Synonym: 2H-Pyrazino[1′,2′:1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione, 10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-5-ylmethylene)-,(3E,5aS,10bR,11aS)-; Roquefortine from Penicillium roqueforti
CAS Number: 58735-64-1
Empirical Formula (Hill Notation): C22H23N5O2
Molecular Weight: 389.45
Linear Formula: C22H23N5O2
Product Type: Chemical
| assay |
≥98% (HPLC) |
| biological source |
Penicillium roqueforti |
| InChI |
1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9- |
| InChI key |
SPWSUFUPTSJWNG-SXGWCWSVSA-N |
| Quality Level |
200  |
| SMILES string |
N21C3Nc4c(cccc4)C3(CC2C(=O)NC(=C/c5nc[nH]c5)C1=O)C(C)(C)C=C |
| solubility |
chloroform: 1 mg/mL |
| |
DMSO: 10 mg/mL |
| |
ethyl acetate: 1 mg/mL |
| |
methanol: 10 mg/mL |
| storage temp. |
−20°C |
| Application: |
Roquefortine C has been used as a standard for the quantification of roquefortine C by high-performance liquid chromatography (HPLC). It has also been used as a standard for the quantification of roquefortine C by liquid chromatography-mass spectrometry (LC−MS/MS). |
| Biochem/physiol Actions: |
Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species. |
| Biochem/physiol Actions: |
Roquefortine C is a paralytic neurotoxin of a dioxopiperazine structure produced by a diverse range of fungi, most notably Penicillium species. It has been found in blue cheese and in many other food products due to natural occurrence and contamination. Roquefortine C was found to be active on a wide range of organisms. It inhibits the growth of Gram-positive bacteria, and cockerels treated with roquefortine lost their righting reflex and died within 8-12 hours. Mice injected with roquefortine C experienced neurotoxic properties. Roquefortine C was also reported to inhibit cytochrome P450 as well as tubulin polymerization. |
| Preparation Note: |
Soluble in methanol (10 mg/mL), DMSO (10 mg/mL), ethyl acetate (1 mg/mL) and chloroform (1 mg/mL). DMSO solution at 10 mg/mL is stable for 3 months at −20 °C. |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
−20°C |
| UNSPSC |
12161501 |
