JP4771246B2 - Aroma / flavor / flavoring composition and food / beverage, perfume, cosmetics or tobacco to which it is added - Google Patents
Aroma / flavor / flavoring composition and food / beverage, perfume, cosmetics or tobacco to which it is added Download PDFInfo
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- JP4771246B2 JP4771246B2 JP2001198954A JP2001198954A JP4771246B2 JP 4771246 B2 JP4771246 B2 JP 4771246B2 JP 2001198954 A JP2001198954 A JP 2001198954A JP 2001198954 A JP2001198954 A JP 2001198954A JP 4771246 B2 JP4771246 B2 JP 4771246B2
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- flavor
- dimethyl
- furanone
- pentyl
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- 239000000203 mixture Substances 0.000 title claims description 49
- 239000000796 flavoring agent Substances 0.000 title claims description 44
- 235000019634 flavors Nutrition 0.000 title claims description 43
- 239000002304 perfume Substances 0.000 title claims description 16
- 239000002537 cosmetic Substances 0.000 title claims description 14
- 235000013305 food Nutrition 0.000 title claims description 13
- 241000208125 Nicotiana Species 0.000 title claims description 11
- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims description 11
- 235000013361 beverage Nutrition 0.000 title description 6
- 239000003205 fragrance Substances 0.000 claims description 29
- LRKURLXWGJNWOJ-SNVBAGLBSA-N (2R)-3,4-dimethyl-2-pentyl-2H-furan-5-one Chemical compound CCCCC[C@H]1OC(=O)C(C)=C1C LRKURLXWGJNWOJ-SNVBAGLBSA-N 0.000 claims description 19
- LRKURLXWGJNWOJ-JTQLQIEISA-N (2S)-3,4-dimethyl-2-pentyl-2H-furan-5-one Chemical compound CCCCC[C@@H]1OC(=O)C(C)=C1C LRKURLXWGJNWOJ-JTQLQIEISA-N 0.000 claims description 16
- 244000269722 Thea sinensis Species 0.000 description 12
- 235000019504 cigarettes Nutrition 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 235000005135 Micromeria juliana Nutrition 0.000 description 5
- 241000246354 Satureja Species 0.000 description 5
- 235000007315 Satureja hortensis Nutrition 0.000 description 5
- 235000006468 Thea sinensis Nutrition 0.000 description 5
- 235000020279 black tea Nutrition 0.000 description 5
- 235000009508 confectionery Nutrition 0.000 description 5
- 239000003599 detergent Substances 0.000 description 4
- 239000013022 formulation composition Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 235000013616 tea Nutrition 0.000 description 4
- LRKURLXWGJNWOJ-UHFFFAOYSA-N 3,4-dimethyl-2-pentyl-2h-furan-5-one Chemical compound CCCCCC1OC(=O)C(C)=C1C LRKURLXWGJNWOJ-UHFFFAOYSA-N 0.000 description 3
- 244000144730 Amygdalus persica Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000006040 Prunus persica var persica Nutrition 0.000 description 3
- -1 aroma Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000009569 green tea Nutrition 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 235000014347 soups Nutrition 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002386 air freshener Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- MTQPZHNZYWAXEH-JXMROGBWSA-N (5e)-3,4-dimethyl-5-pentylidenefuran-2-one Chemical compound CCCC\C=C1\OC(=O)C(C)=C1C MTQPZHNZYWAXEH-JXMROGBWSA-N 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 240000006766 Cornus mas Species 0.000 description 1
