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MedKoo Cat#: 585116 | Name: Roquefortine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Roquefortine is a metabolite of Penicillium roqueforti.

Chemical Structure

Roquefortine
Roquefortine
CAS#58735-64-1

Theoretical Analysis

MedKoo Cat#: 585116

Name: Roquefortine

CAS#: 58735-64-1

Chemical Formula: C22H23N5O2

Exact Mass: 389.1852

Molecular Weight: 389.46

Elemental Analysis: C, 67.85; H, 5.95; N, 17.98; O, 8.22

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Roquefortine
IUPAC/Chemical Name
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)-
InChi Key
SPWSUFUPTSJWNG-SXGWCWSVSA-N
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-
SMILES Code
O=C(C(N1C/2=O)CC3(C(C)(C)C=C)C1NC4=C3C=CC=C4)NC2=C/C5=CNC=N5
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 389.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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PubMed PMID: 31284717; PubMed Central PMCID: PMC6713467. 4: Hammerl R, Frank O, Schmittnägel T, Ehrmann MA, Hofmann T. Functional Metabolome Analysis of Penicillium roqueforti by Means of Differential Off-Line LC-NMR. J Agric Food Chem. 2019 May 8;67(18):5135-5146. doi: 10.1021/acs.jafc.9b00388. Epub 2019 Apr 29. PubMed PMID: 30950274. 5: Adekoya I, Njobeh P, Obadina A, Landschoot S, Audenaert K, Okoth S, De Boevre M, De Saeger S. Investigation of the Metabolic Profile and Toxigenic Variability of Fungal Species Occurring in Fermented Foods and Beverage from Nigeria and South Africa Using UPLC-MS/MS. Toxins (Basel). 2019 Feb 1;11(2). pii: E85. doi: 10.3390/toxins11020085. PubMed PMID: 30717215; PubMed Central PMCID: PMC6409632. 6: Olsen M, Lindqvist R, Bakeeva A, Leong SL, Sulyok M. Distribution of mycotoxins produced by Penicillium spp. inoculated in apple jam and crème fraiche during chilled storage. Int J Food Microbiol. 2019 Mar 2;292:13-20. doi: 10.1016/j.ijfoodmicro.2018.12.003. Epub 2018 Dec 7. PubMed PMID: 30553178. 7: Prencipe S, Siciliano I, Gatti C, Garibaldi A, Gullino ML, Botta R, Spadaro D. Several species of Penicillium isolated from chestnut flour processing are pathogenic on fresh chestnuts and produce mycotoxins. Food Microbiol. 2018 Dec;76:396-404. doi: 10.1016/j.fm.2018.07.003. Epub 2018 Jul 3. PubMed PMID: 30166166. 8: Newmister SA, Romminger S, Schmidt JJ, Williams RM, Smith JL, Berlinck RGS, Sherman DH. Unveiling sequential late-stage methyltransferase reactions in the meleagrin/oxaline biosynthetic pathway. Org Biomol Chem. 2018 Sep 11;16(35):6450-6459. doi: 10.1039/c8ob01565a. PubMed PMID: 30141817; PubMed Central PMCID: PMC6134404. 9: Botha CJ, Visagie CM, Sulyok M. Putative neuromycotoxicoses in an adult male following ingestion of moldy walnuts. Mycotoxin Res. 2019 Feb;35(1):9-16. doi: 10.1007/s12550-018-0326-1. Epub 2018 Aug 7. PubMed PMID: 30088215. 10: Ssepuuya G, Van Poucke C, Ediage EN, Mulholland C, Tritscher A, Verger P, Kenny M, Bessy C, De Saeger S. Mycotoxin contamination of sorghum and its contribution to human dietary exposure in four sub-Saharan countries. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2018 Jul;35(7):1384-1393. doi: 10.1080/19440049.2018.1461253. Epub 2018 Jun 18. PubMed PMID: 29912638. 11: Wambacq E, Audenaert K, Höfte M, De Saeger S, Haesaert G. Bacillus velezensis as antagonist towards Penicillium roqueforti s.l. in silage: in vitro and in vivo evaluation. J Appl Microbiol. 2018 Oct;125(4):986-996. doi: 10.1111/jam.13944. Epub 2018 Jul 24. PubMed PMID: 29873155. 12: Rojas-Aedo JF, Gil-Durán C, Goity A, Vaca I, Levicán G, Larrondo LF, Chávez R. The developmental regulator Pcz1 affects the production of secondary metabolites in the filamentous fungus Penicillium roqueforti. Microbiol Res. 2018 Jul - Aug;212-213:67-74. doi: 10.1016/j.micres.2018.05.005. Epub 2018 May 4. PubMed PMID: 29853169. 13: Niu S, Wang N, Xie CL, Fan Z, Luo Z, Chen HF, Yang XW. Roquefortine J, a novel roquefortine alkaloid, from the deep-sea-derived fungus Penicillium granulatum MCCC 3A00475. J Antibiot (Tokyo). 2018 Jul;71(7):658-661. doi: 10.1038/s41429-018-0046-y. Epub 2018 Apr 4. PubMed PMID: 29618769. 14: Hymery N, Mounier J, Coton E. Effect of Penicillium roqueforti mycotoxins on Caco-2 cells: Acute and chronic exposure. Toxicol In Vitro. 2018 Apr;48:188-194. doi: 10.1016/j.tiv.2018.01.017. PubMed PMID: 29408666. 15: Torrent C, Gil-Durán C, Rojas-Aedo JF, Medina E, Vaca I, Castro P, García-Rico RO, Cotoras M, Mendoza L, Levicán G, Chávez R. Role of sfk1 Gene in the Filamentous Fungus Penicillium roqueforti. Front Microbiol. 2017 Dec 6;8:2424. doi: 10.3389/fmicb.2017.02424. eCollection 2017. PubMed PMID: 29270163; PubMed Central PMCID: PMC5723657. 16: Fernández-Bodega Á, Álvarez-Álvarez R, Liras P, Martín JF. Silencing of a second dimethylallyltryptophan synthase of Penicillium roqueforti reveals a novel clavine alkaloid gene cluster. Appl Microbiol Biotechnol. 2017 Aug;101(15):6111-6121. doi: 10.1007/s00253-017-8366-6. Epub 2017 Jun 16. Erratum in: Appl Microbiol Biotechnol. 2017 Sep 12;:. PubMed PMID: 28620689. 17: Camardo Leggieri M, Decontardi S, Bertuzzi T, Pietri A, Battilani P. Modeling Growth and Toxin Production of Toxigenic Fungi Signaled in Cheese under Different Temperature and Water Activity Regimes. Toxins (Basel). 2016 Dec 24;9(1). pii: E4. doi: 10.3390/toxins9010004. PubMed PMID: 28029129; PubMed Central PMCID: PMC5308237. 18: Dagnac T, Latorre A, Fernández Lorenzo B, Llompart M. Validation and application of a liquid chromatography-tandem mass spectrometry based method for the assessment of the co-occurrence of mycotoxins in maize silages from dairy farms in NW Spain. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2016 Dec;33(12):1850-1863. Epub 2016 Oct 26. 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