Diapocynin

Diapocynin

Names
IUPAC name 1,1′-(6,6′-Dihydroxy-5,5′-dimethoxy[1,1′-biphenyl]-3,3′-diyl)bis-ethanone
Other names Diapocynin, 4',4-Dihydroxy-5',5-dimethoxy-3',3-biacetophenone
Identifiers
CAS Number	29799-22-2
3D model (Jmol)	Interactive image
ChemSpider	8103122
ECHA InfoCard	100.233.239
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	330.34 g·mol^−1
Appearance	brown color
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

1. "Synthesis of diapocynin." Journal of chemical education 85, no. 3 (2008): 411.
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.
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. doi:10.1371/journal.pone.0110708.