CN101106968A - 2-c-取代的丙烷-1,3-二羰基化合物及其在中和恶臭中的用途 - Google Patents
2-c-取代的丙烷-1,3-二羰基化合物及其在中和恶臭中的用途 Download PDFInfo
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- CN101106968A CN101106968A CNA2006800028602A CN200680002860A CN101106968A CN 101106968 A CN101106968 A CN 101106968A CN A2006800028602 A CNA2006800028602 A CN A2006800028602A CN 200680002860 A CN200680002860 A CN 200680002860A CN 101106968 A CN101106968 A CN 101106968A
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- 229910052794 bromium Inorganic materials 0.000 claims description 43
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Abstract
式1化合物作为恶臭中和剂的用途:其中A,B,Y和Y具有说明书中给出的相同含义,和包含它的个人护理产品。
Description
本发明涉及恶臭中和化合物和包含所述化合物的组合物。更特别地,本发明涉及某些亲电的烯烃及其羟基-和烷氧基-加合物。
恶臭是在空气和在许多基底,例如织物,硬表面,皮肤和毛发上遇到的令人讨厌的臭味。恶臭具有或者个人或者环境来源。例如,汗液,尿液和粪便恶臭来源于个人,而厨房和烹饪恶臭来源于环境。尽管个人恶臭容易沉积在织物,毛发和皮肤上,但环境恶臭也具有沉积在这些基底上的倾向。
胺类,硫醇类,硫化物,短链脂族和烯属酸,例如脂肪酸是在汗液,家庭和环境恶臭中发现的典型化学品且对其具有贡献。这些类型的恶臭典型地包括吲哚,粪臭素,和在盥洗室和动物臭味内发现的甲硫醇;在尿液内发现的哌啶和吗啉;在厨房和垃圾臭味内发现的吡啶和三乙胺;和在腋部恶臭中发现的短链脂肪酸,例如3-甲基-3-羟基己酸,3-甲基己酸或3-甲基-2-己烯酸。在例如Xiao-Nong Zeng等人的Journal of Chemical Ecology,Vol.17,No.7,1991,p.1469-1492中公开了腋部恶臭,在此通过参考将其引入。
已使用数种方法消除恶臭。这些方法包括通过用令人愉悦的较强的气味叠加恶臭的遮盖法,通过阻挡恶臭的嗅觉受体的交叉匹配法,根据Raoult定律,通过与引起负面偏差的成分混合来抑制恶臭的方法,通过多孔或笼状结构吸收恶臭来消除恶臭的方法,和通过诸如抗微生物和酶抑制剂之类的路线来避免恶臭形成的方法。尽管本领域已知的方法能中和一些恶臭,但仍需要甚至更加有效对抗恶臭的进一步的化合物。
令人惊奇的是,发明人已发现能中和恶臭的一组新化合物。
因此,本发明第一方面涉及式1化合物作为恶臭中和剂的用途:
其中
X和Y独立地为选自下述的残基:
-CR1R2R3中,其中R1,R2和R3独立地为H,烃残基或含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
-NR4R5,其中R4和R5独立地为H,烃残基,优选C1-C20烷基,例如甲基,乙基,丙基,丁基,异丁基,2-乙基己基,C4-C8环烷基,例如环戊基和环己基;或者R4和R5与它们连接到其上的氮原子一起形成3,5或6-元环;或者含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;和
-OR6,其中R6是烃残基,优选R6是C1-C20烷基,例如甲基,乙基,丙基,丁基,异丁基,2-乙基己基,叔丁基;C3-C8环烷基,例如环丁基,环戊基和环己基;C3-C10烯基,例如丙烯基,异丙烯基和异丁烯基;C6-C10芳基,例如苯基或萘基;或C7-C10烷芳基,例如苄基;或者R6是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
A是H或者-COOR7,其中R7是烃残基,优选C1-C5烷基,例如甲基,乙基,丙基,丁基,异丁基和叔丁基;C2-C5烯基,例如丙烯基,异丙烯基和异丁烯基;C6-C10芳基,例如苯基和萘基;C7-C10烷芳基,例如苄基;或者含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
-C(O)R8,其中R8是烃残基,优选C1-C5烷基,例如甲基,乙基,丙基,丁基,异丁基和叔丁基;C3-C5烯基,例如丙烯基,异丙烯基和异丁烯基;C6-C10芳基,例如苯基和萘基;C7-C10烷芳基,例如苄基;或者含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;或者
-CR9R10R11,其中R9,R10和R11独立地为H,烃残基或含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
B是H;-CR12R13R14,其中R12,R13和R14独立地为H,烃残基;-OC(O)R18,其中R18是H或烃残基,优选C1-C20烷基,例如甲基,乙基,丙基,丁基,异丁基,2-乙基己基和叔丁基;C3-C8环烷基,例如环丁基,环戊基和环己基;C3-C10烯基,例如丙烯基,异丙烯基和异丁烯基;C6-C10芳基,例如苯基或萘基;或C7-C10烷芳基,例如苄基;或R12,R13和R14独立地为含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;和
虚线与碳-碳键一起代表双键;或者
B是-NR16R17,其中R16和R17独立地为H,烃残基,优选C1-C20烷基,例如甲基,乙基,丙基,丁基,异丁基,2-乙基己基和叔丁基;或者C3-C8环烷基,例如环丁基,环戊基和环己基;或者含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;或者
-OR15,其中R15是H,烃残基,优选C1-C20烷基,例如甲基,乙基,丙基,丁基,异丁基,2-乙基己基和叔丁基;C3-C8环烷基,例如环丁基,环戊基和环己基;C3-C10烯基,例如丙烯基,异丙烯基和异丁烯基;C6-C10芳基,例如苯基或者萘基;或者C7-C10烷芳基,例如苄基;或者R15是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;和
虚线与碳-碳键一起代表单键或双键;
条件是A和B不同时为氢。
