| Identification | Back Directory | [Name]
Ethyl 4-methoxycinnamate | [CAS]
24393-56-4 | [Synonyms]
EPMC
RARECHEM AL BI 0241
Ethyl 4-Methoxyciamate
Ethyl 4-methoxycinmate
ETHYL 4-METHOXYCINNAMATE
ETHYL P-METHOXYCINNAMATE
ParaMethoxyethylcinnaMate
P-methoxyl ethyl cinnamate
Ethyl4-Methoxycinnamate>
Ethyl para-methoxycinnamate
(E)-Ethyl p-methoxycinnamate
ethyl (E)-4-methoxycinnamate
Methoxycinnamicacidethylester
Ethyl trans-4-methoxycinnamate
Ethyl trans-p-methoxycinnamate
ETHYL 3-(4-METHOXYPHENYL)ACRYLATE
4-METHOXYCINNAMIC ACID ETHYL ESTER
Ethyl 4-methoxycinnamate USP/EP/BP
(E)-Ethyl 3-(4-Methoxyphenyl)acrylate
4-METHOXYCINNAMIC ACID ETHYL ESTER 98+%
trans-4-Methoxycinnamic acid ethyl ester
trans-p-Methoxycinnamic acid ethyl ester
Ethyl (E)-3-(4-methoxyphenyl)-2-propenoate
3-(4-METHOXYPHENYL)ACRYLIC ACID ETHYL ESTER
(E)-3-(4-Methoxyphenyl)-2-propenoic acid ethyl ester
2-Propenoic acid, 3-(4-methoxyphenyl)-, ethyl ester, (2E)-
1-(tert-butoxycarbonyl)-4-(4-Methoxyphenyl)pyrrolidine-3-carboxylic acid
4-Methoxycinnamic Acid Ethyl Ester
Ethyl 3-(4-Methoxyphenyl)acrylate
3-(4-Methoxyphenyl)acrylic Acid Ethyl Ester
Ferulic acid,ethyl ester,4-Methoxycinnamic Acid Ethyl Ester,Ethyl trans-4-methoxycinnamate,ethyl p-methoxycinnamate,3-(4-Methoxyphenyl)acrylic Acid | [EINECS(EC#)]
202-494-5 | [Molecular Formula]
C12H14O3 | [MDL Number]
MFCD00026906 | [MOL File]
24393-56-4.mol | [Molecular Weight]
206.24 |
| Chemical Properties | Back Directory | [Melting point ]
49°C | [Boiling point ]
187 °C / 15mmHg | [density ]
1.080±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
neat | [color ]
Off-White | [Water Solubility ]
insoluble in water | [BRN ]
2210033 | [LogP]
2.650 (est) | [NIST Chemistry Reference]
Ethyl p-methoxycinnamate(24393-56-4) |
| Hazard Information | Back Directory | [Chemical Properties]
White crystalline | [Uses]
Ethyl 4-methoxycinnamate is an derivative of 4-methoxycinnamic acid, an antihyperglycemic/hypoglycemic agent that works by stimulating insulin secretion from pancreas and could be developed into a new potential for therapeutic agent used in type 2 diabetic patients. | [Preparation]
Ethyl 4-methoxycinnamate synthesis: 4-Methoxycinnamic Acid (0.60 g, 3.36 mmol) was dissolved in 10 mL of dry N,N-dimethylformamide (DMF) in a 25-mL, roundbottomed flask. Cesium carbonate (1.65 g, 5.06 mmol) was added followed by iodoethane (1.0 mL, 12.5 mmol). The flask was capped (rubber septum) and the heterogeneous mixture stirred vigorously at 50 °C for one hour. After this time, HCl (1.0 M, 4.0 mL) was added to quench the reaction. The liquid was decanted from any remaining solid and extracted with 3 : 1 hexanes/ethyl acetate (2 x 10 mL). The organic layer was washed with brine (20 mL), dried with MgSO4, filtered, and solvent removed. The remaining oil solidified on standing to form colorless prisms.
Synthesis of ethyl 4-methoxycinnamate | [General Description]
Ethyl p-methoxycinnamate (EPMC) is a natural product found in K. galanga and C. zedoaria extracts with anti-inflammatory, antiangiogenic, antifungal, larvicidal, and analgesic activities. It inhibits COX-1 and COX-2 in vitro (IC50s = 1.12 and 0.83 μM, respectively) and reduces IL-1 and TNF-α production in vivo. EPMC inhibits granuloma tissue formation and acts as an analgesic, delaying tail flick time, in a dose-dependent manner in rats. It inhibits blood vessel growth in rat aortic explants (IC50 = 91.9 μg/ml). EPMC (<10 μg/ml) also reduces growth of T. rubrum, A. niger, S. cerevisiae, and E. floccosum and is larvicidal (LC50 = 53.64 ppm) against Ae. aegypti. |
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