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TW201733459A - Flavor modifier containing 4-alkoxycinnamaldehyde derivative as active ingredient - Google Patents

Flavor modifier containing 4-alkoxycinnamaldehyde derivative as active ingredient Download PDF

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Publication number
TW201733459A
TW201733459A TW106107603A TW106107603A TW201733459A TW 201733459 A TW201733459 A TW 201733459A TW 106107603 A TW106107603 A TW 106107603A TW 106107603 A TW106107603 A TW 106107603A TW 201733459 A TW201733459 A TW 201733459A
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Taiwan
Prior art keywords
food
sweetness
flavor
drinks
drink
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TW106107603A
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Chinese (zh)
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TWI703933B (en
Inventor
Satoshi Fujiwara
Kenji Haraguchi
Yo FUKUMOTO
Hiroko Akao
Kazuya Kawabata
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T Hasegawa Co Ltd
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Publication of TW201733459A publication Critical patent/TW201733459A/en
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Publication of TWI703933B publication Critical patent/TWI703933B/en

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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L5/00Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20Synthetic spices, flavouring agents or condiments
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L27/00Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30Artificial sweetening agents
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23CDAIRY PRODUCTS, e.g. MILK, BUTTER OR CHEESE; MILK OR CHEESE SUBSTITUTES; MAKING THEREOF
    • A23C9/00Milk preparations; Milk powder or milk powder preparations
    • A23C9/152Milk preparations; Milk powder or milk powder preparations containing additives
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/32Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by the composition containing organic or inorganic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/44Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor characterised by shape, structure or physical form
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G9/00Frozen sweets, e.g. ice confectionery, ice-cream; Mixtures therefor
    • A23G9/52Liquid products; Solid products in the form of powders, flakes or granules for making liquid products ; Finished or semi-finished solid products, frozen granules

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Seasonings (AREA)
  • Dairy Products (AREA)
  • Confectionery (AREA)
  • General Preparation And Processing Of Foods (AREA)

Abstract

Adding, as an active ingredient to a food or beverage product, the compound represented by formula (1), which is a 4-alkoxycinnamaldehyde derivative, imparts or enhances a desired fragrance, e.g. spicy, waxy, fatty, green, or metallic. Adding said compound as an active ingredient to a food or beverage product also has the effect of imparting or enhancing sweetness. In formula (1), R represents a hydrocarbon group comprising 2 to 4 carbon atoms.

Description

以4-烷氧基桂皮醛衍生物為有效成分之香味調整劑Aroma adjuster with 4-alkoxycinaldehyde derivative as active ingredient

本發明係關於一種具有特異之香氣及甜味之以4-烷氧基桂皮醛等為有效成分之香味調整劑。更詳細而言,本發明係關於一種含有該化合物作為有效成分之飲食品用香料組合物(以下,亦稱為香料組合物)、以及調配該等香味調整劑或飲食品用香料組合物而成之飲食品。進而,本發明亦係關於一種使飲食品中含有該化合物之飲食品之香氣賦予或增強方法及飲食品之甜味賦予或增強方法。The present invention relates to a flavor adjuster which has a specific aroma and sweetness and which has an alkoxycin aldehyde and the like as an active ingredient. More specifically, the present invention relates to a flavor composition for foods and drinks containing the compound as an active ingredient (hereinafter also referred to as a flavor composition), and a flavor composition for blending the flavor adjuster or the food or beverage. Food and drink. Further, the present invention relates to a method for imparting or enhancing an aroma imparting or enhancing a food or drink containing the compound in a food or drink, and a method for imparting or enhancing a sweetness of the food or beverage.

近年來,於食品用香料中,隨著消費者之嗜好性之多樣化,對具有先前未有之新型香氣、香味之香料的需求提高,從而期望開發一種具有柔和且清新之香質,持續性優異之獨特之香料原材料。於此種背景下,正進行將香料原材料適當地且改變其調配量而加以組合,以儘可能具有天然性之方式進行調製之研究等,但可謂仍不充分。因此,作為新穎之香料原材料,正進行各種有機化合物之探索。 香料化合物係刺激嗅覺之化合物,其種類可謂數萬種。另一方面,認為飲食品之風味為嗅覺刺激與味覺刺激於腦中綜合而成之感覺。即,嗅覺刺激係將香料化合物等主要刺激嗅覺之化合物與主要刺激味覺之化合物(食鹽、砂糖、麩胺酸鈉等)組合,形成飲食品整體之風味。近年來,自具有香氣之化合物中,對刺激嗅覺同時刺激味覺之化合物積極進行探索,用於飲食品之綜合風味之提昇。 甜味係作為味道之基本要素之五味之一,成為可用於飲食品整體之風味形成之要素。包括甜味在內之五味係藉由被稱為味蕾(taste bud)之味細胞之集合體而感知,其係作為味覺刺激傳遞至腦而被感知。甜味作為味道改善之要素近年來受到關注,為了賦予或增強甜味,利用各種甜味劑。 先前,作為飲食品中使用之甜味劑,廣泛地利用砂糖(蔗糖)、葡萄糖、果糖等糖類。其中,尤其蔗糖具有極其優質之甜味,除此以外,亦具有可對飲食品賦予濃郁味或體感等之味道特性。而且,就保濕性、黏度之賦予、水分活性之降低等物性之方面而言亦優異。但是,蔗糖自古以來亦被認為係蟲牙之原因之一,又,近年來認為亦可能因過度攝取而成為生活習慣疾病之原因,故而根據最近之健康意向或低卡路里意向,有控制使用之傾向。尤其於飲料或點心等嗜好品中,該傾向較強,正推進低卡路里化之傾向。 應對此種一般消費者之需求傾向,用作代替蔗糖之甜味劑者係阿斯巴甜、蔗糖素、乙醯磺胺酸K、Advantame、糖精、糖精鈉、甜菊、甘草、紐甜等所謂「高甜度甜味劑」。該等高甜度甜味劑具有遠遠強於蔗糖之甜味,兼具藉由微量之添加而可對飲食品賦予甜味之作為「低卡路里甜味劑」之特徵。 然而,高甜度甜味劑大多甜味之品質之厚重感或濃郁味不足,又,具有苦味、澀味或刺激味等令人不愉快之味道對後味留下影響之所謂「殘餘感」。為了改善該等,必須另外藉由其他添加劑而改良苦味、澀味或刺激味等後味之令人不愉快之味道,故而現狀為如砂糖般一般消費者通常用於烹飪等之情況較少。 因此,期望一種不具有所謂「殘餘感」且低卡路里之甜味劑。 於香料化合物中,桂皮醛或4-甲氧基桂皮醛等係作為低卡路里且具有香味及甜味之化合物而已知(專利文獻1)。又,可見對甜味受體之作用(專利文獻2),可見與甜味物質之協同效應(專利文獻3)。然而,雖於後味方面不具有殘餘感,但與先前之高甜度甜味劑相比甜味較弱,故而進而謀求一種甜味較強之化合物。 [先前技術文獻] [專利文獻] [專利文獻1]美國專利3908028號公報 [專利文獻2]日本專利特開2011-116693號公報 [專利文獻3]日本專利特開2013-127377號公報In recent years, in the food flavors, with the diversification of consumer preference, the demand for fragrances having a new fragrance and fragrance that has not been previously increased has been desired, and it is desired to develop a soft and fresh fragrance and sustainability. Excellent unique spice raw materials. Under such a background, studies have been carried out in which the fragrance raw materials are appropriately combined and changed, and the preparation is carried out in such a manner as to be as natural as possible, but it is still insufficient. Therefore, as a novel fragrance raw material, various organic compounds are being explored. Flavor compounds are compounds that stimulate the sense of smell, and the types thereof are tens of thousands. On the other hand, it is considered that the flavor of food and beverage is a combination of olfactory stimulation and taste stimulation in the brain. In other words, the olfactory stimulation combines a compound which mainly stimulates the olfactory substance such as a fragrance compound with a compound which mainly stimulates the taste (salt, sugar, sodium glutamate, etc.) to form a flavor of the whole food and drink. In recent years, among the compounds having aroma, the compounds which stimulate the sense of smell and stimulate the taste have been actively explored for the improvement of the comprehensive flavor of foods and drinks. Sweetness is one of the five flavors of the basic elements of taste, and it is an element which can be used for the flavor formation of the whole food and drink. The five flavors, including sweetness, are perceived by a collection of taste cells called taste buds that are transmitted as a taste stimulus to the brain. Sweetness has been attracting attention as an element of taste improvement in recent years, and various sweeteners are used in order to impart or enhance sweetness. Conventionally, as a sweetener used in foods and drinks, sugars such as sucrose (sucrose), glucose, and fructose have been widely used. Among them, in particular, sucrose has an extremely high-quality sweetness, and has a taste characteristic which can impart a rich taste or a body sensation to foods and drinks. Further, it is excellent in terms of physical properties such as moisture retention, viscosity, and reduction in water activity. However, sucrose has been considered to be one of the causes of worms since ancient times. In recent years, it has been thought that it may become a cause of lifestyle-related diseases due to excessive intake. Therefore, according to recent health intentions or low-calorie intentions, there is a tendency to control use. In particular, in a hobby such as a beverage or a snack, this tendency is strong, and the tendency to promote low calorie is being promoted. In response to the demand of such general consumers, the sweeteners used to replace sucrose are aspartame, sucralose, acesulfame K, Advantame, saccharin, sodium saccharin, stevia, licorice, neotame, etc. High sweetness sweetener". These high-intensity sweeteners are characterized by being much stronger than the sweetness of sucrose and having a sweet taste added to foods and drinks by a small amount of addition, as a "low calorie sweetener". However, most of the high-intensity sweeteners have a thick or strong taste of sweetness, and have a so-called "residual feeling" which has an unpleasant taste such as bitterness, astringency or irritating taste which affects the aftertaste. In order to improve these, it is necessary to additionally improve the unpleasant taste of the aftertaste such as bitterness, astringency or irritating taste by other additives, and thus the current situation is such that sugar is generally used by consumers in general for cooking and the like. Therefore, a sweetener having no so-called "residual feeling" and low calorie is desired. Among the perfume compounds, cinnamaldehyde or 4-methoxycinnamaldehyde is known as a compound having a low calorie and having a flavor and a sweet taste (Patent Document 1). Further, it can be seen that the effect on the sweet receptor (Patent Document 2) can be seen as a synergistic effect with the sweet substance (Patent Document 3). However, although there is no residual sensation in the aftertaste, the sweetness is weaker than that of the previous high-intensity sweetener, and thus a compound having a strong sweetness is further desired. [PRIOR ART DOCUMENT] [Patent Document 1] Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei.

