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MedKoo Cat#: 540009 | Name: Alternariol
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Description:

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

Alternariol is a mycotoxin, topoisomerase I and II inhibitor and potential ER agonist found in Alternaria. It occurs naturally in foodstuffs and is frequently found as contaminant in fruit and grain products.

Chemical Structure

Alternariol
Alternariol
CAS#641-38-3

Theoretical Analysis

MedKoo Cat#: 540009

Name: Alternariol

CAS#: 641-38-3

Chemical Formula: C14H10O5

Exact Mass: 258.0528

Molecular Weight: 258.23

Elemental Analysis: C, 65.12; H, 3.90; O, 30.98

Price and Availability

Size Price Availability Quantity
1mg USD 285.00 2 Weeks
5mg USD 650.00 2 Weeks
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Related CAS #
23452-05-3 (monomethyl ether) 641-38-3
Synonym
Alternariol; AOH; NSC 638263; NSC638263; NSC-638263
IUPAC/Chemical Name
3,7,9-trihydroxy-1-methyl-6H-benzo[c]chromen-6-one
InChi Key
CEBXXEKPIIDJHL-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H10O5/c1-6-2-7(15)5-11-12(6)9-3-8(16)4-10(17)13(9)14(18)19-11/h2-5,15-17H,1H3
SMILES Code
O=C1C2=C(O)C=C(O)C=C2C3=C(C)C=C(O)C=C3O1
Appearance
Solid powder
Purity
>95% (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

