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MedKoo Cat#: 145406 | Name: Diapocynin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Diapocynin is a NADPH oxidase inhibitor. Diapocynin significantly rescues DFP-induced motor impairment and attenuated epileptiform. Diapocynin shows higher antioxidant capacity than apocynin. Diapocynin induces hypotensive and vasodilator effects in rats.

Chemical Structure

Diapocynin
CAS#29799-22-2

Theoretical Analysis

MedKoo Cat#: 145406

Name: Diapocynin

CAS#: 29799-22-2

Chemical Formula: C18H18O6

Exact Mass: 330.1103

Molecular Weight: 330.34

Elemental Analysis: C, 65.45; H, 5.49; O, 29.06

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Diapocynin; Dehydrodiacetovanillone;
IUPAC/Chemical Name
1,1'-(6,6'-dihydroxy-5,5'-dimethoxy-[1,1'-biphenyl]-3,3'-diyl)bis(ethan-1-one)
InChi Key
HLNDPICGHQGWSU-UHFFFAOYSA-N
InChi Code
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
SMILES Code
COC1=CC(=CC(=C1O)C2=C(O)C(OC)=CC(=C2)C(C)=O)C(C)=O
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 330.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Ibrahim WW, Abdel Rasheed NO. Diapocynin neuroprotective effects in 3-nitropropionic acid Huntington's disease model in rats: emphasis on Sirt1/Nrf2 signaling pathway. Inflammopharmacology. 2022 Oct;30(5):1745-1758. doi: 10.1007/s10787-022-01004-z. Epub 2022 May 31. PMID: 35639233; PMCID: PMC9499906. 2: Putra M, Gage M, Sharma S, Gardner C, Gasser G, Anantharam V, Thippeswamy T. Diapocynin, an NADPH oxidase inhibitor, counteracts diisopropylfluorophosphate- induced long-term neurotoxicity in the rat model. Ann N Y Acad Sci. 2020 Nov;1479(1):75-93. doi: 10.1111/nyas.14314. Epub 2020 Feb 10. PMID: 32037612; PMCID: PMC7415478. 3: Potje SR, Troiano JA, Graton ME, Ximenes VF, Nakamune ACMS, Antoniali C. Hypotensive and vasorelaxant effect of Diapocynin in normotensive rats. Free Radic Biol Med. 2017 May;106:148-157. doi: 10.1016/j.freeradbiomed.2017.02.026. Epub 2017 Feb 10. PMID: 28192231. 4: Ibrahim WW, Ismail HM, Khattab MM, Abdelkader NF. Cognitive enhancing effect of diapocynin in D-galactose-ovariectomy-induced Alzheimer's-like disease in rats: Role of ERK, GSK-3β, and JNK signaling. Toxicol Appl Pharmacol. 2020 Jul 1;398:115028. doi: 10.1016/j.taap.2020.115028. Epub 2020 Apr 29. PMID: 32360636. 5: Trumbull KA, McAllister D, Gandelman MM, Fung WY, Lew T, Brennan L, Lopez N, Morré J, Kalyanaraman B, Beckman JS. Diapocynin and apocynin administration fails to significantly extend survival in G93A SOD1 ALS mice. Neurobiol Dis. 2012 Jan;45(1):137-44. doi: 10.1016/j.nbd.2011.07.015. Epub 2011 Jul 28. PMID: 21820513; PMCID: PMC3710723. 6: Guedira G, Petermann O, Scapozza L, Ismail HM. Diapocynin treatment induces functional and structural improvements in an advanced disease state in the mdx5Cv mice. Biomed Pharmacother. 2024 Jun 21;177:116957. doi: 10.1016/j.biopha.2024.116957. Epub ahead of print. PMID: 38908198. 7: Kanegae MP, Condino-Neto A, Pedroza LA, de Almeida AC, Rehder J, da Fonseca LM, Ximenes VF. Diapocynin versus apocynin as pretranscriptional inhibitors of NADPH oxidase and cytokine production by peripheral blood mononuclear cells. Biochem Biophys Res Commun. 2010 Mar 12;393(3):551-4. doi: 10.1016/j.bbrc.2010.02.073. Epub 2010 Feb 18. PMID: 20171179. 8: Ismail HM, Scapozza L, Ruegg UT, Dorchies OM. Diapocynin, a dimer of the NADPH oxidase inhibitor apocynin, reduces ROS production and prevents force loss in eccentrically contracting dystrophic muscle. PLoS One. 2014 Oct 17;9(10):e110708. doi: 10.1371/journal.pone.0110708. PMID: 25329652; PMCID: PMC4201587. 