Vermistatin | CAS#72669-21-7 | funicone-like compound

MedKoo Cat#: 145176 | Name: Vermistatin

Description:

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

Vermistatin is a funicone-like compound. Vermistatin could be developed as a mosquitocide. In a Cx. p. quinquefasciatus larvicidal bioassay, vermistatin (LC50 = 28.13 mg/L) was more toxic than dihydrovermistatin (LC50 = 83.87 mg/L).

Chemical Structure

Vermistatin

CAS#72669-21-7

Theoretical Analysis

MedKoo Cat#: 145176

Name: Vermistatin

CAS#: 72669-21-7

Chemical Formula: C18H16O6

Exact Mass: 328.0947

Molecular Weight: 328.32

Elemental Analysis: C, 65.85; H, 4.91; O, 29.24

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Vermistatin;

IUPAC/Chemical Name

(R,E)-4,6-dimethoxy-3-(4-oxo-6-(prop-1-en-1-yl)-4H-pyran-3-yl)isobenzofuran-1(3H)-one

InChi Key

YORFGPDHNOBVBM-BDUNBXCCSA-N

InChi Code

1S/C18H16O6/c1-4-5-10-7-14(19)13(9-23-10)17-16-12(18(20)24-17)6-11(21-2)8-15(16)22-3/h4-9,17H,1-3H3/b5-4+/t17-/m0/s1

SMILES Code

COC1=CC(OC)=C2[C@@H](OC(=O)C2=C1)C3=COC(\C=C\C)=CC3=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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 328.32 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: Ningsih BNS, Rukachaisirikul V, Phongpaichit S, Muanprasat C, Preedanon S, Sakayaroj J, Intayot R, Jungsuttiwong S. Talarostatin, a vermistatin derivative from the soil-derived fungus Talaromyces thailandensis PSU-SPSF059. Nat Prod Res. 2023 Mar 15:1-8. doi: 10.1080/14786419.2023.2188209. Epub ahead of print. PMID: 36919631. 2: Liu Y, Xia G, Li H, Ma L, Ding B, Lu Y, He L, Xia X, She Z. Vermistatin derivatives with α-glucosidase inhibitory activity from the mangrove endophytic fungus Penicillium sp. HN29-3B1. Planta Med. 2014 Jul;80(11):912-7. doi: 10.1055/s-0034-1382859. Epub 2014 Aug 12. PMID: 25116120. 3: Cerracchio C, Salvatore MM, Del Sorbo L, Serra F, Amoroso MG, DellaGreca M, Nicoletti R, Andolfi A, Fiorito F. In Vitro Evaluation of Antiviral Activities of Funicone-like Compounds Vermistatin and Penisimplicissin against Canine Coronavirus Infection. Antibiotics (Basel). 2023 Aug 15;12(8):1319. doi: 10.3390/antibiotics12081319. PMID: 37627739; PMCID: PMC10451237. 4: Adamcová J, Proksa B, Fuska J. Regulation of biosynthesis of vermiculin and vermistatin in Penicillium vermiculatum. Folia Microbiol (Praha). 1992;37(1):50-2. doi: 10.1007/BF02814580. PMID: 1505863. 5: Fuska J, Uhrín D, Proksa B, Votický Z, Ruppeldt J. The structure of vermistatin, a new metabolite from Penicillium vermiculatum. J Antibiot (Tokyo). 1986 Nov;39(11):1605-8. doi: 10.7164/antibiotics.39.1605. PMID: 3793630. 6: Lin J, Huo RY, Hou L, Jiang S, Wang SL, Deng YL, Liu L. New polyketides from the basidiomycetous fungus Pholiota sp. J Asian Nat Prod Res. 2023 Jul- Aug;25(7):674-682. doi: 10.1080/10286020.2022.2132481. Epub 2022 Oct 17. PMID: 36250229. 7: Chen J, Xu Z, Liu Y, Yang F, Guan L, Yang J, Li J, Niu G, Li J, Jin L. Talaromyces sp. Ethyl Acetate Crude Extract as Potential Mosquitocide to Control Culex pipiens quinquefasciatus. Molecules. 2023 Sep 15;28(18):6642. doi: 10.3390/molecules28186642. PMID: 37764417; PMCID: PMC10534940. 8: Murtaza N, Husain SA, Sarfaraz TB, Sultana N, Faizi S. Isolation and identification of vermistatin, ergosterol, stearic acid and mannitol, metabolic products of Penicillium verruculosum. Planta Med. 1997 Apr;63(2):191. doi: 10.1055/s-2006-957645. PMID: 17252345. 9: Stierle AA, Stierle DB, Girtsman T. Caspase-1 inhibitors from an extremophilic fungus that target specific leukemia cell lines. J Nat Prod. 2012 Mar 23;75(3):344-50. doi: 10.1021/np200414c. Epub 2012 Feb 1. PMID: 22295871; PMCID: PMC3330824. 10: Dethoup T, Manoch L, Kijjoa A, Pinto M, Gales L, Damas AM, Silva AM, Eaton G, Herz W. Merodrimanes and other constituents from Talaromyces thailandiasis. J Nat Prod. 2007 Jul;70(7):1200-2. doi: 10.1021/np0680578. Epub 2007 May 31. PMID: 17536857. 11: Liu Z, Xia G, Chen S, Liu Y, Li H, She Z. Eurothiocin A and B, sulfur- containing benzofurans from a soft coral-derived fungus Eurotium rubrum SH-823. Mar Drugs. 2014 Jun 20;12(6):3669-80. doi: 10.3390/md12063669. PMID: 24955555; PMCID: PMC4071596. 12: Gubiani JR, Wijeratne EM, Shi T, Araujo AR, Arnold AE, Chapman E, Gunatilaka AA. An epigenetic modifier induces production of (10'S)-verruculide B, an inhibitor of protein tyrosine phosphatases by Phoma sp. nov. LG0217, a fungal endophyte of Parkinsonia microphylla. Bioorg Med Chem. 2017 Mar 15;25(6):1860-1866. doi: 10.1016/j.bmc.2017.01.048. Epub 2017 Feb 3. PMID: 28202316; PMCID: PMC5362119. 13: Ge HM, Shen Y, Zhu CH, Tan SH, Ding H, Song YC, Tan RX. Penicidones A-C, three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp. Phytochemistry. 2008 Jan;69(2):571-6. doi: 10.1016/j.phytochem.2007.07.014. Epub 2007 Sep 4. PMID: 17804027. 14: Arai M, Tomoda H, Okuda T, Wang H, Tabata N, Masuma R, Yamaguchi Y, Omura S. Funicone-related compounds, potentiators of antifungal miconazole activity, produced by Talaromycesflavus FKI-0076. J Antibiot (Tokyo). 2002 Feb;55(2):172-80. doi: 10.7164/antibiotics.55.172. PMID: 12002999. 15: Xia XK, Liu F, She ZG, Yang LG, Li MF, Vrijmoed LL, Lin YC. 1H and 13C NMR assignments for 6-demethylvermistatin and two penicillide derivatives from the mangrove fungus Guignardia sp. (No. 4382) from the South China Sea. Magn Reson Chem. 2008 Jul;46(7):693-6. doi: 10.1002/mrc.2216. PMID: 18338749. 16: Proksa B, Sturdíková M, Mojumdar SC, Fuska J. Production of (-)-mitorubrinic acid byPenicillium vermiculatum. Folia Microbiol (Praha). 1997 Apr;42(2):133-5. doi: 10.1007/BF02898722. PMID: 18454334.