CN112352037B - 在α位具有甲酰氧基的异丁酸酯化合物、香料组合物及作为香料的用途 - Google Patents
在α位具有甲酰氧基的异丁酸酯化合物、香料组合物及作为香料的用途 Download PDFInfo
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- CN112352037B CN112352037B CN201980042401.4A CN201980042401A CN112352037B CN 112352037 B CN112352037 B CN 112352037B CN 201980042401 A CN201980042401 A CN 201980042401A CN 112352037 B CN112352037 B CN 112352037B
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- -1 Isobutyrate compound Chemical class 0.000 title description 68
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- 235000019634 flavors Nutrition 0.000 claims description 13
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 11
- 239000004480 active ingredient Substances 0.000 abstract description 10
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
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- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
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Abstract
本发明涉及一种香料组合物,含有式(1)所示的化合物作为有效成分。(式(1)中,R1表示碳原子数1~6的直链状、支链状或环状的烷基。)
Description
技术领域
本发明涉及在α位具有甲酰氧基的异丁酸酯化合物、香料组合物和作为香料的用途。
背景技术
报道了异丁酸酯、在α位具有与氧的键合的异丁酸酯作为香料是有用的,例如在专利文献1公开了作为在α位具有与氧的键合的异丁酸酯,α-烷氧基异丁酸的直链或支链的碳原子数4~12的烷基酯作为香料是有用的,α-乙氧基异丁酸正己酯具有类似薰衣草的香气。
另一方面,在专利文献2中公开了作为在α位具有甲酰氧基的异丁酸酯,甲酯及乙酯作为锂电池用非水电解液的添加成分是有用的,但没有记载其香气特性、包含其的香料组合物、进而作为香料的用途的方法。
现有技术文献
专利文献
专利文献1:美国专利第3368943号说明书
专利文献2:国际公开第2009/113545号
发明内容
本发明所要解决的课题是提供一种在作为香料和调合香料原材料有用的在α位具有甲酰氧基的异丁酸酯化合物。另外,本发明所要解决的其它的课题在于提供一种含有在α位具有甲酰氧基的异丁酸酯化合物作为有效成分的香料组合物及该化合物的作为香料的用途。
本发明人等在合成各种化合物并对其香气反复深入研究之后,其结果发现在α位具有甲酰氧基的异丁酸的特定的酯化合物作为香料和调合香料原材料是有用的。
即,本发明如下所示。
<1>一种香料组合物,含有式(1)所示的化合物作为有效成分。
(式(1)中,R1表示碳原子数1~6的直链状、支链状或环状的烷基。)
<2>根据<1>所示的香料组合物,式(1)中,R1选自甲基、乙基、正丙基、异丙基、正丁基、异丁基及环戊基。