[發明所欲解決之問題] 本發明之目的在於提供一種香料化合物,其係於攝取時為低卡路里,具有足以用於飲食品之香味及甜味,進而不具有如高甜度甜味劑般之所謂「殘餘感」,於添加至飲食品中之情形時賦予或增強較佳之香氣,又,於添加至飲食品中之情形時,除香氣以外,亦賦予或增強甜味作為味道。又,本發明在於提供一種含有該化合物作為有效成分之香料組合物、以及含有該化合物作為有效成分之飲食品。再者,「賦予或增強」之用語中之「或」係與「及/或」同義。 [解決問題之技術手段] 本發明者等人對大量之有機化合物進行了努力探索,結果發現作為下述式(1)所表示之化合物之4-烷氧基桂皮醛衍生物具有辛香、蠟香、脂肪香、綠色調、類金屬味等香氣,又,於調配至飲食品中之情形時,具有不具有苦味、澀味或刺激味而賦予或增強較佳之香氣,賦予或增強飲食品之甜味之效果,甜味之增強效果與4-甲氧基桂皮醛相比大幅增大,從而完成了本發明。 如此,本發明提供以下者。 (a)一種香味調整劑,其係以下述式(1)所表示之化合物為有效成分。 [化1]上述式(1)中,R表示碳數2至4之烴基。 (b)如(a)之香味調整劑,其中香味調整係香氣之賦予或增強。 (c)如(a)之香味調整劑,其中香味調整係甜味之賦予或增強。 (d)一種飲食品用香料組合物,其含有如(a)至(c)中任一項之香味調整劑作為有效成分。 (e)一種飲食品,其含有如(a)至(c)中任一項之香味調整劑或如(d)之飲食品用香料組合物。 (f)一種飲食品之香氣賦予或增強方法,其係使飲食品中含有如(a)之式(1)所表示之化合物。 (g)一種飲食品之甜味賦予或增強方法,其係使飲食品中含有如(a)之式(1)所表示之化合物。 [發明之效果] 作為上述式(1)所表示之化合物之4-烷氧基桂皮醛衍生物具有辛香、蠟香、脂肪香、綠色調、類金屬味等香氣,又,於調配至飲食品中之情形時,不具有苦味、澀味或刺激味,具有賦予或增強飲食品之甜味之效果。[Problem to be Solved by the Invention] An object of the present invention is to provide a perfume compound which is low in calories when ingested, has a flavor and sweetness sufficient for use in foods and drinks, and thus does not have a sweetener such as a high-intensity sweetener. The "residual feeling" imparts or enhances a preferred aroma when added to foods and drinks, and also imparts or enhances sweetness as a taste in addition to aroma when added to foods and drinks. Moreover, the present invention provides a flavoring composition containing the compound as an active ingredient, and a food or drink containing the compound as an active ingredient. Furthermore, the word "or" in the term "give or enhance" is synonymous with "and/or". [Means for Solving the Problem] The inventors of the present invention have conducted an effort to investigate a large number of organic compounds, and as a result, it has been found that a 4-alkoxycinaldehyde derivative which is a compound represented by the following formula (1) has a scent and a wax. Aromas such as fragrant, fatty, green, and metallic, and when formulated into foods and beverages, have a bitter, astringent or pungent odor to impart or enhance a better aroma, to impart or enhance food and drink. The sweet taste effect and the sweetness enhancing effect are greatly increased as compared with 4-methoxycinnamic aldehyde, thereby completing the present invention. Thus, the present invention provides the following. (a) A flavor adjuster which is a compound represented by the following formula (1) as an active ingredient. [Chemical 1] In the above formula (1), R represents a hydrocarbon group having 2 to 4 carbon atoms. (b) A flavor conditioner according to (a), wherein the flavor adjustment is imparted or enhanced by the aroma. (c) A flavor conditioner according to (a), wherein the flavor adjustment is imparted or enhanced by the sweetness. (d) A flavor composition for foods and drinks comprising the flavor adjuster according to any one of (a) to (c) as an active ingredient. (e) A food or drink comprising the flavor adjuster according to any one of (a) to (c) or the flavor composition for foods and drinks according to (d). (f) A method for imparting or enhancing an aroma of a food or drink, which comprises a compound represented by the formula (1) (a) in a food or drink. (g) A sweetness imparting or enhancing method for a food or drink comprising a compound represented by the formula (1) (a) in a food or drink. [Effects of the Invention] The 4-alkoxycinaldehyde derivative of the compound represented by the above formula (1) has aromas such as spice, wax, fat, green, and metal-like flavor, and is formulated into a diet. In the case of the product, it does not have a bitter taste, astringency or a pungent taste, and has the effect of imparting or enhancing the sweetness of the food and drink.

