CN110869348A - 吡咯化合物、香料组合物、以及含有它们的饮食品及化妆品 - Google Patents
吡咯化合物、香料组合物、以及含有它们的饮食品及化妆品 Download PDFInfo
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- CN110869348A CN110869348A CN201880044456.4A CN201880044456A CN110869348A CN 110869348 A CN110869348 A CN 110869348A CN 201880044456 A CN201880044456 A CN 201880044456A CN 110869348 A CN110869348 A CN 110869348A
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- Prior art keywords
- tea
- compound
- food
- fragrance
- methyl
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- 235000013305 food Nutrition 0.000 title claims description 46
- 239000002537 cosmetic Substances 0.000 title claims description 32
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- 239000003205 fragrance Substances 0.000 claims abstract description 54
- 238000000034 method Methods 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 10
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 9
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- 239000000796 flavoring agent Substances 0.000 claims description 30
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- 239000004480 active ingredient Substances 0.000 claims description 5
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- 238000006243 chemical reaction Methods 0.000 description 22
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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Classifications
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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
- C11B9/0069—Heterocyclic compounds
- C11B9/0092—Heterocyclic compounds containing only N as heteroatom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F3/00—Tea; Tea substitutes; Preparations thereof
- A23F3/16—Tea extraction; Tea extracts; Treating tea extract; Making instant tea
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F3/00—Tea; Tea substitutes; Preparations thereof
- A23F3/16—Tea extraction; Tea extracts; Treating tea extract; Making instant tea
- A23F3/18—Extraction of water soluble tea constituents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F3/00—Tea; Tea substitutes; Preparations thereof
- A23F3/40—Tea flavour; Tea oil; Flavouring of tea or tea extract
