Chemical Properties
white transparent low melting mass
Uses
Methyl 3-(4-hydroxyphenyl)propionate may be used in the enzymatic coupling of saccharides to protein.
Definition
ChEBI: Methyl 3-(4-hydroxyphenyl)propionate is a methyl ester resulting from the formal condensation of the carboxy group of phloretic acid with methanol. It is a nitrification inhibitor and a plant growth regulator. It has a role as a nitrification inhibitor and a plant growth regulator. It is a member of phenols and a methyl ester. It is functionally related to a phloretic acid.
General Description
Methyl 3-(4-hydroxyphenyl)propionate is reported to be responsible for biological nitrification inhibition in sorghum (
Sorghum bicolor).
Synthesis
General procedure for the synthesis of methyl 4-hydroxyphenylpropionate from methyl 4-hydroxycinnamate: Pd/C (0.1 g) was added to a solution of methyl (E)-3-(4-hydroxyphenyl)acrylate (1.0 g, 5.6 mmol) in ethanol (20 mL). The reaction mixture was stirred vigorously at room temperature under hydrogen atmosphere (1 bar) for 21 hours. Upon completion of the reaction, the suspension was filtered through a diatomaceous earth pad and evaporated to dryness under vacuum to afford the oily product methyl 3-(4-hydroxyphenyl)propionate (1.0 g, 5.6 mmol, 99% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.07 (ddd, J=8.8,2.8,2.0 Hz, 2H), 6.76 (ddd, J=8.8,2.8,2.0 Hz, 2H), 4.72 (br s, 1H), 3.67 (s, 3H), 2.88 (t, J=7.8 Hz, 2H). 2.60 (t, J=7.8Hz, 2H).
References
[1] Journal of Natural Products, 1999, vol. 62, # 1, p. 102 - 106
[2] Patent: EP2745876, 2014, A1. Location in patent: Page/Page column
[3] Patent: US2015/344408, 2015, A1. Location in patent: Paragraph 0413-0415
[4] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 26, p. 10635 - 10640
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 30, p. 7785 - 7788