以下,對本發明更詳細地進行說明。 如上所述,作為上述式(1)所表示之化合物之4-烷氧基桂皮醛衍生物具有辛香、蠟香、脂肪香、綠色調、類金屬味等香氣,又,於調配至飲食品中之情形時,具有不具有苦味、澀味或刺激味而賦予或增強飲食品之甜味之效果。再者,上述式(1)所表示之化合物較佳為於調配至飲食品中之情形時不具有其他雜味。 [化2]上述式(1)中,R表示碳數2至4之烴基。 R較佳為碳數2至4之烷基或碳數2至4之伸烷基。尤其於上述式(1)中,R為碳數2至4之烷基之情形時,具有賦予或增強飲食品之甜味之效果。 作為具體之化合物,可列舉:4-乙氧基桂皮醛、4-丙氧基桂皮醛、4-異丙氧基桂皮醛、4-(2-丙烯氧基)桂皮醛、4-丁氧基桂皮醛、4-異丁氧基桂皮醛、4-(第二丁氧基)桂皮醛、4-(第三丁氧基)桂皮醛、4-(3-丁烯氧基)桂皮醛。進而,該等化合物具有賦予或增強飲食品之甜味之效果。 例如,關於4-乙氧基桂皮醛,其為公知化合物,於日本專利第3959964號中記載為天冬胺醯二肽酯衍生物之合成原料。然而,於日本專利第3959964號中未記載香味或甜味等效果。 又,關於4-異丙氧基桂皮醛,其亦為公知化合物,例如於日本專利第3300869號中記載為5-[3-[4-(5-甲基-2-苯基-4-噻唑基甲氧基)苯基]丙基]-2,4-㗁唑啶二酮之合成中間物。然而,於日本專利第3300869號中未記載香味或甜味等效果。 關於4-烷氧基桂皮醛,可利用日本專利特表2000-507227號中所記載之合成反應而製備。即,藉由使用路易斯酸觸媒使4-烷氧基苯甲醛二甲基縮醛(2)與甲基乙烯基醚(3)進行反應而生成化合物(4),將該化合物進行水解,藉此獲得4-烷氧基桂皮醛(1)。 [化3]該等所獲得之化合物亦可藉由使用減壓蒸餾或管柱層析等方法而進行高純度化。 本發明係一種特徵在於以上述式(1)所表示之4-烷氧基桂皮醛為有效成分之香味調整劑(較佳為香氣賦予或增強劑、甜味賦予或增強劑)、及含有該化合物作為有效成分之飲食品用香料組合物、以及含有該等之飲食品。 作為本發明之香味調整劑等之有效成分之上述式(1)所表示之化合物具有辛香、蠟香、脂肪香、綠色調、類金屬味的香氣,於以香氣賦予為目的而使用上述式(1)所表示之化合物之情形時,相對於飲食品,以質量基準計,作為上述式(1)所表示之化合物,可於一般為1 ppm~10000 ppm、較佳為5 ppm~5000 ppm、更佳為10 ppm~5000 ppm之範圍內添加。藉由於該濃度範圍內添加,可對飲食品賦予香氣。 又,上述式(1)所表示之化合物係於單獨使用之情形時,或者於與蔗糖等甜味物質併用之情形時,具有甜味賦予或增強作用,發揮該效果之濃度係以飲食品之質量作為基準,為1 ppm~10000 ppm、較佳為5 ppm~5000 ppm、更佳為10 ppm~5000 ppm之範圍。 作為上述式(1)所表示之化合物藉由協同效應而增強甜味之呈味原材料,可例示:蔗糖(砂糖)、葡萄糖、果糖、麥芽糖、乳糖、半乳糖、麥芽糖、海藻糖等糖類;乙醯磺胺酸K、蔗糖素、阿斯巴甜、Advantame、紐甜、甘草酸二鈉、索馬甜、糖精及其鹽、羅漢果萃取物、甘草萃取物、瑞鮑迪甙A、甜菊萃取物、酵素處理甜菊萃取物、新橙皮苷雙氫查耳酮等高甜度甜味劑類;木糖醇、赤藻糖醇、山梨醇、麥芽糖醇、Palatinit、還原飴糖等糖醇類;及該等之任意之混合物等。 於將上述式(1)所表示之化合物添加至飲食品中時,亦可將上述式(1)所表示之化合物本身或本身之稀釋液添加至飲食品中。又,可製備含有上述式(1)所表示之化合物作為有效成分之香料組合物,將該香料組合物添加至飲食品中,藉此對飲食品賦予香氣。又,藉由對飲食品賦予香氣,且使香料組合物中含有上述式(1)所表示之化合物作為有效成分,將該香料組合物添加至飲食品中,可對飲食品增強甜味。 本發明之香料組合物可以該香料組合物之質量作為基準,以一般為1000 ppm~20%、較佳為2000 ppm~10%、更佳為5000 ppm~5%之濃度含有上述式(1)所表示之化合物。 進而,於對飲食品賦予香氣之情形時,可添加0.01%~1%左右之該香料組合物,作為上述式(1)所表示之化合物對飲食品之添加濃度,以將質量作為基準而成為1 ppm~10000 ppm、較佳為5 ppm~5000 ppm、更佳為10 ppm~5000 ppm之範圍之方式添加至該飲食品中。其結果為,上述式(1)所表示之化合物作為有效成分對飲食品發揮作用,可對飲食品賦予辛香、蠟香、脂肪香、綠色調、類金屬味等香氣。 又,於對飲食品增強甜味之情形時,可添加0.01%~1%左右之該香料組合物,作為上述式(1)所表示之化合物對飲食品之添加濃度,以將該飲食品之質量作為基準而成為1 ppm~10000 ppm、較佳為5 ppm~5000 ppm、更佳為10 ppm~5000 ppm之範圍之方式添加。其結果為,上述式(1)所表示之化合物可作為有效成分發揮作用,可對飲食品增強飲食品之甜味。 於上述式(1)所表示之化合物對飲食品之添加濃度為1 ppm以上之情形時,對飲食品之香氣賦予效果或對飲食品之甜味之增強效果變強,又,若上述式(1)所表示之化合物對飲食品之添加濃度為10000 ppm以下,則飲食品中之本化合物獨特之香氣不會過強,從而較佳。又,飲食品之味道之平衡性不會破壞,從而較佳。 於上述香料組合物中,除上述式(1)所表示之化合物以外,亦可調配一般可使用之其他香料成分。作為可與上述式(1)所表示之化合物一起含有之其他香料成分,可列舉各種合成香料、天然香料、天然精油、動植物萃取物等。作為其他香料成分,可列舉「日本專利廳,周知慣用技術集(香料)第II部食品香料,8-87頁,2000年1月14日發行」中所記載之合成香料、天然精油、天然香料、動植物萃取物等。 作為該等其他香料成分,可列舉飲食品用香料之原材料及各種萃取物。作為飲食品用香料之原材料,例如可列舉:作為烴化合物之α-蒎烯、β-蒎烯、月桂烯、莰烯、檸檬烯等單萜,朱欒倍半萜、雪松烯、石竹烯、長葉烯等倍半萜,1,3,5-十一烷三烯等不飽和烴;作為醇化合物之丁醇、戊醇、己醇、辛醇等直鏈、飽和烷醇類,異戊烯醇、(Z)-3-己烯醇、2,6-壬二烯醇、(Z)-6-壬烯醇等直鏈、不飽和醇類,沉香醇、香葉草醇、橙花醇、香茅醇、四氫月桂烯醇、月桂烯醇、金合歡醇、橙花叔醇、雪松醇等萜烯醇類,苄醇、苯基乙基醇等芳香族醇類;作為醛化合物之乙醛、丁醛、戊醛、己醛、辛醛、癸醛等直鏈、飽和醛,(E)-2-己烯醛、(Z)-3-己烯醛、2,4-辛二烯醛、(Z)-6-壬烯醛等直鏈、不飽和醛類,香茅醛、檸檬醛等萜烯醛,苯甲醛、桂皮醛、香蘭素、乙香草醛、向日花香醛等芳香族醛類;作為酮化合物之2-庚酮、2-己酮、2-辛酮、2-十一酮、1-辛烯-3-酮等直鏈、飽和及不飽和酮類,乙偶姻、雙乙醯、2,3-戊二酮等直鏈二酮類,香旱芹酮、薄荷酮、花柏酮等萜烯酮類,α-紫羅蘭酮、β-紫羅蘭酮、β-突厥烯酮等源自萜烯分解物之酮類,覆盆子酮等芳香族酮類;作為呋喃、醚化合物之糠醇、糠醛、葫蘆巴內酯、醬油酮、2,5-二甲基-4-羥基-3(2H)-呋喃酮、5-乙基-3-羥基-4-甲基-2(5H)-呋喃酮等呋喃類,麥芽醇、乙基麥芽醇等吡喃類,玫瑰醚、氧化芳樟醇、薄荷呋喃、茶螺烷等環狀醚類;作為酯化合物之乙酸乙酯、乙酸異戊酯等脂肪族醇之乙酸酯類,乙酸沉香酯、乙酸香葉酯、乙酸薰衣草酯等萜烯醇乙酸酯類,丁酸乙酯、己酸乙酯等脂肪酸與低級醇酯類,乙酸苄酯、水楊酸甲酯等芳香族酯類;作為內酯化合物之γ-辛內酯、γ-壬內酯、γ-癸內酯、γ-十一內酯、γ-十二內酯、δ-辛內酯、δ-壬內酯、δ-癸內酯、δ-十一內酯、δ-十二內酯等飽和內酯類,7-癸烯-4-交酯、2-癸烯-5-交酯等不飽和內酯類;作為酸化合物之丁酸、戊酸、異戊酸、己酸、辛酸、癸酸、月桂酸、肉豆蔻酸、硬脂酸、油酸、亞麻油酸、次亞麻油酸等飽和、不飽和脂肪酸類;作為含氮化合物之吲哚、糞臭素、吡啶、烷基取代吡𠯤、鄰胺苯甲酸甲酯等;作為含硫化合物之甲硫醇、二甲基硫醚、二甲基二硫醚、異硫氰酸烯丙酯等。又,亦可列舉:作為各種萃取物之草本香料萃取物,咖啡、綠茶、紅茶、烏龍茶萃取物,乳或乳加工品及該等之脂肪酶、蛋白酶等酵素分解物。 又,於上述香料組合物中,可視需要調配作為香料組合物中通常使用之保持劑之水、乙醇等溶劑或乙二醇、1,2-丙二醇、甘油、苯甲酸苄酯、檸檬酸三乙酯、氫化松香酸甲酯、脂肪酸甘油三酯、脂肪酸甘油二酯等。 又,亦可於上述香料組合物中,調配例如皂樹萃取物、酵素處理卵磷脂、蔗糖脂肪酸酯、聚甘油脂肪酸酯、甘油脂肪酸酯、阿拉伯膠等乳化劑及/或穩定劑之1種以上,使用例如均質混合機、膠體磨機、高壓均質機等進行乳化,藉此製成乳化香料製劑之形態。乳化劑及/或穩定劑之使用量根據乳化劑及/或穩定劑之種類等而不同,例如以乳化香料製劑之質量作為基準,可列舉0.1~25重量%之範圍、較佳為5~20重量%之範圍內。 進而,例如亦可於上述乳化香料製劑中適當調配砂糖、乳糖、葡萄糖、海藻糖、纖維雙糖、飴糖、還原飴糖等糖類;糖醇類;糊精等各種澱粉分解物及澱粉衍生物、澱粉、明膠、阿拉伯膠等天然膠類等賦形劑後,藉由例如噴霧乾燥、真空乾燥等適當之乾燥方法進行乾燥而製成粉末香料製劑之形態。該等賦形劑之調配量可根據粉末香料製劑所需之特性等而適當地選擇。 作為藉由單獨使用上述式(1)所表示之化合物,或者藉由使用以上述式(1)所表示之化合物為有效成分之香料組合物,可增強辛香、蠟香、脂肪香、綠色調、類金屬味之香氣,且不具有苦味、澀味或刺激味而增強甜味之飲食品之具體例,可列舉:可樂飲料、含果汁碳酸飲料、含乳類碳酸飲料、薑汁汽水、蘋果汁等碳酸飲料類;果汁飲料、蔬菜飲料、運動飲料、蜂蜜飲料、豆乳、維生素補充飲料、礦物質補充飲料、營養飲料、滋養飲料、乳酸菌飲料、乳飲料等軟飲料類;綠茶、紅茶、烏龍茶、花草茶、奶茶、可可飲料、咖啡飲料等嗜好飲料類;摻蘇打水燒酒、雞尾酒飲料、發泡酒、水果酒、藥用酒等酒精飲料類;黃油、乳酪、牛奶、酸乳酪等乳製品;冰淇淋、乳酸冰淇淋、雪酪、布丁、果凍、奶油凍、日常甜點等甜點類及用以製造該等之混料粉類;焦糖、糖果、模壓點心、口香糖、軟糖、脆餅乾、餅乾、曲奇、派、巧克力、休閒點心等點心類及用以製造該等之蛋糕混料粉等混料粉類;水果風味醬或巧克力醬等醬類;奶油淇淋或鮮乳油等乳油類;草莓醬或橘皮果醬等果醬;麵包、湯、各種速食食品等一般食品類;牙膏等口腔用組合物。 [實施例] 以下,藉由實施例更具體地說明本發明,但本發明並不限定於該等。於實施例中,只要未特別說明,則記載為「%」者係以質量為基準。 實施例1:4-烷氧基桂皮醛之香氣評價 按照日本專利特表2000-507227號中所記載之合成反應而製備4-乙氧基桂皮醛(本發明品1)及4-異丙氧基桂皮醛(本發明品2),製備該等之1%乙醇溶液作為香氣評價之評價液。於樣本瓶中準備評價液,進行自瓶口之香氣評價,及藉由含浸有評價液之香味紙由受過良好訓練之5名官能檢查員進行香氣評價。將其平均評價示於下述表1。根據下述表1可知具有辛香、蠟香、脂肪香、綠色調、類金屬味等香氣。 [表1] 實施例2:草莓狀之調製香料組合物 根據下述表2之配方,調製草莓狀之調製香料組合物。 [表2] 於上述草莓狀香料組合物(比較品1)98.0 g中混合2.0 g(2.0質量%)之本發明品1或2而製備新穎之草莓狀之調製香料組合物。將於比較品1中混合有本發明品1者作為本發明品3,將於比較品1中混合有本發明品2者作為本發明品4。由5名專業官能檢查員對本發明品3或4及比較品1進行比較。香氣評價係於樣本瓶(30 ml)中準備香料組合物10 ml,進行自瓶口之香氣評價,及藉由含浸有香料組合物之香味紙由受過良好訓練之5名專業官能檢查員進行比較。其結果為,5名專業官能檢查員全部捕捉到本發明品3或4與比較品1相比均為新鮮之草莓之特徵,又,就持續性之方面而言亦尤其優異。即,確認到藉由使飲食品中含有本發明品1或2之香味調整劑,可賦予或增強飲食品之香氣。又,亦確認到本發明品3或4不具有苦味、澀味或刺激味,不具有所謂「殘餘感」。 實施例3:草莓狀之調製香料組合物於雪酪中之調配 將實施例2中所獲得之草莓狀調製香料組合物(比較品1或本發明品3)添加至下述雪酪調配配方之雪酪中,藉由常規方法製備雪酪,由受過良好訓練之5名官能檢查員食用,進行官能評價。 雪酪調配配方(質量份) 砂糖:10、 飴糖(75%):6、 果糖葡萄糖液糖(75%):5、 檸檬酸(結晶):0.1、 1/5草莓果汁(20質量%草莓果汁):10、 本發明品3(或比較品1):0.2, 藉由水使合計量為100。 由5名官能檢查員對該等雪酪進行官能評價。其結果為,5名官能檢查員全部評價為添加有本發明品3之雪酪與添加有比較品1之雪酪相比,加強新鮮之草莓之特徵,關於味道,亦甜味較強。又,亦確認到添加有本發明品3之雪酪不具有苦味、澀味或刺激味,不具有所謂「殘餘感」。 實施例4:甜味之確認 將4-乙氧基桂皮醛(本發明品1)及4-異丙氧基桂皮醛(本發明品2)稀釋於乙醇中而製成10質量%乙醇溶液,藉由水將其進行稀釋而製備溶解有下述表3所示之濃度之本發明品1及2之溶液。又,藉由與本發明品1及2相同之方法稀釋作為比較品之4-甲氧基桂皮醛(比較品2),製備下述表3所示之濃度之溶液。將無添加之水作為對照品,由受過良好訓練之10名官能檢查員品嘗溶解有本發明品1、2及比較品2之溶液,藉此進行對甜味之官能評價。 甜味評分係將水作為對照品,以0:與對照品相比無變化、1:與對照品相比稍微感覺到甜味、2:與對照品相比感覺到甜味、3:與對照品相比強烈地感覺到甜味、4:甜味過強故而味道之平衡性較差而進行評分。將10名該官能檢查員之平均分示於下述表3。 [表3] 如上述表3所示,於將本發明品1及2之10質量%乙醇溶液稀釋於水中之情形時,該水溶液具有甜味。又,可知作為其濃度,以質量作為基準,於10 ppm~5000 ppm之範圍內感覺到甜味,尤其於25 ppm~1000 ppm左右感覺到良好之甜味。 另一方面,於將比較品2之10質量%乙醇溶液稀釋於水中之情形時,該水溶液亦具有甜味。又,可知作為其濃度,以質量作為基準,於50 ppm~10000 ppm之範圍內感覺到甜味,尤其於100 ppm~5000 ppm左右感覺到良好之甜味。 實施例5:與砂糖水溶液之比較 藉由與實施例4相同之方法,製備本發明品1、2及比較品2之50 ppm水溶液,又,另外以每0.5質量%準備1~10質量%之砂糖水溶液。由受過良好訓練之10名官能檢查員判定本發明品1、2及比較品2之50 ppm水溶液為與1~10質量%之砂糖水溶液中之哪一者同等的甜度。將其結果示於下述表4。 [表4] 根據上述表4之結果可知,與比較品2相比,本發明品1及2具有更強之甜味。