A decanoic acid 4-methyl-5-thiazole ethanethiol ester flavor
The preparation of 4-methyl-5-thiazol ethyl mercaptan ester of decanoic acid solved the problem of insufficient types of sulfur-containing ester flavorings, and achieved diversified flavor enhancement of food flavorings.
Patent Information
- Application Number
- CN202510026585.2
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-01-08
- Publication Date
- 2026-07-10
AI Technical Summary
The limited variety of sulfur-containing flavorings available makes it difficult to meet consumers' demand for diverse food flavors.
A novel sulfur-containing ester compound, decanoic acid 4-methyl-5-thiazole ethyl mercaptan ester, was developed, prepared and characterized by a specific synthetic route, exhibiting characteristic aromas of meat, roast, caramel and vegetables.
A novel sulfur-containing ester flavoring with rich aroma characteristics is provided, which enhances the realism and diversity of food flavorings.
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Figure CN122355973A_ABST
Abstract
Description
Technical Field
[0001] This invention relates to an aromatic compound, which is mainly used in food flavorings. Background Technology
[0002] Flavorings are the raw materials for formulating flavorings; only with a rich variety and high-quality flavorings can high-quality flavoring products be obtained. Sulfur-containing flavorings are a very important class of food flavorings. Although they are usually present in food at very low concentrations, they make a significant contribution to the characteristic flavors of many foods. Due to their low aroma threshold, rich aroma, and strong aroma characteristics, sulfur-containing flavorings have been widely used in the formulation of food flavorings, greatly improving the realism of the flavors. Therefore, conducting research on the development and application of new varieties of sulfur-containing flavorings is of great significance for promoting the development of the food flavoring industry.
[0003] Sulfur-containing esters are an important class of sulfur-containing flavorings, chemically stable, and widely used in food flavorings. Although some sulfur-containing ester flavorings are already widely used, there is still a need to continuously develop new varieties of sulfur-containing ester flavorings and formulate flavorings with various aroma profiles that possess natural food flavors to meet the diverse aroma demands of consumers. Summary of the Invention
[0004] The purpose of this invention is to provide a compound that is primarily used in food flavorings.
[0005] More specifically, the present invention relates to the compound 4-methyl-5-thiazolyl decanoate, which is represented by the following general formula:
[0006] Detailed Implementation
[0007] Example 1. Preparation of 4-methyl-5-thiazolyl decanoate
[0008] The synthesis route is shown in the following formula:
[0009]
[0010] To a 50 mL three-necked flask, add decanoic acid (0.345 g, 2.0 mmol), EDC (1-ethyl-(3-dimethylaminopropyl)carbodiimide) (0.384 g, 2.5 mmol), DMAP (4-dimethylaminopyridine) (0.025 g, 0.2 mmol), and acetonitrile (1 mL). Evacuate the reaction mixture to a vacuum and backfill three times with nitrogen. Under nitrogen protection, add dropwise a 25 mL solution of acetonitrile containing 0.337 g, 2.1 mmol of 4-methyl-5-thiazolylethanethiol to the reaction mixture. After the addition is complete, continue stirring the reaction mixture at room temperature for 24 hours. After the reaction was complete, the reaction solution was transferred to a 50 mL single-necked round-bottom flask and rotary evaporated to remove acetonitrile. Then, 10% hydrochloric acid solution (added until the aqueous phase was acidic) and dichloromethane (20 mL) were added to the single-necked flask and stirred for 10 min. The mixture was separated, dried, and rotary evaporated to obtain the crude product, which was then separated by column chromatography (200-300 mesh silica gel, developing solvent: petroleum ether: ethyl acetate = 3:1, eluent: petroleum ether: ethyl acetate = 9:1). 0.355 g of a colorless liquid was obtained, with a yield of 56.7%.
[0011] The product was characterized by 1H NMR and 1C NMR.
[0012] 1 H NMR (300MHz, CDCl3) δ0.84(t,J=6.9,3H),1.18-1.39(m,12H),1.58-1.74(m,2H),2.39(s,3H),2.52(t,J=7.5,3H),2.96-3.07(m,4H),8.54(s,1H).
[0013] 13 C NMR (75MHz, CDCl3) δ14.0,14.8,22.6,25.5,26.5,28.8,29.1,29.1,29.3,30.0,31.7,44.1,129.0,149.4,149.6,199.0.
[0014] Example 2. Aroma Evaluation
[0015] Take 0.01g of decanoic acid 4-methyl-5-thiazolyl ethyl mercaptan ester sample to prepare a 1% propylene glycol solution. Dip a small amount of the solution into the fragrance evaluation strip and smell the fragrance on the strip in the absence of other odor interference to evaluate the aroma.
[0016] The 4-methyl-5-thiazole ethyl mercaptan ester sample of decanoic acid has a meaty aroma, a roasted aroma, a caramel aroma, and a vegetable aroma.
Claims
1. An aromatic compound, 4-methyl-5-thiazolyl decanoic acid, with the following specific chemical structural formula: