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MedKoo Cat#: 464808 | Name: Visnagin
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Description:

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

Visnagin is a polyketide synthase-derived furanochromone originally isolated from A. visnaga that has diverse biological activities. It inhibits the germination and growth of ryegrass (IC50s = 502 and 214 µM, respectively). Visnagin (100 µg/ml) is cytotoxic to, and induces apoptosis in, HT-144 melanoma cells. It reduces LPS-stimulated increases in the secretion of TNF-α, IL-1β, and IFN-γ in BV-2 microglial cells when used at concentrations of 50 and 100 µM.4 Visnagin (25 mg/kg) protects against cardiomyopathy induced by doxorubicin in mice.

Chemical Structure

Visnagin
Visnagin
CAS#82-57-5

Theoretical Analysis

MedKoo Cat#: 464808

Name: Visnagin

CAS#: 82-57-5

Chemical Formula: C13H10O4

Exact Mass: 230.0579

Molecular Weight: 230.22

Elemental Analysis: C, 67.82; H, 4.38; O, 27.80

Price and Availability

Size Price Availability Quantity
100mg USD 400.00 2 Weeks
1g USD 650.00 2 Weeks
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Related CAS #
No Data
Synonym
Visnagin; NSC 100593; NSC 100593; NSC 100593;
IUPAC/Chemical Name
4-methoxy-7-methyl-5H-furo[3,2-g]chromen-5-one
InChi Key
NZVQLVGOZRELTG-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H10O4/c1-7-5-9(14)12-11(17-7)6-10-8(3-4-16-10)13(12)15-2/h3-6H,1-2H3
SMILES Code
O=C1C=C(OC2=C1C(OC)=C3C=COC3=C2)C
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
Solvent mg/mL mM
Solubility
DMF 10.0 43.44
DMF:PBS (pH 7.2) (1:5) 0.2 0.69
DMSO 5.0 21.72
Ethanol 1.0 4.34
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 230.22 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: Selim AAMA, Ibrahim MA. Natural benzofuran derivatives as promising scaffold for alleviating Alzheimer symptoms: acetylcholinesterase inhibition, structure activity relationship and in silico studies. Nat Prod Res. 2024 Nov 21:1-7. doi: 10.1080/14786419.2024.2431998. Epub ahead of print. PMID: 39570122. 2: Wan X, Yang C, Qiu S, Xu W, Lian J, Zhang J, Xing W, Yuan Y. Natural volatile organic compounds (NVOCs) and airborne microorganisms in different stands of urban forests. Sci Total Environ. 2024 Dec 10;955:176964. doi: 10.1016/j.scitotenv.2024.176964. Epub 2024 Oct 16. PMID: 39423900. 3: Khamis AA, Sharshar AH, Mohamed TM, Abdelrasoul EA, Salem MM. Visnagin alleviates rheumatoid arthritis via its potential inhibitory impact on malate dehydrogenase enzyme: in silico, in vitro, and in vivo studies. Genes Nutr. 2024 Oct 10;19(1):20. doi: 10.1186/s12263-024-00756-3. PMID: 39390383; PMCID: PMC11465529. 4: Palvia AR, Damera AR, Nandi AR, Magar S, Patidar S, Kasarla S, Ghantasala V, Shah MK, Goyal M. Cardio-Oncology's Modern Approaches to Prevent Doxorubicin- Induced Cardiotoxicity: A Systematic Review. Cureus. 2024 Aug 5;16(8):e66215. doi: 10.7759/cureus.66215. PMID: 39238705; PMCID: PMC11375109. 5: Abo-Salem HM, Ali EA, Abdelmegeed H, El Souda SSM, Abdel-Aziz MS, Ahmed KM, Fawzy NM. Chitosan nanoparticles of new chromone-based sulfonamide derivatives as effective anti-microbial matrix for wound healing acceleration. Int J Biol Macromol. 2024 Jun;272(Pt 1):132631. doi: 10.1016/j.ijbiomac.2024.132631. Epub 2024 May 27. PMID: 38810852. 6: Obeidat O, Obeidat A, Obeidat A, Ismail MF. Visnagin: A novel cardioprotective agent against anthracycline toxicity (Review). Med Int (Lond). 2024 May 13;4(4):37. doi: 10.3892/mi.2024.161. PMID: 38799005; PMCID: PMC11117031. 7: Yadav P, Singh SK, Datta S, Verma S, Verma A, Rakshit A, Bali A, Bhatti JS, Khurana A, Navik U. Therapeutic potential and pharmacological mechanism of visnagin. J Integr Med. 2024 Jul;22(4):399-412. doi: 10.1016/j.joim.2024.05.001. Epub 2024 May 8. PMID: 38797603. 