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.^[1] Similar to apocynin, it is shown to have some beneficial effects against oxidative stress and reducing reactive oxygen species.^[2]^[3]

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.

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Synthesis

References