9: Wang Q, Smith RE, Luchtefeld R, Sun AY, Simonyi A, Luo R, Sun GY. Bioavailability of apocynin through its conversion to glycoconjugate but not to diapocynin. Phytomedicine. 2008 Jun;15(6-7):496-503. doi: 10.1016/j.phymed.2007.09.019. Epub 2007 Oct 30. PMID: 17977702; PMCID: PMC2527211. 10: Dranka BP, Gifford A, Ghosh A, Zielonka J, Joseph J, Kanthasamy AG, Kalyanaraman B. Diapocynin prevents early Parkinson's disease symptoms in the leucine-rich repeat kinase 2 (LRRK2R¹⁴⁴¹G) transgenic mouse. Neurosci Lett. 2013 Aug 9;549:57-62. doi: 10.1016/j.neulet.2013.05.034. Epub 2013 May 28. PMID: 23721786; PMCID: PMC3729885. 11: Luchtefeld R, Luo R, Stine K, Alt ML, Chernovitz PA, Smith RE. Dose formulation and analysis of diapocynin. J Agric Food Chem. 2008 Jan 23;56(2):301-6. doi: 10.1021/jf072792n. Epub 2007 Dec 20. PMID: 18092754. 12: Macías Pérez ME, Hernández Rodríguez M, Cabrera Pérez LC, Fragoso-Vázquez MJ, Correa-Basurto J, Padilla-Martínez II, Méndez Luna D, Mera Jiménez E, Flores Sandoval C, Tamay Cach F, Rosales-Hernández MC. Aromatic Regions Govern the Recognition of NADPH Oxidase Inhibitors as Diapocynin and its Analogues. Arch Pharm (Weinheim). 2017 Oct;350(10). doi: 10.1002/ardp.201700041. Epub 2017 Aug 21. PMID: 28833480. 13: Marín M, Gimeno C, Giner RM, Ríos JL, Máñez S, Recio MAC. Influence of Dimerization of Apocynin on Its Effects in Experimental Colitis. J Agric Food Chem. 2017 May 24;65(20):4083-4091. doi: 10.1021/acs.jafc.7b00872. Epub 2017 May 16. PMID: 28485605. 14: Ghosh A, Kanthasamy A, Joseph J, Anantharam V, Srivastava P, Dranka BP, Kalyanaraman B, Kanthasamy AG. Anti-inflammatory and neuroprotective effects of an orally active apocynin derivative in pre-clinical models of Parkinson's disease. J Neuroinflammation. 2012 Oct 23;9:241. doi: 10.1186/1742-2094-9-241. PMID: 23092448; PMCID: PMC3488558. 15: Silva D, Sousa AC, Robalo MP, Martins LO. A wide array of lignin-related phenolics are oxidized by an evolved bacterial dye-decolourising peroxidase. N Biotechnol. 2023 Nov 25;77:176-184. doi: 10.1016/j.nbt.2022.12.003. Epub 2022 Dec 20. PMID: 36563877. 16: Yamazoe H. Multifunctional Micromachines Constructed by Combining Multiple Protein-Based Components with Different Functions. ACS Appl Mater Interfaces. 2023 Dec 27;15(51):59145-59154. doi: 10.1021/acsami.3c12912. Epub 2023 Dec 11. PMID: 38078429. 17: Graton ME, Potje SR, Troiano JA, Vale GT, Perassa LA, Nakamune ACMS, Tirapelli CR, Bendhack LM, Antoniali C. Apocynin alters redox signaling in conductance and resistance vessels of spontaneously hypertensive rats. Free Radic Biol Med. 2019 Apr;134:53-63. doi: 10.1016/j.freeradbiomed.2018.12.026. Epub 2018 Dec 23. PMID: 30586635. 18: Yamazoe H. Multifunctional protein microparticles for medical applications. Biomaterials. 2018 Feb;155:1-12. doi: 10.1016/j.biomaterials.2017.10.045. Epub 2017 Oct 31. PMID: 29154040. 19: Abraham MH, Smith RE, Luchtefeld R, Boorem AJ, Luo R, Acree WE Jr. Prediction of solubility of drugs and other compounds in organic solvents. J Pharm Sci. 2010 Mar;99(3):1500-15. doi: 10.1002/jps.21922. PMID: 19774653. 20: Liu F, Fan LM, Michael N, Li JM. In vivo and in silico characterization of apocynin in reducing organ oxidative stress: A pharmacokinetic and pharmacodynamic study. Pharmacol Res Perspect. 2020 Aug;8(4):e00635. doi: 10.1002/prp2.635. PMID: 32761799; PMCID: PMC7406636.