關於比較品2,亦存在評價為低於砂糖水溶液1質量%之濃度之官能檢查員。又,亦證實本發明品1及2與砂糖相比以1/200~1/1000左右之低濃度具有甜味。 實施例6:甜味增強效果之確認 由受過良好訓練之5名官能檢查員品嘗3質量%砂糖水溶液、及於其中加入有50 ppm之本發明品1及2之砂糖水溶液,藉此進行對甜味之官能評價。其結果為,5名全部評價為加入有50 ppm之本發明品1及2之砂糖水溶液與3質量%砂糖水溶液相比甜味較強。 實施例7:橙汁之甜味增強 獲得於市售之果汁100%之橙汁中以成為50 ppm之方式添加有本發明品1及2之橙汁。由受過良好訓練之5名官能檢查員品嘗該等,藉此進行對甜味之官能評價。其結果為以成為50 ppm之方式添加有本發明品1及2之橙汁與無添加之果汁100%之橙汁相比甜味較強的評價。 實施例8:加糖牛乳之甜味評價 如以下之表5所示,於加糖牛乳基材中調配本發明品1、2及比較品2之10質量%乙醇溶液,製備加糖牛乳。關於加糖牛乳,將無添加品作為參考品1,將調配有本發明品1者作為本發明品5,將調配有本發明品2者作為本發明品6,將調配有比較品2者作為比較品3。 [表5] 對於藉由上述方法所製備之加糖牛乳,以參考品1作為對照(對照品),由10名受過良好訓練之官能檢查員進行甜味評價。甜味評價係藉由試飲參考品1、本發明品5、6及比較品3進行評價。甜味評分係與參考品1相比,以-1:甜味劣化、0:無顯著差別、1:甜味稍強、2:甜味較強、3:甜味明顯較強而進行評分。將10名官能檢查員之平均分示於下述表6。 [表6] 根據上述表6之結果顯示,於加糖牛乳(基材)中添加有本發明品1及2之本發明品5及6有增強加糖牛乳之甜味之效果,因此,表現出本發明品1及2之甜味增強效果。另一方面,顯示於加糖牛乳(基材)中添加有比較品2之比較品3幾乎不存在增強加糖牛乳之甜味之效果。Hereinafter, the present invention will be described in more detail. As described above, the 4-alkoxycinaldehyde derivative which is a compound represented by the above formula (1) has aromas such as spice, wax, fat, green, and metal-like flavor, and is formulated into foods and drinks. In the case of the case, there is an effect of imparting or enhancing the sweetness of the food or drink without having a bitter taste, astringency or a pungent taste. Further, the compound represented by the above formula (1) preferably has no other odor when it is formulated into a food or beverage. [Chemical 2] In the above formula (1), R represents a hydrocarbon group having 2 to 4 carbon atoms. R is preferably an alkyl group having 2 to 4 carbon atoms or an alkylene group having 2 to 4 carbon atoms. Particularly, in the case of the above formula (1), when R is an alkyl group having 2 to 4 carbon atoms, it has an effect of imparting or enhancing the sweetness of foods and drinks. Specific examples of the compound include 4-ethoxycinnamaldehyde, 4-propoxycinnamic aldehyde, 4-isopropoxycinnamic aldehyde, 4-(2-propenyloxy)cinnamaldehyde, and 4-butoxy group. Cinnamaldehyde, 4-isobutoxycinnaaldehyde, 4-(second butoxy)cinnamaldehyde, 4-(t-butoxy)cinnamaldehyde, 4-(3-butoxy)cinnamaldehyde. Further, these compounds have an effect of imparting or enhancing the sweetness of foods and drinks. For example, 4-ethoxycinsanaldehyde, which is a known compound, is described as a synthetic raw material of an aspartame dipeptide ester derivative in Japanese Patent No. 3959964. However, effects such as flavor or sweetness are not described in Japanese Patent No. 3959964. Further, regarding 4-isopropoxy cinnamaldehyde, it is also a known compound, and is described, for example, in Japanese Patent No. 3300869 as 5-[3-[4-(5-methyl-2-phenyl-4-thiazole). A synthetic intermediate of methoxy)phenyl]propyl]-2,4-oxazolidinone. However, effects such as flavor or sweetness are not described in Japanese Patent No. 3300869. The 4-alkoxycinnaaldehyde can be produced by the synthesis reaction described in JP-A-2000-507227. That is, the compound (4) is produced by reacting 4-alkoxybenzaldehyde dimethyl acetal (2) with methyl vinyl ether (3) by using a Lewis acid catalyst, and the compound is hydrolyzed. This gave 4-alkoxycinnaaldehyde (1). [Chemical 3] These obtained compounds can also be purified by using a method such as vacuum distillation or column chromatography. The present invention is a flavor adjusting agent (preferably an aroma imparting or reinforcing agent, a sweetness imparting or reinforcing agent) characterized by using 4-alkoxycinnamaldehyde represented by the above formula (1) as an active ingredient, and containing the same A flavoring composition for foods and drinks containing a compound as an active ingredient, and a food or drink containing the same. The compound represented by the above formula (1), which is an active ingredient of the flavoring agent of the present invention, has a fragrance of a scent, a waxy, a fatty, a green, a metallic-like flavor, and the above formula is used for the purpose of imparting aroma. In the case of the compound represented by the above formula (1), the compound represented by the above formula (1) may be generally 1 ppm to 10000 ppm, preferably 5 ppm to 5000 ppm, based on the mass of the food or drink. More preferably, it is added in the range of 10 ppm to 5000 ppm. By adding in this concentration range, it is possible to impart aroma to foods and drinks. In addition, when the compound represented by the above formula (1) is used alone or in combination with a sweetener such as sucrose, it has a sweet taste imparting or enhancing effect, and the concentration at which the effect is exerted is a food or beverage. The mass is used in the range of 1 ppm to 10,000 ppm, preferably 5 ppm to 5000 ppm, more preferably 10 ppm to 5000 ppm. Examples of the taste-reducing raw material which enhances the sweetness by the synergistic effect of the compound represented by the above formula (1) include sucrose (sucrose), glucose, fructose, maltose, lactose, galactose, maltose, trehalose and the like; Sulfonamide K, sucralose, aspartame, Advantame, neotame, disodium glycyrrhizinate, thaumatin, saccharin and its salts, mangosteen extract, licorice extract, rebaudioside A, stevia extract, Enzyme treatment of stevia extract, high-sweetness sweeteners such as neohesperidin dihydrochalcone; sugar alcohols such as xylitol, erythritol, sorbitol, maltitol, Palatinit, reduced saccharides; Any mixture of the like, etc. When the compound represented by the above formula (1) is added to a food or beverage, the compound itself represented by the above formula (1) or a dilution thereof may be added to the food or beverage. Further, a perfume composition containing the compound represented by the above formula (1) as an active ingredient can be prepared, and the flavor composition can be added to a food or drink to impart aroma to the food or beverage. Moreover, by adding a fragrance to a food or drink, and including a compound represented by the above formula (1) as an active ingredient in the flavor composition, the flavor composition can be added to a food or drink to enhance the sweetness of the food or beverage. The flavor composition of the present invention may contain the above formula (1) at a concentration of usually from 1000 