其中虚线与碳-碳键一起代表单键的式1化合物还包括它的所有的互变异构形式。
尤其优选的是下述式1化合物,其中X或Y是式-CR1R2R3的残基,其中R1,R2和R3与它们连接到其上的碳原子一起形成选自下述的残基:
C1-C20烷基,例如甲基,乙基,丙基,丁基,异丁基,乙基己基和叔丁基,
含有选自O,N,Si,Cl和Br中的至少一个杂原子的C1-C20烷基,例如乙氧基乙基,甲氧基乙基,2-乙氧基-2-甲基乙基,氰基甲基,乙酰氨基乙基,二乙基氨基氨基甲酰基乙基和三甲基甲硅烷氧基乙基;
C3-C8环烷基,例如环戊基,环己基和环辛基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C3-C8环烷基,例如氧杂环丙基和四氢呋喃基;
C6-C12烷基环烷基,例如甲基环己基,乙基环己基和甲基环戊基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C6-C12烷基环烷基,例如(4-羟基)-环己基甲基;
C6-C12环烷基烷基,例如(4-甲基)-环己基和2-(2-丁基)-环己基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C6-C12环烷基烷基,例如(4-甲氧基)-环己基,(2-甲氧基)-环己基和4-氮杂环己基;
C2-C10烯基,例如丙烯基,异丙烯基,异丁烯基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C2-C10烯基,例如乙氧基乙烯基和(2-丙烯氧基)-乙基;
C2-C10炔基,例如丙炔基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C2-C10炔基;
C6-C10芳基,例如苯基;
被选自C1-C15烷基和C1-C15烷氧基中的至少一个取代基取代的C6-C10芳基,例如对甲氧基苯基;
C5-C10杂芳基,例如吡啶基,呋喃基,吡咯基,咪唑基;
C7-C10烷芳基,例如苄基;和
被选自C1-C15烷基,C1-C15烷氧基,氨基,C1-C15烷基氨基和C2-C30二烷基氨基中的至少一个取代基取代的C7-C10烷芳基,例如甲氧基苄基,羟基苄基,二羟基苄基,(2-羟基-4-甲氧基)-苄基和(2-羟基-4-氰基)-苄基。
其中A是-CR9R10R11的式1化合物包括如下化合物:其中R9,R10和R11与它们连接到其上的碳原子一起形成选自C1-C20烷基,例如甲基,乙基,丙基,丁基,异丁基,2-乙基己基和叔丁基的烃残基;C4-C8环烷基,例如环戊基和环己基;C3-C10烯基,例如丙烯基,异丙烯基和异丁烯基;C6-C10芳基,例如苯基和萘基;被选自羟基,C1-C5烷氧基,苯氧基,苄氧基,乙酰基,苯甲酰基,氨基,C1-C5烷基氨基,C1-C5二烷基氨基,硝基,氯和溴中的至少一个取代基取代的C6-C10芳基,例如(2-羟基-5-硝基)苯基,(2-羟基-5-乙酰基)苯基,(2-羟基-4-甲氧基)苯基,(2-羟基)苯基和(3-乙氧基-4-羟基)苯基;和C5-C8杂芳基,例如吡啶基,呋喃基,吡咯基和咪唑基。
其中B是-CR12R13R14的式1化合物包括如下化合物:其中R12,R13和R14与它们连接到其上的碳原子一起形成选自C1-C10烷基,例如甲基,乙基,丙基,丁基,异丁基,2-乙基己基和叔丁基的烃残基;C4-C8环烷基,例如环戊基和环己基;C3-C10烯基,例如丙烯基,异丙烯基和异丁烯基;和C6-C10芳基,例如苯基或萘基。
还优选的是其中A是-CR9R10R11和B是氢或-CR12R13R14的式1化合物,和其中A是-COOR7或-C(O)R8和B是氢或选自-CR12R13R14,-NR16R17和-OR15中的残基的式1化合物。
优选的是其中B是-NR16R17和R16加上R17中的碳原子之和大于10的式1化合物。
尤其优选的是在实施例1-34中具体地描述的式1化合物。
还优选的是选自如下的式1化合物:
2-(3,7-二甲基-辛-2,6-二亚烯基)-丙二酸二乙酯;
3-亚辛基-戊烷-2,4-二酮;
2-吡啶-2-基亚甲基-丙二酸二乙酯;
2-亚辛基-丙二酸二甲酯;
2-乙氧羰基-丁-2-烯二酸二乙酯;
2-乙酰基-戊-2-烯酸乙酯;
2-亚辛基-丙二酸二乙酯;
2-亚癸基-丙二酸二乙酯;
2-乙酰基-癸-2-烯酸乙酯;
2-(2-羟基-亚苄基)-1-苯基-丁烷-1,3-二酮;
2-(2-羟基-亚苄基)-丙二酸二乙酯;
3-(2-羟基-亚苄基)-戊烷-2,4-二酮;
3-(2-羟基-4-甲氧基-亚苄基)-戊烷-2,4-二酮;
2-(2-羟基-亚苄基)-3-氧代-丁酸乙酯;
2-乙氧羰基-氧基亚甲基-丙二酸二乙酯;和
2-乙酰氧基亚甲基-丙二酸二乙酯。
发明人发现本发明的化合物能通过与含-SH,-NHR或-NH2中的官能团反应来中和含所述基团的恶臭化合物,从而中和恶臭。此外,本发明的化合物能通过化学反应来与氨反应。认为通过其中虚线与碳-碳键一起代表双键的式1化合物来中和恶臭化合物是借助该官能团加成到亲电双键上来实现的,而在没有束缚于理论的情况下,认为通过其中虚线与碳-碳键一起代表单键的式1化合物来中和恶臭化合物是借助消除/加成机理来实现的。
令人惊奇的是,还发现式1化合物中和含羧酸基的恶臭化合物,例如3-甲基己酸。
发现式1化合物对恶臭化合物的活性比例如二己基富马酸酯(DHF)大得多,尤其在含水环境内,正如实施例中所示。因此,需要浓度低得多的本发明化合物实现与由DHF获得的相类似的恶臭下降。二己基富马酸酯长期以来用作恶臭消除剂,因此被选择作为对比例。
“活性”是指恶臭化合物的顶空(headspace)浓度(%)下降。通过GC-MS分析确定体积试样的顶空,从而分析顶空,正如在实施例中更加详细地描述的一样。
可使用常规技术和方法,或者通过直接混合本发明的化合物到消费产品内或者通过混合含式1化合物的组合物,例如,含进一步的成分,例如香料的醇或水溶液,将本发明的化合物掺入到宽泛范围的消费产品内。因此,本发明另外提供含式1化合物作为活性成分的组合物。此外,本发明提供制造含所述化合物作为活性成分的消费产品的方法。
有效中和恶臭所要求的本发明化合物的用量取决于这一化合物掺入其内的产品类型。此外,它可取决于环境条件,例如湿度和pH。例如,若在除味剂喷雾剂或者室内除味喷雾剂中使用时,该产品可占最终产品的约0.01-约10%wt/wt,优选约0.1-约1%wt/wt。若在室内除味过滤装置,例如炊具容器中使用时,该化合物的用量范围可以是过滤器重量的约0.1%-约20%wt/wt。因此,本发明的方面之一涉及含约0.01-约20wt%式1化合物或其混合物的消费产品。
本发明进一步的方面是赋予基底,例如皮肤,毛发或织物恶臭中和作用,该方法包括使基底与含式1化合物的消费产品接触的步骤。
本发明还包括将含式1化合物的消费产品分散在有限空间,例如房间,柜子,盒子和抽屉内的方法。该方法包括将式1化合物掺入到消费产品内,并通过例如喷洒,雾化和/或挥发,将有效量的消费产品分散在该空间内。
