Malonoben
Appearance
Names | |
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Preferred IUPAC name
[(3,5-di-tert-Butyl-4-hydroxyphenyl)methylidene]propanedinitrile | |
Other names
Tyrphostin A9; SF-6847; GCP5126; and AG-17
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.162.608 |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C18H22N2O | |
Molar mass | 282.387 g·mol−1 |
Melting point | 142 °C (288 °F; 415 K) ±1° |
Hazards | |
GHS labelling: | |
Danger | |
H301, H311, H331 | |
P261, 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).
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Malonoben (also known as tyrphostin A9, SF-6847, GCP5126, and AG-17) is an uncoupling agent/protonophore.[1][2] 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.[3]
References
[edit]- ^ Terada, H.; Fukui, Y.; Shinohara, Y.; Ju-ichi, M. (1988-03-30). "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". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 933 (1): 193–199. doi:10.1016/0005-2728(88)90070-9. PMID 2894856.
- ^ Terada, H.; VAN Dam, K. (1975-06-17). "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)". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 387 (3): 507–518. doi:10.1016/0005-2728(75)90089-4. PMID 1138887.
- ^ Terada, H. (November 7, 1974). "Some biochemical and physicochemical properties of the potent uncoupler SF 6847 (3,5-di-tert-butyl-4-hydroxybenzylidenemalononitrile)". Biochimica et Biophysica Acta (BBA) - Bioenergetics. 387 (3): 519–532. doi:10.1016/0005-2728(75)90090-0. PMID 237542.