Malonoben

Names

Preferred IUPAC name [(3,5-di-tert-Butyl-4-hydroxyphenyl)methylidene]propanedinitrile

Other names Tyrphostin A9; SF-6847; GCP5126; and AG-17

Identifiers

3D model (JSmol)

EC Number634-647-0

PubChem CID

CompTox Dashboard (EPA)

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,1-6H3Key: MZOPWQKISXCCTP-UHFFFAOYSA-NInChI=1/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,1-6H3Key: MZOPWQKISXCCTP-UHFFFAOYAY

SMILES CC(C)(C)c1cc(cc(c1O)C(C)(C)C)C=C(C#N)C#N

Properties

Chemical formulaC18H22N2O

Molar mass282.387 g·mol−1

Melting point142 °C (288 °F; 415 K) ±1°

Hazards

GHS labelling:

Pictograms

Signal wordDanger

Hazard statementsH301, H311, H331

Precautionary statementsP261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Malonoben (also known as tyrphostin A9, SF-6847, GCP5126, and AG-17) is an uncoupling agent/protonophore. As of 1974 when it was discovered, it was considered the most powerful agent of this type, with a potency over 1800 times that of 2,4-dinitrophenol - the prototypical uncoupling agent - and about 3 times the effectiveness of 5-chloro-3-tert-butyl-2'-chloro-4'-nitrosalicylanilide.