59121-24-3

Usage

Uses

Used in Food Industry:
4-(Methylthio)butanenitrile is used as a flavoring agent for its characteristic aroma, which is particularly desirable in the production of pickles. 4-(Methylthio)butanenitrile contributes to the unique taste and smell of these fermented products, enhancing the overall sensory experience for consumers.
As a volatile compound, 4-(Methylthio)butanenitrile plays a crucial role in the chemical composition and quality of pickled products, making it an essential component in the food industry. Its use in this application is driven by the need to achieve a specific flavor profile that is both appealing and consistent across different batches of pickles.

InChI:InChI=1/C5H9NS/c1-7-5-3-2-4-6/h2-3,5H2,1H3

Upstream product

• 74-93-1 methylthiol 
• 109-75-1 but-3-enenitrile 
• 628-20-6 4-Chlorobutyronitrile 
• 5188-07-8 sodium thiomethoxide 
• 151-50-8 potassium cyanide 
• 187722-18-5 3-(methylthio)-1-propanol mono-p-toluenesulfonate 
• 5332-06-9 4-bromobutanenitrile 

Downstream Products

• 55021-77-7 4-(methylthio)-1-butylamine 
• 84104-30-3 (+/-)-1-amino-4-(methylsulfinyl)butane 
• 4478-93-7 D,L-sulforaphane 
• 42919-64-2 4-(methylthio)butanal 
• 61121-65-1 4-(methylsulfinyl)butanenitrile 
• 1356346-85-4 1-(1-benzyl-piperidin-4-yl)-3-4-(methylsulfinyl)butyl thiourea 
• 504-84-7 erysolin 

Relevant academic research and scientific papers

BENZYL SUBSTITUTED INDAZOLES

Compounds of formula (I) and their use as pharmaceuticals.

PROCESS FOR THE SYNTHESIS OF ISOTHIOCYANATES AND DERIVATIVES THEREOF AND USES OF SAME

A method for synthesizing an isothiocyanate of general formula (I) [in-line-formulae]SCN—R1—R4—R2??(I)[/in-line-formulae] wherein R1 and R2 represent independently of each other an alkyl-aryl or aryl group, R4 represents a carbonyl, sulfinyl, sulfonyl group or a sulfide group and of its derivatives comprising a step for reacting an alkylalkylamine having the general formula (II) [in-line-formulae]NH2—R1—R4—R2??(II)[/in-line-formulae] wherein R1 and R2 represent independently of each other an alkyl, aryl or alkylaryl group, R4 represents a carbonyl, sulfinyl, sulfonyl or sulfide group, in the presence of carbon sulfide and of di-tert-butyl dicarbonate with formation of the corresponding aforesaid isothiocyanate, compounds obtained by this method as well as their uses.

Heme-coordinating inhibitors of neuronal nitric oxide synthase. Iron-thioether coordination is stabilized by hydrophobic contacts without increased inhibitor potency

The heme-thioether ligand interaction often occurs between heme iron and native methionine ligands, but thioether-based heme-coordinating (type II) inhibitors are uncommon due to the difficulty in stabilizing the Fe-S bond. Here, a thioether-based inhibitor (3) of neuronal nitric oxide synthase (nNOS) was designed, and its binding was characterized by spectrophotometry and crystallography. A crystal structure of inhibitor 3 coordinated to heme iron was obtained, representing, to our knowledge, the first crystal structure of a thioether inhibitor complexed to any heme enzyme. A series of related potential inhibitors (4-8) also were evaluated. Compounds 4-8 were all found to be type I (non-heme-coordinating) inhibitors of ferric nNOS, but 4 and 6-8 were found to switch to type II upon heme reduction to the ferrous state, reflecting the higher affinity of thioethers for ferrous heme than for ferric heme. Contrary to what has been widely thought, thioether-heme ligation was found not to increase inhibitor potency, illustrating the intrinsic weakness of the thioether-ferric heme linkage. Subtle changes in the alkyl groups attached to the thioether sulfur caused drastic changes in the binding conformation, indicating that hydrophobic contacts play a crucial role in stabilizing the thioether-heme coordination.

