(E)-p-Methoxycinnamsure
(E)-3-(4-METHOXYPHENYL)ACRYLIC ACID · (E)-4-Methoxycinnamic acid · PMCA · AKOS B000181 · AKOS BB/0034 · AKOS BBS-00000769 · TIMTEC-BB SBB005717 · RARECHEM BK HC T257
Identifikatoren & physikalische Daten
| CAS No. | 830-09-1 |
|---|---|
| Summenformel | C10H10O3 |
| Durchschnittliche Molmasse | 178,18 g/mol |
| Monoisotopische Masse | 178,06299418 g/mol |
| SMILES | COc1ccc(/C=C/C(=O)O)cc1 |
| InChIKey | AFDXODALSZRGIH-QPJJXVBHSA-N |
| PubChem CID | 699414 |
| ChEMBL | CHEMBL95770 |
| ChEBI | CHEBI:48541 |
| EC No. | 212-594-0 |
| DTXSID | DTXSID1046059 |
| Lokaler Name | (E)-p-Methoxycinnamsure |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 46,5 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 190 |
| Stoffklassen | UV filter |
| SpringerMaterials Properties | Chemical diffusion |
| LogP (Verteilungskoeffizient) | 2.68 |
| Löslichkeit | 0.712 mg/mL at 25 °CSoluble in ethanol, ethyl acetate and other organic solvents. |
| Schmelzpunkt | 173 - 175 °C173.5 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 140.8 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)] |
| Siedepunkt | 342.6±17.0 °C(Predicted) |
| Dichte | 1.195±0.06 g/cm3(Predicted) |
| Lagerbedingungen | Keep in dark place,Sealed in dry,Room Temperature |
| pKa (Säurekonstante) | 4.60±0.10(Predicted) |
| Aggregatzustand | powder to crystal |
| Farbe | White to Almost white |
| BRN | 510468 |
| Kosmetik-Inhaltsstoffe Funktionen | UV FILTERLIGHT STABILIZER |
| InChI | InChI=1S/C10H10O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-7H,1H3,(H,11,12)/b7-4+ |
| InChIKey | AFDXODALSZRGIH-QPJJXVBHSA-N |
| SMILES | C(O)(=O)/C=C/C1=CC=C(OC)C=C1 |
| LogP (Verteilungskoeffizient) | 1.264 (est) |
| CAS Datenbank | 943-89-5(CAS DataBase Reference) |
| NIST chemische Informationen | 2-Propenoic acid, 3-(4-methoxyphenyl)-, (e)-(943-89-5) |
| EPA chemische Informationen | 2-Propenoic acid, 3-(4-methoxyphenyl)-, (2E)- (943-89-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (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 54 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: 2-Propenoic acid, 3-(4-methoxyphenyl)-Chemical: 2-Propenoic acid, 3-(4-methoxyphenyl)-, (E)-Status: Active Update: 26-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/223312-Propenoic acid, 3-(4-methoxyphenyl)-, (2E)-: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 2918.29.7500 |
| RTECS-Nr. | UD3391300 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-37/39 |
| Gefahrenklasse | IRRITANT |
| Lagerklasse | 13 - Non Combustible Solids |
Anwendungen & Verwendung
Verwenden
Esters derived from trans-4-methoxycinnamic acid are effective absorbers of UV radiation. The starting material was trans-4-methoxycinnamic acid and 3,5dimethoxybenzoic acid methyl ester in isolated avenanthramide alkaloids synthsis. trans-4-Methoxycinnamic acid was converted into its acid chloride (yield 98%) with thionyl chloride. Employed in organic synthesis of pharmaceutical intermediates, synthetic anti-adrenergic drugs esmolol, cosmetics ultraviolet absorption.
Herstellung & Synthese
synthetische
4-methoxycinnamic acid synthesis : In a 25-mL, roundbottomed flask, 4-methoxybenzaldehyde (0.804 mL, 6.61 mmol) (3), malonic acid (1.75 g, 16.8 mmol), and β-alanine (0.10 g, 1.12 mmol) were dissolved in pyridine (3.0 mL, 37.1 mmol) and heated under reflux for 90 minutes. After cooling to room temperature, the reaction mixture was placed in an ice bath and 8.0 mL of concentrated HCl was slowly added. The resulting white precipitate was collected by vacuum filtration, washed with cold water (2 x 10mL) and dried thoroughly. The product was recrystallized from absolute ethanol (~20 mL).Synthesis of 4-methoxycinnamic acid