Ochratoxin A | CAS#303-47-9 | mycotoxin

MedKoo Cat#: 561027 | Name: Ochratoxin A

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Description:

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

Ochratoxin A (OTA) is a mycotoxin produced by several fungal species including Aspergillus ochraceus, A. carbonarius, A. niger, and Penicillium verrucosum. Ochratoxin A is one of the most-abundant food-contaminating mycotoxins.

Chemical Structure

Ochratoxin A

CAS#303-47-9

Theoretical Analysis

MedKoo Cat#: 561027

Name: Ochratoxin A

CAS#: 303-47-9

Chemical Formula: C20H18ClNO6

Exact Mass: 403.0823

Molecular Weight: 403.82

Elemental Analysis: C, 59.49; H, 4.49; Cl, 8.78; N, 3.47; O, 23.77

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 200.00
5mg	USD 440.00
10mg	USD 810.00

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Related CAS #

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Synonym

Ochratoxin A; OTA; Ochratoxin-A;

IUPAC/Chemical Name

((R)-5-chloro-8-hydroxy-3-methyl-1-oxoisochromane-7-carbonyl)-D-phenylalanine

InChi Key

RWQKHEORZBHNRI-MEBBXXQBSA-N

InChi Code

InChI=1S/C20H18ClNO6/c1-10-7-12-14(21)9-13(17(23)16(12)20(27)28-10)18(24)22-15(19(25)26)8-11-5-3-2-4-6-11/h2-6,9-10,15,23H,7-8H2,1H3,(H,22,24)(H,25,26)/t10-,15-/m1/s1

SMILES Code

OC1=C2C(C[C@@H](C)OC2=O)=C(Cl)C=C1C(N[C@@H](C(O)=O)CC3=CC=CC=C3)=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

>2 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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Ochratoxin A (OTA) is a mycotoxin.

In vitro activity:

Nanomolar concentrations of OTA lead to activation of a second member of the MAPK family, namely, c-jun amino-terminal-kinase (JNK) in MDCK-C7 cells but virtually not in MDCK-C11 cells, as determined by kinase assay and Western blot. Furthermore, OTA potentiated the effect of tumor necrosis factor-alpha on JNK activation. In parallel to its effects on JNK, nanomolar OTA induced apoptosis in MDCK-C7 cells but not in MDCK-C11 cells, as determined by DNA fragmentation, DNA ladder formation, and caspase activation. Reference: J Pharmacol Exp Ther. 2000 Jun;293(3):837-44. https://pubmed.ncbi.nlm.nih.gov/10869383/

In vivo activity:

This study observed that administration of a single high dose or multiple lower doses of the carcinogenic nephrotoxin ochratoxin A (OTA) to rats resulted in an increase of the renal cortex endoplasmic reticulum ATP-dependent calcium pump activity. The increase was very rapid, being evident within 10 min of OTA administration and remained elevated for at least 6 hr thereafter. Reference: Biochem Pharmacol. 1992 Oct 6;44(7):1401-9. https://pubmed.ncbi.nlm.nih.gov/1417961/

	Solvent	mg/mL	mM
Solubility
	DMF	10.0	24.76
	DMSO	15.0	37.15
	Ethanol	50.0	123.82
	Ethanol:PBS (pH 7.2) (1:1)	0.5	1.24

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 403.82 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

Formulation protocol:

