5-bicyclo[2.2.1]hept-2-enyl-acetate as a scenting and/or flavoring agent

A technology for aroma and flavoring agents, applied in the field of imparting, altering and/or intensifying specific aroma notes and/or tastes, capable of solving problems such as strong changes in sensory properties, affecting human tissue tolerance, etc.

Active Publication Date: 2019-11-22
SYMRISE GMBH & CO KG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] - In general, even small changes in the structural configuration of known fragrances can cause strong changes in the organoleptic properties and affect the tolerance of human tissues

Method used

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  • 5-bicyclo[2.2.1]hept-2-enyl-acetate as a scenting and/or flavoring agent
  • 5-bicyclo[2.2.1]hept-2-enyl-acetate as a scenting and/or flavoring agent
  • 5-bicyclo[2.2.1]hept-2-enyl-acetate as a scenting and/or flavoring agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0164] Embodiment 1: Preparation of 5-bicyclo[2.2.1]hept-2-enyl-acetate (compound formula (I))

[0165] 117 g of dicyclopentadiene and 172 g of vinyl acetate were placed in a 500 ml autoclave and heated to 190° C. in about 30 minutes under an initial nitrogen pressure of 5 bar. Here, the pressure rises to about 13 bar. Stir for a further 7-8 hours at 190°C. After cooling, the crude precipitate was removed from the autoclave and cleaned of low boilers.

[0166] Crude yield: 121 g; distilled with 40cm FKK, bp.: 58°C-60°C / 7mbar

[0167] Yield: 106 g (87.4% of theory), the product consists of exo / endo isomers (19 / 81%). GC evaluation (20mDB-WAX, inner diameter 0.18μm / 60-9-220℃ cold feed system)

[0168] 1 H-NMR (CDCl 3 ): δ6.34(dd, J=5.7,3.0Hz,1H),6.23(dd,J=5.8,2.9Hz,1H),5.99-5.98(m,1H),5.97(dd,J=5.8,2.9 Hz,1H),5.27(ddd,J=8.2,3.8,2.8Hz 1H),4.65(dp,J=7.0,1.1Hz,1H),3.14(h,J=1.9,1.4Hz,1H),2.88( dt,J=3.0,1.4Hz,1H),2.86-2.81(m,2H),2.14(ddd,J=12.2,8.2,3.8Hz,1H),2.04(s,3H),1.70(d...

Embodiment 2

[0172] Embodiment 2: Perfume composition (fragrance substance composition)

[0173]

[0174]

[0175]

[0176] According to the perfumer's opinion, the addition of 0.03% by weight of a compound of formula (I) (such as the product of Example 1) makes the fragrance composition more rounded, natural and harmonious, adding fresh, fruity top notes and strengthening the violet Floral aspect. The compounds of formula (I) give the compositions individuality and combine different odor elements.

Embodiment 3

[0177] Embodiment 3: Perfume composition (perfume composition)

[0178]

[0179]

[0180]

[0181] According to the perfumer's opinion, the addition of 0.6% by weight of a compound of formula (I), such as the product of Example 1, makes the perfume composition stronger and more natural, adding a pronounced melon fruity note. Compounds of formula (I) give compositions a richer character and combine different odor elements.

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PUM

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Abstract

The invention primarily relates to the use of 5-bicyclo[2.2.1]hept-2-enyl-acetate as a scenting and/or flavoring agent. The invention further relates to new scenting and/or flavoring agent compositions comprising 5-bicyclo[2.2.1]hept-2-enyl-acetate, the use thereof, scented and/or flavored articles comprising 5-bicyclo[2.2.1]hept-2-enyl-acetate, and various processes for imparting, modifying and/or enhancing certain fragrances and/or flavors.

Description

technical field [0001] The present invention mainly relates to the use of 5-bicyclo[2.2.1]hept-2-enyl-acetate, ie the compound of formula (I) as described herein, as a fragrance and / or flavoring agent. The present invention also relates to novel fragrance and / or flavoring compositions comprising compounds of formula (I) as described herein, perfumed and / or flavored articles comprising compounds of formula (I) as described herein , and various methods for imparting, altering and / or intensifying a particular note and / or taste. [0002] Further aspects and preferred embodiments of the invention emerge from the following description, the appended examples and especially the appended patent claims. Background technique [0003] While a large number of fragrances and / or flavors already exist, there continues to be a general need in the fragrance and flavor industry for new fragrances and / or flavors. For example, there is a need for fragrances and / or flavors capable of producing ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C11B9/00A23L27/20
CPCC11B9/0046A23L27/203
Inventor 贝恩德·霍尔舍马克·曼斯费尔德
Owner SYMRISE GMBH & CO KG
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