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MedKoo Cat#: 413385 | Name: Curvularin
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Description:

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

Curvularin is an antimicrobial made by Penicillium.

Chemical Structure

Curvularin
Curvularin
CAS#10140-70-2

Theoretical Analysis

MedKoo Cat#: 413385

Name: Curvularin

CAS#: 10140-70-2

Chemical Formula: C16H20O5

Exact Mass: 292.1311

Molecular Weight: 292.33

Elemental Analysis: C, 65.74; H, 6.90; O, 27.36

Price and Availability

Size Price Availability Quantity
1mg USD 285.00 Back order
5mg USD 750.00 Back order
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Related CAS #
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Synonym
Curvularin; (S)-Curvularin; (−)-Curvularin; NSC166071; NSC-166071; NSC 166071
IUPAC/Chemical Name
2H-3-Benzoxacyclododecin-2,10(1H)-dione, 4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-, (S)- (9CI)
InChi Key
VDUIGYAPSXCJFC-JTQLQIEISA-N
InChi Code
InChI=1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m0/s1
SMILES Code
O=C(O[C@@H](C)CCCCC1)CC2=CC(O)=CC(O)=C2C1=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
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
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 292.33 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: Choi HY, Le DD, Kim WG. Curvularin Isolated From Phoma macrostoma Is an Antagonist of RhlR Quorum Sensing in Pseudomonas aeruginosa. Front Microbiol. 2022 Jul 12;13:913882. doi: 10.3389/fmicb.2022.913882. PMID: 35903467; PMCID: PMC9315252. 2: Zhan J, Gunatilaka AA. Microbial transformation of curvularin. J Nat Prod. 2005 Aug;68(8):1271-3. doi: 10.1021/np0580309. PMID: 16124776. 3: Huo RY, Zhang JX, Jia J, Bi HK, Liu L. Alternarialone A, a new curvularin- type metabolite from the mangrove-derived fungus Alternaria longipes. J Asian Nat Prod Res. 2023 Jun;25(6):610-616. doi: 10.1080/10286020.2022.2117168. Epub 2022 Sep 1. PMID: 36048769. 4: Ye X, Anjum K, Song T, Wang W, Yu S, Huang H, Lian XY, Zhang Z. A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7. Nat Prod Res. 2016;30(10):1156-61. doi: 10.1080/14786419.2015.1047775. Epub 2015 Jun 29. PMID: 26119337. 5: Banala RR, Vemuri SK, Ev S, Av GR, Gpv S. The Anti-Inflammatory and Cytoprotective Efficiency of Curvularin, a Fungal Macrolactone against Lipopolysaccharide-Induced Inflammatory Response in Nucleus Pulposus Cells: An In Vitro Study. Asian Spine J. 2021 Apr;15(2):143-154. doi: 10.31616/asj.2019.0285. Epub 2020 Apr 8. PMID: 32252191; PMCID: PMC8055453. 6: Meng LH, Li XM, Lv CT, Li CS, Xu GM, Huang CG, Wang BG. Sulfur-containing cytotoxic curvularin macrolides from Penicillium sumatrense MA-92, a fungus obtained from the rhizosphere of the mangrove Lumnitzera racemosa. J Nat Prod. 2013 Nov 22;76(11):2145-9. doi: 10.1021/np400614f. Epub 2013 Nov 6. PMID: 24195466. 7: Ha TM, Ko W, Lee SJ, Kim YC, Son JY, Sohn JH, Yim JH, Oh H. Anti-Inflammatory Effects of Curvularin-Type Metabolites from a Marine-Derived Fungal Strain Penicillium sp. SF-5859 in Lipopolysaccharide-Induced RAW264.7 Macrophages. Mar Drugs. 2017 Sep 2;15(9):282. doi: 10.3390/md15090282. PMID: 28869509; PMCID: PMC5618421. 8: Vesonder RF, Ciegler A, Fennell D, Tjarks LW. Curvularin from penicillium baradicum Baghdadi NRRL 3754, and biological effects. J Environ Sci Health B. 1976;11(4):289-71. doi: 10.1080/03601237609372044. PMID: 1002951. 