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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