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

General Description

Benzyl L-prolinate is a chemical compound composed of the amino acid L-proline and benzyl group. It is used in organic synthesis as a chiral building block for the production of pharmaceuticals and agrochemicals. benzyl L-prolinate has been found to exhibit antioxidant and anticancer properties, making it a promising candidate for the development of new therapeutic agents. Additionally, benzyl L-prolinate has been utilized in the preparation of peptides and peptide-based polymers, highlighting its versatility in various fields of chemistry. Overall, benzyl L-prolinate is a valuable chemical compound with potential applications in drug discovery and material science.

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 
• 30924-93-7 Boc-Glu-OBn 
• 78658-49-8 Boc-Glu(OSu)-OBn 
• 91229-97-9 (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 256390-71-3 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester 
• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 146627-68-1 C₁₉H₂₁NO₄S 

Downstream Products

• 82134-73-4 1-[3-(4-Cyanomethyl-phenoxy)-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester 
• 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 

Relevant articles and documents

A class of novel conjugates of substituted purine and Gly-AA-OBzl: Synthesis and evaluation of orally analgesic activity

Aimed at the chemotherapy of chronic pain two kinds of analgesic pharmacophores, substituted purine and Gly-AA-OBzl, were coupled via a five-step-reaction procedure and 19 novel conjugates N-[2-chloro-9- (tetrahydropyran-2-yl)-9H-purin-6-yl]-N-cyclopropylglycylamino acid benzylesters were provided. On mouse-tail flick model their in vivo analgesic activities were assayed. The results indicate that introducing Gly-OC2H 5 into the 6-position of the substituted purine leads to ambiguous increase of the analgesic activity, while introducing Gly-AA-OBzl into this position leads to significant increase of the analgesic activity.

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.