Butyl 5-oxo-L-prolinate

Base Information

• Chemical Name: Butyl 5-oxo-L-prolinate
• CAS No.: 4931-68-4
• Molecular Formula: C9H15NO3
• Molecular Weight: 185.223
• European Community (EC) Number: 225-568-9
• DSSTox Substance ID: DTXSID60197768
• Nikkaji Number: J203.198A
• Wikidata: Q76009943
• ChEMBL ID: CHEMBL2270704
• Mol file: 4931-68-4.mol

Synonyms:4931-68-4;Butyl 5-oxo-L-prolinate;butyl (2S)-5-oxopyrrolidine-2-carboxylate;Butyl (S)-(-)-2-pyrrolidone-5-carboxylate;EINECS 225-568-9;Butyl (S)-()-2-pyrrolidone-5-carboxylate;5-Oxo-L-proline butyl ester;SCHEMBL6205684;CHEMBL2270704;DTXSID60197768;MFCD06858408;(S)-Butyl 5-oxopyrrolidine-2-carboxylate;Butyl (S)-(-)-2-pyrrolidone-5-carboxylate, 98%

Chemical Property of Butyl 5-oxo-L-prolinate

Chemical Property:

• Vapor Pressure: 0.000126mmHg at 25°C
• Refractive Index: n20/D 1.403(lit.)
• Boiling Point: 180 °C6.5 mm Hg(lit.)
• Flash Point: >230 °F
• PSA: 55.40000
• Density: 1.104 g/mL at 25 °C(lit.)
• LogP: 0.93710
• Solubility.: Chloroform
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 185.10519334
• Heavy Atom Count: 13
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

ButylPyroglutamate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Useful:

• Canonical SMILES: CCCCOC(=O)C1CCC(=O)N1
• Isomeric SMILES: CCCCOC(=O)[C@@H]1CCC(=O)N1
• Uses: Butyl Pyroglutamate is an derivative of L-Glutamic Acid (G596960), an important neurotransmitter that plays a key role in long-term potentiation and is important for learning and memory.

Technology Process of Butyl 5-oxo-L-prolinate

There total 7 articles about Butyl 5-oxo-L-prolinate 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: 89.0%

L-Pyroglutamic acid (98-79-3) + butan-1-ol (71-36-3) → (S)-butyl 5-oxopyrrolidine-2-carboxylate (4931-68-4)

Guidance literature:

With thionyl chloride; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2018.07.041

Reference yield: 59.0%

(S)-5-oxopyrrolidine-2-carbonyl chloride (74936-93-9) + butan-1-ol (71-36-3) → (S)-butyl 5-oxopyrrolidine-2-carboxylate (4931-68-4)

Guidance literature:

In dichloromethane; for 0.0833333h; Heating;

DOI:10.1080/00397919408010572

Reference yield:

methyl 5-oxopyrrolidine-2-carboxylate (4931-66-2,54571-66-3,64700-65-8) + butan-1-ol (71-36-3) → methyl (2R)-pyroglutamate (64700-65-8) + methyl (S)-pyroglutamate (4931-66-2) + (S)-butyl 5-oxopyrrolidine-2-carboxylate (4931-68-4) + butyl-5-oxopyroglutamate (84285-34-7)

Guidance literature:

With Acylase I on Eupergit C; at 25 ℃; Further Variations:; Reaction partners; Temperatures; Reagents; Product distribution;

DOI:10.1016/S0957-4166(00)00346-3

upstream raw materials:

L-glutamic acid

butan-1-ol

(S)-5-oxopyrrolidine-2-carbonyl chloride

methyl 5-oxopyrrolidine-2-carboxylate

Downstream raw materials:

pyroglutamol

(S)-1-Pyrrolidin-2-yl-methanol

Refernces

• 1、 Gang, Fang-li,Zhu, Feng,Li, Xiao-ting,Wei, Jie-lu,Wu, Wen-jun,Zhang, Ji-wen. "Synthesis and bioactivities evaluation of L-pyroglutamic acid analogues from natural product lead". . p. 4644 - 4649. Retrieved 2018/08/21.
• 2、 -. "Cosmetic composition". . . Retrieved 2008/06/13.