4'-ヒドロキシ-3'-メトキシアセトフェノン
Acetovanillone
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基本情報
- CAS
498-02-2- 標準SMILES
COc1cc(C(C)=O)ccc1O- InChIKey
DFYRUELUNQRZTB-UHFFFAOYSA-N- 分子式
- C9H10O3
- 平均分子量
- 166.17 g/mol
- 単同位体質量
- 166.06299418
概要
Apocynin is an aromatic ketone that is 1-phenylethanone substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antirheumatic drug, a peripheral nervous system drug, an EC 1.6.3.1. [NAD(P)H oxidase (H2O2-forming)] inhibitor and a plant metabolite. It is a member of acetophenones, a methyl ketone and an aromatic ketone.
名称と識別子
- 優先名称
- Acetovanillone
- IUPAC
- 1-(4-hydroxy-3-methoxyphenyl)ethanone
- 現地名
- 4'-ヒドロキシ-3'-メトキシアセトフェノン
- 英語名
- Acetovanillone
- 分子式
- C9H10O3
- 分子量
- 166.17
名称と別名
Acetovanilloneapocynin498-02-24'-Hydroxy-3'-methoxyacetophenone1-(4-Hydroxy-3-methoxyphenyl)ethanoneAcetoguaiaconeApocynine4-Acetyl-2-methoxyphenolAcetoguaiacon1-(4-hydroxy-3-methoxyphenyl)ethan-1-oneEthanone, 1-(4-hydroxy-3-methoxyphenyl)-4-Hydroxy-3-methoxyphenyl methyl ketone
名称をさらに表示
4'-ヒドロキシ-3'-メトキシアセトフェノンアセトバニロンアポシニンアセトバニルロン4′-ヒドロキシ-3′-メトキシアセトフェノン4-HYDROXY-3-METHOXYACETOPHENONEACETOVANILLONApocynin (Acetovanillone)3'-METHOXY-4'-HYDROXYACETOPHENONE
B6J7B9UDTRNSC-209524DTXSID7060097CHEBI:2781RefChem:552432DTXCID1040740207-854-5Acetovanilone
データベース識別子
- CAS
498-02-2- PubChem CID
- 2214
物性
構造計算による物性補完中
- XLogP
- 0.5
- 極性表面積
- 46.5 Ų
- 水素結合供与体数
- 1
- 水素結合受容体数
- 3
- 回転可能結合数
- 2
- 重原子数
- 12
- 形式電荷
- 0
- 複雑度
- 167
実験および物理化学的性質
DrugsPharmaceuticals -> Listed in ZINC15
FragrancesFragrance Ingredient (4'-Hydroxy-3'-methoxyacetophenone) -> IFRA transparency List
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound
物理化学的性質
- 融点
- 112 · 112-115 °C (lit.)
- 沸点
- 263 · 263-265 °C/17 mmHg (lit.)
- 比重(密度)
- 1.1708 · 1.1708 (rough estimate)
- 屈折率
- 1.5101 · 1.5101 (estimate)
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- アセトニトリル（微量）、クロロホルム（微量）、酢酸エチル（微量）、メタン
- 酸解離定数(Pka)
- 8.18 · 8.18±0.18(Predicted)
- 外見
- 個体
- 色
- 黄色から茶色
- 臭い (Odor)
- 100 %で。ほのかに甘いバニリン · 100.00%で。ほのかに甘いバニリン
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
This chemical does not meet GHS hazard criteria for 65.7% (94 of 143) of all reports.
Warning
H315 (34.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 143 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Ethanone, 1-(4-hydroxy-3-methoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (34.3%)
安全データ
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- AM8800000
- hs_code
- 29145000
- risk_code
- 36/37/38
- 化審法
- (3)-645
- hazard_code
- Xi
- safety_code
- 26-36
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
用途と製造
Use ClassificationFragrance Ingredients
General Manufacturing InformationEthanone, 1-(4-hydroxy-3-methoxyphenyl)-: ACTIVE
応用分野
使用Acetovanillone is an inhibitor of NADPH oxidase (an enzyme responsible for reactive oxygen species production) and is useful in the treatment of various inflammatory diseases.
一般的な説明Acetovanillone is an aromatic plant ketone, which is a selective inhibitor of NADPH oxidase. It is mainly secreted in the urine of mammals as the corresponding glucuronide conjugate.
調製方法
製造方法Synthetically by methylation of 3,4-Dihydroxyacetophenone. It can also be obtained by Fries rearrangement of guaiacol acetate in the presence of zinc chloride. It can be isolated from the extract of the roots of Indian hemp, Apocynum cannabinum L.
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