444-27-9

Basic information

• Product Name: Thiazolidine-4-carboxylic acid
• Synonyms: 4-carboxythiazolidine;4-thiazolidinecarboxylicacid;acidethiazolidine-4-carboxylique;gamma-thiaproline;hepalidine;heparegene;norgamem;nsc25855
• CAS NO: 444-27-9
• Molecular Formula: C₄H₇NO₂S
• Molecular Weight: 133.17
• EINECS: 207-146-6
• Product Categories: Heterocyclic Compounds;DETOXEPA;API
• Mol File: 444-27-9.mol

Chemical Properties

• Melting Point: 196.5°C
• Boiling Point: 350.302 °C at 760 mmHg
• Flash Point: 165.657 °C
• Appearance: /solid
• Density: 1.226 (estimate)
• Refractive Index: 1.5480 (estimate)
• Storage Temp.: Room Temperature
• PKA: 2.09±0.20(Predicted)
• Water Solubility: 29.3g/L(21 oC)
• CAS DataBase Reference: Thiazolidine-4-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Thiazolidine-4-carboxylic acid(444-27-9)
• EPA Substance Registry System: Thiazolidine-4-carboxylic acid(444-27-9)

Safety Data

• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 444-27-9(Hazardous Substances Data)

Usage

Uses

1. Used in Pharmaceutical Industry:
Thiazolidine-4-carboxylic acid is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
2. Used in Antineoplastic Research:
Thiazolidine-4-carboxylic acid is used as a research molecule with potential antineoplastic activities. It acts on the cell membrane of tumor cells, causing reverse transformation to normal cells, which can be beneficial in the development of novel cancer treatments.
3. Used in Drug Delivery Systems:
Thiazolidine-4-carboxylic acid can be employed in the development of drug delivery systems, where its unique structure may enhance the delivery, bioavailability, and therapeutic outcomes of various pharmaceutical compounds.
4. Used in Chemical Synthesis:
Thiazolidine-4-carboxylic acid serves as an important intermediate in the synthesis of various organic compounds, including those with potential applications in the chemical, pharmaceutical, and materials science industries.

Originator

Hepaldine,Riker,France,1964

Manufacturing Process

Cysteine is first dissolved in distilled water which has been freed of oxygen by boiling. Formaldehyde of 30% (w/v) concentration is added while stirring and the temperature of the mixture rises, while the thiazolidine carboxylic acid begins crystallizing. The stirring is continued for 2 hours after which ethyl alcohol of 95% (w/v) concentration is added to induce further crystallization. The mixture is left to stand for 24 hours at 4°C. The mixture is then filtered with retention of a crude product, which is purified by recrystallization from boiling distilled water. The crystals are then dried at about 40°C. The free acid is then converted to the sodium salt with NaOH.

Therapeutic Function

Hepatoprotectant, Choleretic

InChI:InChI=1/C4H7NO2S/c6-4(7)3-1-8-2-5-3/h3,5H,1-2H2,(H,6,7)

Upstream product

• 34592-47-7 L-thioproline 
• 50-00-0 formaldehyd 
• 921-01-7 rac-cysteine 
• 444-27-9 (RS)-4-thiazolidinecarboxylic acid 
• 114192-98-2 (2R,3R)-2,3-Dihydroxy-succinic acid; compound with (S)-thiazolidine-4-carboxylic acid 
• 52-89-1 l-cysteine hydrochloride 
• 52-89-1 L-cysteine hydrochloride 
• 32443-99-5 D-cysteine hydrochloride 
• 10318-18-0 DL-cysteine hydrochloride 

Downstream Products

• 119616-17-0 3-benzoyl-thiazolidine-4-carboxylic acid 
• 122230-48-2 3-phenylacetyl-thiazolidine-4-carboxylic acid 
• 119910-75-7 1,2,3,3aα,4α,8,8aβ,8bα-octahydro-2-methyl-4-phenylpyrrolo<3',4':3,4>pyrrolo<1,2-c>thiazole-1,3-dione 
• 119910-75-7 1,2,3,3aα,4β,8aα,8bα-octahydro-2-methyl-4-phenylpyrrolo<3',4':3,4>pyrrolo<1,2-c>thiazole-1,3-dione 
• 137441-54-4 C₃₁H₃₈N₂O₃S 
• 110822-04-3 N-(5-methyl-2-nitrobenzoyl)thiazolidine-4-carboxylic acid 
• 88381-44-6 N-nitrosothiazolidine-4-carboxylic acid 
• 640-61-9 N-methyl-p-toluenesulfonylamide 
• 5025-82-1 N-acetyl-thiazolidine-4-carboxylic acid 
• 131570-70-2 (4aS,7aS,8R,8aR)-8-Phenyl-hexahydro-cyclopenta[4,5]pyrrolo[1,2-c]thiazol-7-one 
• 131570-71-3 (1S,6R,7R,11R)-11-Phenyl-4-thia-2-aza-tricyclo[5.3.1.0^2,6]undecan-8-one 
• 110822-07-6 N-(5-methyl-2-nitrobenzyl)thiazolidine-4-carboxylic acid 
• 51977-23-2 6-phenyl-1H,3H-imidazo<1,5-c>thiazole-5,7-<6H,7aH>-dione 
• 86634-64-2 Tetrahydro-6-phenyl-5-thioxoimidazo[1,5-c]thiazol-7(3H)-one 

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