2'-Hydroxy-4'-methoxyacetophenon
1-(2-HYDROXY-4-METHOXYPHENYL)ETHAN-1-ONE · Ethanone, 1-(2-hydroxy-4-methoxyphenyl)- · PEONOL · 1-(2-HYDROXY-4-METHOXYPHENYL)ETHANONE · Paeonal · Paeonol std. · 2-Hydroxy-4-methoxy · Paeonol (white powder)
Identifikatoren & physikalische Daten
| CAS No. | 552-41-0 |
|---|---|
| Summenformel | C9H10O3 |
| Durchschnittliche Molmasse | 166,17 g/mol |
| Monoisotopische Masse | 166,06299418 g/mol |
| SMILES | COc1ccc(C(C)=O)c(O)c1 |
| InChIKey | UILPJVPSNHJFIK-UHFFFAOYSA-N |
| PubChem CID | 11092 |
| ChEMBL | CHEMBL1079227 |
| ChEBI | CHEBI:69581 |
| EC No. | 209-012-2 |
| DTXSID | DTXSID1022059 |
| Lokaler Name | 2'-Hydroxy-4'-methoxyacetophenon |
Chemische & physikalische Eigenschaften
| XLogP | 2 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 12 |
| Formalladung | 0 |
| Komplexität | 167 |
| Stoffklassen | Other Classes -> Aromatic Ketones |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | 1.98 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Dampfdruck | 0.000683 [mmHg] |
| Physical Description | Off-white crystalline solid[Sigma-Aldrich MSDS] |
| Collision Cross Section | 123.8 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]124.9 Ų [M+H]+ [CCS Type: TW |
| Schmelzpunkt | 48-50 °C(lit.) |
| Siedepunkt | 154 °C / 20mmHg |
| Dichte | 1.3102 |
| Brechungsindex | 1.5452 (estimate) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly) |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | 9.79±0.10(Predicted) |
| Farbe | White to beige |
| Geruch | Warm-aromatic odor |
| Geruchsart | pungent |
| BRN | 1282794 |
| Kosmetik-Inhaltsstoffe Funktionen | SKIN CONDITIONINGANTIOXIDANT |
| 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 (Verteilungskoeffizient) | 1.980 |
| CAS Datenbank | 552-41-0(CAS DataBase Reference) |
| NIST chemische Informationen | Ethanone, 1-(2-hydroxy-4-methoxyphenyl)-(552-41-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (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. |
|---|---|
| Gefahrenübersicht | Causes altered sleep time in intraperitoneal and intravenous lethal-dose studies of miceCauses analgesia and effects on inflammation in acute intraperitoneal studies of rats[RTECS] A skin and strong eye irritantProlonged or repeated exposure may cause eye injuryToxic by ingestion[Sigma-Aldrich MSDS] See Acetophenone and Anisole. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29145090 |
| RTECS-Nr. | RT1215000 |
| R-Sätze (R) | 20/21/22-36/37/38 |
| Toxizität | LD50 orl-mus: 3430 mg/kg YKKZAJ 89,1205,69 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-28-36/37/39-45 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
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.
History
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.
Verwenden
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.
Herstellung & Synthese
synthetische
Preparation by reaction of methyl iodide, or dimethyl sulfate on resacetophenone in sodium hydroxide or potassium hydroxide solution (quantitative yield) (70–75%).