JP3477242B2 - Perfume comprising alkyl 2-acetyl-2-alkenoate - Google Patents
Perfume comprising alkyl 2-acetyl-2-alkenoateInfo
- Publication number
- JP3477242B2 JP3477242B2 JP12493394A JP12493394A JP3477242B2 JP 3477242 B2 JP3477242 B2 JP 3477242B2 JP 12493394 A JP12493394 A JP 12493394A JP 12493394 A JP12493394 A JP 12493394A JP 3477242 B2 JP3477242 B2 JP 3477242B2
- Authority
- JP
- Japan
- Prior art keywords
- fragrance
- acetyl
- perfume
- alkyl
- alkenoate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Landscapes
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Description
【０００１】[0001]
【産業上の利用分野】本発明は香料に関する。さらに詳
しくは、本発明は一般式（１）FIELD OF THE INVENTION This invention relates to perfumes. More specifically, the present invention relates to general formula (1)
【化２】
（式中、Ｒ1は炭素数１〜１０のアルキル基を示し、Ｒ2
は炭素数１〜４のアルキル基を示す）で表される２−ア
セチル−２−アルケン酸アルキルからなる香料およびこ
れを含有する香料組成物に関する。本発明の香料および
香料組成物は食品、化粧品、室内芳香剤などの香料素材
として有用である。[Chemical 2] (In the formula, R 1 represents an alkyl group having 1 to 10 carbon atoms, and R 2
Represents an alkyl group having 1 to 4 carbon atoms) and a fragrance comprising an alkyl 2-acetyl-2-alkenoate and a fragrance composition containing the fragrance. The perfume and the perfume composition of the present invention are useful as a perfume material for foods, cosmetics, indoor air fresheners and the like.
【０００２】[0002]
【従来の技術】従来、本発明化合物（１）に近縁のアル
ケン酸アルキル構造を有する香料として、例えば、下記
式（２）を有する２−アセチル−４−メチル−４−ペン
テン酸エチル（特開平３−４７６７８）が知られてい
る。2. Description of the Related Art Conventionally, as a fragrance having an alkyl alkenoate structure closely related to the compound (1) of the present invention, for example, ethyl 2-acetyl-4-methyl-4-pentenoate (special feature: Kaihei 3-47678) is known.
【０００３】[0003]
【化３】
上記式（２）の化合物は果実様或いは花様でかすかに草
木様のにおいを有し、食品、化粧品などの香料素材とし
て広く用いられている。[Chemical 3] The compound of the above formula (2) has a fruity or flowery and faint plant-like odor and is widely used as a flavoring material for foods, cosmetics and the like.
【０００４】[0004]
【発明が解決しようとする課題】本発明は、さわやかな
グリーン感を伴ったフルーツ様香気を有するすぐれた香
料および香料組成物を提供することを目的とする。SUMMARY OF THE INVENTION It is an object of the present invention to provide an excellent fragrance and fragrance composition having a fruity odor with a refreshing green sensation.
【０００５】[0005]
【課題を解決するための手段】本発明は、前記式（１）
を有する２−アセチル−２−アルケン酸アルキルからな
る香料およびこれを含有する香料組成物よりなる。前記
式（１）には、Ｒ1の結合位置によって、シス、トラン
スの２種の幾何異性体が存在するが、本発明の化合物に
はシス体、トランス体およびそれらの混合物が包含され
る。The present invention is based on the above formula (1).
And a perfume composition containing the same, and a perfume composition containing the same. In the formula (1), there are two geometric isomers, cis and trans, depending on the bonding position of R 1 , and the compounds of the present invention include cis isomers, trans isomers and mixtures thereof.
【０００６】前記式（１）のＲ1およびＲ2の定義におい
て、アルキル基は直鎖状または分枝鎖状のアルキル基を
意味する。Ｒ1の例としては、メチル、エチル、ｎ−プ
ロピル、iso−プロピル、ｎ−ブチル、ｎ−ペンチル、
ｎ−ヘキシル、ｎ−ヘプチル、ｎ−オクチル、ｎ−ノニ
ルなどがあげられる。Ｒ2の例としては、メチル、エチ
ル、ｎ−プロピル、iso−プロピル、ｎ−ブチルなどが
あげられる。前記式（１）の化合物およびその製法は文
献、例えば、Organic Reactions 15, 463, 466 (1967）
に記載されているが、この化合物が香料として使用し得
ることは記載されていない。In the definition of R 1 and R 2 in the above formula (1), the alkyl group means a linear or branched alkyl group. Examples of R 1 are methyl, ethyl, n-propyl, iso-propyl, n-butyl, n-pentyl,
Examples include n-hexyl, n-heptyl, n-octyl, n-nonyl and the like. Examples of R 2 include methyl, ethyl, n-propyl, iso-propyl, n-butyl and the like. The compound of the above formula (1) and its manufacturing method are described in the literature, for example, Organic Reactions 15 , 463, 466 (1967).
However, it is not mentioned that this compound can be used as a perfume.
