60460-30-2

Basic information

• Product Name: L-Proline, 1-(1-oxo-2-propenyl)- (9CI)
• Synonyms: L-Proline, 1-(1-oxo-2-propenyl)- (9CI)
• CAS NO: 60460-30-2
• Molecular Formula: C₈H₁₁NO₃
• Molecular Weight: 169.17784
• Product Categories: PYRROLE
• Mol File: 60460-30-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 403.2°C at 760 mmHg
• Flash Point: 197.7°C
• Appearance: /
• Density: 1.254g/cm³
• Vapor Pressure: 1.25E-07mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: L-Proline, 1-(1-oxo-2-propenyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-(1-oxo-2-propenyl)- (9CI)(60460-30-2)
• EPA Substance Registry System: L-Proline, 1-(1-oxo-2-propenyl)- (9CI)(60460-30-2)

Safety Data

• Hazardous Substances Data: 60460-30-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H11NO3/c1-2-7(10)9-5-3-4-6(9)8(11)12/h2,6H,1,3-5H2,(H,11,12)

Upstream product

• 814-68-6 acryloyl chloride 
• 147-85-3 L-proline 
• 625-36-5 2-chloropropionyl chloride 

Downstream Products

• 613256-52-3 β-hydroxy-α-methyl-N-acryloyl-(S)-proline 
• 62571-86-2 captopril 

Relevant articles and documents

A synthesis of captopril through a Baylis-Hillman reaction

A synthesis of the antihipertensive amide 1, named captopril, is described. The strategy is based on a Baylis-Hillman reaction between N-acryloylproline and formaldehyde. Subsequential diaster eoselective hydrogenation step and functional group interconversion provided captopril in good overall yield.

A DRUG AND SYNTHESIS OF THE DRUG TO TREAT HIGH BLOOD PRESSURE AND TYPE 2 DIABETES MELLITUS DISEASE

The invention relates to a drug and its method of manufacture, which allows to reduce hypertension and treat type 2 diabetes mellitus by using the drug as a dipeptidyl peptidase-4 (DPP-4) inhibitor. The rate of hypoglycemia of the drug in question is low and provides glycemic control and weight loss. The method of manufacturing the mentioned drug includes practical steps to convert the carboxyl group from captopril (1) to the nitrile group.

Poly(n-acryl amino acids): A new class of biologically active polyanions

Poly(N-acryl amino acids) bearing side groups with a lipophilic character or having charged functional groups (i.e. -NH2, -COOH, -SH, -OH, and phenols) were synthesized from the radical polymerization of N-acryl amino acid monomers. Monomers were prepared from the reaction of acryloyl chloride and amino acid esters in dry solvents. Polymers of a broad molecular weight ranging from 3 000 to 60 000 Da were obtained. The polymers were optically active, and their structures were confirmed by 1H NMR and IR spectra and elemental analysis. Hydroxyl-containing polymers were sulfated in high conversion yields by SO3/pyridine complex. The newly synthesized linear homopolyanions were tested for heparin-like activities: (i) inhibition of heparanase enzyme, (ii) release of basic fibroblast growth factor (bFGF) from the extracellular matrix (ECM), and (iii) inhibition of smooth muscle cell (SMC) proliferation. Polymers based on tyrosine and leucine were highly active in all three tests (microgram level). Polymers based on phenylalanine, tert-leucine, and proline were active as heparanase inhibitors and FGF release, and polymers of trans-hydroxyproline, glycine, and serine were active only as heparanase inhibitors. The polymer of cis-hydroxyproline was inactive. It was found that a net anionic charge (i.e. carboxylic acid) is essential for biological activity. Thus, methyl ester derivatives of the active polymers, zwitterionic amino acid pendent groups (lysine, histidine), and decarboxylated amino acids (tyramine, ethanolamine) were inactive. The above active polymers did not exhibit anticoagulation activity which is considered the main limitation of heparin and heparinomimetics for clinical use. These synthetic poly(N-acryl amino acids) may have potential use in the inhibition of heparanase-mediated degradation of basement membranes associated with tumor metastasis, inflammation, and autoimmunity.