JPH08113795A - Perfume composition - Google Patents
Perfume compositionInfo
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- JPH08113795A JPH08113795A JP24963294A JP24963294A JPH08113795A JP H08113795 A JPH08113795 A JP H08113795A JP 24963294 A JP24963294 A JP 24963294A JP 24963294 A JP24963294 A JP 24963294A JP H08113795 A JPH08113795 A JP H08113795A
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は下記式（化１）The present invention relates to the following formula (Formula 1)
【化２】 （式中、Ｒ1 およびＲ2 は前記したと同義）で表される
２−アシルオキシ−３−メチル酪酸アルキルエステル類
を有効成分として含有する香料組成物に関する。更に詳
しくは、本発明は持続性のある花様、果実様、草様等の
香気香味特性を有する前記式（化１）の化合物を飲食品
類、嗜好品類、香粧品類などの消費商品に配合すること
により、該商品に花様、果実様、草様の香気香味特性を
付与することのできる持続性香料組成物に関する。Embedded image (In the formula, R 1 and R 2 have the same meanings as described above) The present invention relates to a fragrance composition containing 2-acyloxy-3-methylbutyric acid alkyl ester as an active ingredient. More specifically, the present invention blends the compound of the above formula (Formula 1) having persistent flower-like, fruit-like, grass-like aroma and flavor characteristics into consumer products such as foods and drinks, luxury items and cosmetics. By doing so, the present invention relates to a persistent flavor composition capable of imparting flower-like, fruit-like, or grass-like aroma and flavor characteristics to the product.
【０００２】[0002]
【従来の技術】本発明者らは、２−ヒドロキシ脂肪酸の
エステル誘導体が特異な香気香味特性を有することに着
目して従来から研究を行ってきた。その結果、前記式
（化１）で表される２−アシルオキシ−３−メチル酪酸
アルキルエステル類が持続性のある花様、果実様、草様
等の香気香味特性を有し、調合香料素材として有用であ
ることを見い出し、且つ該化合物を配合した香料組成物
が、香粧品類、飲食品類、嗜好品類、医薬品類などに花
様、果実様、草様の香気香味を付与するのに優れた効果
があることを発見した。2. Description of the Related Art The inventors of the present invention have conventionally conducted research focusing on the fact that ester derivatives of 2-hydroxy fatty acids have unique aroma and flavor characteristics. As a result, the 2-acyloxy-3-methylbutyric acid alkyl ester represented by the above formula (Formula 1) has persistent flower-like, fruit-like, grass-like aroma and flavor characteristics, and is used as a mixed flavoring material. It has been found that it is useful, and that the fragrance composition containing the compound is excellent in imparting a flower-like, fruit-like or grass-like aroma and flavor to cosmetics, foods and drinks, luxury items, pharmaceuticals and the like. I found it effective.
【０００３】前記式（化１）の化合物は、従来の文献[S
ynthetic Communication,21(2),223〜227(1991)]に記載
された公知化合物である。しかしながら、該文献には、
式（化１）化合物の製造方法については記載されている
が、式（化１）化合物についての香気香味特性ならびに
該化合物が調合香料の素材として有用であることなどに
ついては、示唆も言及もされていない。The compound of the above formula (Formula 1) is a compound of the conventional literature [S
Synthetic Communication, 21 (2), 223-227 (1991)]. However, the document states that
Although the method for producing the compound of the formula (1) is described, the aroma and flavor characteristics of the compound of the formula (1) and the usefulness of the compound as a raw material for the prepared perfume are also suggested and mentioned. Not not.
【０００４】[0004]
【発明が解決しようとする課題】近年、消費者の嗜好性
は多様化し、それに伴って各種各様の香気香味を有する
香粧品、嗜好品、飲食品などが製造されている。これら
の多様化に対して、従来公知の香料化合物だけでは各種
各様の香気香味を有する香粧品、嗜好品、飲食品用香料
の需要には対応しきれず、従来にない新しいタイプのユ
ニークな香料素材が強く求められている。In recent years, consumers' tastes have been diversified, and accordingly, cosmetics, tastes, foods and drinks having various aroma and flavor have been manufactured. In response to these diversifications, conventionally known perfume compounds alone cannot meet the demand for perfumes for cosmetics, luxury items and foods and drinks having various flavors, and a new type of unique perfume that has never existed before. There is a strong demand for materials.
