Malonoben

Modify Date: 2024-01-09 09:28:25

Malonoben Structure
Malonoben structure
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 Chinese USA Flash Point 187.7±26.5 °C
Symbol GHS06
GHS06
Signal Word Danger

 Use of Malonoben


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.

 Names

Name malonoben
Synonym More Synonyms

 Malonoben Biological Activity

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
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
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
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

 Synthetic Route

~84%

Malonoben Structure

Malonoben

CAS#:10537-47-0

Literature: Hori, Hitoshi; Nagasawa, Hideko; Ishibashi, Masaki; Uto, Yoshihiro; Hirata, Akihiko; Saijo, Kouichi; Ohkura, Kazuto; Kirk, Kenneth L; Uehara, Yoshimasa Bioorganic and Medicinal Chemistry, 2002 , vol. 10, # 10 p. 3257 - 3265

 Precursor & DownStream

Precursor  2

DownStream  0

 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

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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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