此处所使用的“消费产品”包括例如化妆品,其中包括诸如除味剂,止汗剂,润肤霜和洗剂,香波,香水和牙膏之类的产品,和家庭护理与织物护理产品,其中包括诸如空气清新剂,表面清洁剂,洗涤剂,织物调节剂,织物的漂洗调节剂之类的产品,和应用到衣服,室内装饰品,窗帘,地毯和吸收剂材料上的产品。
此处所使用的化妆品是指拟施加到人体上以供清洁,美化,提高吸引力,或在没有影响身体结构功能的情况下改变外观的制品。
吸收剂材料包括诸如猫砂(cat litter)和过滤器之类的制品。在特别的实施方案中,术语“过滤器”是指例如在厨房,球室,废物箱,汽车和冰箱内用作降低空气恶臭的部分装置的任何种类的过滤器。这种装置包括炊具容器,真空吸尘器和猫砂盒。
消费产品可以是例如通过倾倒或喷洒施加到表面上的液体形式;固体形式,例如粉末或者压缩粉末形式,或者为蜡烛形式,或者为半固体,例如凝胶。
尽管在文献中公开了一些化合物,但没有公开其它化合物且它们是新的。因此,在本发明的另一方面中,提供式1a化合物:
其中
X和Y具有与以上给出的相同含义,
A是-COOR7,其中R7是烃残基,优选C1-C5烷基,例如甲基,乙基,丙基,丁基,异丁基和叔丁基;C2-C5烯基,例如丙烯基,异丙烯基和异丁烯基;C6-C10芳基,例如苯基和萘基;C7-C10烷芳基,例如苄基;或者含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;或者
A是-C(O)R8,其中R8是烃残基,优选C1-C5烷基,例如甲基,乙基,丙基,丁基,异丁基和叔丁基;C3-C5烯基,例如丙烯基,异丙烯基和异丁烯基,C6-C10芳基,例如苯基和萘基;C7-C10烷芳基,例如苄基;或者含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
B是-NR16R17,其中R16和R17独立地为H或烃残基;或者
R16和R17独立地为含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;或者
B是-OR15,其中R15是H,或烃残基,优选C1-C20烷基,例如甲基,乙基,丙基,丁基,异丁基,2-乙基己基和叔丁基;C3-C8环烷基,例如环丁基,环戊基和环己基;C3-C10烯基,例如丙烯基,异丙烯基和异丁烯基;C6-C10芳基,例如苯基或萘基;或者C7-C10烷芳基,例如苄基;或者
R15是含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的烃残基;
和虚线与碳-碳键一起代表单键;
条件是
若X-Y是乙氧基,则B不是甲氧基;和
若X是乙氧基和Y是甲基,则B不是甲氧基或乙氧基。
特别的实施方案中是其中A是-COOC2H5和B是羟基或-O-C2H5的式1a化合物,例如:
3-乙酰基-2-羟基-4-氧代-戊酸乙酯;
2-乙酰基-3-羟基-琥珀酸二乙酯;
2-苯甲酰基-3-羟基-琥珀酸二乙酯;
2-乙酰基-3-羟基-琥珀酸4-乙酯1-(2-甲氧基-乙基)酯;
3-苯甲酰基-2-乙氧基-4-氧代-戊酸乙酯;
2-丁酰基-3-乙氧基-琥珀酸二乙酯;和
2-苯甲酰基-3-乙氧基-琥珀酸二乙酯。
在本发明进-步的方面中,提供式1b化合物:
其中
X和Y具有以上给出的相同含义,
A选自正庚基,-COOC2H5和-CH2-CH(CH)3-(CH2)2-CH=CH(CH3)2;
B是氢;
和虚线与碳-碳键一起代表双键;
条件是
若X=Y是甲基或甲氧基,则A不是-COOC2H5;
若X=Y是甲基,甲氧基或乙氧基,则A不是正庚基;
若X是甲基和Y是乙氧基,则A不是正庚基。
特别的实施方案中是选自下述的式1b化合物:
2-苯甲酰基-癸-2-烯酸乙酯;
2-乙酰基-5,9-二甲基-癸-2,8-二烯酸乙酯;
2-乙酰基-癸-2-烯酸2-(2-甲氧基-乙氧基)-乙酯;
1-(4-叔丁基-苯基)-3-(4-甲氧基-苯基)-2-亚辛基-丙烷-1,3-二酮;
2-亚辛基-丙二酸二苄酯;
2-氨基甲酰基-癸-2-烯酸甲酯;
2-丁酰基-丁-2-烯二酸二乙酯;
2-乙酰基-丁-2-烯二酸1-苄酯4-乙酯;
2-乙酰基-丁-2-烯二酸4-乙酯1-(2-甲氧基-乙基)酯;
3-氨基甲酰基-4-氧代-戊-2-烯酸乙酯;
2-(2,2-二甲基-丙酰基)-丁-2-烯二酸4-乙酯1-甲酯;
2-戊-4-炔酰基-丁-2-烯二酸4-乙酯1-甲酯;
4-乙基1-(2-(三甲基甲硅烷基)乙基)-2-乙酰基马来酸酯;
乙基-4-环己基-4-氧代-3-乙酰基-丁-2-烯酸酯;
乙基3-((三甲基甲硅烷基)甲基氨基甲酰基)-4-氧代戊-2-烯酸酯;
乙基-4-(4-甲基环己基)-4-氧代-3-乙酰基-丁-2-烯酸酯;和1-(2-(二甲基氨基)乙基)4-乙基2-乙酰基马来酸酯。
正如方案1所示,通过式d的醛与式e的二羰基化合物缩合(称为Knoevenagel缩合),可制备其中虚线与碳-碳键一起代表双键,A代表-CR9R10R11和B是氢的式1化合物。可优选在小量(典型地0.1-5mol%)环胺,例如哌啶或吡咯烷存在下进行缩合。
方案1:
可在路易斯酸,例如TiCl4存在下,通过式R9R10R11C-C(O)-CR12R13R14的酮与式e的二羰基化合物缩合,从而制备其中虚线与碳-碳键一起代表双键,A代表-CR9R10R11和B代表-CR12R13R14的式1化合物,正例如Tetrahedron 1973,29,635-638(W.Lehnert)中所述。
类似地,可在路易斯酸,例如TiCl4存在下,通过式R7OOC-C(O)-CR12R13R14的酮酯或式R8(O)C-C(O)-CR12R13R14的α-二酮与式e的二羰基化合物缩合,从而制备其中虚线与碳-碳键一起代表双键,A代表-COOR7或-C(O)R8和B代表-CR12R13R14的式1化合物,正例如Tetrahedron 1972,28,663-666(W.Lehnert)中所述。
可借助优选在小量(典型地0.1-5mol%)环胺,例如哌啶或吡咯烷存在下进行的式e的二羰基化合物加成到式d′的乙醛酸酯上,从而制备其中虚线与碳-碳键一起代表单键,A代表-COOR7和B是-OH的式1化合物,正如方案2所示。
方案2:
类似地,正如方案3所示,可借助优选在小量(典型地0.1-5mol%)环胺,例如哌啶或吡咯烷存在下进行的式e的二羰基化合物加成到式R8(O)C-CHO的烷基乙二醛上,从而制备其中虚线与碳-碳键一起代表单键,A代表-C(O)R8和B是-OH的式1化合物。
方案3:
可由式d′e的化合物为起始,通过使用与水形成共沸物的有机溶剂,例如甲苯或环己烷,在酸性催化剂(典型地0.1-5mol%)对甲苯磺酸存在下共沸除水,从而制备其中虚线与碳-碳键一起代表双键,A代表-COOR7和B是H的式1化合物,正如方案4所示。
