2-furfurylthiol

Structural formula
General
Surname	2-furfurylthiol
other names	Furfuryl mercaptan; 2-furyl methanethiol; 2-furan methanethiol; FEMA 2493 ;
Molecular formula	C 5 H 6 OS
Brief description	colorless, malodorous liquid
External identifiers / databases
EC number	202-628-2
ECHA InfoCard	100.002.390
PubChem	7363
Wikidata	Q5509474
properties
Molar mass	114.17 g mol −1
Physical state	liquid
density	1.128 g cm −3
boiling point	155 ° C
solubility	practically insoluble in water; miscible with ethanol; soluble in oils;
Refractive index	1.531 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 226
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

2-Furfurylthiol is a flavoring substance and one of the main components of the coffee flavor.

Occurrence

The content of 2-furfurylthiol in roasted coffee is 1–2 mg · kg ⁻¹ . About a third of this goes into the hot beverage during coffee preparation. 2-Furfurylthiol has been found in raw and fried chicken, boiled beef, grilled pork, sesame oil, and popcorn along with coffee. The content in cooked meat is 2 to> 100 µg · kg ⁻¹ . This means that 2-furfurylthiol is a main component of the aroma of cooked meat.

Manufacturing

2-Furfurylthiol can be produced by the reaction of 2-furan methanol , thiourea and hydrochloric acid .

In addition, 2-furfurylthiol can also be produced microbially and purchased commercially.

properties

2-Furfurylthiol is a malodorous colorless liquid. In a strong dilution (0.1–1 ppb), their smell is similar to the smell of coffee.

use

2-Furfurylthiol is used in beverages, pastries and sweets, among other things.


Use in various foods
Alcoholic drinks	0.05-1.7 ppm	Sauces	0.20-0.80 ppm
Pastries	4.54-6.14 ppm	Hard candy	24.38 ppm
Spice side dishes	0.10 ppm	Meat products	0.04-0.13 ppm
Frozen dairy products	2.48-3.30 ppm	Non-alcoholic beverages	1.12-1.84 ppm
pudding	1.02-2.35 ppm	Soft candy	2.54-3.55 ppm

safety instructions

The vapors of 2-furan methanethiol can form an explosive mixture with air ( flash point 45 ° C).

Individual evidence

^ Entry on FEMA 2493 in the database of the Flavor and Extract Manufacturers Association of the United States .
↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2-furan methanethiol in the GESTIS substance database of the IFA , accessed on February 11, 2018(JavaScript required) .
↑ ^a ^b ^c ^d ^e ^f Fenaroli, Giovanni: Fenaroli's handbook of flavor ingredients . Sixth ed. Boca Raton 2009, ISBN 978-1-4200-9077-2 .
↑ Data sheet 2-furanmethanethiol, 98% from Sigma-Aldrich , accessed on February 11, 2018 ( PDF ).
↑ ^a ^b Entry on 2-furyl methanethiol. In: Römpp Online . Georg Thieme Verlag, accessed on February 10, 2018.
↑ ^a ^b ^c Eisenbrand, Gerhard; Meyer, Alfred Hagen; Schreier, Peter: Römpp-Lexikon Lebensmittelchemie [M - Z] . 2., completely redesigned. and exp. Ed. Thieme, Stuttgart [u. a.] 2006, ISBN 3-13-736602-X .
↑ Surburg, Horst Panten, Johannes: Common fragrance and flavor materials: preparation, properties and uses. 5th edition. Wiley-VCH, Weinheim 2006, ISBN 3-527-31315-X .

[FEMA2493-1] Entry on FEMA 2493 in the database of the Flavor and Extract Manufacturers Association of the United States .

[GESTIS-2] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on 2-furan methanethiol in the GESTIS substance database of the IFA , accessed on February 11, 2018(JavaScript required) .

[:1-3] ↑ ^a ^b ^c ^d ^e ^f Fenaroli, Giovanni: Fenaroli's handbook of flavor ingredients . Sixth ed. Boca Raton 2009, ISBN 978-1-4200-9077-2 .

[Sigma-4] Data sheet 2-furanmethanethiol, 98% from Sigma-Aldrich , accessed on February 11, 2018 ( PDF ).

[Römpp-5] Entry on 2-furyl methanethiol. In: Römpp Online . Georg Thieme Verlag, accessed on February 10, 2018.

[:0-6] Eisenbrand, Gerhard; Meyer, Alfred Hagen; Schreier, Peter: Römpp-Lexikon Lebensmittelchemie [M - Z] . 2., completely redesigned. and exp. Ed. Thieme, Stuttgart [u. a.] 2006, ISBN 3-13-736602-X .

[7] Surburg, Horst Panten, Johannes: Common fragrance and flavor materials: preparation, properties and uses. 5th edition. Wiley-VCH, Weinheim 2006, ISBN 3-527-31315-X .