【０００５】本発明の式（化１）の化合物は、上述の課
題を解決できる従来にないユニークな香気香味特性を有
し、且つ、その持続性に優れた香料化合物として極めて
有用であることを発見して本発明を完成した。従って、
本発明の目的は、持続性のある花様、果実様、草様等の
香気香味特性を有する前記式（化１）の香料化合物を提
供するにある。また、本発明の他の目的は、該化合物を
調合素材として用いることにより、飲食品類、嗜好品
類、香粧品類などに花様、果実様、草様の香気香味特性
を付与することのできる持続性香料組成物を提供するこ
とにある。The compound of the formula (Chemical formula 1) of the present invention has a unique aroma-flavor characteristic which has not hitherto been able to solve the above-mentioned problems, and is extremely useful as a perfume compound excellent in its durability. Discovered and completed the present invention. Therefore,
An object of the present invention is to provide a fragrance compound of the above formula (Formula 1) having persistent flower-like, fruit-like, grass-like aroma and flavor characteristics. In addition, another object of the present invention is to use the compound as a compounding material to continuously impart a flower-like, fruit-like or grass-like aroma and flavor characteristic to foods and drinks, luxury items, cosmetics and the like. To provide a sex fragrance composition.
【０００６】[0006]
【課題を解決するための手段】本発明によれば、式（化
１）の化合物は、市販品として容易に入手できる２−ヒ
ドロキシ−３−メチル酪酸から二工程で容易に合成する
ことができる。即ち、２−ヒドロキシ−３−メチル酪酸
とメタノール又はエタノールを常法のエステル化法によ
り２−ヒドロキシ−３−メチル酪酸アルキルエステルと
し、次いで該エステルを酢酸、プロピオン酸、酪酸、イ
ソ酪酸、吉草酸、イソ吉草酸等の低級脂肪酸と反応させ
ることにより、前記式（化１）で表される２−アシルオ
キシ−３−メチル酪酸アルキルエステル類を製造するこ
とができる。According to the present invention, the compound of formula (Formula 1) can be easily synthesized in two steps from 2-hydroxy-3-methylbutyric acid, which is easily available as a commercial product. . That is, 2-hydroxy-3-methylbutyric acid and methanol or ethanol are converted into 2-hydroxy-3-methylbutyric acid alkyl ester by a conventional esterification method, and then the ester is converted into acetic acid, propionic acid, butyric acid, isobutyric acid, and valeric acid. , 2-acyloxy-3-methylbutyric acid alkyl ester represented by the above formula (Formula 1) can be produced by reacting with a lower fatty acid such as isovaleric acid.
【０００７】上述のようにして製造できる式（化１）化
合物の具体例としては、２−アセトキシ−３−メチル酪
酸、２−プロピオイルオキシ−３−メチル酪酸、２−イ
ソブチロイルオキシ−３−メチル酪酸、２−ブチロイル
オキシ−３−メチル酪酸、２−イソバレロイルオキシ−
３−メチル酪酸、２−バレロイルオキシ−３−メチル酪
酸等のメチルエステルまたはエチルエステルを挙げるこ
とができる。これらエステル類は、果肉的なフルーツ感
とスイート感を伴った花様、果実様、草様の香気香味特
性を保有し、さらには極めて優れた持続性を有してお
り、各種の香料組成物に添加して利用することができ
る。前記式（化１）の化合物の配合量は、その目的ある
いは香料組成物の種類によっても異なるが、例えば、一
般的には香料組成物の全体量に対して約０. ００１〜約
３０重量％程度の範囲を例示することができる。Specific examples of the compound of the formula (Chemical formula 1) which can be produced as described above include 2-acetoxy-3-methylbutyric acid, 2-propioyloxy-3-methylbutyric acid and 2-isobutyroyloxy-3. -Methyl butyric acid, 2-butyroyloxy-3-methyl butyric acid, 2-isovaleroyloxy-
Mention may be made of methyl esters or ethyl esters such as 3-methylbutyric acid and 2-valeroyloxy-3-methylbutyric acid. These esters have flower-like, fruit-like, and grass-like aroma and flavor characteristics with a fruity fruity and sweet feeling, and further have extremely excellent persistence. Can be used by adding to. The compounding amount of the compound of the formula (Formula 1) varies depending on its purpose or the type of the fragrance composition, but is generally about 0.001 to about 30% by weight relative to the total amount of the fragrance composition. The range of degree can be illustrated.