ppm to 20%, preferably from 2,000 ppm to 10%, more preferably from 5,000 ppm to 5%, based on the mass of the perfume composition. The compound represented. Furthermore, when aroma is added to a food or drink, the flavor composition may be added in an amount of from 0.01% to 1%, and the concentration of the compound represented by the above formula (1) to the food or drink is determined based on the mass. It is added to the food or drink in a range of 1 ppm to 10000 ppm, preferably 5 ppm to 5000 ppm, more preferably 10 ppm to 5000 ppm. As a result, the compound represented by the above formula (1) acts as an active ingredient on foods and drinks, and can impart aromas such as spice, wax, fat, green, and metal-like flavor to foods and drinks. Further, when the food or beverage is to enhance the sweetness, the flavor composition may be added in an amount of from 0.01% to 1%, and the concentration of the compound represented by the above formula (1) to the food or beverage may be added to the food or beverage. The mass is added so as to be in the range of 1 ppm to 10000 ppm, preferably 5 ppm to 5000 ppm, and more preferably 10 ppm to 5000 ppm. As a result, the compound represented by the above formula (1) can function as an active ingredient, and can enhance the sweetness of foods and drinks for foods and drinks. When the concentration of the compound represented by the above formula (1) is 1 ppm or more in the food or drink, the effect of imparting aroma to the food or beverage or enhancing the sweetness of the food or beverage is enhanced, and if the above formula ( 1) When the concentration of the compound to be added to the food or drink is 10000 ppm or less, the unique aroma of the compound in the food or drink is not too strong, which is preferable. Moreover, the balance of the taste of foods and drinks is not deteriorated, and thus it is preferable. In the above perfume composition, in addition to the compound represented by the above formula (1), other perfume components which can be generally used may be blended. Examples of the other perfume component which can be contained together with the compound represented by the above formula (1) include various synthetic perfumes, natural flavors, natural essential oils, animal and plant extracts, and the like. As other perfume ingredients, synthetic perfumes, natural essential oils, and natural flavors described in "Japanese Patent Office, Known Conventional Technology Set (Spices) Part II Food Flavor, 8-87 pages, issued on January 14, 2000" are exemplified. , animal and plant extracts, etc. Examples of the other flavor components include raw materials for flavors for foods and drinks and various extracts. Examples of the raw material of the food and drink flavor include a monoterpene such as α-pinene, β-pinene, myrcene, decene, and limonene as a hydrocarbon compound, valencene, cedarene, caryophyllene, and long leaves. An alicyclic oxime, an unsaturated hydrocarbon such as 1,3,5-undecanetriene; a linear, saturated alkanol such as butanol, pentanol, hexanol or octanol as an alcohol compound, and isopentenol , (Z)-3-hexenol, 2,6-decadienol, (Z)-6-nonenol, and other linear, unsaturated alcohols, linalool, geranyl alcohol, nerol, a decyl alcohol such as citronellol, tetrahydromyrcenol, myrcenol, farnesol, nerolidol, cedarol, an aromatic alcohol such as benzyl alcohol or phenylethyl alcohol; Linear, saturated aldehydes such as aldehyde, butyraldehyde, valeraldehyde, hexanal, octanal, furfural, (E)-2-hexenal, (Z)-3-hexenal, 2,4-octadiene Linear or unsaturated aldehydes such as aldehyde and (Z)-6-nonenal, decyl aldehyde such as citronellal or citral, benzaldehyde, cinnamaldehyde, vanillin, ethamaldehyde, and fragrant aldehyde Group aldehydes; 2-heptanone, 2-hexanone, 2-octanone, 2-111 as a ketone compound Linear, saturated and unsaturated ketones such as ketone and 1-octene-3-one, linear diketones such as acetoin, diacetyl or 2,3-pentanedione, fragrant ketone and menthone And ketones such as cedarone, ketones derived from terpene decomposition products such as ketones such as α-ionone, β-ionone, and β-thionone, and aromatic ketones such as raspberry ketone; Sterol, furfural, fenugreek lactone, soy sauce, 2,5-dimethyl-4-hydroxy-3(2H)-furanone, 5-ethyl-3-hydroxy-4-methyl-2 (5H a furan such as furanone, a pyran such as maltol or ethyl maltitol, a cyclic ether such as rose ether, linalool, menthylfuran or spiroxane; and ethyl acetate as an ester compound; An acetate of an aliphatic alcohol such as isoamyl acetate; a terpene acetate acetate such as agar resin, geranyl acetate or lavender acetate; a fatty acid such as ethyl butyrate or ethyl hexanoate; and a lower alcohol ester. An aromatic ester such as benzyl acetate or methyl salicylate; γ-octanolactone, γ-decalactone, γ-decalactone, γ-undecalactone, γ-twelfene as a lactone compound Ester, δ-octanolactone, δ-decalactone, δ-癸Saturated lactones such as ester, δ-undecalactone, δ-dodecanolactone, unsaturated lactones such as 7-nonene-4-lactide and 2-decene-5-lactide; Saturated and unsaturated fatty acids such as butyric acid, valeric acid, isovaleric acid, caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, stearic acid, oleic acid, linoleic acid, and linoleic acid; Nitrogen-containing compound strontium, skatole, pyridine, alkyl-substituted pyridyl-#134116; methyl ortho-benzoate; etc.; as a sulfur-containing compound, methyl mercaptan, dimethyl sulfide, dimethyl disulfide , allyl isothiocyanate and the like. Further, examples thereof include herbal extracts of various extracts, coffee, green tea, black tea, oolong tea extract, milk or milk processed products, and enzyme decomposition products such as lipases and proteases. Further, in the above-mentioned perfume composition, water, ethanol or the like, or ethylene glycol, 1,2-propanediol, glycerin, benzyl benzoate or triethyl citrate, which is a commonly used retaining agent in the perfume composition, may be blended as needed. Ester, methyl hydrogenated rosinate, fatty acid triglyceride, fatty acid diglyceride, and the like. Further, an emulsifier such as a soap tree extract, an enzyme-treated lecithin, a sucrose fatty acid