646-01-5

Basic information

• Product Name: 3-METHYLTHIOPROPIONIC ACID
• Synonyms: 3-(Methylsulfanyl)propanoic acid;4-Thiapentanoic acid;Propanoic acid, 3-(methylthio)-;Propionic acid, 3-(methylthio)-;3-METHYTHIOPROPIONIC ACID;3-METHYLTHIO PROPIONATE;3-METHYLTHIOPROPIONIC ACID;3-METHYLMERCAPTOPROPIONIC ACID
• CAS NO: 646-01-5
• Molecular Formula: C₄H₈O₂S
• Molecular Weight: 120.17
• EINECS: 211-460-9
• Mol File: 646-01-5.mol

Chemical Properties

• Melting Point: 16°C
• Boiling Point: 130°C 2mm
• Flash Point: 130°C/15mm
• Appearance: /
• Density: 1.160
• Vapor Pressure: 0.00741mmHg at 25°C
• Refractive Index: 1.4884
• PKA: 4.29±0.10(Predicted)
• BRN: 1743054
• CAS DataBase Reference: 3-METHYLTHIOPROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-METHYLTHIOPROPIONIC ACID(646-01-5)
• EPA Substance Registry System: 3-METHYLTHIOPROPIONIC ACID(646-01-5)

Safety Data

• Statements: 34
• Safety Statements: 26-36/37/39
• RIDADR: 3265
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 646-01-5(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
3-METHYLTHIOPROPIONIC ACID is used as a phytotoxin for its ability to induce blight in plants, specifically as a toxin produced by the cassava pathogen Xanthomonas campestris manihotis. This application can be utilized in the study and management of plant diseases and pathogens.
Used in Pharmaceutical Industry:
3-METHYLTHIOPROPIONIC ACID is used as an intermediate in the study of mammalian methionine metabolism, which can contribute to the development of new drugs and therapies targeting metabolic disorders and related health issues.
Used in Chemical Research:
As a thia fatty acid, 3-METHYLTHIOPROPIONIC ACID can be used as a research compound for understanding the properties and reactions of sulfur-containing organic compounds, potentially leading to advancements in the field of organic chemistry and related industries.

InChI:InChI=1/C4H8O2S/c1-7-3-2-4(5)6/h2-3H2,1H3,(H,5,6)/p-1

Upstream product

• 13327-56-5 3-(methylthio)propanoic acid ethyl ester 
• 74-93-1 methylthiol 
• 107-13-1 acrylonitrile 
• 77-78-1 dimethyl sulfate 
• 107-96-0 3-mercaptopropionic acid 
• 2373-51-5 chloro-methylsulfanyl-methane 
• 54974-63-9 3-(methylthio)propionitrile 
• 868-84-8 S,S-dimethyl dithiocarbonate 
• 79-10-7 acrylic acid 
• 41320-26-7 S-(n-Butyl)-S-methyl dithiocarbonate 
• 74-88-4 methyl iodide 
• 13532-18-8 methyl 3-(methylthio)propionate 
• 7647-01-0 hydrogenchloride 
• 550-44-7 N-methylphthalimide 

Downstream Products

• 13327-56-5 3-(methylthio)propanoic acid ethyl ester 
• 74-93-1 methylthiol 
• 75-18-3 dimethylsulfide 
• 7031-23-4 3-(methylthio)propionyl chloride 
• 13532-18-8 methyl 3-(methylthio)propionate 
• 69884-58-8 CCl₃O₂^(1-) 
• 4198-64-5 2-(2-Methylmercapto-aethyl)-benzimidazol 
• 111-17-1 4-thiaheptane-1,7-dioic acid 
• 4938-00-5 3-((carboxymethyl)thio)propanoic acid 
• 1054611-55-0 C₂₉H₃₆N₄O₄S 
• 1143522-15-9 1-{4-[(4S,5R)-2-(6-tert-Butyl-4-ethoxy-pyridin-3-yl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl]-piperazin-1-yl}-3-methylsulfanyl-propan-1-one 
• 256409-22-0 4-(3-bromo phenyl amine)-6-(3-methylthio propionyl amine)-quinazoline 
• 1203661-73-7 N-[1-(4-trifluoromethoxylphenyl)-1H-4,5,6,7-tetrahydroindazol-4-yl]-3-methylsulfanylpropionamide 

