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:

N-phenyl isonicotinamide ROQUEFORTINE E 1-Allyl-2-aminomethylpyrrolidine 1-Methylpiperazin-2-one 1-(2-PHENYLETHYL)PIPERAZINE 1H-Indol-2-amine N-Isobutyl piperazine ROQUEFORTINE C 2-(3-PHENYL-PYRROLIDIN-1-YL)-ETHYLAMINE 1-ETHYL-2-METHYL-PIPERAZINE hexahydropyrrolo[1,2-a]pyrazin-4(1H)-one N-[1-(aminomethyl)butyl]-N,N-dimethylamine N-METHYL-N-(2-PHENYLETHYL)ETHANE-1,2-DIAMINE HEXAHYDROPYRROLO[1,2-A]PYRAZINE-1,4-DIONE (+/-)-1,4-DIAZABICYCLO[4.4.0]DECANE 1-ETHYLPIPERAZIN-2-ONE Piperazinone, 1-butyl- (9CI) CHEMBRDG-BB 4012298

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