ChemicalBook > CAS DataBase List > ROQUEFORTINE C

ROQUEFORTINE C

Product Name
ROQUEFORTINE C
CAS No.
58735-64-1
Chemical Name
ROQUEFORTINE C
Synonyms
Nsc292134;Aids031208;ROQUEFORTIN;Aids-031208;RORIFONE95%;ROQUEFORTINE;ROQUEFORTINE C;ISOROQUEFORTINE C;Roquefortine C in Methanol;PYRAZINO1215PYRROLO23BINDOLE143H5AH
CBNumber
CB8422875
Molecular Formula
C22H23N5O2
Formula Weight
389.45
MOL File
58735-64-1.mol
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ROQUEFORTINE C Property

Melting point:
202-205℃
Boiling point:
768.3±60.0 °C(Predicted)
Density 
1.37±0.1 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
chloroform: soluble1mg/mL
form 
White to off-white solid.
pka
11.10±0.40(Predicted)
color 
White to off-white
Stability:
Hygroscopic
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Safety

Hazard Codes 
T
Risk Statements 
23/24/25
Safety Statements 
22-36/37/39-45
RIDADR 
UN 2811 6.1/PG 2
WGK Germany 
3
RTECS 
UQ4730500
HS Code 
2941900000
Hazardous Substances Data
58735-64-1(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0406
Product name
Roquefortine C
Purity
≥98% (HPLC), from Penicillium roqueforti
Packaging
500μg
Price
$555
Updated
2024/03/01
Cayman Chemical
Product number
15376
Product name
Roquefortine C
Purity
≥98%
Packaging
500μg
Price
$171
Updated
2024/03/01
Cayman Chemical
Product number
15376
Product name
Roquefortine C
Purity
≥98%
Packaging
1mg
Price
$305
Updated
2024/03/01
Usbiological
Product number
207386
Product name
Roquefortine C
Packaging
500ug
Price
$316
Updated
2021/12/16
Usbiological
Product number
R2999-45
Product name
Roquefortine C
Packaging
500ug
Price
$523
Updated
2021/12/16
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ROQUEFORTINE C Chemical Properties,Usage,Production

Description

Roquefortine C is a mycotoxin that was first isolated from a strain of P. roqueforti, a species of Penicillium commercially used to ripen blue-veined cheeses. It has also been isolated from other members of the Penicillium genus found in contaminated food products where it displays neurotoxic properties. It has been shown to both activate a P-glycoprotein transport system involved in the efflux of xenobiotics and to inhibit cytochrome P450 3A detoxification enzymes. It has also been used as a biomarker for penitrem A intoxication.

Description

The third alkaloid isolated from a surface culture of Penicillium roqueforti, roquefortine C is present in only small quantities and the amount obtained is insufficient for the full structure to be established.

Uses

Roquefortine C is a potent tremorgenic mycotoxin originally isolated from Penicillium roqueforti in 1975 in Japan. Parallel research by Scott and colleagues lead to the structure elucidation of roquefortine C as an unusual diketopiperazine formed by coupling a prenylated tryptophan and histidine. Roquefortine C was subsequently found to be produced by a diverse range of fungi, most notably Penicillium species. Roquefortine is an important mycotoxin as low levels can be found in foodstuffs.

Uses

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).

Definition

ChEBI: Roquefortine C is a pyrroloindole.

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.

References

Ohmono et al., Agr. Bioi. Chem., 39, 1333 (1975)

ROQUEFORTINE C Preparation Products And Raw materials

Raw materials

Preparation Products

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ROQUEFORTINE C Suppliers

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58735-64-1, ROQUEFORTINE CRelated Search:


  • 10b-(1,1-dimethyl-2-propenyl)-6,10b,11,11a-tetrahydro-3-(1H-imidazol-4-ylmethylene)-2H-pyrazino(1,2:1,5)pyrrolo(2,3-b)indole-1,4(3H,5aH)-dione, Isoroquefortine C, Roquefortin, Roquefortine C
  • (3E,5aS,5aβ)-10bβ-(1,1-Dimethyl-2-propenyl)-3-(1H-imidazol-4-yl)methylene-6,10b,11,11aα-tetrahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
  • (5aS)-3-[(E)-(1H-Imidazole-4-yl)methylene]-10bβ-(1,1-dimethyl-2-propenyl)-1,3,4,5aβ,6,10b,11,11aα-octahydro-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4-dione
  • 2H-Pyrazino[1',2':1,5]pyrrolo[2,3-B]indole-1,4(3H,5ah)-dione, 10B-(1,1-dimethyl-2-propenyl)-6,10B,11,11A-tetrahydro-3-(1H-imidazol-4-ylmethylene)-, (3Z)-
  • Aids031208
  • Aids-031208
  • Nsc292134
  • 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)-
  • 1-dimethyl-2-propenyl)-3-(1h-imidazol-4-ylmethylene)-rahydro-10b-(
  • 2h-pyrazino(1’,2’:1,5)pyrrolo(2,3-b)indole-1,4-(3h,5ah)-dione,6,10b,11,11a-tet
  • ROQUEFORTIN
  • ROQUEFORTINE
  • ROQUEFORTINE C
  • ISOROQUEFORTINE C
  • 10B-(1,1-DIMETHYL-2-PROPENYL)-6,10B,11,11A-TETRAHYDRO-3-(1H-IMIDAZOL-4-YLMETHYLENE)-2H-PYRAZINO(1',2':1,5)PYRROLO(2,3-B)INDOLE-1,4(3H,5AH)-DIONE
  • roquefortine from penicillium*roqueforti
  • RORIFONE95%
  • PYRAZINO1215PYRROLO23BINDOLE143H5AH
  • Roquefortine C / isofumigaclavine C
  • Roquefortine C in Methanol
  • 58735-64-1
  • C22H23N5O2
  • Antibiotic