A mycotoxin
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Roquefortine C

Item No. 15376

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3E,5aS,10bR)-10b-(1,1-dimethyl-2-propen-1-yl)-6,10b,11,11aS-tetrahydro-3-(1H-imidazol-5-ylmethylene)-2H-pyrazino[1',2':1,5]pyrrolo[2,3-b]indole-1,4(3H,5aH)-dione
CAS Number
58735-64-1
Synonyms
  • NSC 292134
Molecular Formula
C22H23N5O2
Formula Weight
389.5
Purity
≥98%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
CC([C@]12C3=CC=CC=C3N[C@]1(N([C@@]([H])(C2)C(N/4)=O)C(C4=C/C5=CN=CN5)=O)[H])(C=C)C
InChi Code
InChI=1S/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
InChi Key
SPWSUFUPTSJWNG-JJUKSXGLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product 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.1 It has also been isolated from other members of the Penicillium genus found in contaminated food products where it displays neurotoxic properties.2 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.3 It has also been used as a biomarker for penitrem A (Item No. 11347) intoxication.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. García-Rico, R.O., Chávez, R., Fierro, F., et al. Effect of a heterotrimeric G protein α subunit on conidia germination, stress response, and roquefortine C production in Penicillium roqueforti. Int. Microbiol. 12(2), 123-129 (2009).

    2. Richard, D.J., Schiavi, B., and Joullié, M.M. Synthetic studies of roquefortine C: Synthesis of isoroquefortine C and a heterocycle. Proc. Natl. Acad. Sci. USA 101(33), 11971-11976 (2004).

    3. Aninat, C., André, F., and Delaforge, M. Oxidative metabolism by P450 and function coupling to efflux systems: Modulation of mycotoxin toxicity. Food Addit. Contam. 22(4), 361-368 (2005).

    4. Tiwary, A.K., Puschner, B., and Poppenga, R.H. Using roquefortine C as a biomarker for penitrem A intoxication. J. Vet. Diagn. Invest. 21(2), 237-239 (2009).