ROTTLERIN

ROTTLERIN Basic information
Product Name:ROTTLERIN
Synonyms:3'-[(8-CINNAMOYL-5,7-DIHYDROXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-YL)METHYL]-2',4',6'-TRIHYDROXY-5'-METHYLACETOPHENONE;4’,6’-trihydroxy-5’-methyl-methyl)-2;acetophenone,3’-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2h-1-benzopyran-6-yl);2-Propen-1-one, 1-[6-[(3-acetyl-2,4,6-trihydroxy-5-methylphenyl)methyl]-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-8-yl]-3-phenyl-, (2E)-;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;(E)-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;Rottlerin,98%;Rottlerin, 98% 10MG
CAS:82-08-6
MF:C30H28O8
MW:516.54
EINECS:201-395-4
Product Categories:Aromatic Phenols;Protein Kinase
Mol File:82-08-6.mol
ROTTLERIN Structure
ROTTLERIN Chemical Properties
Melting point 200 °C
Boiling point 521.39°C (rough estimate)
density 1.2051 (rough estimate)
refractive index 1.4900 (estimate)
storage temp. 2-8°C
solubility Soluble in DMSO (up to 50 mg/ml).
form Powder
pka6.92±0.40(Predicted)
color Orange to brown
Stability:Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
LogP8.660 (est)
CAS DataBase Reference82-08-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-22
Safety Statements 36/37-24/25
WGK Germany 3
RTECS AM6913800
HS Code 29329990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ROTTLERIN Usage And Synthesis
DescriptionRottlerin (82-08-6) has been reported to inhibit PKCδ selectively however this result has been called into question.1?Displays neuroprotective effects.2?Induces autophagy.3?Cell permeable.
Chemical Propertiesorange to brown powder
UsesRottlerin is a human ether-a-go-go-related gene (hERG) potassium channel activator.
DefinitionChEBI: A chromenol that is 2,2-dimethyl-2H-chromene substituted by hydroxy groups at positions 5 and 7, a 3-acetyl-2,4,6-trihydroxy-5-methylbenzyl group at position 6 and a (1E)-3-oxo-1-phenylprop-1-en-3-yl group at position 8. A potassium channel opener, it is isolated from Mallotus philippensis.
General DescriptionRottlerin 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.
Biological ActivityOriginally reported to inhibit PKC isoforms, with selectivity for PKC δ (K i values are 30, 42, 40, 3-6, 100, and 100 μ M for α , β , γ , δ , ε , λ respectively). Also reported to inhibit CAM kinase III. However, recently shown to inhibit a wide range of protein kinases, and most potently to inhibit PRAK and MAPKAP-K2 (IC 50 values are 1.9 and 5 μ M respectively). Also shown to act as a direct mitochondrial uncoupler.
Biochem/physiol ActionsRecently, 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.
storage+4°C
References1) Davies et al. (2000), Specificity and mechanism of action of some commonly used protein kinase inhibitors; Biochem. J., 351 95 2) Zhang et al. (2007), Neuroprotective effect of protein kinase C delta inhibitor rottlerin in cell culture and animal models of Parkinson’s disease; J. Pharmacol. Exp. Ther., 322 913 3) Balgi et al. (2009), Screen for chemical modulators of autophagy reveals novel therapeutic inhibitors of mTORC1 signaling; PLoS One, 4 e7124
ROTTLERIN Preparation Products And Raw materials
2-(4-Methoxybenzyl)phenol 2',4'-DIHYDROXY-3'-METHYLACETOPHENONE 2-BENZYL-4-METHYLPHENOL ALLYL P-TOLYL ETHER 2,4-DIHYDROXY-1,3,5-TRIMETHYLBENZENE 2,4,6-TRIMETHYLANISOLE 2,2'-METHYLENEBIS(4-METHYLPHENOL) 3-(2-METHOXY-5-METHYLPHENYL)-1-PROPENE 2,4,6-TRIHYDROXY-1,3-DIMETHYL BENZENE 2'-HYDROXY-5'-METHYLCHALCONE 2,4-Dihydroxy-3-methylbenzaldehyde 1-(3-ETHYL-2,6-DIHYDROXYPHENYL)ETHAN-1-ONE 3,5-DIMETHYL-4-HYDROXYACETOPHENONE 1-(2-Hydroxy-5-methylphenyl)ethanone 3',5'-Dimethyl-2'-hydroxyacetophenone 1-(2-ETHOXY-5-METHYL-PHENYL)-ETHANONE 3,5-DIMETHYLACETOPHENONE 3-Ethylacetophenone

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