Synthesis and odour evaluation of double‐bond isomers of DAMASCENOLIDE, 4‐(4‐methylpent‐3‐en‐1‐yl)‐2(5H)‐furanone, which has a citrus‐like odour,Flavour and Fragrance Journal

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Synthesis and odour evaluation of double‐bond isomers of DAMASCENOLIDE, 4‐(4‐methylpent‐3‐en‐1‐yl)‐2(5H)‐furanone, which has a citrus‐like odour
Flavour and Fragrance Journal ( IF 2.1 ) Pub Date : 2020-02-18 , DOI: 10.1002/ffj.3568
Yamato Miyazawa _{1,

2} , Teruhisa Ohashi ₁ , Kenji Kawaguchi ₁ , Naoko Tanaka ₁ , Ryo Katsuta ₂ , Arata Yajima ₂ , Tomoo Nukada ₂ , Ken Ishigami ₂

Affiliation

Our group recently isolated 4‐(4‐methylpent‐3‐en‐1‐yl)‐2(5H)‐furanone (DAMASCENOLIDE or MPF), which has a citrus‐like odour, from damask rose (Rosa damascena). DAMASCENOLIDE has two double bonds, and we were interested in how the position and the geometric isomerism of these double bonds change the odour. Therefore, we synthesized eleven novel double‐bond isomers of DAMASCENOLIDE and evaluated their odours. Some of them have similar odours to DAMASCENOLIDE, while many others have different odours such as metallic, tropical and fishy. Especially, a Z‐form double‐bond moiety changed the odour significantly. Regarding the odour intensity, compounds with 2(3H)‐furanone skeleton tend to be stronger than compounds with 2(5H)‐furanone skeleton. From these results, it was found that the position and the geometric isomerism of the double bond greatly affected the odour.

中文翻译：

DAMASCENOLIDE，4-（4-甲基戊-3-3-烯-1-基）-2-（5H）-呋喃酮的双键异构体的合成和气味评估，具有柑橘类气味

我们的小组最近从锦缎玫瑰（Rosa damascena）中分离了具有柑橘味的4-（4-甲基戊-3-烯-1-基）-2-（5 H）-呋喃酮（DAMASCENOLIDE或MPF ）。DAMASCENOLIDE具有两个双键，我们对这些双键的位置和几何异构如何改变气味感兴趣。因此，我们合成了11种新型DAMASCENOLIDE双键异构体并评估了它们的气味。其中一些具有与DAMASCENOLIDE相似的气味，而其他许多则具有不同的气味，例如金属，热带和鱼腥味。特别是，Z形双键部分显着改变了气味。关于气味强度，具有2（3 H）-呋喃酮骨架的化合物往往比具有2（5 H）-呋喃酮骨架。从这些结果，发现双键的位置和几何异构性极大地影响了气味。

更新日期：2020-02-18

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