- 235000003363 Cornus mas Nutrition 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000001467 acupuncture Methods 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 238000003287 bathing Methods 0.000 description 1
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical class O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 description 1
- 235000014171 carbonated beverage Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 235000015203 fruit juice Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000020124 milk-based beverage Nutrition 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000004161 plant tissue culture Methods 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 235000011888 snacks Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
- Manufacture Of Tobacco Products (AREA)
- Seasonings (AREA)
- Non-Alcoholic Beverages (AREA)
- Cosmetics (AREA)
Description
【0001】
本発明は、(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび/または(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンを含有する香気・香味・香喫味付与組成物、ならびにその香気・香味・香喫味付与組成物が添加された飲食物、香水、化粧品、または、たばこに関するものである。
【0002】
【従来の技術】
従来、3,4−ジメチル−5−ペンチル−2(5H)−フラノンのラセミ体は、種々の天然物から見い出されている既知化合物である。しかしながら、その光学活性体に関する既述はなく、これまで、香気、香味、香喫味を含む香料としての有用性ならびに該化合物を添加した飲食物、香水、化粧品およびたばこについて何ら報告されていない。
【0003】
【発明が解決しようとする課題】
本発明の目的は、新たな香気、香味、香喫味付与組成物を提供することにある。
【問題点を解決するための手段】
本発明者らは、(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび/または(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンが、香気・香味・香喫味付与組成物の成分として特に優れ、添加された飲食物、香水、化粧品およびたばこの特性を引き立たせるのに特に適していることを見い出した。さらに本発明者らが鋭意研究を行なった結果、(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンと(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンとでは、香気、香味、香喫味が大きく異なることが明らかとなった。
【0004】
すなわち、本発明によると前記2種の化合物の比率を調整することにより、特有の多彩な香気を表現することができるのである。
【0005】
本発明の香気・香味・香喫味付与組成物は、(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび/または(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンを、等量とならないように配合してなることを特徴とする香気・香味・香喫味付与組成物である。本発明の香気・香味・香喫味付与組成物においては、(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンと(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンのうち一方の比率を30重量%以下とすることが好ましい態様の一つである。
【0006】
また、本発明の香気・香味・香喫味付与組成物を、各種飲食物、香水、化粧品、または、たばこに添加することにより特有の香気、香味、香喫味を付与することができる。
【0007】
【発明の実施の形態】
本発明の香気・香味付与組成物において、香気・香味付与成分は、(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンと(−)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンである。これらの化合物は、ラセミ体の3,4−ジメチル−5−ペンチル−2(5H)−フラノンをキラルセルカラムを装着した高速液体クロマトグラフィーあるいはガスクロマトグラフィーにて分離取得することができる。
【0008】
ラセミ体の3,4−ジメチル−5−ペンチル−2(5H)−フラノンは、オランダ特許第6,514,140号公報に従い、酢酸エチルとヘキサナールから製造することができる。また、Agric.Biol.Chem.,Vol,49,1985(3601−3603)に記載の方法に従い、3,4−ジメチル−5−ペンチリデン−2(5H)−フラノンを酸化白金触媒を用いて水素還元することによっても得ることができる。
【0009】
本発明においては、上記(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンと(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンの比率を重量比で1:0から0:1の間で、等量とならないように調整することができる。すなわち、上記(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンは、それぞれ単独で使用しても良く、あるいは両化合物を50:50以外の任意の割合(等量とならないように調整する)で混合して使用しても良い。 本発明では、(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンと(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンのうち、一方の比率を45重量%以下とすることが好ましく、より好ましくは40重量%以下であり、さらに好ましくは30重量%以下である。
【0010】
