Malonoben

Malonoben
Names
	IUPAC name [4-Hydroxy-3,5-bis(2-methyl-2-propanyl)benzylidene]malononitrile
Identifiers
CAS Number	10537-47-0;
3D model (JSmol)	Interactive image;
ChemSpider	5412;
ECHA InfoCard	100.162.608
PubChem CID	5614;
CompTox Dashboard (EPA)	DTXSID1042106 ;
	InChI InChI=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 Key: MZOPWQKISXCCTP-UHFFFAOYSA-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 Key: MZOPWQKISXCCTP-UHFFFAOYAY;
	SMILES CC(C)(C)c1cc(cc(c1O)C(C)(C)C)C=C(C#N)C#N;
Properties
Chemical formula	C18H22N2O
Molar mass	282.380
	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 a uncoupling agent/protonophore.^[1]^[2] As of 1974 when it was discovered, its 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. National Center for Biotechnology Information, U.S. National Library of Medicine. pp. 193–199. doi:10.1016/0005-2728(88)90070-9. PMID 2894856. Retrieved 2020-01-23.
^ 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. National Center for Biotechnology Information, U.S. National Library of Medicine. pp. 507–518. doi:10.1016/0005-2728(75)90089-4. PMID 1138887. Retrieved 2020-01-23.
^ Terada, H. (November 7, 1974). "SOME BIOCHEMICAL AND PHYSICOCHEMICAL PROPERTIES OF THE POTENT UNCOUPLER SF-6847 (3,5-DI-TERT-BUTYL-4-HYDROXYBENZYLIDENEMALONONITRILE)" (PDF). Biochimica et Biophysica Acta (Bba) - Bioenergetics. 387 (3): 519–532. doi:10.1016/0005-2728(75)90090-0. Retrieved February 8, 2019. {{cite journal}}: Cite has empty unknown parameter: |dead-url= (help)

Category:Ionophores Category:Uncoupling agents Category:Nitriles

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[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. National Center for Biotechnology Information, U.S. National Library of Medicine. pp. 193–199. doi:10.1016/0005-2728(88)90070-9. PMID 2894856. Retrieved 2020-01-23.

[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. National Center for Biotechnology Information, U.S. National Library of Medicine. pp. 507–518. doi:10.1016/0005-2728(75)90089-4. PMID 1138887. Retrieved 2020-01-23.

[3] Terada, H. (November 7, 1974). "SOME BIOCHEMICAL AND PHYSICOCHEMICAL PROPERTIES OF THE POTENT UNCOUPLER SF-6847 (3,5-DI-TERT-BUTYL-4-HYDROXYBENZYLIDENEMALONONITRILE)" (PDF). Biochimica et Biophysica Acta (Bba) - Bioenergetics. 387 (3): 519–532. doi:10.1016/0005-2728(75)90090-0. Retrieved February 8, 2019. {{cite journal}}: Cite has empty unknown parameter: |dead-url= (help)

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