DC Chemicals Limited
China
Product Name: Tyrphostin 8
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Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: Propanedinitrile,2-[(4-hydroxyphenyl)methylene]-
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3785-90-8

3785-90-8 structure

Name: Tyrphostin 8
Chemical Name: 4-hydroxybenzylidenemalononitrile
CAS Number: 3785-90-8
Molecular Formula: C₁₀H₆N₂O
Molecular Weight: 170.17
Catalog: Chemical reagent Organic reagent Cyanide/nitrile
Create Date: 2018-07-06 10:22:08
Modify Date: 2024-01-03 17:56:03
Tyrphostin 8 is a tyrosine kinase, with an IC50 of 560 μM for EGFR kinase. Tyrphostin 8 is also a GTPase inhibitor. Tyrphostin 8 can inhibit the protein serine/threonine phosphatase calcineurin (IC50=21 μM)[1][2][3].

Name	4-hydroxybenzylidenemalononitrile
Synonyms	4-(HYDROXYBENZYLIDENE)-MALONONITRILE 4-Hydroxybenzylidenemalononitrile (4-Hydroxybenzylidene)malonitrile EINECS 223-253-0 2-[(4-hydroxyphenyl)methylidene]propanedinitrile MFCD00020189

Description	Tyrphostin 8 is a tyrosine kinase, with an IC50 of 560 μM for EGFR kinase. Tyrphostin 8 is also a GTPase inhibitor. Tyrphostin 8 can inhibit the protein serine/threonine phosphatase calcineurin (IC50=21 μM)[1][2][3].
Related Catalog	Signaling Pathways >> JAK/STAT Signaling >> EGFR Signaling Pathways >> Metabolic Enzyme/Protease >> Phosphatase Signaling Pathways >> Protein Tyrosine Kinase/RTK >> EGFR Signaling Pathways >> GPCR/G Protein >> Ras Research Areas >> Metabolic Disease
Target	EGFR:560 μM (IC50) calcineuin phosphatase:21 μM (IC50)
In Vitro	Tyrphostin 8 (10-100 μM; pretreated for 20 min) blocks the Carbachol-initiated PKCδ tyrosine phosphorylation and ERK1/2 activation in parotid acinar cells[1]. Tyrphostin 8 (10-100 μM) produces a rapid and large increase in the basal O2 consumption of parotid acinar[1]. Tyrphostin 8 (10-100 μM) reduces the parotid ATP content by ∼90% at the concentration of 100 μM[1]. Tyrphostin 8 increases apical-to-basolateral transport of insulin-transferrin conjugate by enhancing transferrin receptor-mediated transcytosis in filter-grown Caco-2 cell monolayer[2]. Western Blot Analysis[1] Cell Line: Parotid acinar cells Concentration: 10, 100 μM Incubation Time: Pretreated for 20 min Result: Reduced the increase in tyrosine phosphorylation of PKCδ initiated by carbachol. Reduced the activation of ERK1/2 by carbachol.
In Vivo	Tyrphostin 8 improves the glucose-lowering effect of Insulin-transferrin in Streptozotocin-induced diabetic rats[2].
References	[1]. Soltoff SP. Evidence that tyrphostins AG10 and AG18 are mitochondrial uncouplers that alter phosphorylation-dependent cell signaling. J Biol Chem. 2004 Mar 19;279(12):10910-8. [2]. Xia CQ, et, al. Tyrphostin-8 enhances transferrin receptor-mediated transcytosis in Caco-2- cells and inreases hypoglycemic effect of orally administered insulin-transferrin conjugate in diabetic rats. Pharm Res. 2001 Feb;18(2):191-5. [3]. Martin BL. Inhibition of calcineurin by the tyrphostin class of tyrosine kinase inhibitors. Biochem Pharmacol. 1998 Aug 15;56(4):483-8.

Density	1.29 g/cm3
Boiling Point	354.3ºC at 760 mmHg
Melting Point	186-189 °C
Molecular Formula	C₁₀H₆N₂O
Molecular Weight	170.17
Flash Point	168.1ºC
Exact Mass	170.04800
PSA	67.81000
LogP	1.82276
Index of Refraction	1.653
Storage condition	2-8°C
Water Solubility	ethanol: 20 mg/mL, clear

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OO4200000

CHEMICAL NAME :: Malononitrile, (p-hydroxybenzylidene)-

CAS REGISTRY NUMBER :: 3785-90-8

BEILSTEIN REFERENCE NO. :: 2209079

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C10-H6-N2-O

MOLECULAR WEIGHT :: 170.18

WISWESSER LINE NOTATION :: QR D1UYCN&CN

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

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

REFERENCE :: BCPCA6 Biochemical Pharmacology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1958- Volume(issue)/page/year: 14,1325,1965

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 65 mg/kg

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

REFERENCE :: NATUAS Nature. (Nature Subscription Dept., POB 1018, Manasguan, NJ 08736) V.1- 1869- Volume(issue)/page/year: 228,1315,1970

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301-H319
Precautionary Statements	P301 + P310-P305 + P351 + P338
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T: Toxic;
Risk Phrases	25
Safety Phrases	S45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	OO4200000
Packaging Group	III
Hazard Class	6.1
HS Code	2926909090

123-08-0

109-77-3

~98%

3785-90-8

Literature: Gopalakrishna Panicker, Rajesh Krishnan; Krishnapillai, Sreekumar Tetrahedron Letters, 2014 , vol. 55, # 15 p. 2352 - 2354

114569-19-6

109-77-3

~59%

3785-90-8

Literature: Sidhu, Anjali; Sharma; Rai, Mangat Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010 , vol. 49, # 2 p. 247 - 250

62309-99-3

3785-90-8

Literature: Ertel,W.; Friedrich,K. Chemische Berichte, 1977 , vol. 110, p. 86 - 95

100-67-4

3785-90-8

Literature: Ertel,W.; Friedrich,K. Chemische Berichte, 1977 , vol. 110, p. 86 - 95

90-15-3

123-08-0

109-77-3

3785-90-8

Detail

Literature: Maggi, Raimondo; Ballini, Roberto; Sartori, Giovanni; Sartorio, Raffaella Tetrahedron Letters, 2004 , vol. 45, # 11 p. 2297 - 2299

Precursor 6
123-08-0 109-77-3 114569-19-6 62309-99-3
100-67-4 90-15-3
DownStream 5
5553-97-9 19310-87-3 122520-81-4 6504-13-8
78016-54-3

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%

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