Preparing Stock Solutions

The following data is based on the product molecular weight 258.23 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
1: Lou J, Yu R, Wang X, Mao Z, Fu L, Liu Y, Zhou L. Alternariol 9-methyl ether from the endophytic fungus Alternaria sp. Samif01 and its bioactivities. Braz J Microbiol. 2016 Jan-Mar;47(1):96-101. doi: 10.1016/j.bjm.2015.11.004. Epub 2016 Jan 27. PubMed PMID: 26887231; PubMed Central PMCID: PMC4822747. 2: Simon H, Hoffmann G, Hübner F, Humpf HU, Karst U. Electrochemical simulation of metabolic reactions of the secondary fungal metabolites alternariol and alternariol methyl ether. Anal Bioanal Chem. 2016 Apr;408(10):2471-83. doi: 10.1007/s00216-016-9344-z. Epub 2016 Feb 11. PubMed PMID: 26869346. 3: Dellafiora L, Dall'Asta C, Cruciani G, Galaverna G, Cozzini P. Molecular modelling approach to evaluate poisoning of topoisomerase I by alternariol derivatives. Food Chem. 2015 Dec 15;189:93-101. doi: 10.1016/j.foodchem.2015.02.083. Epub 2015 Feb 24. PubMed PMID: 26190606. 4: Soukup ST, Kohn BN, Pfeiffer E, Geisen R, Metzler M, Bunzel M, Kulling SE. Sulfoglucosides as Novel Modified Forms of the Mycotoxins Alternariol and Alternariol Monomethyl Ether. J Agric Food Chem. 2016 Nov 23;64(46):8892-8901. Epub 2016 Nov 15. PubMed PMID: 27776211. 5: Fernández-Blanco C, Font G, Ruiz MJ. Role of quercetin on Caco-2 cells against cytotoxic effects of alternariol and alternariol monomethyl ether. Food Chem Toxicol. 2016 Mar;89:60-6. doi: 10.1016/j.fct.2016.01.011. Epub 2016 Jan 21. PubMed PMID: 26802676. 6: Tiessen C, Ellmer D, Mikula H, Pahlke G, Warth B, Gehrke H, Zimmermann K, Heiss E, Fröhlich J, Marko D. Impact of phase I metabolism on uptake, oxidative stress and genotoxicity of the emerging mycotoxin alternariol and its monomethyl ether in esophageal cells. Arch Toxicol. 2017 Mar;91(3):1213-1226. doi: 10.1007/s00204-016-1801-0. Epub 2016 Jul 15. PubMed PMID: 27422292; PubMed Central PMCID: PMC5316404. 7: Estiarte N, Crespo-Sempere A, Marín S, Sanchis V, Ramos AJ. Effect of 1-methylcyclopropene on the development of black mold disease and its potential effect on alternariol and alternariol monomethyl ether biosynthesis on tomatoes infected with Alternaria alternata. Int J Food Microbiol. 2016 Nov 7;236:74-82. doi: 10.1016/j.ijfoodmicro.2016.07.001. Epub 2016 Jul 4. PubMed PMID: 27454782. 8: Graf E, Schmidt-Heydt M, Geisen R. HOG MAP kinase regulation of alternariol biosynthesis in Alternaria alternata is important for substrate colonization. Int J Food Microbiol. 2012 Jul 16;157(3):353-9. doi: 10.1016/j.ijfoodmicro.2012.06.004. Epub 2012 Jun 9. PubMed PMID: 22726725. 9: Liu Y, Rychlik M. Biosynthesis of seven carbon-13 labeled Alternaria toxins including altertoxins, alternariol, and alternariol methyl ether, and their application to a multiple stable isotope dilution assay. Anal Bioanal Chem. 2015 Feb;407(5):1357-69. doi: 10.1007/s00216-014-8307-5. Epub 2015 Jan 11. PubMed PMID: 25577349. 10: Hildebrand AA, Kohn BN, Pfeiffer E, Wefers D, Metzler M, Bunzel M. Conjugation of the mycotoxins alternariol and alternariol monomethyl ether in tobacco suspension cells. J Agric Food Chem. 2015 May 20;63(19):4728-36. doi: 10.1021/acs.jafc.5b00806. Epub 2015 May 7. PubMed PMID: 25912034. 11: Abou-Hany RA, Urraca JL, Descalzo AB, Gómez-Arribas LN, Moreno-Bondi MC, Orellana G. Tailoring molecularly imprinted polymer beads for alternariol recognition and analysis by a screening with mycotoxin surrogates. J Chromatogr A. 2015 Dec 18;1425:231-9. doi: 10.1016/j.chroma.2015.11.055. Epub 2015 Nov 28. PubMed PMID: 26632518. 12: Juan-García A, Juan C, Manyes L, Ruiz MJ. Binary and tertiary combination of alternariol, 3-acetyl-deoxynivalenol and 15-acetyl-deoxynivalenol on HepG2 cells: Toxic effects and evaluation of degradation products. Toxicol In Vitro. 2016 Aug;34:264-73. doi: 10.1016/j.tiv.2016.04.016. Epub 2016 Apr 27. PubMed PMID: 27131905. 13: Fleck SC, Sauter F, Pfeiffer E, Metzler M, Hartwig A, Köberle B. DNA damage and repair kinetics of the Alternaria mycotoxins alternariol, altertoxin II and stemphyltoxin III in cultured cells. Mutat Res Genet Toxicol Environ Mutagen. 2016 Mar;798-799:27-34. doi: 10.1016/j.mrgentox.2016.02.001. Epub 2016 Feb 8. PubMed PMID: 26994491. 14: Fernández-Blanco C, Juan-García A, Juan C, Font G, Ruiz MJ. Alternariol induce toxicity via cell death and mitochondrial damage on Caco-2 cells. Food Chem Toxicol. 2016 Feb;88:32-9. doi: 10.1016/j.fct.2015.11.022. Epub 2015 Dec 9. PubMed PMID: 26683312. 15: Saha D, Fetzner R, Burkhardt B, Podlech J, Metzler M, Dang H, Lawrence C, Fischer R. Identification of a polyketide synthase required for alternariol (AOH) and alternariol-9-methyl ether (AME) formation in Alternaria alternata. PLoS One. 2012;7(7):e40564. doi: 10.1371/journal.pone.0040564. Epub 2012 Jul 6. PubMed PMID: 22792370; PubMed Central PMCID: PMC3391263. 16: Solhaug A, Wisbech C, Christoffersen TE, Hult LO, Lea T, Eriksen GS, Holme JA. The mycotoxin alternariol induces DNA damage and modify macrophage phenotype and inflammatory responses. Toxicol Lett. 2015 Nov 19;239(1):9-21. doi: 10.1016/j.toxlet.2015.08.1107. Epub 2015 Sep 2. PubMed PMID: 26341179. 17: Broggi L, Reynoso C, Resnik S, Martinez F, Drunday V, Bernal AR. Occurrence of alternariol and alternariol monomethyl ether in beverages from the Entre Rios Province market, Argentina. Mycotoxin Res. 2013 Feb;29(1):17-22. doi: 10.1007/s12550-012-0147-6. Epub 2012 Oct 19. PubMed PMID: 23334721. 18: Ackermann Y, Curtui V, Dietrich R, Gross M, Latif H, Märtlbauer E, Usleber E. Widespread occurrence of low levels of alternariol in apple and tomato products, as determined by comparative immunochemical assessment using monoclonal and polyclonal antibodies. J Agric Food Chem. 2011 Jun 22;59(12):6360-8. doi: 10.1021/jf201516f. Epub 2011 May 23. PubMed PMID: 21534631. 19: Schwarz C, Kreutzer M, Marko D. Minor contribution of alternariol, alternariol monomethyl ether and tenuazonic acid to the genotoxic properties of extracts from Alternaria alternata infested rice. Toxicol Lett. 2012 Oct 2;214(1):46-52. doi: 10.1016/j.toxlet.2012.08.002. Epub 2012 Aug 13. PubMed PMID: 22906495. 20: Fernández-Blanco C, Font G, Ruiz MJ. Oxidative DNA damage and disturbance of antioxidant capacity by alternariol in Caco-2 cells. Toxicol Lett. 2015 Jun 1;235(2):61-6. doi: 10.1016/j.toxlet.2015.03.013. Epub 2015 Mar 28. PubMed PMID: 25827405.

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