Chemistry:SF-6847
From HandWiki
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| Names | |
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| Preferred IUPAC name
[(3,5-di-tert-Butyl-4-hydroxyphenyl)methylidene]propanedinitrile | |
| Other names
Malonoben
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3D model (JSmol)
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| Properties | |
| C18H22N2O | |
| Molar mass | 282.380 |
| Melting point | 142 °C (288 °F; 415 K) ±1° |
| Hazards | |
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| GHS Signal word | Danger |
| H301, H311, H331 | |
| P261, P264, P270, P271, P280, P301+310, P302+352, P304+340, P311, P312, P321, P322, P330, P361, P363, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
SF-6847 (aka Malonoben, Tyrphostin A9, GCP5126, and AG-17) is an uncoupling agent/protonophore.[1][2] As of 1974 when it was discovered, it was considered most powerful, with a potency over 1800x that of 2,4-dinitrophenol - the prototypical uncoupling agent, and about 3x the effectiveness of 5-chloro-3-tert-butyl-2'-chloro-4'-nitrosalicylanilide.[3]
References
- ↑ 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.
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