方案4:
可在相同的反应容器内连续地进行在方案2中所示的加成步骤和在方案3中所示的脱水步骤。在此情况下,脱水步骤所添加的酸性催化剂的摩尔量必需超过催化加成步骤的环胺量至少0.1mol%。
以与制备d′e′类型的化合物类似的方式制备其中虚线与碳-碳键一起代表双键,A代表-C(O)R8和B是氢的式1化合物。
正如方案5所示,优选在50-150℃的温度下,通过HOR15与d′e′类型的化合物反应,从而制备其中虚线与碳-碳键一起代表单键,A代表-COOR7和B代表-OR15的式1化合物。它们也可通过使d′e′类型的化合物与HOR15直接反应来制备。这一反应优选在加成步骤完成之后,在与得到d′e的反应相同的反应容器内,通过简单地添加过量HOR15,并加热所得溶液到50-150℃下来进行。
方案5:
以类似于制备d′e″类型的化合物所述的工序,通过HNR16R17反应来制备其中B是-NR16R17的式1化合物。
可通过在碱,例如甲醇钠存在下,使式e的二羰基化合物与甲酸乙酯或甲酸甲酯反应,接着用式ClC(O)R18的酰氯酰化,从而制备其中虚线与碳-碳键一起代表双键,A是H和B代表-OH或-OC(O)R18的式1化合物,正如方案6所示。
方案6:
类似地,可通过使用ClC(O)OC2H5,根据ef类型的化合物的制备工序,从而制备其中虚线与碳-碳键一起代表双键,A是-CR9R10R11和B代表-OH或-OC(O)R18的式1化合物。
参考下述非限制性实施例,进一步描述本发明。
这些实施例仅仅是为了阐述的目的,且要理解为本领域的技术人员可在没有脱离本发明范围的情况下作出各种变化和改性。应当理解,所述的实施方案不仅在替代方案内,而且可结合。
实施例1:2-苯甲酰基-癸-2-烯酸乙酯
在5℃下,将哌啶(0.10ml,0.5mol%)加入到辛醛(25.6g,0.20mol)和苯甲酰基乙酸乙酯(38.4g,0.20mol)的混合物中。将所得溶液温热到室温并搅拌24小时,在此期间形成微乳液。用甲基叔丁基醚稀释该混合物,并用2N HCl水溶液,水和盐水洗涤有机层,然后在MgSO4上干燥。
真空除去溶剂,并蒸馏该残渣,以E/Z混合物形式得到在129-135℃/0.1mbar下沸腾的18.0g(38%)产物。该化合物是无色油状物。
13C-NMR(CHCl3,100MHz;主异构体):194.5(s),164.6(s),148.6(d),137.2(s),133.7(d),133.6(s),129.0(d),128.8(d),61.0(t),1.6(t),29.5(t),29.1(t),28.8(t),28.3(t),22.5(t),14.(q),13.9(q)。
MS(EI,70eV):302(<1,M+),257(2),217(10),199(15),186(15),171(4),157(13),105(100)。
实施例2-7
遵照实施例1的通用工序,制备下述化合物,其中所有这些化合物是无色油状物(除非另有说明)且基本上无臭:
(*)通过色谱纯化
(**)所得产物含有约15%的2-(1-羟基-亚乙基)-癸-3-烯酸2-(2-甲氧基-乙氧基)-乙酯。如下所述制备起始材料:3-氧代-丁酸2-(2-甲氧基-乙氧基)-乙酯:
将乙酰乙酸乙酯(39.0g,0.30mol)和二甘醇单甲醚(36.0g,0.30mol)加热到110℃(油浴温度)并添加原钛酸四异丙酯(0.60ml,2.0mmol,0.7mol%)。进一步升高温度到150℃。30分钟之后,蒸馏掉甲醇(5g)并收集。维持温度另外8小时,同时降低装置内的压力到800mbar。在冷却到室温之后,在65-120℃/0.06mbar下蒸馏残渣,分离30.5g含有约10%二甘醇单甲醚的产物(产率44%)。
13C-NMR(CHCl3,100MHz):200.4(s),167.0(s),89.9(d),71.8(t),70.4(t),68.8(t),64.2(t),59.0(q),50.0(t),30.0(q)。
MS(EI,70eV):302(<1,M+),257(2),217(10),199(15),186(15),171(4),157(13),105(100)。
实施例8:2-乙酰基-3-羟基-琥珀酸4-乙酯1-(2-甲氧基-乙基)酯
将乙醛酸乙酯(50%在甲苯中,40.84g,0.20mol)和2-甲氧基乙酰乙酸酯的混合物冷却到5℃并用哌啶(0.10ml,1.0mmol,0.5mol%)处理。缓慢温热该混合物到室温并搅拌1小时。然后用甲基叔丁基醚稀释,并用2N HCl水溶液和盐水稀释。在MgSO4上干燥之后,真空除去溶剂,并通过在硅胶上的快速色谱法纯化残渣,以无色和无味油状物形式得到17.41g 2-乙酰基-3-羟基-琥珀酸4-乙酯1-(2-甲氧基-乙基)酯(33%产率)。该产物由2种非对映异构体的混合物组成。
13C-NMR(CHCl3,100MHz,2种非对映异构体):201.7,201.0(s),171.8,171.8(s),167.6,167.5(s),70.0,69.9(t),69.7,69.2(d),64.5,64.4(t),62.1,62.1(t),61.8,61.7(d),58.8,58.8(q),29.9,29.8(q),13.9,13.9(q)。
MS(EI,70eV):263(<1,[M+1]+),245(<1),219(6),189(36),147(45),85(39),71(43),58(65),43(100)。
实施例9-14:
遵照实施例8的通用工序,制备下述化合物,其中所有这些化合物无色和基本上无味:
实施例16:2-丁酰基-丁-2-烯二酸二乙酯
在Dean-Stark装置内,在3小时内,加热回流2-丁酰基-3-羟基-琥珀酸二乙酯(10.0g,38.5mmol)和对甲苯磺酸(0.20g)在环己烷内的溶液。冷却该溶液到室温,并用环己烷稀释,和用水,稀释的NaHCO3水溶液和盐水洗涤。在MgSO4上干燥有机层,并真空浓缩。在190-200℃的烘箱温度下,在0.1mbar下,bulb-to-bulb蒸馏残渣,以无色,基本上无味的油状物形式得到产物(7.20g,77%产率)。
13C-NMR(CHCl3,100MHz):202.2(s),195.9(s),165.5(s),1164.1(s),164.0(s),162.9(s),147.2(s),144.5(s),128.4(d),127.7(d),62.3(t),62.0(t),61.7(t),61.7(t),44.6(t),41.2(t),16.9(t),16.3(t),14.0(q),13.9(q),13.9(q),13.5(q),13.5(q)。
MS(EI,70eV):197(11,[M-OEt]+),169(28),143(100),125(29),71(37)。
实施例17-22:
遵照实施例16的通用工序,制备下述化合物,其中所有这些化合物是无色油状物且基本上无味:
