JP2012224773A - Fragrance composition - Google Patents
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- JP2012224773A JP2012224773A JP2011094660A JP2011094660A JP2012224773A JP 2012224773 A JP2012224773 A JP 2012224773A JP 2011094660 A JP2011094660 A JP 2011094660A JP 2011094660 A JP2011094660 A JP 2011094660A JP 2012224773 A JP2012224773 A JP 2012224773A
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- hydroxy
- furanone
- fragrance
- methional
- ethyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 239000003205 fragrance Substances 0.000 title claims abstract description 53
- 235000013305 food Nutrition 0.000 claims abstract description 36
- CLUWOWRTHNNBBU-UHFFFAOYSA-N 3-methylthiopropanal Chemical compound CSCCC=O CLUWOWRTHNNBBU-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000000796 flavoring agent Substances 0.000 claims description 20
- 235000019634 flavors Nutrition 0.000 claims description 20
- 239000002304 perfume Substances 0.000 claims description 16
- UNYNVICDCJHOPO-UHFFFAOYSA-N sotolone Chemical compound CC1OC(=O)C(O)=C1C UNYNVICDCJHOPO-UHFFFAOYSA-N 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 13
- GWCRPYGYVRXVLI-UHFFFAOYSA-N 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone Chemical compound CCC1OC(C)=C(O)C1=O GWCRPYGYVRXVLI-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 235000013361 beverage Nutrition 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- -1 furanone compound Chemical class 0.000 claims description 5
- QJYOEDXNPLUUAR-UHFFFAOYSA-N 5-ethyl-4-hydroxy-2-methylfuran-3-one Chemical compound CCC1=C(O)C(=O)C(C)O1 QJYOEDXNPLUUAR-UHFFFAOYSA-N 0.000 claims 8
- YNKQMZRTPPVLLL-UHFFFAOYSA-N 5,5-Dimethyl-2(5H)-furanone Chemical compound CC1(C)OC(=O)C=C1 YNKQMZRTPPVLLL-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 12
- 235000014347 soups Nutrition 0.000 description 20
- TXBANKNWILQCFG-UHFFFAOYSA-N 4-hydroxyfuran-3-one Chemical class OC1=COCC1=O TXBANKNWILQCFG-UHFFFAOYSA-N 0.000 description 13
- YFEHVRMRZKALIR-UHFFFAOYSA-N 4-hydroxy-2h-furan-5-one Chemical compound OC1=CCOC1=O YFEHVRMRZKALIR-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000009472 formulation Methods 0.000 description 9
- 235000019629 palatability Nutrition 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 244000294411 Mirabilis expansa Species 0.000 description 6
- 235000015429 Mirabilis expansa Nutrition 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 235000013536 miso Nutrition 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 235000019640 taste Nutrition 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 235000012149 noodles Nutrition 0.000 description 5
- 235000013311 vegetables Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 235000014102 seafood Nutrition 0.000 description 4
- KXYCNEIORCQEFU-UHFFFAOYSA-N 2-ethyl-4-(hydroxymethyl)furan-3-one Chemical compound CCC1OC=C(CO)C1=O KXYCNEIORCQEFU-UHFFFAOYSA-N 0.000 description 3
- 241000287828 Gallus gallus Species 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000008429 bread Nutrition 0.000 description 3
- 235000013330 chicken meat Nutrition 0.000 description 3
- 235000009508 confectionery Nutrition 0.000 description 3
- 235000011194 food seasoning agent Nutrition 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 235000019643 salty taste Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 2
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 2
- 239000004278 EU approved seasoning Substances 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 2
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 2
- 235000015278 beef Nutrition 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 235000015277 pork Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 1
- 241000512259 Ascophyllum nodosum Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 240000000599 Lentinula edodes Species 0.000 description 1
- 235000001715 Lentinula edodes Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000269851 Sarda sarda Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 235000013334 alcoholic beverage Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical class O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 description 1
- 235000012970 cakes Nutrition 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 229940112822 chewing gum Drugs 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000011850 desserts Nutrition 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011962 puddings Nutrition 0.000 description 1
- 235000021067 refined food Nutrition 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000014214 soft drink Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Seeds, Soups, And Other Foods (AREA)
- Seasonings (AREA)
Abstract
Description
本発明は、食品香料等として使用可能な香料組成物に関し、詳しくは特定の香気成分を含有することにより塩辛い香気を賦与することができる香料組成物に関する。 The present invention relates to a fragrance composition that can be used as a food fragrance, and more particularly to a fragrance composition that can impart a salty fragrance by containing a specific fragrance component.