<3>式(1)所示的化合物的作为香料的用途。
(式(1)中,R1表示碳原子数1~6的直链状、支链状或环状的烷基。)
<4>根据<3>所述的用途,其中,式(1)中,R1选自甲基、乙基、正丙基、异丙基、正丁基、异丁基和环戊基。
<5>根据<3>或<4>所述的用途,其中,式(1)所述的化合物赋予类似薄荷或类似水果的香味。
<6>根据<3>或<4>所述的用途,其中,式(1)中,R1为甲基的化合物赋予类似二氢大马酮的果香调、花香调或木质调的香味。
<7>一种化合物,由式(2)所示。
(式(2)中,R2表示碳原子数3~6的直链状、支链状或环状的烷基。)
<8>根据<7>所述的化合物,其中,式(2)中,R2选自正丙基、异丙基、正丁基、异丁基和环戊基。
<9>根据<7>或<8>所述的化合物,其中,式(2)中,R2为正丙基。
<10>根据<7>或<8>所述的化合物,其中,式(2)中,R2为异丙基。
<11>根据<7>或<8>所述的化合物,其中,式(2)中,R2为正丁基。
<12>根据<7>或<8>所述的化合物,其中,式(2)中,R2为异丁基。
<13>根据<7>或<8>所述的化合物,其中,式(2)中,R2为环戊基。
根据本发明,可以提供一种作为香料和调合香料原材料有用的在α位具有甲酰氧基的异丁酸酯化合物。另外,根据本发明,能够提供含有在α位具有甲酰氧基的异丁酸酯化合物作为有效成分的香料组合物和该化合物的作为香料的用途。
具体实施方式
[香料组合物及用途]
本发明的香料组合物含有下述式(1)所述的化合物作为有效成分。另外,本发明的用途是下述式(1)所示的化合物的作为香料的用途。
以下,对于本发明,详细进行说明。
<式(1)所示的化合物>
本发明的香料组合物和本发明的用途中使用的化合物由下述式(1)所示。
(式(1)中,R1表示碳原子数1~6的直链状、支链状或环状的烷基。)
式(1)中,作为R1,具体而言,可举出甲基、乙基、正丙基、异丙基、正丁基、异丁基(2-甲基丙基)、仲丁基(1-甲基丙基)、叔丁基、正戊基、1-甲基丁基(2-戊基)、2-甲基丁基、3-甲基丁基、新戊基(2,2-二甲基丙基)、2-甲基丁烷-2-基、1-乙基丙基(3-戊基)、3-甲基丁烷-2-基、正己基、1-甲基戊基(2-己基)、2-甲基戊基、3-甲基戊基、4-甲基戊基、2-甲基戊烷-2-基、2,2-二甲基丁基、3,3-二甲基丁基、3-甲基戊烷-2-基、2,3-二甲基丁基、4-甲基戊烷-2-基、3-己基、2-乙基丁基、2,3-二甲基丁烷-2-基、3,3-二甲基丁烷-2-基、4-甲基戊烷3-基、环丙基、环丁基、环戊基、环己基等。
R1基具有手性碳的情况下,式(1)所示的化合物包括由此产生的光学异构体中的任一个或任意比例的混合物。
上述式(1)所示的化合物作为香料和调合香料原材料是有用的,具有类似薄荷或类似水果的香气,在此基础上,根据酯部位的烷基(R1)的不同,还同时示出了花香调、草本调、木质调、辛辣调等香气。
特别优选为R1为甲基。
特别优选为R1为乙基。
特别优选为R1为正丙基。
特别优选为R1为异丙基。
特别优选为R1为正丁基。
特别优选为R1为异丁基。
特别优选为R1为环戊基。
本发明中,作为式(1)所示的化合物,例示了以下的式(1-1)~(1-36)中的任一者所示的化合物,特别优选的化合物是以下的式(1-1)~(1-7)中的任一者所述的化合物。
近年来,有对化学物质的毒性、对环境的影响极重视的倾向,这对于香料、香料组合物也不例外。以对人体的致敏性、对环境的积蓄性等为理由,有以往使用的香料的用途条件被严格限制,或禁止使用的案例增加的倾向。由此,存在下述状况:环境负荷少的香料和香料组合物比以往更强烈地被需求。因此,作为调合香料原材料,也优选生物分解性优异。
式(1)所示的化合物包含生物分解性优异的化合物,从生物分解性的观点考虑,R1优选为选自甲基、乙基、正丙基、异丙基、正丁基、异丁基和环戊基中的基团。
