N-(2-MERCAPTOPROPIONYL)GLYCINE
N-(2-mercaptopropionyl)glycine
CAS: 1953-02-2
Molecular Formula: C5H9NO3S
N-(2-MERCAPTOPROPIONYL)GLYCINE - Names and Identifiers
| Name | N-(2-mercaptopropionyl)glycine |
| Synonyms | TOPRONIN Tiopronin TIOPRONIN LABOTEST-BB LT00451995 A-MERCAPTOPROPIONYL GLYCINE a-Mercaptopropionyl Glycine (2-Mercaptopropionyl)glycine N-(2-sulfanylpropanoyl)glycine N-(2-MERCAPTOPROPIONYL)GLYCINE N-(2-mercaptopropionyl)glycine ALPHA-MERCAPTO PROPIONYL GLYCINE (2-Mercaptopropionamido)acetic acid |
| CAS | 1953-02-2 |
| EINECS | 217-778-4 |
| InChI | InChI=1/C5H9NO3S/c1-3(10)5(9)6-2-4(7)8/h3,10H,2H2,1H3,(H,6,9)(H,7,8) |
N-(2-MERCAPTOPROPIONYL)GLYCINE - Physico-chemical Properties
| Molecular Formula | C5H9NO3S |
| Molar Mass | 163.19 |
| Density | 1.249 (estimate) |
| Melting Point | 93-98°C |
| Boling Point | 418.3±30.0 °C(Predicted) |
| Flash Point | 206.8°C |
| Solubility | Soluble in DMSO (32 mg/ml at 25 °C), water (32 mg/ml at 25 °C), ethanol (32 mg/ml a |
| Vapor Presure | 3.6E-08mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White |
| Merck | 14,9453 |
| BRN | 1859822 |
| pKa | 3.36±0.10(Predicted) |
| Storage Condition | Inert atmosphere,2-8°C |
| Refractive Index | 1.5216 (estimate) |
| MDL | MFCD00004861 |
| Physical and Chemical Properties | White crystalline powder, there is the smell of sulfur. Soluble in water. Melting point 95~97 °c. Acute toxicity LD50 mice (g/kg):2.1 I. V. |
| Use | Mainly used for early senile cataract, can also be used for chronic hepatitis, metal poisoning, eczema and so on |
| In vitro study | Tiopronin is an antioxidant with a free thiol (sulfhydryl) group that protects against the nephrotoxicity of Cisplatin. Tiopronin enhances the defense of cochlea and scavenges reactive oxygen radicals, while vitamin E (alpha-tocopherol) and vitamin C prevent the formation of free radicals by inhibiting lipid peroxidation. Tiopronin(2 mM) completely blocked the Cisplatin-induced increase in enzyme leakage and blocked the Cisplatin-induced decrease in MTT reduction. Tiopronin also significantly protected kidney slices from Cisplatin-induced toxic effects. Extracellularly and intracellularly, Tiopronin protects against Cisplatin-induced nephrotoxicity by acting as a Cisplatin surrogate target, thus protecting Cisplatin-induced glutathione depletion. Tiopronin protects rat kidney slices from the Nephrotoxic Effects of Cisplatin in vitro and does not reduce the antitumor activity of Cisplatin. In urea and creatinine, Tiopronin protects the increase induced by Cisplatin. In rat renal cortical slices, Tiopronin protects Cisplatin-induced adenine nucleotide changes. |
| In vivo study | In rats, Tiopronin significantly reduced serum alanine aminotransferase (ALT) and aspartate aminotransferase (AST) levels, whereas ursodeoxycholic acid (UDCA) only reduced ALT levels. Tiopronin significantly reduced the levels of triglyceride (TG), total cholesterol (TC) and free fatty acid (FFA) in serum and liver, as well as serum LDL-C levels, and increased serum HDL-C levels. |
N-(2-MERCAPTOPROPIONYL)GLYCINE - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 36/37 - Wear suitable protective clothing and gloves. |
| WGK Germany | 3 |
| RTECS | MC0596500 |
| Toxicity | LD50 i.v. in mice: 2.1 g/kg (Fujimura) |
N-(2-MERCAPTOPROPIONYL)GLYCINE - Nature
Open Data Verified Data
white crystalline powder with sulfur odor. Melting point 95~97 °c. Soluble in water.