近年、消費者の嗜好性が多様化してきていることに伴い、各種各様の商品の開発が望まれている。特に、飲食品業界はこの傾向が強く、消費者の嗜好に合うバラエティーに富んだ飲食品の開発が強く要求されている。
これらの要求に対して、飲食品のひとつの原料素材である香料においても、従来にない新しい要望が高まっている。
香料物質に対しては、特に、特徴があること、嗜好性の高いユニークな香気香味を有すること、より自然で天然感の香気香味の表現に優れた効果を有することなどが要求されている。
In recent years, with the diversification of consumer preferences, development of various products has been desired. In particular, this trend is strong in the food and beverage industry, and there is a strong demand for the development of a variety of food and drink that meets consumer preferences.
In response to these demands, there is an increasing new demand for fragrances, which are one raw material for foods and drinks.
For perfume substances, it is particularly required to have characteristics, to have a unique aromatic flavor with high palatability, and to have an excellent effect in expressing a more natural and natural flavor flavor.
近年、食塩（塩化ナトリウム）の摂取量を低減し、高血圧をはじめとする生活習慣病を予防したいという消費者の要望が増加している。それに伴い、食品メーカーでは減塩や低塩を謳った商品の開発が盛んになっており、食品全般について低塩化の流れがある。低塩化する場合、既存の配合から塩分を抜くだけでは味のバランスが悪くなり、消費者が物足りなさを感じる場合があるという問題点がある。こうした点を補うために、塩化カリウムなどの代用塩を使用するという方法が試みられているが、代用塩は苦味等の異味を有し、食味が低下するという問題点がある。 In recent years, there has been an increase in consumer demand for reducing salt (sodium chloride) intake and preventing lifestyle-related diseases such as hypertension. Along with this, food manufacturers are actively developing products with reduced salt and low salt, and there is a trend toward low salinity in general foods. In the case of low chlorination, there is a problem that the balance of taste is deteriorated simply by removing the salt from the existing formulation, and the consumer may feel unsatisfactory. In order to make up for this, attempts have been made to use a substitute salt such as potassium chloride. However, the substitute salt has a different taste such as a bitter taste and has a problem that the taste is lowered.
また、特許文献１〜５のように、塩味を増強することにより、結果として低塩飲食物を提供する方法、特許文献６のように、塩辛い香気を賦与する方法なども試みられている。
香料に対しては、より自然で飲食品本来の嗜好性を損なうことなく塩辛い香気を賦与できることなどが要求されている。そのため、それらの要件を合わせもった香料素材を開発することが香料産業において極めて重要な課題となっている。
Moreover, the method of providing low salt food and drink as a result by enhancing salty taste like patent documents 1-5, the method of imparting salty aroma like patent literature 6, etc. are also tried.
For fragrances, it is required that a more natural and salty fragrance can be imparted without impairing the original taste of food and drink. Therefore, the development of a perfume material that meets these requirements is a very important issue in the perfume industry.
