为乙醇源的容器是分开的)。同时,浓缩的正己烷提取液从蒸发器63排出经管线64经控制阀65进入分馏柱43,在那里残留物通过管线44排出送到排出装置45,而包含本发明的C10-C11-E2,E4-链二烯酰胺混合物的的柱顶馏出物通过管线46和热交换器47通过控制阀48通过管线49经控制阀50进入产品容器53;及通过管线51经控制阀52进入废弃馏份容器54。
参考图2,“X”轴,水平轴,用参考数211表示,“Y”轴用参考数210表示。参考数200表示的峰,是N-异丁基-E2,E4-癸二烯酰胺。参考数201表示的峰,是N-异丁基-E2,E4-十一碳二烯酰胺。参考数202表示的峰,是N-吡咯烷基-E2,E4-癸二烯酰胺。参考数203表示的峰,是N-哌啶基-E2,E4-癸二烯酰胺。
参考图3,“X”轴,水平轴,用参考数311表示,“Y”轴用参考数310表示。参考数300表示的峰,是N-异丁基-E2,E4-癸二烯酰胺。参考数301表示的峰,是N-异丁基-E2,E4-十一碳二烯酰胺。参考数302表示的峰,是N-吡咯烷基-E2,E4-癸二烯酰胺。参考数303表示的峰,是N-哌啶基-E2,E4-癸二烯酰胺。
参考图4,用参考数400表示的“Y”轴,表示(a)等级刻度1-9表示喜爱度刻度和强度;b)持续时间(单位:分钟)。“X”轴,水平轴,由参考数410表示。用下标“a”表示的条形图是强度。用下标“b”表示的条形图是喜爱度。用下标“c”表示的条形图是持续时间。
下面表II列出供比较的具体物质,它们由具体参考数识别:
比较的物质 | 参考数 |
30%蒲桃(Jambu)提取物(在10ppm测试) | 411 |
95%天然千日菊酰胺(在10ppm测试) | 412 |
25%赛菊芋(在10ppm测试) | 413 |
菩提胡椒(含5%本发明C10-C11-E2,E4-链二烯酰胺混合物)(在10ppm测试) | 414 |
荜茇(含35%本发明C10-C11-E2,E4-链二烯酰胺混合物)(在10ppm测试) | 415 |
98%墙草碱(在10ppm测试) | 416 |
N-异丁基-E2,Z6-十二碳二烯酰胺(在10ppm测试) | 417 |
N-异丁基-E2,E4,Z8-十一碳三烯酰胺(在10ppm测试) | 418 |
参看图5,“Y”轴(用参考数500表示)表示持续时间(分钟)。“X”轴(水平轴)用参考数510表示。
下面表III列出供比较的具体物质,它们由具体参考数识别:
表III
比较的物质 | 参考数 |
30%蒲桃(Jambu)提取物(在10ppm测试) | 511 |
25%赛菊芋(Chilcuan)提取物(在10ppm测试) | 512 |
25%赛菊芋提取物(在20ppm测试) | 513 |
荜茇(含35%本发明C10-C11-E2,E4-链二烯酰胺混合物)(在10ppm测试) | 514 |
荜茇(含25%本发明C10-C11-E2,E4-链二烯酰胺混合物)(在10ppm测试) | 515 |
荜茇(含7%本发明C10-C11-E2,E4-链二烯酰胺混合物)(在10ppm测试) | 516 |
菩提胡椒(含5%本发明C10-C11-E2,E4-链二烯酰胺混合物)(在10ppm测试) | 517 |
墙草碱98%(在10ppm测试) | 518 |
天然千日菊酰胺95%(在20ppm测试) | 519 |
天然千日菊酰胺95%(在10ppm测试) | 520 |
N-异丁基-E2,E4,Z8-十一碳三烯酰胺(在20ppm测试) | 521 |
N-异丁基-E2,E4,Z8-十一碳三烯酰胺(在10ppm测试) | 522 |
N-异丁基-E2,Z6-壬二烯酰胺(在10ppm测试) | 523 |
N-异丁基-E2,Z6-十一碳二烯酰胺(在10ppm测试) | 524 |
下面的例子,作为本发明的特殊实施例提供。不偏离本发明的范围,本发明的其它改进随时出现在本领域的技术人员面前。除非另行说明,规范和下列实施例中的所有百分率,如这里使用的,是重量百分率。
实施例1
C
10
-C
11
-E2,E4-链二烯酰胺混合物的组分的制备
用下列反应次序,制备特色化合物,它们的NMR数据如下:
2,4-二烯酸溶解在二氯甲烷中,在0℃到室温的温度范围,最优选10-20℃,加入1.0-2.0当量的氯甲酸乙酯。把形成的溶液冷却到-10℃-+10℃,加入1.0-20.当量的三乙胺,温度范围低于10℃,在室温下,使混合物老化1小时。过滤混合物,滤液冷却到0℃。
加入1.0-4.0当量的胺,室温老化反应约1-3小时。用10%含水盐酸终止反应,用10%氢氧化钠洗涤,接着用氯化钠溶液洗涤,并除去溶剂。