实施例23:2-乙酰基-3-甲氧基-琥珀酸二乙酯
加热回流根据实施例14所述的工序制备的3-乙酰基-4-氧代-戊-2-烯酸乙酯(3.0g,16.3mmol)在乙醇(20ml)内的溶液20小时。真空除去溶剂并通过在硅胶上的柱色谱纯化残渣。以无色,基本上无味的油状物形式分离产物(2.35g,63%产率)。
13C-NMR(CHCl3,100MHz;主异构体):201.2(s),200.4(s),170.4(s),108.7(S,烯醇形式),77.5(d),69.9(d),67.3(t),61.5(t),30.6(q),29.8(q),23.8(q),15.1(q),15.0(q),14.1(q),14.0(q)。
MS(EI,70eV):197(11,[M-OEt]+),169(28),143(100),125(29),71(37)。
实施例24-27:
遵照实施例23的通用工序,制备下述化合物,其中所有这些化合物是无色的油状物且基本上无味:
实施例29:中和丙硫醇
向23×75mm的顶空小瓶中引入0.25ml 4mM试验化合物在二甲亚砜/H2O1∶1内的溶液。每3个试样制备含有0.25ml二甲亚砜/H2O 1∶1的一个空白样品。用含有橡胶隔膜的20mm铝封口密封小瓶。在15分钟的时间间隔处(这是1GC-分析试验的时间),借助套管向每一样品中添加0.25ml 4mM在二甲亚砜/H2O 1∶1内的丙硫醇溶液。
在室温下静置样品3小时,然后使用与GC-MS装置相连的顶空自动取样器,进行顶空分析。每一样品注射250μl顶空(headspace)。比较丙硫醇的峰面积(MS-离子电流)与空白样品的平均值,计算顶空浓度的下降。下表1中列出了结果。
表1:顶空下降
实施例30:中和在含水环境内的人汗液
如图1所述,制备两个腔室(chamber)样品。它由实施例26所述的顶空小瓶(1′)作为外部容器(containment)和标准HPLC-自动取样器小瓶(2′)作为内部容器组成。在粘胶丝过滤器(3′)上吸收试验化合物(5.0μmol)(以CH2Cl2溶液形式施加并使之蒸发)。在内部小瓶(2′)的底部放置用量为100μl的3-甲基己酸(23mM)和3-巯基-1-丁醇(17mM)的水溶液。在置于顶空小瓶(1′)内的HPLC-小瓶(2′)上紧密地旋紧含过滤器(3′)的螺帽。用含有橡胶隔膜(5′)的铝封口密闭顶空小瓶。在内部小瓶内如上所述地制备含有倒空过滤器(3′)和3-甲基己酸与3-巯基-1-丁醇的水溶液(每3个试样一个空白)。在35℃下静置样品16小时,然后如实施例26所述进行顶空分析。
恶臭化合物(3-甲基己酸和3-巯基-1-丁醇)经过滤器扩散到外部体积(6′)内。因此,与空白样品相比,施加在过滤器(3′)上的式1化合物(中和物质)将降低外部体积内汗液恶臭剂的顶空浓度。表2列出了对于本发明的数种化合物来说观察到的顶空下降。
表2:恶臭化合物的顶空下降%
实施例31:对汗液恶臭还原(reconstitution)的感官评价
在1×1cm的棉花样本上施加腋部恶臭还原的乙醇溶液(100μl,0.1%wt/wt),然后将50μl试验化合物(1%乙醇溶液)供料到恶臭处理过的样本上。在LMS(标记的数字刻度)上由20个评定人的专家小组评定恶臭强度。然后在没有添加试验化合物的情况下,相对于样本的恶臭的下降来表达结果。表3中示出了结果。
表3:专门小组试验中腋部恶臭强度的下降
实验表明,在降低腋部恶臭方面,大多数化合物感觉比富马酸二己酯(DHF)更加有效或者至少类似地有效。
实施例32:
也可根据实施例1的通用工序制备本发明的下述化合物:
实施例33:
也可根据实施例8的通用工序制备本发明的下述化合物:
实施例34:
也可根据实施例15的通用工序制备本发明的下述化合物:
Claims (20)
1.式1化合物作为恶臭中和剂的用途:
其中
X和Y独立地为选自下述的残基:
-CR1R2R3,其中
R1,R2和R3独立地为H,烃残基,或含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
-NR4R5,其中
R4和R5独立地为H,烃残基;或者
R4和R5与它们连接到其上的氮原子一起形成3,5或6-元环;或者R4和R5是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
和
-OR6,其中
R6是烃残基;或者
R6是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
A是H;-COOR7,其中
R7是烃残基;或者
R7是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
-C(O)R8,其中
R8是烃残基;或者
R8是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
或者
-CR9R10R11,其中
R9,R10和R11独立地为H,烃残基,或含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
B是H;-CR12R13R14,其中
R12,R13和R14独立地为H,或烃残基;或者
R12,R13和R14独立地为含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
或者
-OC(O)R18,其中
R18是H,或烃残基;
和虚线与碳-碳键一起代表双键;
或者
B是-NR16R17,其中
R16和R17独立地为H,或烃残基;或者
R16和R17独立地为含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;或者
-OR15,其中
R15是H,或烃残基;或者
R15是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
和虚线与碳-碳键一起代表双键或单键;
条件是A和B不同时为氢。
2.权利要求1的式1化合物的用途,其中X是式-CR1R2R3的残基,其中R1,R2和R3与它们连接到其上的碳原子一起形成选自下述的残基:
C1-C20烷基;
含有选自0,N,Si,Cl和Br中的至少一个杂原子的C1-C20烷基;
C3-C8环烷基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C3-C8环烷基;
C6-C12烷基环烷基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C6-C12烷基环烷基;
C6-C12环烷基烷基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C6-C12环烷基烷基;
C2-C10烯基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C2-C10烯基;