Relevant articles and documents

Preparation method of (2-carboxyethyl) dimethyl sulfonium chloride

The invention belongs to the technical field of feed additives, and particularly relates to a preparation method of (2-carboxyethyl) dimethyl sulfonium chloride, which comprises the following steps: (1) dissolving 3-bromopropionic acid in an organic solvent under stirring conditions, adding sodium methyl mercaptide, carrying out heating reaction, adding water after the reaction finishes, regulating the pH value to 5-6 with hydrochloric acid, and extracting with ethyl acetate; washing an ethyl acetate layer with water after liquid separation, and carrying out rotary evaporation to remove ethylacetate and water to obtain an intermediate 3-(methylthio) propionic acid; and (2) under a stirring condition, adding the intermediate 3-(methylthio) propionic acid synthesized in the step (1) into ethyl acetate, cooling to below 2 DEG C in an ice bath, introducing chloromethane to react, carrying out suction filtration and drying after the reaction is finished to obtain a 2-(carboxyethyl) dimethyl sulfonium bromide crude product, and recrystallizing with absolute ethyl alcohol to obtain the target product (2-carboxyethyl) dimethyl sulfonium chloride. The method is environmentally friendly andeasier to operate, the yield of the synthesized (2-carboxyethyl) dimethyl sulfonium chloride is high, a foul smell pollution production process is abandoned, and the body health of production personnel is guaranteed.

Simple method for preparing 3-methylthiopropionic acid

The invention relates to a simple method for preparing 3-methylthiopropionic acid. The method comprises taking acrylic acid and sodium methyl mercaptide as raw materials for reaction in alkaline aqueous solution at 30-60 DEG C for 2-5, performing acidification by concentrated sulfuric acid and extraction by organic solvent to separate out organic phase, and performing normal-temperature distillation to recover the solvent and reduced-pressure distillation to obtain the 3-methylthiopropionic acid. The simple method for preparing the 3-methylthiopropionic acid is low in cost, simple in operation, high in yield and purity of prepared products and applicable to industrial production.

Chemical differentiation of three DMSP lyases from the marine: Roseobacter group

Dimethylsulfoniopropionate (DMSP) catabolism of marine bacteria plays an important role in marine and global ecology. The genome of Ruegeria pomeroyi DSS-3, a model organism from the Roseobacter group, harbours no less than three genes for different DMSP lyases (DddW, DddP and DddQ) that catalyse the degradation of DMSP to dimethyl sulfide (DMS) and acrylate. Despite their apparent similar function these enzymes show no significant overall sequence identity. In this work DddQ and DddW from R. pomeroyi and the DddP homolog from Phaeobacter inhibens DSM 17395 were functionally characterised and their substrate scope was tested using several synthetic DMSP analogues. Comparative kinetic assays revealed differences in the conversion of DMSP and its analogues in terms of selectivity and overall velocity, giving additional insights into the molecular mechanisms of DMSP lyases and into their putatively different biological functions.

New phthalimide-methionine dyad-based fluorescence probes for reactive oxygen species: Singlet oxygen, hydrogen peroxide, and hypochlorite

Different reactive oxygen species were detected by the molecular probes 1-3 that were composed of the phthalimide fluorophore as reporter and a methionine-derived thioether side-chain as receptor part. The sulfoxides that were formed as the primary oxidation products show strong fluorescence in the blue-green (430-540?nm) spectral region. Self-sensitized oxidation by singlet oxygen is in general inefficient indicating rapid electron-transfer quenching of the excited probe molecules. With hydrogen peroxide as thermal oxidant conversion to the sulfoxides is slow but can be accelerated by addition of titanium(IV) catalysts, whereas hypochlorite as oxidant behaves much more reactive even under uncatalyzed conditions. Singlet oxygen that is generated by energy transfer from the photosensitizer Rose Bengal was detected by sensor 1a with rate constants of >107M–1?s–1, a typical rate constant for the oxidation of thioethers to sulfoxides.

