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Novel spirosesquiterpene compound, flavoring composition and food/drink containing said compound, and method for producing said food/drink

A technology for manufacturing methods and compositions, applied in the field of spirocyclic sesquiterpene compounds, capable of solving problems such as insufficient response

Inactive Publication Date: 2019-10-11
TAKASAGO INTERNATIONAL CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it can be said that the combination of existing fragrance raw materials cannot fully meet the above-mentioned needs, and new technologies that have not been available so far are required for imparting or enhancing a natural feeling.

Method used

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  • Novel spirosesquiterpene compound, flavoring composition and food/drink containing said compound, and method for producing said food/drink
  • Novel spirosesquiterpene compound, flavoring composition and food/drink containing said compound, and method for producing said food/drink
  • Novel spirosesquiterpene compound, flavoring composition and food/drink containing said compound, and method for producing said food/drink

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] (Example 1) Production of the compound of the present invention

[0070] The production method of the compound of the present invention will be specifically described using the following production examples, but the production method of the compound of the present invention is not limited to these production examples.

[0071] It should be noted that, unless otherwise specified, the input of substrates and solvents was performed under a nitrogen stream, and the post-treatment of the reaction solution and purification of the crude product were performed in air. In addition, the purity of the compounds obtained in the following production examples was determined by NMR analysis or gas chromatography analysis.

[0072] In the following production examples, the apparatus and conditions used for the measurement of physical properties are as follows.

[0073] NMR measurement device: AVANCEIII 500 (manufactured by Bruker BioSpin)

[0074] Gas chromatography measurement devic...

manufacture example 1

[0078] (Production Example 1) Synthesis of (3aS, 6S, 7aS)-6-(1-propen-2-yl)hexahydroisobenzofuran-1(3H)-one (4) (Eq.1)

[0079] Eq.1

[0080]

[0081] In a 100mL four-necked round-bottom flask, add palladium acetate (0.72g, 3.2mmol, 0.08 equivalents), dehydrated dichloromethane (40.0mL), 1,4-diphenylphosphinobutane (dppb) (1.37g, 3.2 mmol) and (S)-perillyl alcohol (6.09 g, 40.0 mmol) were stirred at room temperature to prepare a matrix solution. After adding 23.0 mL of the matrix solution to a 100 mL autoclave, the interior was pressurized to 5.0 MPa with a mixed gas containing equimolar amounts of hydrogen and carbon monoxide, and stirred at an external temperature of 110° C. for 9 hours. The autoclave was cooled to room temperature, taking care to release gas components. After filtering the insoluble matter, the reaction solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: toluene / ethyl acetat...

manufacture example 2

[0087] (Production Example 2) Synthesis of (3aS, 6S, 7aR)-7a-allyl-6-(1-propen-2-yl)hexahydroisobenzofuran-1(3H)-one (5) (Eq .2)

[0088] Eq.2

[0089]

[0090] Into a 1000 mL four-necked round bottom flask, diisopropylamine (14.3 mL, 102.0 mmol) and dehydrated tetrahydrofuran (THF) (130 mL) were charged, and cooled in a dry ice-acetone bath. Next, an n-hexane solution (concentration: 1.55 mol / L, 57.9 mL, 89.7 mmol) of n-butyllithium (n-BuLi) was added dropwise using a dropping funnel at such a rate that the internal temperature was kept below -50°C. The resulting solution was warmed up to 0° C. in an ice bath, and stirred at the same temperature for 30 minutes. The resulting pale yellow solution was cooled with a dry ice-acetone bath. Dehydrated THF ( 65mL) solution. After the dropwise addition, dehydrated THF (10 mL) was added to the dropping funnel, and added dropwise to the flask. In the same dropping funnel, a solution of allyl bromide (11.84 g, 97.9 mmol) in deh...

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PUM

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Abstract

The present invention pertains to a compound represented by formula (1) with which it is possible to impart or enhance an aroma and flavor associated with the feeling of a highly natural fruit or fruit juice, or ripeness. The present invention also pertains to a flavoring composition containing said compound, a food / drink containing said compound or said flavoring composition, and a method for producing said food / drink.

Description

technical field [0001] The present invention relates to a novel spirocyclic sesquiterpene compound, a fragrance composition, a food and drink containing the compound, and a method for producing the food and drink. Specifically, it relates to epoxyspirolepechinene (Japanese: エポキシシスピロレペズン) having a woody aroma, a fragrance composition containing the epoxyspirolepechinene (Japanese: エポキシススピロレペズン) as an active ingredient, and production of the food and drink method. Background technique [0002] In recent years, along with diversification of consumer demands for food and beverages, food and beverages with a high sense of luxury and naturalness are required. Color, taste, and aroma are important factors in judging deliciousness and naturalness, but among them, aroma plays a large role, and the demand for fragrances with higher naturalness is increasing. However, it can be said that the above-mentioned needs cannot be fully met only with the combination of existing fragrance raw...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/04A23L2/00A23L2/02A61K8/49A61Q13/00C11B9/00
CPCC07D303/04A23L27/29A23L2/56A23L27/203A23V2002/00C07D303/06
Inventor 千叶真吾仓部朱希瓦谷明宏草野友实横山直太中崎敦夫
Owner TAKASAGO INTERNATIONAL CORPORATION
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