40789-98-8

Basic information

• Product Name: 3-Mercapto-2-butanone
• Synonyms: 3-mercapto-2-butanon;mercapto-3butanone-2;FEMA 3298;2-MERCAPTO-3-BUTANONE;3-MERCAPTO-2-BUTANONE;3-MERCAPTOBUTAN-2-ONE;3-MERCAPTOBUTANONE;3-MERCAPTO-2-BUTANONE 80+%
• CAS NO: 40789-98-8
• Molecular Formula: C₄H₈OS
• Molecular Weight: 104.17
• EINECS: 255-082-2
• Product Categories: Pharmaceutical Raw Materials;thiol Flavor;Alphabetical Listings;Flavors and Fragrances;M-N;Sulfides flavors
• Mol File: 40789-98-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 48-49 °C15 mm Hg(lit.)
• Flash Point: 117 °F
• Appearance: /
• Density: 1.035 g/mL at 25 °C(lit.)
• Vapor Pressure: 6.25mmHg at 25°C
• Refractive Index: n20/D 1.4352
• Storage Temp.: Refrigerator
• PKA: 8.38±0.10(Predicted)
• Sensitive: Light Sensitive
• CAS DataBase Reference: 3-Mercapto-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Mercapto-2-butanone(40789-98-8)
• EPA Substance Registry System: 3-Mercapto-2-butanone(40789-98-8)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• RTECS: EL9050000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 40789-98-8(Hazardous Substances Data)

Usage

Description

3-Mercapto-2-butanone, also known as thiomethyl butanone, is a sulfur-containing flavor compound that is predominantly found in meat and meat products. It is characterized by its meaty aroma and is formed through the Maillard reaction between sugars and amino acids such as cysteine or thiamin, which are recognized precursors for meat-like flavorings. This colorless liquid possesses unique chemical properties that contribute to its distinctive scent and taste.

Uses

Used in Flavor and Fragrance Industry:
3-Mercapto-2-butanone is used as a flavoring agent for imparting meaty and savory notes to various food products. Its ability to mimic the aroma of cooked meat makes it a valuable ingredient in the development of meat-flavored seasonings, sauces, and snacks.
Used in Meat and Meat Product Industry:
In the meat industry, 3-Mercapto-2-butanone is utilized as a flavor enhancer to improve the taste and aroma of meat products. It helps in creating a more authentic and appetizing flavor profile, thereby enhancing the overall consumer experience.
Used in Cosmetics and Personal Care Industry:
3-Mercapto-2-butanone is also employed in the cosmetics and personal care industry as a fragrance ingredient. Its unique scent can be used to create complex and appealing fragrances for a variety of products, including perfumes, colognes, and body care products.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 3-Mercapto-2-butanone can be used as a starting material for the synthesis of various sulfur-containing compounds with potential therapeutic applications. Its unique chemical structure allows for the development of new drugs with specific properties and functions.
Overall, 3-Mercapto-2-butanone is a versatile compound with a wide range of applications across different industries, primarily due to its distinct sulfur-containing properties and its ability to impart meaty and savory flavors.

Preparation

From 2,4,5-trimethyl-2-ethyl-3-thiazoline with butyl and hydrolysis; from oxo-compound with sulfur or polysulfides and ammonia at room temperature.

Biochem/physiol Actions

Taste at 0.3-1.0 ppm

InChI:InChI=1/C4H8OS/c1-3(5)4(2)6/h4,6H,1-2H3

Upstream product

• 431-03-8 dimethylglyoxal 
• 28588-74-1 2-methylfuran-3-thiol 
• 513-86-0 3-hydroxy-2-butanon 
• 61323-21-5 3-acetylthio-2-butanone 
• 52-90-4 L-Cysteine 
• 1262683-58-8 [13C₅]xylose 
• 59-43-8 vitamin B₁ 
• 58-86-6 D-xylose 
• 4091-39-8 3-chloro-2-butanone 
• 87602-19-5 2,2,4,4-Tetramethyl-[1,3]oxathiolan-5-one 

