23328-62-3

Usage

Uses

Used in Flavor Industry:
2-Methylthioacetaldehyde is used as a flavoring agent for its unique taste characteristics, which contribute to the alliaceous and vegetative flavor profile with a good mouthfeel. It is particularly useful in enhancing the flavor of various food products.
Used in Food Industry:
2-Methylthioacetaldehyde is used as an additive in the food industry to impart a rich, onion and garlic-like taste with a subtle potato and bready nuance. It is commonly found in products such as tomato, potato chips, coffee, and malt, where it helps to create a more complex and appealing flavor profile.
Used in Fragrance Industry:
2-Methylthioacetaldehyde can also be used in the fragrance industry as a component in creating various scent profiles. Its unique taste characteristics can be translated into a distinct olfactory experience, making it a valuable addition to the perfumer's palette.

Preparation

By hydrolysis of the diethyl acetal of 2-methyl thioacetaldehyde with diluted HCl; the diethyl acetal is prepared from diethylbromoacetal treated with sodium methyl mercaptide

InChI:InChI=1/C3H6OS/c1-5-3-2-4/h2H,3H2,1H3

Upstream product

• 4819-74-3 1,1-diethoxy-2-methylthioethane 
• 19651-44-6 S-methyl-DL-cysteine 
• 16630-66-3 methyl 2-(methylthio)acetate 
• 101010-52-0 dimethyl(1-chloro-2-hydroxyethenyl)sulfonium chloride 
• 40015-15-4 1,1-dimethoxy-2-methylsulfanyl-ethane 

Downstream Products

• 7714-93-4 1-hydroxy-1-phenyl-2-methylthioethane 
• 113681-46-2 (Z)-5-Methylthiopent-3-en-2-one 
• 113681-61-1 (E)-5-Methylthiopent-3-en-2-one 
• 98827-08-8 7-(1-hydroxy-2-methylthioethyl)-2,2-dimethyl-3-oxa-7-phenylthio-1-azabicyclo<4.2.0>octan-8-one 
• 79428-35-6 [2-Methylsulfanyl-1-(3-phenyl-thioureido)-ethyl]-phosphonic acid diphenyl ester 

Relevant academic research and scientific papers

Photoinduced electron transfer, decarboxylation, and radical fragmentation of cysteine derivatives: A chemically induced dynamic nuclear polarization study

The photoreactions of cysteine derivatives I with 4-carboxybenzophenone in D2O were investigated by measurements of chemically induced dynamic nuclear polarization (CIDNP). The quenching mechanism is electron transfer from sulfur at every pH; even if the amino group of I is deprotonated, electron transfer from nitrogen does not participate. Decarboxylation of I?+ to give α-aminoalkyl radicals V? occurs on the CIDNP time scale and causes strong cooperative effects. The decarboxylation rate is increased significantly by deprotonation of the amino function; this is due to product control. V? decays by two competing pathways. Fragmentation of the Cβ - S bond in V? yields vinylamine, which is hydrolyzed to acetaldehyde at pH ? 7.25, and thiyl radicals, which then attack the sensitizer to give combination products. Oxidation of V? by ground-state sensitizer leads to sulfur-containing aldehydes or other products, depending on pH. Relative rates of fragmentation and oxidation were determined from CIDNP signal intensities. From the temperature dependence of the polarizations, the activation energy of β-fragmentation was estimated to be 54 kJ mol-1.

USE OF PHYSIOLOGICAL COOLING ACTIVE INGREDIENTS, AND COMPOSITIONS COMPRISING SUCH ACTIVE INGREDIENTS

The invention relates primarily to a method of modulation, preferably of in vitro and/or in vivo modulation, of the cold menthol receptor TRPM8, wherein the receptor is contacted with at least one modulator selected from the group consisting of the compounds of the structure type 1 described herein. The present invention further relates to corresponding uses and compositions comprising such compounds.

Introduction of methionine mimics on 3-arylthiophene: Influence on protein farnesyltransferase inhibition and on antiparasitic activity

In the course of our search for new protein farnesyltransferase inhibitors with antiparasitic activity, we found that addition of a methionine residue at position 2 of 3-arylthiophenes greatly improved enzyme inhibition. To investigate the influence of this methionine residue on FTase and antiparasitic activities, 29 novel tetrasubstituted thiophenes bearing methionine or analogous moieties were synthesised. These new derivatives were evaluated on human and Trypanosoma brucei protein farnesyltransferases and on proliferation of 4 protozoan parasites: Plasmodium falciparum, Trypanosoma brucei brucei, Trypanosoma cruzi and Leishmania donovani. Some compounds showed promising low micromolar or submicromolar activities on T. b. brucei and L. donovani confirming the potential of this new class as antiparasitic agents.

