Flavor-enhancing amide compounds

A compound and composition technology, applied in the preparation of organic compounds, the preparation of carboxylic acid amides, organic chemistry, etc., can solve the problems of high volatility and strong

Inactive Publication Date: 2011-11-23
INTERNATIONAL FLAVORS & FRAGRANCES
View PDF4 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Unfortunately, menthol also has some undesirable properties, such as strong minty smell, bitter taste and relatively high volatility

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Flavor-enhancing amide compounds
  • Flavor-enhancing amide compounds
  • Flavor-enhancing amide compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I

[0046]

[0047] Pent-4-yn-1-ol 5-iodopent-4-yn-1-ol

[0048] Preparation of 5-iodopent-4-yn-1-ol: Potassium hydroxide (115 g, 2.051 mol, purchased from Sigma-Aldrich) was dissolved in water (150 ml) and cooled to 0°C. Pent-4-yn-1-ol (69 g, 820 mmol, purchased from Sigma-Aldrich) was dissolved in methanol (1.125 L) and slowly added to the reaction mixture while maintaining the temperature at 0 °C. After 15-30 minutes, iodine (229 g, 902 mmol) was added in one portion, and the mixture was warmed to room temperature and stirred for 3 hours. The mixture was then diluted with water (750 mL), and washed with diethyl ether (Et 2 (2, 300 mL) was washed three times. The organic layers were combined and concentrated in vacuo to give a yellow oil. Dissolve the oil in dichloromethane (CH 2 Cl 2 ) (300mL), washed with brine (300mL), sodium sulfate (Na 2 SO 4 ) was dried and filtered. The solvent was removed in vacuo to give crude product (170 g), which was purified by column chr...

Embodiment II

[0051]

[0052] 5-Iodopent-4-yn-1-ol 7-(Trimethylsilyl)heptacarbon-4,6-diyn-1-ol

[0053] Preparation of 7-(trimethylsilyl)heptacarbon-4,6-diyn-1-ol: ethynyltrimethylsilane (112g, 1.143mol, purchased from Sigma-Aldrich Company), piperazine Pyridine (847ml, 8.571mol, purchased from Sigma-Aldrich) and 5-iodopent-4-yn-1-ol (120g, 0.571mol, prepared as described above) were combined and cooled to 0°C. Copper(I) chloride (5.66 g, 57.1 mmol, purchased from Sigma-Aldrich) was added in one portion. The reaction mixture was allowed to warm to room temperature. After 30 minutes, with saturated ammonium chloride solution (NH 4 Cl) (2.5L) to stop the reaction solution, and with Et 2 O (300 mL) was washed three times. The organic layers were combined, washed twice with brine (500 mL), washed with Na 2 SO 4 Dry, filter and concentrate in vacuo with a rotary evaporator. The resulting crude product was purified by silica gel chromatography (Hex:EtOAc 6:1) to give 7-(trimethylsilyl)h...

Embodiment III

[0056]

[0057] 7-(trimethylsilyl)heptacarbon-4,6-diyn-1-ol 7-(trimethylsilyl)heptacarbon-4,6-diynal

[0058] Preparation of 7-(trimethylsilyl)heptacarbon-4,6-diyne aldehyde: Dimethylsulfoxide (DMSO) (76ml, 1.076mol) was added dropwise to oxalyl chloride (47.1ml, 538mmol) at -78°C , purchased from Sigma-Aldrich) CH 2 Cl 2 (750ml) solution. The mixture was stirred at -78°C for 20 minutes. 7-(Trimethylsilyl)heptacarbon-4,6-diyn-1-ol (50 g, 269 mmol, prepared as above) was dissolved in CH 2 Cl 2 (15 mL) and added slowly. The mixture was stirred at -78°C for 1 hour. Triethylamine (225ml, 1.614mol, purchased from Sigma-Aldrich) was added. The reaction mixture was stirred for an additional 80 minutes while slowly warming to room temperature. with saturated NH 4 The reaction mixture was quenched with Cl, separated, and the aqueous portion was washed with CH 2 Cl 2 (200 mL) back-extracted twice. The combined organic layers were washed with Na 2 SO 4 Dry, filter and co...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The present invention has discovered that amide compounds represented by Formula I set forth below have unexpected and advantageous flavor enhancement and modification properties: wherein R and R' is independently selected from the group consisting of H and C1-C10 linear, branched, or cyclic alkyl, alkenyl, alkynyl or aromactic groups. Thus, the amide compounds of the present invention can be used to enhance or modify the flavor of orally consumable compositions, such as foodstuff, chewing gums, dental and oral hygiene products, and medicinal products.

Description

field of invention [0001] The present invention relates to the use of amide compounds to enhance or modify the flavor of orally consumable compositions such as foods, chewing gums, dental and oral hygiene products and pharmaceuticals. Background of the invention [0002] The term umami, derived from the Japanese word for savory or meaty taste, is used to denote the unique overall satiety and savory taste of food. Materials exhibiting taste qualities are often dependent on glutamate solution concentration, an important characteristic of umami taste. Umami is gradually recognized as a fifth taste besides sour, sweet, salty and bitter. Traditional compounds with umami characteristics are monosodium glutamate (MSG), protein hydrolysates, some amino acids, certain nucleotides and phosphates. [0003] MSG is the most widely used "flavor enhancer" material, which increases the perception of "tasty" ingredients. But large amounts of MSG can cause side effects as well as allergic ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/09C07C231/02A23L1/22A61K47/16A23L27/20A23L27/00
CPCA23L1/22614C07C233/09A23L1/22091A23L27/202A23L27/88
Inventor K·邦布瓦拉A·J·杨奇科T·V·约翰K·克劳特Z·刘N·曼纳瓦吴侯Y·杨
Owner INTERNATIONAL FLAVORS & FRAGRANCES
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap