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)}}
References
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