特許文献１の方法は麹分解液、特許文献２は飽和脂肪族モノカルボン酸、特許文献３はγ−アミノ酪酸と有機酸、特許文献４はアミノ酸とコハク酸を添加することにより、塩味を増強させる方法であるが、いずれも十分な効果が得られないだけでなく、原料に由来する香味が風味を損なうため、飲食品の嗜好性が低下するという問題点があった。
特許文献５はトレハロースを用いて塩味を増強する方法であるが、トレハロースは溶解度が低く、水分含量が少ない食品には使用が困難であり、口溶けも悪いという問題点があった。
特許文献６の方法は、４−ヒドロキシ−２(５)−エチル−５(２)−メチル−３(２Ｈ)−フラノンとフルフリルアルコールの混合物により塩辛い香気を賦与する方法であるが、これらの成分の組み合わせでは十分な効果が得られないという問題点があった。
The method of Patent Document 1 is a soot decomposition solution, Patent Document 2 is a saturated aliphatic monocarboxylic acid, Patent Document 3 is γ-aminobutyric acid and an organic acid, and Patent Document 4 is an amino acid and succinic acid to enhance salty taste. However, not only can a sufficient effect be obtained, but also the flavor derived from the raw material impairs the flavor, so that there is a problem that the palatability of the food and drink is lowered.
Patent Document 5 is a method for enhancing the salty taste using trehalose. However, trehalose has a problem that it is difficult to use for foods with low solubility, low moisture content, and poor mouth melt.
The method of Patent Document 6 is a method in which a salty aroma is imparted by a mixture of 4-hydroxy-2 (5) -ethyl-5 (2) -methyl-3 (2H) -furanone and furfuryl alcohol. There is a problem that a sufficient effect cannot be obtained by combining the components.
本発明の課題は、消費者の減塩志向にマッチした嗜好性に優れた塩辛い香気を賦与することができる香料組成物およびそれらを配合した飲食品を提供することにある。
なお、塩辛い香気とは醤油の揮発性成分に認められる塩辛い匂い（非特許文献１）や韓国の伝統的な発酵大豆味噌の品質因子のひとつである塩辛い匂い（briny：the smell associated with ocean air, salt water and picking salt）（非特許文献２）で定義される。
The subject of this invention is providing the fragrance composition which can provide the salty fragrance excellent in the palatability matched with the consumer's salt reduction intention, and the food / beverage products which mix | blended them.
Salty aroma is a salty odor found in the volatile components of soy sauce (Non-patent Document 1) and one of the quality factors of traditional Korean fermented soybean miso (briny: the smell associated with ocean air, salt water and picking salt) (Non-Patent Document 2).
本発明者らは、より自然で飲食品の嗜好性を損なうことなく塩辛い香気を賦与することができる香気成分を鋭意検討した結果、各々単独では効果を有しない香気成分の混合物が相互作用によって全く異なった塩辛い香気を呈することを見出した。
すなわち、生のジャガイモ様の香気特性を有するメチオナールと、ケーキ様あるいは砂糖様等の香気特性を有する４−ヒドロキシ−３（２Ｈ）−フラノン類、あるいは黒糖様等の香気特性を有する３−ヒドロキシ−２（５Ｈ）−フラノン類とを調合香料中に共存して含有させた場合のみ、各々の化合物を単独で含有させた場合には賦与することができない、極めて嗜好性に優れた塩辛い香気を賦与できる香料組成物の提供が可能になるという新たな事実を見出し、本発明を完成するに至った。
As a result of earnestly examining the fragrance components that can impart a salty fragrance without impairing the taste of food and drink, the inventors have found that a mixture of fragrance components each having no effect alone is completely affected by the interaction. It has been found that it has a different salty aroma.
That is, methional having a raw potato-like aroma characteristic, 4-hydroxy-3 (2H) -furanones having a cake-like or sugar-like aroma characteristic, or 3-hydroxy- having a brown sugar-like aroma characteristic Only when 2 (5H) -furanones coexist in a blended fragrance, it gives a salty fragrance with excellent palatability that cannot be imparted when each compound is contained alone. The present inventors have found a new fact that it is possible to provide a fragrance composition that can be produced, and have completed the present invention.
すなわち、本発明は、メチオナールと、４−ヒドロキシ−３（２Ｈ）−フラノン類又は３−ヒドロキシ−２（５Ｈ）−フラノン類のいずれかの二種化合物を含有する、あるいは三種化合物の全てを含有することを特徴とする香料組成物、並びにそれらを配合した飲食品である。 That is, the present invention contains methional and two compounds of 4-hydroxy-3 (2H) -furanone or 3-hydroxy-2 (5H) -furanone, or contains all three compounds. It is the fragrance | flavor composition characterized by doing, and the food / beverage products which mix | blended them.
