MedKoo Cat#: 464501 | Name: NSC 5302
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Description:

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

NSC 5302 is a synthetic coumarin with diverse biological activities. It scavenges alkylperoxy radicals and hypochlorous acid (HOCl; IC50 = 2.85 µM) in cell-free assays, as well as inhibits lipid peroxidation in rat liver microsomes, A23187-induced thromboxane B2 (TXB2) generation in isolated rat peritoneal leukocytes, and myeloperoxidase (MPO) activity in a cell-free assay (IC50s = 12, 1, and 1.06 µM, respectively). NSC 5302 also inhibits rat lens aldose reductase (IC50 = 17 µM) and human carbonic anhydrase I (CAI), CAIX, and CAXII with Ki values of 8.4, 0.19, and 6.4 µM, respectively. It inhibits platelet aggregation induced by arachidonic acid with an IC50 value of 45 µM. NSC 5302 inhibits hepatitis C virus (HCV) non-structural protein 5B (NS5B) polymerase (IC50 = 47.2 µM). It is active against H. pylori with an MIC value of 10 µg/ml.

Chemical Structure

NSC 5302
NSC 5302
CAS#2107-76-8

Theoretical Analysis

MedKoo Cat#: 464501

Name: NSC 5302

CAS#: 2107-76-8

Chemical Formula: C10H8O4

Exact Mass: 192.0423

Molecular Weight: 192.17

Elemental Analysis: C, 62.50; H, 4.20; O, 33.30

Price and Availability

Size Price Availability Quantity
250mg USD 350.00 2 Weeks
500mg USD 550.00 2 Weeks
1g USD 950.00 2 Weeks
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Related CAS #
No Data
Synonym
NSC 5302; NSC-5302; NSC5302; 5,7-Dihydroxy-4-methylcoumarin;
IUPAC/Chemical Name
5,7-dihydroxy-4-methyl-2H-chromen-2-one
InChi Key
QNVWGEJMXOQQPM-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H8O4/c1-5-2-9(13)14-8-4-6(11)3-7(12)10(5)8/h2-4,11-12H,1H3
SMILES Code
O=C1OC2=C(C(O)=CC(O)=C2)C(C)=C1
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
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
Product Data
Biological target:
5,7-Dihydroxy-4-methylcoumarin possesses antifungal and antibacterial activities.
In vitro activity:
This study evaluated the antioxidant and immunomodulator potential of five 4-methylcoumarin derivatives. Interestingly, the 5,7-dihydroxy-4-methylcoumarin scavenged hypochlorous acid more effectively than the o-dihydroxy-substituted 4-methylcoumarin derivatives, and the diacetoxylated 4-methylcoumarin derivatives scavenged hypochlorous acid as effectively as the 7,8-dihydroxy-4-methylcoumarin. Reference: J Med Food. 2013 Aug;16(8):692-700. https://pubmed.ncbi.nlm.nih.gov/23905650/
In vivo activity:
This work aimed to assess D4M's (NSC 5302) impact on cisplatin-induced ototoxicity. The results showed that D4M pretreatment protected hair cells from cisplatin-induced damage, increased cell viability, and decreased apoptosis in House Ear Institute-Organ of Corti1 (HEI-OC1) cells and neonatal mouse cochlear explants. D4M significantly inhibited cisplatin-induced mitochondrial apoptosis and reduced ROS accumulation. The protective effect of D4M on cisplatin-induced ototoxicity was also confirmed in cochlear hair cells and spiral ganglion neurons in neonatal mice. Reference: Biochim Biophys Acta Mol Cell Res. 2023 Apr;1870(4):119437. https://pubmed.ncbi.nlm.nih.gov/36754151/
Solvent mg/mL mM
Solubility
DMF 30.0 156.00
DMSO 30.0 156.00
DMSO:PBS (pH 7.2) (1:3) 0.3 1.30
Ethanol 20.0 104.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 192.17 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
Formulation protocol:
1. Kabeya LM, Fuzissaki CN, Andrade MF, Azzolini AE, Taleb-Contini SH, Vermelho RB, Lopes JL, Lucisano-Valim YM. 4-methylcoumarin derivatives inhibit human neutrophil oxidative metabolism and elastase activity. J Med Food. 2013 Aug;16(8):692-700. doi: 10.1089/jmf.2012.0184. Epub 2013 Aug 1. PMID: 23905650; PMCID: PMC3751208. 2. Li C, Wang X, Qiao X, Fan L, Zhu H, Chen Y, He Y, Zhang Z. 5,7-Dihydroxy-4-methylcoumarin modulates the JNK/FoxO1 signaling pathway to attenuate cisplatin-induced ototoxicity by suppressing oxidative stress and apoptosis in vitro. Biochim Biophys Acta Mol Cell Res. 2023 Apr;1870(4):119437. doi: 10.1016/j.bbamcr.2023.119437. Epub 2023 Feb 6. PMID: 36754151.