【０００７】前記式（１）を有する化合物は、さわやか
なグリーン感を伴ったフルーツ様香気を有し、香気組成
物に添加することによってその香料自体の特にグリーン
感を強調し、全体の拡散性を高める性質を有している。
本発明の香料組成物における前記式（１）の化合物の含
有量は、約０.５〜１０重量％であり、約３〜５重量％
とするのが望ましい。本発明の香料組成物は常法にした
がって各香料を溶媒に溶かし、混合することによって製
造される。The compound having the above formula (1) has a fruity odor with a refreshing green sensation, and when added to the fragrance composition, emphasizes particularly the green sensation of the fragrance itself, resulting in an overall diffusivity. Has the property of increasing
The content of the compound of formula (1) in the perfume composition of the present invention is about 0.5 to 10% by weight, and about 3 to 5% by weight.
Is desirable. The fragrance composition of the present invention is produced by dissolving each fragrance in a solvent and mixing them according to a conventional method.
【０００８】また、前記式（１）の化合物は、例えば上
記の文献に記載された方法に従って、式（３）
ＣＨ3ＣＯＣＨ2ＣＯＯＲ2 (３)
（式中、Ｒ2は前述したものと同一意義を有する）を有
する化合物を第２級アミンやピリジンのような塩基の存
在下に、式（４）
Ｒ1−ＣＨＯ (４)
（式中、Ｒ1は前述したものと同一意義を有する）を有
するアルデヒドと混合することによって容易に製造され
る。The compound of the formula (1) can be obtained by the formula (3) CH 3 COCH 2 COOR 2 (3) (wherein R 2 is the same as described above), for example, according to the method described in the above document. Having the meaning) in the presence of a base such as a secondary amine or pyridine, and having the formula (4) R 1 —CHO (4) (wherein R 1 has the same meaning as described above). It is easily prepared by mixing with an aldehyde having
【０００９】[0009]
【実施例】次に参考例および実施例を示して本発明をさ
らに具体的に説明する。
参考例１
アセト酢酸エチル６５ｇのシクロヘキサン（１００ｇ）
溶液に、硫酸マグネシウム存在下、５℃でピロリジン
１.８ｇのシクロヘキサン（５ｇ）溶液を加えた。次い
で、３℃にて、アセトアルデヒド３５ｇのシクロヘキサ
ン（５０ｇ）溶液を滴下した。そのまま２時間撹拌した
後、中和、水洗、分液、さらに減圧濃縮して粗油３９ｇ
を得た。これを精留し２−アセチル−２−ブテン酸エチ
ル１８.５ｇ（収率２４％，シス体：トランス体＝１：
１.５）を得た。EXAMPLES Next, the present invention will be described more specifically by showing reference examples and examples. Reference Example 1 65 g of ethyl acetoacetate cyclohexane (100 g)
A solution of 1.8 g of pyrrolidine in cyclohexane (5 g) was added to the solution at 5 ° C. in the presence of magnesium sulfate. Then, a solution of 35 g of acetaldehyde in cyclohexane (50 g) was added dropwise at 3 ° C. After stirring for 2 hours as it is, neutralized, washed with water, separated, and further concentrated under reduced pressure to give 39 g of crude oil.
Got This was rectified and ethyl 2-acetyl-2-butenoate 18.5 g (yield 24%, cis isomer: trans isomer = 1: 1)
1.5) was obtained.
【００１０】参考例２
アセト酢酸エチル７２ｇのシクロヘキサン（１００ｇ）
溶液に、硫酸マグネシウム存在下、５℃でピロリジン
１.８ｇのシクロヘキサン（５ｇ）溶液を加えた。次い
で、３℃にてヘキサナール５０ｇのシクロヘキサン（５
０ｇ）溶液を滴下した。そのまま２時間撹拌した後、中
和、水洗、分液、さらに減圧濃縮して粗油を得た。これ
を精留し２−アセチル−２−オクテン酸エチル３１ｇ
（収率２６％，シス体：トランス体＝１：１.３）を得
た。Reference Example 2 72 g of ethyl acetoacetate in cyclohexane (100 g)
A solution of 1.8 g of pyrrolidine in cyclohexane (5 g) was added to the solution at 5 ° C. in the presence of magnesium sulfate. Then, at 3 ° C., 50 g of hexanal cyclohexane (5
0 g) solution was added dropwise. The mixture was stirred as it was for 2 hours, neutralized, washed with water, separated, and further concentrated under reduced pressure to obtain a crude oil. This is rectified and 31 g of ethyl 2-acetyl-2-octenoate is obtained.
(Yield 26%, cis isomer: trans isomer = 1: 1.3) was obtained.