【０００８】かくして、本発明によれば、前記式（化
１）の化合物を有効成分として配合することにより、果
肉的なフルーツ感とスイート感を伴った花様、果実様、
草様の香気香味特性を付与する新規香料組成物を提供す
ることができ、該組成物を利用して式（化１）の化合物
を香気成分として含有することを特徴とする香粧品類、
式（化１）の化合物を香気香味成分として含有すること
を特徴とする嗜好品類や飲食品類、式（化１）の化合物
を香気香味成分として含有することを特徴とする保健・
衛生・医薬品などを提供することができる。Thus, according to the present invention, by adding the compound of the above formula (Formula 1) as an active ingredient, a flower-like, fruit-like, fruity fruity and sweet feeling,
It is possible to provide a novel fragrance composition imparting grass-like odor and flavor characteristics, and using the composition, a cosmetic comprising the compound of the formula (Chemical formula 1) as an odor component,
Nourishment products and foods and drinks characterized by containing the compound of formula (Formula 1) as an aroma and flavor component, and health care characterized by containing the compound of formula (Formula 1) as an aroma and flavor component.
We can provide hygiene and medicine.
【０００９】例えば、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
他の化粧料基剤や洗剤基剤などに、そのユニークな香気
を付与できる適当量を添加した化粧品類を提供できる。
また、例えば、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にそ
のユニークな香気香味を付与できる適当量を添加した飲
食品類を提供できる。さらにまた、洗濯用洗剤類、消毒
用洗剤類、室内芳香剤その他各種の保健・衛生材料類；
医薬品の服用を容易にするための矯味、賦香剤などの保
健・衛生・医薬品類を提供できる。For example, soaps, body shampoos, shampoos / rinses, detergents, hair creams, pomades, and other hair cosmetic bases; oscilloscopes, lipsticks, other cosmetic bases and detergent bases, etc. It is possible to provide cosmetics containing an appropriate amount capable of imparting the unique aroma.
Further, for example, beverages such as fruit juice drinks, fruit liquors, milk drinks, carbonated drinks; ice creams, sorbets, frozen desserts such as ice candy; Japanese and Western confectioneries, jams, chewing gums, breads, coffee,
Cocoa, black tea, tea and other luxury items; Japanese soups,
It is possible to provide soups such as Western-style soups; foods and drinks in which an appropriate amount capable of imparting a unique aroma and flavor is added to flavor seasonings, various instant drinks or foods, various snack foods, and the like. Furthermore, laundry detergents, disinfecting detergents, indoor air fresheners and various other health and hygiene materials;
It is possible to provide health, hygiene, and pharmaceuticals such as flavoring agents and flavoring agents for facilitating the taking of pharmaceuticals.
【００１０】[0010]
【実施例】以下に本発明について、実施例を挙げて更に
詳細に説明する。 実施例１ シトラスタイプの調合香料組成物として下記の各成分
（重量部）を混合した。 オレンジオイル ８００ α−ピネン ５０ γ−ターピネン ７５ シス−３−ヘキセノール１０％（ＤＰＧ溶液 １５ チモール１０％（ＤＰＧ溶液） ２０ シス−ジャスモン１０％（ＤＰＧ溶液） ２０ メチルメチルアンソラニレート １５ 合計 １０００ 注）ＤＰＧ：ジプロピレングリコールEXAMPLES The present invention will be described in more detail below with reference to examples. Example 1 The following components (parts by weight) were mixed as a citrus-type mixed fragrance composition. Orange oil 800 α-pinene 50 γ-terpinene 75 cis-3-hexenol 10% (DPG solution 15 thymol 10% (DPG solution) 20 cis-jasmon 10% (DPG solution) 20 Methylmethylanthranilate 15 Total 1000 Note) DPG: dipropylene glycol
【００１１】上記組成物９５ｇに２−アセトキシ−３−
メチル酪酸エチルエステルを５ｇ混合して新規調合香料
組成物を調製した。この新規調合香料組成物と該化合物
を加えていない上記のシトラスタイプの調合香料組成物
について、専門パネラー１０人により比較した。その結
果、専門パネラー１０人の全員が該化合物を加えた新規
調合香料組成物は、甘いマイルドな果実感を伴った天然
のシトラスの特徴をとらえ持続性の点でも格段に優れて
いるとした。2-acetoxy-3-in 95 g of the above composition
A novel blended fragrance composition was prepared by mixing 5 g of methyl butyric acid ethyl ester. This newly prepared fragrance composition and the above-mentioned citrus-type prepared fragrance composition containing no compound were compared by 10 expert panelists. As a result, all 10 expert panelists said that the newly-prepared perfume composition to which the compound was added captures the characteristics of natural citrus with a sweet and mild fruity feeling and is also markedly superior in terms of sustainability.
