Dunnione | CAS#33404-57-8 | antifungal

MedKoo Cat#: 561251 | Name: Dunnione

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Description:

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

Dunnione is a synthetic 1,4-naphthoquinone derivative known for its ability to modulate cellular redox states and NAD⁺ metabolism. It acts as a substrate for NAD(P)H:quinone oxidoreductase 1 (NQO1), leading to NAD⁺ generation and potential protection against oxidative stress. Dunnione has been investigated for its therapeutic potential in models of metabolic disorders, neurodegeneration, and age-related diseases due to its role in enhancing cellular NAD⁺ levels and mitochondrial function.

Chemical Structure

Dunnione

CAS#33404-57-8

Theoretical Analysis

MedKoo Cat#: 561251

Name: Dunnione

CAS#: 33404-57-8

Chemical Formula: C15H14O3

Exact Mass: 242.0943

Molecular Weight: 242.27

Elemental Analysis: C, 74.36; H, 5.82; O, 19.81

Price and Availability

Size	Price	Availability
5mg	USD 350.00	2 Weeks
10mg	USD 650.00	2 Weeks
25mg	USD 1,250.00	2 Weeks

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Related CAS #

No Data

Synonym

Dunnione; DL-Dunnione; (+/-)-Dunnione; NSC-95403; NSC95403; NSC 95403;

IUPAC/Chemical Name

2,3-Dihydro-2,3,3-trimethylnaphtho(1,2-b)furan-4,5-dione; 2,3,3-trimethyl-2H-benzo[g][1]benzofuran-4,5-dione

InChi Key

WGENOABUKBFVAA-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H14O3/c1-8-15(2,3)11-13(17)12(16)9-6-4-5-7-10(9)14(11)18-8/h4-8H,1-3H3

SMILES Code

O=C1C2=C(OC(C)C2(C)C)C3=CC=CC=C3C1=O

Appearance

Solid powder

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

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 242.27 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.