Studies on umami taste. Synthesis of new guanosine 5′-phosphate derivatives and their synergistic effect with monosodium glutamate

A number of N2-alkyl and N2-acyl derivatives of guanosine 5′-phosphate (GMP) have been synthesized and tested for their synergistic effect with monosodium L-glutamate (MSG), the prototypical substance imparting umami taste to savory-based foods. Capacities to enhance the taste intensity of MSG (γ values) were estimated through subjective comparisons of MSG/nucleotide mixtures in water with appropriate solutions of MSG alone. Assuming β = γ[nucleotide]/γ[IMP], β values of the N 2-substituted GMPs were found in the range 1.2-5.7. Such values appear to be related to the chain length of the substituent in the 2-position of the purine nucleus and dependent on the replacement of a CH2 group with an S atom and/or with an α-CO group. These findings indicate that the exocyclic NHR group of the guanine moiety is actively implicated in the synergism between GMP derivatives and MSG. Theoretical calculations suggest that an anti conformation is probably assumed by ribonucleotide molecules interacting with umami receptors.

Phosphorus protecting groups

In certain embodiments of the invention, novel compositions having a phosphorus group and a phosphorus protecting group bound to the phosphorus group are provided, and methods of deprotecting the phosphorus group are provided.

TRICYCLIC DELTA OPIOID MODULATORS

The invention is directed to delta opioid receptor modulators. More specifically, the invention relates to tricyclic δ-opioid modulators. Pharmaceutical and veterinary compositions and methods of treating mild to severe pain and various diseases using compounds of the invention are also described.

Synthesis of Azapeptides by the Fmoc/tert-Butyl/polyamide Technique

A new synthesis of azapeptides for use in the study of a proteolytic enzyme associated with Alzheimer's disease is described.The method utilizes fluoren-9-ylmethoxycarbonyl (Fmoc) amino acid carbazates and hydrazides in the Fmoc/tert-butyl/polyamide technique.The preparation of these compounds is presented.Reaction of Fmoc-amino acid hydrazides with an appropriate aldehyde, followed by reduction, gave fully protected amino acid carbazate dipeptide synthons.These derivatives were used to prepare aza amino acid peptide analogues by reaction with a resin-bound amino group, activated with bis-2,4-dinitrophenyl carbonate in the presence of a base.With this activation of the amino group, hydantoin is formed in a major side-reaction, but the cyclisation could be virtually eliminated by omission of the base from the activation procedure.Upon final trifluoroacetic acid-mediated cleavage of the azapeptide, trifluoroacetylation of the N-terminal serine residue was observed.

Synthesis and Silica Gel Promoted Rearrangement of 5-Methylthio-3-carbo-t-butoxy-pent-3-en-2-one

The title compound 3 obtained by the Knoevenagel condensation of t-butyl acetoacetate (1) with methylthioethanal (2) in the presence of zinc chloride was found to undergo an easy isomerization on silica gel to its β,γ-isomer which exists as a mixture of the keto (4) and enol (5) forms. - Keywords: Knoevenagel Condensation, 5-Methylthio-3-carbo-t-butoxy-pent-3-en-2-one, Rearrangement, Silica Gel, Methylthioethanal

Methylenomycin B: A New Synthesis from a β-Ketophosphonate

Methylenomycin B (1) was prepared from diethyl 2-oxopropanephosphonate (5) in four steps in 26percent yield.The key steps in this synthesis include the Wittig-Horner reaction of 5 with methylthioethanal (7) followed by the 1,4-addition of a propionyl anion equivalent to the α-enone 4 formed affording 4-(methylthiomethyl)-hepta-2,5-dione (3) which is an acyclic precursor of the title antibiotic.

Halogenated Epoxides. 9. Reaction of trans-2,3-Dichlorooxirane with Dimethyl Sulfide

Reaction of trans-2,3-dichlorooxirane (1) with dimethyl sulfide afforded in high yield dimethyl(1-chloro-2-hydroxyethenyl)sulfonium chloride (2a).The latter was converted into 1-chloro-2-methoxy-1-(methylthio)ethene (3b) and into 2-acetoxy-1-chloro-1-(methylthio)ethene (3c) by reaction with diazomethane and with ketene, respectively.Pyrolysis of 2a gave chloro(methylthio)acetaldehyde (4a) and dichloroacetaldehyde (6), along with a series of minor byproducts.