【００１１】実施例１
シャンプーやトイレタリー製品のグリーンフルーティー
ノートとして使用されているカシス様ベース香料に、新
たに２−アセチル−２−ブテン酸エチルを３％添加した
処方（Ａ）は、その代わりにジプロピレングリコールを
添加した処方（Ｂ）に比べ、グリーンフルーティー感が
増加し、拡散性が強くなった結果、嗜好性がより上がる
ことが確認された。Example 1 The formulation (A) in which 3% of ethyl 2-acetyl-2-butenoate was newly added to the cassis-like base fragrance used as a green fruity note for shampoo and toiletry products was used instead. It was confirmed that as compared with the formulation (B) to which dipropylene glycol was added, the green fruity feeling was increased and the diffusivity was strengthened, and as a result, the palatability was further improved.
【００１２】[0012]
【表１】 [Table 1]
【００１３】実施例２
液体芳香剤用として使用されているグリーンアップルベ
ースに、新たに２−アセチル−２−オクテン酸エチルを
５％添加した処方（Ａ）は、それを添加しなかった処方
（Ｂ）に比べ、天然のアップルを想起させる爽やかさが
強く表れ、より優れた拡散性を有することが明確になっ
た。このさわやかさと拡散性が嗜好性を増加させるのに
寄与している。Example 2 A formulation (A) in which 5% of ethyl 2-acetyl-2-octenoate was newly added to the green apple base used as a liquid fragrance was a formulation in which it was not added ( Compared with B), the refreshing effect reminiscent of natural apple was strongly exhibited, and it became clear that it has a better diffusion property. This refreshing and diffusive property contributes to increase the preference.
【００１４】[0014]
【表２】 [Table 2]
【００１５】[0015]
【発明の効果】前記式（１）を有する２−アセチル−２
−アルケン酸アルキルからなる香料およびこれを含有す
る香料組成物は、さわやかなグリーン感を伴ったフルー
ツ様香気を有し、香気組成物に添加することによってそ
の香料自体の特にグリーン感を強調し、全体の拡散性を
高める。2-Acetyl-2 having the above formula (1)
-A fragrance consisting of an alkyl alkenoate and a fragrance composition containing the fragrance have a fruit-like odor with a refreshing green sensation, and by adding to the fragrance composition, the fragrance itself is particularly emphasized in green sensation. Improves overall diffusion.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 和泉 健一郎 岡山県勝田郡勝央町太平台１−２ 小川 香料株式会社岡山研究所内 (72)発明者 亀田 弥 岡山県勝田郡勝央町太平台１−２ 小川 香料株式会社岡山研究所内 (56)参考文献 特開 昭52−46022（ＪＰ，Ａ) 特開 平３−184938（ＪＰ，Ａ) 特開 平３−95137（ＪＰ，Ａ) 特開 平３−153646（ＪＰ，Ａ) 特公 平３−47678（ＪＰ，Ｂ２) (58)調査した分野(Int.Cl.7，ＤＢ名) C11B 9/00 A61K 7/46 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)─────────────────────────────────────────────────── ─── Continuation of the front page (72) Kenichiro Izumi Inventor, Taiheidai 1-2, Shoo-cho, Katsuta-gun, Okayama Ogawa Fragrance Co., Ltd. Okayama Laboratory (72) Inventor Ya Kameda 1-2 Taiheidai, Katsuta-cho, Katsuta-gun, Okayama Prefecture Ogawa Fragrance Co., Ltd. Okayama Laboratory (56) Reference JP-A-52-46022 (JP, A) JP-A-3-184938 (JP, A) JP-A-3-95137 (JP, A) JP-A-3- 153646 (JP, A) JP-B 3-47678 (JP, B2) (58) Fields surveyed (Int.Cl. 7 , DB name) C11B 9/00 A61K 7/46 CA (STN) REGISTRY (STN)
Claims (2)
は炭素数１〜４のアルキル基を示す）で表される２−ア
セチル−２−アルケン酸アルキルからなる香料。1. A compound represented by the general formula (1): (In the formula, R 1 represents an alkyl group having 1 to 5 carbon atoms, and R 2
Represents an alkyl group having 1 to 4 carbon atoms) and is a fragrance consisting of alkyl 2-acetyl-2-alkenoate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12493394A JP3477242B2 (en) | 1994-06-07 | 1994-06-07 | Perfume comprising alkyl 2-acetyl-2-alkenoate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12493394A JP3477242B2 (en) | 1994-06-07 | 1994-06-07 | Perfume comprising alkyl 2-acetyl-2-alkenoate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07331278A JPH07331278A (en) | 1995-12-19 |
| JP3477242B2 true JP3477242B2 (en) | 2003-12-10 |
Family
ID=14897766
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12493394A Expired - Lifetime JP3477242B2 (en) | 1994-06-07 | 1994-06-07 | Perfume comprising alkyl 2-acetyl-2-alkenoate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3477242B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0611770D0 (en) | 2006-06-15 | 2006-07-26 | Givaudan Sa | Compounds |
| WO2023247298A1 (en) * | 2022-06-21 | 2023-12-28 | Firmenich Sa | Compositions for preventing, reducing, or ameliorating malodorous aldehydes and ketones, and uses thereof |
-
1994
- 1994-06-07 JP JP12493394A patent/JP3477242B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07331278A (en) | 1995-12-19 |
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