In vitro protocol:
1. Kabeya LM, Fuzissaki CN, Andrade MF, Azzolini AE, Taleb-Contini SH, Vermelho RB, Lopes JL, Lucisano-Valim YM. 4-methylcoumarin derivatives inhibit human neutrophil oxidative metabolism and elastase activity. J Med Food. 2013 Aug;16(8):692-700. doi: 10.1089/jmf.2012.0184. Epub 2013 Aug 1. PMID: 23905650; PMCID: PMC3751208.
In vivo protocol:
1. Li C, Wang X, Qiao X, Fan L, Zhu H, Chen Y, He Y, Zhang Z. 5,7-Dihydroxy-4-methylcoumarin modulates the JNK/FoxO1 signaling pathway to attenuate cisplatin-induced ototoxicity by suppressing oxidative stress and apoptosis in vitro. Biochim Biophys Acta Mol Cell Res. 2023 Apr;1870(4):119437. doi: 10.1016/j.bbamcr.2023.119437. Epub 2023 Feb 6. PMID: 36754151.
1: Kabeya LM, Fuzissaki CN, Andrade MF, Azzolini AE, Taleb-Contini SH, Vermelho RB, Lopes JL, Lucisano-Valim YM. 4-methylcoumarin derivatives inhibit human neutrophil oxidative metabolism and elastase activity. J Med Food. 2013 Aug;16(8):692-700. doi: 10.1089/jmf.2012.0184. Epub 2013 Aug 1. PMID: 23905650; PMCID: PMC3751208. 2: Macáková K, Řeháková Z, Mladěnka P, Karlíčková J, Filipský T, Říha M, Prasad AK, Parmar VS, Jahodář L, Pávek P, Hrdina R, Saso L. In vitro platelet antiaggregatory properties of 4-methylcoumarins. Biochimie. 2012 Dec;94(12):2681-6. doi: 10.1016/j.biochi.2012.09.006. Epub 2012 Sep 17. PMID: 22996069. 3: Xue B, Zhou L, Liu J, Yu R. Biotransformation of hydroxycoumarin derivatives by cultured suspension cells of Catharanthus roseus. Pharmazie. 2012 May;67(5):467-71. PMID: 22764584. 4: Kancheva VD, Saso L, Boranova PV, Khan A, Saroj MK, Pandey MK, Malhotra S, Nechev JZ, Sharma SK, Prasad AK, Georgieva MB, Joseph C, DePass AL, Rastogi RC, Parmar VS. Structure-activity relationship of dihydroxy-4-methylcoumarins as powerful antioxidants: correlation between experimental & theoretical data and synergistic effect. Biochimie. 2010 Sep;92(9):1089-100. doi: 10.1016/j.biochi.2010.06.012. Epub 2010 Jun 19. PMID: 20600568. 5: Esquivelzeta-Rabell M, Peon J, Cuevas G. Rotational diffusion of dihydroxy coumarins: Effect of OH groups and their relative position on solute-solvent interactions. J Phys Chem B. 2009 Jun 25;113(25):8599-606. doi: 10.1021/jp9010058. PMID: 19489576. 6: Céspedes CL, Avila JG, Martínez A, Serrato B, Calderón-Mugica JC, Salgado- Garciglia R. Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida). J Agric Food Chem. 2006 May 17;54(10):3521-7. doi: 10.1021/jf053071w. PMID: 19127719. 7: Sharma RK, Pande V, Ramos MJ, Rajor HK, Chopra S, Meguro K, Inoue J, Otsuka M. Inhibitory activity of polyhydroxycarboxylate chelators against recombinant NF-kappaB p50 protein-DNA binding. Bioorg Chem. 2005 Apr;33(2):67-81. doi: 10.1016/j.bioorg.2004.12.001. PMID: 15788163. 8: Kurosaki H, Sharma RK, Otsuka M, Goto M. Crystal structure of 7,8-dihydroxy-4-methylcoumarin. Anal Sci. 2003 Apr;19(4):647-8. doi: 10.2116/analsci.19.647. PMID: 12725413. 9: Hoult JR, Payá M. Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. Gen Pharmacol. 1996 Jun;27(4):713-22. doi: 10.1016/0306-3623(95)02112-4. PMID: 8853310. 10: Hoult JR, Forder RA, de las Heras B, Lobo IB, Payá M. Inhibitory activity of a series of coumarins on leukocyte eicosanoid generation. Agents Actions. 1994 Aug;42(1-2):44-9. doi: 10.1007/BF02014299. PMID: 7847183. 11: Payá M, Halliwell B, Hoult JR. Interactions of a series of coumarins with reactive oxygen species. Scavenging of superoxide, hypochlorous acid and hydroxyl radicals. Biochem Pharmacol. 1992 Jul 22;44(2):205-14. doi: 10.1016/0006-2952(92)90002-z. PMID: 1322662. 12: Hausen BM, Berger M. The sensitizing capacity of coumarins (III). Contact Dermatitis. 1989 Sep;21(3):141-7. doi: 10.1111/j.1600-0536.1989.tb04726.x. PMID: 2529098.