Citrinin | CAS# 518-75-2 | mycotoxin

MedKoo Cat#: 574470 | Name: Citrinin

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Description:

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

Citrinin is a mycotoxin that exerts cytotoxic and genotoxic effects in various mammalian cells, causing mycotoxic nephropathy in livestock and Balkan nephropathy and yellow rice fever in humans. Because citrinin induces apoptosis and blocks tubulin polymerization as well as mitotic spindle assembly, it is useful as a biological research reagent.

Chemical Structure

Citrinin

CAS#518-75-2

Theoretical Analysis

MedKoo Cat#: 574470

Name: Citrinin

CAS#: 518-75-2

Chemical Formula: C13H14O5

Exact Mass: 250.0841

Molecular Weight: 250.25

Elemental Analysis: C, 62.39; H, 5.64; O, 31.97

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 350.00	2 Weeks
10mg	USD 600.00	2 Weeks

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Related CAS #

No Data

Synonym

Citrinin; NSC 186; NSC186; NSC-186; (–)-Citrinin; CTN

IUPAC/Chemical Name

(3R,4S)-4,6-dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acid

InChi Key

CQIUKKVOEOPUDV-FSPLSTOPSA-N

InChi Code

InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m0/s1

SMILES Code

O=C1C(C)=C2[C@@H](C)[C@H](C)OC=C2C(O)=C1C(O)=O

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 250.25 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.

