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New furyl thioalkanals useful in the flavor industry

A furanyl, methyl technology, applied in the field of compositions or end products derived from said application, can solve problems such as no aldehyde derivatives, no mention or suggestion

Active Publication Date: 2009-08-12
FIRMENICH SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although several 2-methyl-3-mercaptofuran derivatives are described in the prior art for the perfumery industry, in particular the alkyl sulfides described in US 3,933,863 or the sulfanones reported in US 5,145,703, however We find no mention or suggestion of any of the compounds of general formula (I) listed above
To the best of our knowledge, there are no reports in the prior art of any aldehyde derivatives of the above-mentioned kind, nor their potential use in the manufacture of novel perfuming compositions capable of modifying or improving the flavor of edible consumable products

Method used

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  • New furyl thioalkanals useful in the flavor industry
  • New furyl thioalkanals useful in the flavor industry
  • New furyl thioalkanals useful in the flavor industry

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Experimental program
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Effect test

Embodiment 1-8

[0065] Compounds of general formula (I) are synthesized by reactions represented in Scheme 1 using appropriate starting materials. compound

[0066] A. Synthesis of 3-[(2-methyl-3-furyl)thio]aldehyde and 3-methyl-3-[(2-methyl-3-furyl)thio]aldehyde

[0067]As a typical synthesis, according to the ratio given in Table 2, 2-methyl-3-mercaptofuran (hereinafter referred to as MFT), 2-alkenal, distilled water and ethanol were stirred at room temperature for several hours (24-95h). Then, the reaction mixture was extracted with ethyl acetate (2 times), and the organic layer was washed with saturated NaCl solution. The combined organic layers were washed with Na 2 SO 4 Dried and concentrated. Column chromatography (SiO 2 , heptane / diethyl ether 8:2) to obtain the pure compound.

[0068] Table 2 : The preparation condition of 3-methyl-3-[(2-methyl-3-furyl) thio] aldehyde

[0069] Aldehyde / concentration

mMol MFT

mMol water

ml ethanol

ml Stiring t...

Embodiment 9

[0104] Synthesis of 3-[(2-methyl-3-furyl)thio]butyraldehyde via Maillard Reaction Intermediate

[0105]A. Reaction of cysteine ​​with xylose followed by addition of natural crotonaldehyde

[0106] Excess cysteine ​​(2.4g, 20mmole) with xylose (0.3g, 2mmole) and NaH 2 PO 4 (2 g, 100 mmole) reacted. The ingredients were dry blended with Hydromatrix (amorphous carrier; Varian part 198003) (17 g). In an ASE (rapid solvent extraction) cell from Dionex, water (60-70 ml) was added and the mixture was heated to 150°C. The pressure was adjusted to 100 bar with nitrogen during a static period of 30 min. Natural crotonaldehyde (1.4 g, 20 mmole) was added to the crude flavor product released from the pool (pH 6.5). Prior to the addition of crotonaldehyde, an aliquot representing 10% of the reaction mixture was extracted with pentane containing 1 mg / ml n-octylthiol as an internal standard and analyzed by GC-MS. After addition of crotonaldehyde, the same extraction was performed. I...

Embodiment 10

[0120] 3-[(2-Methyl-3-furyl)thio]butyraldehyde as a flavoring ingredient in flavor spices and other Application usage

[0121] The above compounds were added in the amounts indicated in Table 4 to various flavor compositions (source: Firmenich SA, Geneva, Switzerland) having the type of flavor profile indicated in Table 4. The table summarizes in all cases the positive sensory effect observed as a result of blind evaluation compared to known fragrances without the compound of the invention. Evaluation tests were carried out by blind test with aqueous solutions containing the indicated ingredients in the indicated proportions (MSG stands for monosodium glutamate).

[0122] Table 4: Performance of 3-[(2-methyl-3-furyl)thio]butyraldehyde in various flavor-type perfumes (increasing number of asterisks indicates increasing level of perfume improvement).

[0123] inside the spice

[0124] * In application, relative to the total weight of the perfumed consumer product...

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Abstract

The invention relates to new derivatives of 2-methyl-3-furanthiol which are useful as flavoring ingredients to confer meaty, juicy taste to a large variety of edible consumer products, chewing gums and oral care products, without imparting thereto undesirable off- notes typical of prior known furanthiol derivatives. The compounds of the invention are derivatives of 2-methyl-3-furanthiol and obey the general formula (I) wherein R represents a group of formula (II) or (III).

Description

technical field [0001] This invention relates to the flavor industry, and more particularly to novel ingredients capable of imparting useful flavors to foods and other edible consumables. The compounds of the present invention are derivatives of 2-methyl-3-mercaptofuran which conform to the general formula [0002] [0003] where R represents the general formula [0004] [0005] or [0006] [0007] group, R 1 Represents a hydrogen atom or a methyl group, R 2 stands for C 1 ~C 6 straight-chain or branched-chain unsaturated hydrocarbon groups. [0008] The present invention also relates to the use of said compound (I) to impart taste and other organoleptic properties to consumables intended for animal or human consumption, and to compositions or end products resulting from said use. Background technique [0009] Although several 2-methyl-3-mercaptofuran derivatives are described in the prior art for the perfumery industry, in particular the alkyl sulfides des...

Claims

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Application Information

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IPC IPC(8): C07D307/64A23L1/226A23L1/227A23L1/231A23L27/20A23L27/21A23L27/26
CPCA23L1/2275A23L1/22671C07D307/64A23L1/22621A23L1/231A23L27/2022A23L27/2052A23L27/215A23L27/26
Inventor 阿兰·尚特罗克里斯蒂安·斯塔肯曼萨比娜·罗沙弗朗索瓦·本齐
Owner FIRMENICH SA
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