本発明の香料組成物は、極微量の添加で飲食品の嗜好性を損なうことなく、自然に、塩辛い香気を賦与することができる。
本発明の香料組成物は、高血圧、腎臓病、心臓病などの患者や患者予備軍が必要とする低ナトリウム食品、すなわち減塩目的で食塩の添加量を減らしたいにもかかわらず、風味や嗜好性の低下の点で減塩率が制限されているような飲食品に好適である。
The fragrance composition of the present invention can impart a salty fragrance naturally without impairing the palatability of the food or drink by adding a trace amount.
The fragrance composition of the present invention is a low-sodium food that is necessary for patients with high blood pressure, kidney disease, heart disease, etc. It is suitable for foods and drinks in which the salt reduction rate is limited in terms of the deterioration of the property.
以下に、本発明を実施の形態に即して詳細に説明する。
（Ａ）有効成分
メチオナール（Methional）は、３−チオメチルプロパナールとも呼ばれ、メチオニンが酸化して生成する化合物である。なお、牛乳の日光臭はこの化合物によるとされ、チーズフレーバーとして用いられている。
Hereinafter, the present invention will be described in detail according to embodiments.
(A) Active ingredient Methional is also called 3-thiomethylpropanal and is a compound formed by oxidation of methionine. The sunlight odor of milk is attributed to this compound and is used as a cheese flavor.
４−ヒドロキシ−３（２Ｈ）−フラノン類は、下記式（１）
３−ヒドロキシ−２（５Ｈ）−フラノン類は、下記式（２）
なお、この３−ヒドロキシ−４,５−ジメチル−２（５Ｈ）−フラノンは日本酒を長期間貯蔵した古酒の焦げ臭い匂いとして知られている。
3-Hydroxy-2 (5H) -furanones are represented by the following formula (2)
This 3-hydroxy-4,5-dimethyl-2 (5H) -furanone is known as a burnt smell of old sake that has been stored for a long time.
メチオナールおよび４−ヒドロキシ−３（２Ｈ）−フラノン類、３−ヒドロキシ−２（５Ｈ）−フラノン類は、市販の製品を必要に応じて精製することにより得ることができる。また、天然物より抽出したものを精製して使用することも可能である。但し、メチオナールおよび４−ヒドロキシ−３（２Ｈ）−フラノン類、３−ヒドロキシ−２（５Ｈ）−フラノン類の入手法は、これらの方法に限定されるものではない。 Methional and 4-hydroxy-3 (2H) -furanones and 3-hydroxy-2 (5H) -furanones can be obtained by purifying commercially available products as necessary. Moreover, it is also possible to refine | purify and use what was extracted from the natural product. However, the method for obtaining methional, 4-hydroxy-3 (2H) -furanones, and 3-hydroxy-2 (5H) -furanones is not limited to these methods.
（Ｂ）配合割合
本発明の香料組成物の有効成分であるメチオナールおよび４−ヒドロキシ−３（２Ｈ）−フラノン類、３−ヒドロキシ−２（５Ｈ）−フラノン類は、メチオナールを必須とする二成分、もしくは三成分のみの組み合わせで用いることもできる他、他の香料素材と任意の割合の混合物として用いることもできる。
メチオナール及び４−ヒドロキシ−３（２Ｈ）−フラノン類、３−ヒドロキシ−２（５Ｈ）−フラノン類の混合割合には特別の制限はなく、これらの有効成分の相互作用として塩辛い香気が発現される割合であれば良い。この割合に関しては、いずれの有効成分も単独では塩辛い香気が認められないことから、当業者であれば、本発明品の用途などを勘案の上、適当な割合を容易に定めることができる。
(B) Mixing ratio Methional and 4-hydroxy-3 (2H) -furanones and 3-hydroxy-2 (5H) -furanones, which are active ingredients of the fragrance composition of the present invention, are two components essential to methional. Or it can also be used in combination of only three components, and it can also be used as a mixture of other fragrance | flavor raw materials and arbitrary ratios.