- A23F3/405—Flavouring with flavours other than natural tea flavour or tea oil
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F5/00—Coffee; Coffee substitutes; Preparations thereof
- A23F5/24—Extraction of coffee; Coffee extracts; Making instant coffee
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23F—COFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
- A23F5/00—Coffee; Coffee substitutes; Preparations thereof
- A23F5/46—Coffee flavour; Coffee oil; Flavouring of coffee or coffee extract
- A23F5/465—Flavouring with flavours other than natural coffee flavour or coffee oil
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/205—Heterocyclic compounds
- A23L27/2054—Heterocyclic compounds having nitrogen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/27—Smoke flavours
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
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Abstract
Description
技术领域
本发明涉及吡咯化合物、香料组合物、以及含有它们的饮食品及化妆品。
背景技术
由于饮食品的香气、味道对消费者的嗜好造成很大影响,因此,可以说是赋予该饮食品特征的重要的要素之一。近年来,随着消费者的嗜好趋于多样化,谋求具有各种香气、香味的饮食品。另外,不仅饮食品,而且在化妆品的领域中,其香气也是重要的要素,伴随对高级感的向往的提高,对具有具天然感的香气、香味的制品的需求提高。
在这样的背景下,作为强化或赋予所期望的香气的的技术,正在进行将饮食品、化妆品的香气成分作为香料成分进行添加。
其中,可以说赋予了焙煎饮食品所具有的香馥的焙煎香气、香味的饮食品或化妆品的嗜好性非常高,是今后也期待需求会增加的物质之一。
例如,日本特开2015-208286号公报中提出了如下技术:为了对饮食品赋予自然的焙煎香,添加含有2-甲基吡嗪等各种吡嗪系化合物的焙煎茶提取物。而且,作为具有赋予这样的焙煎香的作用的化合物,可举出例如:2-乙基-3,5-二甲基吡嗪、2-乙烯基-3,5-二甲基吡嗪、愈创木酚等(水上裕造:使用溶剂辅助风味蒸发装置的利用高真空蒸馏和香气提取物稀释分析法的焙茶茶叶香气助益成分的特定.茶研报(2012),No.113,55-62.)。
发明内容
但是,谋求能够容易得到更香馥的焙煎感且赋予天然感优异的香气的方法。
因此,本发明是鉴于上述情况而完成的,其目的在于,提供一种有效地有助于香馥的焙煎感且能够赋予具天然感的香气的方案。
本发明人为了解决上述的问题,进行了深入研究,结果发现:作为下述式(1)表示的化合物的吡咯类似体容易有助于香馥的焙煎感,另外,具有具天然感的香气,从而完成了本发明。
即,上述目的通过以下的技术方案来实现。
1.一种化合物,其由下述式(1)表示,
[上述式(1)中,R1为碳原子数1~3的直链或支链的烷基或羟基,R2为1-吡咯基、2-吡咯基或3-吡咯基];
2.一种香料组合物,其含有上述式(1)表示的化合物作为有效成分;
3.一种饮食品,其含有上述1所述的化合物或上述2所述的香料组合物;
4.根据上述3所述的饮食品,其中,上述饮食品为茶饮料;
5.一种化妆品,其含有上述1所述的化合物或上述2所述的香料组合物;
6.一种对饮食品赋予焙煎香的方法,其包括如下工序:将上述1所述的化合物或上述2所述的香料组合物添加于饮食品。
具体实施方式
以下,对本发明的实施方式进行说明。
[吡咯化合物]
本发明的一个方式为一种化合物,其由下述式(1)表示。
[上述式(1)中,R1为碳原子数1~3的直链或支链的烷基或羟基,R2为1-吡咯基、2-吡咯基或3-吡咯基]
本发明人惊人地发现:作为有助于焙煎香的化合物,与现有已知的吡嗪系化合物等不同,如上述式(1)所示,具有两个吡咯环的吡咯化合物(本说明书中,有时也简称为“本发明的一个方式的化合物”、“吡咯化合物”等)容易有助于香馥的焙煎感(香气贡献度高),具有具天然感的香气。因此,通过将上述式(1)表示的吡咯化合物添加于饮食品或化妆品,能够对它们赋予具天然感的优异的焙煎香。因此,根据本发明,提供一种有效地有助于香馥的焙煎感,且能够赋予具天然感的香气的方案。
以下,对本发明的一个方式的吡咯化合物进行说明。