本発明では、両化合物を任意の比率で混合することにより様々な香気・香味・香喫味付与組成物を作り出すことができる。
【0011】
すなわち(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンは、クローブ、パセリ様、やや油っぽい、フルーティーで甘いトップ、メタリックで粉っぽい、古いお茶のイメージ、はっきりした香りを有する。
【0012】
一方、(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンは、甘みのある茶様、瓜的なグリーン感、化粧品的、粕的、自然、清涼感、ハーブ的、さらっとしていて柔らかい、お茶に含まれている柔らかいラクトン感、ライトで華やか、セロリ的、ぼんやりした香りを有する。
【0013】
本発明において、(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンは、上述のとおり、これら化合物を単独もしくは両者の混合物として使用することができ、また、他の香料等の成分を配合して香気・香味・香喫味を付与する香料組成物とすることもできる。前記他の香料等の成分としては、通常の香料に使用される成分であれば特に限定されることなく配合することができる。
【0014】
この香料組成物における(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンの含有量は、特に限定されないが、香料組成物中に0.01〜50重量%程度の割合で含有させることが好ましい。しかしながら、意図する官能効果によってはこの範囲外でも使用し得る。
【0015】
本発明の(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび/または(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンを含有する香気・香味・香喫味を付与する香料組成物は、このものの香気、香味、香喫味付与効果を期待する各種飲食物、香水、化粧品、または、たばこであれば特に限定することなく添加することができる。
【0016】
例えば、飲食物としては、果汁飲料類、果実酒類、乳飲料類、炭酸飲料類のごとき飲料類;アイスクリーム類、シャーベット類、アイスキャンディーのごとき冷菓類;和洋菓子類、ジャム類、チューインガム類、パン類、コーヒー、ココア、紅茶、お茶のごとき嗜好品類;和風スープ類、洋風スープ類のごときスープ類;風味調味料各種インスタント飲料乃至食品類、各種スナック食品類などが挙げられ、香粧品類としては、香水類、石鹸、ボディーシャンプー、シャンプー・リンス類、洗剤、ヘアークリーム類、ポマード類、その他の毛髪用化粧料基剤;オシロイ、口紅、その他の化粧料基剤や化粧料洗剤基剤、洗濯用洗剤・柔軟剤類、室内芳香剤類、トイレ用芳香剤・消臭剤・洗剤類などが挙げられる。たばこの種類については通常の葉たばこを原料として製造される紙巻きたばこ、パイプたばこ、葉巻たばこなどの他、天然繊維あるいは植物の組織培養物を用いて製造される合成たばこなどが挙げられる。紙巻きたばこについては製造用の材料品、例えば、巻紙、糊、フィルターなどに含有させることも香喫味効果をあげることができる。また、その他のものとしては、消毒薬などの各種保健・衛生材料類、医薬品などの服用を容易にするための矯味、賦香剤などの保健・衛生・医薬品類などが挙げられる。
【0017】
本発明の(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび/または(−)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンの各種飲食物、香水、化粧品、または、たばこへの添加量は、添加する飲食物、香水、化粧品、または、たばこの種類によって適宜選択することができる。
【0018】
【実施例】
[参考例1]
(−)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび
(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンの製造法
ラセミ体の3,4−ジメチル−5−ペンチル−2(5H)−フラノンをヘキサンに溶解し10%溶液とした。この溶液を下記装置、条件で注入し液体クロマトグラフを行った。完全に分離した2つのピークを確認、分割した。前留分から溶媒を除去することにより(−)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンを得た。比旋光度は[α]D−17.4゜であった。後留分から溶媒を除去することにより(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンを得た。比旋光度は[α]D+17.3゜であった。
【0019】
(分取HPLC測定条件)
・装置;日立L−7000シリ−ズ高速液体クロマトグラフ
ポンプ:L7100
デガッサ:DG−2410
カラムオ−ブン:L−7300
UV検出器:L−7400
オートサンプラー:L7200
レコ−ダ−:Pantos U−228(Range 5mV)
・カラム;CHIRALPAK AS 20mm I.D.×250mm+ガードカラム50mm(ダイセル化学)
・移動相;ヘキサン/イソプロパノ−ル=95/5(v/v)
・流速;5.0ml/min.
・カラムオ−ブン温度;40℃
・検出器波長;230nm
・注入量;80μl
[実施例1] ピーチフレーバータイプの香気・香味付与組成物
ピーチフレーバータイプの調合組成物として次の各成分を混合した。
【0020】
上記の混合物に0.2重量部の(−)-ジヒドロボボリッドを加え、新規調合組成物を得た。(−)-ジヒドロボボリッドを加えることにより、新たにソフトな甘さを付与することができよりピーチのマイルド感を再現できた。
【0021】
[実施例2] 西瓜フレーバータイプの香気・香味付与組成物
西瓜フレーバータイプの調合組成物として次の各成分を混合した。
【0022】
上記の混合物に4.3重量部の(+)-ジヒドロボボリッドを加え、新規調合組成物を得た。(+)-ジヒドロボボリッドを加えることにより、新たに深みのあるグリーン感を付与することができ、より西瓜の瑞々しい感じを再現できた。
【0023】
[実施例3] 緑茶フレーバータイプの香気・香味付与組成物
緑茶フレーバータイプの調合組成物として次の各成分を混合した。
【0024】
上記の混合物に0.3重量部の(−)-ジヒドロボボリッドを加え、新規調合組成物を得た。ジヒドロボボリッドを加えることにより、新たにさらっとしていて柔らかい青さを付与することができ、より緑茶の瑞々しさを再現できた。
【0025】
[実施例4] 紅茶タイプの香気付与組成物
紅茶タイプの調合組成物として次の各成分を混合した。
【0026】
上記の混合物に10重量部の(+)-ジヒドロボボリッドを加え、新規調合組成物を得た。 調整した組成物をボディーシャンプー用基材にそれぞれ0.5重量%の割合で賦香したところ、ボディー感のあるハーブ的なフローラル感を付与、強調することができた。
【0027】
[実施例5] 香水用ブラックティ香気付与組成物
香水用ブラックティの調合組成物として次の各成分を混合した。
【0028】
上記香水用ブラックティの調合組成物に20重量部の(−)-ジヒドロボボリッドを加え、新規調合組成物を得た。この香料組成物10重量%のアルコール(95重量%)にして香水とした。瑞々しいグリーン感が付与、強調された香気であると評価した。
