ChemicalBook > CAS DataBase List > Octanoic acid, 6,8-bis[(phenylMethyl)thio]-

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

Product Name
Octanoic acid, 6,8-bis[(phenylMethyl)thio]-
CAS No.
95809-78-2
Chemical Name
Octanoic acid, 6,8-bis[(phenylMethyl)thio]-
Synonyms
CPI-613;Devimistat;CPI-613, >98%;CPI 613;CPI613;CPI-613(Devimistat);Devimistat (CPI-613);CPI-613;CPI 613;CPI613;Devimistat, 10 mM in DMSO;6,8-Bis(benzylthio)octanoic acid;alpha-lipoic acid analogue CPI-613
CBNumber
CB52554078
Molecular Formula
C22H28O2S2
Formula Weight
388.59
MOL File
95809-78-2.mol
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Octanoic acid, 6,8-bis[(phenylMethyl)thio]- Property

Melting point:
63-65℃
Boiling point:
553.0±50.0 °C(Predicted)
Density 
1.149
storage temp. 
2-8°C
solubility 
DMSO: soluble15mg/mL (clear solution)
pka
4.75±0.10(Predicted)
form 
powder
color 
white to beige
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChI
InChI=1S/C22H28O2S2/c23-22(24)14-8-7-13-21(26-18-20-11-5-2-6-12-20)15-16-25-17-19-9-3-1-4-10-19/h1-6,9-12,21H,7-8,13-18H2,(H,23,24)
InChIKey
ZYRLHJIMTROTBO-UHFFFAOYSA-N
SMILES
C(O)(=O)CCCCC(SCC1=CC=CC=C1)CCSCC1=CC=CC=C1
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Safety

Hazard Codes 
N
Risk Statements 
50/53
Safety Statements 
60-61
RIDADR 
UN 3077 9 / PGIII
WGK Germany 
3
HS Code 
2930.90.2900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0404
Product name
6,8-Bis(benzylthio)-octanoic acid
Purity
≥98% (HPLC)
Packaging
5mg
Price
$105.45
Updated
2025/07/31
Sigma-Aldrich
Product number
SML0404
Product name
6,8-Bis(benzylthio)-octanoic acid
Purity
≥98% (HPLC)
Packaging
25mg
Price
$441
Updated
2025/07/31
TCI Chemical
Product number
B5368
Product name
6,8-Bis(benzylthio)octanoic Acid
Packaging
5MG
Price
$112
Updated
2025/07/31
TCI Chemical
Product number
B5368
Product name
6,8-Bis(benzylthio)octanoic Acid
Packaging
25MG
Price
$388
Updated
2025/07/31
Cayman Chemical
Product number
16981
Product name
CPI-613
Purity
≥98%
Packaging
5mg
Price
$39
Updated
2024/03/01
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Octanoic acid, 6,8-bis[(phenylMethyl)thio]- Chemical Properties,Usage,Production

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.

Uses

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 cells
  • to induce α-smooth muscle actin (αSMA) and pro-collagen I expression and to assess PDH enzyme activity in whole-cell lysates
  • to validate basal respiration in tissue respirometry

Biochem/physiol Actions

6,8-Bis(benzylthio)-octanoic acid (CPI-613) is a lipoate analog. It acts as a mitochondrial disrupter by blocking the mitochondrial enzymes pyruvate dehydrogenase and α-ketoglutarate dehydrogenase.

storage

Store at +4°C

References

[1] ZUZANA ZACHAR. Non-redox-active lipoate derivates disrupt cancer cell mitochondrial metabolism and are potent anticancer agents in vivo.[J]. Journal of Molecular Medicine-Jmm, 2011, 89 11: 1137-1148. DOI:10.1007/s00109-011-0785-8
[2] SHAWN D STUART. A strategically designed small molecule attacks alpha-ketoglutarate dehydrogenase in tumor cells through a redox process.[J]. Cancer & Metabolism, 2014: 4. DOI:10.1186/2049-3002-2-4
[3] BASTIAN DÖRSAM  Jörg F. The disulfide compound α-lipoic acid and its derivatives: A novel class of anticancer agents targeting mitochondria[J]. Cancer letters, 2016, 371 1: Pages 12-19. DOI:10.1016/j.canlet.2015.11.019
[4] BETHANY R MORDHORST. Pharmacologic Reprogramming Designed to Induce a Warburg Effect in Porcine Fetal Fibroblasts Alters Gene Expression and Quantities of Metabolites from Conditioned Media Without Increased Cell Proliferation.[J]. Cellular reprogramming, 2018, 20 1: 38-48. DOI:10.1089/cell.2017.0040
[5] YUKI EGAWA. Therapeutic potential of CPI-613 for targeting tumorous mitochondrial energy metabolism and inhibiting autophagy in clear cell sarcoma.[J]. PLoS ONE, 2018: e0198940. DOI:10.1371/journal.pone.0198940

Octanoic acid, 6,8-bis[(phenylMethyl)thio]- Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Octanoic acid, 6,8-bis[(phenylMethyl)thio]- manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
CPI 613 95809-78-2
Price
US $0.00-0.00/KG
Min. Order
5mg
Purity
99% HPLC
Supply Ability
2000tons
Release date
2019-12-30

95809-78-2, Octanoic acid, 6,8-bis[(phenylMethyl)thio]-Related Search:


  • alpha-lipoic acid analogue CPI-613
  • CPI-613
  • CPI-613; OCTANOIC ACID, 6,8-BIS[(PHENYLMETHYL)THIO]-
  • Octanoic acid, 6,8-bis[(phenylMethyl)thio]-
  • 6,8-Bis(benzylthio)octanoic acid
  • 6,8-Bis[(phenylmethyl)thio]octanoic acid
  • 6,8-Bis[(phenylmethyl)thio]octanoic acid CPI-613
  • 6,8-Bis(benzylsulfanyl)octanoic acid
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  • CPI-613(Devimistat)
  • CPI-613;CPI 613;CPI613
  • CPI-613, >98%
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  • CPI613; CPI-613; CPI 613; DEVIMISTAT
  • Octanoic acid, 6,8-bis[(phenylMethyl)thio]- USP/EP/BP
  • Devimistat (CPI-613)
  • 6,8-Bis(benzylsulfanyl)octanoicaci
  • Devimistat, 10 mM in DMSO
  • 95809-78-2
  • Inhibitor
  • Inhibitors