【００１２】実施例２ 実施例１の２−アセトキシ−３−メチル酪酸エチルエス
テルの代わりに２−プロピオイルオキシ−３−メチル酪
酸メチルエステル、２−ブチロイルオキシ−３−メチル
酪酸エチルエステル、２−イソバレロイルオキシ−３−
メチル酪酸メチルエステルをそれぞれ同量混合して各種
の新規調合香料組成物を調製した。これら新規調合香料
組成物と該化合物を加えていない上記のシトラスタイプ
の調合香料組成物について、専門パネラー１０人により
比較した。その結果、専門パネラー１０人の全員が該化
合物を加えた新規調合香料組成物は、甘いマイルドな果
実感を伴った天然のシトラスの特徴をとらえ持続性の点
でも格段に優れているとした。Example 2 In place of 2-acetoxy-3-methylbutyric acid ethyl ester of Example 1, 2-propioyloxy-3-methylbutyric acid methyl ester, 2-butyroyloxy-3-methylbutyric acid ethyl ester, 2-iso Valeroyloxy-3-
Methyl butyric acid methyl ester was mixed in the same amount to prepare various newly prepared fragrance compositions. A comparison was made between these newly prepared fragrance compositions and the above-mentioned citrus-type prepared fragrance compositions containing no compound, by 10 expert panelists. As a result, all 10 expert panelists said that the newly-prepared perfume composition to which the compound was added captures the characteristics of natural citrus with a sweet and mild fruity feeling and is also markedly superior in terms of sustainability.
【００１３】実施例３ リラタイプの調合香料組成物として下記の各成分（重量
部）を混合した。 フェニルエチルアセテート １０ シンナミックアルコール ４０ ターピネオール １３０ シクラメンアルデヒド １０ ヘリオトロピン ５０ シンナミルアセテート １０ カーネーション ２０ リナロール ３０ インドール ２ スチィラックスレジノ ３０ イランイラン １０ ヒドロキシシトロネラール ２９０ ベンジルアセテート ２０ アニスアルデヒド ２０ アブソリュートジャスミ ２０ フェニルエチルアルコール ２７８ アニスアルコール ３０ 合計 １０００Example 3 The following components (parts by weight) were mixed as a lyre-type mixed fragrance composition. Phenylethyl Acetate 10 Cynamic Alcohol 40 Terpineol 130 Cyclamenaldehyde 10 Heliotropin 50 Cinnamyl Acetate 10 Carnation 20 Linalool 30 Indole 2 Styracles Resino 30 Ylang Ylang 10 Hydroxycitronellal 290 Benzyl Acetate 20 Anisaldehyde 20 Absolute Jasumi 20 Phenyl Ethyl alcohol 278 Anise alcohol 30 Total 1000
【００１４】上記組成物９７ｇに２−アセトキシ−３−
メチル酪酸メチルエステルを３ｇ混合して新規調合香料
組成物を調製した。この新規調合香料組成物と該化合物
を加えていない上記のリラタイプの調合香料組成物につ
いて、専門パネラー１０人により比較した。その結果、
専門パネラー１０人の全員が該化合物を加えた新規調合
香料組成物は、ナチュラル感のある甘い花様の特性が強
調され、天然のリラの特徴をとらえ持続性の点でも格段
に優れているとした。2-acetoxy-3-into 97 g of the above composition
A novel fragrance composition was prepared by mixing 3 g of methyl butyric acid methyl ester. This newly prepared fragrance composition and the above-mentioned lyre-type fragrance composition containing no compound were compared by 10 expert panelists. as a result,
The new compounded fragrance composition in which all of the 10 professional panelists added the compound emphasized the characteristic of a sweet flower with a natural feeling, and it was noted that the characteristics of natural lira were also markedly superior in terms of sustainability. did.
