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57124-87-5

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57124-87-5 Usage

Description

2-Methyltetrahydrofuran-3-thiol, also known as 2-Methyl-3-tetrahydrofuranthiol, is a sulfur-containing flavor compound that is colorless to light yellow in appearance. It is primarily used in the food industry for its meaty flavor profile and is also reported to be found in heated pork meat.

Uses

Used in Flavor Industry:
2-Methyltetrahydrofuran-3-thiol is used as a flavor compound for enhancing the meaty aroma in various food products. Its application reason is due to its strong meaty flavor profile, which can significantly improve the taste and aroma of processed meat products and other food items that require a meaty flavor.
Used in Meat Flavorings:
In the meat flavorings industry, 2-Methyltetrahydrofuran-3-thiol is used as a key ingredient to impart a rich, meaty flavor to products. The application reason is its ability to mimic the taste and aroma of cooked meat, making it an essential component in the creation of artificial or imitation meat products, as well as in enhancing the flavor of natural meat products.

Biochem/physiol Actions

Odor at 0.1% PGTaste at 0.1-0.5 ppm

Check Digit Verification of cas no

The CAS Registry Mumber 57124-87-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,7,1,2 and 4 respectively; the second part has 2 digits, 8 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 57124-87:
(7*5)+(6*7)+(5*1)+(4*2)+(3*4)+(2*8)+(1*7)=125
125 % 10 = 5
So 57124-87-5 is a valid CAS Registry Number.
InChI:InChI=1/C5H10OS/c1-4-5(7)2-3-6-4/h4-5,7H,2-3H2,1H3/t4-,5-/m0/s1

57124-87-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methyltetrahydrofuran-3-thiol

1.2 Other means of identification

Product number -
Other names 2-methyloxolane-3-thiol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:57124-87-5 SDS

57124-87-5Synthetic route

C7H12O2S

C7H12O2S

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

Conditions
ConditionsYield
With acetic acid at 20℃; for 0.5h;87%
2-methyl-3-chlorotetrahydrofuran
30672-41-4

2-methyl-3-chlorotetrahydrofuran

3-thioacetoxy-2-methyltetrahydrofuran

3-thioacetoxy-2-methyltetrahydrofuran

potassium thioacetate
10387-40-3

potassium thioacetate

A

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

B

(2S,3S)-2-methyl-tetrahydrofuran-3-thiol

(2S,3S)-2-methyl-tetrahydrofuran-3-thiol

Conditions
ConditionsYield
With sodium methylate In N-methyl-acetamide; methanol; waterA 0.72 g (67%)
B n/a
5-Hydroxy-2-pentanone
1071-73-4

5-Hydroxy-2-pentanone

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: phosphoric acid / 200 °C
2: piperidine / 1 h / 20 °C
3: acetic acid / 0.5 h / 20 °C
View Scheme
4-ethyloctanoyl chloride
16493-81-5

4-ethyloctanoyl chloride

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

C15H28O2S
1236109-83-3

C15H28O2S

Conditions
ConditionsYield
at 70℃; for 4h;94%
5-bromo-2-furancarboxaldehyde
1899-24-7

5-bromo-2-furancarboxaldehyde

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

(±)5-((2-methyltetrahydrofuran-3-yl)thio)furan-2-carbaldehyde

(±)5-((2-methyltetrahydrofuran-3-yl)thio)furan-2-carbaldehyde

Conditions
ConditionsYield
With {NiBr2phan2}; zinc; caesium carbonate In water at 45℃; for 24h; Inert atmosphere; Sealed tube;74%
2-(3-chlorophenyl)-2H-1,2,3-triazole 1-oxide
1454920-50-3

2-(3-chlorophenyl)-2H-1,2,3-triazole 1-oxide

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

2-(3-chlorophenyl)-4-(2-methyltetrahydrofuran-3-ylthio)-2H-1,2,3-triazole

2-(3-chlorophenyl)-4-(2-methyltetrahydrofuran-3-ylthio)-2H-1,2,3-triazole

Conditions
ConditionsYield
With nickel(II) sulphate; caesium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 60℃; for 18h; regioselective reaction;73%
para-dinitrobenzene
100-25-4

para-dinitrobenzene

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

2-methyl-3-((4-nitrophenyl)thio)tetrahydrofuran

2-methyl-3-((4-nitrophenyl)thio)tetrahydrofuran

Conditions
ConditionsYield
With potassium phosphate; 18-crown-6 ether In tetrahydrofuran at 20℃; for 3h;69%
8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carboxylicacid ethyl ester