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

1: Frank HK. Citrinin. Z Ernahrungswiss. 1992 Sep;31(3):164-77. doi: 10.1007/BF01611139. PMID: 1441645. 2: de Menezes APM, Aguiar RPS, Santos JVO, Sarkar C, Islam MT, Braga AL, Hasan MM, da Silva FCC, Sharifi-Rad J, Dey A, Calina D, Melo-Cavalcante AAC, Sousa JMC. Citrinin as a potential anti-cancer therapy: A comprehensive review. Chem Biol Interact. 2023 Aug 25;381:110561. doi: 10.1016/j.cbi.2023.110561. Epub 2023 May 23. PMID: 37230156. 3: GORE TS, PANSE TB, VENKATARAMAN K. Citrinin. Nature. 1946 Mar 16;157:333. doi: 10.1038/157333a0. PMID: 21019852. 4: Kamle M, Mahato DK, Gupta A, Pandhi S, Sharma N, Sharma B, Mishra S, Arora S, Selvakumar R, Saurabh V, Dhakane-Lad J, Kumar M, Barua S, Kumar A, Gamlath S, Kumar P. Citrinin Mycotoxin Contamination in Food and Feed: Impact on Agriculture, Human Health, and Detection and Management Strategies. Toxins (Basel). 2022 Jan 23;14(2):85. doi: 10.3390/toxins14020085. PMID: 35202113; PMCID: PMC8874403. 5: Ali N, Degen GH. Citrinin biomarkers: a review of recent data and application to human exposure assessment. Arch Toxicol. 2019 Nov;93(11):3057-3066. doi: 10.1007/s00204-019-02570-y. Epub 2019 Sep 10. PMID: 31501918. 6: Chen Y, Ye Y, Wu H, Wu Z, Li P, Fu Y, Sun Y, Wang X, Wang J, Yang Z, Zhou E. Citrinin stimulated heterophil extracellular trap formation in chickens. Mol Immunol. 2022 Dec;152:27-34. doi: 10.1016/j.molimm.2022.09.014. Epub 2022 Oct 14. PMID: 36244215. 7: Zhang H, Ahima J, Yang Q, Zhao L, Zhang X, Zheng X. A review on citrinin: Its occurrence, risk implications, analytical techniques, biosynthesis, physiochemical properties and control. Food Res Int. 2021 Mar;141:110075. doi: 10.1016/j.foodres.2020.110075. Epub 2020 Dec 31. PMID: 33641962. 8: de Oliveira Filho JWG, Andrade TJADS, de Lima RMT, Dos Reis AC, Silva DHS, Santos JVO, de Menezes APM, da Mata AMO, Dias ACS, de Alencar MVOB, Paz MFCJ, Moreno LCGEAI, Islam MT, Mubarak MS, Sousa JMCE, Melo Cavalcante AAC. Citrinin against breast cancer: A cytogenotoxicological study. Phytother Res. 2021 Jan;35(1):504-516. doi: 10.1002/ptr.6830. Epub 2020 Aug 31. PMID: 32869401. 9: Chan WH. Citrinin induces apoptosis in mouse embryonic stem cells. IUBMB Life. 2008 Mar;60(3):171-9. doi: 10.1002/iub.30. PMID: 18380009. 10: Flajs D, Peraica M. Toxicological properties of citrinin. Arh Hig Rada Toksikol. 2009 Dec;60(4):457-64. doi: 10.2478/10004-1254-60-2009-1992. PMID: 20061247. 11: Ali N. Co-occurrence of citrinin and ochratoxin A in rice in Asia and its implications for human health. J Sci Food Agric. 2018 Apr;98(6):2055-2059. doi: 10.1002/jsfa.8667. Epub 2017 Oct 9. PMID: 28898415. 12: Ji H, Zhao L, Lv K, Zhang Y, Gao H, Gong Q, Yu W. Citrinin Is a Potential Quorum Sensing Inhibitor against Pseudomonas aeruginosa. Mar Drugs. 2023 May 12;21(5):296. doi: 10.3390/md21050296. PMID: 37233490; PMCID: PMC10221562. 13: Li X, Tian L, Oiao X, Ye L, Wang H, Wang M, Sang J, Tian F, Ge RS, Wang Y. Citrinin inhibits the function of Leydig cells in male rats in prepuberty. Ecotoxicol Environ Saf. 2023 Mar 1;252:114568. doi: 10.1016/j.ecoenv.2023.114568. Epub 2023 Jan 23. PMID: 36696728. 14: Wei J, Chen X, Ge Y, Yin Q, Wu X, Tang J, Zhang Z, Wu B. Citrinin Monomer, Trimer, and Tetracyclic Alkaloid Derivatives from the Hydrothermal Vent- Associated Fungus Penicillium citrinum TW132-59. J Org Chem. 2022 Oct 7;87(19):13270-13279. doi: 10.1021/acs.joc.2c01856. Epub 2022 Sep 21. PMID: 36131357. 15: de Oliveira Filho JWG, Islam MT, Ali ES, Uddin SJ, Santos JVO, de Alencar MVOB, Júnior ALG, Paz MFCJ, de Brito MDRM, E Sousa JMC, Shaw S, de Medeiros MDGF, Dantas SMMM, Rolim HML, Ferreira PMP, Kamal MA, Pieczynska MD, Das N, Gupta VK, Mocan A, Dos Santos Andrade TJA, Singh BN, Mishra SK, Atanasov AG, Melo-Cavalcante AAC. A comprehensive review on biological properties of citrinin. Food Chem Toxicol. 2017 Dec;110:130-141. doi: 10.1016/j.fct.2017.10.002. Epub 2017 Oct 7. PMID: 28993214. 16: Citrinin. IARC Monogr Eval Carcinog Risk Chem Hum. 1986;40:67-82. PMID: 3473017. 17: Jiang WJ, Liu W, Li YH, Jiang H, Xu YN, Kim NH. Citrinin impairs pig oocyte maturation by inducing oxidative stress and apoptosis. Toxicon. 2022 Jan 15;205:84-90. doi: 10.1016/j.toxicon.2021.11.124. Epub 2021 Dec 3. PMID: 34871670. 18: Degen GH, Reinders J, Kraft M, Völkel W, Gerull F, Burghardt R, Sievering S, Engelmann J, Chovolou Y, Hengstler JG, Fromme H. Citrinin Exposure in Germany: Urine Biomarker Analysis in Children and Adults. Toxins (Basel). 2022 Dec 30;15(1):26. doi: 10.3390/toxins15010026. Erratum in: Toxins (Basel). 2023 May 06;15(5): PMID: 36668846; PMCID: PMC9862099. 19: Magro M, Moritz DE, Bonaiuto E, Baratella D, Terzo M, Jakubec P, Malina O, Čépe K, Aragao GMF, Zboril R, Vianello F. Citrinin mycotoxin recognition and removal by naked magnetic nanoparticles. Food Chem. 2016 Jul 15;203:505-512. doi: 10.1016/j.foodchem.2016.01.147. Epub 2016 Feb 17. PMID: 26948644. 20: Farawahida AH, Palmer J, Flint S. Monascus spp. and citrinin: Identification, selection of Monascus spp. isolates, occurrence, detection and reduction of citrinin during the fermentation of red fermented rice. Int J Food Microbiol. 2022 Oct 16;379:109829. doi: 10.1016/j.ijfoodmicro.2022.109829. Epub 2022 Jul 8. PMID: 35863149.

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