Fumigatin | CAS#484-89-9 | metabolite

MedKoo Cat#: 149221 | Name: Fumigatin

Description:

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

Fumigatin is a secondary metabolite produced by the fungus Aspergillus fumigatus, belonging to the class of mycotoxins known as isocoumarins. It exhibits antimicrobial and cytotoxic properties, making it of interest in pharmaceutical and toxicological research. The mechanism of fumigatin is not fully characterized but is believed to involve inhibition of key enzymes and interference with cellular respiration or protein synthesis in target organisms. Its applications are primarily in the study of fungal pathogenesis and the development of antifungal or anticancer agents.

Chemical Structure

Fumigatin

CAS#484-89-9

Theoretical Analysis

MedKoo Cat#: 149221

Name: Fumigatin

CAS#: 484-89-9

Chemical Formula: C8H8O4

Exact Mass: 168.0423

Molecular Weight: 168.15

Elemental Analysis: C, 57.14; H, 4.80; O, 38.06

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

Fumigatin;

IUPAC/Chemical Name

3-hydroxy-2-methoxy-5-methylcyclohexa-2,5-diene-1,4-dione

InChi Key

GSNBWTFAGXSQCO-UHFFFAOYSA-N

InChi Code

1S/C8H8O4/c1-4-3-5(9)8(12-2)7(11)6(4)10/h3,11H,1-2H3

SMILES Code

COC1=C(O)C(=O)C(C)=CC1=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 168.15 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: Packter NM. Studies on the biosynthesis of quinones in fungi. Incorporation of 6-methylsalicylic acid into fumigatin and related compounds in Aspergillus fumigatus I.M.I. 89353. Biochem J. 1965 Nov;97(2):321-32. doi: 10.1042/bj0970321. PMID: 16749133; PMCID: PMC1264643. 2: Wang L, Zhang X, Zhang K, Zhang X, Zhu T, Che Q, Zhang G, Li D. Overexpression of Global Regulator PbrlaeA Leads to the Discovery of New Polyketide in Fungus Penicillium Brocae HDN-12-143. Front Chem. 2020 Apr 21;8:270. doi: 10.3389/fchem.2020.00270. PMID: 32373583; PMCID: PMC7186497. 3: Kang D, Son GH, Park HM, Kim J, Choi JN, Kim HY, Lee S, Hong SB, Lee CH. Culture condition-dependent metabolite profiling of Aspergillus fumigatus with antifungal activity. Fungal Biol. 2013 Mar;117(3):211-9. doi: 10.1016/j.funbio.2013.01.009. Epub 2013 Feb 14. PMID: 23537878. 4: Anslow WK, Raistrick H. Studies in the biochemistry of micro-organisms: Fumigatin (3-hydroxy-4-methoxy-2:5-toluquinone), and spinulosin (3:6-dihydroxy-4-methoxy-2:5-toluquinone), metabolic products respectively of Aspergillus fumigatus Fresenius and Penicillium spinulosum Thom. Biochem J. 1938 Apr;32(4):687-96. doi: 10.1042/bj0320687. PMID: 16746672; PMCID: PMC1264089. 5: Lafond-Grellety J, Hocquellet P, Serceau R. Modalités de formation de la fumigatine et de la spinulosine par Aspergillus fumigatus Fres et dosage polarographique de ces toxines [Process of fumigatin and spinulosin formation by Aspergillus fumigatus Fres and polarographic assay of these toxins (author's transl)]. Ann Microbiol (Paris). 1978 Jul;129B(1):3-18. French. PMID: 31124. 6: Simonart P, Verachtert H. Sur la biosynthèse de la fumigatine [On the biosynthesis of fumigatin]. Bull Soc Chim Biol (Paris). 1967;49(5):543-9. French. PMID: 6059792. 7: Packter NM. Studies on the biosynthesis of phenols in fungi. Conversion of [14C]orsellinic acid and [14C]orcinol into fumigatol by Aspergillus fumigatus I.M.I. 89353. Biochem J. 1966 Feb;98(2):353-9. doi: 10.1042/bj0980353. PMID: 5296209; PMCID: PMC1264851. 8: PACKTER NM, GLOVER J. BIOSYNTHESIS OF (14C)FUMIGATIN IN ASPERGILLUS FUMIGATUS, FRESENIUS. Biochim Biophys Acta. 1965 Apr 12;100:50-6. doi: 10.1016/0304-4165(65)90426-5. PMID: 14323648. 9: Yamamoto Y, Hirai T, Okada K, Saito K. Studies on the metabolic products of a strain of Aspergillus fumigatus DH 413. VI. Metabolic position of 3,4-dihydroxytoluquinone and fumigatin chlorohydrin in fumigatin biosynthesis. Chem Pharm Bull (Tokyo). 1974 Jan;22(1):83-7. doi: 10.1248/cpb.22.83. PMID: 4598457. 10: Yamazaki Y, Yasuda K, Matsuyama T, Ishihara T, Higa R, Sawairi T, Yamaguchi M, Egi M, Akai S, Miyase T, Ikari A, Miwa M, Sugatani J. A Penicillium sp. F33 metabolite and its synthetic derivatives inhibit acetyl-CoA:1-O-alkyl-sn- glycero-3-phosphocholine acetyltransferase (a key enzyme in platelet-activating factor biosynthesis) and carrageenan-induced paw edema in mice. Biochem Pharmacol. 2013 Sep 1;86(5):632-44. doi: 10.1016/j.bcp.2013.06.021. Epub 2013 Jun 28. PMID: 23817078. 11: Shunk CH, McPherson JF, Folkers K. Synthesis of coenzyme Q analogs by alkylation of fumigatin. J Org Chem. 1966 May;31(5):1638-9. doi: 10.1021/jo01343a505. PMID: 5931942. 12: Lee MY, Park HM, Son GH, Lee CH. Liquid chromatography-mass spectrometry- based chemotaxonomic classification of Aspergillus spp. and evaluation of the biological activity of its unique metabolite, neosartorin. J Microbiol Biotechnol. 2013;23(7):932-41. doi: 10.4014/jmb.1212.12068. PMID: 23711526. 13: Khruengsai S, Pripdeevech P, D'Souza PE, Panuwet P. Biofumigation activities of volatile compounds from two Trichoderma afroharzianum strains against Fusarium infections in fresh chilies. J Sci Food Agric. 2021 Nov;101(14):5861-5871. doi: 10.1002/jsfa.11238. Epub 2021 Apr 15. PMID: 33788973.