Tenuazonic acid
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| Category | Antibiotics |
| Catalog number | BBF-03498 |
| CAS | 610-88-8 |
| Molecular Weight | 197.23 |
| Molecular Formula | C10H15NO3 |
| Purity | >98% |
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Description
Tenuazonic acid is a nitrogen-containing heterocyclic antibiotic produced by Alternaria tenuis Auct 430 and Asp. sp. 1404. It has inhibitory effect on enterovirus, respiratory virus, vaccinia virus and herpes simplex virus. It can inhibit KB cells and amoeba in dysentery.
Specification
| Synonyms | 3-acetyl-5-(butan-2-yl)-4-hydroxy-2,5-dihydro-1H-pyrrol-2-one |
| Storage | Store at -20°C |
| IUPAC Name | 4-acetyl-2-butan-2-yl-3-hydroxy-1,2-dihydropyrrol-5-one |
| Canonical SMILES | CCC(C)C1C(=C(C(=O)N1)C(=O)C)O |
| InChI | InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14) |
| InChI Key | CEIZFXOZIQNICU-UHFFFAOYSA-N |
| Source | Alternaria sp |
Properties
| Appearance | Light Yellow Oil |
| Antibiotic Activity Spectrum | viruses; parasites |
| Boiling Point | 401.068°C at 760 mmHg |
| Melting Point | 117°C |
| Flash Point | 196.4±28.7 °C |
| Density | 1.178 g/cm3 |
| Solubility | Soluble in DMSO |
Reference Reading
1. Mycotoxins: occurrence, toxicology, and exposure assessment
A J Ramos, S Marin, V Sanchis, G Cano-Sancho Food Chem Toxicol . 2013 Oct;60:218-37. doi: 10.1016/j.fct.2013.07.047.
Mycotoxins are abiotic hazards produced by certain fungi that can grow on a variety of crops. Consequently, their prevalence in plant raw materials may be relatively high. The concentration of mycotoxins in finished products is usually lower than in raw materials. In this review, occurrence and toxicology of the main mycotoxins are summarised. Furthermore, methodological approaches for exposure assessment are described. Existing exposure assessments, both through contamination and consumption data and biomarkers of exposure, for the main mycotoxins are also discussed.
2. Deacetyl- tenuazonic acid
David Siegel, Matthias Koch, Irene Nehls, Franziska Emmerling Acta Crystallogr Sect E Struct Rep Online . 2009 May 7;65(Pt 6):o1201. doi: 10.1107/S1600536809015372.
The heterocycle in the title compound {systematic name: (5S)-5-[(1S)-1-methyl-prop-yl]pyrrolidine-2,4-dione}, C(8)H(13)NO(2), is planar (r.m.s. deviation for all non-H atoms = 0.008 Å). The crystal structure is stabilized by N-H⋯O hydrogen bonding.
3. Tenuazonic acid production is dispensable for virulence, but its biosynthetic gene expression pattern is associated with the infection of Pyricularia oryzae
Choong-Soo Yun, Kazuko Yoshida, Takayuki Motoyama, Takeshi Kashiwa, Hiroyuki Osada Biosci Biotechnol Biochem . 2021 Dec 22;86(1):135-139. doi: 10.1093/bbb/zbab195.
Tenuazonic acid (TeA) is a toxin produced by the rice blast fungus Pyricularia oryzae. Although knockout of the TeA biosynthetic gene TAS1 did not affect the virulence of P. oryzae, constitutive TAS1 expression suppressed its infection. TAS1 expression was induced alongside transition of P. oryzae infection behavior. The results suggested that controlling TeA biosynthesis is important for P. oryzae infection.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
