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| | Ethyl 4-hydroxy-3-methoxycinnamate Basic information |
| | Ethyl 4-hydroxy-3-methoxycinnamate Chemical Properties |
| 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 | | Cosmetics Ingredients Functions | ANTIOXIDANT | | InChI | 1S/C12H14O4/c1-3-16-12(14)7-5-9-4-6-10(13)11(8-9)15-2/h4-8,13H,3H2,1-2H3/b7-5+ | | InChIKey | ATJVZXXHKSYELS-FNORWQNLSA-N | | SMILES | CCOC(=O)\C=C\c1ccc(O)c(OC)c1 | | LogP | 1.940 (est) | | CAS DataBase Reference | 4046-02-0(CAS DataBase Reference) | | NIST Chemistry Reference | ethyl ferulate(4046-02-0) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39-36 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 29189900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | Ethyl 4-hydroxy-3-methoxycinnamate Usage And Synthesis |
| 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. Ferulic acid ethyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. 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). However, ferulic acid ethyl ester increases the expression of heme oxygenase-1, Hsp70, and Hsp72, providing neuroprotection against amyloid β-peptide. 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. | | Chemical Properties | White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from the rhizome of Ligusticum chuanxiong Hort. | | 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%).
| | References | [1] Organic and Biomolecular Chemistry, 2010, vol. 8, # 22, p. 5199 - 5211
[2] Tetrahedron Letters, 2014, vol. 55, # 32, p. 4427 - 4429
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 23, p. 7732 - 7752
[4] Patent: US2008/153878, 2008, A1. Location in patent: Page/Page column 17; 24
[5] Molecules, 2011, vol. 16, # 5, p. 3580 - 3596 |
| | Ethyl 4-hydroxy-3-methoxycinnamate Preparation Products And Raw materials |
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