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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

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5 MG
$105.45
25 MG
$441.00

About This Item

Empirical Formula (Hill Notation):
C22H28O2S2
CAS Number:
95809-78-2
Molecular Weight:
388.59
MDL number:
MFCD22420826
UNSPSC Code:
12352106
PubChem Substance ID:
329825400
NACRES:
NA.77

$105.45

List Price$111.00
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order

Quality Level

100

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

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[1]
  • to induce α-smooth muscle actin (αSMA) and pro-collagen I expression and to assess PDH enzyme activity in whole-cell lysates[2]
  • to validate basal respiration in tissue respirometry[3]

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.[4]
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.
6,8-Bis(benzylthio)-octanoic acid is an E1α pyruvate dehydrogenase (PDH) modulator.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

pictograms

Environment
GHS09

signalword

Warning

hcodes

H410

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000445108
0000445108
0000423373
0000423373
0000164783

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TGF-β1 reprograms metabolism in renal fibroblasts, inducing a switch from oxidative phosphorylation to aerobic glycolysis. However, molecular events underpinning this are unknown. Here we identify that TGF-β1 downregulates acetyl-CoA biosynthesis via regulation of the pyruvate dehydrogenase complex (PDC). Flow cytometry
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