(Z)-Pterulinic Acid
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| Category | Mycotoxins |
| Catalog number | BBF-03285 |
| CAS | 530087-05-9 |
| Molecular Weight | 290.70 |
| Molecular Formula | C15H11ClO4 |
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Description
(Z)-Pterulinic Acid is a Coenzyme I: Coenzyme Q oxidoreductase inhibitor produced by Pterula sp. 82168. It has anti-yeast and filamentous fungus effect and has cytotoxic activity.
Specification
| IUPAC Name | 2-[(7Z)-7-(chloromethylidene)furo[3,2-h][1]benzoxepin-2-yl]acetic acid |
| Canonical SMILES | C1C(=CCl)C=CC2=C(O1)C=C3C(=C2)C=C(O3)CC(=O)O |
| InChI | InChI=1S/C15H11ClO4/c16-7-9-1-2-10-3-11-4-12(5-15(17)18)20-14(11)6-13(10)19-8-9/h1-4,6-7H,5,8H2,(H,17,18)/b9-7- |
| InChI Key | MMKVRUNBWGNULK-CLFYSBASSA-N |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | fungi; yeast |
| Boiling Point | 501.0±50.0°C at 760 mmHg |
| Melting Point | 165-167°C |
| Density | 1.492±0.06 g/cm3 |
Reference Reading
1. Pterulinic acid and pterulone, two novel inhibitors of NADH:ubiquinone oxidoreductase (complex I) produced by a Pterula species. II. Physico-chemical properties and structure elucidation
M Engler, T Anke, O Sterner J Antibiot (Tokyo). 1997 Apr;50(4):330-3. doi: 10.7164/antibiotics.50.330.
The structures of two novel fungal antibiotics, isolated from a Pterula species, that interfere with the NADH:ubiquinone oxidoreductase and inhibit the respiration of eucaryotes, were determined by spectroscopic techniques. Both compounds, pterulinic acid (1a) and pterulone (2), contain a 1-benzoxepin ring system and are chlorinated. Pterulinic acid (1a), which was obtained as a 1:5 inseparable mixture of the two isomers (Z)-1a and (E)-1a, in addition contains a furan. Their structures were determined by mass spectrometry and NMR spectroscopy, and 2D heteronuclear correlation experiments permitted the assignment of all NMR signals.
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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 ╳
