1195-16-0

Basic information

• Product Name: N-(Tetrahydro-2-oxo-3-thienyl)-acetamide
• Synonyms: 2-acetamido-4-mercaptobutyricacidthiolactone;achtl;ahctl;alpha-acetamido-gamma-thiobutyrolactone;bo714;citiolase;n-(tetrahydro-2-oxo-3-thienyl)-acetamid;n-acetylhomocysteinethiolactone
• CAS NO: 1195-16-0
• Molecular Formula: C₆H₉NO₂S
• Molecular Weight: 159.21
• EINECS: 214-793-8
• Product Categories: Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes;CITIOLASE
• Mol File: 1195-16-0.mol

Chemical Properties

• Melting Point: 109-111 °C
• Boiling Point: 427.265 °C at 760 mmHg
• Flash Point: 212.202 °C
• Appearance: /solid
• Density: 1.202 (estimate)
• Vapor Pressure: 1.66E-07mmHg at 25°C
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 14.62±0.20(Predicted)
• Merck: 14,2320
• CAS DataBase Reference: N-(Tetrahydro-2-oxo-3-thienyl)-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Tetrahydro-2-oxo-3-thienyl)-acetamide(1195-16-0)
• EPA Substance Registry System: N-(Tetrahydro-2-oxo-3-thienyl)-acetamide(1195-16-0)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 22-24/25-45-36-26
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: AC8680000
• TSCA: Yes
• Hazardous Substances Data: 1195-16-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-(Tetrahydro-2-oxo-3-thienyl)-acetamide is used as a hepatoprotectant, which helps protect and support liver function. It is also utilized as a free radical scavenger, playing a crucial role in neutralizing harmful free radicals and preventing oxidative stress-related damage.
Used in Photographic Industry:
N-(Tetrahydro-2-oxo-3-thienyl)-acetamide serves as a photographic antifogging agent, as documented in patents by Dersch (US 3068100, 1962) and Weber (DE 1164828, 1964 to Adox Fotowerke Schleussner GmbH). Its application helps improve the quality and clarity of photographic images by preventing fogging.
Used in Radiation Protection:
N-(Tetrahydro-2-oxo-3-thienyl)-acetamide acts as a protector against radiation, as demonstrated in studies by Langendorff and Koch (Strahlentherapie 106, 451, 1958) and Braun et al. (ibid 108, 262, 1959). This property makes it valuable in various applications where radiation protection is necessary, such as in medical and industrial settings.

Originator

Citiolase,Roussel Maestretti France,1970

Manufacturing Process

12.73 kg of acetyl methionine are gradually introduced into a brine-cooledpressure-tight apparatus provided with a stirrer and containing 140 liters of liquid ammonia at -50°C. The amino acid is dissolved after a short time; 6.5 kg of sodium metal are then introduced over a period of from 4 to 5 hours at a temperature of from -40°C to 60°C. Eventually, a persistent blue coloration of the ammoniacal solution indicates the end of the reaction. The ammonia is distilled off and the residue is taken up in 70 liters of methanol. In order to remove ammonia which has been formed from sodium amide, 30 to 40 liters of methanol are distilled off and the residue is made up with methanol to 80 liters. The strongly alkaline solution is neutralized with 22 liters of concentrated aqueous hydrochloric acid. The solution is filtered off from the precipitated sodium chloride and evaporated to dryness in vacuo. The closing of the thiolactone ring takes place as a result of the evaporation of the solution to dryness in the acid pH range and the N-acetyl homocystein originally present is converted into N-acetyl homocystein thiolactone. In order to isolate N-(Tetrahydro-2-oxo-3-thienyl)-acetamide, the residue is recrystallized from 25% aqueous alcohol. 9 kg of N-acetyl homocystein thiolactone are obtained, this corresponding to a yield of 85% of the theoretical.

Therapeutic Function

Hepatoprotectant

Purification Methods

Dry Citiolone in a vacuum desiccator. It recrystallises from toluene as needles. It is a ninhydrin -ve substance which gives a “slow” nitroprusside test. It has max at 238nm ( 4,400 M-1cm-1); and (nujol) 1789s and 851ms cm. [Benesch & Benesch J Am Chem Soc 78 1597max 1956, cf Laliberté J Chem Soc 2756 1963.]