【0029】
[実施例6] ホワイトフローラル調香気付与組成物
ホワイトフローラル調の調合組成物として次の各成分を混合した。
【0030】
上記の混合物に30重量部の(+)-ジヒドロボボリッドを加え、新規調合組成物を得た。 調整した組成物を入浴剤用基材にそれぞれ0.9重量%の割合で賦香したところ、ジャスミン様フローラル感が強調された香りを付与、強調することができた。
【0031】
[実施例7] 香喫味付与組成物
香喫味調合組成物として次の各成分を混合した。
【0032】
上記の混合物に0.8重量部の(−)-ジヒドロボボリッドを加え、新規調合組成物を得た。調整した組成物を市販たばこに0.1%付香したところ、煙に軽さが出てたばこ用の香味が付与、強調することができた。
【0033】
【発明の効果】
本発明によれば、(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび/または(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンを含有する新規な香気・香味・香喫味付与組成物が得られる。(+)−3,4−ジメチル−5−ペンチル−2(5H)−フラノンおよび/または(−)− 3,4−ジメチル−5−ペンチル−2(5H)−フラノンは、香気・香味付与組成物の成分として特に優れており、添加された飲食物、香水、化粧品の特性を引き立たせるのに特に適している。[0001]
The present invention contains (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and / or (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone. The present invention relates to an aroma / flavor / flavoring imparting composition and foods / drinks, perfumes, cosmetics or tobacco to which the aroma / flavor / flavoring imparting composition is added.
[0002]
[Prior art]
Conventionally, the racemic form of 3,4-dimethyl-5-pentyl-2 (5H) -furanone is a known compound that has been found in various natural products. However, there is no description about the optically active substance, and there has been no report on the usefulness as a fragrance including aroma, fragrance and savory taste, and foods, perfumes, cosmetics and tobacco added with the compound.
[0003]
[Problems to be solved by the invention]
An object of the present invention is to provide a new aroma, flavor and flavor imparting composition.
[Means for solving problems]
We have (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and / or (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone. It has been found to be particularly excellent as a component of an aroma / flavor / flavoring imparting composition and particularly suitable for enhancing the properties of added foods, perfumes, cosmetics and tobacco. Furthermore, as a result of intensive studies by the present inventors, (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and (−)-3,4-dimethyl-5-pentyl-2 ( It was clarified that the fragrance, flavor and savory taste differ greatly from 5H) -furanone.
[0004]
That is, according to the present invention, a variety of unique fragrances can be expressed by adjusting the ratio of the two kinds of compounds.
[0005]
The fragrance, flavor and flavor imparting composition of the present invention comprises (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and / or (−)-3,4-dimethyl-5-pentyl. -2 (5H) -furanone is a fragrance / flavor / flavor imparting composition characterized by being blended so as not to have an equal amount. In the fragrance, flavor, and flavor imparting composition of the present invention, (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and (−)-3,4-dimethyl-5-pentyl- It is one of the preferred embodiments that the ratio of one of 2 (5H) -furanones is 30% by weight or less.
[0006]
Further, by adding the fragrance / flavor / flavoring imparting composition of the present invention to various foods, perfumes, cosmetics , or cigarettes, it is possible to impart a specific aroma, flavor, and flavor.
