Deepoxy-deoxynivalenol | CAS#88054-24-4

MedKoo Cat#: 581382 | Name: Deepoxy-deoxynivalenol

Description:

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

Deepoxy-deoxynivalenol is Metabolite of deoxynivalenol. Deepoxydeoxynivalenol is a macrocyclic polyol compound for proteomics research. Environmental contaminants; Food contaminants.

Chemical Structure

Deepoxy-deoxynivalenol

CAS#88054-24-4

Theoretical Analysis

MedKoo Cat#: 581382

Name: Deepoxy-deoxynivalenol

CAS#: 88054-24-4

Chemical Formula: C15H20O5

Exact Mass: 280.1311

Molecular Weight: 280.32

Elemental Analysis: C, 64.27; H, 7.19; O, 28.54

Price and Availability

Size	Price	Availability	Quantity

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Deepoxy-deoxynivalenol; DOM-1; DOM-I;

IUPAC/Chemical Name

(2S,3R,5S,5aS,6S,9aR)-3,6-dihydroxy-5a-(hydroxymethyl)-5,8-dimethyl-10-methylene-2,3,4,5,5a,9a-hexahydro-2,5-methanobenzo[b]oxepin-7(6H)-one

InChi Key

ZACLXWTWERGCLX-RXDVDPODSA-N

InChi Code

InChI=1S/C15H20O5/c1-7-4-10-15(6-16,13(19)11(7)18)14(3)5-9(17)12(20-10)8(14)2/h4,9-10,12-13,16-17,19H,2,5-6H2,1,3H3/t9-,10-,12+,13-,14+,15+/m1/s1

