Skip to Content
Merck
All Photos(1)

Documents

SML0404

Sigma-Aldrich

6,8-Bis(benzylthio)-octanoic acid

≥98% (HPLC)

Synonym(s):

6,8-Bis[(phenylmethyl)thio-octanoic acid, CPI-613

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

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
  • 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

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

Pictograms

Environment
GHS09

Signal Word

Warning

Hazard Statements

H410

Precautionary Statements

P273 - P391 - P501

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

2-Deoxy-D-glucose ≥99% (GC), crystalline

Sigma-Aldrich

D6134

2-Deoxy-D-glucose

Alexander Strom et al.
Molecular metabolism, 43, 101114-101114 (2020-11-10)
The lack of effective treatments against diabetic sensorimotor polyneuropathy demands the search for new strategies to combat or prevent the condition. Because reduced magnesium and increased methylglyoxal levels have been implicated in the development of both type 2 diabetes and
Bethany R Mordhorst et al.
Scientific reports, 9(1), 9417-9417 (2019-07-03)
A metabolic phenomenon known as the Warburg effect has been characterized in certain cancerous cells, embryonic stem cells, and other rapidly proliferative cell types. Previously, our attempts to induce a Warburg-like state pharmaceutically via CPI-613 and PS48 treatment did augment
Edward R Smith et al.
Scientific reports, 10(1), 17914-17914 (2020-10-23)
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
Mattia Quattrocelli et al.
JCI insight, 4(24) (2019-12-20)
In humans, chronic glucocorticoid use is associated with side effects like muscle wasting, obesity, and metabolic syndrome. Intermittent steroid dosing has been proposed in Duchenne Muscular Dystrophy patients to mitigate the side effects seen with daily steroid intake. We evaluated
Xiaojing Liu et al.
Cell, 175(2), 502-513 (2018-09-25)
Acetate is a major nutrient that supports acetyl-coenzyme A (Ac-CoA) metabolism and thus lipogenesis and protein acetylation. However, its source is unclear. Here, we report that pyruvate, the end product of glycolysis and key node in central carbon metabolism, quantitatively generates acetate

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service