[0007]
DETAILED DESCRIPTION OF THE INVENTION
In the fragrance / flavor imparting composition of the present invention, the fragrance / flavor imparting components are (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and (−)-3,4-dimethyl-5. -Pentyl-2 (5H) -furanone. These compounds can be obtained by separating racemic 3,4-dimethyl-5-pentyl-2 (5H) -furanone by high performance liquid chromatography or gas chromatography equipped with a chiral cell column.
[0008]
Racemic 3,4-dimethyl-5-pentyl-2 (5H) -furanone can be prepared from ethyl acetate and hexanal according to Dutch Patent 6,514,140. Also, Agric. Biol. Chem. , Vol, 49, 1985 (3601-3603), and 3,4-dimethyl-5-pentylidene-2 (5H) -furanone can also be obtained by hydrogen reduction using a platinum oxide catalyst. .
[0009]
In the present invention, the ratio of the above (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone to (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone is The weight ratio can be adjusted so as not to be equal between 1: 0 and 0: 1. That is, the above (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone are each used alone. Alternatively, both compounds may be mixed and used at an arbitrary ratio other than 50:50 (adjusted so as not to be equal). In the present invention, one of (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone. The ratio is preferably 45% by weight or less, more preferably 40% by weight or less, and still more preferably 30% by weight or less.
[0010]
In the present invention, various aromas, flavors, and flavor imparting compositions can be produced by mixing both compounds in an arbitrary ratio.
[0011]
That is, (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone is clove, parsley-like, slightly oily, fruity and sweet top, metallic and powdery, old tea image, clearly Has a fragrance.
[0012]
On the other hand, (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone has a sweet tea-like, sensuous green feeling, cosmetics, acupuncture, nature, refreshing feeling, herbal, It is soft and soft, with a soft lactone feel in tea, light and gorgeous, celery, and a faint scent.
[0013]
In the present invention, (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone are as described above. These compounds can be used singly or as a mixture of both, and can be made into a fragrance composition that imparts aroma, flavor, and savory taste by blending other components such as fragrance. As other components such as the fragrance, any component that is used in a normal fragrance can be blended without particular limitation.
[0014]
The contents of (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone in this fragrance composition are Although not specifically limited, it is preferable to contain in the ratio of about 0.01 to 50 weight% in a fragrance | flavor composition. However, it can be used outside this range depending on the intended sensory effect.
[0015]
Fragrance containing (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and / or (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone of the present invention -A fragrance composition that imparts flavor and savory taste can be added without particular limitation as long as it is a variety of foods, perfumes, cosmetics , or cigarettes that are expected to have a fragrance, flavor, and savory taste imparting effect. .
[0016]
For example, as food and drink, beverages such as fruit juices, fruit liquors, milk beverages, carbonated beverages; frozen confections such as ice creams, sorbets, ice candy; Japanese and Western confectionery, jams, chewing gums, Beverages, coffee, cocoa, tea, tea and other favorite products; Japanese soups, Western soups and soups; flavor seasonings, various instant beverages and foods, various snack foods, etc. Perfumes, soaps, body shampoos, shampoos and rinses, detergents, hair creams, pomades, and other hair cosmetic bases; osiroy, lipstick, other cosmetic bases and cosmetic detergent bases, Examples include laundry detergents and softeners, indoor air fresheners, toilet air fresheners, deodorants, and detergents. Cigarette types include cigarettes, pipe cigarettes, cigarettes and the like manufactured using ordinary leaf tobacco as a raw material, as well as synthetic tobacco manufactured using natural fibers or plant tissue cultures. For cigarettes, the effect of flavoring can also be achieved by adding them to a material for production, for example, wrapping paper, glue, or a filter. Others include various health / hygiene materials such as disinfectants, taste-masking for facilitating administration of pharmaceuticals, and health / hygiene / pharmaceuticals such as flavoring agents.
[0017]
Various foods and beverages of (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and / or (-)-3,4-dimethyl-5-pentyl-2 (5H) -furanone of the present invention The amount added to perfume, cosmetics or tobacco can be appropriately selected depending on the type of food, beverage, perfume, cosmetics or tobacco to be added.