对于式(1)所示的化合物而言,其自身如后所述那样,具有优异的香气,因此作为香料是有用的。另外,香料一般以单品形式使用的情况较少,多数情况是以根据目的配合多个香料而得到的调合香料(香料组合物)的形式使用。式(1)所示的化合物作为配合于调合香料(香料组合物)的香料(也称为“调合香料原材料”)是有用的,本发明的香料组合物含有式(1)所示的化合物作为有效成分。作为香料,可以单独使用1种上述式(1)所示的化合物,也可以并用2种以上。
另外,式(1)所示的化合物在不损害本发明的效果的范围内,不排除包含少量的杂质、副产物、夹杂物等的情况。
式(1)所示的化合物具有类似薄荷或类似水果的香气,并且具有花香调、草本调、木质调、辛辣调等香气,并且扩散性也优异。另外,式(1-1)所示的化合物具有类似二氢大马酮的果香调、花香调或木质调的香气,并且扩散性也优异。
可以通过将式(1)所示的化合物单独作为香料添加用于以各种香味化妆品类、保健卫生材料为代表的医药品、日用杂货品、食品等而赋予香气,另外,也可以将式(1)所示的化合物与其它的调合香料原材料等混合,制备后述的香料组合物(调合香料),将其配合于各种制品而赋予香气。其中,从得到目标香气的观点考虑,将式(1)所示的化合物作为调合香料原材料配合于香料组合物,制备含有式(1)所示的化合物作为有效成分的香料组合物,通过在制品中配合该香料组合物而赋香。
另外,式(1)所示的化合物优选用作香料,更优选用于赋予类似薄荷或类似水果的香味。进而,式(1-1)所示的化合物更优选用于赋予类似二氢大马酮的果香调、花香调或木质调的香味。
<香料组合物>
本发明的香料组合物(调合香料)含有式(1)所示的化合物作为有效成分。应予说明,只要含有式(1)所示的化合物至少1种以上就没有特别限定,也可以含有2种以上的式(1)所示的化合物。
本发明的香料组合物含有式(1)所示的化合物作为有效成分即可,其他的成分没有特别限定,优选进一步含有其它的调合香料原材料(以下,也称为“现有香料”)。
应予说明,“香料组合物(调合香料)”是通过将该香料组合物添加于各种香味化妆品类、医药品、食品、饮料等从而赋予香气的组合物、或是其本身就是用于香水等的组合物,在现有香料的基础上,可以根据需要含有溶剂等添加剂。
式(1)所示的化合物的配合量根据化合物的种类、目标香气的种类和香气的强度等而不同,但作为式(1)所示的化合物的量,在香料组合物中,优选为0.001质量%以上,更优选为0.01质量%以上,更优选为0.1质量%以上,优选为90质量%以下,更优选为70质量%以下,更优选为50质量%以下。
现有香料只要是以往公知的香料成分就没有特别限制,可以使用广泛的范围的香料,例如可以从下述的化合物中单独选择或者以任意的混合比例选择2种以上而使用。
例如柠檬烯、α-蒎烯、β-蒎烯、萜品烯、雪松烯、长叶烯、巴伦西亚桔烯等烃类;芳樟醇、香茅醇、香叶醇、橙花醇、萜品醇、二氢月桂烯醇、乙基芳樟醇、法呢醇、橙花叔醇、顺式-3-己烯醇、雪松醇、薄荷醇、冰片、β-苯基乙基醇、苄基醇、苯基己醇、2,2,6-三甲基环己基-3-己醇、1-(2-叔丁基环己氧基)-2-丁醇、4-异丙基环己烷甲醇、4-叔丁基环己醇、4-甲基-2-(2-甲基丙基)四氢-2H-吡喃-4-醇、2-甲基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇、2-乙基-4-(2,2,3-三甲基-3-环戊烯-1-基)-2-丁烯-1-醇、异莰基环己醇、3,7-二甲基-7-甲氧基辛烷-2-醇等醇类;丁香酚、百里香酚、香兰素等酚类;甲酸芳樟酯、甲酸香茅酯、甲酸香叶酯、乙酸正己酯、乙酸顺式-3-己烯酯、乙酸芳樟酯、乙酸香茅酯、乙酸香叶酯、乙酸橙花酯、乙酸松油酯、乙酸诺卜酯、乙酸冰片酯、乙酸异冰片酯、乙酸邻叔丁基环己酯、乙酸对叔丁基环己酯、乙酸三环癸烯酯、乙酸苄酯、乙酸苏合香酯、乙酸肉桂酯、乙酸二甲基苄基原酯、3-戊基四氢吡喃-4-基乙酸酯、丙酸香茅酯、丙酸三环癸烯酯、丙酸烯丙基环己酯、乙基2-环己基丙酸酯、丙酸苄酯、丁酸香茅酯、正丁酸二甲基苄基原酯、异丁酸三环癸烯酯、