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MedKoo Cat#: 574093 | Name: Phomalactone
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Description:

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

Phomalactone is a fungal metabolite that is active against various strains of plant pathogenic fungi.

Chemical Structure

Phomalactone
Phomalactone
CAS#28921-94-0

Theoretical Analysis

MedKoo Cat#: 574093

Name: Phomalactone

CAS#: 28921-94-0

Chemical Formula: C8H10O3

Exact Mass: 154.0630

Molecular Weight: 154.17

Elemental Analysis: C, 62.33; H, 6.54; O, 31.13

Price and Availability

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1mg USD 600.00
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Related CAS #
No Data
Synonym
(+)-Phomalactone, Phomalactone
IUPAC/Chemical Name
(5S,6S)-5,6-dihydro-5-hydroxy-6-(1E)-1-propen-1-yl-2H-pyran-2-one
InChi Key
OKDRUMBNXIYUEO-VHJVCUAWSA-N
InChi Code
InChI=1S/C8H10O3/c1-2-3-7-6(9)4-5-8(10)11-7/h2-7,9H,1H3/b3-2+/t6-,7-/m0/s1
SMILES Code
O=C1C=C[C@H](O)[C@H](/C=C/C)O1
Appearance
Solid powder
Purity
>70% (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
>3 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Phomalactone, produced by the fungus Nigrospora sphaerica, specifically inhibits the mycelial growth of Phytophthora infestans, with an MIC value of 2.5 mg/L.
In vitro activity:
Phomalactone, 5,6-dihydro-5-hydroxy-6-prop-2-enyl-2H-pyran-2-one, produced by the fungus Nigrospora sphaerica, was tested in vitro against nine plant pathogenic fungi, and specifically inhibited the mycelial growth of Phytophthora infestans, with an MIC value of 2.5 mg litre-1. Reference: Pest Manag Sci. 2001 Jun;57(6):554-9. https://pubmed.ncbi.nlm.nih.gov/11407033/
In vivo activity:
TBD

Preparing Stock Solutions

The following data is based on the product molecular weight 154.17 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. Meepagala KM, Johnson RD, Techen N, Wedge DE, Duke SO. Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves. J Chem Ecol. 2015 Jul;41(7):602-12. doi: 10.1007/s10886-015-0602-x. Epub 2015 Jul 2. PMID: 26133676. 2. Kim JC, Choi GJ, Park JH, Kim HT, Cho KY. Activity against plant pathogenic fungi of phomalactone isolated from Nigrospora sphaerica. Pest Manag Sci. 2001 Jun;57(6):554-9. doi: 10.1002/ps.318. PMID: 11407033.
In vitro protocol:
1. Meepagala KM, Johnson RD, Techen N, Wedge DE, Duke SO. Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves. J Chem Ecol. 2015 Jul;41(7):602-12. doi: 10.1007/s10886-015-0602-x. Epub 2015 Jul 2. PMID: 26133676. 2. Kim JC, Choi GJ, Park JH, Kim HT, Cho KY. Activity against plant pathogenic fungi of phomalactone isolated from Nigrospora sphaerica. Pest Manag Sci. 2001 Jun;57(6):554-9. doi: 10.1002/ps.318. PMID: 11407033.
In vivo protocol:
TBD
1: Mazzone F, Simons VE, van Geelen L, Frank M, Mándi A, Kurtán T, Pfeffer K, Kalscheuer R. In Vitro Biological Activity of Natural Products from the Endophytic Fungus Paraboeremia selaginellae against Toxoplasma gondii. Antibiotics (Basel). 2022 Aug 31;11(9):1176. doi: 10.3390/antibiotics11091176. PMID: 36139955; PMCID: PMC9495004. 2: Ramesha KP, Chandra Mohana N, Chandra Nayaka S, Satish S. Epigenetic Modifiers Revamp Secondary Metabolite Production in Endophytic Nigrospora sphaerica. Front Microbiol. 2021 Dec 2;12:730355. doi: 10.3389/fmicb.2021.730355. PMID: 34925254; PMCID: PMC8678036. 3: Ramesha KP, Mohana NC, Nuthan BR, Rakshith D, Satish S. Antimicrobial metabolite profiling of Nigrospora sphaerica from Adiantum philippense L. J Genet Eng Biotechnol. 2020 Oct 22;18(1):66. doi: 10.1186/s43141-020-00080-4. PMID: 33094373; PMCID: PMC7581665. 4: Degenkolb T, Vilcinskas A. Metabolites from nematophagous fungi and nematicidal natural products from fungi as an alternative for biological control. Part I: metabolites from nematophagous ascomycetes. Appl Microbiol Biotechnol. 2016 May;100(9):3799-812. doi: 10.1007/s00253-015-7233-6. Epub 2015 Dec 29. PMID: 26715220; PMCID: PMC4824826. 5: Meepagala KM, Johnson RD, Techen N, Wedge DE, Duke SO. Phomalactone from a Phytopathogenic Fungus Infecting ZINNIA elegans (ASTERACEAE) Leaves. J Chem Ecol. 2015 Jul;41(7):602-12. doi: 10.1007/s10886-015-0602-x. Epub 2015 Jul 2. PMID: 26133676. 6: Prathumpai W, Kocharin K. Phomalactone optimization and production of entomopathogenic fungi by Ophiocordyceps communis BCC 1842 and BCC 2763. Prep Biochem Biotechnol. 2016;46(1):44-8. doi: 10.1080/10826068.2014.970691. PMID: 25285781. 7: Wu SH, Chen YW, Shao SC, Wang LD, Yu Y, Li ZY, Yang LY, Li SL, Huang R. Two new solanapyrone analogues from the endophytic fungus Nigrospora sp. YB-141 of Azadirachta indica. Chem Biodivers. 2009 Jan;6(1):79-85. doi: 10.1002/cbdv.200700421. PMID: 19180457. 8: Kim JC, Choi GJ, Park JH, Kim HT, Cho KY. Activity against plant pathogenic fungi of phomalactone isolated from Nigrospora sphaerica. Pest Manag Sci. 2001 Jun;57(6):554-9. doi: 10.1002/ps.318. PMID: 11407033. 9: Wrigley SK, Sadeghi R, Bahl S, Whiting AJ, Ainsworth AM, Martin SM, Katzer W, Ford R, Kau DA, Robinson N, Hayes MA, Elcock C, Mander T, Moore M. A novel (6S)-4,6-dimethyldodeca-2E,4E-dienoyl ester of phomalactone and related alpha- pyrone esters from a Phomopsis sp. with cytokine production inhibitory activity. J Antibiot (Tokyo). 1999 Oct;52(10):862-72. doi: 10.7164/antibiotics.52.862. PMID: 10604755. 10: Krasnoff SB, Gupta S. Identification of the antibiotic phomalactone from the entomopathogenic fungusHirsutella thompsonii var.synnematosa. J Chem Ecol. 1994 Feb;20(2):293-302. doi: 10.1007/BF02064437. PMID: 24242054.