641-38-3 Usage
Description
3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE, also known as Alternariol, is a benzochromenone belonging to the dibenzo-pyrones chemical group. It is a mycotoxin produced by Alternaria molds, which are common mycoflora infecting small grain cereals worldwide. Alternariol is characterized by its cytotoxic, fetotoxic, teratogenic, mutagenic, and genotoxic properties. It is also known to induce cytochrome P450 1A1 expression and apoptosis in mouse hepatoma cells.
Uses
Used in Analytical Chemistry:
3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE is used as a calibration standard in reverse phase high-performance liquid chromatography (HPLC) and UV-spectrum analysis for its accurate and reliable measurements.
Used in Food Science:
3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE is used to spike wholemeal wheat flour for wet baking studies, allowing researchers to investigate the effects of Alternariol on the baking process and the quality of the final product.
Used in Environmental Studies:
3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE is used in the study of indoor air, soil, and plants, as it is a mycotoxin present in these environments. This helps in understanding the impact of Alternariol on human health and the environment.
Used in Pharmaceutical Research:
3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE is used as a research compound in the development of new drugs and therapies, particularly in the field of cancer treatment, due to its cytotoxic properties.
Used in Agriculture:
3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE is used in the study of Alternaria species, which are common mycoflora infecting small grain cereals. This helps in developing strategies to control the growth of these molds and reduce the contamination of cereals with Alternariol.
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.
references
[1] tiemann u, tomek w, schneider f, et al. the mycotoxins alternariol and alternariol methyl ether negatively affect progesterone synthesis in porcine granulosa cells in vitro[j]. toxicology letters, 2009, 186(2): 139-145.[2] sderhll k, svensson e, unestam t. light inhibits the production of alternariol and alternariol monomethyl ether in alternaria alternata[j]. applied and environmental microbiology, 1978, 36(5): 655-657.[3] schreck i, deigendesch u, burkhardt b, et al. the alternaria mycotoxins alternariol and alternariol methyl ether induce cytochrome p450 1a1 and apoptosis in murine hepatoma cells dependent on the aryl hydrocarbon receptor[j]. archives of toxicology, 2012, 86(4): 625-632.
Check Digit Verification of cas no
The CAS Registry Mumber 641-38-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,4 and 1 respectively; the second part has 2 digits, 3 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 641-38:
(5*6)+(4*4)+(3*1)+(2*3)+(1*8)=63
63 % 10 = 3
So 641-38-3 is a valid CAS Registry Number.
InChI:InChI=1/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
641-38-3Relevant articles and documents
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Freemann
, p. 719,720, 721 (1966)
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Synthesis of alternariol through an intramolecular biaryl coupling reaction using palladium reagent
Abe, Hitoshi,Fukumoto, Tomoko,Takeuchi, Yasuo,Harayamac, Takashi
, p. 265 - 271 (2008/09/17)
The facile synthesis of altemariol was accomplished through an intramolecular biaryl coupling reaction of the phenyl benzoate derivative, which was prepared by the simple esterification of the corresponding phenol and benzoic acid using a palladium reagen