上述式(1)中,R1为碳原子数1~3的直链或支链的烷基或羟基(-OH基)。作为R1的碳原子数1~3的直链或支链的烷基的具体例,可举出:甲基、乙基、正丙基、异丙基。
其中,从得到香气贡献度更高(可以以少量呈现焙煎香)的化合物的观点考虑,优选碳原子数小的烷基及羟基。具体而言,R1优选为甲基、乙基或羟基(-OH基),更优选为甲基或羟基,特别优选为甲基。
上述式(1)中,R2为1-吡咯基(下述式(a))、2-吡咯基(下述式(b))或3-吡咯基(下述式(c))(需要说明的是,以下的式(a)~(c)中,“*”表示键合部位。):
其中,从可以将制造工序简化、另外得到香气贡献度更高(可以以少量呈现焙煎香)的化合物的观点考虑,R2优选为1-吡咯基(上述式(a))或2-吡咯基(上述式(b)),特别优选为1-吡咯基(上述式(a))。认为在R2为1-吡咯基时,与为2-吡咯基或3-吡咯基的情况相比,化合物的极性比较低,因此,熔点及沸点变低,因此,香气贡献度进一步升高。
进而,上述式(1)中,“-CH2-R2”的吡咯环上的取代位置可以为2位(下述式(1-1)),也可以为3位(下述式(1-2))。即,上述式(1)表示的化合物可采用以下的方式:
其中,从得到香气贡献度高的化合物的观点考虑,“-CH2-R2”的吡咯环上的取代位置优选为2位(上述式(1-1))。
作为上述式(1)表示的化合物的优选的实例,可举出以下的化合物(A)~(E)。其中,从香气贡献度高的观点考虑,优选化合物(A)及(B)。
作为上述吡咯化合物的制造方法,没有特别限制,可以进行合成,另外,也可以从天然物(例如咖啡、绿茶、红茶、乌龙茶、麦茶等)中提取。
上述吡咯化合物的合成可以将公知的方法适当改变,另外可以将这些方法组合而进行。例如,通过使用1-烷基吡咯和1-羟基甲基吡咯同时进行阿佩尔反应及加成反应,可以合成上述吡咯化合物(例如参照实施例的项中的反应式(2))。另外,也可以采用将1-羟基甲基吡咯的羟基通过公知的方法进行卤化而得到卤化物之后,进行该卤化物和1-烷基吡咯的偶联反应的方法。进而,也可以采用进行1-烷基-2-羟基甲基吡咯和吡咯的偶联反应的方法(例如参照实施例的项中的反应式(5))。
从天然物中提取的方法也没有特别限制,通过使用适当的溶剂进行提取并浓缩,可以得到上述吡咯化合物。
[香料组合物]
本发明中,作为另一方式,还提供一种含有上述吡咯化合物的香料组合物。即,本发明的另一方式为一种香料组合物,其含有下述式(1)表示的化合物作为有效成分。
[上述式(1)中,R1为碳原子数1~3的直链或支链的烷基或羟基,R2为1-吡咯基、2-吡咯基或3-吡咯基]
如上所述,上述式(1)表示的化合物有助于香馥的焙煎感,具有具天然感的香气。因此,通过将含有上述式(1)表示的化合物的香料组合物添加于饮食品或化妆品,能够对它们赋予具天然感的优异的焙煎香。需要说明的是,香料组合物中所含的上述吡咯化合物可以为单独1种,也可以混合2种以上。
本实施方式的香料组合物含有上述吡咯化合物作为有效成分。这里,将上述吡咯化合物“作为有效成分而含有”意指以发挥所期望的香气(焙煎香)的充分的量含有。因此,本实施方式的香料组合物可以仅含有本发明的吡咯化合物,但只要不损害所期望的香气,也可以含有其它香料成分、或溶剂等其它添加剂等。
作为其它香料成分,没有特别限制,可以使用公知的成分,例如可举出各种合成香料、天然香料、天然精油、植物提取物等。可举出例如“专利厅、公知惯用技术集(香料)第Ⅱ部食品香料、P7-87、平成12年1月14日发行”中所记载的天然精油、天然香料、合成香料。
作为这样的香料,例如可举出罗勒烯、柠檬萜、β-石竹烯、α-法呢烯、α-或β-蒎烯、α,β-或γ-萜品烯、莰烯、α-雪松烯、香叶烯、α-或β-水芹烯、对甲基异丙基苯、α-或β-杜松烯、1-或2-甲基萘、1-异丙基-4-甲基苯、1,4-二甲基苯、乙基苯、三甲基苯、乙基甲基苯、丙基苯、异丙基苯、二甲基苯乙烯、叔丁基苯、二乙基苯、甲基丙基苯、四氢萘、1,1-二甲基萘、三甲基二氢萘、1,6-二甲基-4-甲基萘、3-甲基-6-(1-甲基亚乙基)环己烯、δ-3-蒈烯等烃类;正丙醇、2-丙醇、正丁醇、异丁基醇、2-丁醇、2-戊醇、3-戊醇、2-甲基-3-丁烯-2-醇、异戊醇、戊醇、正己醇、(Z)-2-戊烯-1-醇、1-戊烯-3-醇、(E)-2-己烯-1-醇、(Z)-或(E)-3-己烯-1-醇、2-乙基-1-己醇、庚醇、辛醇、2-辛烯-1-醇、1-辛烯-3-醇、1,5-辛二烯-3-醇、正壬醇、苄醇、2-苯氧基乙醇、1-或2-苯基乙醇、苯基乙基二甲基甲醇、2,4-二甲氧基苯甲醇、羟基香茅醛、香茅醇、香叶醇、橙花醇、里哪醇、法呢醇、橙花叔醇、α-萜品醇、1-或4-萜品醇、α-或δ-杜松烯醇、库贝醇(クベノール)、β-桉叶醇、雪松醇、香芹醇、桃金娘烯醇、异植醇、3,7-二甲基-1,5,7-辛三烯-3-醇、3,7-二甲基-1,5-辛二烯-3,7-二醇、薄荷醇、4-戊烯-1-醇、2-甲基丁烷-1-醇、1-己烯-3-醇、2-甲基-1-戊烯-3-醇、2-甲基-2-戊醇、3-甲基-2-戊醇、(E)-4-庚烯醇、2-甲基己醇、2,5-辛二烯醇、(E,E)-3,5-辛二烯-3-醇、(E)-2-辛烯醇、5-十一烷醇、对-1,4-二烯-7-醇、4-双缩松油醇、1-萜品醇、龙脑、二氢香芹醇、E,E-法呢醇、植醇等醇类;乙醛、丙醛、异丁醛、丁醛、戊醛、异