根据物理性质,用蒸馏或重结晶纯化粗产物。以酸为基础,反应的产率为40-60摩尔%。
根据上面的一般方法和下面的特殊例子,合成酰胺。提到的当量,是基于起始酸的摩尔当量,收率是基于起始酸的纯化化合物收率。
N-异丁基E2,E4-癸二烯酰胺
E2,E4-癸二烯酸1当量,氯甲酸乙酯1.5当量,三乙胺1.5当量,异丁基胺3.0当量,按一般程序终止反应,收率=45%。
0.89ppm (t,3H,J=6.92Hz)
0.92ppm (d,6H,J=6.71Hz)
1.30ppm (m,4H)
1.42ppm (pentet,2H,J=7.19Hz)
1.80ppm (septet,1H,J=6.73Hz)
2.14ppm (q,2H,J=6.88Hz)
3.16ppm (t,2H,J=6.48Hz)
5.57ppm (br,s,1H)
5.76ppm (d,1H,J=15.04Hz)
6.04-6.17ppm (m,2H)
7.19ppm (d,J=9.85Hz的d,1H,J=14.98Hz,)
N-异丁基E2,E4-十一碳二烯酰胺
E2,E4-十一碳二烯酸1当量,氯甲酸乙酯1.5当量,三乙胺1.5当量,异丁基胺3.0当量,按一般程序终止反应,收率=40%。
0.88ppm (t,3H,J=6.82Hz)
0.92ppm (d,6H,J=6.70Hz)
1.28ppm (m,6H)
1.41ppm (pentet,2H,J=6.88Hz)
1.80ppm (septet,1H,J=6.73Hz)
2.14ppm (q,2H,J=6.83Hz)
3.16ppm (t,2H,J=6.48Hz)
5.55ppm (br,s,1H)
5.76ppm (d,1H,J=15.03Hz)
6.04-6.17ppm (m,2H)
7.19ppm (d,J=9.86Hz的d,1H,J=14.98Hz,)
N-哌啶基E2,E4-癸二烯酰胺
E2,E4-癸二烯酸1当量,氯甲酸乙酯1.1当量,三乙胺1.2当量,哌啶1.25当量,按一般程序终止反应,收率=40%。
0.89ppm (t,3H,J=6.92Hz)
1.30ppm (m,4H)
1.42ppm (pentet,2H,J=7.19Hz)
1.56ppm (m,4H)
1.64ppm (m,2H)
2.14ppm (q,2H,J=7.04Hz)
3.49ppm (br,s,2H)
3.60ppm (br,s,2H)
6.06ppm (m,1H)
6.18ppm (2d,1H,J=10.82Hz)
6.27ppm (d,1H,J=14.79Hz)
7.23ppm (d,J=10.73Hz的d,1H,J=14.74Hz,)
N-吡咯烷基E2,E4-癸二烯酰胺
E2,E4-癸二烯酸1当量,氯甲酸乙酯1.1当量,三乙胺1.2当量,吡咯烷1.5当量,按一般程序终止反应,收率=58%。
0.89ppm (t,3H,J=6.90Hz)
1.30ppm (m,4H)
1.42ppm (pentet,2H,J=7.10Hz)
1.86ppm (pentet,2H,J=7.40Hz)
1.96ppm (pentet,2H,J=6.50Hz)
2.15ppm (q,2H,J=7.10Hz)
3.53ppm (2t,4H,J=6.96Hz)
6.06-6018ppm (m,2H)
6.09ppm (d,1H,J=14.87Hz)
7.27ppm (d,J=10.57Hz的d,1H,J=14.83Hz,)
实施例IIA
用在实施例IIB香波中的香料的制备
与实施例II香波一起使用的下列香料的制备:
成分 | 重量份 |
α-鸢尾酮 | 7.0 |
肉豆蔻醚 | 4.0 |
2-甲氧基萘 | 3.0 |
苯甲醛 | 2.0 |
β-苯基乙基醇 | 12.0 |
橙花醇 | 7.0 |
丁子香酚 | 8.0 |
异丁子香酚 | 2.0 |
水杨酸戊酯 | 4.0 |
β-石竹烯 | 14.0 |
乙酸柏木酯 | 16.0 |
水杨酸环己酯 | 4.0 |
γ-十二烷内酯 | 3.0 |
氨茴酸香叶酯 | 3.0 |
实施例IIB
与实施例IIC香料(下述)联合使用的含香料香波基物的制备
根据实施例IIA,以0.8%的比例,制备香料,并与下列含水香波基料混合:
组分 | 重量份 |
十二烷基硫酸铵(27%水溶液) | 56.0 |
柠檬酸 | 0.50 |
柠檬酸钠 | 0.50 |
椰子单乙醇酰胺 | 5.0 |
乙二醇二硬酯酸酯 | 3.0 |
对羟基苯甲酸甲酯 | 0.50 |
对羟基苯甲酸丙酯 | 0.50 |
颜色溶液 | 0.20 |
水 | 33.8 |
实施例IIC