【００１５】実施例４ 実施例３の２−アセトキシ−３−メチル酪酸メチルエス
テルの代わりに２−プロピオイルオキシ−３−メチル酪
酸エチルエステル、２−イソブチロイルオキシ−３−メ
チル酪酸エチルエステル、２−バレロイルオキシ−３−
メチル酪酸メチルエステルをそれぞれ同量混合して各種
の新規調合香料組成物を調製した。これら新規調合香料
組成物と該化合物を加えていない上記のリラタイプの調
合香料組成物について、専門パネラー１０人により比較
した。その結果、専門パネラー１０人の全員が該化合物
を加えた新規調合香料組成物は、ナチュラル感のある甘
い花様の特性が強調され、天然のリラの特徴をとらえ持
続性の点でも格段に優れているとした。Example 4 Instead of 2-acetoxy-3-methylbutyric acid methyl ester of Example 3, 2-propioyloxy-3-methylbutyric acid ethyl ester, 2-isobutyroyloxy-3-methylbutyric acid ethyl ester, 2-valeroyloxy-3-
Methyl butyric acid methyl ester was mixed in the same amount to prepare various newly prepared fragrance compositions. These expertly prepared fragrance compositions were compared with the above-mentioned lyre-type fragrance compositions prepared without adding the compound by 10 expert panelists. As a result, the new blended fragrance composition in which all 10 professional panelists added the compound emphasized the characteristic of sweet flower with a natural feeling, and was excellent in terms of sustainability by catching the characteristics of natural lira. I was told.
【００１６】実施例５ パイナップル様の調合香料組成物として下記の各成分
（重量部）を混合した。 エチルアセテート ３００ エチルブチレート ２５０ イソアミルアセテート １００ イソアミルバレレート ５５ イソ酪酸 ７０ イソ吉草酸 ３０ アリルカプロエート ３５ エチルカプロエート ２０ エチルカプリレート １５ エチルカプレート ２０ イソアミルアルコール ３５ ジエチルマロネート ３０ シトラール １５ リナロール ５ マルトール ２０ 合計 １０００Example 5 The following components (parts by weight) were mixed as a pineapple-like mixed fragrance composition. Ethyl acetate 300 Ethyl butyrate 250 Isoamyl acetate 100 Isoamyl valerate 55 Isobutyric acid 70 Isovaleric acid 30 Allylcaproate 35 Ethylcaproate 20 Ethylcaprylate 15 Ethylcaprate 20 Isoamylalcohol 35 Diethylmalonate 30 Citral 15 Linalool 5 Maltor 20 Total 1000
【００１７】上記組成物９４ｇに２−バレロイルオキシ
−３−メチル酪酸エチルエステルを６ｇ混合して新規な
パイナップル様の調合香料組成物を調製した。この新規
調合香料組成物と該化合物を加えていない上記のパイナ
ップル様調合香料組成物について、専門パネラー１０人
により比較した。その結果、専門パネラー１０人の全員
が該化合物を加えた新規調合香料組成物は、甘いマイル
ドな果実感を伴った香気・香味が強調された天然パイナ
ップルの特徴をとらえており、持続性の点でも格段に優
れているとした。A novel pineapple-like fragrance composition was prepared by mixing 6 g of 2-valeroyloxy-3-methylbutyric acid ethyl ester with 94 g of the above composition. This newly prepared fragrance composition was compared with the above-mentioned pineapple-like prepared fragrance composition in which the compound was not added, by 10 expert panelists. As a result, the new compounded fragrance composition in which all 10 professional panelists added the compound captures the characteristics of natural pineapple in which the aroma and flavor are emphasized with a sweet and mild fruity feeling, and is a point of sustainability. However, he said that he was significantly better.