9: Elzner S, Schmidt D, Schollmeyer D, Erkel G, Anke T, Kleinert H, Förstermann U, Kunz H. Inhibitors of inducible NO synthase expression: total synthesis of (S)-curvularin and its ring homologues. ChemMedChem. 2008 Jun;3(6):924-39. doi: 10.1002/cmdc.200800022. PMID: 18366037. 10: Raistrick H, Rice FH. 2,3-Dihydro-3,6-dihydroxy-2-methyl-4-pyrone and curvularin from Penicillium gilmanii. J Chem Soc Perkin 1. 1971;18:3069-70. doi: 10.1039/j39710003069. PMID: 5165379. 11: Yao Y, Hausding M, Erkel G, Anke T, Förstermann U, Kleinert H. Sporogen, S14-95, and S-curvularin, three inhibitors of human inducible nitric-oxide synthase expression isolated from fungi. Mol Pharmacol. 2003 Feb;63(2):383-91. doi: 10.1124/mol.63.2.383. PMID: 12527810. 12: Xie LW, Ouyang YC, Zou K, Wang GH, Chen MJ, Sun HM, Dai SK, Li X. Isolation and difference in anti-Staphylococcus aureus bioactivity of curvularin derivates from fungus Eupenicillium sp. Appl Biochem Biotechnol. 2009 Oct;159(1):284-93. doi: 10.1007/s12010-009-8591-2. Epub 2009 Mar 31. PMID: 19333565. 13: Allu SR, Banne S, Jiang J, Qi N, Guo J, He Y. A Unified Synthetic Approach to Optically Pure Curvularin-Type Metabolites. J Org Chem. 2019 Jun 7;84(11):7227-7237. doi: 10.1021/acs.joc.9b00776. Epub 2019 May 24. PMID: 31083915. 14: Tadross PM, Virgil SC, Stoltz BM. Aryne acyl-alkylation in the general and convergent synthesis of benzannulated macrolactone natural products: an enantioselective synthesis of (-)-curvularin. Org Lett. 2010 Apr 2;12(7):1612-4. doi: 10.1021/ol100335y. PMID: 20196572. 15: Rudolph K, Serwe A, Erkel G. Inhibition of TGF-β signaling by the fungal lactones (S)-curvularin, dehydrocurvularin, oxacyclododecindione and galiellalactone. Cytokine. 2013 Jan;61(1):285-96. doi: 10.1016/j.cyto.2012.10.011. Epub 2012 Nov 5. PMID: 23134667. 16: Schmidt N, Art J, Forsch I, Werner A, Erkel G, Jung M, Horke S, Kleinert H, Pautz A. The anti-inflammatory fungal compound (S)-curvularin reduces proinflammatory gene expression in an in vivo model of rheumatoid arthritis. J Pharmacol Exp Ther. 2012 Oct;343(1):106-14. doi: 10.1124/jpet.112.192047. Epub 2012 Jul 5. PMID: 22767531. 17: Zhou F, Zhou Y, Guo Z, Yu X, Deng Z. Review of 10,11-Dehydrocurvularin: Synthesis, Structural Diversity, Bioactivities and Mechanisms. Mini Rev Med Chem. 2022;22(6):836-847. doi: 10.2174/1389557521666210428132256. PMID: 33913403. 18: Kumar CG, Mongolla P, Sujitha P, Joseph J, Babu KS, Suresh G, Ramakrishna KV, Purushotham U, Sastry GN, Kamal A. Metabolite profiling and biological activities of bioactive compounds produced by Chrysosporium lobatum strain BK-3 isolated from Kaziranga National Park, Assam, India. Springerplus. 2013 Dec;2(1):122. doi: 10.1186/2193-1801-2-122. Epub 2013 Mar 21. PMID: 23565355; PMCID: PMC3616213. 19: Deng Z, Deng A, Luo D, Gong D, Zou K, Peng Y, Guo Z. Biotransformation of (-)-(10E,15S)-10,11-Dehydrocurvularin. Nat Prod Commun. 2015 Jul;10(7):1277-8. PMID: 26411029. 20: Meena M, Samal S. Alternaria host-specific (HSTs) toxins: An overview of chemical characterization, target sites, regulation and their toxic effects. Toxicol Rep. 2019 Jul 17;6:745-758. doi: 10.1016/j.toxrep.2019.06.021. Erratum in: Toxicol Rep. 2020 Dec 22;8:28-29. PMID: 31406682; PMCID: PMC6684332.