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Novel lactone compounds and novel ether compounds

A technology of compounds and lactones, applied in the field of new compounds, can solve the problems of changing and not being able to feel the aroma, etc., and achieve the effect of high palatability

Active Publication Date: 2020-11-17
TAKASAGO INTERNATIONAL CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, there is a problem that all fragrance compounds have problems in persistence, and fragrance can hardly be sensed within several hours to a day under diluted conditions, or within 1 to 2 weeks even under undiluted conditions, or the original The fragrance note changes to a different fragrance note than the original fragrance

Method used

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  • Novel lactone compounds and novel ether compounds
  • Novel lactone compounds and novel ether compounds
  • Novel lactone compounds and novel ether compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1 to 16

[0133]

Embodiment 1

[0134] [embodiment 1] the synthesis of 3-methylcitronellal

[0135] The reaction was carried out under nitrogen atmosphere. A 1 L four-necked flask equipped with a dropping funnel was prepared, and copper iodide (27.3 g, 1.05 equiv) and diethyl ether (200 ml) were added to the flask. While stirring the mixture, the temperature inside the system was lowered to 0°C to 5°C. A methyllithium / ether solution (1.13 mol / L, 260 ml, 2.05 equivalents to CuI) was added dropwise through the dropping funnel over one and a half hours. After completion of the dropwise addition, stirring was performed for 30 minutes while maintaining the temperature, and the temperature inside the system was lowered to -60°C or lower. Citral (20.8 g, 137 mmol) and diethyl ether (100 ml) were slowly added dropwise through the dropping funnel over 1 hour. After the dropwise addition was completed, stirring was performed for 1 hour while maintaining the temperature, and the temperature inside the system was gra...

Embodiment 2

[0139] [embodiment 2] the synthesis of 3-ethyl citronellal

[0140] 3-Ethylcitronellal (3.01 g, 16.7 mmol, 67% yield) was obtained from citral (3.70 g, 24.3 mmol) in the same manner as in Example 1 except that ethyl lithium was used instead of methyl lithium.

[0141] 3-Ethylcitronellal

[0142] 1H-NMR (500MHz, CDCl 3 ):δ0.86(3H,t,J=7.5Hz),1.03(s,3H),1.31-1.38(2H,m),1.41(2H,q,J=7.6Hz),1.60(s,3H) , 1.68 (3H, s), 1.90-1.98 (2H, m), 2.27 (2H, d, J = 3.2Hz), 5.00-5.15 (1H, m), 9.85 (1H, t, J = 3.2Hz).

[0143] 13 C-NMR (125MHz, CDCl 3 ):8.0(CH3),17.6(CH3),22.6(CH2),24.8(CH3),25.7(CH3),32.3(CH2),36.2(C),39.6(CH2),52.4(CH2),124.3(CH ), 131.6(C), 203.8(C).

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Abstract

The present invention pertains to a lactone compound represented by general formula (A), and an ether compound represented by general formula (B). [In formula (A), R is a hydrogen atom or R1, R' is R1if R is a hydrogen atom, carbon bond (1) is a single bond or a double bond, and carbon bond (2) is a single bond. If R is R1, then R' is a hydrogen atom or R1, and, among the carbon bonds (1) and (2), both are single bonds, or one is a double bond and the other is a single bond. In formula (B), R'' is R1. R1 can have an optionally-substituted C1-8 alkyl group, an optionally-substituted C2-8 alkenyl group, an optionally-substituted C2-8 alkynyl group, or an aryl group. In formula (A) and formula (B), n is 0 or 1.].

Description

technical field [0001] The present invention relates to novel compounds capable of imparting novel aromas, and flavor or fragrance compositions comprising these compounds. Background technique [0002] In the production of fragrances, there is a wide demand for fragrances having a floral note representing a floral note, or a fragrance having a fruity note representing a fruity note, in particular, peach-like And fragrance compounds like jasmine are very useful. In the related art, most peach-like and jasmine-like fragrance compounds are lactone-based compounds, and γ-nonanolide, γ-decalactone, δ-decalactone, and γ-undecanolide have been Widely used as a spice with a peach-like aroma. In recent years, lactones having double bonds such as Jasmine lactone (ZEON Corporation) and Jasmo lactone (Firmenich S.A.), and frutonile (Givaudan S.A.) and ananthone ( nectaryl) (Givaudan S.A.), and use them as peach-like and jasmine-like fragrance compositions. Contents of the invention...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83A23L27/20A61K8/49A61Q5/02A61Q19/00C07D307/79C07D311/74C11B9/00
CPCA61Q5/02C07D307/79C07D307/83C07D311/74A61K8/4973A61K8/498A61Q13/00A61Q19/10A23L2/00A23L27/2052C11B9/0076C11B9/008A23L2/56
Inventor 伊藤央德松本崇司原田睦
Owner TAKASAGO INTERNATIONAL CORPORATION