[0018]
【Example】
[Reference Example 1]
Process for the preparation of (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone -Dimethyl-5-pentyl-2 (5H) -furanone was dissolved in hexane to make a 10% solution. This solution was injected under the following apparatus and conditions to perform liquid chromatography. Two completely separated peaks were confirmed and separated. (-)-3,4-dimethyl-5-pentyl-2 (5H) -furanone was obtained by removing the solvent from the previous fraction. The specific rotation was [α] D-17.4 °. (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone was obtained by removing the solvent from the post-fraction. The specific rotation was [α] D + 17.3 °.
[0019]
(Preparative HPLC measurement conditions)
Apparatus: Hitachi L-7000 series high-performance liquid chromatograph pump: L7100
Degasser: DG-2410
Column oven: L-7300
UV detector: L-7400
Auto sampler: L7200
Recorder: Pantos U-228 (Range 5 mV)
Column: CHIRALPAK AS 20mm I. D. × 250mm + guard column 50mm (Daicel Chemical)
Mobile phase: hexane / isopropanol = 95/5 (v / v)
-Flow rate: 5.0 ml / min.
-Column oven temperature: 40 ° C
・ Detector wavelength: 230 nm
・ Injection volume: 80 μl
[Example 1] Peach flavor type fragrance and flavor imparting composition The following components were mixed as a peach flavor type preparation composition.
[0020]
0.2 parts by weight of (−)-dihydrobobolid was added to the above mixture to obtain a new formulation composition. By adding (−)-dihydrobobolid, a new soft sweetness could be imparted and a milder peach feeling could be reproduced.
[0021]
[Example 2] Saijo flavor type fragrance / flavoring composition The following ingredients were mixed as a Saijo flavor type preparation composition.
[0022]
4.3 parts by weight of (+)-dihydrobobolid was added to the above mixture to obtain a new formulation. By adding (+)-dihydrobobolid, it was possible to give a new deep green feeling and to reproduce the fresh feeling of Saijo.
[0023]
[Example 3] Green tea flavor type fragrance / flavoring composition The following components were mixed as a green tea flavor type preparation composition.
[0024]
0.3 parts by weight of (−)-dihydrobobolid was added to the above mixture to obtain a new formulation composition. By adding dihydrobobolid, it was possible to give a fresh and soft blue color, and to reproduce the freshness of green tea.
[0025]
[Example 4] Black tea type fragrance imparting composition The following components were mixed as a black tea type composition.
[0026]
10 parts by weight of (+)-dihydrobobolid was added to the above mixture to obtain a new formulation. When the prepared composition was scented at a ratio of 0.5% by weight to the body shampoo base material, a herbal floral feeling with a body feeling could be imparted and emphasized.
[0027]
[Example 5] Black tea fragrance imparting composition for perfume The following ingredients were mixed as a composition for black tea for perfume.
[0028]
20 parts by weight of (−)-dihydrobobolid was added to the above-mentioned black tea for perfume composition to obtain a new composition. The perfume composition was made into 10% by weight of alcohol (95% by weight) as a perfume. It was evaluated that it had a fresh green feeling and was emphasized.
[0029]
[Example 6] White floral fragrance imparting composition The following components were mixed as a white floral tuned composition.
[0030]
30 parts by weight of (+)-dihydrobobolid was added to the above mixture to obtain a new formulation composition. When the prepared composition was perfumed at a ratio of 0.9% by weight to the base material for bathing agent, a scent with enhanced jasmine-like floral feeling could be imparted and emphasized.
[0031]
[Example 7] The following components were mixed as a flavor imparting composition flavor flavor composition.
[0032]
0.8 parts by weight of (−)-dihydrobobolid was added to the above mixture to obtain a new formulation composition. When the prepared composition was scented with 0.1% of commercially available tobacco, the lightness of the smoke came out and the tobacco flavor could be imparted and emphasized.
[0033]
【The invention's effect】
According to the invention, (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and / or (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone A novel aroma / flavoring / flavoring imparting composition is obtained. (+)-3,4-dimethyl-5-pentyl-2 (5H) -furanone and / or (−)-3,4-dimethyl-5-pentyl-2 (5H) -furanone has an aroma and flavor imparting composition. It is particularly excellent as a component of products and is particularly suitable for enhancing the characteristics of added foods, perfumes and cosmetics.
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