Phenylpropionylglycine

Base Information

• Chemical Name: Phenylpropionylglycine
• CAS No.: 56613-60-6
• Molecular Formula: C11H13NO3
• Molecular Weight: 207.229
• Hs Code.: 2922509090
• European Community (EC) Number: 809-237-1
• DSSTox Substance ID: DTXSID20864969
• Nikkaji Number: J486.585E
• Wikidata: Q27160441
• Metabolomics Workbench ID: 37470
• ChEMBL ID: CHEMBL322376
• Mol file: 56613-60-6.mol

Synonyms:Phenylpropionylglycine;N-(3-Phenylpropionyl)glycine;N-(3-phenylpropanoyl)glycine;2-(3-phenylpropanoylamino)acetic Acid;(3-Phenylpropionyl)glycine;Glycine, N-(1-oxo-3-phenylpropyl)-;CHEBI:88550;2-(3-phenylpropanamido)acetic acid;(3-Phenyl-propionylamino)-acetic acid;3-Phenylpropanoyl glycine;(3-phenylpropanoyl)glycine;HYDROCINNAMOYLGLYCINE;Oprea1_505431;CHEMBL322376;SCHEMBL3995983;N-(3-phenyl-propionyl)-glycine;DTXSID20864969;(3-phenyl-propionylamino)-acetate;HY-N7403;MFCD00749241;STK083197;AKOS000142015;CS-0119437;EN300-303856;Q27160441;Z85886717;N-(3-Phenylpropionyl)glycine, analytical reference material

Chemical Property of Phenylpropionylglycine

Chemical Property:

• Vapor Pressure: 3.44E-06mmHg at 25°C
• Melting Point: 118℃
• Refractive Index: 1.549
• Boiling Point: 480 °C at 760 mmHg
• PKA: 3.59±0.10(Predicted)
• Flash Point: 244.1 °C
• PSA: 69.89000
• Density: 1.202g/cm³
• LogP: 1.66030
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 207.08954328
• Heavy Atom Count: 15
• Complexity: 222

Purity/Quality:

98%Min ^*data from raw suppliers

N-(3-Phenylpropionyl)glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CCC(=O)NCC(=O)O
• Uses: N-(3-Phenylpropionyl)glycine detection is a useful diagnostic tool in the diagnosis of many organic acidemias and mitochondrial fatty acid β-oxidation defects. N-(3-Phenylpropionyl)glycine is present in the urine of medium-chain acyl-CoA dehydrogenase deficient (MCAD) patients who orally ingested 3-phenylpropionic acid.

Technology Process of Phenylpropionylglycine

There total 8 articles about Phenylpropionylglycine 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: 91.0%

glycine (56-40-6,18875-39-3,25718-94-9) + hydrocinnamic acid chloride (645-45-4) → [(3-phenylpropionyl)amino]acetic acid (56613-60-6)

Guidance literature:

With sodium hydroxide; In water; acetonitrile; at 0 - 20 ℃; for 3h;

DOI:10.1039/c6cc02865a

Reference yield: 85.0%

→ [(3-phenylpropionyl)amino]acetic acid (56613-60-6)

Guidance literature:

Reference yield:

4-phenylazetidin-2-one (5661-55-2) → [(3-phenylpropionyl)amino]acetic acid (56613-60-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / KOH; Bu₄NBr / tetrahydrofuran

2: 17 percent Turnov_. / H₂

With potassium hydroxide; tetrabutylammomium bromide; hydrogen; In tetrahydrofuran;

DOI:10.1002/1521-4184(20008)333:8<243::AID-ARDP243>3.0.CO;2-O

upstream raw materials:

N-cinnamoylglycine

glycine

hydrocinnamic acid chloride

benzyl (RS)-2-(2-oxo-4-phenylazetidin-1-yl)acetate

Downstream raw materials:

N-(3-phenylpropanoyl)glycine methyl ester

C₁₁H₁₂ClNO₂

N-[(benzhydrylmethylcarbamoyl)methyl]-3-phenylpropionamide

Refernces

• 1、 Guan, Mingyu,Pang, Yubo,Zhang, Jingyu,Zhao, Yingsheng. "Pd-Catalyzed sequential β-C(sp3)-H arylation and intramolecular amination of δ-C(sp2)-H bonds for synthesis of quinolinones: Via an N,O-bidentate directing group". supporting information. p. 7043 - 7046. Retrieved 2016/06/09.
• 2、 Achilles, Karin,Schirmeister, Tanja,Otto, Hans-Hartwig. "β-Lactam derivatives as enzyme inhibitors: 1-Peptidyl derivatives of 4-phenylazetidin-2-one as inhibitors of elastase and papain". . p. 243 - 253. Retrieved 2007/10/03.