ONIUM SALT, LIQUID COMPOSITION CONTAINING SAID ONIUM SALT AND CELLULOSE, AND CELLULOSE RECOVERY METHOD

The invention relates to an onium salt, a liquid composition containing the onium salt and cellulose, and a method for recovering cellulose. The invention makes it possible to provide an onium salt having an extremely high ability to dissolve cellulose at temperatures of 100° C. or lower. It also makes it possible to provide a liquid composition containing this onium salt and cellulose, as a composition suitable for the recovery of cellulose, and a method for recovering cellulose efficiently by using such a liquid composition containing the onium salt and cellulose.

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.

A mild hydrolysis of esters mediated by lithium salts

When treated with amine bases such as triethylamine and various lithium salts in wet solvents, esters are efficiently hydrolyzed to the corresponding acids in good yields. Esters incorporating an α- or β-heteroatom with respect to the ester carbonyl group are hydrolyzed rapidly even at room temperature. To further demonstrate the usefulness of this method, one example is provided where hydrolysis of acetylated camphorsultam is mediated by LiBr.

Design of potent inhibitors of human β-secretase. Part 1

We describe a novel series of potent inhibitors of human β-secretase. These compounds possess the hydroxyethyl amine transition state isostere. A 2.5 A crystal structure of inhibitor 32 bound to BACE is provided.

'Chemical co-substrate rescue' of phytanoyl-CoA 2-hydroxylase mutants causing refsum's disease

The in vitro catalytic activity of two clinically observed mutants of phytanoyl-CoA 2-hydroxylase, an iron(II)/2-oxoglutarate-dependent oxygenase causing Refsum's Disease, was partially rescued by the use of alternatives to the natural cosubstrate, 2-oxoglutarate; this is the first demonstration of 'chemical co-substrate rescue' of mutations to an enzyme causing human disease.

Synthesis of sulfur-containing tricyclic ring systems by means of photoinduced decarboxylative cyclizations

The intramolecular and intermolecular photoinduced electron transfer reactions of a series of mercaptoacetic acid and mercaptopropionic acid derivatives were investigated. In the intermolecular series, the phthalimidoalkylsulfanylalkylcarboxylates 1a-j and 2 were transformed into the tricyclic ring systems 3a-j and 4, respectively, with high regioselectivities. The mercaptoacetic acid and 2-mercaptopropionic acid derived substrates 1a-g and 2 readily cyclized in good to excellent yields (60-98%) but with low diastereoselectivities (except for 1d), whereas the corresponding 3-mercaptopropionic acid derived substrates 1h-j gave the corresponding tricyclic products 3h-j after prolonged irradiation, but with poor yields (11-20%). The intermolecular version - i.e., photodecarboxylative addition to N-methylphthalimide (5) as electron acceptor - was successful with mercaptoacetic acid, and 2-mercaptopropionic acid substrates 6a-c and the addition products 7a-c were obtained in high yields (57-90%). No addition, however, was observed with 3-(methylsulfanyl)propionic acid (6d). The regioselectivity of decarboxylation proceeded in a controlled manner for the mercaptosuccinic acid derivatives in both the intramolecular (with 8a-c) and the intermolecular (with 9) versions. Comparison between sulfur-activated and nonactivated species (13, 15) or irradiation of la under nonactivating conditions showed that the carboxylate anion in the position ct to the electron-donating sulfur atom acts as a superior leaving group. This efficiency is drastically reduced for carboxylate anions in the β position. With the former substrates, the photochemical cyclization proceeds with high product yields. Quantum yield measurements for decomposition (Φd as a measure for cyclization) supported these observations. CV measurements indicated preorientation prior to electron transfer in the intramolecular pathway.