【００１８】実施例６ 実施例５の２−バレロイルオキシ−３−メチル酪酸エチ
ルエステルの代わりに２−イソブチロイルオキシ−３−
メチル酪酸メチルエステル、２−ブチロイルオキシ−３
−メチル酪酸メチルエステル、２−イソバレロイルオキ
シ−３−メチル酪酸エチルエステルをそれぞれ同量混合
して各種の新規調合香料組成物を調製した。これら新規
調合香料組成物と該化合物を加えていない上記のパイナ
ップル様調合香料組成物について、専門パネラー１０人
により比較した。その結果、専門パネラー１０人の全員
が該化合物を加えた新規調合香料組成物は、甘いマイル
ドな果実感を伴った香気・香味が強調された天然パイナ
ップルの特徴をとらえており、持続性の点でも格段に優
れているとした。Example 6 Instead of 2-valeroyloxy-3-methylbutyric acid ethyl ester of Example 5, 2-isobutyroyloxy-3-
Methyl butyric acid methyl ester, 2-butyroyloxy-3
-Methylbutyric acid methyl ester and 2-isovaleroyloxy-3-methylbutyric acid ethyl ester were mixed in the same amounts to prepare various newly-prepared fragrance compositions. These newly prepared flavor compositions were compared with the above-mentioned pineapple-like flavor compositions not containing the compound by 10 expert panelists. As a result, the new compounded fragrance composition in which all 10 professional panelists added the compound captures the characteristics of natural pineapple in which the aroma and flavor are emphasized with a sweet and mild fruity feeling, and is a point of sustainability. However, he said that he was significantly better.
【００１９】[0019]
【発明の効果】本発明によれば、式（化１）で表される
２−アシルオキシ−３−メチル酪酸アルキルエステル類
を有効成分として配合することにより、花様、果実様、
草様等の香気香味特性を有する新規な持続性香料組成物
を提供できる。本発明の式（化１）の化合物は、果肉的
なフルーツ感とスイート感を伴った花様、果実様、草様
の香気香味特性を有しており、該化合物は、嗜好品類、
飲食品類、香粧品類、保健・衛生・医薬品などに用いる
香料組成物の調合素材として有用である。EFFECTS OF THE INVENTION According to the present invention, 2-acyloxy-3-methylbutyric acid alkyl ester represented by the formula (Formula 1) is added as an active ingredient to give a flower-like, fruit-like,
It is possible to provide a novel persistent perfume composition having a fragrant flavor characteristic such as grass. The compound of the formula (Formula 1) of the present invention has flower-like, fruit-like, and grass-like aroma and flavor characteristics with a fruity fruity and sweet sensation.
It is useful as a blending material for perfume compositions used in foods and drinks, perfumes, health care, hygiene, pharmaceuticals and the like.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 畑 久美子 神奈川県川崎市中原区苅宿335 長谷川香 料株式会社技術研究所内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kumiko Hata 335 Kayajuku, Nakahara-ku, Kawasaki City, Kanagawa Prefecture
Claims (1)
Ｃ4 のアルキル基を示す）で表される２−アシルオキシ
−３−メチル酪酸アルキルエステル類を有効成分として
含有することを特徴とする持続性香料組成物。1. The following formula (Formula 1): (R 1 represents an alkyl group of C 1 ~C 2, R 2 is C 1 ~
Sustained perfume composition characterized by containing 2-acyloxy-3-methyl-butyric acid alkyl ester represented by an alkyl group of C 4) as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24963294A JPH08113795A (en) | 1994-10-14 | 1994-10-14 | Perfume composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24963294A JPH08113795A (en) | 1994-10-14 | 1994-10-14 | Perfume composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08113795A true JPH08113795A (en) | 1996-05-07 |
Family
ID=17195920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24963294A Pending JPH08113795A (en) | 1994-10-14 | 1994-10-14 | Perfume composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH08113795A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11512743A (en) * | 1995-10-06 | 1999-11-02 | バーテックス ファーマシューティカルズ インコーポレイテッド | Butyrate prodrug of lactic acid |
| US20110097291A1 (en) * | 2008-06-04 | 2011-04-28 | Firmenich Sa | Fruity odorant |
| WO2020004467A1 (en) * | 2018-06-26 | 2020-01-02 | 三菱瓦斯化学株式会社 | ISOBUTYRIC ACID ESTER COMPOUND HAVING FORMYLOXY GROUP IN α-POSITION, FRAGRANCE MATERIAL COMPOSITION, AND USE AS FRAGRANCE MATERIAL |
