Malonoben

{{Chembox

| ImageFile = SF-6847 Structure.svg

| ImageSize =

| PIN = [(3,5-di-tert-Butyl-4-hydroxyphenyl)methylidene]propanedinitrile

| OtherNames = Tyrphostin A9; SF-6847; GCP5126; and AG-17

| Section1 = {{Chembox Identifiers

| CASNo = 10537-47-0

| PubChem = 5614

| ChemSpiderID = 5412

| UNII = 87TE8MRS65

| ChEMBL = 78150

| ChEBI = 82168

| KEGG = C19039

| EINECS = 634-647-0

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

| InChI = 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,1-6H3

| InChIKey = MZOPWQKISXCCTP-UHFFFAOYAY

| StdInChI = 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

| StdInChIKey = MZOPWQKISXCCTP-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

| C=18 | H = 22 | N = 2 | O = 1

| Appearance =

| Density =

| MeltingPtC = 142

| MeltingPt_notes=±1°

| BoilingPt =

| Solubility =

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| GHSPictograms = {{GHS06}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|301|311|331}}

| PPhrases = {{P-phrases|261|264|270|271|280|301+310|302+352|304+340|311|312|321|322|330|361|363|403+233|405|501}}

}}

}}

Malonoben (also known as tyrphostin A9, SF-6847, GCP5126, and AG-17) is an uncoupling agent/protonophore.{{Cite journal |title=Unique action of a modified weakly acidic uncoupler without an acidic group, methylated SF 6847, as an inhibitor of oxidative phosphorylation with no uncoupling activity: possible identity of uncoupler binding protein |journal = Biochimica et Biophysica Acta (BBA) - Bioenergetics|volume = 933|issue = 1|last1=Terada |first1=H. |last2=Fukui |first2=Y. |date=1988-03-30 |pages=193–199 |doi=10.1016/0005-2728(88)90070-9 |pmid=2894856 |last3=Shinohara |first3=Y. |last4=Ju-ichi |first4=M.}}{{Cite journal |title=On the stoichiometry between uncouplers of oxidative phosphorylation and respiratory chains. The catalytic action of SF 6847 (3,5-di-tert-butyl-4-hydroxy-benzylidenemalononitrile) |journal = Biochimica et Biophysica Acta (BBA) - Bioenergetics|volume = 387|issue = 3|last1=Terada |first1=H. |last2=VAN Dam |first2=K. |date=1975-06-17 |pages=507–518 |doi=10.1016/0005-2728(75)90089-4 |pmid=1138887 }} 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.{{Cite journal|last=Terada|first=H.|date=November 7, 1974|journal=Biochimica et Biophysica Acta (BBA) - Bioenergetics|volume=387|issue=3|pages=519–532|doi=10.1016/0005-2728(75)90090-0|pmid=237542|title=Some biochemical and physicochemical properties of the potent uncoupler SF 6847 (3,5-di-tert-butyl-4-hydroxybenzylidenemalononitrile)}}