8: Ndayambaje M, Wahnou H, Sow M, Chgari O, Habyarimana T, Karkouri M, Limami Y, Naya A, Oudghiri M. Exploring the multifaceted effects of Ammi visnaga: subchronic toxicity, antioxidant capacity, immunomodulatory, and anti- inflammatory activities. J Toxicol Environ Health A. 2024 Feb 16;87(4):150-165. doi: 10.1080/15287394.2023.2289430. Epub 2023 Dec 26. PMID: 38037686. 9: Sagir S, Seker U, Pekince Ozoner M, Yuksel M, Demir M. Oxidative stress, apoptosis, inflammation, and proliferation modulator function of visnagin provide gonadoprotective activity in testicular ischemia-reperfusion injury. Eur Rev Med Pharmacol Sci. 2023 Oct;27(20):9968-9977. doi: 10.26355/eurrev_202310_34176. PMID: 37916367. 10: Cantrell CL, Travaini ML, Bajsa-Hirschel J, Svendsen LD, Reichley A, Sosa GM, Kim SJ, Tamang P, Meepagala K, Duke SO. Synthesis, Herbicidal Activity, and Structure-Activity Relationships of O-Alkyl Analogues of Khellin and Visnagin. J Agric Food Chem. 2023 Oct 11;71(40):14593-14603. doi: 10.1021/acs.jafc.3c03254. Epub 2023 Sep 26. PMID: 37751400. 11: Qi X, Aiyasamy K, Alenezi SK, Alanazi IM, Alshammari MS, Ibrahim IAA. Anti- nociceptive and Anti-inflammatory Activities of Visnagin in Different Nociceptive and Inflammatory Mice Models. Appl Biochem Biotechnol. 2024 Jun;196(6):3441-3455. doi: 10.1007/s12010-023-04677-6. Epub 2023 Sep 2. PMID: 37659050. 12: Alsrhani A, Elderdery AY, Alzahrani B, Alzerwi NAN, Althobiti MM, Rayzah M, Idrees B, Elkhalifa AME, Subbiah SK, Mok PL. Therapeutic Potential of Albumin Nanoparticles Encapsulated Visnagin in MDA-MB-468 Triple-Negative Breast Cancer Cells. Molecules. 2023 Apr 4;28(7):3228. doi: 10.3390/molecules28073228. PMID: 37049991; PMCID: PMC10096807. 13: Harb N, Sarhan AG, El Dougdoug KA, Gomaa HHA. Ammi-visnaga extract; a novel phyto-antiviral agent against bovine rotavirus. Virusdisease. 2023 Mar;34(1):76-87. doi: 10.1007/s13337-022-00803-w. Epub 2023 Jan 4. PMID: 37009254; PMCID: PMC10050252. 14: Askari VR, Najafi Z, Baradaran Rahimi V, Boskabady MH. Comparative study on the impacts of visnagin and its methoxy derivative khellin on human lymphocyte proliferation and Th1/Th2 balance. Pharmacol Rep. 2023 Apr;75(2):411-422. doi: 10.1007/s43440-023-00452-w. Epub 2023 Feb 6. PMID: 36745338. 15: Rodrigues DF, Borges NHPB, Nogueira CES, Tavares JF, Arcanjo DDR, Barreto HM, Siqueira-Junior JP. Modulation of Drug Resistance by Furanochromones in NorA Overexpressing Staphylococcus Aureus. Evid Based Complement Alternat Med. 2022 Sep 17;2022:9244500. doi: 10.1155/2022/9244500. PMID: 36164399; PMCID: PMC9509268. 16: Gurram S, Anchi P, Panda B, Tekalkar SS, Mahajan RB, Godugu C. Amelioration of experimentally induced inflammatory arthritis by intra-articular injection of visnagin. Curr Res Pharmacol Drug Discov. 2022 Jul 9;3:100114. doi: 10.1016/j.crphar.2022.100114. PMID: 35992378; PMCID: PMC9389203. 17: Tian Q, Yin H, Li J, Jiang J, Ren B, Liu J. Neuroprotective, Anti- inflammatory Effect of Furanochrome, Visnagin Against Middle Cerebral Ischemia- Induced Rat Model. Appl Biochem Biotechnol. 2022 Dec;194(12):5767-5780. doi: 10.1007/s12010-022-04009-0. Epub 2022 Jul 11. PMID: 35819694. 18: Shah RP, Bharate SS. Analytical Methods for Furanochromone Natural Product, Khellin and Its Inspired Drug Candidates, Amiodarone and Sodium Cromoglycate. Crit Rev Anal Chem. 2024;54(4):691-706. doi: 10.1080/10408347.2022.2094198. Epub 2022 Jul 1. PMID: 35776740. 19: Rao XL, Liu LL, Huang J, Chen J. Neuroprotective effects of visnagin on cerebral ischemia-reperfusion injury rats and the underlying mechanisms. Eur Rev Med Pharmacol Sci. 2022 Jun;26(12):4371-4379. doi: 10.26355/eurrev_202206_29076. PMID: 35776038. 20: Erst AS, Chernonosov AA, Petrova NV, Kulikovskiy MS, Maltseva SY, Wang W, Kostikova VA. Investigation of Chemical Constituents of Eranthis longistipitata (Ranunculaceae): Coumarins and Furochromones. Int J Mol Sci. 2021 Dec 30;23(1):406. doi: 10.3390/ijms23010406. PMID: 35008829; PMCID: PMC8745120.