| WO2020004465A1 (en) * | 2018-06-26 | 2020-01-02 | 三菱瓦斯化学株式会社 | ISOBUTYRIC ESTER COMPOUND HAVING PROPANOYLOXY GROUP AT α POSITION, PERFUME COMPOSITION, AND USE AS PERFUME |
| WO2020004466A1 (en) * | 2018-06-26 | 2020-01-02 | 三菱瓦斯化学株式会社 | ISOBUTYRIC ESTER COMPOUND HAVING ACETOXY GROUP AT α POSITION, PERFUME COMPOSITION, AND USE AS PERFUME |
| CN112368259A (en) * | 2018-06-26 | 2021-02-12 | 三菱瓦斯化学株式会社 | Isobutyrate compound having butyryloxy group or pivaloyloxy group at alpha-position, and fragrance composition |
| CN113474324A (en) * | 2019-02-27 | 2021-10-01 | 三菱瓦斯化学株式会社 | Isobutyrate compounds having n-butyryloxy group at alpha position, fragrance compositions and use as fragrance |
-
1994
- 1994-10-14 JP JP24963294A patent/JPH08113795A/en active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11512743A (en) * | 1995-10-06 | 1999-11-02 | バーテックス ファーマシューティカルズ インコーポレイテッド | Butyrate prodrug of lactic acid |
| US10766850B2 (en) | 2008-06-04 | 2020-09-08 | Firmenich Sa | Fruity odorant |
| US9957221B2 (en) * | 2008-06-04 | 2018-05-01 | Firmenich Sa | Fruity odorant |
| US11352314B2 (en) | 2008-06-04 | 2022-06-07 | Firmenich Sa | Fruity odorant |
| US10246402B2 (en) | 2008-06-04 | 2019-04-02 | Firmenich Sa | Fruity odorant |
| US20110097291A1 (en) * | 2008-06-04 | 2011-04-28 | Firmenich Sa | Fruity odorant |
| CN102046587A (en) * | 2008-06-04 | 2011-05-04 | 弗门尼舍有限公司 | Fruity odorant |
| WO2020004467A1 (en) * | 2018-06-26 | 2020-01-02 | 三菱瓦斯化学株式会社 | ISOBUTYRIC ACID ESTER COMPOUND HAVING FORMYLOXY GROUP IN α-POSITION, FRAGRANCE MATERIAL COMPOSITION, AND USE AS FRAGRANCE MATERIAL |
| JPWO2020004465A1 (en) * | 2018-06-26 | 2021-07-15 | 三菱瓦斯化学株式会社 | Use as an isobutyric acid ester compound having a propanoyloxy group at the α-position, a fragrance composition, and a fragrance. |
| WO2020004466A1 (en) * | 2018-06-26 | 2020-01-02 | 三菱瓦斯化学株式会社 | ISOBUTYRIC ESTER COMPOUND HAVING ACETOXY GROUP AT α POSITION, PERFUME COMPOSITION, AND USE AS PERFUME |
| WO2020004465A1 (en) * | 2018-06-26 | 2020-01-02 | 三菱瓦斯化学株式会社 | ISOBUTYRIC ESTER COMPOUND HAVING PROPANOYLOXY GROUP AT α POSITION, PERFUME COMPOSITION, AND USE AS PERFUME |
| JPWO2020004467A1 (en) * | 2018-06-26 | 2021-07-08 | 三菱瓦斯化学株式会社 | Use as an isobutyric acid ester compound having a formyloxy group at the α-position, a fragrance composition, and a fragrance. |
| JPWO2020004466A1 (en) * | 2018-06-26 | 2021-08-05 | 三菱瓦斯化学株式会社 | Use as an isobutyric acid ester compound having an acetoxy group at the α-position, a fragrance composition, and a fragrance. |
| US11326125B2 (en) | 2018-06-26 | 2022-05-10 | Mitsubishi Gas Chemical Company, Inc. | Isobutyric ester compound having acetoxy group at alpha-position, fragrance composition, and use thereof as fragrance |
| CN112368259A (en) * | 2018-06-26 | 2021-02-12 | 三菱瓦斯化学株式会社 | Isobutyrate compound having butyryloxy group or pivaloyloxy group at alpha-position, and fragrance composition |
| US11485931B2 (en) | 2018-06-26 | 2022-11-01 | Mitsubishi Gas Chemical Company, Inc. | Isobutyric ester compound having formyloxy group at α-position, fragrance composition, and use thereof as fragrance |
| US11485932B2 (en) | 2018-06-26 | 2022-11-01 | Mitsubishi Gas Chemical Company, Inc. | Isobutyric ester compound having propanoyloxy group at alpha-position, fragrance composition, and use thereof as fragrance |
| CN113474324A (en) * | 2019-02-27 | 2021-10-01 | 三菱瓦斯化学株式会社 | Isobutyrate compounds having n-butyryloxy group at alpha position, fragrance compositions and use as fragrance |
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