在实施例IIB的香波中,以1%的比率加入2-巯氧吡啶锌,以0.3%的比率加入下列混合物,它的组分根据实施例I制备。
组分 | 重量份 |
N-异丁基-E2,E4-癸二烯酰胺 | 45 |
N-异丁基-E2,E4-十一碳二烯酰胺 | 25 |
N-吡咯烷基-E2,E4-癸二烯酰胺 | 5 |
N-哌啶基-E2,E4-癸二烯酰胺 | 10 |
在使用中和使用香波后5分钟,起实际麻刺作用,在1-9刻度上的值9。
实施例III
制备下列冲鼻香料:
组分 | 重量份(克) |
苯甲醛 | 500 |
单折橙油 | 415 |
单折圆柚油 | 33.4 |
己酸乙酯 | 16.6 |
丁酸乙酯 | 16.6 |
异戊酸乙酯 | 8.3 |
丙酸乙酯 | 3.3 |
α紫罗酮 | 0.1 |
茉莉净油 | 0.1 |
香叶醇 | 3.3 |
乙酸异戊酯 | 3.3 |
4,8-二甲基-3,7-壬二烯-2-基2-甲基-2-戊烯酸酯 | 6.5 |
实施例IIIB
(i)粉状香料
20克实施例IIIA的香料组合物,在含300克阿拉伯树胶和700克水的溶液中乳化。用Browen实验室干燥器,以250立方英尺/分钟空气、入口温度500,出口温度200,轮子转速50000转/分钟喷干。
(ii)糊状混合物
300克实施例IIIA的液体香料和1公斤Cab-O-Sil M-5(Cobot Corporation ofBoston,Massachussetts)硅石,通过激烈搅拌将硅石分散在液体香料中制备。然后将(i)中制备的粉状香料,在25℃混合到形成粘稠液体中,搅拌约30分钟,形成持续释放的香料糊。
实施例IIIC
在Hobart混合器中,98.15重量份的山梨醇与0.05重量份的FD&C#色淀黄(Warner Jenkinson)混合。
在形成的混合物中,搅拌下加入下列物质:
(a)0.60重量份的实施例IIIB的糊状混和物;
(b)0.40重量份的研磨的柠檬酸;
(c)0.30重量份的下列混合物,组分根据实施例I制备:
组分 | 重量份 |
N-异丁基-E2,E4-十一碳二烯酰胺 | 45 |
N-异丁基-E2,E4-十一碳二烯酰胺 | 25 |
N-吡咯烷基-E2,E4-癸二烯酰胺 | 5 |
N-哌啶基-E2,E4-癸二烯酰胺 | 10 |
0.8重量份的硬脂酸镁加入到形成的混合物,形成的混合物压成片,生成有令人愉快‘麻刺’效果的橙色-压制的香片。
实施例IV
本发明的下列化合物,通过下列材料,以上面描述的反应次序反应制备。
N-环丙基-2E,4E-己二烯酰胺
2,4-己二烯酸1当量,氯甲酸乙酯1.05当量,三乙胺1.2当量,环丙胺1.3当量,作为在THF中的2.0M溶液,用10%氯化钠终止反应,收率=51%。
0.54ppm(m,2H),0.79ppm(m,2H),1.82ppm(d,3H,J=5.93Hz),2.80ppm(m,1H),5.72ppm(d,1H),6.00ppm(br,s,1H),6.03-6.15ppm(m,2H),7.18ppm(d,1H,J=14.98Hz,of d,J=10.02Hz)。
N-环丙基-4Z-庚烯酰胺
4-庚烯酸1当量,氯甲酸乙酯1.1当量,三乙胺1.2当量,环丙胺1.5当量,作为在THF中的2.0M溶液,用10%氯化钠终止反应,收率=67%。
0.49ppm(m,2H),0.75ppm(m,2H),0.96ppm(t,3H,J=7.553Hz),2.06ppm(m,2H),2.18(m,2H),2.36(m,2H),2.70(m,1H),5.30ppm(m,1H),5.43ppm(m,1H),5.97ppm(br,s,1H)。
N-乙基-2E,4E-己二烯酰胺
2E,4E-己二烯酸1当量,氯甲酸乙酯1.12当量,三乙胺1.2当量,乙胺1.5当量,作为在THF中的2.0M溶液,用10%氯化钠终止反应,收率=26%。
1.16ppm(t,3H,J=7.27Hz),1.82ppm(d,3H,J=6.09Hz),3.36ppm(q,2H,J=7.26Hz of d,J=5.73),5.77ppm(d,1H,J=14.96Hz),5.93ppm(br,s,1H),6.01-6.18ppm(m,2H),7.19ppm(d,1H,J=14.94Hz,of t,J=10.14Hz)。
N-环丙基-3Z-己烯酰胺
3Z-己烯酸1当量,氯甲酸乙酯1.1当量,三乙胺1.2当量,环丙胺1.5当量,作为在THF中的2.0M溶液,用10%氯化钠终止反应,收率=77%。