2-壬烯酸甲酯、苯甲酸甲酯、苯甲酸苄酯、肉桂酸甲酯、水杨酸甲酯、水杨酸正己酯、水杨酸顺式-3-己烯酯、惕格酸香叶酯、惕格酸顺式-3-己烯酯、茉莉酸甲酯、二氢茉莉酸甲酯、甲基-2,4-二羟基-3,6-二甲基苯甲酸酯、甲基苯基缩水甘油酸乙酯、邻氨基苯甲酸甲酯、果香酯(FRUITATE)等酯类:正辛醛、正癸醛、正十二醛、2-甲基十一醛、10-十一烯醛、香茅醛、柠檬醛、羟基香茅醛、二甲基四氢苯甲醛、4(3)-(4-羟基-4-甲基戊基)-3-环己烯-1-甲醛、2-环己基丙醛、对叔丁基-α-甲基氢肉桂醛、对异丙基-α-甲基氢肉桂醛、对乙基-α,α-二甲基氢肉桂醛、α-戊基肉桂醛、α-己基肉桂醛、胡椒醛、α-甲基-3,4-亚甲基二氧基氢肉桂醛等醛类;甲基庚烯酮、4-亚甲基-3,5,6,6-四甲基-2-庚酮、戊基环戊酮、3-甲基-2-(顺式-2-戊烯-1-基)-2-环戊烯-1-酮、甲基环戊烯酮、玫瑰酮、γ-甲基紫罗酮、α-紫罗酮、香芹酮、薄荷酮、樟脑、香柏酮、苄基丙酮、茴香基丙酮、甲基β-萘酮、2,5-二甲基-4-羟基-3(2H)-呋喃酮、麦芽酚(Maltol)、7-乙酰基-1,2,3,4,5,6,7,8-八氢-1,1,6,7-四甲基萘、麝香酮、灵猫酮、环十五烷酮、环十六烯酮等酮类;乙醛乙基苯基丙基缩醛、柠檬醛二乙基缩醛、苯基乙醛甘油缩醛、乙酰乙酸乙酯乙二醇缩醛类的缩醛类以及缩酮类;茴香脑、β-萘基甲基醚、β-萘基乙基醚、柠檬烯氧化物、玫瑰醚、1,8-桉叶素、外消旋体或光学活性的十二氢-3a,6,6,9a-四甲基萘[2,1-b]呋喃等醚类;香茅腈等腈类;γ-壬内酯、γ-十一内酯、σ-癸内酯、γ-茉莉内酯、香豆素、环十五内酯、环十六内酯、黄葵内酯、十三烷二酸环乙撑酯、11-氧杂十六内酯等内酯类;橙子、柠檬、佛手柑、橘子、胡椒薄荷、留兰香、薰衣草、洋甘菊、迷迭香、桉树、鼠尾草、罗勒、玫瑰、天竺葵、茉莉花、依兰、茴芹、丁香、生姜、肉豆蔻、小豆蔻、雪松、扁柏、檀香木、香根草、广霍香、岩玫瑰等的天然精油、天然提取物;合成香料等其它的香料物质等。
另外,香料组合物也可以包含聚氧乙烯月桂基硫酸醚等表面活性剂;二丙二醇、邻苯二甲酸二乙酯、乙二醇、丙二醇、肉豆蔻酸甲酯、柠檬酸三乙酯等溶剂;抗氧化剂;着色剂等作为调合香料原材料以外的构成成分。
式(1)所示的化合物具有类似薄荷或类似水果的香气,并且具有花香调、草本调、木质调、辛辣调等香气,由此通过与现有香料组合,能够在赋予薄荷调或果香调的同时,赋予自然的花香调、草本调、木质调、辛辣调,因此对于向以各种香味化妆品类、保健卫生材料为代表的医药品、日用杂货品、食品等进行添加并赋予香气而言是有用的。另外,式(1-1)所示的本发明的异丁酸酯具有类似二氢大马酮的果香调、花香调或木质调的香气,由此与现有香料组合等,对赋予香气是有用的。
作为能够添加含有式(1)所示的化合物的香料组合物来用于赋予香气以及用于对配合对象物的香气进行改良的制品,可举出香味化妆品类、健康卫生材料、杂货、饮料、食品、准医药品、医药品等各种制品,例如可作为如下制品的香气成分而使用:香水、古龙水类等芬香制品;洗发水、护发素类、生发液、发膏类、摩丝、啫喱、发蜡、喷雾剂等其它毛发用化妆品;化妆水、美容液、霜、乳液、面膜、粉底、香粉、口红、各种彩妆类等肌肤用化妆品;洗碗用洗剂、洗衣用洗剂、软化剂类、消毒用洗剂类、消臭洗剂类、室内芳香剂、家具保养剂、玻璃清洁剂、家具清洁剂、床清洁剂、消毒剂、杀虫剂、漂白剂、杀菌剂、忌避剂、其他的各种健康卫生用洗剂类;牙膏、鼠标刷洗剂、沐浴剂、止汗制品、烫发液等准医药品;卫生纸、擦手纸等杂货;医药品等;食品等。
上述制品中的香料组合物的配合量没有特别限定,根据待赋香的制品的种类、性质和感官效果等,香料组合物的配合量可以在广范围内进行选择。例如为0.00001质量%以上,优选为0.0001质量%以上,更优选为0.001质量%以上,例如在香水等芬香的情况下可以为100质量%,优选为80质量%以下,更优选为60质量%以下,更进一步优选为40质量%以下。
