基本情報
- CAS
23452-05-3- 標準SMILES
COc1cc(O)c2c(=O)oc3cc(O)cc(C)c3c2c1- InChIKey
LCSDQFNUYFTXMT-UHFFFAOYSA-N- 分子式
- C15H12O5
- 平均分子量
- 272.25 g/mol
- 単同位体質量
- 272.06847348
概要
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.
名称と識別子
- 優先名称
- Alternariol monomethyl ether
- IUPAC
- 3,7-dihydroxy-9-methoxy-1-methylbenzo[c]chromen-6-one
- 現地名
- アルテルナリオールモノメチルエーテル
- 英語名
- Alternariol monomethyl ether
- 分子式
- C15H12O5
- 分子量
- 272.25
名称と別名
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
名称をさらに表示
アルテルナリオールモノメチルエーテル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
物性
構造計算による物性
- XLogP
- 3.2
- 極性表面積
- 76 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 5
- 回転可能結合数
- 1
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 384
実験および物理化学的性質
SpringerMaterials PropertiesChemical shift
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section150 Ų [M-H]- [CCS Type: TW; Method: calibrated with polyalanine]
物理化学的性質
- 融点
- 270 · 270-273oC (dec.)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- DMSO（微量）、メタノール（微量、加温）
- 外見
- オフホワイトからライトブラウンのソリッド。
- 色
- ホワイトからライトベージュ
- 安定性
- 吸湿性
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
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]
危険有害性情報
Regulatory InformationRegulation (EC) No 178/2002 (amended)
Hazard Classes and Categories
Acute Tox. 2 (100%)
Acute Tox. 4 (100%)
毒性情報
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)
化学と産業
薬理情報
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)
用途と製造
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)
応用分野
使用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.
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