Downstream Products

• 84310-28-1 2-(1-mercaptoethyl)-2,4,5-trimethyl-3-thiazoline 
• 78-93-3 butanone 
• 53475-15-3 D,L-3-(methylthio)-2-butanone 
• 82694-43-7 (4,5-dimethyl-3-phenyl-3H-thiazol-2-ylidene)-phenyl-amine 
• 56157-60-9 2-(benzylthio)-4,5-dimethylthiazole 
• 60633-24-1 (E,Z)-2,4,5-trimethyl-Δ³-thiazoline 
• 112177-97-6 4,5-Dimethyl-2-phenyl-2,5-dihydro-thiophene-3-carboxylic acid methyl ester 
• 92802-34-1 3-(2-Oxo-2-phenyl-ethylsulfanyl)-butan-2-one 
• 2861-48-5 butane-2,3-dione-bis-phenylhydrazone 
• 14559-13-8 methyl 4,5-dimethylthiophene-3-carboxylate 
• 943332-73-8 2-(3-chlorophenyl)-4,5-dimethyl-4-hydroxy-3-[(3-pyridyl)carbonyl]-4,5-dihydrothiophene 
• 1158836-88-4 ethyl 2-(diphenylphosphoryl)-1-methyl-2-[(1-methyl-2-oxopropyl)sulfanyl]ethylidene-1-hydrazinecarboxylate 
• 1403459-91-5 4-mercapto-3-methyl-1-phenylpent-1-yn-3-ol 
• 1415144-53-4 1-(4-bromophenyl)-4-mercapto-3-methylpent-1-yn-3-ol 

Relevant articles and documents

Effect of pH on the maillard reaction of [C]xylose, cystein, and thiamin

The influence of different pH values, ranging from 4.0 to 7.0, on the formation of sulfur volatiles in the Maillard reaction was studied using a model system with [13C5]xylose, cysteine, and thiamin. The use of 13C-labeled xylose allowed, by analysis of the mass spectra, volatiles that incorporated xylose carbons in the molecule from other carbon sources to be discerned. For 2-furaldehyde and 2-furfurylthiol, which were favored at low pH, the labeling experiments clearly indicated that xylose was the exclusive carbon source. On the other hand, xylose was virtually not involved in the formation of 3-mercapto-2-butanone, 4,5-dihydro-2-methyl-3- furanthiol, and 5-(2-hydroxyethyl)-4-methylthiazole, which apparently stemmed from thiamin degradation. Both xylose and thiamin seemed to significantly contribute to the formation of 2-methyl-3-furanthiol, 3-mercapto-2-pentanone, and 2-mercapto-3-pentanone, and therefore different formation pathways must exist for each of these molecules. In general, the pH determined strongly which volatiles were formed, and to what extent. However, the relative contribution of xylose to the C-skeleton of a particular compound changed only slightly within the investigated pH range, when both xylose and thiamin were involved in the formation.

A novel and expeditious approach to thiophene-3-carboxylates

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Evaluation of the Key Odorants in a Thermally Treated Solution of Ribose and Cysteine by Aroma Extract Dilution Techniques

Application of the aroma extract dilution analysis on a solvent extract isolated from a thermally treated solution (145 deg C; 20 min) of cysteine/ribose led to the identification of 2-furfurylthiol, 3-mercapto-2-pentanone, 2-methyl-3-furanthiol, 5-acetyl-2,3-dihydro-1,4-thiazine, 3-mercapto-2-butanone, and bis(2-methyl-3-furyl) disulfide showing the highest flavor dilution factors among the 29 odor-active volatiles.HRGC/olfactometry of decreasing headspace volumes established especially 2-furfurylthiol and 2-methyl-3-furanthiol as important odorants and revealed 2-thenyl mercaptan and ethyl mercaptan as further key contributors to the overall roasty, meatlike, sulfury odor of the model mixture. 5-acetyl-2,3-dihydro-1,4-thiazine, identified for the first time among the volatiles of Maillard model reactions or foods, exhibited an intense roasty, popcorn-like odor at the low odor threshold of 0.06 ng/L of air, which was of the same order of magnitude as those reported in the literature for the roasty-smelling odorants 2-acetyl-1-pyrroline and 2-acetyl-2-thiazoline.Keywords: Aroma extract dilution analysis; nonenzymatic browning; Maillard reaction; ribose; cysteine; flavor; 5-acetyl-2,3-dihydro-1,4-thiazine