A flavoring of octanoic acid 4-methyl-5-thiazolyl ethyl mercaptan.
By preparing octanoic acid 4-methyl-5-thiazole ethyl mercaptan ester flavoring, the problem of the lack of novel sulfur-containing ester flavorings in the existing technology has been solved, and the diversified flavor enhancement of food flavorings has been achieved.
Patent Information
- Application Number
- CN202510026577.8
- 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 lack of novel sulfur-containing ester flavorings in existing technologies makes it difficult to meet consumers' demand for natural flavors in diverse food flavorings.
A compound, 4-methyl-5-thiazolyl octanoate, was developed, prepared and purified via a specific synthetic route, and is intended for use in food flavorings.
4-Methyl-5-thiazolyl ethyl mercaptan ester has characteristic aromas of meat, roast, caramel, and vegetables, enhancing the realism of food flavorings.
Smart Images
Figure CN122355971A_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 octanoate, which is represented by the following general formula:
[0006] Detailed Implementation
[0007] Example 1. Preparation of 4-methyl-5-thiazolyl octanoate
[0008] The synthesis route is shown in the following formula:
[0009]
[0010] To a 50 mL three-necked flask, add octanoic acid (0.289 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 0.336 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). 0.388 g of a colorless liquid was obtained, with a yield of 68.0%. The product was characterized by 1H NMR and 1C NMR.
[0011] 1 H NMR (300MHz, CDCl3) δ0.84(t,J=6.9,3H),1.24-1.26(m,8H),1.59-1.64(m,2H),2.38(s,3H),2.51(t,J=7.5,3H),2.95-3.06(m,4H),8.53(s,1H).
[0012] 13 C NMR (75MHz, CDCl3) δ13.9,14.8,22.5,25.5,26.4,28.7,30.0,31.5,44.0,129.0,149.4,149.6,199.0.
[0013] Example 2. Aroma Evaluation
[0014] Take 0.01g of octanoic 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.
[0015] The 4-methyl-5-thiazolyl octanoate sample has a meaty aroma, a roasted aroma, a caramel aroma, and a vegetable aroma.
Claims
1. An aromatic compound, octanoic acid 4-methyl-5-thiazolyl ethyl mercaptan ester, with the specific chemical structural formula shown below: