Malonoben

Malonoben
Names
	Preferred IUPAC name [(3,5-di-tert-Butyl-4-hydroxyphenyl)methylidene]propanedinitrile
	Other names Tyrphostin A9; SF-6847; GCP5126; and AG-17
Identifiers
CAS Number	10537-47-0;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:82168;
ChEMBL	ChEMBL78150;
ChemSpider	5412;
ECHA InfoCard	100.162.608
EC Number	634-647-0;
KEGG	C19039;
PubChem CID	5614;
UNII	87TE8MRS65;
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	282.387 g·mol−1
Melting point	142 °C (288 °F; 415 K) ±1°
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H331
Precautionary statements	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). Infobox references

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

^ 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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[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.

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