The mixing ratio of methional, 4-hydroxy-3 (2H) -furanones, and 3-hydroxy-2 (5H) -furanones is not particularly limited, and a salty aroma is expressed as an interaction of these active ingredients. Any ratio is acceptable. With respect to this ratio, any active ingredient alone does not have a salty fragrance, and those skilled in the art can easily determine an appropriate ratio in consideration of the use of the product of the present invention.
通常、有効成分を二成分混合する場合は、メチオナール：４−ヒドロキシ−３（２Ｈ）−フラノン類、あるいはメチオナール：３−ヒドロキシ−２（５Ｈ）−フラノン類がそれぞれ１：９９〜９９：１の範囲である。
また、有効成分を三成分混合する場合は、混合物中のメチオナール、４−ヒドロキシ−３（２Ｈ）−フラノン類、３−ヒドロキシ−２（５Ｈ）−フラノン類のそれぞれの比率が、いずれも１％を下回らない範囲である。
Usually, when two active ingredients are mixed, methional: 4-hydroxy-3 (2H) -furanone or methional: 3-hydroxy-2 (5H) -furanone is 1:99 to 99: 1, respectively. It is a range.
When the active ingredient is mixed in three components, each ratio of methional, 4-hydroxy-3 (2H) -furanones, and 3-hydroxy-2 (5H) -furanones in the mixture is 1%. It is the range which is not less than.
メチオナール及び４−ヒドロキシ−３（２Ｈ）−フラノン類、３−ヒドロキシ−２（５Ｈ）−フラノン類を香料組成物に用いる場合、これら成分の添加量は、その目的あるいは香料組成物の種類によって異なるものの、一般的には、香料組成物全体量の０．００００００１（１ｐｐｂ）〜１００質量％、好ましくは０．０００００１（１０ｐｐｂ）〜５０質量％の範囲内を例示することができる。 When methional, 4-hydroxy-3 (2H) -furanones and 3-hydroxy-2 (5H) -furanones are used in the fragrance composition, the amount of these components to be added varies depending on the purpose or the type of the fragrance composition. However, generally, it can be exemplified within the range of 0.0000001 (1 ppb) to 100 mass%, preferably 0.000001 (10 ppb) to 50 mass% of the total amount of the fragrance composition.
本発明の香料組成物に配合される他の成分としては、特に制限は無く、用途や目的に応じて従来から使用されていた種々の香料素材が使用可能であり、具体的にはアルデヒド類、アルコール類、エステル類等の従来公知の香料素材があげられる。 As other components to be blended in the fragrance composition of the present invention, there is no particular limitation, and various fragrance materials that have been used conventionally can be used depending on the application and purpose. Specifically, aldehydes, Conventionally known perfume materials such as alcohols and esters can be mentioned.
上記のメチオナール及び４−ヒドロキシ−３（２Ｈ）−フラノン類、３−ヒドロキシ−２（５Ｈ）−フラノン類は、市販品（例えば、Sigma-Aldrich社製品、Lancaster Synthesis社製品、Acros Organics社製品、Givaudan社製品）を使用することが可能であり、好ましくはエチルアルコールやプロピレングリコール等の溶剤の希釈液として、そのまま或いは他の香料素材との併用で用いられる。なお、本発明の香料組成物が添加される飲食品としては、塩辛い香気を付与することに適した飲食品であれば特に制限はない。 The above methional and 4-hydroxy-3 (2H) -furanones and 3-hydroxy-2 (5H) -furanones are commercially available products (for example, Sigma-Aldrich, Lancaster Synthesis, Acros Organics, Givaudan product) can be used, and preferably used as a diluted solution of a solvent such as ethyl alcohol or propylene glycol as it is or in combination with other fragrance materials. In addition, as food / beverage products with which the fragrance | flavor composition of this invention is added, if it is food / beverage products suitable for providing salty fragrance, there will be no restriction | limiting in particular.
