| Identification | More | [Name]
ROTTLERIN | [CAS]
82-08-6 | [Synonyms]
3'-[(8-CINNAMOYL-5,7-DIHYDROXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-6-YL)METHYL]-2',4',6'-TRIHYDROXY-5'-METHYLACETOPHENONE
MALLOTOXIN
ROTTLERIN
4’,6’-trihydroxy-5’-methyl-methyl)-2
acetophenone,3’-((8-cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2h-1-benzopyran-6-yl)
kamalin
(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
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
3'-[(8-Cinnamoyl-5,7-dihydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)methyl]-2',4',6'-trihydroxy-5'-methylacetophenone | [EINECS(EC#)]
201-395-4 | [Molecular Formula]
C30H28O8 | [MDL Number]
MFCD00017361 | [Molecular Weight]
516.54 | [MOL File]
82-08-6.mol |
| Chemical Properties | Back Directory | [Appearance]
orange to brown powder | [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 | [pka]
6.92±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. | [LogP]
8.660 (est) | [CAS DataBase Reference]
82-08-6(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [RTECS ]
AM6913800
| [HS Code ]
29329990 |
| Hazard Information | Back Directory | [Description]
Rottlerin (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 Properties]
orange to brown powder | [Uses]
Rottlerin is a human ether-a-go-go-related gene (hERG) potassium channel activator. | [Definition]
ChEBI: 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 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. | [Biological Activity]
Originally 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 Actions]
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. | [storage]
+4°C | [References]
1) 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 |
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