8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carboxylicacid ethyl ester

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

ethyl 3-(2-methyltetrahydrofuran-3-ylthio)-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carboxylate
1309112-23-9

ethyl 3-(2-methyltetrahydrofuran-3-ylthio)-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carboxylate

Conditions
ConditionsYield
In methanol; chloroform at 20℃;65%
2-(4-methylphenyl)-1,2,3-triazole N-oxide
1431772-07-4

2-(4-methylphenyl)-1,2,3-triazole N-oxide

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

4-(2-methyltetrahydrofuran-3-ylthio)-2-p-tolyl-2H-1,2,3-triazole

4-(2-methyltetrahydrofuran-3-ylthio)-2-p-tolyl-2H-1,2,3-triazole

Conditions
ConditionsYield
With nickel(II) sulphate; caesium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 60℃; for 12h; regioselective reaction;63%
Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine
135248-89-4

Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

Fmoc-Cys(2-methyloxolane-3-thiol)-OH

Fmoc-Cys(2-methyloxolane-3-thiol)-OH

Conditions
ConditionsYield
Stage #1: 3-mercapto-2-methyltetrahydrofuran With N-chloro-succinimide In dichloromethane at -50℃; for 0.25h;
Stage #2: Nα-fluoren-9-ylmethoxycarbonyl-L-cysteine In tetrahydrofuran; dichloromethane at -50℃; for 2h;
60.1%
6-amino-4-fluoronicotinonitrile

6-amino-4-fluoronicotinonitrile

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

6-amino-4-((2-methyltetrahydrofuran-3-yl)thio)nicotinonitrile

6-amino-4-((2-methyltetrahydrofuran-3-yl)thio)nicotinonitrile

Conditions
ConditionsYield
Stage #1: 3-mercapto-2-methyltetrahydrofuran With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;
Stage #2: 6-amino-4-fluoronicotinonitrile In tetrahydrofuran at 20℃;
57%
2-chloro-6-methoxy-3-nitropyridine
38533-61-8

2-chloro-6-methoxy-3-nitropyridine

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

6-methoxy-2-(2-methyltetrahydrofuran-3-ylsulfanyl)-3-nitropyridine

6-methoxy-2-(2-methyltetrahydrofuran-3-ylsulfanyl)-3-nitropyridine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h;48%
8-oxo-8H-acenaphthyleno[1,2-b]pyrrole-9-carbonitrile
846038-96-8

8-oxo-8H-acenaphthyleno[1,2-b]pyrrole-9-carbonitrile

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

3-(2-methyltetrahydrofuran-3-ylthio)-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile
1309112-19-3

3-(2-methyltetrahydrofuran-3-ylthio)-8-oxo-8H-acenaphtho[1,2-b]pyrrole-9-carbonitrile

Conditions
ConditionsYield
With triethylamine In methanol at 0 - 5℃;42%
4-chloro-3-iodoquinoline
590371-90-7

4-chloro-3-iodoquinoline

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

3-iodo-4-(2-methyltetrahydrofuran-3-ylsulfanyl)quinoline
1268468-59-2

3-iodo-4-(2-methyltetrahydrofuran-3-ylsulfanyl)quinoline

Conditions
ConditionsYield
With caesium carbonate In tetrahydrofuran; 1,4-dioxane at 20 - 90℃;
With caesium carbonate In tetrahydrofuran; 1,4-dioxane at 20 - 90℃; for 4h;
3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

(E)-3-[4-(2-methyltetrahydrofuran-3-sulfanyl)quinolin-3-yl]acrylic acid ethyl ester
1310801-64-9

(E)-3-[4-(2-methyltetrahydrofuran-3-sulfanyl)quinolin-3-yl]acrylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate / tetrahydrofuran; 1,4-dioxane / 4 h / 20 - 90 °C
2: palladium diacetate; potassium acetate; tetrabutyl-ammonium chloride / N,N-dimethyl-formamide / 16 h / 110 °C
View Scheme
3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

(E)-3-[4-(2-methyltetrahydrofuran-3-sulfonyl)quinolin-3-yl]acrylic acid ethyl ester
1268468-52-5

(E)-3-[4-(2-methyltetrahydrofuran-3-sulfonyl)quinolin-3-yl]acrylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate / tetrahydrofuran; 1,4-dioxane / 4 h / 20 - 90 °C
2: palladium diacetate; potassium acetate; tetrabutyl-ammonium chloride / N,N-dimethyl-formamide / 16 h / 110 °C
3: acetic acid; peracetic acid / dichloromethane / 0 - 20 °C
View Scheme
3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