[式(2)所示的化合物]
本发明的化合物由式(2)所示。以下,也将式(2)所示的化合物称为“本发明的异丁酸酯”或“本发明的化合物”。
(式(2)中,R2表示碳原子数3~6的直链状、支链状或环状的烷基。)
式(2)中,作为R2,具体而言,可举出正丙基、异丙基、正丁基、异丁基(2-甲基丙基)、仲丁基(1-甲基丙基)、叔丁基、正戊基、1-甲基丁基(2-戊基)、2-甲基丁基、3-甲基丁基、新戊基(2,2-二甲基丙基)、2-甲基丁烷-2-基、1-乙基丙基(3-戊基)、3-甲基丁烷-2-基、正己基、1-甲基戊基(2-己基)、2-甲基戊基、3-甲基戊基、4-甲基戊基、2-甲基戊烷-2-基、2,2-二甲基丁基、3,3-二甲基丁基、3-甲基戊烷-2-基、2,3-二甲基丁基、4-甲基戊烷-2-基、3-己基、2-乙基丁基、2,3-二甲基丁烷-2-基、3,3-二甲基丁烷-2-基、4-甲基戊烷3-基、环丙基、环丁基、环戊基、环己基等。
R2具有手性碳的情况下,式(2)所示的化合物包括由此产生的光学异构体中的任一个或任意比例的混合物。
本发明的异丁酸酯特别优选在式(2)中R2选自正丙基、异丙基、正丁基、异丁基和环戊基。
即,本发明的异丁酸酯特别优选为以下的化合物。
式(2)中,R2为正丙基。
式(2)中,R2为异丙基。
式(2)中,R2为正丁基。
式(2)中,R2为异丁基。
式(2)中,R2为环戊基。
作为本发明的异丁酸酯优选的化合物为下述式(2-1)~(2-34)中任一者所示的化合物,特别优选为式(2-1)~(2-5)中任一者所示的化合物。
应予说明,本发明的异丁酸酯为式(1)所示的化合物中将R1限定为碳原子数3~6的直链状、支链状或环状的烷基的化合物。因此,本发明的异丁酸酯单独作为香料是有用的,并且,作为香料组合物的有效成分是有用的。
另外,本发明的异丁酸酯优选作为香料使用,更优选用于赋予类似薄荷或类似水果的香味。
[本发明的异丁酸酯和式(1)所示的化合物的制造方法]
式(2)所示的本发明的异丁酸酯和式(1)所示的化合物的制造方法没有特别限制,可以从以往公知的方法中适当地选择而使用。
例如可以举出通过在催化剂的存在下或者在没有催化剂存在的情况下使α-羟基异丁酸酯与甲酰化剂反应而使α位的羟基进行甲酰化的方法。作为使用的甲酰化剂,可举出甲酸这样的羧酸、甲酸酐、甲酸乙酸酐这样的羧酸酐、甲酰氯、甲酰溴这样的羧酸卤化物等。另外,可以以任意的比例组合使用从这些中选择的2个以上的甲酰化剂。
将使用羧酸、羧酸酐、羧酸卤化物的情况的反应式示于下述式(3)。
式(3)中,R表示碳原子数1~6的直链状、支链状或环状的烷基。Y根据甲酰化剂的种类而不同,例如表示羟基、甲酰氧基、乙酰氧基、氯、溴、碘等。
另外,通过在催化剂的存在下使其它种类的α-甲酰氧基异丁酸酯与醇发生酯交换反应,能够制造目标α-甲酰氧基异丁酸酯。将该反应的反应式示于下述式(4)。
式(4)中,R表示碳原子数1~6的直链状、支链状或环状的烷基。R’只要是与R不同的烷基,则没有特别限制。
同样地在催化剂的存在下使α-甲酰氧基异丁酸与醇发生酯化反应,能够制造目标α-甲酰氧基异丁酸酯。将该反应的反应式示于下述式(5)。
式(5)中,R表示碳原子数1~6的直链状、支链状或环状的烷基。
对于这些反应中使用的催化剂、反应方式、反应条件和反应装置等,能够使用以往公知的催化剂、反应方法、反应条件和反应装置,没有特别限制。另外,对于对所得到的式(2)所示的本发明的异丁酸酯和式(1)所示的化合物进行精制的方法,能够采用现有公知的精制方法,不受任何限制。
实施例
以下,参照实施例,更详细说明本发明,但本发明并不限于这些实施例。
反应成绩的评价根据下述式评价。
反应收率(%)=[(反应液中的生成酯的摩尔数)/(配料液中的原料酯的摩尔数)]×100%
<气相色谱分析(GC分析)>
装置:GC-2010(株式会社岛津制作所制,制品名)
检测器:FID
柱:DB-1(J&W制毛细管柱,制品名)(0.25mmφ×60m×0.25μm)