0.49ppm(m,2H),0.75ppm(m,2H),0.98ppm(t,3H,J=7.48Hz),2.05ppm(d,2H,J=0.97Hz of pentet),2.70(octet,1H,J=3.59Hz),2.98ppm(d,2H,J=7.46Hz),5.46-5.52ppm(m,1H),(m,1H),5.58-5.66ppm(m,1H),6.19ppm(br,s,1H)。
N-环丙基-4Z-癸烯酰胺
4Z-癸烯酸1当量,氯甲酸乙酯1.1当量,三乙胺1.2当量,环丙胺1.13当量,作为在THF中的2.0M溶液,用10%氯化钠终止反应,收率=86%。
0.49ppm(m,2H),0.74ppm(m,2H),0.88ppm(t,3H,J=6.89Hz),1.26-1.37ppm(m,6H),2.04ppm(m,2H),2.18(m,2H),2.35(q,2H,J=7.33Hz),2.70(m,1H),5.30-5.44ppm(m,2H),6.04ppm(br,s,1H)。
Claims (7)
1.化合物,选自:
N-乙基E2,E4-己二烯酰胺;
N-环丙基E2,E4-己二烯酰胺;
N-环丙基Z4-庚烯酰胺;和
N-环丙基Z3-己烯酰胺。
2.增加、增强或赋予消耗材料香味、味道、物质感觉作用和/或抗菌作用的方法,其步骤是将所述消耗材料与有效浓度和数量的有香味、味道、物质感觉作用和/或抗菌作用的化合物相混合,所述化合物选自N-乙基E2,E4-己二烯酰胺,N-环丙基E2,E4-己二烯酰胺,N-环丙基Z4-庚烯酰胺,N-环丙基Z3己烯酰胺,N-甲基-E2,E4-己二烯酰胺,N-烯丙基E2,E4-己二烯酰胺和N,N-二甲基E2,E4-己二烯酰胺。
3.增强消耗材料咸味的方法,其步骤包括把所述的消耗材料与有效量的N-乙基E2,E4-己二烯酰胺,N-环丙基E2,E4-己二烯酰胺,N-环丙基Z4-庚烯酰胺,N-环丙基Z3-己烯酰胺,N-甲基E2,E4-己二烯酰胺,N-烯丙基E2,E4-己二烯酰胺和N,N-二甲基E2,E4-己二烯酰胺相混合。
4.增加、增强或赋予消耗材料香味、味道或躯体感觉作用的方法,消耗材料选自食品,饮料,口香糖,口腔护理产品,鼻护理产品,科龙香水,皮肤护理产品,头发护理产品,局部化装产品和药物产品,其步骤是在所述消耗材料中加入增加、增强或赋予香味、味道或躯体感觉作用的浓度和数量的化合物,化合物选自N-乙基E2,E4-己二烯酰胺,N-环丙基E2,E4-己二烯酰胺,N-环丙基Z4-庚烯酰胺,N-环丙基Z3-烯酰胺,N-甲基E2,E4-己二烯酰胺,N-烯丙基E2,E4-己二烯酰胺和N,N-二甲基E2,E4-己二烯酰胺。
5.增加、增强或赋予消耗材料咸味的方法,消耗材料选自食品,饮料,口香糖,口腔护理产品,局部化装产品和药物产品,其步骤是在所述消耗材料中加入增加、增强或赋予香味、味道或体觉作用的浓度和数量的至少一种化合物,化合物选自N-乙基E2,E4-己二烯酰胺,N-环丙基E2,E4-己二烯酰胺,N-环丙基Z4-庚烯酰胺,N-环丙基Z3-己烯酰胺,N-甲基E2,E4-己二烯酰胺,N-烯丙基E2,E4-己二烯酰胺和N,N-二甲基E2,E4-己二烯酰胺。
6.如权利要求5中所述的方法,其特征在于:其水平大于约10份/十亿。
7.在消耗材料和化合物的组合中,消耗材料选自食品,饮料,口香糖,口腔护理产品,局部化装产品和药物产品,化合物选自N-乙基E2,E4-己二烯酰胺,N-环丙基E2,E4-己二烯酰胺,N-环丙基Z4-庚烯酰胺,N-环丙基Z3-己烯酰胺,N-甲基E2,E4-己二烯酰胺,N-烯丙基E2,E4-己二烯酰胺和N,N-二甲基E2,E4-己二烯酰胺。
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US6365215B1 (en) | 2000-11-09 | 2002-04-02 | International Flavors & Fragrances Inc. | Oral sensory perception-affecting compositions containing dimethyl sulfoxide, complexes thereof and salts thereof |
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US20030095936A1 (en) | 2001-11-19 | 2003-05-22 | Orrea Light | Lip gloss composition |
ATE320196T1 (de) | 2001-12-27 | 2006-04-15 | Symrise Gmbh & Co Kg | Verwendung von ferulasäureamiden als aromastoffe |