Analysis and anti- helicobacter activity of sulforaphane and related compounds present in Broccoli (Brassica oleracea L.) sprouts

A crude methanol extract prepared from fresh broccoli sprouts was extracted with hexane, chloroform, ethyl acetate, and butanol sequentially. Residual water fraction was obtained from the residual aqueous layer. The greatest inhibition zones (>5 cm) were noted for Helicobacter pylori strain by the chloroform extract, followed by the hexane extract (5.03 cm), the ethyl acetate extract (4.90 cm), the butanol extract (3.10 cm), and the crude methanol extract (2.80 cm), whereas the residual water fraction did not show any inhibition zone. Including sulforaphane, five sulforaphane-related compounds were positively identified in the chloroform extract, of which 5- methylsulfinylpentylnitrile was found in the greatest concentration (475.7 mg/kg of fresh sprouts), followed by sulforaphane (222.6 mg/kg) and 4-methylsulfinylbutylnitrile (63.0 mg/kg). Among 18 sulforaphane and related compounds synthesized (6 amines, 6 isothiocyanates, and 6 nitriles), 2 amines, 6 isothiocyanates, and 1 nitrile exhibited >5 cm inhibitory zones for H. pylori strain. The results indicate that broccoli sprouts can be an excellent food source for medicinal substances.

Medicine comprising a thiourea for use as depigmenting agent or anti-mutagenic and anti-carcinogenic agent

The invention concerns a medicine or a cosmetic composition comprising at least one thiourea of general formula (I), or at least one of its monooxide or dioxide derivatives of general formulae (IIa), (IIb) and (III), or mixtures thereof. This medicine is advantageously used for inhibiting tyrosinase, inhibiting melanin synthesis, for lightening or depigmenting the skin or for eliminating age spots and as antimutagenic and anti-carcinogenic agent.

Use of an isothiocyanate, a thiocyanate or a mixture thereof as depigmenting agent

The invention concerns the use if isothiocyanate of general formula (I): R1—N═C═S wherein: R1 represents an alkyl, alkenyl, alkynyl, aryl, acetyl, alkylcarbonyl, alkoxy, cycloalkyl, aryloxy, arylcarbonyl group, carboxylic acid or a —(CH2)nR3 group wherein n represents an integer ranging between 1 and 5 and R3 represents a polar functional group, advantageously a halogen atom, a sulphoxide, carbonyl, nitro, thioester, thioether, sulphonyl, sulphinyl, nitrile group, carboxylic acid, carboxylic ester, alkylthio or hydroxyl, a thiocyanate of general formula (II): R2—S═C═N wherein: R2 represents an alkyl, alkenyl, alkynyl, aryl, acctyl, alkylcarbonyl, alkoxy, cycloalkyl, aryloxy, arylcarbonyl group, carboxylic acid, carboxylic ester or a —(CH2)nR3 group, wherein n represents an integer ranging between 1 and 5 and R3 represents a polar functional group, advantageously a halogen atom, a sulphoxide, carbonyl, nitro, thioester, thioether, sulphonyl, sulphinyl, nitrile group, carboxylic acid, carboxylic ester, alkylthio or hydroxyl, or mixtures thereof for making a medicine or a cosmetic composition for inhibiting tyrosinase.

A facile and efficient synthesis of 14C-labelled sulforaphane

Isothiocyanates have gained considerable attention for their role as potent chemopreventive agents. Sulforaphane, 1a (SFN), a naturally occurring isothiocyanate, was isotopically labelled in five steps starting from 3-(methylthio)-1-propanol (2). Reacting 2 with tosyl chloride in the presence of Et3N yielded the tosylate 3. Gently refluxing 3 with K 14CN in DMF gave the nitrile 4b. Reduction to the amine 5b was achieved using BH3-THF. Oxidation with 30% hydrogen peroxide followed by treatment with thiophosgene yielded (±)[1-14C]SFN, 1b. The overall radiochemical yield was 4.4% based on the starting K 14CN. Copyright

Method and compounds for diagnosing coronary artery disease

The present invention relates generally to methods of diagnosis, evaluation and treatment of coronary artery disease in mammals using substituted catecholamines and compounds therefore. It also relates to the preparation, use and administration of these compounds which are useful in the diagnosis, evaluation and treatment of coronary artery disease by means of a feedback controlled drug delivery system that delivers exercise simulating agents which are capable of eliciting acute responses similar to those elicited by aerobic exercise.