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A1312

Sigma-Aldrich

Alternariol from Alternaria sp.

~96%

Synonym(s):

3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one

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About This Item

Empirical Formula (Hill Notation):
C14H10O5
CAS Number:
641-38-3
Molecular Weight:
258.23
MDL number:
MFCD00133068
UNSPSC Code:
12352200
PubChem Substance ID:
24890529
NACRES:
NA.77

assay

~96%

Quality Level

200

form

powder

storage temp.

2-8°C

SMILES string

Cc1cc(O)cc2OC(=O)c3c(O)cc(O)cc3-c12

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

InChI key

CEBXXEKPIIDJHL-UHFFFAOYSA-N

General description

Alternariol belongs to the dibenzo-pyrones chemical group. It is a mycotoxin present in indoor air, soil and plants.

Application

Alternariol from Alternaria sp. may be used as a calibration standard in reverse phase high-performance liquid chromatography (HPLC) and UV-spectrum analysis. It may also be used to spike wholemeal wheat flour for wet baking studies

Biochem/physiol Actions

Alternaria mycotoxins are generally associated with undried food grains post-harvest. The disease caused by Alternaria mycotoxin results in a discolored halo in fruits and spotting in leaves. Alternariol (AOH) is cytotoxic and fetotoxic to microbes and mammalian cells. AOH displays inhibitory effect on cell proliferation and has estrogenic functionality.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 1 Inhalation - Acute Tox. 2 Dermal - Acute Tox. 2 Oral

Storage Class

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Alternaria mycotoxins in food and feed: an overview
EscrivaL, et al.
Journal of Food Quality, 2017 (2017)
David Siegel et al.
Journal of agricultural and food chemistry, 58(17), 9622-9630 (2010-08-07)
The stability of the Alternaria mycotoxins alternariol, alternariol monomethyl ether, and altenuene upon bread baking was investigated by model experiments using a spiked wholemeal wheat flour matrix. For alternariol and alternariol monomethyl ether, but not for altenuene, degradation products, formed
Detection of alternariol in Estonian grain samples
Kutt ML, et al.
Agronomy Research , 8(Special II), 317-322 (2010)
A Solhaug et al.
Toxicology letters, 219(1), 8-17 (2013-03-05)
The mycotoxin alternariol (AOH), a frequent contaminant in fruit and cereal products, is known to induce DNA damage with subsequent cell cycle arrest. Here we elucidated the effects of AOH on stages of cell cycle progression using the RAW 264.7
Stefanie C Fleck et al.
Toxicology letters, 214(1), 27-32 (2012-08-21)
Altertoxin II (ATX II) is one of the several mycotoxins produced by Alternaria fungi. It has a perylene quinone structure and is highly mutagenic in Ames Salmonella typhimurium, but its mutagenicity in mammalian cells has not been studied before. Here
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