Description
3-(Methylthio)propanol has a powerful sweet soup or meat-like
odor and flavor in high dilution. May be prepared from propylene
chlorhydrin and sodium hydrosulfide.
Chemical Properties
3-(Methylthio)propanol has a powerful, sweet, soup or meat-like odor and flavor in high dilution.
Chemical Properties
Colorless Liquid
Occurrence
Reported found in fermented soy sauce, tomatoes, grape wines, apple, melon, pineapple, asparagus, rye bread,
cheeses, cured pork, beer, cognac, malt whiskey, cider, sherry, coffee, litchi, shrimp and apple brandy
Uses
3-(Methylthio)-1-propanol is used in the meat essence composition.
Uses
3-Methylthiopropanol is used in the meat essence composition.It is also used in meat, potato, and cheese flavorings.
Uses
Used in meat, potato, and cheese flavorings.
Definition
ChEBI: An alkyl sulfide that is propan-1-ol substituted by a methylsulfanyl group at position 3. It is a volatile compound found in wines and produced during fermentation.
Preparation
From propylene chlorhydrin and sodium hydrosulfide
Aroma threshold values
Detection: 0.2 ppb. Aroma characteristics at 1.0%: sulfurous, savory, vegetative raw potato-like, fresh
tomato, metallic anchovy-like with some onion and garlic nuances
Taste threshold values
Taste characteristics at 0.5 ppm: metallic, tomato, potato, anchovy-like with savory brothy and malt-like
nuances.
General Description
3-(Methylthio)-1-propanol is a volatile sulfur flavor compound mainly found in wine and soy sauce.
Synthesis
An excess of 10% sodium borohydride (NaBH4), a reducing agent, was slowly added to 30 mL of the selected solvent at 0°C to form a suspension. Subsequently, 10 g of 3-methylthiopropionaldehyde (MMP) was slowly added dropwise to the above suspension at a temperature controlled below 20 °C. After the dropwise addition, the reaction mixture was stirred at room temperature for 3 to 12 hours. Upon completion of the reaction, HCl solution was added to the reaction solution for hydrolysis. After hydrolysis, water was removed from the reaction solution by evaporation under reduced pressure. The reaction solution was filtered to remove the sodium chloride generated by hydrolysis and the residue was washed with 10 mL of cold methanol solution to further extract the product 3-methylthiopropanol. Finally, methanol was removed by evaporation of the combined mixed solution and filtrate to give pure 3-methylthiopropanol. Note: The solvent may be selected from dichloromethane (CH2Cl2), dimethylformamide (DMF), methanol, 3-methylthiopropanol (or a solvent mixture thereof with a diluent, referred to as "3-methylthiopropanol"), tetrahydrofuran (THF), or water (H2O), and the concentration of 3-methylthiopropanal (MMP) is 100 percent .
References
[1] Journal of Organic Chemistry, 2000, vol. 65, # 26, p. 8933 - 8939
[2] Patent: CN107245043, 2017, A. Location in patent: Paragraph 0032; 0033; 0034; 0035; 0036