3-(4-trifluoromethylphenyl)-4-(2-methyltetrahydrofuran-3-ylsulfanyl)quinoline

3-(4-trifluoromethylphenyl)-4-(2-methyltetrahydrofuran-3-ylsulfanyl)quinoline

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate / tetrahydrofuran; 1,4-dioxane / 4 h / 20 - 90 °C
2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 16 h / 90 °C
View Scheme
3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

3-(4-trifluoromethylphenyl)-4-(2-methyltetrahydrofuran-3-sulfonyl)quinoline
1268468-53-6

3-(4-trifluoromethylphenyl)-4-(2-methyltetrahydrofuran-3-sulfonyl)quinoline

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate / tetrahydrofuran; 1,4-dioxane / 4 h / 20 - 90 °C
2: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / 1,2-dimethoxyethane / 16 h / 90 °C
3: acetic acid; peracetic acid / dichloromethane / 0 - 20 °C
View Scheme
3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

6-methoxy-2-(2-methyltetrahydrofuran-3-ylsulfinyl)-3-nitropyridine

6-methoxy-2-(2-methyltetrahydrofuran-3-ylsulfinyl)-3-nitropyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3 h / 0 °C
View Scheme
3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

6-methoxy-2-((2-methyltetrahydrofuran-3-yl)sulfonyl)-3-nitropyridine

6-methoxy-2-((2-methyltetrahydrofuran-3-yl)sulfonyl)-3-nitropyridine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / N,N-dimethyl-formamide / 12 h / 20 °C
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 20 °C
View Scheme
3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

C20H28O4S

C20H28O4S

Conditions
ConditionsYield
Stage #1: (-)-xanthatin With triethylamine In methanol at 0 - 5℃; for 0.166667h; Michael Addition;
Stage #2: 3-mercapto-2-methyltetrahydrofuran In methanol at 0 - 5℃; Michael Addition;
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine
76880-29-0

N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

Boc-Cys(2-methyloxolane-3-thiol)-Gly-Phe-Leu-NH2

Boc-Cys(2-methyloxolane-3-thiol)-Gly-Phe-Leu-NH2

Conditions
ConditionsYield
Stage #1: Fmoc-Leu-OH With ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃;
Stage #2: With piperidine In N,N-dimethyl-formamide
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine; N-Fmoc L-Phe; 3-mercapto-2-methyltetrahydrofuran Further stages;
N-(fluoren-9-ylmethoxycarbonyl)glycine
29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Leu-OH
35661-60-0

Fmoc-Leu-OH

N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine
76880-29-0

N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine

N-Fmoc L-Phe
35661-40-6

N-Fmoc L-Phe

3-mercapto-2-methyltetrahydrofuran
57124-87-5

3-mercapto-2-methyltetrahydrofuran

Cys-Gly-Phe-Leu-NH2

Cys-Gly-Phe-Leu-NH2

Conditions
ConditionsYield
Stage #1: Fmoc-Leu-OH With ethyl cyanoglyoxylate-2-oxime; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃;
Stage #2: With piperidine In N,N-dimethyl-formamide
Stage #3: N-(fluoren-9-ylmethoxycarbonyl)glycine; N-α-tert-butoxycarbonyl-S-(3-nitro-2-pyridylthio)-L-cysteine; N-Fmoc L-Phe; 3-mercapto-2-methyltetrahydrofuran Further stages;

57124-87-5Downstream Products

57124-87-5Relevant articles and documents

Preparation method and application of 2-methyl tetrahydrofuran-3-thiol

-

Paragraph 0018; 0052; 0053, (2018/09/12)

The invention discloses a preparation method of 2-methyl tetrahydrofuran-3-thiol. According to the preparation method, 5-hydroxy-2-pentanone is used as a raw material, and the 2-methyl tetrahydrofuran-3-thiol is prepared by carrying out a dispersion reaction. The preparation method has the advantages that when the 5-hydroxy-2-pentanone (I) and phosphoric acid are taken as raw materials for preparing 4,5-dihydro-2-methylfuran (II), less isomer is produced, so that the generation of by-products in a reaction process can be effectively reduced, and the product quality is greatly improved; an intermediate 2-methyltetrahydrofuran-3-thiol acetate (III) is obtained by enabling the 4,5-dihydro-2-methylfuran (II) to react with thioacetic acid, and 2-methyltetrahydrofuran-3-thiol is then prepared, so that the preparation route is short in reaction time.

Certain 3-furyl sulfides

-

, (2008/06/13)

Novel 3-sulfur derivatives of furan including alkyl furan-3-thiols and bis(alkyl-3-furyl) sulfides and di- and tetrahydro derivatives thereof having meaty and/or roasted aromas and flavors; processes for producing such 3-sulfur derivatives; novel flavoring compositions containing such derivatives; and novel food compositions containing such derivatives.

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