Puberulonic acid
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| Category | Antibiotics |
| Catalog number | BBF-02074 |
| CAS | 82-83-7 |
| Molecular Weight | 224.12 |
| Molecular Formula | C9H4O7 |
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Description
Puberulonic acid is an aromatic derivative antibiotic produced by strains such as Pen. puberulum and Pen. aurantiovirens. It has weak anti-Gram-positive bacteria activity.
Specification
| IUPAC Name | 4,5,6-trihydroxycyclohepta[c]furan-1,3,7-trione |
| Canonical SMILES | C1=C2C(=C(C(=C(C1=O)O)O)O)C(=O)OC2=O |
| InChI | InChI=1S/C9H4O7/c10-3-1-2-4(9(15)16-8(2)14)6(12)7(13)5(3)11/h1H,(H3,10,11,12,13) |
| InChI Key | JAJRKOVXTSKCLS-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 404.2±45.0°C at 760 mmHg |
| Melting Point | 296-298°C (dec.) |
| Density | 2.0±0.1 g/cm3 |
Reference Reading
1. Synthesis and biological assessment of 3,7-dihydroxytropolones
D R Hirsch, D V Schiavone, A J Berkowitz, L A Morrison, T Masaoka, J A Wilson, E Lomonosova, H Zhao, B S Patel, S H Datla, S G Hoft, S J Majidi, R K Pal, E Gallicchio, L Tang, J E Tavis, S F J Le Grice, J A Beutler, R P Murelli Org Biomol Chem. 2017 Dec 19;16(1):62-69. doi: 10.1039/c7ob02453c.
3,7-Dihydroxytropolones (3,7-dHTs) are highly oxygenated troponoids that have been identified as lead compounds for several human diseases. To date, structure-function studies on these molecules have been limited due to a scarcity of synthetic methods for their preparation. New synthetic strategies towards structurally novel 3,7-dHTs would be valuable in further studying their therapeutic potential. Here we describe the successful adaptation of a [5 + 2] oxidopyrilium cycloaddition/ring-opening for 3,7-dHT synthesis, which we apply in the synthesis of a plausible biosynthetic intermediate to the natural products puberulic and puberulonic acid. We have also tested these new compounds in several biological assays related to human immunodeficiency virus (HIV), hepatitis B virus (HBV) and herpes simplex virus (HSV) in order to gain insight into structure-functional analysis related to antiviral troponoid development.
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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 ╳