ester, a polyglycerin fatty acid ester, a glycerin fatty acid ester, or a gum arabic, and/or a stabilizer may be blended in the above-mentioned flavor composition. One type or more is emulsified by, for example, a homomixer, a colloid mill, a high-pressure homogenizer, or the like, thereby preparing a emulsified flavor preparation. The amount of the emulsifier and/or the stabilizer to be used varies depending on the type of the emulsifier and/or the stabilizer, and the like, for example, in the range of 0.1 to 25% by weight, preferably 5 to 20, based on the mass of the emulsified fragrance preparation. Within the range of % by weight. Further, for example, sugars such as granulated sugar, lactose, glucose, trehalose, cellobiose, sucrose, and reduced sucrose may be appropriately blended in the emulsified flavor preparation; sugar alcohols; various starch decomposition products such as dextrin, starch derivatives, and starch. An excipient such as a natural gum such as gelatin or gum arabic is dried by a suitable drying method such as spray drying or vacuum drying to prepare a powder flavor preparation. The blending amount of the excipients can be appropriately selected depending on the properties and the like required for the powder flavor preparation. The fragrance composition, the waxy fragrance, the fatty fragrance, and the green tone can be enhanced by using the compound represented by the above formula (1) alone or by using the fragrance composition containing the compound represented by the above formula (1) as an active ingredient. Specific examples of foods and beverages which have a bitter taste, astringent taste or a pungent taste and enhance sweetness include cola drinks, juice-containing carbonated drinks, milk-containing carbonated drinks, ginger ale, and apples. Carbonated drinks such as juice; fruit drinks, vegetable drinks, sports drinks, honey drinks, soy milk, vitamin supplement drinks, mineral supplement drinks, nutritional drinks, nourishing drinks, lactic acid bacteria drinks, milk drinks, etc.; green tea, black tea, oolong tea, Herbal teas, milk tea, cocoa drinks, coffee drinks and other hobby drinks; mixed soda shochu, cocktail drinks, sparkling wine, fruit wine, medicinal wine and other alcoholic beverages; butter, cheese, milk, yogurt and other dairy products; Desserts such as ice cream, lactic acid ice cream, sorbet, pudding, jelly, custard, daily dessert, etc. and the powder used to make the same; caramel Confectionery, such as candy, molded snacks, chewing gum, soft candy, crackers, biscuits, cookies, pies, chocolates, snacks, etc., and blended powders used to make these cake mixes; fruit-flavored sauces or chocolate sauces Such as sauces; creams such as cream cream or fresh cream; jams such as strawberry jam or orange marmalade; general foods such as bread, soup, and various instant foods; oral compositions such as toothpaste. [Examples] Hereinafter, the present invention will be specifically described by way of Examples, but the present invention is not limited thereto. In the examples, unless otherwise specified, those described as "%" are based on mass. Example 1: Aroma evaluation of 4-alkoxycinnamic aldehyde Preparation of 4-ethoxycincosaldehyde (Inventive product 1) and 4-isopropyloxygen according to the synthesis reaction described in Japanese Patent Laid-Open Publication No. 2000-507227 The cinnamic aldehyde (Inventive Product 2), the 1% ethanol solution was prepared as an evaluation liquid for the aroma evaluation. The evaluation liquid was prepared in the sample bottle, the aroma evaluation from the bottle mouth was performed, and the aroma evaluation was performed by five well-trained inspectors by the fragrance paper impregnated with the evaluation liquid. The average evaluation is shown in Table 1 below. According to the following Table 1, it is known that it has aromas such as spice, waxy, fatty, green, and metallic. [Table 1] Example 2: Strawberry-like flavoring composition A strawberry-shaped flavoring composition was prepared according to the formulation of Table 2 below. [Table 2] A novel strawberry-like flavoring composition was prepared by mixing 2.0 g (2.0% by mass) of the present invention 1 or 2 with 98.0 g of the above-mentioned strawberry flavor composition (Comparative product 1). In the comparative product 1, the product of the present invention 1 is mixed as the product 3 of the present invention, and the product of the invention of the comparative product 1 is mixed as the product 4 of the present invention. The inventive product 3 or 4 and the comparative product 1 were compared by 5 professional inspectors. Aroma evaluation was carried out by preparing 10 ml of the fragrance composition in a sample bottle (30 ml), performing aroma evaluation from the mouth of the bottle, and comparing by the well-trained 5 professional inspectors by the aroma paper impregnated with the fragrance composition. . As a result, all of the five professional inspectors captured the characteristics of the fresh strawberry of the present invention 3 or 4 as compared with the comparative product 1, and were particularly excellent in terms of sustainability. In other words, it was confirmed that the aroma of the food or drink can be imparted or enhanced by including the flavor adjusting agent of the present invention 1 or 2 in the food or beverage. Further, it was confirmed that the product 3 or 4 of the present invention does not have a bitter taste, astringency or a pungent taste, and does not have a "residual feeling". Example 3: Formulation of strawberry-like flavoring composition in snow cheese The strawberry-shaped flavoring composition obtained in Example 2 (Comparative product 1 or inventive product 3) was added to the following snow cheese formula. In cedar, snow yoghurt was prepared by a conventional method, and was eaten by a well-trained five functional inspectors for sensory evaluation. Snow cheese blending formula (mass parts) Sugar: 10, sugar (75%): 6, fructose glucose liquid sugar (75%): 5, citric acid (crystallization): 0.1, 1/5 strawberry juice (20% by mass strawberry juice) ): 10. The present invention 3 (or comparative