Methyl 3-(4-hydroxyphenyl)propionate Chemical Properties

Melting point:

39-41 °C (lit.)

Boiling point:

108 °C/11 mmHg (lit.)

Density 

1.1272 (rough estimate)

refractive index 

1.5160 (estimate)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in chloroform and methanol.

form 

Powder

pka

9.89±0.15(Predicted)

color 

White transparent

CAS DataBase Reference

5597-50-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzenepropanoic acid, 4-hydroxy-, methyl ester(5597-50-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

29181990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Methyl 3-(4-hydroxyphenyl)propionate Usage And Synthesis

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

Methyl 3-(4-hydroxyphenyl)propionate(5597-50-2)Related Product Information

• Methylparaben
• Calcium Propionate
• 4-Hydroxyphenylacetic acid
• 4'-Hydroxypropiophenone
• 4-Hydroxybenzoic acid
• 4'-Hydroxyacetophenone
• 4-Methoxyphenol
• Butylparaben
• Bensulfuron methyl
• METHYL 2-AMINO-2-(4-HYDROXYPHENYL)ACETATE
• 4-Hydroxybenzaldehyde
• 4-Hydroxy-D-(-)-2-phenylglycine
• 4-Hydroxybenzyl alcohol
• CHLOROPHOSPHONAZO III
• Kresoxim-methyl
• Methyl acrylate
• Thiophanate-methyl
• 2-(4-HYDROXYPHENYL)PROPIONIC ACID