C2-C10炔基;
含有从形成羟基,羰基,醚或酯基的O,N,Si,Cl和Br组成的组中选择的至少一个杂原子的C2-C10炔基;
C6-C10芳基;
被选自C1-C15烷基和C1-C15烷氧基中的至少一个取代基取代的C6-C10芳基;
C5-C10杂芳基;
C7-C10烷芳基;和
被选自C1-C15烷基,C1-C15烷氧基,氨基,C1-C15烷基氨基和C2-C30二烷基氨基中的至少一个取代基取代的C7-C10烷芳基。
3.权利要求1或2的式1化合物的用途,其中A选自H,C1-C9烷基,-COOC2H5,-C(O)CH3和-COOCH2Ph。
4.权利要求1或2的式1化合物的用途,其中
A是-CR9R10R11,其中R9,R10和R11与它们连接到其上的碳原子一起形成被选自羟基,C1-C5烷氧基,乙酰基和氨基中的至少一个取代基取代的C6-C10芳基;或者
A是-CR9R10R11,其中R9,R10和R11与它们连接到其上的碳原子一起形成C5-C8杂芳基。
5.权利要求1的式1化合物的用途,其中A是-CR9R10R11,其中R9,R10和R11与它们连接的其上的碳原子一起形成吡啶基。
6.前述任何一项权利要求的式1化合物的用途,其中B是H,羟基,-O-C2H5,-O-(CH2)2-O-(CH2)2-O-C2H5,-O-C(O)CH3或者-O-C(O)C2H5。
7.权利要求1的式1化合物的用途,所述化合物选自
2-(3,7-二甲基-辛-2,6-二亚烯基)-丙二酸二乙酯;
3-亚辛基-戊烷-2,4-二酮;
2-吡啶-2-基亚甲基-丙二酸二乙酯;
2-亚辛基-丙二酸二甲酯;
2-乙氧羰基-丁-2-烯二酸二乙酯;
2-乙酰基-戊-2-烯酸乙酯;
2-亚辛基-丙二酸二乙酯;
2-亚癸基-丙二酸二乙酯;
2-乙酰基-癸-2-烯酸乙酯;
2-(2-羟基-亚苄基)-1-苯基-丁烷-1,3-酮;
2-(2-羟基-亚苄基)-丙二酸二乙酯;
3-(2-羟基-亚苄基)-戊烷-2,4-二酮;
3-(2-羟基-4-甲氧基-亚苄基)-戊烷-2,4-二酮;
2-(2-羟基-亚苄基)-3-氧代-丁酸乙酯;
2-乙氧羰基氧基亚甲基-丙二酸二乙酯;
2-乙酰氧基亚甲基-丙二酸二乙酯;
2-苯甲酰基-癸-2-烯酸乙酯;
2-乙酰基-5,9-二甲基-癸-2,8-二烯酸乙酯;
2-乙酰基-癸-2-烯酸2-(2-甲氧基-乙氧基)-乙酯;
1-(4-叔丁基-苯基)-3-(4-甲氧基-苯基)-2-亚辛基-丙烷-1,3-二酮;
2-亚辛基-丙二酸二苄酯;
2-氨基甲酰基-癸-2-烯酸甲酯;
3-(3-乙氧基-4-羟基-亚苄基)-戊烷-2,4-二酮;
2-乙酰基-3-羟基-琥珀酸4-乙酯1-(2-甲氧基-乙基)酯;
3-乙酰基-2-羟基-4-氧代-戊酸乙酯;
2-乙酰基-3-羟基-琥珀酸二乙酯;
2-苯甲酰基-3-羟基-琥珀酸二乙酯;
2-丁酰基-3-羟基-琥珀酸二乙酯;
2-乙酰基-3-羟基-琥珀酸1-叔丁基酯4-乙酯;
2-(2,2-二甲基-丙酰基)-3-羟基-琥珀酸4-乙酯1-甲酯;
2-乙酰基-3-羟基-琥珀酸4-乙酯1-(2-甲氧基-乙基)酯;
2-丁酰基-丁-2-烯二酸二乙酯;
2-乙酰基-丁-2-烯二酸1-苄酯4-乙酯;
2-乙酰基-丁-2-烯二酸4-乙酯1-(2-甲氧基-乙基)酯;
3-氨基甲酰基-4-氧代-戊-2-烯酸乙酯;
2-(2,2-二甲基-丙酰基)-丁-2-烯二酸4-乙酯1-甲酯;
2-戊-4-炔酰基-丁-2-烯二酸4-乙酯1-甲酯;
2-乙酰基-3-甲氧基-琥珀酸二乙酯;
3-苯甲酰基-2-乙氧基-4-氧代-戊酸乙酯;
2-丁酰基-3-乙氧基-琥珀酸二乙酯;
2-苯甲酰基-3-乙氧基-琥珀酸二乙酯;
2-乙酰基-3-[2-(2-乙氧基-乙氧基)-乙氧基]-琥珀酸二乙酯;
3-乙酰基-2-乙氧基-4-氧代-戊酸乙酯;
2-亚丙基-1-(吡啶-4-基)丁烷-1,3-二酮;
2-亚乙基-1-(1H-咪唑-5-基)丁烷-1,3-二酮;
3-(2-羟基-5-硝基亚苄基)戊烷-2,4-二酮;
3-(2-羟基-5-乙酰基亚苄基)戊烷-2,4-二酮;
乙基-2-羟基-4-(1H-咪唑-4-基)-3-乙酰基-4-氧代丁酸酯;
4-乙基1-(2-(三甲基甲硅烷基)乙基)-2-乙酰基马来酸酯;
乙基-4-环己基-4-氧代-3-乙酰基-丁-2-烯酸酯;
乙基3-((三甲基甲硅烷基)甲基氨基甲酰基)-4-氧代戊-2-烯酸酯;
乙基-4-(4-甲基环己基)-4-氧代-3-乙酰基-丁-2-烯酸酯;
1-(2-(二甲基氨基)乙基)4-乙基2-乙酰基马来酸酯;
苄基3-乙酰基-4-氧代戊-2-烯酸酯;和
4-乙酰基-9-甲基癸-3,8-二烯-2,5-二酮。
8.一种消费产品,它包括前述任何一项权利要求中定义的式1化合物作为恶臭中和剂。
9.权利要求8的消费产品,其中该消费产品选自化妆品,家庭护理产品和织物护理产品。
10.权利要求8或7的消费产品,它包括约0.01-约20wt%的权利要求1-7任何一项中定义的式1化合物或其混合物。
11.赋予基底恶臭中和效果的方法,该方法包括使基底与权利要求8-10任何一项中定义的消费产品接触。
12.权利要求11的方法,其中基底选自织物,硬表面,皮肤和毛发。
13.将消费产品分散到空间内的方法,该方法包括:
(a)将式1化合物掺入到消费产品内;和
(b)将有效量的消费产品分散到空间内。
14.权利要求13的方法,其中消费产品选自家庭护理产品。
15.式1a化合物
其中
X和Y独立地为选自下述的残基:
-CR1R2R3,其中
R1,R2和R3独立地为H,烃残基,或含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
-NR4R5,其中
R4和R5独立地为H,烃残基;或者
R4和R5与它们连接到其上的氮原子一起形成3,5或6-元环;或者R4和R5是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
和
-OR6,其中
R6是烃残基;或者
R6是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
A是-COOR7,其中
R7是烃残基;或者
R7是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;或者
A是-C(O)R8,其中
R8是烃残基;或者
R8是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
B是-NR16R17,其中
R16和R17独立地为H,或烃残基;或者
R16和R17独立地为含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;或者
B是-OR15,其中
R15是H,或烃残基;或者
R15是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
