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  • SML0404
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SML0404

Sigma-Aldrich

6,8-Bis(benzylthio)-octanoic acid

≥98% (HPLC)

Synonym(s):
6,8-Bis[(phenylmethyl)thio-octanoic acid, CPI-613
Empirical Formula (Hill Notation):
C22H28O2S2
CAS Number:
Molecular Weight:
388.59
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL (clear solution)

storage temp.

2-8°C

SMILES string

OC(=O)CCCCC(CCSCc1ccccc1)SCc2ccccc2

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)

InChI key

ZYRLHJIMTROTBO-UHFFFAOYSA-N

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This Item
ALD0010836320043081
assay

≥98% (HPLC)

assay

≥95% (HPLC)

assay

98%

assay

≥98.0% (HPLC)

form

powder

form

powder

form

liquid crystal

form

solid

color

white to beige

color

-

color

-

color

-

solubility

DMSO: 15 mg/mL (clear solution)

solubility

-

solubility

-

solubility

-

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

storage temp.

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

Application

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.
6,8-Bis(benzylthio)-octanoic acid is an E1α pyruvate dehydrogenase (PDH) modulator that prevents cancer cells from metabolizing glucose for energy. 6,8-Bis(benzylthio)-octanoic acid has been granted orphan drug status by the US FDA for pancreatic cancer.

Other Notes

Air Sensitive

Pictograms

Environment

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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