InChI:InChI=1/C6H9NO2S/c1-4(8)7-5-2-3-10-6(5)9/h5H,2-3H2,1H3,(H,7,8)/t5-/m0/s1

Upstream product

• 2185-03-7 L-homoserine lactone hydrochloride 
• 10387-40-3 potassium thioacetate 
• 2185-02-6 L-homoserine lactone 
• 7540-67-2 O-acetyl-L-homoserine 
• 51524-71-1 2,2-dichloro-N-[(3S)-tetrahydro-2-oxo-3-furanyl]-acetamide 
• 6038-19-3 3-aminodihydrothiophen-2(3H)-one hydrochloride 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 563-63-3 silver(I) acetate 

Downstream Products

• 85838-36-4 1-(N-acetyl-DL-homocysteinylamino)-6-(benzyloxycarbonylamino)hexane 
• 152420-81-0 5-Chloro-3-formyl-thieno<2,3-b>pyridine 
• 6038-19-3 3-aminodihydrothiophen-2(3H)-one hydrochloride 
• 57271-88-2 N-acetyl-rac-ethionine 
• 1261160-55-7 C₁₃H₁₈N₂O₂S 
• 85838-45-5 C₅₇H₈₅N₉O₁₈S 
• 85838-46-6 C₄₉H₇₁N₇O₁₆S 
• 85838-43-3 N--2-oxoethyl)-DL-homocysteinyl>-N-(5-ethoxycarbonylpentyl)glycinamide 
• 85838-44-4 N--2-oxoethyl)-DL-homocysteinyl>-N-(5-carbonylpentyl)glycinamide 
• 85838-41-1 ethyl N--2-oxoethyl)-DL-homocysteinyl>glycinate 
• 85838-42-2 N--2-oxoethyl)-DL-homocysteinyl>glycine 
• 85838-39-7 ethyl N-(N-acetyl-S-<6-(benzyloxycarbonylamino)hexyl>-DL-homocysteinyl)glycinate 
• 85838-40-0 N-(N-acetyl-S-<6-(benzyloxycarbonylamino)hexyl>-DL-homocysteinyl)glycine 
• 258266-92-1 R,S-5-acetylamino-3-(4-methoxyphenyl)-2-thioxo-1,3-thiazepan-4-one 

Relevant articles and documents

Synthesis of sequence-ordered polymers via sequential addition of monomers in one pot

Sequence-ordered polymers can be simply prepared in one pot via sequential monomer addition.

Syntheses of Sequence-Controlled Polymers via Consecutive Multicomponent Reactions

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Preparation Method for Homocystein Thiolactone or Selenolactone

The present invention provides an expensive reagent such as homocysteine thiolactone or selenolactone as the main intermediate of erdosteine, or an expensive reagent such as HI. More specifically, A) a homoserine lactone or N - protected homoserine is reacted with a thiocarboxylic acid metal salt or selenocarboxylic acid metal salt (RCOXM, X=S or Se). B) Step A) of producing homocysteine thiolactone or homocysteine sonoactone by deprotection of N - protected homocysteine thiolactone or N - protected homocysteine seleactone. The present invention relates to a method for producing homocysteine thiactone or homocysteine senolactone or a salt thereof by the following reaction scheme. [Reaction Scheme] Then, this time. X Is S or Se, R and R ' are independently alkyl or aryl which is C1 - C6, and M is Na or K.

MANUFACTURING METHOD OF N-ACYL-α-AMINOLACTONE COMPOUND

PROBLEM TO BE SOLVED: To provide a method for manufacturing an N-acyl-α-aminolactone compound in a high yield and a high purity from an acid salt of α-aminolactone. SOLUTION: The provided method for manufacturing an N-acyl-α-aminolactone compound is a method for manufacturing a specified N-acyl-α-aminolactone compound by reacting, in the presence of a solvent and a basic compound, an acid salt of a specified α-aminolactone and an anhydrous fatty acid. The reaction is carried out in the presence of a weak-basic compound at a quantitative ratio of 0.7 or more molar equivalent and 5 or less molar equivalent with respect to 1 mole of the acid salt of the α-aminolactone. The number of carbon atoms of the anhydrous fatty acid is 4 or more and 12 or less. The solvent is a solvent having solubilities, with the α-aminolactone and weak-basic compound (25°C), of 1 g or less each and a solubility, with the anhydrous fatty acid (25°C), of 10 g or more and is at least one type selected from among ketone-based solvents, ether-based solvents, ester-based solvents, and halogen-based solvents. COPYRIGHT: (C)2015,JPOandINPIT

Two tandem multicomponent reactions for the synthesis of sequence-defined polymers

Multicomponent polymerizations have become powerful tools for the construction of sequence-defined polymers. Although the Passerini multicomponent reaction has been widely used in the synthesis of sequence-defined polymers, the tandem usage of the Passerini multicomponent reaction and other multicomponent reactions in one-pot for the synthesis of sequence-defined polymers has not been developed until now. In this contribution, we report the tandem usage of the Passerini three-component reaction and the three-component amine-thiol-ene conjugation reaction in one pot for the synthesis of sequence-defined polymers. The Passerini reaction between methacrylic acid, adipaldehyde, and 2-isocyanobutanoate was carried out, affording a new molecule containing two alkene units. Subsequently, an amine and a thiolactone were added to the reaction system, whereupon the three-component amine-thiol-ene conjugating reaction occurred to yield a sequence-defined polymer. This method offers more rapid access to sequence-defined polymers with high molecular diversity and complexity.