Grundinformationen
- CAS
830-09-1- Standard-SMILES
COc1ccc(/C=C/C(=O)O)cc1- InChIKey
AFDXODALSZRGIH-QPJJXVBHSA-N- Summenformel
- C10H10O3
- Durchschnittliche Molmasse
- 178,18 g/mol
- Monoisotopische Masse
- 178,06299418
Überblick
4-methoxycinnamic acid is a methoxycinnamic acid having a single methoxy substituent at the 4-position on the phenyl ring. It is functionally related to a cinnamic acid.
Namen und Bezeichner
- Bevorzugter Name
- 4-Methoxycinnamic Acid
- IUPAC
- (E)-3-(4-methoxyphenyl)prop-2-enoic acid
- Lokaler Name
- (E)-p-Methoxycinnamsure
- Englischer Name
- trans-O-Methyl-p-coumaric acid
- Summenformel
- C10H10O3
- Molmasse
- 178.18
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
830-09-1、943-89-5- PubChem CID
- 699414
- DTXSID
DTXSID1046059- ChEMBL
CHEMBL95770- ChEBI
CHEBI:48541- UNII
- 6G4ML8401A
- EC Number
- 212-594-0、213-405-4
- Nikkaji
- J47.704D、J60.989G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1,8
- Polarare Oberfläche (TPSA)
- 46,5 Ų
- H-Brücken-Donoren
- 1
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 3
- Schwere Atome
- 13
- Formalladung
- 0
- Komplexität
- 190
Experimentelle und physikochemische Eigenschaften
LogP
2.68
2.68
Physikochemische Eigenschaften
- Schmelzpunkt
- 173.5 °C · 173.5 °C(lit.)
- Siedepunkt
- 342.6 · 342.6±17.0 °C(Predicted)
- Dichte
- 1.195 · 1.195±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- Soluble in ethanol, ethyl acetate and other organic solvents.
- pka
- 4.6 · 4.60±0.10(Predicted)
- Aggregatzustand
- powder to crystal
- Farbe
- White to Almost white
- BRN
- 510468 · 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
- 1.264 · 1.264 (est)
- CAS Datenbank
- 943 · 943-89-5(CAS DataBase Reference)
- NIST chemische Informationen
- 2 · 2-Propenoic acid, 3-(4-methoxyphenyl)-, (e)-(943-89-5)
- EPA chemische Informationen
- 2 · 2-Propenoic acid, 3-(4-methoxyphenyl)-, (2E)- (943-89-5)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
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 54 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
Gefahrenhinweise
Regulatory Information
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/22331
2-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%)
Skin Irrit. 2 (100%)
Sicherheitsdaten
- F
- 8
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 2918.29.7500
- RTECS-Nr.
- UD3391300
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-37/39
- hazard_class
- IRRITANT
- Speicherklasse
- 13 - Non Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Verwendung und Herstellung
General Manufacturing Information
2-Propenoic acid, 3-(4-methoxyphenyl)-: ACTIVE
2-Propenoic acid, 3-(4-methoxyphenyl)-, (2E)-: INACTIVE
Anwendungen
VerwendenEsters 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.
Darstellung
synthetische4-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
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