戊醛、(E)-2-庚烯醛、(Z)-4-庚烯醛、(E)-2-戊烯醛、(Z)-3-戊烯醛、2-甲基丁醛、己醛、(E)-2-己烯醛、(Z)-3-己烯醛、(E,E)-2,4-己二烯醛、(E,Z)-2,4-己二烯醛、庚醛、(E,Z)-2,4-庚二烯醛、(E,E)-2,4-庚二烯醛、辛醛、(E)-2-辛烯醛、(E,E)-2,4-辛二烯醛、(E,Z)-2,4-辛二烯醛、壬醛、(E)-2-壬烯醛、(E,E)-或(E,Z)-2,4-壬二烯醛、(E,Z)-2,6-壬二烯醛、癸醛、(E)-2-癸烯醛、(E)-4,5-环氧基-2-癸烯醛、(E,E)-2,4-癸二烯醛、(E)-2-十一醛、水杨醛、对羟基苯甲醛、2,5-二甲基苯甲醛、香草醛、紫苏醛、肉桂醛、己基肉桂醛、藏花醛、香叶醛、橙花醛、β-环柠檬醛、茴香醛、苯甲醛、2-苯基丁醛、2-甲基-2-戊烯醛、4-甲基-2-戊烯醛、2-甲基戊醛、3-甲基戊醛、2,4-二甲基-2,4-庚二烯醛、2,4,6-癸三烯醛、(E)-2-十三烯醛、4-乙基-7,11-二甲基-(2E,6,10E)-十二烷三烯醛、苯甲醛、2-或4-甲基苯甲醛、4-乙基苯甲醛、4-羟基-3,5-二甲氧基苯甲醛、4-甲基-2-苯基-2-戊烯醛、5-甲基-2-苯基-2-己醛等醛类;
甲乙酮、3-羟基丁酮、双乙酰、(Z)-或(E)-3-戊烯-2-酮、4-甲基-3-戊烯-2-酮、3-己烯-2-酮、2-庚酮、3,5-庚二烯-2-酮、6-甲基-3,5-庚二烯-2-酮、1-辛烯-3-酮、3-辛烯-2-酮、4-辛烯-2-酮、(E,Z)、(E,E)-或(Z,E)-3,5-辛二烯-2-酮、(Z)-1,5-辛二烯-3-酮、3-甲基-2,4-壬二酮、2-癸酮、2,6,10-三甲基十七酮、环己酮、顺式茉莉酮、2,2,6-三甲基环己酮、α-或β-大马酮、α-或β-二氢大马酮、4-氧代-β-紫罗兰酮、α-或β-紫罗兰酮、5,6-环氧基-β-紫罗兰酮、3,4-二氢-β-紫罗兰酮、7,8-二氢-α-紫罗兰酮、5,6-二羟基-β-紫罗兰酮、香叶基丙酮、2,3-戊二酮、2-戊酮、3-戊酮、4-甲基-3-戊烯-2-酮、2-庚酮、(3E,5E)-6-甲基-庚二烯-2-酮、2-甲基-2-庚烯-6-酮、2-辛酮、3-辛酮、2-壬酮、5-乙基-6-甲基-2-庚酮、2-癸酮、6,10-二甲基-2-十一酮、甲基十四烷-3-酮、6,10,14-三甲基-2-十五酮、2,3-二甲基环己酮、3-羟基环己酮、异佛尔酮、2,6,6-三甲基环己酮、2,2,6-三甲基-6-羟基环己酮、2,2,6-三甲基-4-羟基环己酮、2-羟基苯乙酮、4-甲基苯乙酮、1,3-或1,4-二乙酰基苯、4-乙基苯乙酮、3,4-二甲基苯乙酮、苄基乙基酮、2-甲氧基甲基苯乙酮、1-(2,4-二甲氧基苯基)-1-丙酮、樟脑、葑酮、长叶薄荷酮、4-(1-羟基-4-氧代-2,6,6-三甲基-2-环己烯基)-3-丁烯-2-酮、1,5,5,9-四甲基双环-[4.3.0]-8-壬烯-7-酮、1,2-苏型-1,2-二羟基-β-紫罗兰酮等酮类;乙酸、丙酸、戊酸、4-甲基戊酸、(E)-2-己烯酸、(Z)-3-己烯酸、庚酸、辛酸、壬酸、癸酸、癸烯酸、(E)-2-癸烯酸、(Z)-或(E)-香叶酸、香茅酸、苯甲酸、苯基乙酸、水杨酸、甲酸、2-氧代丁烷酸、2-羟基丁烷酸、3-甲基-2-丁烯酸、2-或3-甲基丁烷酸、Z-2-己烯酸、E-3-己烯酸、4-甲基-4-庚烯酸、2,3-或4-甲基戊酸、己酸、(2E,4Z)-或(E,4E)-庚二烯酸、Z-2-庚烯酸、(Z)-或(E)-4-庚烯酸、2,3-或5-甲基己酸、(E)-2-辛烯酸、(Z)-3-或4-辛烯酸、2-乙基己酸、2,3-或6-甲基戊酸、(E)-4-壬烯酸、7-甲基辛酸、2-乙基庚酸、(E)-4-壬烯酸、7-甲基壬酸、2-乙基庚酸、2-或8-甲基壬酸、Z-或E-3-十一烯酸、十一酸、十二酸、十二酸、十四烷酸、十六烷酸、十八酸等羧酸类;
甲酸乙酯、甲酸异戊酯、甲酸己酯、甲酸(Z)-3-己烯酯、甲酸(E)-2-己烯酯、甲酸苯基乙酯、甲酸香叶酯、乙酸甲酯、乙酸乙酯、乙酸丁酯、乙酸异丁酯、乙酸3-甲基丁酯、乙酸(Z)-或乙酸(E)-3-己烯酯、乙酸(E)-2-己烯酯、乙酸己酯、乙酸苯酯、乙酸苯基乙酯、苯基乙酸苯基乙酯、乙酸苄酯、乙酸香叶酯、乙酸α-萜品酯、乙酸橙花酯、乙酸里哪酯、乙酸冰片酯、丙酸(Z)-或丙酸(E)-3-己烯酯、丙酸(E)-己烯酯、丙酸橙花酯、丁酸甲酯、丁酸(Z)-3-己烯酯、丁酸(E)-2-己烯酯、丁酸苄酯、丁酸苯基乙酯、异丁酸苯基乙酯、丁酸己酯、2-甲基丁酸(Z)-3-己烯酯、3-羟基丁酸乙酯、戊酸甲酯、戊酸乙酯、戊酸异丁酯、戊酸(Z)-3-己烯酯、己酸(Z)-或己酸(E)-2-戊烯酯、己酸(E)-2-己烯酯、己酸(Z)-3-己烯酯、己酸苯基乙酯、己酸己基(Z)-3-己烯酸甲酯、(E)-2-己烯酸甲酯、(E)-2-己烯酸(Z)-3-己烯酯、(Z)-3-己烯酸(E)-3-己烯酯、辛酸乙酯、辛酸己酯、辛酸(Z)-3-己烯酯、癸酸乙酯、癸酸丙酯、癸酸己酯、癸酸(Z)-3-己烯酯、苯基乙酸甲酯、苯基乙酸乙酯、苯基乙酸己酯、苯甲酸乙酯、苯甲酸己酯、苯甲酸苄酯、苯甲酸(Z)-3-己烯酯、2-甲氧基苯甲酸甲酯、4-甲氧基苯甲酸甲酯、茉莉酸甲酯、(+)-茉莉酸甲酯(エピジャスモン酸メチル)、(Z)-二氢茉莉酸甲酯、甲基