4'-ヒドロキシ-3',5'-ジメトキシアセトフェノン

Acetosyringone

HCID 17198CAS 2478-38-8
部分構造検索類似構造を探す

基本情報

標準SMILES
COc1cc(C(C)=O)cc(OC)c1O
InChIKey
OJOBTAOGJIWAGB-UHFFFAOYSA-N
分子式
C10H12O4
平均分子量
196.2 g/mol
単同位体質量
196.07355886

概要

Acetosyringone is a member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, a peripheral nervous system drug, an anti-asthmatic drug and a plant metabolite. It is a member of acetophenones, a member of phenols and a dimethoxybenzene.

名称と識別子

優先名称
Acetosyringone
IUPAC
1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
現地名
4'-ヒドロキシ-3',5'-ジメトキシアセトフェノン
英語名
Acetosyringone
分子式
C10H12O4
分子量
196.2

名称と別名

Acetosyringone2478-38-81-(4-Hydroxy-3,5-dimethoxyphenyl)ethanone4'-HYDROXY-3',5'-DIMETHOXYACETOPHENONEAcetosyringenin1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one866P45Y84SCHEBI:2404DTXSID2062454RefChem:552431DTXCID1037147219-610-5
名称をさらに表示
4'-ヒドロキシ-3',5'-ジメトキシアセトフェノン2,6-ジメトキシ-4-アセチルフェノール3',5'-ジメトキシ-4'-ヒドロキシアセトフェノン4-アセチル-2,6-ジメトキシフェノール1-(4-ヒドロキシ-3,5-ジメトキシフェニル)エタノン4-アセチルシリンゴール1-(3,5-ジメトキシ-4-ヒドロキシフェニル)エタノンシリンギルエタノンアセトシリンゴン3′,5′-ジメトキシ-4′-ヒドロキシアセトフェノン3′,5′‐ジメトキシ‐4′‐ヒドロキシアセトフェノンアセトシリンゴン (RG)3',5'-ジメトキシ-4'-ヒドロキシアセトフェノン, 97%4′-ヒドロキシ-3′,5′-ジメトキシアセトフェノン1-(4-ヒドロキシ-3,5-ジメトキシフェニル)エタン-1-オンSyringylethanone4-acetylsyringol5'SYRINGACETONE
3',5'-Dimethoxy-4'-hydroxyacetophenoneEthanone, 1-(4-hydroxy-3,5-dimethoxyphenyl)-Acetosyringon3,5-Dimethoxy-4-hydroxyacetophenoneMFCD00008748Acetophenone, 4'-hydroxy-3',5'-dimethoxy-4-hydroxy-3,5-dimethoxyacetophenone4-Hydroksy-3',5'-dwumetoksyacetofenon

データベース識別子

CAS
2478-38-8
PubChem CID
17198
DTXSID
DTXSID2062454
ChEMBL
CHEMBL224146
ChEBI
CHEBI:2404
UNII
866P45Y84S
EC Number
219-610-5
Nikkaji
J55.026D

物性

構造計算による物性

XLogP
0.2
極性表面積
55.8 Ų
水素結合供与体数
1
水素結合受容体数
4
回転可能結合数
3
重原子数
14

実験および物理化学的性質

Chemical ClassesBiological Agents -> Plant Oils and Extracts
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound
Physical DescriptionWhite to brown solid; [Sigma-Aldrich MSDS]
Collision Cross Section138.14 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点
124 · 124-127 °C(lit.)
沸点
293.08 °C · 293.08°C (rough estimate)
比重(密度)
1.2166 · 1.2166 (rough estimate)
屈折率
1.543 · 1.5430 (estimate)
貯蔵温度
Inert atmosphere,Room Temperature
溶解性
クロロホルム（微量）、メタノール（微量）

化学的性質

化学的特性beige to light brown crystalline powder

安全と法規制

GHS分類

GHS Classification · 4 件

Warning

H315 (100%): 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 49 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 · 2 件

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Ethanone, 1-(4-hydroxy-3,5-dimethoxyphenyl)-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySafe when used as a flavoring agent in food; [EFSA] A skin and strong eye irritant; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)

安全データ

F
10
wgk
2
rtecs
AM8440000
hs_code
29145090
risk_code
36/37/38
hazard_code
Xi

化学と産業

薬理情報

MeSH Pharmacological Classification · 2 件

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.

Drugs that are used to treat asthma.

用途と製造

UsesA flavoring agent that naturally occurs in pork and sherry; [EFSA]
応用分野 · 3 件

用途有機合成原料。

説明Acetosyringone is a phenol secreted by wounded plant tissues. It induces expression of virulence A genes and chemotaxis in A. tumefaciens strains that contain a tumor-inducing plasmid used to transfer genetic information to plant cells. Acetosyringone is widely used to increase efficacy of genetic transformation for the creation of genetically modified dicotyledonous and monocotyledonous plants.

使用A buffer also known as acetosyringone that is used in the synthesis of tetramethoxychalcone and its analogues as anticancer agents in vitro.

調製方法

製造方法Preparation by adding a solution of 4-hydroxy-3- iodo-5-methoxyacetophenone and cupric chloride in DMF to a solution of sodium methoxide in methanol and heating between 105° and 120° (86%).

上流・下流製品情報

サプライヤー50 社

杭州创引化工科技有限公司0571-87086220 13516718938 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

補足説明

定義ChEBI: A member of the class of acetophenones that is 1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5.

関連反応

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