（Ｃ）飲食品
本発明の香料組成物は、各種飲食品に特に制限なく使用することができる。例えば、果実類又はその加工品、野菜又はその加工品、魚介類又はその加工品、練製品、調理食品、総菜類、スナック類、珍味類、加工食品、栄養食品、茶飲料およびコーヒー飲料などの嗜好飲料、果汁飲料、炭酸飲料、清涼飲料、機能性飲料、アルコール飲料、アイスクリーム、シャーベット等の冷菓類、ゼリー、プリン、羊かん等のデザート類、クッキー、ケーキ、チョコレート、チューイングガム、饅頭等の菓子類、菓子パン、食パン等のパン類、ジャム類、ラムネ、タブレット、錠菓類などがあげられる。
さらに、日本料理のだし、例えば、鰹節、魚介類、昆布、シイタケ、鶏肉、野菜類などのだし汁、麺つゆ、味噌汁および和風調味料、又は、西洋料理のスープストック、例えば、牛肉、鶏肉、豚肉、魚介類、野菜類などのだし汁、コンソメスープ及び洋風調味料、又は、中華料理のタン（湯）、例えば、牛肉、鶏肉、豚肉、魚介類、野菜類などからとったスープ及び中華調味料などがあげられる。
(C) Food / beverage products The fragrance | flavor composition of this invention can be especially used without a restriction | limiting in various food / beverage products. For example, fruits or processed products thereof, vegetables or processed products thereof, seafood or processed products thereof, paste products, cooked foods, prepared vegetables, snacks, delicacies, processed foods, nutritional foods, tea drinks and coffee drinks, etc. Taste drinks, fruit juice drinks, carbonated drinks, soft drinks, functional drinks, alcoholic drinks, ice cream, confectionery such as sherbet, desserts such as jelly, pudding, sheep cane, cookies, cakes, chocolate, chewing gum, buns, etc. , Breads such as confectionery bread and bread, jams, ramunes, tablets and tablet confectionery.
In addition, Japanese soup stock such as bonito, seafood, kelp, shiitake, chicken, vegetables, etc., soup stock, noodle soup, miso soup and Japanese seasoning, or western soup stock such as beef, chicken, pork , Soup stocks such as seafood, vegetables, consomme soup and Western-style seasonings, or Chinese food tongue (hot water), for example, soup and Chinese seasonings taken from beef, chicken, pork, seafood, vegetables, etc. Can be given.
本発明の香料組成物が添加される飲食品としては、塩辛い香気を付与することに適した飲食品であれば特に制限はなく、本発明の香料組成物の飲食品への添加量は、一般的には０．０００００００１質量％（１００ｐｐｔ）〜１質量％、好ましくは ０．０００００１質量％（１０ｐｐｂ）〜０．５質量％である。 The food or drink to which the fragrance composition of the present invention is added is not particularly limited as long as it is a food or drink suitable for imparting a salty fragrance, and the amount of the fragrance composition of the present invention added to the food or drink is generally Specifically, it is 0.00000001 mass% (100 ppt) to 1 mass%, preferably 0.000001 mass% (10 ppb) to 0.5 mass%.
次に実施例を示して本発明をさらに具体的に説明するが、本発明は、これらの実施例に限定されるものではない。 EXAMPLES Next, although an Example is shown and this invention is demonstrated further more concretely, this invention is not limited to these Examples.
以下の実施例において、香料組成物の有効成分であるメチオナール、４−ヒドロキシ−２（or ５）−エチル−５（or ２）−メチル−３（２Ｈ）−フラノン〔ケト−エノール互変異性体〕及び３−ヒドロキシ−４,５−ジメチル−２（５Ｈ）−フラノンは、それぞれ以下の市販品を使用した。
メチオナール：Sigma-Aldrich社製「3-(methylthio)propionaldehyde」
４−ヒドロキシ−２（or ５）−エチル−５（or ２）−メチル−３（２Ｈ）−フラノン：Givaudan社製「HOMOFURONOL」
３−ヒドロキシ−４,５−ジメチル−２（５Ｈ）−フラノン：Sigma-Aldrich社製「4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one」
In the following examples, methional, 4-hydroxy-2 (or 5) -ethyl-5 (or 2) -methyl-3 (2H) -furanone [keto-enol tautomer, which is an active ingredient of a fragrance composition ] And 3-hydroxy-4,5-dimethyl-2 (5H) -furanone used the following commercially available products, respectively.