丙酸橙花酯、乙酸1-羟基-2-丙酮、琥珀酸甲酯、戊酸甲酯、辛酸甲酯、4-氧代壬酸甲酯、丁酸2-己酯、十四烷酸甲酯、十五烷酸甲酯、十五烷酸乙酯、11-十六烯酸甲酯、十六烷酸甲酯、十六烷酸乙酯、苯甲酸甲酯等酯类;δ-己内酯、δ-庚内酯、δ-壬内酯、δ-癸内酯、γ-丁内酯、γ-戊内酯、γ-庚内酯、γ-己内酯、γ-辛内酯、γ-壬内酯、2-甲基-γ-丁内酯、2-己烯-4-内酯、4-甲基-5-己烯-4-内酯、5-辛烯-4-内酯、2-壬烯-4-内酯、7-癸烯-4-内酯、地芰普内酯、2-甲基丁内酯、γ-戊内酯、δ-辛内酯、3,7-癸二烯-5-内酯、顺式茉莉内酯、γ-癸内酯、二氢猕猴桃内酯、博伏内酯(bovolide)、二氢博伏内酯(dihydrobovolide)、4-十四内酯等内酯类;甲基胺、乙基胺、二苯基胺、1-乙基吡咯、2-甲酰基吡咯、1-乙基-2-甲酰基吡咯、2-乙酰基吡咯、2-乙酰基-1-乙基吡咯、吲哚、3-甲基吲哚、吡嗪、甲基吡嗪、乙基吡嗪、2,3-二甲基吡嗪、2,5-二甲基吡嗪、2,6-二甲基吡嗪、2-乙基-3-甲基吡嗪、2-乙基-5-甲基吡嗪、2-乙基-6-甲基吡嗪、2-(2'-呋喃基)-5-或2-(2'-呋喃基)-6-甲基吡嗪、2,5-二乙基吡嗪、2,6-二乙基吡嗪、三甲基吡嗪、3-乙基-2,5-二甲基吡嗪、2-乙基-3,5-二甲基吡嗪、2,5-二乙基-3-甲基吡嗪、2,3-二乙基-5-甲基吡嗪、3,5-二乙基-2-甲基吡嗪、四甲基吡嗪、6,7-二氢-5H-环戊并吡嗪、6,7-二氢-2-甲基-5H-环戊并吡嗪、6,7-二氢-5H-环戊并吡嗪、2-(2'-呋喃基)吡嗪、2-甲基吡啶、乙酰基吡啶、3-甲氧基吡啶、3-甲基丁烷腈、苯基腈、喹啉、2-甲基喹啉、6-或7-甲基喹啉、2,4-二甲基喹啉、2,6-二甲基喹啉、4,8-二甲基喹啉、二苯基胺、3-丙基喹啉、2,6-二甲基吡啶、吡咯、1-甲基-2-甲酰基吡咯、1-乙酰基吡咯、2,5-二甲基吡咯、1-甲基-2-乙酰基吡咯、1-甲基-丙酰基吡咯、2-乙酰基-3-糠基吡咯、吡啶、3-或4-甲基吡啶、4-乙烯基吡啶、2-或3-乙基吡啶、2,5-二甲基吡啶、2-乙基-6-甲基吡啶、5-乙基-2-甲基吡啶、丙基吡嗪、2,6-二乙基吡嗪、2,4,5-三甲基唑等含氮化合物类;
甲硫醇、乙硫醇、1-丙硫醇、二甲基硫醚、噻吩、四氢噻吩、2-甲基噻吩、3-甲基噻吩、3-甲基噻吩-2-醛、苯并噻唑、2-丙酰基噻吩、双(2-甲基-3-呋喃基)二硫醚、4-甲氧基-2-甲基-2-丁硫醇及4-巯基-2-戊酮等含硫化合物类;邻甲酚、间甲酚、对甲酚、乙基苯酚、4-乙烯基苯酚、2,3-二甲基苯酚、百里酚、1,3-二-叔丁基-2-甲氧基-5-甲基苯、茴香脑、愈创醇、4-乙基愈创木酚、1,4-二甲氧基苯、二苯基醚、黄樟脑、丁子香酚、香芹酚等酚类;里哪醇氧化物(E异构体或Z异构体的5元环及E异构体或Z异构体的6元环)、2-乙基呋喃、2-戊基呋喃、2,3-二氢呋喃、糠醛、5-甲基糠醛、葫芦巴内酯、呋喃酮、3,4-二甲基-5-戊基-2(5H)-呋喃酮、3,4-二甲基-5-亚戊基-2(5H)-呋喃酮、2-乙酰基呋喃、香豆素、麦芽酚、乙基麦芽酚、茶香螺酮、(Z)-或(E)-茶香螺酮、(E)-茶螺烷、(E)-6,7-环氧基二氢茶螺烷、(E)-6-羟基二氢茶螺烷、糠基醇等呋喃类及吡喃类;肉豆蔻花(メース)、紫罗兰、金合欢、天竺葵、肉豆蔻、印蒿、茉莉、草木犀绿茶、红茶、乌龙茶、麦茶、鼠尾草、干草、橡苔、桂花、芫荽、小茴香、百里香、多香果、月桂树、桦树、小豆蔻、洋芹菜、丁香、莳萝、姜、葫芦巴、欧芹、牛至、牛至属植物、冬青、依兰、鳄梨、紫花苜蓿、玫瑰草等天然香料;茉莉净油、玫瑰净油、晚香玉净油、香草净油等;檀香油、雪松油、橙油、春黄菊油、罗马春黄菊油、小豆蔻油、香紫苏油、柚子油、丁香油、肉桂油、芫荽油、柏油、刺柏油、薄荷油、鼠尾草油等精油类。需要说明的是,上述香料成分可以单独使用1种,也可以以2种以上的组合使用。
另外,作为其它添加剂,没有特别限制,可以使用公知的添加剂,例如可举出水、乙醇等溶剂;乙二醇、丙二醇、二丙二醇、甘油、己二醇、苯甲酸苄酯、柠檬酸三乙酯、邻苯二甲酸二乙酯、氢化松香酸甲酯(ハーコリン)、中链脂肪酸甘油三酯、中链脂肪酸甘油二酯等香料保留剂。需要说明的是,上述其它添加剂可以单独使用1种,也可以组合2种以上使用。
在本实施方式的香料组合物中,上述式(1)表示的吡咯化合物的含量没有特别限制,根据其目的、或所使用的饮食品及化妆品等的种类、香料组合物的种类而不同,例如,相对于香料组合物的总质量,优选为10质量ppt~5质量ppm,更优选为50质量ppt~1质量ppm,特别优选为0.1质量ppb~100质量ppb。通过设为10质量ppt以上,能够充分地赋予有助于香馥的焙煎感的金属的香气。另一方面,通过设为5质量ppm以下,可以抑制赋予过量的香气、香味特性(抑制作为异臭的香气、香味特性的赋予),能够赋予焙煎香气不过于强烈的天然感优异的香气。需要说明的是,香料组合物含有2种以上的上述吡咯化合物的情况下,其合计量优选为上述范围内。
[饮食品]
