41324-66-7

Basic information

• Product Name: benzyl L-prolinate
• Synonyms: benzyl L-prolinate;proline benzyl ester;L-Proline benzyl;L-Proline phenylmethyl ester;16652-71-4 (Hydrochloride);Einecs 255-314-2;Nsc 206250
• CAS NO: 41324-66-7
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.253
• EINECS: 255-314-2
• Mol File: 41324-66-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 309°Cat760mmHg
• Flash Point: 140.7°C
• Appearance: /
• Density: 1.121g/cm³
• CAS DataBase Reference: benzyl L-prolinate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl L-prolinate(41324-66-7)
• EPA Substance Registry System: benzyl L-prolinate(41324-66-7)

Safety Data

• Hazardous Substances Data: 41324-66-7(Hazardous Substances Data)

Usage

Description

Benzyl L-prolinate is a chemical compound consisting of the amino acid L-proline and a benzyl group. It is recognized for its antioxidant and anticancer properties, positioning it as a promising candidate for the development of new therapeutic agents. Its role as a chiral building block in organic synthesis further underscores its value in the production of pharmaceuticals and agrochemicals. Benzyl L-prolinate's versatility extends to the preparation of peptides and peptide-based polymers, making it a significant compound in various chemistry fields.

Uses

Used in Pharmaceutical Industry:
Benzyl L-prolinate serves as a chiral building block for the synthesis of pharmaceuticals, contributing to the development of new drugs with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical sector, benzyl L-prolinate is utilized as a chiral building block for the production of agrochemicals, enhancing the effectiveness and selectivity of these compounds in agricultural applications.
Used in Anticancer Applications:
Benzyl L-prolinate is employed as an anticancer agent, leveraging its inherent properties to combat cancer cells and contribute to the development of novel therapeutic strategies.
Used in Antioxidant Formulations:
Capitalizing on its antioxidant properties, benzyl L-prolinate is used in the formulation of antioxidants, which can protect cells from oxidative damage and have potential applications in health and wellness products.
Used in Peptide and Polymer Synthesis:
Benzyl L-prolinate is utilized in the preparation of peptides and peptide-based polymers, showcasing its versatility and importance in the synthesis of complex biologically active molecules and materials.

InChI:InChI=1/C12H15NO2/c14-12(11-7-4-8-13-11)15-9-10-5-2-1-3-6-10/h1-3,5-6,11,13H,4,7-9H2

Upstream product

• 37787-77-2 Boc-L-proline benzyl ester 
• 172946-54-2 N-Pent-4-enoyl-L-proline benzyl ester 
• 256390-67-7 (S)-2-Amino-5-methanesulfonyloxy-pentanoic acid benzyl ester 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 147-85-3 L-proline 
• 100-51-6 benzyl alcohol 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 146627-68-1 C₁₉H₂₁NO₄S 
• 256390-71-3 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester 
• 91229-97-9 (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester 
• 78658-49-8 Boc-Glu(OSu)-OBn 
• 30924-93-7 Boc-Glu-OBn 

Downstream Products

• 124778-25-2 N-<(2R)-2-Hydroxy-2-phenylacetyl>-(S)-prolin-benzylester 
• 124778-27-4 N-<(2S)-2-Hydroxy-2-phenylacetyl>-(S)-prolin-benzylester 
• 94726-50-8 N-(2-Oxo-2-phenylacetyl)prolin-benzylester 
• 29776-78-1 (S)-1-(2-tert-butoxycarbonylaminoacetyl)pyrrolidine-2-carboxylic acid benzyl ester 
• 95015-61-5 Z-Arg(NO₂)-Pro-Lys(Z)-Pro-OBzl 
• 96847-85-7 (S)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-isobutyl ester 
• 29776-70-3 N-(tert-butyloxycarbonyl)-prolyl-proline benzyl ester 
• 58872-03-0 1--L-valyl>-L-proline phenylmethyl ester 
• 74257-99-1 (S)-benzyl 1-((2S,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoyl)pyrrolidine-2-carboxylate 
• 83610-44-0 benzyl (2S)-1-[(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methylpentanoyl]pyrrolidine-2-carboxylate 
• 111496-28-7 (S)-1-((S)-2-Hydroxy-4-methyl-pentanoyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 111496-27-6 (S)-1-((S)-2-Hydroxy-hexanoyl)-pyrrolidine-2-carboxylic acid benzyl ester 
• 74763-79-4 PChd-L-Pro-OBzl 
• 35930-84-8 Boc-Asn-Pro-OBzl 

Relevant articles and documents

Efficient asymmetric organocatalytic formation of erythrose and threose under aqueous conditions

Esters of proteinogenic amino acids efficiently catalyse the formation of erythrose and threose under aqueous conditions in the highest yields and enantioselectivities yet reported. Remarkably while esters of (l)-proline yield (l)-carbohydrates, esters of (l)-leucine and (l)-alanine generate (d)-carbohydrates, offering the potential to account for the prebiotic link between natural (l)-amino acids and natural (d)-sugars.

Synthesis and cytotoxic activities of β-carboline amino acid ester conjugates

β-Carboline represents a class of compounds with potent anti-tumor activity by intercalating with DNA. To further enhance the cytotoxic potency and bioavailability of β-carboline, a series of novel β-carboline amino acid ester conjugates were designed and synthesized, and the cytotoxic activities of these compounds were tested using a panel of human tumor cell lines. In addition, the membrane permeability of these compounds was evaluated in vitro using a Caco-2 cell monolayer model. The β-carboline amino acid ester conjugates demonstrated improved cytotoxic activity compared to the parental β-carbolines. In particular, the Lys/Arg conjugates were the most potent analogs with an IC50 value of 4 and 1 μM against human cervical carcinoma cells. The low interaction energy of Arg conjugate based on molecular modeling may contribute to its enhanced cytotoxicity. Taken together, this study provided new insights into structure-activity relationships in the β-carboline amino acid ester conjugates and identified the β-carboline Lys/Arg conjugates as promising lead compounds for further in vivo biological and molecular evaluation.

Solution-phase automated synthesis of tripeptide derivatives

An improved general method for automated synthesis of tripeptides was developed, in which methanesulfonic acid (MSA) was used in place of trifluoroacetic acid (TFA), thus making it possible to avoid, 1) corrosion of the apparatus by strong acid vapor, 2) formation of emulsions, and 3) use of the restricted solvent, dichloromethane. As an application of the automated synthesis apparatus, 216 fragment tripeptide derivatives were synthesized systematically using the MSA method, in excellent yield and with increased efficiency.