基本情報
- CAS
552-41-0- 標準SMILES
COc1ccc(C(C)=O)c(O)c1- InChIKey
UILPJVPSNHJFIK-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
Paeonol is a member of phenols and a member of methoxybenzenes. It has a role as a metabolite.
名称と識別子
- 優先名称
- Paeonol
- IUPAC
- 1-(2-hydroxy-4-methoxyphenyl)ethanone
- 現地名
- 2'-ヒドロキシ-4'-メトキシアセトフェノン
- 英語名
- Paeonol
- 分子式
- C9H10O3
- 分子量
- 166.17
名称と別名
名称をさらに表示
データベース識別子
- CAS
552-41-0- PubChem CID
- 11092
- DTXSID
DTXSID1022059- ChEMBL
CHEMBL1079227- ChEBI
CHEBI:69581- UNII
- 3R834EPI82
- EC Number
- 209-012-2
- Nikkaji
- J4.483K
物性
構造計算による物性
- XLogP
- 2
- 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
Collision Cross Section
123.8 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
124.9 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 48 · 48-50 °C(lit.)
- 沸点
- 154 °C · 154 °C / 20mmHg
- 比重(密度)
- 1.3102 · 1.3102
- 屈折率
- 1.5452 · 1.5452 (estimate)
- 闪点
- 230 °F · >230 °F
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- アセトニトリル(微量)、クロロホルム(微量)、メタノール(微量)
- 外見
- 結晶性粉末
- 酸解離定数(Pka)
- 9.79 · 9.79±0.10(Predicted)
- 色
- 白からベージュ
- 臭い (Odor)
- Warm-aromatic odor
- においのタイプ
- pungent
- BRN
- 1282794 · 1282794
- 化粧品成分の機能
- スキンコンディショニング抗酸化物質
- InChI
- InChI=1S/C9H10O3/c1-6(10)8-4-3-7(12-2)5-9(8)11/h3-5,11H,1-2H3
- InChIKey
- UILPJVPSNHJFIK-UHFFFAOYSA-N
- SMILES
- C(=O)(C1=CC=C(OC)C=C1O)C
- LogP
- 1.98 · 1.980
- CAS データベース
- 552 · 552-41-0(CAS DataBase Reference)
- NISTの化学物質情報
- 1 · Ethanone, 1-(2-hydroxy-4-methoxyphenyl)-(552-41-0)
化学的性質
化学的特性white to beige crystalline powder
安全と法規制
GHS分類
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 52 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Hazards Summary
Causes altered sleep time in intraperitoneal and intravenous lethal-dose studies of mice; Causes analgesia and effects on inflammation in acute intraperitoneal studies of rats; [RTECS] A skin and strong eye irritant; Prolonged or repeated exposure may cause eye injury; Toxic by ingestion; [Sigma-Aldrich MSDS] See Acetophenone and Anisole.
安全データ
- wgk
- 3
- rtecs
- RT1215000
- 毒性
- LD50 orl-mus: 3430 mg/kg YKKZAJ 89,1205,69
- hs_code
- 29145090
- risk_code
- 20/21/22-36/37/38
- 化審法
- (3)-1252
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-28-36/37/39-45
- Hazard Classifications
- Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye 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
応用分野
説明Paeonol is the main active ingredient of the cortex of thePaeonol raw materials with high purity can be derived from plant extracts by chemical synthesis. The commonly used extraction methods of paeonol include boiling method, alcohol extraction, steam distillation, and CO2 supercritical fluid extraction . But due to the limitation of plant resources and the lower content of paeonol in the natural plants, there are many separation and purification difficulties existed in the extraction methods. The chemical synthesis process is relatively easy, and the final product usually can be obtained through two- to three-step reaction and separation process . Ranunculaceae plants including Paeonia suffruticosa Andr. (Moutan cortex, Mudanpi) and Rhododendron plant Cynanchum paniculatum (Bge.) Kitag. (Cynanchi paniculati radix et rhizome, Xuchangqing). Moutan cortex and Xuchangqing are commonly used as traditional Chinese medicine. Moutan cortex has the effects on clearing heat, cooling blood, activating blood, resolving stasis, and retreating heat; Xuchangqing also has many effects, such as dispelling wind, relieving pain and itching, and so on.
来歴As the main active ingredient of Moutan cortex and Xuchangqing, paeonol has been used in clinical practice since ancient times. Paeonol was first isolated from Moutan cortex by Japanese scholar Changjing Changyi in 1884 . This clinical observation was proceeded at more than 10 medical units in Shanghai and other places and lasted more than 1 year since 1971. Paeonol injection was the earliest recorded in the Chinese pharmacopoeia 1977 edition; it is the main formulation until now. But because of the poor water solubility of paeonol, it is necessary to improve its solubility to be used as injection. Ten times amount of Tween compared to paeonol was used in the injection to increase the dissolution. In the 1970s, paeonol was made into oil solution for intramuscular injection. But these are with security risks and the use of inconvenience and other shortcomings. Pharmacist obtained paeonol sodium sulfonate by sulfonated paeonol, so the problem of water solubility had been resolved, and the injection of paeonol sodium sulfonate also came into being . In 2003, the quality standard of paeonol sodium sulfonate was also promoted from the local standard to the national standard. The dosage form of paeonol for skin is mainly ointment.
使用Paeonol acting as a β-Secretase inhibitor an anti-apoptotic agent is used in the treatment of memory loss after ischemic stroke. Anti-inflammatory and analgesic.
一般的な説明This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
調製方法
製造方法Preparation by reaction of methyl iodide, or dimethyl sulfate on resacetophenone in sodium hydroxide or potassium hydroxide solution (quantitative yield) (70–75%).
上流・下流製品情報
下流製品
サプライヤー100 社
補足説明
定義ChEBI: A natural product found in Paeonia rockii subspecies rockii.
関連反応
化合物ノート
読み込み中…