本发明的另一其它方式为一种饮食品,其含有上述式(1)表示的化合物或上述香料组合物。需要说明的是,饮食品中所含的上述吡咯化合物可以为1种单独,也可以混合2种以上。由于本发明的吡咯化合物及香料组合物大大有助于焙煎香,因此,含有这些物质的饮食品被赋予具有厚度的香馥的丰富的风味、或浓厚美味或使其增强。另外,本发明的吡咯化合物及香料组合物具有具天然感的香气。因此,对含有该吡咯化合物或香料组合物的饮食品赋予更具天然感的优异的焙煎香。
因此,作为本发明的另一其它方式,提供一种对饮食品赋予焙煎香的方法,其包括将上述式(1)表示的化合物或上述香料组合物添加于饮食品。
作为本实施方式的饮食品,没有特别限制,优选为要求香馥的风味的饮食品,例如可举出绿茶(煎茶、焙茶、玄米茶等)、红茶、乌龙茶、麦茶、谷物茶(玉米茶等)等茶饮料、咖啡(包含将蒲公英的根、樱花树的根、牛蒡等进行焙煎而成的所谓的代用咖啡)、啤酒、发泡酒、第3类啤酒、啤酒风味发泡饮料、无酒精啤酒风味饮料等饮料;火腿、香肠、熏肉等加工食用肉、鱼糕等水产加工品、肉类及鱼贝类的熏制品;小甜饼、派、小吃点心等点心类;奶酪、黄油等乳制品、巴旦杏、开心果等坚果类;豆类等、各种即食食品等一般食品类等食品。含有本发明的吡咯化合物或香料组合物的这种饮食品可以通过在饮食品中添加吡咯化合物或香料组合物并进行搅拌而制造,可使用本领域技术人员公知的方法而制造。
其中,本发明的饮食品的优选的方式为茶饮料。作为茶饮料,没有特别限制,除将作为山茶科的常绿树的茶树的叶或茎进行了加工的茶饮料之外,可以举出被称为所谓的代用茶的、将茶树以外的植物(具体而言,为该植物的叶、茎、果实、花瓣等)进行加工而成的茶饮料等。
作为这样的茶饮料,可举出:绿茶(普通煎茶、深蒸煎茶、玉露、冠茶、粗茶、玉绿茶、抹茶、焙茶、玄米茶、芽茶、茎茶等)、红茶、乌龙茶、麦茶、薏仁茶、普洱茶、路易波士茶、马黛茶、熊笹茶、竹茶、荞麦茶、决明子茶、甜茶、甘茶、甘茶蔓茶、杜仲茶、苦丁茶、蕺菜茶、紫苏茶、银藤茶、柚子茶、陈皮茶(蜜柑皮茶)、生姜茶、人参茶等蔬菜茶;桂皮茶、盐渍樱花茶、昆布茶、梅昆布茶、椎茸茶等蘑菇茶;玉米茶、草本植物茶、汉方茶、豆茶等。另外,上述茶中,也可以为混合有2种以上的混合茶。其中,特别优选焙煎香对嗜好性给予影响的茶饮料,具体而言,优选粗茶、焙茶、玄米茶、乌龙茶、麦茶、薏米茶、或含有选自这些中的至少一种的混合茶。
另外,茶的发酵的程度没有特别限定,例如可以为绿茶(不发酵茶)、白茶(弱发酵茶)、青茶(半发酵茶)、红茶(完全发酵茶·全发酵茶)、黄茶(弱后发酵茶)、黑茶(后发酵茶)等中的任一种。进而,上述茶可以为经焙煎的茶,也可以为没有焙煎的茶,另外,在经焙煎的茶中,不管焙煎的程度。
在本实施方式的饮食品中,上述式(1)表示的吡咯化合物的含量没有特别限制,根据其目的、或饮食品的种类而不同,例如,相对于饮食品的总质量,优选为0.01质量ppt(10质量ppq)~1000质量ppb,更优选为0.05质量ppt(50质量ppq)~100质量ppb,特别优选为0.1质量ppt~50质量ppb,最优选为10质量ppt~10质量ppb。通过设为0.01质量ppt以上,可以提供具有香馥的焙煎香的饮食品。另一方面,通过设为1000质量ppb以下,可以抑制赋予过量的香气、香味特性(抑制作为异臭的香气、香味特性的赋予),可以提供具有焙煎香气不过于强的天然感优异的香气的饮食品。需要说明的是,饮食品含有2种以上的上述吡咯化合物时,其合计量优选为上述范围内。
将上述式(1)表示的化合物或上述香料组合物添加于饮食品的方法没有特别限制,可以将上述式(1)表示的化合物或上述香料组合物一次性地或分别阶段性地或连续地加入。另外,混合方法也没有特别限制,可以使用公知的方法。
[化妆品]
本发明的另一其它方式为一种化妆品,其含有上述式(1)表示的化合物或上述香料组合物。需要说明的是,化妆品中所含的上述吡咯化合物可以为单独1种,也可以混合2种以上。由于本发明的吡咯化合物及香料组合物具有具天然感的香气,因此,含有该吡咯化合物或香料组合物的饮食品赋予更具天然感的优异的焙煎香。
作为本实施方式的化妆品,没有特别限制,优选为要求具天然感的焙煎香的化妆品,例如可举出香水;洗发剂、护发素、美发产品(发膏、润发油等)等护发制品;粉底霜、口红、润唇膏、唇彩、化妆水、化妆用乳液、化妆用乳霜、化妆用凝胶、美容液、面膜等化妆品类;防晒制品、阻晒制品等防晒化妆品类;面部用皂、身体用皂、洗涤用皂、洗涤用洗剂、消毒用洗剂、防臭洗剂等保健、卫生用洗剂类;牙膏、薄纸、卫生纸等保健、卫生材料类;室内芳香剂、汽车芳香剂等芳香制品。
另外,作为化妆品的方式(剂型),没有特别限制。例如,可应用于液状、乳液状、乳霜状、浆料状、固体状、多层状等各种方式。除这些方式之外,也可以作为薄片剂、喷雾剂、慕丝剂应用。
含有本发明的吡咯化合物或香料组合物的这种化妆品可以通过在化妆品中添加吡咯化合物或香料组合物并进行搅拌来制造,可使用本领域技术人员公知的方法来制造。
为了使本发明的吡咯化合物或香料组合物以适当的浓度、且均匀地进行分散,本发明的化妆品可以在不损害所期望的香气的限度内含有其它添加剂。
