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

• ChemBase ID: 105106
• Molecular Formular: C18H22N2O
• Molecular Mass: 282.38008
• Monoisotopic Mass: 282.17321333
• SMILES: CC(C)(C)c1cc(C=C(C#N)C#N)cc(c1O)C(C)(C)C
• Canonical SMILES: N#CC(=Cc1cc(c(c(c1)C(C)(C)C)O)C(C)(C)C)C#N
• InChI: InChI=1S/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3
• InChIKey: MZOPWQKISXCCTP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile
• IUPAC Traditional name: 2-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile
• Synonyms: Malonoben; [[3,5-bis(1,1-Dimethylethyl)-4-hydroxyphenyl]methylene]propanedinitrile; Tyrphostin A9; RG-50872; TYRPHOSTIN A9; Tyrphostin AG 17; Malonaben; NSC 242557; Tyrphostin 9 (SF 6847)

Database IDs

• CAS Number: 10537-47-0
• MDL Number: MFCD00209853
• PubChem SID: 162093278; 24278069
• PubChem CID: 5614

CALCULATED PROPERTIES

• Acid pKa: 8.793973
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.958888
• LogD (pH = 7.4): 4.9420214
• Log P: 4.9591074
• Molar Refractivity: 86.4055 cm^3
• Polarizability: 32.390793 Å^3
• Polar Surface Area: 67.81 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: <25 mg/mL; ethanol: soluble20 mg/mL; H2O: insoluble
• Apperance: yellow solid

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: OO3737000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 23/24/25
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H331
• GHS Precautionary statements: P261-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Target: EGFR
• Gene Information: human ... EGFR(1956), ORAI1(84876), PDGFRA(5156), PDGFRB(5159)mouse ... Eef2k(13631), Prkaca(18747), Prkca(18750), Src(20779)

Product Information

• Purity: >99%
• Salt Data: Free Base

DETAILS

MP Biomedicals - 02158819

Purity: >99%
Tyrphostin 9 is a selective inhibitor of the PDGF receptor tyrosine kinase (IC₅₀ =1.2 μM)^1,2 . It is also a potent (10 nM) uncoupler of oxidative phosphorylation^3 .

Sigma Aldrich - T182

Biochem/physiol Actions
Inhibitor of calcium release-activated calcium (CRAC) channels (see Dennis et al.)
Selective inhibitor of PDGF receptor tyrosine kinase.

REFERENCES

• Levitzki, A. and Gilon, Trends Pharmacol. Sci. , 12 : 171, (1991).
• Bilder, G.E., et al., Am. J. Physiol. , 260 : C721, (1991).
• Terada, H., Biochem. Biophys. Acta , 639 : 225, (1981).