Penigequinolone A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04586 |
| CAS | 180045-91-4 |
| Molecular Weight | 467.55 |
| Molecular Formula | C27H33NO6 |
| Purity | >99% by HPLC |
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Description
A rare fungal metabolite produced by selected penicillium species. It is a pollen growth inhibitor.
Specification
| Synonyms | 2(1H)-Quinolinone, 3,4-dihydro-4,5-dihydroxy-3-methoxy-4-(4-methoxyphenyl)-6-[(E)-2-[(2S)-tetrahydro-2,5,5-trimethyl-2H-pyran-2-yl]ethenyl]-, (3R,4R)-; [3R-[3α,4α,6[E(S*)]]]-3,4-Dihydro-4,5-dihydroxy-3-methoxy-4-(4-methoxyphenyl)-6-[2-(tetrahydro-2,5,5-trimethyl-2H-pyran-2-yl)ethenyl]-2(1H)-quinolinone |
| Storage | Store at -20°C |
| IUPAC Name | (3R,4R)-4,5-dihydroxy-3-methoxy-4-(4-methoxyphenyl)-6-[(E)-2-[(2S)-2,5,5-trimethyloxan-2-yl]ethenyl]-1,3-dihydroquinolin-2-one |
| Canonical SMILES | CC1(CCC(OC1)(C)C=CC2=C(C3=C(C=C2)NC(=O)C(C3(C4=CC=C(C=C4)OC)O)OC)O)C |
| InChI | InChI=1S/C27H33NO6/c1-25(2)14-15-26(3,34-16-25)13-12-17-6-11-20-21(22(17)29)27(31,23(33-5)24(30)28-20)18-7-9-19(32-4)10-8-18/h6-13,23,29,31H,14-16H2,1-5H3,(H,28,30)/b13-12+/t23-,26+,27+/m0/s1 |
| InChI Key | CVWJKBJRSZXDIW-WIAMJCSFSA-N |
| Source | Penicillium sp. |
Properties
| Appearance | White Powder |
| Boiling Point | 649.6±55.0°C at 760 mmHg |
| Density | 1.3±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Nematicidal alkaloids and related compounds produced by the fungus Penicillium cf. simplicissimum
J Uzawa, Y Kimura, H Koshino, S Fujioka, T Kawano, M Kusano Biosci Biotechnol Biochem . 2000 Dec;64(12):2559-68. doi: 10.1271/bbb.64.2559.
A new nematicidal alkaloid, peniprequinolone (1), together with the known alkaloids penigequinolones A and B (2a, 2b), 3-methoxy-4-hydroxy-4-(4'-methoxyphenyl)quinolinone (3), and 3-methoxy-4,6-dihydroxy-4-(4'-methoxyphenyl)quinolinone (4), were isolated from Penicillium cf. simplicissimum (Oudemans) Thom. Cyclopenin (5) and a compound (6a/6b) structurally related to cyclopenin also were isolated from the fungus, and their structures were established by spectroscopic analysis. The biological activities of 1, 2, 3, 4, and 5 were examined by a bioassay with root-lesion nematodes.
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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 ╳
