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207074 Aspyrone ((5S,6R)-5-Hydroxy-6-methyl-3-((2S,3S)-3-methyl-oxiran-2-yl)-5,6-dihydro-2H-pyran-2-one) CAS: 17398-00-4

Specifications
References
CAS Number
17398-00-4
Grade
Highly Purified
Molecular Formula
C9H12O4
Molecular Weight
184.2
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
-20°C

Antibiotic. Shows nematicidal, insecticidal, antibacterial and antifungal activity. Related to asperlactone and aspinonene.

Synonyms
(5S,6R)-5-Hydroxy-6-methyl-3-((2S,3S)-3-methyl-oxiran-2-yl)-5,6-dihydro-2H-pyran-2-one
CAS Number
17398-00-4
Source
Aspergillus ochraceus
Molecular Formula
C9H12O4
Solubility
DMSO, acetone or methanol
Method for Determining Identity
Proton NMR
Molecular Weight
184.2
Purity
≥98% (HPLC)
Appearance
Supplied as a white to off-white solid.
Storage and Stability
Lyophilized powder may be stored at -20°C. Stable for 12 months after receipt at -20°C. Reconstitute with sterile buffer or ddH2O. Aliquot to avoid repeated freezing and thawing. Store at -20°C. Reconstituted product is stable for 6 months at -20°C. For maximum recovery of product, centrifuge the original vial after thawing and prior to removing the cap. Further dilutions can be made in assay buffer.
Source
Aspergillus ochraceus
Purity
≥98% (HPLC)
Form
Supplied as a white to off-white solid.
Important Note
This product as supplied is intended for research use only, not for use in human, therapeutic or diagnostic applications without the expressed written authorization of United States Biological.
References
1. A new metabolite of Aspergillus melleus: S.D. Mills & W.B. Turner; J. Chem. Soc. (C) 2242 (1967). 2. Production of 3-(1,2-epoxypropyl)-5,6-dihydro-5-hydroxy-6-methylpyran-2-one by Aspergillus ochraceus Wilhelm: J.H. Moore, et al.; J. Agr. Food Chem. 22: 697 (1974). 3. J.S.E. Holker, et al.; J.C.S. Perkin Trans. 1: 1397 (1981) 4. Biosynthesis of aspyrone, a metabolite of Aspergillus melleus: advanced precursor studies to identify the product of the polyketide synthase: J. Staunton & A.C. Sutkowski; J.C.S. Chem. Commun. 1108 (1991). 5. The polyketide synthase (PKS) of aspyrone biosynthesis: evidence for the enzyme bound intermediates from incorporation studies with N-acetylcysteamine thioesters in intact cells of Aspergillus melleus: J. Staunton & A.C. Sutkowski; J.C.S. Chem. Commun. 1110 (1991). 6. Biosynthesis of aspinonene, a branched pentaketide by Aspergillis ochraceus, related to aspyrone: J. Fuchser, et al.; J. Chem. Soc. Perkin Trans 1: 1663 (1995). 7. Effect of fungal metabolites and some derivatives against Tribolium castaneum (Herbst) and Nezara viridula (L.): M. Balcells, et al.; Pestic. Sci. 45: 319 (1995). 8. Synthesis of chiral aspyrone, a multi-functional dihydropyranone antibiotic: T. Sugiyama, et al.; Biosci. Biotech. Biochem. 59: 1921 (1995). 9. Aspyrone, a nematicidal compound isolated from the fungus, Aspergillus melleus: Y. Kimura, et al.; Biosci. Biotech. Biochem. 60: 375 (1996) 10. Bactericidal and fungicidal activity of Aspergillus ochraceus metabolites and some derivatives: M. Torres, et al.; Pestic. Sci. 53: 9 (1998). 11. Aspinolide and aspinonene/aspyrone co-metabolites, new pentaketides produced by Aspergillus ochraceus: J. Fuchser & A. Zeeck; Liebigs Ann./Recueil , 87 (1997)
USBio References
No references available
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