Alternariol monomethyl ether
Basic information
- CAS
23452-05-3- Standard SMILES
COc1cc(O)c2c(=O)oc3cc(O)cc(C)c3c2c1- InChIKey
LCSDQFNUYFTXMT-UHFFFAOYSA-N- Molecular formula
- C15H12O5
- Average molar mass
- 272.25 g/mol
- Monoisotopic mass
- 272.06847348
Overview
Djalonensone is a benzochromenone that is alternariol in which the hydroxy group at position 9 has been converted into the corresponding methyl ether. A natural product found in Chaetomium globosum as well as being one of the two most important compounds belonging to the group of Altenaria mycotoxins. It has a role as a mycotoxin, an antifungal agent and a fungal metabolite. It is an aromatic ether and a benzochromenone. It is functionally related to an alternariol.
Names & identifiers
- Preferred name
- Alternariol monomethyl ether
- IUPAC
- 3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one
- English name
- Alternariol monomethyl ether
- Molecular formula
- C15H12O5
- Molecular weight
- 272.25
Names & synonyms
Alternariol monomethyl etherDjalonensone23452-05-3Alternariol-9-methyl etherAlternariol monomethyletherAlternariol methyl ether3,7-Dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-onealternariol 9-methyl etherBRN 0253553Y79STA800H3,7-Dihydroxy-9-methoxy-1-methyl-6H-dibenzo(b,d)pyran-6-oneCHEBI:141315
Show more names
Alternariol Impurity 6Alternariol monomethyl ether 99%Alternariol monomethyl ether/AME13C15-Alternariol monomethyl etherAlternariol methyl ether in dried downAlternariol monomethyl ether 50ug/ml in ACNalternariol monomethyl ether from*alternaria alteU-{13C15}-Alternariol methyl ester in acetonitrileALTERNARIOL MONOMETHYL ETHER FROMALTERNA RIA ALTERN
3,7-Dihydroxy-9-methoxy-1-methyl-6H-dibenzo[b,d]pyran-6-oneDTXSID301780046H-DIBENZO(b,d)PYRAN-6-ONE, 3,7-DIHYDROXY-9-METHOXY-1-METHYL-NSC-6382626H-Dibenzo[b,d]pyran-6-one, 3,7-dihydroxy-9-methoxy-1-methyl-2-Biphenylcarboxylic acid, 2',3',4'-trihydroxy-5-methoxy-6'-methyl-, delta-lactone3,7-Dihydroxy-9-methoxy-1-methyl-6H-benzo(c)chromen-6-oneRefChem:556178
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 76 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 384
Experimental & physicochemical properties
SpringerMaterials PropertiesChemical shift
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section150 Ų [M-H]- [CCS Type: TW; Method: calibrated with polyalanine]
Physicochemical properties
- Melting point
- 270 · 270-273oC (dec.)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- form
- Off-white to light brown solid.
- color
- White to Light Beige
- Stability
- Hygroscopic
- FDA UNII
- 79 STA800H · Y79STA800H
- Symbol(GHS)
- 8 · GHS08,GHS06
- Signal word
- Danger
- Hazard statements
- 310 · H310-H330-H300-H360
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]
P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and Categories
Acute Tox. 2 (100%)
Acute Tox. 4 (100%)
Toxicology
Health EffectsAltertoxins have been shown to be toxic, genotoxic, mutagenic, and carcinogenic. In particular, they have been associated with esophageal cancer in humans. (A2977, A2979)
Exposure RoutesOral, dermal, inhalation, and parenteral (contaminated drugs). (A3101)
Toxicity Summary
Alternariol methyl ether has been shown to have genotoxic and mutagenic properties. It has demonstrated DNA-damaging activities such as single-strand and double-strand DNA breaks, DNA-intercalating, and DNA cross-linking, as well as induction of DNA repair synthesis and inhibition of DNA replication. These effects are thought to be at least partially due to its ability to bind to the DNA minor groove with high affinity, which inhibits the activity of DNA-acting enzymes such as topoisomerase. (A2977, A2978, A2979)
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Alternariol methyl ether is metabolized by microsomes in the liver, preferentially at aromatic positions. It is also demethylated to alternariol. The products of aromatic hydroxylation are either catechols or hydroquinones, which may form reactive semiquinones and quinones or undergo redox cycling. (A2981)
Uses & manufacturing
UsesAlternariol methyl ether is an altertoxin, which is a mycotoxin of Alternaria fungi. Altertoxins are important contaminants in cereals, vegetables, and fruits, as well as in the ground, on wood or walls. (A2977, A2979)
Applications
UsesAn alternaria mycotoxin and genotoxin, found in common edible crops. It inhibits the activity of various DNA-topoisomerases, increasing he rate of DNA strand breaks.
Additional notes
DefinitionChEBI: Djalonensone is a benzochromenone that is alternariol in which the hydroxy group at position 9 has been converted into the corresponding methyl ether. A natural product found in Chaetomium globosum as well as being one of the two most important compounds belonging to the group of Altenaria mycotoxins. It has a role as an antifungal agent, a fungal metabolite and a mycotoxin. It is a benzochromenone and an aromatic ether. It is functionally related to an alternariol.
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