Last Update：2024-01-02 23:10:35
N-(2-MERCAPTOPROPIONYL)GLYCINE - Preparation Method
Open Data Verified Data
propionic acid is first chlorinated with thionyl chloride and then brominated to give a-propionyl chloride. Glycine was dissolved in 2 mol/L sodium hydroxide while a-propionyl chloride and sodium hydroxide solution were added dropwise to obtain N-(Bromo-propionyl) glycine. After the interaction with sodium disulfide, and then zinc powder reduction, that is, Tiopronin. Alternatively, glycine and water are mixed, and 2-bromopropionyl chloride and sodium carbonate solution are added dropwise under certain conditions. After addition, the mixture is stirred. Thiobenzoic acid was added, and sodium hydroxide solution was added dropwise. After the reaction, a small amount of insoluble matter was filtered off, and the filtrate was acidified. The obtained solid was washed and dried, and then concentrated aqueous ammonia was added to an aqueous sodium carbonate solution, stirred, washed, filtered, acidified with hydrochloric acid, concentrated under reduced pressure, and dissolved by adding a hot mixture of ethyl acetate and ethanol. Tiopronin was then treated. It is also possible to reflux 2-chloropropionic acid and thionyl chloride together to give 2-chloropropionyl chloride. Glycine, sodium carbonate and an appropriate amount of water were mixed, and an aqueous solution of 2-chloropropionyl chloride and sodium carbonate was added dropwise under cooling in an ice-salt bath and vigorous stirring, followed by stirring. Acidification with hydrochloric acid, extraction with ethyl acetate, the material obtained by the treatment is dissolved in sodium carbonate aqueous solution, and the reaction is added dropwise to sodium disulfide solution, and zinc powder is added to the filtrate through acidification with sulfuric acid, filtration, tiopronin was also obtained after treatment.
Last Update：2022-01-01 09:23:38
N-(2-MERCAPTOPROPIONYL)GLYCINE - Use
Open Data Verified Data
Tiopronin is a novel glycine Derivative Containing a free thiol group. It can activate metabolic enzymes and chelate with toxic substances that hinder HS-enzyme activity, thus having detoxification effect. For viral hepatitis, alcoholic hepatitis, drug-induced hepatitis, heavy metal toxic hepatitis, fatty liver and liver cirrhosis early treatment. It can reduce the side effects of radiotherapy and chemotherapy, increase white blood cells and accelerate the recovery of liver cells, reduce the rate of bone marrow chromosome aberration and skin ulcer, and prevent the occurrence of secondary tumors caused by radiotherapy. It has significant therapeutic effect on senile early cataract and vitreous opacity. It has anti-inflammatory and anti-allergic effects, and has good effects on dermatitis, eczema, acne and urticaria. Can also prevent and treat urinary cystine stones.
Last Update：2022-01-01 09:23:38
N-(2-MERCAPTOPROPIONYL)GLYCINE - Safety
Open Data Verified Data
mice were injected intravenously with LD50: 2.1g/kg.
Last Update：2022-01-01 09:23:39
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Product Name: N-(2-mercaptopropionyl)glycine Request for quotationCAS: 1953-02-2
Tel: +86-17551318830
Email: r@reformchem.com
Mobile: +86-17551318830
QQ: 3785839865
Product Name: N-(2-mercaptopropionyl)glycine Request for quotation
CAS: 1953-02-2
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
CAS: 1953-02-2
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
Wechat: 17505222756
Multiple SpecificationsSpot supply
Product Name: N-(2-Mercaptopropionyl)glycine Visit Supplier Webpage Request for quotationCAS: 1953-02-2
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
Product Name: Tiopronin Request for quotation
CAS: 1953-02-2
Tel: +86-21-56795779
Email: charles7788@worldyachem.com
Mobile: +86-13651600618
QQ: 2850607228
Wechat: 13651600618
WhatsApp: +8613651600618
CAS: 1953-02-2
Tel: +86-21-56795779
Email: charles7788@worldyachem.com
Mobile: +86-13651600618
QQ: 2850607228
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