Diapocynin

Diapocynin
Names
	Preferred IUPAC name 1,1′-(6,6′-Dihydroxy-5,5′-dimethoxy[1,1′-biphenyl]-3,3′-diyl)di(ethan-1-one)
	Other names Diapocynin, 4′,4′′′-Dihydroxy-5′,5′′′-dimethoxy-3′,3′′′-biacetophenone
Identifiers
CAS Number	29799-22-2;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL38775;
ChemSpider	8103122;
ECHA InfoCard	100.233.239
PubChem CID	9927489;
UNII	A65KM2ZD49 ;
CompTox Dashboard (EPA)	DTXSID701032857 ;
	InChI InChI=1S/C18H18O6/c1-9(19)11-5-13(17(21)15(7-11)23-3)14-6-12(10(2)20)8-16(24-4)18(14)22/h5-8,21-22H,1-4H3 Key: HLNDPICGHQGWSU-UHFFFAOYSA-N; InChI=1/C18H18O6/c1-9(19)11-5-13(17(21)15(7-11)23-3)14-6-12(10(2)20)8-16(24-4)18(14)22/h5-8,21-22H,1-4H3 Key: HLNDPICGHQGWSU-UHFFFAOYAP;
	SMILES CC(=O)C1=CC(=C(C(=C1)OC)O)C2=C(C(=CC(=C2)C(=O)C)OC)O;
Properties
Chemical formula	C18H18O6
Molar mass	330.336 g·mol−1
Appearance	brown color
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H410
Precautionary statements	P273, P391, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diapocynin is a dimer of apocynin.

Synthesis

Diapocynin is synthesized by the activation of apocynin with ferrous sulfate and sodium persulfate. Similar to apocynin, it is shown to have some beneficial effects against oxidative stress and reducing reactive oxygen species.

References

↑ Luchtefeld, Ron (2008). "Synthesis of diapocynin". Journal of Chemical Education. 85 (3): 411. Bibcode:2008JChEd..85..411L. doi:10.1021/ed085p411.
↑ Dranka, B. P.; Gifford, A.; Ghosh, A.; Zielonka, J.; Joseph, J.; Kanthasamy, A. G.; Kalyanaraman, B. (2013). "Diapocynin prevents early Parkinson's disease symptoms in the leucine-rich repeat kinase 2 (LRRK2 R1441G) transgenic mouse". Neuroscience Letters. 549: 57–62. doi:10.1016/j.neulet.2013.05.034. PMC 3729885. PMID 23721786.
↑ Ismail, Hesham M.; Scapozza, Leonardo; Ruegg, Urs T.; Dorchies, Olivier M. (17 October 2014). "Diapocynin, a Dimer of the NADPH Oxidase Inhibitor Apocynin, Reduces ROS Production and Prevents Force Loss in Eccentrically Contracting Dystrophic Muscle". PLOS ONE. 9 (10) e110708. Bibcode:2014PLoSO...9k0708I. doi:10.1371/journal.pone.0110708. PMC 4201587. PMID 25329652.

[1] Luchtefeld, Ron (2008). "Synthesis of diapocynin". Journal of Chemical Education. 85 (3): 411. Bibcode:2008JChEd..85..411L. doi:10.1021/ed085p411.

[2] Dranka, B. P.; Gifford, A.; Ghosh, A.; Zielonka, J.; Joseph, J.; Kanthasamy, A. G.; Kalyanaraman, B. (2013). "Diapocynin prevents early Parkinson's disease symptoms in the leucine-rich repeat kinase 2 (LRRK2 R1441G) transgenic mouse". Neuroscience Letters. 549: 57–62. doi:10.1016/j.neulet.2013.05.034. PMC 3729885. PMID 23721786.

[3] Ismail, Hesham M.; Scapozza, Leonardo; Ruegg, Urs T.; Dorchies, Olivier M. (17 October 2014). "Diapocynin, a Dimer of the NADPH Oxidase Inhibitor Apocynin, Reduces ROS Production and Prevents Force Loss in Eccentrically Contracting Dystrophic Muscle". PLOS ONE. 9 (10) e110708. Bibcode:2014PLoSO...9k0708I. doi:10.1371/journal.pone.0110708. PMC 4201587. PMID 25329652.