<NMR波谱分析>
酯的鉴定通过1H-NMR测定和13C-NMR测定而进行。测定条件如下所示。
装置:ECA500(日本电子株式会社制,制品名)
〔1H-NMR〕
核种类:1H
测定频率:500MHz
测定试样:5%CDCl3溶液
〔13C-NMR〕
核种类:13C
测定频率:125MHz
测定试样:5%CDCl3溶液
<气相色谱质谱分析(GC-MS分析)>
化合物的鉴定通过利用GC-MS测定(化学电离法[Cl+]、高分辨率质谱分析[毫克质量])确定分子量而进行。测定条件如下所示。
GC装置:Agilent 7890A(Agilent公司制,商品名)
GC测定条件
柱:DB-1(J&W制毛细管柱,制品名)(0.25mmφ×30m×0.25μm)
MS装置:JMS-T100GCV(日本电子株式会社制,制品名)
MS测定条件:化学电离法
检测器条件:200eV,300μA
试剂气体:异丁烷
记录在利用化学电离法而质子化的状态下检测到的碎片的精确分子量(Exact.Mass)值、和由此归属得到的化学组成式。
<基于色谱法的生成物分离>
基于色谱法的生成物分离使用下述的材料。
填充剂:Wakogel C-200(和光纯药工业株式会社制,商品名)
展开溶剂:乙酸乙酯-己烷
<实施例1:α-甲酰氧基异丁酸甲酯的合成>
在具备冷却管、搅拌装置的200mL玻璃制圆底烧瓶中填充α-羟基异丁酸甲酯(三菱瓦斯化学株式会社制)20.0g、乙酸酐(和光纯药工业株式会社制)57.0g、甲酸(和光纯药工业株式会社制)25.7g、吡啶(和光纯药工业株式会社制)5.3g,在0℃~室温下进行36小时搅拌,使其反应。由反应液的GC分析可确认:利用下述式(6)的反应,以反应收率71%得到α-甲酰氧基异丁酸甲酯,不生成α-乙酰氧基异丁酸甲酯。之后,利用10%碳酸氢钠水溶液进行3次清洗操作,利用饱和氯化钠水溶液进行2次清洗操作,利用硫酸镁干燥后进行浓缩。继续利用柱色谱得到α-甲酰氧基异丁酸甲酯13.4g(基于GC分析的纯度(以下也称为GC纯度):98.6%)。
<参考例1:α-羟基异丁酸乙酯的合成>
在具备蒸馏管的300mL玻璃制烧瓶中填充α-羟基异丁酸甲酯(三菱瓦斯化学株式会社制)56.7g、乙醇(和光纯药工业株式会社制)33.2g、四乙氧基钛(和光纯药工业株式会社制)0.92g。在常压下加热回流并且进行酯交换反应,将生成的甲醇提取到体系外,并且进行96小时反应。其结果是以反应收率97%得到α-羟基异丁酸乙酯。向反应体系中加水,使催化剂失活后进行减压蒸馏,作为71mmHg、77℃的馏分,得到α-羟基异丁酸乙酯46.9g(GC纯度:99.6%)。
<参考例2~6:各种α-羟基异丁酸酯的合成>
使用与参考例1相同的反应装置,将在适量的α-羟基异丁酸甲酯(三菱瓦斯化学株式会社制)与各种醇(正丙醇、异丙醇、正丁醇、异丁醇、环戊醇)在四烷氧基钛和/或烷醇钠这样的适当的催化剂的存在下,根据情况在己烷、甲苯这样的溶剂共存下,加热并且在适当的反应条件下进行酯交换反应。将根据反应生成的甲醇在反应条件下利用蒸馏或与反应溶剂共沸而向体系外排出,并且完成酯交换反应,进行与参考例1相同的分离操作,分别得到以下的α-羟基异丁酸酯。将得到的异丁酸酯的GC纯度一并标注。
α-羟基异丁酸正丙酯(GC纯度:99.8%)
α-羟基异丁酸异丙酯(GC纯度:99.6%)
α-羟基异丁酸正丁酯(GC纯度:99.9%)
α-羟基异丁酸异丁酯(GC纯度:99.6%)
α-羟基异丁酸环戊酯(GC纯度:99.8%)
<实施例2~7:各种α-甲酰氧基异丁酸酯的合成>
使用与实施例1同样的反应装置,适量使用参考例1~6中制备的各种α-羟基异丁酸酯、乙酸酐(和光纯药工业株式会社制)、甲酸(和光纯药工业株式会社制)、吡啶(和光纯药工业株式会社制)进行反应。与实施例1同样地操作,利用柱色谱分别得到下述各种α-甲酰氧基异丁酸酯类。记载所得到的酯的GC纯度,对于新物质,一并标注了NMR波谱分析和GC-MS分析的结果。