作为其它添加剂,没有特别限制,可以使用公知的添加剂,例如可举出角鲨烷、凡士林、微晶蜡等烃类;荷荷巴油、巴西棕榈蜡、油酸辛基十二烷基酯、乙酸苯基乙酯、丁酸苯基乙酯、甲酸苯基乙酯、苯基乙酸苯基乙酯、异丁酸苯基乙酯、苯甲酸苄酯、丙酸苯基乙酯、乙酸苯基丙酯等酯类;苯基乙醛、苯甲醛、肉桂醛、己基肉桂醛等醛类、橄榄油、牛脂、椰子油等甘油三酯类;硬脂酸、油酸、蓖麻油酸等脂肪酸;里哪醇、香茅醇、白檀醇、二氢月桂烯醇、二氢里哪醇、香叶醇、橙花醇、檀香210、Santalex、萜品醇、四氢里哪醇、苄醇、苯乙基醇、苯基乙基二甲基甲醇、羟基香茅醛等醇类;油醇、硬脂醇、辛基十二烷醇等高级醇;乙二醇、丙二醇、甘油、1,3-丁二醇等多元醇类;吲哚、5-甲基-3-庚酮肟、柠檬萜硫醇、1-对孟烯-8-硫醇、氨茴酸丁酯、氨茴酸顺式3-己烯基酯、氨茴酸苯基乙酯、氨茴酸肉桂酯、二甲基硫醚、8-巯基孟酮等含氮和/或含硫化合物类;磺基琥珀酸酯或聚氧乙烯烷基硫酸钠等阴离子表面活性剂类;烷基甜菜碱盐等两性表面活性剂类;二烷基铵盐等阳离子表面活性剂类;山梨糖醇酐脂肪酸酯、脂肪酸甘油单酯、它们的聚氧乙烯加成物、聚氧乙烯烷基醚、聚氧乙烯脂肪酸酯等非离子表面活性剂类;增稠剂·凝胶剂;抗氧化剂;紫外线吸收剂;颜料;防腐剂;粉体等。另外,除这些物质以外,上述[香料组合物]的项中举出的其它香料成分也可以用作化妆品中的其它添加剂。需要说明的是,上述其它添加剂可以单独使用1种,也可以组合2种以上使用。
在本实施方式的化妆品中,上述式(1)表示的吡咯化合物的含量没有特别限制,根据其目的、或化妆品的种类而不同,例如,相对于化妆品的总质量,优选为0.1质量ppt~100质量ppb,更优选为1质量ppt~10质量ppb,特别优选为10质量ppt~5质量ppb。通过设为0.1质量ppt以上,可以提供具有焙煎香的化妆品。另一方面,通过设为100质量ppb以下,可以抑制赋予过量的香气、香味特性(抑制作为异臭的香气、香味特性的赋予)、可以提供具有焙煎香气不过于强的天然感优异的香气的化妆品。需要说明的是,在化妆品含有2种以上的上述吡咯化合物时,其合计量优选为上述范围内。
实施例
以下,使用实施例及比较例更具体地说明本发明,但本发明并不限定于以下的实施例。另外,只要没有特殊说明,则各操作在室温(25℃)/相对湿度40~50%RH的条件下进行。以下,只要没有特殊说明,则“ppt”及“ppb”分别意指“质量ppt”及“质量ppb”。
需要说明的是,以下,在核磁共振光谱(1H-NMR)测定中,使用JEOL RESONANCE社制的ECX-400A、400MHz。另外,在质量分析光谱(MS)测定中,使用Agilent Technology社制的GC7890B、MS5977A(离子化方式:EI 70eV)。另外,作为GC测定用柱,使用GL Sciences社制的TC-1(长度30m、内径0.25mm、液层膜厚0.25测微计)。
[合成例1:化合物(A)~(B)、(D)的合成]
《1-羟基甲基吡咯(化合物(i))的合成》
首先,按照以下的化学反应式(1),参考美国专利第2492414号说明书中记载的方法,制备1-羟基甲基吡咯(化合物(i))。
化学反应式(1)
对吡咯6.71g(0.1mol)加入多聚甲醛2.85g(0.095mol)及作为催化剂的K2CO30.02g(0.00014mol),加热至50℃。多聚甲醛的结晶完全溶解后,维持在40~55℃并搅拌2小时。用GC-MS(TC-1)确认反应溶液时,该溶液为作为原料化合物的吡咯、作为目标化合物的1-羟基甲基吡咯、以及2-羟基甲基吡咯、2,5-二羟基甲基吡咯的混合物,因此,利用硅胶柱,将目标1-羟基甲基吡咯进行精制。具体而言,进行以下的精制处理。
使用150g的WAKO gel C-100,将己烷/乙酸乙酯设为展开溶剂。一边使己烷/乙酸乙酯的混合比变化,一边进行分馏,得到5.99g的1-羟基甲基吡咯。化合物利用MS而确认;
化合物(i):MS(EI)m/z:97(100),67(52)。
《化合物(A)~(B)、(D)的合成》
接着,按照以下的化学反应式(2),合成化合物(A)~(B)、(D)。
化学反应式(2)
使三苯基膦(Ph3P)0.315g(0.0012mol)溶解于5mL的CCl4。接着,在室温下缓慢地滴加使1-乙基吡咯0.1g(0.001mol)及1-羟基甲基吡咯0.1g(0.001mol)溶解于CCl4 5mL而得到的溶液,之后,加热回流6小时,同时进行阿佩尔反应和加成反应。将得到的反应液用GC-MS(TC-1)进行分析,确认了反应的结束。其后,利用硅胶柱进行精制。具体而言,进行以下的精制处理。
使用3g的WAKO gel C-100,将己烷/乙酸乙酯=99/1(v/v)设为展开溶剂。分馏流出液,分别得到化合物(A)(1-乙基-2-(1-吡咯基甲基)吡咯)、化合物(B)(1-乙基-3-(1-吡咯基甲基)吡咯)、化合物(D)(1-羟基甲基-2-(1-吡咯基甲基)吡咯)。
对得到的化合物,以下示出MS及NMR的结果:
化合物(A):MS(EI)m/z:108(100),174(20),80(18),53(7).1H-NMR(CDCl3,400MHz)δ(ppm)1.13(3H,t,J=7.2Hz),3.73(2H,q,J=7.2Hz),5.02(2H,s),6.12附近(1H,m),6.13(2H,dd,J=2.4,1.6Hz),6.17(1H,dd,J=3.2,1.6Hz),6.62(2H,dd,J=2.4,1.6Hz),6.69(1H,m).
化合物(B):MS(EI)m/z:108(100),174(33),80(17),53(7).
化合物(D):MS(EI)m/z:80(100),176(21),81(20),53(13).