和虚线与碳-碳键一起代表单键;
条件是
若X=Y是乙氧基,则B不是甲氧基;和
若X是乙氧基和Y是甲基,则B不是甲氧基或乙氧基。
16.权利要求15的化合物,其中A是-COOC2H5。
17.权利要求15或16的化合物,其中B是羟基或-O-C2H5。
18.权利要求15的化合物,所述化合物选自
3-乙酰基-2-羟基-4-氧代-戊酸乙酯;
2-乙酰基-3-羟基-琥珀酸二乙酯;
2-苯甲酰基-3-羟基-琥珀酸二乙酯;
2-乙酰基-3-羟基-琥珀酸4-乙酯1-(2-甲氧基-乙基)酯;
3-苯甲酰基-2-乙氧基-4-氧代-戊酸乙酯;
2-丁酰基-3-乙氧基-琥珀酸二乙酯;和
2-苯甲酰基-3-乙氧基-琥珀酸二乙酯。
19.式1b化合物
其中
X和Y独立地为选自下述的残基:
-CR1R2R3,其中
R1,R2和R3独立地为H,烃残基,或含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
-NR4R5,其中
R4和R5独立地为H,烃残基;或者
R4和R5与它们连接到其上的氮原子一起形成3,5或6-元环;或者R4和R5是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
和
-OR6,其中
R6是烃残基;或者
R6是含有从形成羟基,羰基,醚或酯基的氧,氮,硅,氯和溴组成的组中选择的至少一个杂原子的烃残基;
A选自正庚基,-COOC2H5和-CH2-CH(CH)3-(CH2)2-CH=CH(CH3)2;
B是氢;
和虚线与碳-碳键一起代表双键;
条件是
若X=Y是甲基或甲氧基,则A不是-COOC2H5;
若X=Y是甲基,甲氧基或乙氧基,则A不是正庚基;
若X是甲基和Y是乙氧基,则A不是正庚基。
20.权利要求19的化合物,所述化合物选自:
2-苯甲酰基-癸-2-烯酸乙酯;
2-乙酰基-5,9-二甲基-癸-2,8-二烯酸乙酯;
2-乙酰基-癸-2-烯酸2-(2-甲氧基-乙氧基)-乙酯;
1-(4-叔丁基-苯基)-3-(4-甲氧基-苯基)-2-亚辛基-丙烷-1,3-二酮;
2-亚辛基-丙二酸二苄酯;
2-氨基甲酰基-癸-2-烯酸甲酯;
2-丁酰基-丁-2-烯二酸二乙酯;
2-乙酰基-丁-2-烯二酸1-苄酯4-乙酯;
2-乙酰基-丁-2-烯二酸4-乙酯1-(2-甲氧基-乙基)酯;
3-氨基甲酰基-4-氧代-戊-2-烯酸乙酯;
2-(2,2-二甲基-丙酰基)-丁-2-烯二酸4-乙酯1-甲酯;
2-戊-4-炔酰基-丁-2-烯二酸4-乙酯1-甲酯;
4-乙基1-(2-(三甲基甲硅烷基)乙基)-2-乙酰基马来酸酯;
乙基-4-环己基-4-氧代-3-乙酰基-丁-2-烯酸酯;
乙基3-((三甲基甲硅烷基)甲基氨基甲酰基)-4-氧代戊-2-烯酸酯;
乙基-4-(4-甲基环己基)-4-氧代-3-乙酰基-丁-2-烯酸酯;和
1-(2-(二甲基氨基)乙基)4-乙基2-乙酰基马来酸酯。
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GBGB0501237.2A GB0501237D0 (en) | 2005-01-21 | 2005-01-21 | Organic compounds |
GB0501237.2 | 2005-01-21 |
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US (1) | US20080305066A1 (zh) |
EP (1) | EP1838278A1 (zh) |
JP (1) | JP2008528451A (zh) |
KR (1) | KR20070097073A (zh) |
CN (1) | CN101106968A (zh) |
BR (1) | BRPI0614023A2 (zh) |
GB (1) | GB0501237D0 (zh) |
MX (1) | MX2007008551A (zh) |
WO (1) | WO2006076821A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101472874B (zh) * | 2006-06-15 | 2012-11-14 | 奇华顿股份有限公司 | 香料化合物 |
CN103415498A (zh) * | 2010-12-06 | 2013-11-27 | 赛泽恩有限公司 | 苯亚甲基取代的2,4-戊二酮化合物和其作为稳定剂的应用 |
Families Citing this family (10)
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EP2272491A1 (fr) * | 2009-06-18 | 2011-01-12 | Robertet S.A. | Nouvelles compositions désodorisantes et produits désodorisants les renfermant |
US8617528B2 (en) | 2010-12-06 | 2013-12-31 | Sytheon Ltd. | Compositions and methods for stabilizing ingredients using 2,4-pentanedione compounds |
US9126890B2 (en) * | 2011-10-20 | 2015-09-08 | International Flavors & Fragrances Inc. | Low volatile reactive malodor counteractives and methods of use thereof |
US20120294821A1 (en) * | 2011-05-20 | 2012-11-22 | International Flavors & Fragrances Inc. | Low Volatile Reactive Malodor Counteractives and Methods of Use Thereof |
US10226544B2 (en) | 2015-06-05 | 2019-03-12 | International Flavors & Fragrances Inc. | Malodor counteracting compositions |
US10549003B2 (en) * | 2016-05-31 | 2020-02-04 | The Procter & Gamble Company | Method of demonstrating efficacy of a malodor counteractant product |
