Quinaprilat

Base Information

• Chemical Name: Quinaprilat
• CAS No.: 82768-85-2
• Deprecated CAS: 85441-60-7
• Molecular Formula: C23H26N2O5
• Molecular Weight: 410.47
• Hs Code.: 2933492250
• NSC Number: 759825
• UNII: 34SSX5LDE5
• DSSTox Substance ID: DTXSID40868904
• Nikkaji Number: J380.139J
• Wikipedia: Quinaprilat
• Wikidata: Q7272073
• NCI Thesaurus Code: C95129
• RXCUI: 1546359
• Pharos Ligand ID: YTH5M12CZM2S
• Metabolomics Workbench ID: 49688
• ChEMBL ID: CHEMBL1733
• Mol file: 82768-85-2.mol

Synonyms:2-(2-((1-carboxy-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid;CI 928;CI-928;quinaprilat;quinaprilat, (3S-(2(R*(R*)),3R*))-isomer

Chemical Property of Quinaprilat

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Melting Point: 166-168 ºC
• Boiling Point: 674.5 ºC at 760 mmHg
• Flash Point: 361.7 ºC
• PSA: 106.94000
• Density: 1.289 g/cm³
• LogP: 2.41740
• Storage Temp.: Refrigerator
• Solubility.: DMSO: ≥23mg/mL
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 410.18417193
• Heavy Atom Count: 30
• Complexity: 619

Purity/Quality:

98%Min ^*data from raw suppliers

Quinaprilat ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N
• Statements: 25-50
• Safety Statements: 45-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)N1CC2=CC=CC=C2CC1C(=O)O)NC(CCC3=CC=CC=C3)C(=O)O
• Isomeric SMILES: C[C@@H](C(=O)N1CC2=CC=CC=C2C[C@H]1C(=O)O)N[C@@H](CCC3=CC=CC=C3)C(=O)O
• Uses: A metabolite of Quinapril, an angiotensin converting enzyme (ACE) inhibitor. Quinaprilat (Quinapril EP Impurity C) is a metabolite of Quinapril, an angiotensin converting enzyme (ACE) inhibitor.

Technology Process of Quinaprilat

There total 6 articles about Quinaprilat 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: 79.0%

quinapril hydrochloride (82586-55-8) → quinaprilate (82768-85-2,85441-60-7)

Guidance literature:

With sodium hydroxide; water; In methanol; Ambient temperature;

DOI:10.1021/jm00160a026

Reference yield: 44.0%

<3S-<2>,3R*>-2-<2-<<1-(ethoxycarbonyl)-3-phenylpropyl>amino>-1-oxopropyl>-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, ethyl ester (103733-35-3) → quinaprilate (82768-85-2,85441-60-7)

Guidance literature:

With sodium hydroxide; water; In methanol; Ambient temperature;

DOI:10.1021/jm00160a026

Reference yield:

quinapril (85441-61-8,82768-84-1) → ethanol (64-17-5) + quinaprilate (82768-85-2,85441-60-7)

Guidance literature:

With Tris-HCl buffer; human liver carboxylesterase pI 4.5; at 37 ℃; pH=7.4; Further Variations:; Reagents; Enzyme kinetics;

DOI:10.1248/bpb.20.869

upstream raw materials:

quinapril hydrochloride

<3S-<2>,3R*>-2-<2-<<1-(ethoxycarbonyl)-3-phenylpropyl>amino>-1-oxopropyl>-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, ethyl ester

quinapril

Downstream raw materials:

<3S-<2(R*),3α,11aβ>>-1,3,4,6,11,11a-hexahydro-3-methyl-1,4-dioxo-α-(2-phenylethyl)-2H-pyrazino<1,2-b>isoquinoline-2-acetic acid

Refernces

• 1、 Stanisz, Beata. "The stability of quinapril hydrochloride - A mixture of amorphous and crystalline forms (QHCl-AC) in solid phase". . p. 443 - 450. Retrieved 2007/10/03.
• 2、 Takai, Satomi,Matsuda, Ayuka,Usami, Yoshiko,Adachi, Tetsuo,Sugiyama, Tadashi,Katagiri, Yoshihiro,Tatematsu, Masae,Hirano, Kazuyuki. "Hydrolytic profile for ester- or amide-linkage by carboxylesterases pI 5.3 and 4.5 from human liver". . p. 869 - 873. Retrieved 2007/10/03.