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: Bian J, Xu L, Deng B, Qian X, Fan J, Yang X, Liu F, Xu X, Guo X, Li X, Sun H, You Q, Zhang X. Synthesis and evaluation of (±)-dunnione and its ortho-quinone analogues as substrates for NAD(P)H:quinone oxidoreductase 1 (NQO1). Bioorg Med Chem Lett. 2015 Mar 15;25(6):1244-8. doi: 10.1016/j.bmcl.2015.01.057. Epub 2015 Jan 31. PubMed PMID: 25677663. 2: Park D, Jo IG, Jang JY, Kwak TH, Yoo SK, Jeon JH, Choi EK, Joo SS, Kim O, Kim YB. A Dunnione Compound MB12662 Improves Cisplatin-Induced Tissue Injury and Emesis. Biomol Ther (Seoul). 2015 Sep;23(5):449-57. doi: 10.4062/biomolther.2015.034. Epub 2015 Sep 1. PubMed PMID: 26336585; PubMed Central PMCID: PMC4556205. 3: Jo IG, Park D, Kyung J, Kim D, Cai J, Kim J, Kwak TH, Yoo SK, Jeong HS, Kim YB. Inhibitory effects of a β-dunnione compound MB12662 on gastric secretion and ulcers. Lab Anim Res. 2013 Sep;29(3):178-81. doi: 10.5625/lar.2013.29.3.178. Epub 2013 Sep 27. PubMed PMID: 24106514; PubMed Central PMCID: PMC3791353. 4: Pandit A, Kim HJ, Oh GS, Shen A, Lee SB, Khadka D, Lee S, Shim H, Yang SH, Cho EY, Kwon KB, Kwak TH, Choe SK, Park R, So HS. Dunnione ameliorates cisplatin-induced small intestinal damage by modulating NAD(+) metabolism. Biochem Biophys Res Commun. 2015 Nov 27;467(4):697-703. doi: 10.1016/j.bbrc.2015.10.081. Epub 2015 Oct 21. PubMed PMID: 26498527. 5: Kim HJ, Pandit A, Oh GS, Shen A, Lee SB, Khadka D, Lee S, Shim H, Yang SH, Cho EY, Kwak TH, Choe SK, Park R, So HS. Dunnione ameliorates cisplatin ototoxicity through modulation of NAD(+) metabolism. Hear Res. 2016 Mar;333:235-246. doi: 10.1016/j.heares.2015.08.017. Epub 2015 Sep 1. PubMed PMID: 26341473. 6: Inagaki R, Ninomiya M, Tanaka K, Koketsu M. Synthesis, Characterization, and Antileukemic Properties of Naphthoquinone Derivatives of Lawsone. ChemMedChem. 2015 Aug;10(8):1413-23. doi: 10.1002/cmdc.201500189. Epub 2015 Jun 18. PubMed PMID: 26088596. 7: Scharf DR, Verdan MH, Ribeiro MA, Simionatto EL, Sá EL, Salvador MJ, Barison A, Stefanello ME. Naphthochromenes and Related Constituents from the Tubers of Sinningia allagophylla. J Nat Prod. 2016 Apr 22;79(4):792-8. doi: 10.1021/acs.jnatprod.5b00799. Epub 2016 Apr 4. PubMed PMID: 27043314. 8: Verdan MH, Koolen HH, Salvador MJ, Barison A, Stefanello ME. A new naphthoquinone from Sinningia leucotricha (Gesneriaceae). Nat Prod Commun. 2015 Apr;10(4):625-6. PubMed PMID: 25973493. 9: Verdan MH, Ehrenfried CA, Scharf DR, Cervi AC, Salvadore MJ, Barison A, Stefanello EA. Chemical Constituents from Sinningia canescens and S. warmingii. Nat Prod Commun. 2014 Oct;9(10):1535-7. PubMed PMID: 25522555. 10: Sheridan H, Nestor C, O'Driscoll L, Hook I. Isolation, structure elucidation, and cytotoxic evaluation of furanonaphthoquinones from in vitro plantlets and cultures of Streptocarpus dunnii. J Nat Prod. 2011 Jan 28;74(1):82-5. doi: 10.1021/np100358a. Epub 2010 Dec 21. PubMed PMID: 21174407. 11: Khambay BP, Batty D, Jewess PJ, Bateman GL, Hollomon DW. Mode of action and pesticidal activity of the natural product dunnione and of some analogues. Pest Manag Sci. 2003 Feb;59(2):174-82. PubMed PMID: 12587871. 12: Céspedes CL, Salazar JR, Ariza-Castolo A, Yamaguchi L, Avila JG, Aqueveque P, Kubo I, Alarcón J. Biopesticides from plants: Calceolaria integrifolia s.l. Environ Res. 2014 Jul;132:391-406. doi: 10.1016/j.envres.2014.04.003. Epub 2014 Jun 2. PubMed PMID: 24893349. 13: Cai XH, Luo XD, Zhou J, Hao XJ. Quinones from Chirita eburnea. J Nat Prod. 2005 May;68(5):797-9. PubMed PMID: 15921435. 14: Muñoz E, Avila JG, Alarcón J, Kubo I, Werner E, Céspedes CL. Tyrosinase inhibitors from Calceolaria integrifolia s.l.: Calceolaria talcana aerial parts. J Agric Food Chem. 2013 May 8;61(18):4336-43. doi: 10.1021/jf400531h. Epub 2013 Apr 30. PubMed PMID: 23607420. 15: Cespedes CL, Muñoz E, Salazar JR, Yamaguchi L, Werner E, Alarcon J, Kubo I. Inhibition of cholinesterase activity by extracts, fractions and compounds from Calceolaria talcana and C. integrifolia (Calceolariaceae: Scrophulariaceae). Food Chem Toxicol. 2013 Dec;62:919-26. PubMed PMID: 24416779. 16: Cespedes CL, Muñoz E, Salazar JR, Yamaguchi L, Werner E, Alarcon J, Kubo I. Inhibition of cholinesterase activity by extracts, fractions and compounds from Calceolaria talcana and C. integrifolia (Calceolariaceae: Scrophulariaceae). Food Chem Toxicol. 2013 Oct 25. pii: S0278-6915(13)00702-3. doi: 10.1016/j.fct.2013.10.027. [Epub ahead of print] PubMed PMID: 24513062. 17: Piovano M, Garbarino J, Tomassini L, Nicoletti M. Cyclohexanones from Mimulus glabratus and M. luteus. Nat Prod Commun. 2009 Dec;4(12):1637-8. PubMed PMID: 20120096. 18: Wang MY, Gong MX, Zhang D, Yang L. A new beta-naphthalenecarboxylic acid biglycoside from Chirita longgangensis var. hongyao. Yao Xue Xue Bao. 2011 Feb;46(2):179-82. PubMed PMID: 21539150. 19: Dolan ME, Frydman B, Thompson CB, Diamond AM, Garbiras BJ, Safa AR, Beck WT, Marton LJ. Effects of 1,2-naphthoquinones on human tumor cell growth and lack of cross-resistance with other anticancer agents. Anticancer Drugs. 1998 Jun;9(5):437-48. PubMed PMID: 9660542. 20: Planchon SM, Wuerzberger-Davis SM, Pink JJ, Robertson KA, Bornmann WG, Boothman DA. Bcl-2 protects against beta-lapachone-mediated caspase 3 activation and apoptosis in human myeloid leukemia (HL-60) cells. Oncol Rep. 1999 May-Jun;6(3):485-92. PubMed PMID: 10203579.