MX2021011240A (es) | 2019-03-20 | 2021-10-22 | Firmenich & Cie | Compuestos de properfume encapsulados. |
JP2022539003A (ja) | 2019-06-27 | 2022-09-07 | フイルメニツヒ ソシエテ アノニム | 賦香された消費者製品 |
EP4039244A1 (en) | 2021-02-04 | 2022-08-10 | Givaudan SA | Improvements in or relating to organic compounds |
WO2023247298A1 (en) * | 2022-06-21 | 2023-12-28 | Firmenich Sa | Compositions for preventing, reducing, or ameliorating malodorous aldehydes and ketones, and uses thereof |
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AU5677773A (en) * | 1972-07-14 | 1974-12-12 | Princeton Biomedix, Incorporated | Pharmaceutically useful compounds and methods of producing and using same |
ATE35810T1 (de) * | 1984-04-06 | 1988-08-15 | Zambon Spa | Verfahren zur herstellung von optisch aktiven alpha-arylalkansaeuren und ihre zwischenprodukte. |
US4810819A (en) * | 1984-04-06 | 1989-03-07 | Zambon Spa | Process for the preparation of optically active alpha-acrylalkanoic acids and novel intermediates thereof |
DE3423249A1 (de) * | 1984-06-23 | 1986-01-02 | Hüls AG, 4370 Marl | Verfahren zur herstellung von alkyliden- und arylidenverbindungen |
US4830787A (en) * | 1987-08-13 | 1989-05-16 | Nabisco Brands, Inc. | Low calorie fat mimetics comprising carboxy/carboxylate esters |
JPH04202122A (ja) * | 1990-11-28 | 1992-07-22 | Procter & Gamble Co:The | ジケトン脱臭組成物及び脱臭方法 |
SG91244A1 (en) * | 1996-06-24 | 2002-09-17 | Givaudan Roure Int | Malodour preventing agents |
JP2000502746A (ja) * | 1996-08-19 | 2000-03-07 | ザ、プロクター、エンド、ギャンブル、カンパニー | β―ケトエステルプロフレグランスを含んだ洗濯洗剤組成物 |
GB0320441D0 (en) * | 2003-09-02 | 2003-10-01 | Givaudan Sa | Organic compounds |
-
2005
- 2005-01-21 GB GBGB0501237.2A patent/GB0501237D0/en not_active Ceased
-
2006
- 2006-01-06 JP JP2007551527A patent/JP2008528451A/ja active Pending
- 2006-01-06 CN CNA2006800028602A patent/CN101106968A/zh active Pending
- 2006-01-06 EP EP06700027A patent/EP1838278A1/en not_active Withdrawn
- 2006-01-06 BR BRPI0614023-8A patent/BRPI0614023A2/pt not_active IP Right Cessation
- 2006-01-06 US US11/814,057 patent/US20080305066A1/en not_active Abandoned
- 2006-01-06 KR KR1020077016600A patent/KR20070097073A/ko not_active Application Discontinuation
- 2006-01-06 MX MX2007008551A patent/MX2007008551A/es not_active Application Discontinuation
- 2006-01-06 WO PCT/CH2006/000010 patent/WO2006076821A1/en active Application Filing
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN101472874B (zh) * | 2006-06-15 | 2012-11-14 | 奇华顿股份有限公司 | 香料化合物 |
CN103415498A (zh) * | 2010-12-06 | 2013-11-27 | 赛泽恩有限公司 | 苯亚甲基取代的2,4-戊二酮化合物和其作为稳定剂的应用 |
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JP2008528451A (ja) | 2008-07-31 |
MX2007008551A (es) | 2007-08-14 |
WO2006076821A1 (en) | 2006-07-27 |
GB0501237D0 (en) | 2005-03-02 |
US20080305066A1 (en) | 2008-12-11 |
EP1838278A1 (en) | 2007-10-03 |
BRPI0614023A2 (pt) | 2011-03-01 |
KR20070097073A (ko) | 2007-10-02 |
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