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Merck
CN

R5648

Rottlerin

Synonym(s):

1-[6-[(3-Acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-2-propen-1-one, Mallotoxin

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About This Item

Empirical Formula (Hill Notation):
C30H28O8
CAS Number:
82-08-6
Molecular Weight:
516.54
NACRES:
NA.77
PubChem Substance ID:
24278679
UNSPSC Code:
12352200
EC Number:
201-395-4
MDL number:
MFCD00017361

Key Documents

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InChI key

DEZFNHCVIZBHBI-ZHACJKMWSA-N

InChI

1S/C30H28O8/c1-15-24(33)19(27(36)22(16(2)31)25(15)34)14-20-26(35)18-12-13-30(3,4)38-29(18)23(28(20)37)21(32)11-10-17-8-6-5-7-9-17/h5-13,33-37H,14H2,1-4H3/b11-10+

SMILES string

CC(=O)c1c(O)c(C)c(O)c(Cc2c(O)c3C=CC(C)(C)Oc3c(c2O)C(=O)\C=C\c4ccccc4)c1O

biological source

plant (Mallotus philippinensis)

assay

≥95% (HPLC)

form

powder

mp

200.0 °C

solubility

ethanol: 1 mg/mL

storage temp.

2-8°C

Gene Information

human ... CDK2(1017)

General description

Rottlerin is extracted from Mallotus philippinensis. It is a protein kinase Cδ (PKCδ) inhibitor. Rottlerin acts as an uncoupler of mitochondrial respiration from oxidative phosphorylation. It has antitumor, autophagy, anti-proliferative, anti-metastasis and anti-invasive properties.

Application

Rottlerin has been used:
  • as a protein kinase C δ (PKCδ) inhibitor for the analysis of protein content and phosphorylation in rats
  • to examine the gene expression of early osteoblast markers
  • to attenuate pyruvate dehydrogenase (PDH) phosphorylation by succinate
  • to depolarise mitochondria
  • to investigate its antitumor activity in pancreatic cancer (PC) cells

Biochem/physiol Actions

Potent activator of the large conductance voltage and Ca2+ activated K+ channel; hERG channel activator.
Recently, Rottlerin (mallotoxin) has been shown to be a potent activator of the large conductance voltage and Ca2 activated K+ channel and to potently leftward shift the conductance-voltage relationship of the channel. Mallatoxin tested on hERG channels increased both step and tail hERG current by leftward shifting the voltage dependence of hERG activation and slowing channel deactivation. These actions distinguish Mallatoxin as a novel naturally occurring hERG channel activator.

Features and Benefits

This compound is featured on the PKC page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLBS1540V
SLBN6603V
SLBL9875V
SLBK1298V
SLBD3670V

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The unfolded protein response plays a predominant homeostatic role in response to mitochondrial stress in pancreatic stellate cells
Su HY, et al.
Testing, 11(2), e0148999-e0148999 (2016)
Haoyu Zeng et al.
The Journal of pharmacology and experimental therapeutics, 319(2), 957-962 (2006-08-25)
Human ether-a-go-go-related gene (hERG) encodes a rapidly activating delayed rectifier potassium channel that plays important roles in cardiac action potential repolarization. Although many drugs and compounds block hERG channels, activators of the channel have only recently been described. Three structurally
Succinate accumulation impairs cardiac pyruvate dehydrogenase activity through GRP91-dependent and independent signaling pathways: Therapeutic effects of ginsenoside Rb1
Li J, et al.
Biochimica et Biophysica Acta (BBA)-Molecular Basis of Disease, 1863(11), 2835-2847 (2017)
Jui-Ling Hsu et al.
Biochemical pharmacology, 84(1), 59-67 (2012-04-12)
Combination therapy, which can optimize killing activity to cancers and minimize drug resistance, is a mainstream therapy against hormone-refractory prostate cancers (HRPCs). Rottlerin, a natural polyphenolic component, synergistically increased PC-3 (a HRPC cell line) apoptosis induced by camptothecin (a topoisomerase
Intermittent Administration of Parathyroid Hormone 1-34 Enhances Osteogenesis of Human Mesenchymal Stem Cells by Regulating Protein Kinase Cdelta
Kuo SW, et al.
International Journal of Molecular Sciences, 18(10), 2221-2221 (2017)
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