1. Ou Y, Fu Q, Chen Y, Lin L, Wang J, Wu D, Wu Q, Xie J. Dietary Ochratoxin A Contamination Modulates Oxidative Stress, Inflammation Processes and Causes Fibrosis in in vitro and in vivo Lung Models. Front Biosci (Landmark Ed). 2023 Feb 2;28(2):22. doi: 10.31083/j.fbl2802022. PMID: 36866544. 2. Gekle M, Schwerdt G, Freudinger R, Mildenberger S, Wilflingseder D, Pollack V, Dander M, Schramek H. Ochratoxin A induces JNK activation and apoptosis in MDCK-C7 cells at nanomolar concentrations. J Pharmacol Exp Ther. 2000 Jun;293(3):837-44. PMID: 10869383. 3. Chong X, Rahimtula AD. Alterations in ATP-dependent calcium uptake by rat renal cortex microsomes following ochratoxin A administration in vivo or addition in vitro. Biochem Pharmacol. 1992 Oct 6;44(7):1401-9. doi: 10.1016/0006-2952(92)90542-q. PMID: 1417961. 4. Omar RF, Rahimtula AD, Bartsch H. Role of cytochrome P-450 in ochratoxin A-stimulated lipid peroxidation. J Biochem Toxicol. 1991 Fall;6(3):203-9. doi: 10.1002/jbt.2570060306. PMID: 1770504.

In vitro protocol:

In vivo protocol:

1. Chong X, Rahimtula AD. Alterations in ATP-dependent calcium uptake by rat renal cortex microsomes following ochratoxin A administration in vivo or addition in vitro. Biochem Pharmacol. 1992 Oct 6;44(7):1401-9. doi: 10.1016/0006-2952(92)90542-q. PMID: 1417961. 2. Omar RF, Rahimtula AD, Bartsch H. Role of cytochrome P-450 in ochratoxin A-stimulated lipid peroxidation. J Biochem Toxicol. 1991 Fall;6(3):203-9. doi: 10.1002/jbt.2570060306. PMID: 1770504.