Methional: “3- (methylthio) propionaldehyde” manufactured by Sigma-Aldrich
4-hydroxy-2 (or 5) -ethyl-5 (or 2) -methyl-3 (2H) -furanone: “HOMOFURONOL” manufactured by Givaudan
3-hydroxy-4,5-dimethyl-2 (5H) -furanone: "4,5-dimethyl-3-hydroxy-2,5-dihydrofuran-2-one" manufactured by Sigma-Aldrich
［実施例１］
下記処方により本発明の香料組成物１を得た。
The perfume composition 1 of this invention was obtained by the following prescription.
［実施例２］
下記処方により本発明の香料組成物２を得た。
A perfume composition 2 of the present invention was obtained by the following formulation.
［実施例３］
下記処方により本発明の香料組成物３を得た。
A perfume composition 3 of the present invention was obtained by the following formulation.
［比較例１］
実施例１のメチオナールの代わりにエチルアルコールを配合して香料組成物４を得た。
[Comparative Example 1]
Perfume composition 4 was obtained by blending ethyl alcohol in place of methional of Example 1.
［比較例２］
実施例２のメチオナールの代わりにエチルアルコールを配合して香料組成物５を得た。
[Comparative Example 2]
Perfume composition 5 was obtained by blending ethyl alcohol in place of methional of Example 2.
［比較例３］
実施例３のメチオナールの代わりにエチルアルコールを配合して香料組成物６を得た。
[Comparative Example 3]
Perfume composition 6 was obtained by blending ethyl alcohol in place of methional in Example 3.
［比較例４］
実施例１の４−ヒドロキシ−２（or ５）−エチル−５（or ２）−メチル−３（２Ｈ）−フラノンの代わりにエチルアルコールを配合して香料組成物７を得た。
[Comparative Example 4]
A perfume composition 7 was obtained by blending ethyl alcohol in place of 4-hydroxy-2 (or 5) -ethyl-5 (or 2) -methyl-3 (2H) -furanone of Example 1.
［実施例４］
下記処方により本発明の香料組成物８を得た。
A perfume composition 8 of the present invention was obtained by the following formulation.
［実施例４］
下記処方により本発明の味噌汁１を得た。
The miso soup 1 of this invention was obtained by the following prescription.
［比較例５］
下記処方により味噌汁２を得た。
Miso soup 2 was obtained according to the following formulation.
［実施例５］
下記処方により本発明のコンソメスープ１を得た。
Consomme soup 1 of the present invention was obtained by the following formulation.
［比較例６］
下記処方によりコンソメスープ２を得た。
Consomme soup 2 was obtained according to the following formulation.
［実施例６］
下記処方により麺つゆ１を得た。
Noodle soup 1 was obtained by the following formulation.
［比較例７］
下記処方により麺つゆ２を得た。
Noodle soup 2 was obtained by the following formulation.
［試験例１］
香料組成物１、２、３、４、５、６、７をそれぞれ単独で０．１質量％添加した７種類の１％食塩水について１０名の専門パネラーにより１％食塩水を対照品として塩辛い香気の強さを７段階で評価した。
その結果、専門パネラーの全員が本発明品である香料組成物１、２、３、４を添加した１％食塩水は塩辛い香気が強く感じられると評価した。詳細を表１１に示した。
[Test Example 1]
7 types of 1% saline containing 0.1% by mass of each of the perfume compositions 1, 2, 3, 4, 5, 6, 7 are salty with 1% saline as a reference product by 10 expert panelists The intensity of the fragrance was evaluated on a 7-point scale.
As a result, all of the specialized panelists evaluated that the 1% saline solution to which the perfume compositions 1, 2, 3, and 4 of the present invention were added felt a strong salty aroma. Details are shown in Table 11.