product 1): 0.2, and the total amount is 100 by water. The keffers were functionally evaluated by 5 functional inspectors. As a result, all of the five functional inspectors evaluated that the sorbet to which the present invention 3 was added was stronger than the sorbet to which the comparative product 1 was added, and the fresh strawberry was enhanced, and the taste was also sweet. Further, it has been confirmed that the sorbet to which the present invention 3 is added does not have a bitterness, astringency or a pungent taste, and does not have a "residual feeling". Example 4: Confirmation of Sweetness 4-Ethyl cinnamic aldehyde (Inventive Product 1) and 4-isopropoxycinnamic aldehyde (Inventive Product 2) were diluted in ethanol to prepare a 10% by mass ethanol solution. A solution in which the inventive products 1 and 2 were dissolved at a concentration shown in Table 3 below was prepared by diluting it with water. Further, 4-methoxycinnamic aldehyde (Comparative Product 2) as a comparative product was diluted by the same method as in Inventions 1 and 2, and a solution having the concentration shown in Table 3 below was prepared. Using no added water as a control, the well-trained 10 panelists inspected the solutions in which the inventive products 1, 2 and the comparative product 2 were dissolved, thereby evaluating the sweetness. The sweetness score was based on water as a control, with 0: no change compared to the control, 1: slightly sweeter compared to the control, 2: sweetness compared to the control, 3: versus control The product was strongly perceived as having a sweet taste, 4: the sweetness was too strong, and the taste was poorly balanced and scored. The average scores of 10 of the functional inspectors are shown in Table 3 below. [table 3] As shown in the above Table 3, when the 10% by mass ethanol solution of the present invention 1 and 2 was diluted in water, the aqueous solution had a sweet taste. In addition, it is understood that the sweetness is perceived in the range of 10 ppm to 5000 ppm based on the mass, and particularly good sweetness is perceived at about 25 ppm to 1000 ppm. On the other hand, when the 10% by mass ethanol solution of Comparative Product 2 is diluted in water, the aqueous solution also has a sweet taste. In addition, it is understood that the sweetness is perceived in the range of 50 ppm to 10000 ppm based on the mass, and a sweet taste is particularly perceived at about 100 ppm to 5,000 ppm. Example 5: Comparison with aqueous granulated sugar A 50 ppm aqueous solution of the present inventions 1, 2 and Comparative product 2 was prepared by the same method as in Example 4, and further prepared in an amount of 1 to 10% by mass per 0.5% by mass. A granulated sugar solution. It was judged by the well-trained 10 panelists that the 50 ppm aqueous solution of the present inventions 1 and 2 and the comparative product 2 had the same sweetness as the 1-3% by mass aqueous solution of granulated sugar. The results are shown in Table 4 below. [Table 4] According to the results of the above Table 4, the inventive products 1 and 2 have stronger sweetness than the comparative product 2. Regarding the comparative product 2, there was also a functional inspector who was evaluated to have a concentration lower than 1% by mass of the granulated sugar aqueous solution. Further, it was confirmed that the inventive products 1 and 2 have a sweet taste at a low concentration of about 1/200 to 1/1000 as compared with granulated sugar. Example 6: Confirmation of the sweetness-enhancing effect The sweetness-enhancing 5-member inspector tasted a 3 mass% sucrose aqueous solution, and 50 ppm of the aqueous solution of the inventive product 1 and 2 was added thereto, thereby performing sweetness Flavor functional evaluation. As a result, all of the five granulated sugar solutions in which the present inventions 1 and 2 were added to 50 ppm were more sweet than the 3% by mass aqueous granulated sugar solution. Example 7: Enhancement of the sweetness of the orange juice The orange juice of the present inventions 1 and 2 was added to the orange juice of 100% of the commercially available juice so as to be 50 ppm. These were tasted by five well-trained inspectors to perform a sensory evaluation of sweetness. As a result, it was evaluated that the orange juice of the present inventions 1 and 2 was added in an amount of 50 ppm, and the sweetness was stronger than that of the orange juice without added juice. Example 8: Evaluation of Sweetness of Sugared Milk As shown in Table 5 below, a 10% by mass ethanol solution of the present invention 1 and 2 and Comparative Product 2 was formulated in a sugared milk base material to prepare a sugared milk. Regarding the sugared milk, the additive-free product is used as the reference product 1, and the product of the present invention is formulated as the present invention 5, and the product of the present invention 2 is used as the present invention 6 and the comparative product 2 is used as the comparison. Product 3. [table 5] For the sweetened milk prepared by the above method, the taste was evaluated by 10 well-trained functional inspectors using reference product 1 as a control (control). The sweetness evaluation was evaluated by the tasting reference product 1, the inventive products 5 and 6, and the comparative product 3. The sweetness score was scored as -1: sweet taste deterioration, 0: no significant difference, 1: sweet taste is strong, 2: sweet taste is strong, and 3: sweetness is significantly stronger than reference product 1. The average scores of 10 functional inspectors are shown in Table 6 below. [Table 6] According to the results of the above-mentioned Table 6, the inventive products 5 and 6 to which the inventive products 1 and 2 are added to the sweetened milk (substrate) have the effect of enhancing the sweetness of the sweetened milk, and therefore, the present invention 1 and 2 sweetness enhancement effect. On the other hand, the comparative product 3 in which the comparative product 2 was added to the sugared milk (substrate) showed almost no effect of enhancing the sweetness of the sweetened milk.

