59303-05-8

Basic information

• Product Name: methylfurfurylthiol,5-methyl-2-furfurylthiol
• Synonyms: methylfurfurylthiol,5-methyl-2-furfurylthiol;2-Furanmethanethiol, 5-methyl-;5-METHYL-2-FURANMETHANETHIOL;5-Methylfurfurylmercaptan;(5-methylfuran-2-yl)methanethiol
• CAS NO: 59303-05-8
• Molecular Formula: C₆H₈OS
• Molecular Weight: 128.19
• Mol File: 59303-05-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 180℃
• Flash Point: 63℃
• Appearance: /
• Density: 1.078
• PKA: 9.62±0.10(Predicted)
• CAS DataBase Reference: methylfurfurylthiol,5-methyl-2-furfurylthiol(CAS DataBase Reference)
• NIST Chemistry Reference: methylfurfurylthiol,5-methyl-2-furfurylthiol(59303-05-8)
• EPA Substance Registry System: methylfurfurylthiol,5-methyl-2-furfurylthiol(59303-05-8)

Safety Data

• Hazardous Substances Data: 59303-05-8(Hazardous Substances Data)

Usage

General Description

Methylfurfurylthiol, also known as 5-methyl-2-furfurylthiol, is a chemical compound with a strong odor that is often described as having notes of coffee, cocoa, and roasted nuts. It is commonly used as a flavoring agent in the food industry, providing a rich and aromatic profile to various food and beverage products. Methylfurfurylthiol is naturally found in certain foods, such as coffee, cocoa, and grilled meat, and is also produced synthetically for use in food and beverage applications. Due to its potent aroma, it is often utilized in small amounts to enhance the overall sensory experience of a product. Additionally, methylfurfurylthiol is known to be a key contributor to the distinctive aroma of roasted coffee and is therefore a valued component in coffee flavorings and aromatics.

Upstream product

• 3857-25-8 2-hydroxymethyl-5-methylfuran 
• 73-34-7 L-rhamnose 
• 52-90-4 L-Cysteine 

Relevant articles and documents

Rotational Conformers of Furan and Thiophene Thioaldehyde Anion Radicals

The radical anions of the four isomeric furan and thiophene thioaldehydes have been obtained by photolysis, in an alkaline medium, of the corresponding thiols in the presence of di-tert-butyl peroxide.The same reaction also yields the four corresponding aldehyde radical anions, starting from the appropriate alcohols.The ESR spectra show that in most cases the two rotational conformers (E and Z) are present at the equilibrium.By means of appropriate methyl-substituted derivatives it has been possible to assign the structure of the two conformers.In the case of the 2-furan and 2-thiophene aldehyde anion radicals it has been found that the conformational preference is the same as that exhibited by the corresponding molecules.

Generation of thiols by biotransformation of cysteine-aldehyde conjugates with baker's yeast

Baker's yeast was shown to catalyze the transformation of cysteine-furfural conjugate into 2-furfurylthiol. The biotransformation's yield and kinetics were influenced by the reaction parameters such as pH, incubation mode (aerobic and anaerobic), and substrate concentration. 2-Furfurylthiol was obtained in an optimal 37% yield when cysteine-furfural conjugate at a 20 mM concentration was anaerobically incubated with whole cell baker's yeast at pH 8.0 and 30 °C. Similarly to 2-furfurylthiol, 5-methyl-2-furfurylthiol (11%), benzylthiol (8%), 2-thiophenemethanethiol (22%), 3-methyl-2-thiophenemethanethiol (3%), and 2-pyrrolemethanethiol (6%) were obtained from the corresponding cysteine-aldehyde conjugates by incubation with baker's yeast. This work indicates the versatile bioconversion capacity of baker's yeast for the generation of thiols from cysteine-aldehyde conjugates. Thanks to its food-grade character, baker's yeast provides a biochemical tool to produce thiols, which can be used as flavorings in foods and beverages.

Identification of Potent Aroma Compounds in Thermally Treated Mixtures of Glucose/Cysteine and Rhamnose/Cysteine Using Aroma Extract Dilution Techniques

Application of an aroma extract dilution analysis on extracts prepared from either thermally treated solutions (20 min, 145 °C) of glucose/cysteine (I) or rhamnose/cysteine (II) led to the identification of 2-furfurylthiol (roasty, coffee-like), 5-acetyl-2,3-dihydro-1,4-thiazine (roasty), 3-mercapto-2-butanone (sulfury, rotten), 3-mercapto-2-pentanone (catty), and 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like) with the highest odor activities among the 34 odor-active volatiles detected in I. In II, 4-hydroxy-2,5-dimethyl-3(2H)-furanone, 3-hydroxy-6-methyl-2(2H)-pyranone (seasoning-like), 5-methyl-2-furfurylthiol (roasty, coffee-like), 2-furfurylthiol, and 5-acetyl-2,3-dihydro-l,4-thiazine appeared with the highest flavor dilution (FD) factors among the 18 compounds detected by HRGC/O. Among the flavor compounds identified, 2-propionyl-2-thiazoline is reported for the first time among the flavors of Maillard model reactions or foods, respectively. The odorant elicited an intense roasty, popcorn-like odor at the low odor threshold of 0.07 ng/L in air.