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Roquefortine C is a mycotoxin that was first isolated from a strain of Penicillium roqueforti, a species of Penicillium commercially used to ripen blue-veined cheeses. It is an unusual diketopiperazine formed by coupling a prenylated tryptophan and histidine. Roquefortine C is present in only small quantities and has been found to be produced by a diverse range of fungi, most notably Penicillium species. 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.

58735-64-1

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58735-64-1 Usage

Uses

Used in Analytical Chemistry:
ROQUEFORTINE C is used as a standard for the quantification of roquefortine C by high-performance liquid chromatography (HPLC) for [application reason] accurate measurement and identification of the mycotoxin in various samples.
Used in Mass Spectrometry:
ROQUEFORTINE C is used as a standard for the quantification of roquefortine C by liquid chromatography-mass spectrometry (LC-MS/MS) for [application reason] precise detection and quantification of the mycotoxin in complex matrices.
Used in Food Safety and Contamination:
ROQUEFORTINE C is used as a biomarker for penitrem A intoxication in [application industry] food safety and contamination monitoring for [application reason] early detection of mycotoxin contamination in food products and ensuring public health.
Used in Pharmaceutical Research:
ROQUEFORTINE C is used as a research compound in [application industry] pharmaceutical research for [application reason] studying its neurotoxic properties and potential applications in drug development targeting specific biological pathways.

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)

Check Digit Verification of cas no

The CAS Registry Mumber 58735-64-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,8,7,3 and 5 respectively; the second part has 2 digits, 6 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 58735-64:
(7*5)+(6*8)+(5*7)+(4*3)+(3*5)+(2*6)+(1*4)=161
161 % 10 = 1
So 58735-64-1 is a valid CAS Registry Number.
InChI:InChI=1/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-/t17-,20-,22+/m0/s1

58735-64-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name ROQUEFORTINE C

1.2 Other means of identification

Product number -
Other names roquefortine from penicillium*roqueforti

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58735-64-1 SDS

58735-64-1Upstream product

58735-64-1Downstream Products

58735-64-1Relevant academic research and scientific papers

The total synthesis of roquefortine C and a rationale for the thermodynamic stability of isoroquefortine C over roquefortine C

Shangguan, Ning,Hehre, Warren J.,Ohlinger, William S.,Beavers, Mary Pat,Joullie, Madeleine M.

, p. 6281 - 6287 (2008/12/20)

The first total synthesis of roquefortine C is achieved by implementation of a novel elimination strategy to construct the thermodynamically unstable E-dehydrohistidine moiety. Molecular modeling studies are presented which explain the instability of the

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