SMILES Code

C=1(C)C(=O)[C@@H](O)[C@@]2([C@@H](C1)O[C@@H]1[C@H](O)C[C@@]2(C)C1=C)CO

Appearance

To be determined

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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 280.32 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: Pierron A, Bracarense APFL, Cossalter AM, Laffitte J, Schwartz-Zimmermann HE, Schatzmayr G, Pinton P, Moll WD, Oswald IP. Deepoxy-deoxynivalenol retains some immune-modulatory properties of the parent molecule deoxynivalenol in piglets. Arch Toxicol. 2018 Aug 31. doi: 10.1007/s00204-018-2293-x. [Epub ahead of print] PubMed PMID: 30171291. 2: Zhu Y, Hassan YI, Shao S, Zhou T. Employing immuno-affinity for the analysis of various microbial metabolites of the mycotoxin deoxynivalenol. J Chromatogr A. 2018 Jun 29;1556:81-87. doi: 10.1016/j.chroma.2018.04.067. Epub 2018 May 1. PubMed PMID: 29731291. 3: Bryła M, Waśkiewicz A, Ksieniewicz-Woźniak E, Szymczyk K, Jędrzejczak R. Modified Fusarium Mycotoxins in Cereals and Their Products-Metabolism, Occurrence, and Toxicity: An Updated Review. Molecules. 2018 Apr 20;23(4). pii: E963. doi: 10.3390/molecules23040963. Review. PubMed PMID: 29677133. 4: Novak B, Vatzia E, Springler A, Pierron A, Gerner W, Reisinger N, Hessenberger S, Schatzmayr G, Mayer E. Bovine Peripheral Blood Mononuclear Cells Are More Sensitive to Deoxynivalenol Than Those Derived from Poultry and Swine. Toxins (Basel). 2018 Apr 11;10(4). pii: E152. doi: 10.3390/toxins10040152. PubMed PMID: 29641442; PubMed Central PMCID: PMC5923318. 5: Vidal A, Claeys L, Mengelers M, Vanhoorne V, Vervaet C, Huybrechts B, De Saeger S, De Boevre M. Humans significantly metabolize and excrete the mycotoxin deoxynivalenol and its modified form deoxynivalenol-3-glucoside within 24 hours. Sci Rep. 2018 Mar 27;8(1):5255. doi: 10.1038/s41598-018-23526-9. PubMed PMID: 29588479; PubMed Central PMCID: PMC5869592. 6: Papageorgiou M, Wells L, Williams C, White K, De Santis B, Liu Y, Debegnach F, Miano B, Moretti G, Greetham S, Brera C, Atkin SL, Hardie LJ, Sathyapalan T. Assessment of Urinary Deoxynivalenol Biomarkers in UK Children and Adolescents. Toxins (Basel). 2018 Jan 23;10(2). pii: E50. doi: 10.3390/toxins10020050. PubMed PMID: 29360781; PubMed Central PMCID: PMC5848151. 7: Flores-Flores ME, González-Peñas E. Short communication: Analysis of mycotoxins in Spanish milk. J Dairy Sci. 2018 Jan;101(1):113-117. doi: 10.3168/jds.2017-13290. Epub 2017 Oct 18. PubMed PMID: 29055539. 8: Guerrero-Netro HM, Estienne A, Chorfi Y, Price CA. The mycotoxin metabolite deepoxy- deoxynivalenol increases apoptosis and decreases steroidogenesis in bovine ovarian theca cells. Biol Reprod. 2017 Nov 1;97(5):746-757. doi: 10.1093/biolre/iox127. PubMed PMID: 29045588. 9: De Boevre M, Van Poucke C, Ediage EN, Vanderputten D, Van Landschoot A, De Saeger S. Ultra-High-Performance Supercritical Fluid Chromatography as a Separation Tool for Fusarium Mycotoxins and Their Modified Forms. J AOAC Int. 2018 May 1;101(3):627-632. doi: 10.5740/jaoacint.17-0336. Epub 2017 Oct 2. PubMed PMID: 28964272. 10: Vidal A, Sanchis V, Ramos AJ, Marín S. Effect of xylanase and α-amylase on DON and its conjugates during the breadmaking process. Food Res Int. 2017 Nov;101:139-147. doi: 10.1016/j.foodres.2017.08.021. Epub 2017 Sep 1. PubMed PMID: 28941676. 11: Mayer E, Novak B, Springler A, Schwartz-Zimmermann HE, Nagl V, Reisinger N, Hessenberger S, Schatzmayr G. Effects of deoxynivalenol (DON) and its microbial biotransformation product deepoxy-deoxynivalenol (DOM-1) on a trout, pig, mouse, and human cell line. Mycotoxin Res. 2017 Nov;33(4):297-308. doi: 10.1007/s12550-017-0289-7. Epub 2017 Jul 24. PubMed PMID: 28741250; PubMed Central PMCID: PMC5644741. 12: Schwartz-Zimmermann HE, Hametner C, Nagl V, Fiby I, Macheiner L, Winkler J, Dänicke S, Clark E, Pestka JJ, Berthiller F. Glucuronidation of deoxynivalenol (DON) by different animal species: identification of iso-DON glucuronides and iso-deepoxy-DON glucuronides as novel DON metabolites in pigs, rats, mice, and cows. Arch Toxicol. 2017 Dec;91(12):3857-3872. doi: 10.1007/s00204-017-2012-z. Epub 2017 Jun 21. Erratum in: Arch Toxicol. 2018 Oct;92(10):3245-3246. PubMed PMID: 28638985; PubMed Central PMCID: PMC5719127. 13: Vanhoutte I, De Mets L, De Boevre M, Uka V, Di Mavungu JD, De Saeger S, De Gelder L, Audenaert K. Microbial Detoxification of Deoxynivalenol (DON), Assessed via a Lemna minor L. Bioassay, through Biotransformation to 3-epi-DON and 3-epi-DOM-1. Toxins (Basel). 2017 Feb 13;9(2). pii: E63. doi: 10.3390/toxins9020063. PubMed PMID: 28208799; PubMed Central PMCID: PMC5331442. 14: Föllmann W, Ali N, Blaszkewicz M, Degen GH. Biomonitoring of Mycotoxins in Urine: Pilot Study in Mill Workers. J Toxicol Environ Health A. 2016;79(22-23):1015-1025. PubMed PMID: 27924714. 15: Springler A, Hessenberger S, Reisinger N, Kern C, Nagl V, Schatzmayr G, Mayer E. Deoxynivalenol and its metabolite deepoxy-deoxynivalenol: multi-parameter analysis for the evaluation of cytotoxicity and cellular effects. Mycotoxin Res. 2017 Feb;33(1):25-37. doi: 10.1007/s12550-016-0260-z. Epub 2016 Nov 5. PubMed PMID: 27817099; PubMed Central PMCID: PMC5239812. 16: Flores-Flores ME, González-Peñas E. An LC-MS/MS method for multi-mycotoxin quantification in cow milk. Food Chem. 2017 Mar 1;218:378-385. doi: 10.1016/j.foodchem.2016.09.101. Epub 2016 Sep 16. PubMed PMID: 27719924. 17: Springler A, Hessenberger S, Schatzmayr G, Mayer E. Early Activation of MAPK p44/42 Is Partially Involved in DON-Induced Disruption of the Intestinal Barrier Function and Tight Junction Network. Toxins (Basel). 2016 Sep 8;8(9). pii: E264. doi: 10.3390/toxins8090264. PubMed PMID: 27618100; PubMed Central PMCID: PMC5037490. 18: Pierron A, Mimoun S, Murate LS, Loiseau N, Lippi Y, Bracarense AP, Schatzmayr G, He JW, Zhou T, Moll WD, Oswald IP. Microbial biotransformation of DON: molecular basis for reduced toxicity. Sci Rep. 2016 Jul 6;6:29105. doi: 10.1038/srep29105. PubMed PMID: 27381510; PubMed Central PMCID: PMC4933977. 19: Ali N, Blaszkewicz M, Degen GH. Assessment of deoxynivalenol exposure among Bangladeshi and German adults by a biomarker-based approach. Toxicol Lett. 2016 Sep 6;258:20-28. doi: 10.1016/j.toxlet.2016.06.006. Epub 2016 Jun 22. PubMed PMID: 27298273. 20: Schwartz-Zimmermann HE, Fruhmann P, Dänicke S, Wiesenberger G, Caha S, Weber J, Berthiller F. Metabolism of deoxynivalenol and deepoxy-deoxynivalenol in broiler chickens, pullets, roosters and turkeys. Toxins (Basel). 2015 Nov 12;7(11):4706-29. doi: 10.3390/toxins7114706. PubMed PMID: 26569307; PubMed Central PMCID: PMC4663529.