4-METHOXYCINNAMIC ACID
- CAS NO.:943-89-5
- Empirical Formula: C10H10O3
- Molecular Weight: 178.18
- MDL number: MFCD00004398
- EINECS: 213-405-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-29 17:54:30
What is 4-METHOXYCINNAMIC ACID?
The Uses of 4-METHOXYCINNAMIC ACID
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.
Preparation
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
Definition
ChEBI: 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.
Purification Methods
Crystallise the acid from MeOH to constant melting point and UV spectrum. [Beilstein 10 IV 1005.]
Properties of 4-METHOXYCINNAMIC ACID
Melting point: | 173.5 °C(lit.) |
Boiling point: | 342.6±17.0 °C(Predicted) |
Density | 1.195±0.06 g/cm3(Predicted) |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
solubility | Soluble in ethanol, ethyl acetate and other organic solvents. |
pka | 4.60±0.10(Predicted) |
form | powder to crystal |
color | White to Almost white |
BRN | 510468 |
CAS DataBase Reference | 943-89-5(CAS DataBase Reference) |
NIST Chemistry Reference | 2-Propenoic acid, 3-(4-methoxyphenyl)-, (e)-(943-89-5) |
EPA Substance Registry System | 2-Propenoic acid, 3-(4-methoxyphenyl)-, (2E)- (943-89-5) |
Safety information for 4-METHOXYCINNAMIC ACID
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P304+P340:IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up. |
Computed Descriptors for 4-METHOXYCINNAMIC ACID
InChIKey | AFDXODALSZRGIH-QPJJXVBHSA-N |
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