CAS 10537-47-0|Malonoben

Introduction：Basic information about CAS 10537-47-0|Malonoben, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Malonoben BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles23
8. Synonyms

Common Name	Malonoben
CAS Number	10537-47-0	Molecular Weight	282.380
Density	1.1±0.1 g/cm3	Boiling Point	386.8±37.0 °C at 760 mmHg
Molecular Formula	C₁₈H₂₂N₂O	Melting Point	141-143℃ (ethanol )
MSDS	ChineseUSA	Flash Point	187.7±26.5 °C
Symbol	GHS06	Signal Word	Danger

Names

Name	malonoben
Synonym	More Synonyms

Malonoben BiologicalActivity

Description	Tyrphostin A9(AG 17), a tyrosine kinase inhibitor, is a potent inducer of mitochondrial fission. Tyrphostin A9 emerged as the most potent and selective of 51 tyrosine kinase inhibitors tested against the TNF-induced respiratory burst. IC50 value: Target: Multi tyrosine kinaseTyrphostin A9 inhibited TNF-induced tyrosine phosphorylation of pyk2 without blocking the cells' bactericidal activity. Tyrphostin A9 is a PDGF receptor tyrosine kinase inhibitor (IC50 = 500 nM). Recent findings suggest that signaling via PDGF receptor tyrosine kinases is not necessary for the shift of the smooth muscle cells from a contractile to a synthetic phenotype. On the other hand these enzymes apparently carry out important functions in the control of intracellular membrane traffic and cell division.
Related Catalog	Research Areas >>Cancer
References	[1]. Park SJ, Park YJ, Shin JH, et al. A receptor tyrosine kinase inhibitor, Tyrphostin A9 induces cancer cell death through Drp1 dependent mitochondria fragmentation. Biochem Biophys Res Commun. 2011 May 13;408(3):465-70. [2]. Richard F. Loeser, Christopher B. Forsyth, Allen M. Samarel et al. Fibronectin Fragment Activation of Proline-rich Tyrosine Kinase PYK2 Mediates Integrin Signals Regulating Collagenase-3 Expression by Human Chondrocytes through a Protein Kinase C-dependent Pathway. The Journal of Biological Chemistry, 2003, 278, 24577-24585. [3]. Michele Fuortes, Maxine Melchior, Hyunsil Han, et al. Role of the tyrosine kinase pyk2 in the integrin-dependent activation of human neutrophils by TNF. J Clin Invest. 1999;104(3):327-335. [4]. Johan Thyberg . Tyrphostin A9 and wortmannin perturb the Golgi complex and block proliferation of vascular smooth muscle cells. European Journal of Cell Biology.1998,76(1): 33-42 [5]. R Marhaba, F Mary, C Pelassy, et al. Tyrphostin A9 inhibits calcium release-dependent phosphorylations and calcium entry via calcium release-activated channel in Jurkat T cells. The Journal of Immunology. 1996,157 (4): 1468-1473

Description

Tyrphostin A9(AG 17), a tyrosine kinase inhibitor, is a potent inducer of mitochondrial fission. Tyrphostin A9 emerged as the most potent and selective of 51 tyrosine kinase inhibitors tested against the TNF-induced respiratory burst. IC50 value: Target: Multi tyrosine kinaseTyrphostin A9 inhibited TNF-induced tyrosine phosphorylation of pyk2 without blocking the cells' bactericidal activity. Tyrphostin A9 is a PDGF receptor tyrosine kinase inhibitor (IC50 = 500 nM). Recent findings suggest that signaling via PDGF receptor tyrosine kinases is not necessary for the shift of the smooth muscle cells from a contractile to a synthetic phenotype. On the other hand these enzymes apparently carry out important functions in the control of intracellular membrane traffic and cell division.

Related Catalog

Research Areas >>Cancer

References

[1]. Park SJ, Park YJ, Shin JH, et al. A receptor tyrosine kinase inhibitor, Tyrphostin A9 induces cancer cell death through Drp1 dependent mitochondria fragmentation. Biochem Biophys Res Commun. 2011 May 13;408(3):465-70.

[2]. Richard F. Loeser, Christopher B. Forsyth, Allen M. Samarel et al. Fibronectin Fragment Activation of Proline-rich Tyrosine Kinase PYK2 Mediates Integrin Signals Regulating Collagenase-3 Expression by Human Chondrocytes through a Protein Kinase C-dependent Pathway. The Journal of Biological Chemistry, 2003, 278, 24577-24585.