另外,确认上述化合物(A)~(B)、(D)的香调,其结果,任一种均具有香馥的焙煎香。
[合成例2:化合物(C)的合成]
《1-乙基-2-甲酰基吡咯(化合物(ii))的合成》
首先,按照以下的化学反应式(3),制备1-乙基-2-甲酰基吡咯(化合物(ii))。
化学反应式(3)
在1L的四口烧瓶中加入吡咯-2-甲醛19g(0.2mol)和4N KOH 50mL,以油浴加热至100℃。在此,一边进行搅拌,一边用约1小时从各个口滴加硫酸二乙酯92.4g(0.6mol)及4NKOH 175mL。滴加结束后,一边进行搅拌,一边进一步回流1小时(参照美国专利第3403159号说明书)。确认黑色的沉淀的生成之后,在回流后进行冷却。在混合物中加入二乙基醚300mL并充分搅拌,用布氏漏斗过滤后,用分液漏斗将滤液进行分离。用2N KOH 100mL、超纯水100mL清洗有机层。硫酸钠脱水之后,用蒸发器除去二乙基醚,由此得到黑色油状物。对于该黑色油状物,利用硅胶柱进行精制。具体而言,进行以下的精制处理。
使用300g的WAKO gel C-100,将黑色油状物装填于柱之后,通液己烷。其后,通液己烷/乙酸乙酯=95/5(v/v),分馏流出液,由此以黄色油状物的形式得到化合物(ii)11.6g。纯度为98.13%。化合物利用MS而确认。
化合物(ii):MS(EI)m/z:123(100),94(65),122(32),108(30),106(23),80(15),66(15),39(15)。
《1-乙基-2-羟基甲基吡咯(化合物(iii))的合成》
接着,按照以下的化学反应式(4),制备1-乙基-2-羟基甲基吡咯(化合物(iii))。
化学反应式(4)
一边将上述化合物(ii)1.0g(0.008mol)、甲醇9mL、超纯水1mL在冰冷下搅拌,一边缓慢地添加NaBH40.0756g(0.002mol)。一边用GC-MS(TC-1)进行反应追踪,一边继续反应,进一步追加NaBH40.0189g(0.0005mol),进行一整夜搅拌。其后,添加饱和食盐水10mL,使用二乙基醚20mL进行2次分液操作。用同量的饱和食盐水清洗有机层,硫酸钠脱水后,用蒸发器除去二乙基醚,由此得到1.18g的化合物(iii)。化合物利用MS而确认。
化合物(iii):MS(EI)m/z:108(100),125(74),80(43),68(20)。
《化合物(C)的合成》
进而,按照以下的化学反应式(5),合成化合物(C)。
化学反应式(5)
使三苯基膦(Ph3P)0.26g(0.001mol)溶解于2mL的CCl4。接着,缓慢地滴加溶解于8mL的CCl4的上述化合物(iii)0.10g(0.0008mol)和吡咯0.067g(0.001mol)的混合物,在室温下进行搅拌。继续反应2小时后,进行利用硅胶柱的精制。具体而言,进行以下的精制处理。
使用3g的WAKO gel C-100,将己烷/乙酸乙酯设为展开溶剂。将试样装填于柱之后,通液己烷。其后,通液己烷/乙酸乙酯=95/5(v/v),分馏流出液,由此以褐色油状物的形式得到化合物(C)(1-乙基-2-(2-吡咯基甲基)吡咯)26.4mg。纯度为94.75%。
对于得到的化合物,以下示出MS及NMR的结果:
化合物(C):MS(EI)m/z:174(100),173(57),95(37),80(32),145(19).1H-NMR(CDCl3,400MHz)δ(ppm)1.18(3H,t,J=7.2Hz),3.77(2H,q,J=7.2Hz),3.96(2H,s),5.99(2H,m),6.12附近(2H,m),6.64(2H,m),7.87(1H,br).
另外,确认上述化合物(C)的香调,其结果,具有香馥的焙煎香。
[实施例1:添加至焙茶]
在市售的焙茶中以成为以下的表1中记载的浓度的方式添加上述合成例1中得到的化合物(A),由专门小组成员20名进行评价。另外,对2-甲基吡嗪同样地进行评价(比较例1-2)。评价基准如下所述(以下同样):
(评价基准)
-:与对照没有大的差异
+:稍微感觉到具天然感的焙煎香
++:感觉到具天然感的焙煎香
+++:感觉到天然感优异的良好的焙煎香。
[表1]
[实施例2:向绿茶的添加]
在市售的绿茶中以成为以下的表2中记载的浓度的方式添加上述合成例1中得到的化合物(A),与上述实施例1同样地进行评价。
[表2]
[实施例3:向咖啡的添加]
在市售的咖啡中以成为以下的表3中记载的浓度的方式添加上述合成例1中得到的化合物(A),与上述实施例1同样地进行评价。
[表3]
[实施例4:向麦茶的添加]
在市售的麦茶中以成为以下的表4中记载的浓度的方式添加上述合成例1中得到的化合物(A),与上述实施例1同样地进行评价。
[表4]
[实施例5:向无酒精啤酒的添加]
在市售的无酒精啤酒中以成为以下的表5中记载的浓度的方式添加上述合成例1中得到的化合物(A),与上述实施例1同样地进行评价。
[表5]
[实施例6:向铃兰香料组合物的添加]
表6中示出铃兰香料组合物的配方。在本配方中添加上述合成例1中得到的化合物(A),与上述实施例1同样地进行评价。需要说明的是,只要没有特殊说明,则表6中的各数值的单位为“质量份”。需要说明的是,实施例6-1的铃兰香料组合物是对比较例6-1的铃兰香料组合物以成为1质量ppb的浓度的方式加入化合物(A)而得到的。
[表6]
[表7]
由上述表1~5、7的结果显示:根据本发明的吡咯化合物,有助于香馥的焙煎感的效果(香气贡献度)高,可以赋予饮食品及化妆品具天然感的香气。
进而,本申请基于2017年7月26日提出申请的日本专利申请号2017-144630号,其公开内容通过参照而整体纳入本说明书中。
Claims (6)
3.一种饮食品,其含有权利要求1所述的化合物或权利要求2所述的香料组合物。
4.根据权利要求3所述的饮食品,其中,所述饮食品为茶饮料。
5.一种化妆品,其含有权利要求1所述的化合物或权利要求2所述的香料组合物。
6.一种对饮食品赋予焙煎香的方法,其包括如下工序:将权利要求1所述的化合物或权利要求2所述的香料组合物添加于饮食品。
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JP2017-144630 | 2017-07-26 | ||
PCT/JP2018/019862 WO2019021608A1 (ja) | 2017-07-26 | 2018-05-23 | ピロール化合物、香料組成物、ならびにこれらを含有する飲食品および香粧品 |
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JP6917327B2 (ja) * | 2018-03-14 | 2021-08-11 | 長谷川香料株式会社 | 精製された茶抽出物の製造方法、精製された茶抽出物および香料組成物、ならびにこれらを含有する飲食品および香粧品 |
JP7421431B2 (ja) | 2019-10-31 | 2024-01-24 | 小川香料株式会社 | 香気又は香味の改善剤 |
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