3-Methylthiopropanol Chemical Properties

Melting point:

-100°C (estimate)

Boiling point:

89-90 °C13 mm Hg(lit.)

Density 

1.03 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.49(lit.)

FEMA 

3415 | 3-(METHYLTHIO)PROPANOL

Flash point:

195 °F

storage temp. 

Sealed in dry,2-8°C

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

14.87±0.10(Predicted)

form 

liquid (estimate)

Specific Gravity

1.03

color 

Clear Colorless to Light Yellow

Odor

at 0.10 % in propylene glycol. sulfurous onion sweet soup vegetable

Odor Type

meaty

biological source

synthetic

JECFA Number

461

LogP

0.40

CAS DataBase Reference

505-10-2(CAS DataBase Reference)

NIST Chemistry Reference

1-Propanol, 3-(methylthio)-(505-10-2)

EPA Substance Registry System

Methionol (505-10-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-24/25-36/37/39

RIDADR 

UN 3334

WGK Germany 

3

TSCA 

Yes

HS Code 

29309090

MSDS

• Language:English Provider:Methionol
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Methylthiopropanol Usage And Synthesis

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

Colorless Liquid

Chemical Properties

3-(Methylthio)propanol has a powerful, sweet, soup or meat-like odor and flavor in high dilution.

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.

Preparation

From propylene chlorhydrin and sodium hydrosulfide

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.

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.

Synthesis Reference(s)

Tetrahedron, 48, p. 5933, 1992 DOI: 10.1016/S0040-4020(01)90183-8

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

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