| Identification | More | [Name]
Ethyl 4'-hydroxy-3'-methoxycinnamate | [CAS]
4046-02-0 | [Synonyms]
4-HYDROXY-3-METHOXYCINNAMIC ACID ETHYL ESTER
BUTTPARK 121\04-55
Ethyl 3-(4-hydroxy-3-methoxyphenyl)acrylate
ETHYL 4-AMINOCINNAMATE
ETHYL 4-HYDROXY-3-METHOXYCINNAMATE
ETHYL FERULATE
ETHYL TRANS-3-(4'-HYDROXY-3'-METHOXYPHENYL)ACRYLATE
FERULIC ACID ETHYL ESTER
RARECHEM AL BI 0735
Ethyl ferulate~Ferulic acid ethyl ester~4-Hydroxy-3-methoxycinnamic acid ethyl ester
(E)-3-(4-HYDROXY-3-METHOXY-PHENYL)-ACRYLIC ACID ETHYL ESTER
Ferulic acid ethyl eser
ETHYL 4-HYDROXY-3-METHOXYCINNAMATE (FERULIC ACID ETHYL ESTER)
3-(3-Methoxy-4-hydroxyphenyl)propenoic acid ethyl ester
3-(4-Hydroxy-3-methoxyphenyl)propenoic acid ethyl ester | [EINECS(EC#)]
223-745-5 | [Molecular Formula]
C12H14O4 | [MDL Number]
MFCD00009190 | [Molecular Weight]
222.24 | [MOL File]
4046-02-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
63-65 °C(lit.)
| [Boiling point ]
164-166 °C0.5 mm Hg(lit.)
| [density ]
1.0643 (rough estimate) | [refractive index ]
1.4560 (estimate) | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
8.88±0.18(Predicted) | [color ]
White to Off-White | [Sensitive ]
Light Sensitive | [BRN ]
2696807 | [Stability:]
Hygroscopic, Light Sensitive | [InChIKey]
ATJVZXXHKSYELS-FNORWQNLSA-N | [LogP]
1.940 (est) | [CAS DataBase Reference]
4046-02-0(CAS DataBase Reference) | [NIST Chemistry Reference]
ethyl ferulate(4046-02-0) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
29189900 |
| Hazard Information | Back Directory | [Description]
Ferulic acid is a hydroxycinnamic acid that is abundant in plants and originally derived from giant fennel (F. communis). This naturally-occurring phenolic has antioxidant activities that provide protection against inflammation and cancer.1,2,3,4 Ferulic acid ethyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes.5 Ferulic acid ethyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC50 = 66.7 μM for ferulic acid ethyl ester vs. 44.6 μM for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging).6 However, ferulic acid ethyl ester increases the expression of heme oxygenase-1, Hsp70, and Hsp72, providing neuroprotection against amyloid β-peptide.7,8 Moreover, ferulic acid ethyl ester (25 μM) completely prevents cytotoxicity induced by ultraviolet B irradiation of normal human epidermal melanocytes, again associated with an induced expression of heme oxygenase-1 and Hsp70.9 | [Uses]
Ferulic acid ethyl ester is an ethyl ester derivative of Ferulic acid (F308900), which is used as an antioxidant and food preservative. | [Synthesis]
To an ice-chilled suspension of trans-ferulic acid (1.942 g, 10 mmol, 1 eq) in absolute ethanol (20 mL) was added thionyl chloride (0.87 mL, 12 mmol, 1.2 eq). The resulting mixture was refluxed with stirring for 20 h. The solution was concentrated in vacuo, dissolved in ethyl acetate (30 mL) and washed with a 1 M HCI solution (15 mL), saturated NaHCOs solution (15 mL) and brine (15 mL). The organic layer was dried over anhydrous NajSC and concentrated in vacuo to afford Ethyl 4-hydroxy-3-methoxycinnamate as an orange oil (2.185 g, yield: 98%).
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