no

Claims (7)

一種香味調整劑,其係以下述式(1)所表示之化合物為有效成分: [化1]上述式(1)中,R表示碳數2至4之烴基。A flavor adjusting agent which is a compound represented by the following formula (1): [Chemical Formula 1] In the above formula (1), R represents a hydrocarbon group having 2 to 4 carbon atoms. 如請求項1之香味調整劑,其中香味調整係香氣之賦予或增強。The fragrance adjuster of claim 1, wherein the fragrance adjustment is imparted or enhanced by the aroma. 如請求項1之香味調整劑,其中香味調整係甜味之賦予或增強。The fragrance adjuster of claim 1, wherein the flavor adjustment is imparted or enhanced by the sweetness. 一種飲食品用香料組合物,其含有如請求項1至3中任一項之香味調整劑作為有效成分。A flavoring composition for foods and drinks comprising the flavoring agent according to any one of claims 1 to 3 as an active ingredient. 一種飲食品,其含有如請求項1之香味調整劑或如請求項4之飲食品用香料組合物。A food or drink containing the flavor adjuster of claim 1 or the flavor composition for foods and drinks according to claim 4. 一種飲食品之香氣賦予或增強方法,其係使飲食品中含有如請求項1之上述式(1)所表示之化合物。A method for imparting or enhancing an aroma of a food or drink, which comprises a compound represented by the above formula (1) of claim 1 in a food or drink. 一種飲食品之甜味賦予或增強方法,其係使飲食品中含有如請求項1之上述式(1)所表示之化合物。A method for imparting or enhancing a sweetness of a food or drink, which comprises a compound represented by the above formula (1) of claim 1 in a food or drink.
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