〔α-甲酰氧基异丁酸乙酯〕
GC纯度:99.7%
〔α-甲酰氧基异丁酸正丙酯〕
GC纯度:99.7%
1H NMR(500MHz,CDCl3)δ0.94(3H,t,J=7.5Hz),1.61(6H,s),1.65-1.69(2H,m),4.11(2H,t,J=7.0Hz),7.96(1H,s)
13C NMR(125MHz,CDCl3)δ10.2,21.7,24.6,67.0,78.8,159.6,171.9
精确分子量175.10114(C8H14O4,母峰),129.09456(C7H12O2)
〔α-甲酰氧基异丁酸异丙酯〕
GC纯度:99.0%
1H NMR(500MHz,CDCl3)δ1.25(6H,d,J=6.5Hz),1.59(6H,s),5.06(1H,sept,J=6.5Hz),7.95(1H,s)
13C NMR(125MHz,CDCl3)δ21.4,24.4,69.0,78.8,159.5,171.3
精确分子量175.10092(C8H14O4,母峰),133.05323(C5H9O4)
〔α-甲酰氧基异丁酸正丁酯〕
GC纯度:99.9%
1H NMR(500MHz,CDCl3)δ0.94(3H,t,J=7.5Hz),1.36-1.40(2H,m),1.60(s,6H),1.61-1.64(2H,m),4.15(2H,t,J=7.0Hz),7.96(1H,s)
13C NMR(125MHz,CDCl3)δ13.6,19.0,24.6,30.4,65.3,78.8,159.6,171.9
精确分子量189.11665(C9H16O4,母峰),143.11054(C8H14O2)
〔α-甲酰氧基异丁酸异丁酯〕
GC纯度:99.5%
1H NMR(500MHz,CDCl3)δ0.94(6H,d,J=7.0Hz),1.61(6H,s),1.96(1H,m),3.93(2H,d,J=7.0Hz),7.97(1H,s)
13C NMR(125MHz,CDCl3)δ18.9,24.6,27.6,71.5,78.9,159.6,171.9
精确分子量189.11679(C9H16O4,母峰),143.11040(C8H14O2)
〔α-甲酰氧基异丁酸环戊酯〕
GC纯度:99.4%
1H NMR(500MHz,CDCl3)δ1.58(6H,s),1.58-1.63(2H,m),1.66-1.75(4H,m),1.80-1.88(2H,m),5.21(1H,m),7.95(1H,s)
13C NMR(125MHz,CDCl3)δ22.6,24.5,32.3,78.4,78.9,159.5,171.5
精确分子量201.11628(C10H16O4,母峰),133.05459(C5H8O4)
对于通过上述的方法得到的各种α-甲酰氧基异丁酸酯,将利用调香师进行香气评价的结果示于表1。
[表1]
表1
<香料材料的生物分解性评价>
作为化合物的生物分解性的评价方法之一,有OECD测试指南301C,可以根据化合物和好氧性微生物共存的水溶液中的生物化学的氧需求量与实际的氧消耗速度来判断化合物的生物分解性的优劣。
作为由被验物质的化学结构容易且精度良好地推算基于该试验方法的化合物的生物分解的概率的方法,已知有“Biowin5”、“Biowin6”之类的计算软件。
该软件作为美利坚合众国环境保护厅(United States EnvironmentalProtection Agency,EPA)出于评价化学物质对环境的影响的目的而制作完成的“TheEstimations Programs Interface for Windows version 4.1”这一计算软件的模块之一,被散发给公众,在Globally Harmonized System of Classification and Labellingof Chemicals(GHS)的化合物分类、美利坚合众国环境保护厅的新化学物质审查中被利用。使用该软件,评价现有的香料材料和本发明的化合物的生物分解性的差异。