1: Bui-Klimke TR, Wu F. Ochratoxin A and human health risk: a review of the evidence. Crit Rev Food Sci Nutr. 2015;55(13):1860-9. doi: 10.1080/10408398.2012.724480. Review. PubMed PMID: 24874522; PubMed Central PMCID: PMC4247821. 2: Khalesi M. Ochratoxin A in liquorice products - a review. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(12):2086-92. doi: 10.1080/19440049.2015.1094708. Epub 2015 Oct 15. Review. PubMed PMID: 26374697. 3: Heussner AH, Bingle LE. Comparative Ochratoxin Toxicity: A Review of the Available Data. Toxins (Basel). 2015 Oct 22;7(10):4253-82. doi: 10.3390/toxins7104253. Review. PubMed PMID: 26506387; PubMed Central PMCID: PMC4626733. 4: Zhihong L, Kunlun H, Yunbo L. Ochratoxin A and ochratoxin-producing fungi on cereal grain in China: a review. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2015;32(4):461-70. doi: 10.1080/19440049.2014.996787. Epub 2015 Jan 9. Review. PubMed PMID: 25571918. 5: Baggiani C, Giovannoli C, Anfossi L. Man-Made Synthetic Receptors for Capture and Analysis of Ochratoxin A. Toxins (Basel). 2015 Oct 10;7(10):4083-98. doi: 10.3390/toxins7104083. Review. PubMed PMID: 26473924; PubMed Central PMCID: PMC4626722. 6: Vettorazzi A, González-Peñas E, de Cerain AL. Ochratoxin A kinetics: a review of analytical methods and studies in rat model. Food Chem Toxicol. 2014 Oct;72:273-88. doi: 10.1016/j.fct.2014.07.020. Epub 2014 Jul 21. Review. PubMed PMID: 25057808. 7: Ha TH. Recent Advances for the Detection of Ochratoxin A. Toxins (Basel). 2015 Dec 4;7(12):5276-300. doi: 10.3390/toxins7124882. Review. PubMed PMID: 26690216; PubMed Central PMCID: PMC4690132. 8: Vettorazzi A, van Delft J, López de Cerain A. A review on ochratoxin A transcriptomic studies. Food Chem Toxicol. 2013 Sep;59:766-83. doi: 10.1016/j.fct.2013.05.043. Epub 2013 Jun 6. Review. PubMed PMID: 23747715. 9: Limonciel A, Jennings P. A review of the evidence that ochratoxin A is an Nrf2 inhibitor: implications for nephrotoxicity and renal carcinogenicity. Toxins (Basel). 2014 Jan 20;6(1):371-9. doi: 10.3390/toxins6010371. Review. PubMed PMID: 24448208; PubMed Central PMCID: PMC3920267. 10: Malir F, Ostry V, Pfohl-Leszkowicz A, Novotna E. Ochratoxin A: developmental and reproductive toxicity-an overview. Birth Defects Res B Dev Reprod Toxicol. 2013 Dec;98(6):493-502. doi: 10.1002/bdrb.21091. Epub 2014 Jan 6. Review. PubMed PMID: 24395216. 11: Sorrenti V, Di Giacomo C, Acquaviva R, Barbagallo I, Bognanno M, Galvano F. Toxicity of ochratoxin a and its modulation by antioxidants: a review. Toxins (Basel). 2013 Oct 11;5(10):1742-66. doi: 10.3390/toxins5101742. Review. PubMed PMID: 24152986; PubMed Central PMCID: PMC3813909. 12: Bellver Soto J, Fernández-Franzón M, Ruiz MJ, Juan-García A. Presence of ochratoxin A (OTA) mycotoxin in alcoholic drinks from southern European countries: wine and beer. J Agric Food Chem. 2014 Aug 6;62(31):7643-51. doi: 10.1021/jf501737h. Epub 2014 Jul 25. Review. PubMed PMID: 25039256. 13: Ostry V, Malir F, Ruprich J. Producers and important dietary sources of ochratoxin A and citrinin. Toxins (Basel). 2013 Sep 17;5(9):1574-86. doi: 10.3390/toxins5091574. Review. PubMed PMID: 24048364; PubMed Central PMCID: PMC3798874. 14: Zhou WL, Wang YT, Kong WJ, Yang MH, Zhao M, Ou-Yang Z. [Advancement of colloidal gold chromatographic technique in screening of ochratoxin A]. Zhongguo Zhong Yao Za Zhi. 2015 Aug;40(15):2945-51. Review. Chinese. PubMed PMID: 26677691. 15: Rhouati A, Yang C, Hayat A, Marty JL. Aptamers: a promosing tool for ochratoxin A detection in food analysis. Toxins (Basel). 2013 Nov 5;5(11):1988-2008. doi: 10.3390/toxins5111988. Review. PubMed PMID: 24196457; PubMed Central PMCID: PMC3847711. 16: Meulenberg EP. Immunochemical methods for ochratoxin A detection: a review. Toxins (Basel). 2012 Apr;4(4):244-66. doi: 10.3390/toxins4040244. Epub 2012 Apr 13. Review. PubMed PMID: 22606375; PubMed Central PMCID: PMC3347002. 17: Petruzzi L, Sinigaglia M, Corbo MR, Campaniello D, Speranza B, Bevilacqua A. Decontamination of ochratoxin A by yeasts: possible approaches and factors leading to toxin removal in wine. Appl Microbiol Biotechnol. 2014 Aug;98(15):6555-67. doi: 10.1007/s00253-014-5814-4. Epub 2014 May 20. Review. PubMed PMID: 24841121. 18: Malir F, Ostry V, Pfohl-Leszkowicz A, Malir J, Toman J. Ochratoxin A: 50 Years of Research. Toxins (Basel). 2016 Jul 4;8(7). pii: E191. doi: 10.3390/toxins8070191. Review. PubMed PMID: 27384585; PubMed Central PMCID: PMC4963825. 19: Kőszegi T, Poór M. Ochratoxin A: Molecular Interactions, Mechanisms of Toxicity and Prevention at the Molecular Level. Toxins (Basel). 2016 Apr 15;8(4):111. doi: 10.3390/toxins8040111. Review. PubMed PMID: 27092524; PubMed Central PMCID: PMC4848637. 20: Klarić MS, Rašić D, Peraica M. Deleterious effects of mycotoxin combinations involving ochratoxin A. Toxins (Basel). 2013 Nov 1;5(11):1965-87. doi: 10.3390/toxins5111965. Review. PubMed PMID: 24189375; PubMed Central PMCID: PMC3847710.