[3]. Michele Fuortes, Maxine Melchior, Hyunsil Han, et al. Role of the tyrosine kinase pyk2 in the integrin-dependent activation of human neutrophils by TNF. J Clin Invest. 1999;104(3):327-335.

[4]. Johan Thyberg . Tyrphostin A9 and wortmannin perturb the Golgi complex and block proliferation of vascular smooth muscle cells. European Journal of Cell Biology.1998,76(1): 33-42

[5]. R Marhaba, F Mary, C Pelassy, et al. Tyrphostin A9 inhibits calcium release-dependent phosphorylations and calcium entry via calcium release-activated channel in Jurkat T cells. The Journal of Immunology. 1996,157 (4): 1468-1473

Chemical & Physical Properties

Density	1.1±0.1 g/cm3
Boiling Point	386.8±37.0 °C at 760 mmHg
Melting Point	141-143℃ (ethanol )
Molecular Formula	C₁₈H₂₂N₂O
Molecular Weight	282.380
Flash Point	187.7±26.5 °C
Exact Mass	282.173218
PSA	67.81000
LogP	4.81
Vapour Pressure	0.0±0.9 mmHg at 25°C
Index of Refraction	1.555
InChIKey	MZOPWQKISXCCTP-UHFFFAOYSA-N
SMILES	CC(C)(C)c1cc(C=C(C#N)C#N)cc(C(C)(C)C)c1O
Storage condition	Store at RT
Water Solubility	ethanol: 20 mg/mL

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OO3737000

CHEMICAL NAME :: Malononitrile, 3,5-di-tert-butyl-4-hydroxybenzylidene-

CAS REGISTRY NUMBER :: 10537-47-0

BEILSTEIN REFERENCE NO. :: 2700764

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C18-H22-N2-O

MOLECULAR WEIGHT :: 282.42

WISWESSER LINE NOTATION :: NCYCN&U1R DQ CX1&1&1 EX1&1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 87 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SPEADM Special Publication of the Entomological Society of America. (4603 Calvert Rd., College Park, MD 20740) Volume(issue)/page/year: 78-1,21,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Administration onto the skin

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 226 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: SPEADM Special Publication of the Entomological Society of America. (4603 Calvert Rd., College Park, MD 20740) Volume(issue)/page/year: 74-1,-,1974

Safety Information

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301-H311-H331
Precautionary Statements	P261-P280-P301 + P310-P311
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T: Toxic;
Risk Phrases	R23/24/25
Safety Phrases	S36/37/39-S45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	OO3737000
Hazard Class	6.1
HS Code	2926909090

Customs

HS Code	2926909090
Summary	HS:2926909090 other nitrile-function compounds VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:6.5% General tariff:30.0%

Articles23

Pyk2 uncouples metabotropic glutamate receptor G protein signaling but facilitates ERK1/2 activation.

Mol. Brain 3 , 4, (2010)

Group I metabotropic glutamate receptors (mGluRs) are coupled via Galphaq/11 to the activation of phospholipase Cbeta, which hydrolyzes membrane phospholipids to form inositol 1,4,5 trisphosphate and ...

Abolition of mitochondrial substrate-level phosphorylation by itaconic acid produced by LPS-induced Irg1 expression in cells of murine macrophage lineage.

FASEB J. 30 , 286-300, (2016)

Itaconate is a nonamino organic acid exhibiting antimicrobial effects. It has been recently identified in cells of macrophage lineage as a product of an enzyme encoded by immunoresponsive gene 1 (Irg1...

Vesicular transport and apotransferrin in intestinal iron absorption, as shown in the Caco-2 cell model.

Am. J. Physiol. Gastrointest. Liver Physiol. 290 , G301-G309, (2006)

The potential roles of vesicular transport and apotransferrin (entering from the blood) in intestinal Fe absorption were investigated using Caco-2 cell monolayers with tight junctions in bicameral cha...

Synonyms

(3,5-Di-tert-butyl-4-hydroxybenzyliden)malononitril

2-(3,5-di-tert-butyl-4-hydroxybenzylidene)malononitrile

Malonoben

MFCD00209853

2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile

(3,5-Di-tert-butyl-4-hydroxybenzylidene)malononitrile

Tyrphostin AG17

Tyrphostin 9

2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]propanedinitrile

[4-Hydroxy-3,5-bis(2-methyl-2-propanyl)benzylidene]malononitrile

GCP 5126

Propanedinitrile, 2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-

(3,5-di-tert-butyl-4-hydroxybenzylidene)propanedinitrile

Caswell No. 291AA

[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile

3,5-di-tert-butyl-4-hydroxybenzylidene-malononitrile

tyrphostin A9

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