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ROQUEFORTINE C

CAS No.
58735-64-1
Chemical Name:
ROQUEFORTINE C
Synonyms
Nsc292134;Aids031208;ROQUEFORTIN;Aids-031208;RORIFONE95%;ROQUEFORTINE;ROQUEFORTINE C;ISOROQUEFORTINE C;PYRAZINO1215PYRROLO23BINDOLE143H5AH;roquefortine from penicillium*roqueforti
CBNumber:
CB8422875
Molecular Formula:
C22H23N5O2
Molecular Weight:
389.45
MDL Number:
MFCD00133802
MOL File:
58735-64-1.mol
Last updated:2023-07-12 17:06:00

ROQUEFORTINE C Properties

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)
Stability Hygroscopic
FDA UNII 4VW6U94XFK

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS06
Signal word  Danger
Hazard statements  H301+H311+H331
Precautionary statements  P280
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

ROQUEFORTINE C price More Price(8)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0406 Roquefortine C ≥98% (HPLC), from Penicillium roqueforti 58735-64-1 500μg $555 2024-03-01 Buy
Cayman Chemical 15376 Roquefortine C ≥98% 58735-64-1 500μg $171 2024-03-01 Buy
Cayman Chemical 15376 Roquefortine C ≥98% 58735-64-1 1mg $305 2024-03-01 Buy
Usbiological 207386 Roquefortine C 58735-64-1 500ug $316 2021-12-16 Buy
Usbiological R2999-45 Roquefortine C 58735-64-1 500ug $523 2021-12-16 Buy
Product number Packaging Price Buy
SML0406 500μg $555 Buy
15376 500μg $171 Buy
15376 1mg $305 Buy
207386 500ug $316 Buy
R2999-45 500ug $523 Buy

ROQUEFORTINE C Chemical Properties,Uses,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

Global( 53)Suppliers
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ATK CHEMICAL COMPANY LIMITED
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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 58735-64-1 C22H23N5O2 Antibiotic