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3785-90-8

3785-90-8 structure
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: 2025-08-22 03:50:38
  • 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
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
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
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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