［試験例２］
味噌汁１、２について１０名の専門パネラーにより塩辛い香気の強さおよび風味の複雑さを７段階で評価した。
その結果、専門パネラーの全員が本発明品を添加した味噌汁１の方がより塩辛い香気が強く感じられ、複雑な風味となり嗜好性が向上すると評価した。その詳細を表１２に示した。
[Test Example 2]
With respect to miso soups 1 and 2, 10 expert panelists evaluated the strength of salty fragrance and the complexity of flavor in 7 stages.
As a result, all the expert panelists evaluated that the miso soup 1 to which the product of the present invention was added had a stronger salty aroma, resulting in a complex flavor and improved palatability. The details are shown in Table 12.
［試験例３］
コンソメスープ１、２の２種類について５名の専門パネラーにより塩辛い香気および風味の複雑さを評価した。その結果、専門パネラーの全員が本発明品を添加したコンソメスープ１の方が、より塩辛い香気が強く感じられ、複雑な風味となり嗜好性が向上すると評価した。
[Test Example 3]
Two types of consomme soups 1 and 2 evaluated the complexity of salty aroma and flavor by five expert panelists. As a result, all the specialized panelists evaluated that the consomme soup 1 to which the product of the present invention was added felt a stronger salty aroma, resulting in a complex flavor and improved palatability.
［試験例４］
麺つゆ１、２の２種類について、５名の専門パネラーにより塩辛臭および風味の複雑さを評価した。その結果、専門パネラーの全員が本発明品を添加した麺つゆ１の方が、より塩辛い香気が強く感じられ、複雑な風味となり嗜好性が向上すると評価した。
[Test Example 4]
Two types of noodle soups 1 and 2 were evaluated by 5 expert panelists for the salty odor and the complexity of the flavor. As a result, all of the expert panelists evaluated that the noodle soup 1 to which the product of the present invention was added had a stronger salty aroma and a complex flavor and improved palatability.
本発明のメチオナールおよび４−ヒドロキシ−３（２Ｈ）−フラノン類、又は、３−ヒドロキシ−２（５Ｈ）−フラノン類のいずれか、あるいは全てを含有する香料組成物およびそれらを飲食品に使用すると、極めて嗜好性に優れた塩辛い香気を賦与することができる。 A fragrance composition containing any or all of methional and 4-hydroxy-3 (2H) -furanones or 3-hydroxy-2 (5H) -furanones of the present invention and food and drinks thereof. It is possible to impart a salty fragrance with extremely excellent palatability.
Claims (11)
で表されるフラノン化合物を有効成分として含有することを特徴とする香料組成物。 Methional and the following formula (1)
The fragrance | flavor composition characterized by containing the furanone compound represented by these as an active ingredient.
で表されるフラノン化合物を有効成分として含有することを特徴とする香料組成物。 Methional and the following formula (2)
The fragrance | flavor composition characterized by containing the furanone compound represented by these as an active ingredient.
下記式（１）
で表されるフラノン化合物と、
下記式（２）
で表されるフラノン化合物を有効成分として含有することを特徴とする香料組成物。 Methional,
Following formula (1)
A furanone compound represented by:
Following formula (2)
The fragrance | flavor composition characterized by containing the furanone compound represented by these as an active ingredient.
請求項１又は３に記載の香料組成物。 In Formula (1), R 1 and R 2 are each independently methyl or ethyl.
The fragrance composition according to claim 1 or 3.
請求項２又は３に記載の香料組成物。 In Formula (2), R 1 and R 2 are each independently methyl or ethyl.
The fragrance composition according to claim 2 or 3.
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| PCT/JP2012/060732 WO2012144604A1 (en) | 2011-04-21 | 2012-04-20 | Flavoring agent composition |
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| CN111243684A (en) * | 2020-03-06 | 2020-06-05 | 安徽中烟工业有限责任公司 | Method for judging synergistic effect of caramel-sweet-fragrance ternary mixture based on sigma-tau intensity method |
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| CN111243684B (en) * | 2020-03-06 | 2023-02-28 | 安徽中烟工业有限责任公司 | Method for judging synergistic effect of caramel-sweet-fragrance ternary mixture based on sigma-tau intensity method |
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