3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE

ChemicalBook > CAS DataBase List > 3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE

3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE

Product Name: 3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE
CAS No.: 641-38-3
Chemical Name: 3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE
Synonyms: aoh;NSC 638263;ALTERNARIOL;Alternariol 99%;Alternariol/AOH;13C14-Alternariol;Alternariol 50ug/ml in ACN;alternariol from alternaria sp.;13C14]-Alternariol- 25 μg/Ml in CAN;3,7,9-Trihydroxy-1-methyl-benzo[c]chromen-6-one
CBNumber: CB3297090
Molecular Formula: C14H10O5
Formula Weight: 258.23
MOL File: 641-38-3.mol

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3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE Property

Melting point:: 350°C (rough estimate)
Boiling point:: 321.48°C (rough estimate)
Density: 1.2211 (rough estimate)
refractive index: 1.4560 (estimate)
storage temp.: 2-8°C
solubility: ≤0.5mg/ml in ethanol;30mg/ml in DMSO;30mg/ml in dimethyl formamide
pka: 7.16±0.20(Predicted)
BRN: 244839
Stability:: Hygroscopic

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Safety

Hazard Codes: T+
Risk Statements: 26/27/28
Safety Statements: 28-36/37/39-45
RIDADR: UN 3462 6.1/PG 1
WGK Germany: 3
RTECS: HP8757000
HazardClass: 6.1(b)
PackingGroup: III
HS Code: 29322090
Toxicity: LDLo intraperitoneal in mouse: 100mg/kg

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Precautionary statements

P262Do not get in eyes, on skin, or on clothing.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: A1312
Product name: Alternariol from Alternaria sp.
Purity: ~96%
Packaging: 5mg
Price: $848
Updated: 2024/03/01

Sigma-Aldrich

Product number: 35758
Product name: Alternariol
Purity: analytical standard
Packaging: 100μg
Price: $1080
Updated: 2024/03/01

Cayman Chemical

Product number: 11306
Product name: Alternariol
Purity: ≥95%
Packaging: 1mg
Price: $72
Updated: 2024/03/01

Cayman Chemical

Product number: 11306
Product name: Alternariol
Purity: ≥95%
Packaging: 5mg
Price: $214
Updated: 2024/03/01

TRC

Product number: A575760
Product name: Alternariol
Packaging: 5mg
Price: $195
Updated: 2021/12/16

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3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE Chemical Properties,Usage,Production

Description

Alternariol is a mycotoxin, a toxic secondary fungal metabolite, produced by Alternaria molds. It is cytotoxic, fetotoxic, teratogenic, mutagenic, and genotoxic. It induces cytochrome P450 1A1 expression and apoptosis in mouse hepatoma cells (20-40 μM). Alternariol, whose synthesis is inhibited by light, naturally occurs on fruits, vegetables, and cereals, such as apples, tomatoes, and wheat.

Uses

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

Uses

An alternaria mycotoxin and genotoxin, found in common edible crops. It inhibits the activity of various DNA-topoisomerases, increasing he rate of DNA strand breaks.

Definition

ChEBI: A benzochromenone that is 6H-benzo[c]chromen-6-one which is substituted by a methyl group at position 1 and by hydroxy groups at positions 3, 7, and 9. It is the most important mycotoxin produced by the black mould Alt rnaria species, which are the most common mycoflora infecting small grain cereals worldwide.

Synthesis Reference(s)

The Journal of Organic Chemistry, 70, p. 3275, 2005 DOI: 10.1021/jo050075r

General Description

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

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.

3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE Preparation Products And Raw materials

Raw materials

Preparation Products

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641-38-3, 3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONERelated Search:

Hydroxyecdysone beta-Sitosterol 2-(3,4-Dihydroxyphenyl)-8-(2-O-beta-L-galactopyranosyl-beta-D-glucopyranosyl)-5,7-dihydroxy-4H-1-Benzopyran-4-one alpha-Cyperone hydroxygenkwanin (4E,6E)-1,7-Diphenyl-4,6-heptadien-3-one 2,4-Dihydroxybenzoic acid 2'-METHYL-BIPHENYL-2-CARBOXALDEHYDE Phenyl salicylate Methyl 2,4-dihydroxybenzoate 2-Biphenylcarboxylic acid RESORCINOL MONOBENZOATE 2,4-DIHYDROXY-6-METHYLBENZOIC ACID 3-Hydroxy-5-methylphenyl benzoate alternariol monomethyl ether 2'-Methyl-[1,1'-Biphenyl]-2-Carboxylic Acid 3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE 2-HYDROXY-6-METHYLBENZOIC ACID METHYL ESTER

3,7,9-TRIHYDROXY-1-METHYL-6H-DIBENZO[B,D]PYRAN-6-ONE

aoh

d)pyran-6-one,1-methyl-3,7,9-trihydroxy-6h-dibenzo(

alternariol from alternaria sp.

DIBENZO(B,D)PYRAN-6-ONE,1-METHYL-3,7,9-TRIHYDROXY-

1-Methyl-3,7,9-trihydroxy-6H-dibenzo[b,d]pyran-6-one

Alternariol from Alternaria sp.,3,7,9-Trihydroxy-1-methyl-6H-dibenzo[b,d]pyran-6-one

Alternariol/AOH

Alternariol 99%

NSC 638263

3,7,9-trihydroxy-1-Methyl-6H-benzo[c]chroMen-6-one

ALTERNARIOL

Alternariol 3,7,9-Trihydroxy-1-Methyl-6H-Dibenzo[b,d]Pyran-6-One

3,7,9-Trihydroxy-1-methyl-benzo[c]chromen-6-one

6H-Dibenzo[b,d]pyran-6-one,3,7,9-trihydroxy-1-methyl-

Alternariol 50ug/ml in ACN

13C14-Alternariol

13C14]-Alternariol- 25 μg/Ml in CAN

641-38-3

Inhibitors

Mutagenesis Research Chemicals

Inhibitor