Roquefortine

Base Information

• Chemical Name: Roquefortine
• CAS No.: 58735-64-1
• Molecular Formula: C₂₂H₂₃N₅O₂
• Molecular Weight: 389.457
• Hs Code.: 2933990090
• Nikkaji Number: J1.727.819C,J460.722H
• Wikipedia: Roquefortine_C
• Wikidata: Q63399765
• Mol file: 58735-64-1.mol

Synonyms:isoroquefortine C;roquefortin;roquefortine;roquefortine C

Chemical Property of Roquefortine

Chemical Property:

• Vapor Pressure: 1.61E-23mmHg at 25°C
• Melting Point: 202-205℃
• Boiling Point: 768.3°Cat760mmHg
• Flash Point: 418.4°C
• PSA: 90.12000
• Density: 1.37g/cm³
• LogP: 2.78780
• Storage Temp.: −20°C
• Solubility.: chloroform: soluble1mg/mL
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 389.18517499
• Heavy Atom Count: 29
• Complexity: 777

Purity/Quality:

97% ^*data from raw suppliers

Roquefortine C ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 22-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Mycotoxins
• Canonical SMILES: CC(C)(C=C)C12CC3C(=O)NC(=CC4=CN=CN4)C(=O)N3C1NC5=CC=CC=C25
• Isomeric SMILES: CC(C)(C=C)[C@@]12C[C@H]3C(=O)N/C(=C\C4=CN=CN4)/C(=O)N3[C@@H]1NC5=CC=CC=C25
• 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. 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.
• 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). 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.

Technology Process of Roquefortine

There total 3 articles about Roquefortine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C23H27N5O3 → roquefortine C (58735-64-1)

Guidance literature:

With ammonium hydroxide; In methanol; at 20 ℃; for 1h;

DOI:10.1021/ja800067q

Reference yield:

→ roquefortine C (58735-64-1,68628-81-9)

Guidance literature:

Aus Roquefortin u. hν;

DOI:10.1021/jf60221a052

Reference yield:

→ roquefortine C (58735-64-1)

Guidance literature:

Aus penicillium roqueforti;

DOI:10.1271/bbb1961.41.2097