作为与本发明的化合物类似的现有的香料材料的代表例,选择具有类似薄荷的香调的薄荷脑、薄荷酮、香芹酮和具有花香香调的(E)-α-二氢大马酮、(E)-β-大马酮,与本发明的化合物一起进行评价。将用于向软件输入的SMILES式和基于“Biowin5(线形预测模型)”、“Biowin6(非线形预测模型)”的易分解性的概率的输出结果示于表2~表3。结果的数字越大,表示分解性越好,为0.5以上时判定为易分解性(表中,符号“A”),小于0.5时判定为难分解性(表中,符号“B”)。
根据表2~表3可得到如下的结果:相对于类似的现有的香料材料即薄荷脑、薄荷酮、香芹酮、(E)-α-二氢大马酮、(E)-β-大马酮,本发明的化合物能够期待良好的生物分解性。本发明的化合物通过作为香料释放到环境后容易进行生物分解,示出了对环境的负荷更少的倾向。
[表2]
表2
[表3]
表3
<实施例8:白花型的香料组合物>
在具有表4所示的组成的香料组合物77.1质量份中加入实施例7中得到的α-甲酰氧基异丁酸环戊酯22.9质量份,调合香料组合物。
通过调香师进行香气评价,通过在具有表4所述的组成的香料组合物中添加实施例7的α-甲酰氧基异丁酸环戊酯,整体上绿调和丁香酚香气变得柔和,有完整感。其结果是得到了赋予柔和的类似玫瑰的花香和新鲜且清爽的柑橘感的、自然且品质好的类似康乃馨的花香调香气的香料组合物。认为该香料组合物的香气适合于对粉底、除臭粉等赋香。
[表4]
表4
配合成分 | 质量份 |
苯乙醇 | 13.1 |
乙酸4-叔丁基环己酯 | 11.7 |
水杨酸己酯 | 11.1 |
檀香木油(10%) | 10.9 |
柠檬油 | 10.7 |
芳樟醇 | 5.3 |
柠檬烯 | 5.2 |
橙花醇 | 2.7 |
红木油(10%) | 2.7 |
苯乙醛二甲基缩醛 | 2.4 |
丁香酚 | 1.2 |
合计 | 77.1 |
*表中有括号记载的配合成分作为利用二丙二醇稀释后的溶液进行使用。数字表示该溶液中包含的香料的质量%。
<实施例9:白花型的香料组合物>
在具有表5所示的组成的香料组合物67.8质量份中加入实施例4中得到的α-甲酰氧基异丁酸异丙酯32.2质量份,调合香料组合物。
通过调香师进行香气评价,通过在具有表5记载的组成的香料组合物中添加实施例4的α-甲酰氧基异丁酸异丙酯,整体上木质感增加,从而强调了果味和花香,得到了提神醒脑和完整性。其结果是得到了赋予花香和木质感的、粉末且品质好的木质且花香香气的香料组合物。认为该香料组合物的香气适合于对粉底、除臭粉、化妆水、乳液等赋香。
[表5]
表5
配合成分 | 质量份 |
香豆素(5%) | 16.0 |
香叶醇 | 9.2 |
环十五烷酮(25%) | 8.6 |
甜橙油(10%) | 8.3 |
2-苯基乙醇 | 5.3 |
柠檬烯 | 4.6 |
薰衣草油(10%) | 4.2 |
乙酸苄酯(10%) | 3.2 |
芳樟醇 | 2.9 |
γ-十一内酯 | 2.3 |
柠檬油 | 2.2 |
依兰油 | 1.0 |
合计 | 67.8 |
*表中有括号记载的配合成分作为利用二丙二醇稀释而成的溶液进行使用。数字表示该溶液中包含的香料的质量%。
工业上的可利用性
本发明的在α位具有甲酰氧基的异丁酸酯化合物具有优异的香气,其本身作为香料使用备受期待,并且,通过将该化合物作为调合香料原材料使用,得到香气性优异的香料组合物,通过配合于各种制品,从而发挥所希望的赋香性。
进而显示出:实施例中得到的化合物均具有优异的生物分解性,对环境的负荷低,适于使用。
Claims (2)
1.式(1)所示的化合物的作为香料的用途,
式(1)中,R1表示选自乙基、正丙基、异丙基、正丁基、异丁基以及环戊基中的烷基。
2.根据权利要求1所述的用途,其中,式(1)所述的化合物赋予类似薄荷或类似水果的香味。
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