US6579513B1 (en) | 2002-01-03 | 2003-06-17 | Playtex Products, Inc. | Hygiene mouthspray composition |
US6579543B1 (en) | 2002-02-22 | 2003-06-17 | Jackie H. McClung | Composition for topical application to skin |
KR100492309B1 (ko) * | 2002-03-20 | 2005-06-03 | 대한민국 | 후추 추출물을 유효성분으로 하는 살충 및 살균성 조성물 |
US6579514B1 (en) | 2002-05-08 | 2003-06-17 | David M. Hall | Anti infective periodontic compositions |
DE10227462A1 (de) | 2002-06-20 | 2004-01-08 | Symrise Gmbh & Co. Kg | Herstellung von cis-Pellitorin und Verwendung als Aromastoff |
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DE10253331A1 (de) | 2002-11-14 | 2004-06-03 | Symrise Gmbh & Co. Kg | Verwendung von trans-Pellitori als Aromastoff |
-
2004
- 2004-08-17 US US10/919,631 patent/US7329767B2/en not_active Expired - Fee Related
- 2004-09-29 BR BRPI0404249-2A patent/BRPI0404249B1/pt not_active IP Right Cessation
- 2004-10-01 ES ES08075120T patent/ES2377953T3/es active Active
- 2004-10-01 ES ES04256086T patent/ES2312931T3/es active Active
- 2004-10-01 DE DE602004015907T patent/DE602004015907D1/de active Active
- 2004-10-01 EP EP04256086A patent/EP1520850B1/en not_active Not-in-force
- 2004-10-01 EP EP08075120A patent/EP1927587B1/en not_active Not-in-force
- 2004-10-08 CN CNA200710147271XA patent/CN101139304A/zh active Pending
- 2004-10-08 CN CNB2004100835178A patent/CN100569738C/zh not_active Expired - Fee Related
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ES2377953T3 (es) | 2012-04-03 |
EP1520850A3 (en) | 2005-07-13 |
CN1736980A (zh) | 2006-02-22 |
EP1927587A2 (en) | 2008-06-04 |
EP1520850A2 (en) | 2005-04-06 |
CN100569738C (zh) | 2009-12-16 |
EP1927587A3 (en) | 2008-11-19 |
EP1520850B1 (en) | 2008-08-20 |
ES2312931T3 (es) | 2009-03-01 |
US20050075368A1 (en) | 2005-04-07 |
US7329767B2 (en) | 2008-02-12 |
EP1927587B1 (en) | 2011-12-07 |
BRPI0404249B1 (pt) | 2018-02-14 |
BRPI0404249A (pt) | 2005-06-28 |
DE602004015907D1 (de) | 2008-10-02 |
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