Captopril disulfide

Base Information

• Chemical Name: Captopril disulfide
• CAS No.: 64806-05-9
• Molecular Formula: C18H28N2O6S2
• Molecular Weight: 432.562
• Hs Code.: 2933999552
• European Community (EC) Number: 613-693-5
• UNII: Y21D2C2453
• DSSTox Substance ID: DTXSID801024324
• Nikkaji Number: J228.010H
• Mol file: 64806-05-9.mol

Synonyms:captopril disulfide;SQ 14,551;SQ 14551;SQ-14,551;SQ-14551

Chemical Property of Captopril disulfide

Chemical Property:

• Melting Point: 224-226°C
• Boiling Point: 714.796 °C at 760 mmHg
• PKA: 3.29±0.20(Predicted)
• Flash Point: 386.095 °C
• PSA: 165.82000
• Density: 1.383 g/cm³
• LogP: 1.66700
• Storage Temp.: -20?C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly, Sonicated)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 432.13887896
• Heavy Atom Count: 28
• Complexity: 565

Purity/Quality:

98%Min ^*data from raw suppliers

Captopril Disulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CSSCC(C)C(=O)N1CCCC1C(=O)O)C(=O)N2CCCC2C(=O)O
• Isomeric SMILES: C[C@H](CSSC[C@@H](C)C(=O)N1CCC[C@H]1C(=O)O)C(=O)N2CCC[C@H]2C(=O)O
• Description: Captopril disulfide is a metabolite and symmetrical disulfide form of the angiotensin converting enzyme (ACE) inhibitor captopril . Captopril disulfide is the main degradation product of captopril and is formed by oxidation. It is a potential impurity in commercial preparations of captopril. Captopril disulfide inhibits angiotensin I-induced increases in mean arterial pressure in anesthetized dogs (ID50 = 0.231 mg/kg, i.v.).
• Uses: A metabolite of Captopril. A new antihypertensive agent Captopril Disulfide (Captopril EP Impurity A) is a metabolite of Captopril. A new antihypertensive agent.

Technology Process of Captopril disulfide

There total 6 articles about Captopril disulfide 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:

captopril (62571-86-2) + Allylglutathione sulphide → S-allylthio-captopril + Oxidized glutathione (27025-41-8,121-24-4,87140-29-2) + GLUTATHIONE (70-18-8) + S-glutathionylthio-captopril (78636-30-3) + Captopril disulfide (64806-05-9)

Guidance literature:

at 20 ℃; for 20h; pH=8.4; aq. buffer;

DOI:10.1016/j.ejmech.2010.01.031

Reference yield:

captopril (62571-86-2) → Captopril disulfide (64806-05-9) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With potassium metaperiodate; diperiodatocuprate(III); potassium nitrate; potassium hydroxide; In water; at 30 ℃; for 6h; Concentration; Temperature; Kinetics; Inert atmosphere;

DOI:10.1007/s00706-014-1329-z

Reference yield:

oxytocin (50-56-6) + captopril (62571-86-2) → H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2 (17912-60-6) + Captopril disulfide (64806-05-9)

Guidance literature:

In water; at 25 ℃; for 5h; Equilibrium constant; pH 7.0;

DOI:10.1006/bioo.1995.1009

upstream raw materials:

oxytocin

captopril

Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH₂

Downstream raw materials:

captopril

1-((S)-3-mercapto-2-methylpropanoyl)-L-prolyl-L-phenylalanine

C₁₉H₂₆N₂O₄S

C₃₆H₄₆N₄O₈S₂

Refernces

• 1、 Miron, Talia,Listowsky, Irving,Wilchek, Meir. "Reaction mechanisms of allicin and allyl-mixed disulfides with proteins and small thiol molecules". body text. p. 1912 - 1918. Retrieved 2010/07/04.