ChemicalBook Product Catalog Flavors and fragrances Synthetic fragrances Carboxylic acids and esters Aromatic carboxylic acid ester ETHYL (METHYLTHIO)ACETATE

ETHYL (METHYLTHIO)ACETATE

Product NameETHYL (METHYLTHIO)ACETATE
CAS4455-13-4
MFC5H10O2S
MW134.2
EINECS224-700-2
MOL File4455-13-4.mol

Chemical Properties

Boiling point	70-72 °C/25 mmHg (lit.)
Density	1.043 g/mL at 25 °C (lit.)
FEMA	3835 \| ETHYL 2-(METHYLTHIO)ACETATE
refractive index	n20/D 1.459(lit.)
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
InChI	1S/C5H10O2S/c1-3-7-5(6)4-8-2/h3-4H2,1-2H3
InChIKey	MDIAKIHKBBNYHF-UHFFFAOYSA-N
SMILES	CCOC(=O)CSC
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
Storage Class	3 - Flammable liquids
Hazard Classifications	Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
ACROS	English
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

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

Chemical Properties

clear colorless to slightly yellow liquid

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

64-17-5

2444-37-3

4455-13-4

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

ETHYL (METHYLTHIO)ACETATE

Chemical Properties

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MSDS

Usage And Synthesis

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