Chemistry:SF-6847

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SF-6847
SF-6847 Structure.svg
Names
Preferred IUPAC name
[(3,5-di-tert-Butyl-4-hydroxyphenyl)methylidene]propanedinitrile
Other names
Malonoben
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 634-647-0
KEGG
UNII
Properties
C18H22N2O
Molar mass 282.380
Melting point 142 °C (288 °F; 415 K) ±1°
Hazards
GHS pictograms GHS06: Toxic
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

  1. 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. 
  2. 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. 
  3. 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.