1,2-Dithiolane-3-pentanoic acid 1-oxide

Base Information

• Chemical Name: 1,2-Dithiolane-3-pentanoic acid 1-oxide
• CAS No.: 6992-30-9
• Molecular Formula: C8H14O3S2
• Molecular Weight: 222.32
• Mol file: 6992-30-9.mol

Synonyms:1,2-dithiolane-3-pentanoic acid 1-oxide;rac-lipoic acid impurity 2 (S-Oxide);5-(1-oxido-1,2-dithiolan-3-yl)pentanoic acid;Rac-lipoic acid impurity E;Thioctic acid impurity 3;Protogen-B;Thioctic acid impurity 8;5-(1-oxodithiolan-3-yl)pentanoic acid;

Chemical Property of 1,2-Dithiolane-3-pentanoic acid 1-oxide

Chemical Property:

• Boiling Point: 444.9±37.0 °C(Predicted)
• PKA: 4.73±0.10(Predicted)
• PSA: 98.88000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 2.66630

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Protogen B is a thiosulfinate of alpha lipoic acid which is an antioxidant and a fat-metabolism stimulator.

Technology Process of 1,2-Dithiolane-3-pentanoic acid 1-oxide

There total 5 articles about 1,2-Dithiolane-3-pentanoic acid 1-oxide 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:

Thioctic acid (1077-28-7,62-46-4) → 1-oxide-β-lipoic acid (6992-30-9) + 2-oxide-β-lipoic acid (108015-78-7)

Guidance literature:

With 1,1'-sulfinylbisbenzene; Re(O)Cl₃(PPh₃)2; In dichloromethane; at 25 ℃;

DOI:10.1021/ja972013r

Reference yield:

1,2-dithiolane-3-pentanoic acid methyl ester (46236-19-5) → 1-oxide-β-lipoic acid (6992-30-9) + 2-oxide-β-lipoic acid (108015-78-7)

Guidance literature:

1,2-dithiolane-3-pentanoic acid methyl ester; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 1h;

With sodium hydroxide; In methanol; water; at 20 ℃; for 1h;

Reference yield:

benzyl 5-(1,2-dithiolan-3-yl)pentanoate → 1-oxide-β-lipoic acid (6992-30-9) + 2-oxide-β-lipoic acid (108015-78-7)

Guidance literature:

benzyl 5-(1,2-dithiolan-3-yl)pentanoate; With tert.-butylhydroperoxide; In N,N-dimethyl-formamide; at 20 ℃; for 8h;

With potassium hydroxide; In methanol; water; at 20 ℃; for 1h;

upstream raw materials:

Thioctic acid

1,2-dithiolane-3-pentanoic acid methyl ester

Refernces

• 1、 Donnelly, Daniel P.,Dowgiallo, Matthew G.,Salisbury, Joseph P.,Aluri, Krishna C.,Iyengar, Suhasini,Chaudhari, Meenal,Mathew, Merlit,Miele, Isabella,Auclair, Jared R.,Lopez, Steven A.,Manetsch, Roman,Agar, Jeffrey N.. "Cyclic Thiosulfinates and Cyclic Disulfides Selectively Cross-Link Thiols while Avoiding Modification of Lone Thiols". supporting information. p. 7377 - 7380. Retrieved 2018/06/11.
• 2、 McNeil, Nicole M. R.,McDonnell, Ciara,Hambrook, Miranda,Back, Thomas G.. "Oxidation of disulfides to thiolsulfinates with hydrogen peroxide and a cyclic seleninate ester catalyst peroxide and a cyclic seleninate ester catalyst". . p. 10748 - 10762. Retrieved 2015/08/11.