ETHYL (METHYLTHIO)ACETATE Chemical Properties

Boiling point:

70-72 °C/25 mmHg (lit.)

Density 

1.043 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.459(lit.)

FEMA 

3835 | ETHYL 2-(METHYLTHIO)ACETATE

Flash point:

139 °F

storage temp. 

2-8°C

form 

clear liquid

color 

colorless

Odor

at 0.10 % in dipropylene glycol. sulfurous green fruity tropical

Odor Type

fruity

biological source

synthetic

Water Solubility 

Miscible with alcohol. Immiscible with water.

Sensitive 

Moisture Sensitive

JECFA Number

475

BRN 

1744999

LogP

1.35

CAS DataBase Reference

4455-13-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 3272 3/PG 3

WGK Germany 

3

HazardClass 

3

PackingGroup 

III

HS Code 

29309090

MSDS

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

ETHYL (METHYLTHIO)ACETATE Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow liquid

Chemical Properties

Ethyl-2-(methylthio)acetate has a fruity odor.

Occurrence

Reported found in melon, apple, pineapple, durian, yellow passion fruit and kiwifruit.

Uses

Ethyl (methylthio)acetate is used as an internal standard during the analytical determination of volatile sulfur compounds in port wines. Further, it is used as food flavors.

Uses

Ethyl (methylthio)acetate was used as internal standard during the analytical determination of volatile sulfur compounds in port wines.

Definition

ChEBI: Ethyl 2-(methylthio)acetate is a carboxylic ester.

Aroma threshold values

Detection: 250 ppb. Aroma characteristics at 1.0%: sweet, ethereal, rummy with a fruity sulfureous note, slightly vegetative cauliflower with a garlic nuance.

Taste threshold values

Taste characteristics at 1 to 2 ppm: sweet, fruity melon with an uplifting rummy undertone.

General Description

Natural occurrence: Apple and melon.

Biochem/physiol Actions

Taste at 1-2 ppm

Synthesis

Toluene (30 mL), ethanol (2.39 g, 169.59 mmol), and 2-(methylthio)acetic acid (15 g, 141.32 mmol) were sequentially added to a 100 mL round-bottomed flask at room temperature, followed by the addition of p-toluenesulfonic acid monohydrate (4.03 g, 21.20 mmol) as a catalyst. The reaction mixture was gently heated to reflux and the dehydration reaction was carried out for 3 to 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature, followed by addition of triethylamine (2.86 g, 28.26 mmol) to neutralize the acidic catalyst and silica gel for adsorption. After brief stirring, the silica gel was removed by filtration. The filtrate was distilled under reduced pressure to remove the solvent and finally purified by distillation to give ethyl (methylthio)acetate (14.81 g, 78% yield).

References

[1] Patent: US2010/324314, 2010, A1. Location in patent: Page/Page column 15-16
[2] Combinatorial Chemistry and High Throughput Screening, 2011, vol. 14, # 2, p. 132 - 137

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