DL-Propargylglycine

Base Information

• Chemical Name: DL-Propargylglycine
• CAS No.: 64165-64-6
• Molecular Formula: C₅H₇NO₂
• Molecular Weight: 113.116
• Mol file: 64165-64-6.mol

Synonyms:Propargyl glycine

Chemical Property of DL-Propargylglycine

Chemical Property:

• Boiling Point: 273.5 °C at 760 mmHg
• Flash Point: 119.2 °C
• PSA: 63.32000
• Density: 1.15 g/cm³
• LogP: 0.12190
• Storage Temp.: −20°C
• Solubility.: Soluble in DMSO (up to 10 mg/ml) or in Water (up tp 10 mg/ml).

Purity/Quality:

98%,99%, ^*data from raw suppliers

DL-Propargylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Propargylglycine (64165-64-6) is an irreversible inhibitor of the hydrogen sulfide biosynthesis enzyme, cystathione-γ-lyase. It inhibits H2S production in rat liver preparations (IC50=55 μM) and inhibits the rise in plasma H2S in rats with hemorrhagic shock2. Propargylglycine reduces inflammation in a rodent carrageenan-induced hindpaw edema model3 and ameliorates gentamycin-induced nephrotoxicity1.

Technology Process of DL-Propargylglycine

There total 13 articles about DL-Propargylglycine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(R)-2-(2,2,5,7,8-Pentamethyl-chroman-6-sulfonylamino)-5-trimethylsilanyl-pent-4-ynoic acid (207459-88-9) → (R)-2-aminopent-4-ynoic acid (23235-01-0,23235-03-2,50428-03-0,64165-64-6)

Guidance literature:

With trifluoroacetic acid; Heating;

DOI:10.1039/c39940000943

Reference yield: 88.8%

N-Acetyl-α-propargylglycine (23235-02-1,23235-04-3,23234-80-2) → (2S)-2-amino-4-pentynoic acid (23235-01-0) + (R)-2-aminopent-4-ynoic acid (23235-01-0,23235-03-2,50428-03-0,64165-64-6)

Guidance literature:

at 37 ℃; for 21h;

DOI:10.1021/jm00366a015

Reference yield: 84.0%

(R)-2-amino-4-pentynoic acid methyl ester (78342-50-4) → (R)-2-aminopent-4-ynoic acid (23235-01-0,23235-03-2,50428-03-0,64165-64-6)

Guidance literature:

With hydrogenchloride; methyloxirane; 1.) 1 h, reflux, 2.) EtOH, 15 min, reflux;

upstream raw materials:

N-Acetyl-D-α-propargylglycine

N-Acetyl-α-propargylglycine

(R)-2-amino-4-pentynoic acid methyl ester

(2R,5S)-5-isopropyl-3,6-dimethoxy-2-propargyl-2,5-dihydropyrazine

Downstream raw materials:

Boc-L-Pra-OH

(R)-2-amino-4-pentynoic acid methyl ester

(R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pent-4-ynoic acid

(R)-2-(toluene-4-sulfonylamino)pent-4-ynoic acid

Refernces

• 1、 Brea, Roberto J.,Lopez-Deber, M. Pilar,Castedo, Luis,Granja, Juan R.. "Synthesis of ω-(hetero)arylalkynylated α-amino acid by sonogashira-type reactions in aqueous media". . p. 7870 - 7873. Retrieved 2007/10/03.
• 2、 Collet, Sylvain,Bauchat, Patrick,Danion-Bougot, Renee,Danion, Daniel. "Stereoselective, nonracemic synthesis of ω-borono-α-amino acids". . p. 2121 - 2131. Retrieved 2007/10/03.