Octanoic acid, 6,8-bis[(phenylMethyl)thio]-

Base Information

• Chemical Name: Octanoic acid, 6,8-bis[(phenylMethyl)thio]-
• CAS No.: 95809-78-2
• Molecular Formula: C22H28O2S2
• Molecular Weight: 388.595
• Mol file: 95809-78-2.mol

Synonyms:6,8-bis(benzylthio)octanoic acid;

Chemical Property of Octanoic acid, 6,8-bis[(phenylMethyl)thio]-

Chemical Property:

• Melting Point: 63-65℃
• Boiling Point: 553.0±50.0 °C(Predicted)
• PKA: 4.75±0.10(Predicted)
• PSA: 87.90000
• Density: 1.149
• LogP: 6.25690
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble15mg/mL (clear solution)

Purity/Quality:

98%,99%, ^*data from raw suppliers

CPI613 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61

MSDS Files:

SDS file from LookChem

Useful:

• Description: CPI-613 (95809-78-2) is a lipoic acid analog which potently disrupts mitochondrial metabolism with selectivity for tumor cells in vitro and shows strong antitumor activity in vivo.1?? Inhibits alpha-ketoglutarate dehydrogenase (KGDH) by a redox mechanisms selectively in tumor cells.2 Inhibits pyruvate dehydrogenase (PDH) as a mechanistically distinct, non-redox, effect.1,2 A novel anticancer agent with a mitochondria-targeted mode of action with non-genotoxic properties.3. Has been used (along with PS48) to induce a Warburg-like metabolic state in fibroblasts.4 Combination treatment of CPI-613 and chloroquine inhibits the progression of clear cell sarcoma in a mouse model.5
• Uses: CPI 613 is a class of non-redox-active lipoate derivative that disrupts cancer cell mitochondrial metabolism and are potent anticancer agents in vivo. 6,8-Bis(benzylthio)-octanoic acid has been used as pyruvate dehydrogenase (PDH) inhibitor:to study its effects on neurite outgrowth in primary mouse dorsal root ganglia cellsto induce α-smooth muscle actin (αSMA) and pro-collagen I expression and to assess PDH enzyme activity in whole-cell lysatesto validate basal respiration in tissue respirometry

Technology Process of Octanoic acid, 6,8-bis[(phenylMethyl)thio]-

There total 6 articles about Octanoic acid, 6,8-bis[(phenylMethyl)thio]- 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:

dihydrothioctic acid sodium salt (36915-02-3) + benzyl bromide (100-39-0) → (+/-)6,8-bis-thiobenzyl octanoic acid (95809-78-2)

Guidance literature:

dihydrothioctic acid sodium salt; benzyl bromide; With sodium hydroxide; In water; at 20 ℃; for 2h; Large scale reaction;

With hydrogenchloride; In water; ethyl acetate; pH=2;

DOI:10.1021/op200091t

Reference yield:

phenylmethanethiol (100-53-8) → (+/-)6,8-bis-thiobenzyl octanoic acid (95809-78-2)

Guidance literature:

With ethanol; sodium ethanolate; Behandeln des erhaltenen Reaktionsgemisches mit KOH;

DOI:10.1021/ja01607a057

Reference yield:

phenylmethanethiol (100-53-8) → (+/-)6,8-bis-thiobenzyl octanoic acid (95809-78-2)

Guidance literature:

With ethanol; sodium ethanolate; Behandeln des erhaltenen Reaktionsgemisches mit KOH;

DOI:10.1021/ja01607a057

upstream raw materials:

benzyl chloride

phenylmethanethiol

dihydrothioctic acid sodium salt

benzyl bromide

Downstream raw materials:

N^ε-(6,8-Dibenzylthio-octanoyl)-L-lysin

Refernces

• 1、 Moro. "CPI-613: Antimitochondrial metabolism agent Treatment of hematological malignancies and solid tumors". . p. 209 - 214. Retrieved 2017/05/17.