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3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID

Product Name3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID
CAS1135-23-5
MFC10H12O4
MW196.2
EINECS214-489-5
MOL File1135-23-5.mol

Chemical Properties

Melting point	87-93 °C
Boiling point	120-130 °C(Press: 0.5 Torr)
Density	1.259±0.06 g/cm3(Predicted)
storage temp.	Storage temp. 2-8°C
solubility	Soluble in dimethyl sulfoxide and methanol.
pka	4.73±0.10(Predicted)
form	powder to crystal
color	White to Light yellow
BRN	2110370
InChI	InChI=1S/C10H12O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2,4,6,11H,3,5H2,1H3,(H,12,13)
InChIKey	BOLQJTPHPSDZHR-UHFFFAOYSA-N
SMILES	C1(CCC(O)=O)=CC=C(O)C(OC)=C1
LogP	0.810 (est)
CAS DataBase Reference	1135-23-5(CAS DataBase Reference)

Safety Information

Hazard Codes	Xn
Risk Statements	22-36/37/38
Safety Statements	26-36
WGK Germany	2
HazardClass	IRRITANT
HS Code	29189900
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Oral Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Uses

3-(4-Hydroxy-3-methoxyphenyl)propionic acid (hydroferulic acid) was used to inhibit prostaglandin E(2) production.

Uses

A caffeine metabolite which showed high antioxidant activity. It is a very sensitive biomarker for the consumption of relatively small amount of coffee.

Definition

ChEBI: A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group.

Synthesis

1135-24-6

3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID

1135-23-5

The general procedure for the synthesis of isopropyl phosphate (mono- and di-ester mixtures) from 3-methoxy-4-hydroxyphenylacrylic acid was as follows: to a stirred suspension of ferulic acid (25 g, 128.74 mmol) in methanol (200 ml) was added Pd/C catalyst (3.75 g). The reaction mixture was subjected to hydrogenation under hydrogen pressure of 1.2 MPa for 4 h at 50°C. Upon completion of the reaction, the mixture was cooled to room temperature, the catalyst was removed by filtration, and a white solid product (25 g, 99% yield) was obtained by concentration under reduced pressure. The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3) and ESI-MS: 1H NMR δ 6.76 (d, J = 7.8 Hz, 1H), 6.62 (m, 2H), 3.79 (s, 3H), 2.81 (t, J = 7.7 Hz, 2H), 2.58 (t, J = 7.7 Hz, 2H); ESI-MS m /z: 195.1 [M-H]

in vivo

Assessing the influence of an 11 weeks intervention with a resistant starch-enriched whole grain diet (HI-RS-WG, 25% RS) compared to a WG control diet (LOW-RS-WG, 6.9% RS) on serum profile of polyphenols (PPs) in 20 Zucker Diabetic Fatty rats. Five PPs were identified and quantified in serum samples of rats belonging to both intervention groups. HI-RS-WG rats had 2.6 folds higher serum concentrations of total PPs than LOW-RS-WG rats. An explorative data reduction approach, based on the Principal Component Analysis identified two principal components related to the gut microbiota fermentation and food intake, respectively. Results showed that the abundance of hippuric acid and Dihydroferulic acid in HI-RS-WG rats was explained by the stronger gut microbiota fermentation in those rats than in LOW-RS-WG rats^[4].

References

[1] Advanced Synthesis and Catalysis, 2013, vol. 355, # 1, p. 81 - 86
[2] Tetrahedron Letters, 2010, vol. 51, # 44, p. 5753 - 5756
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 13, p. 4462 - 4466
[4] European Journal of Medicinal Chemistry, 2014, vol. 87, p. 429 - 439
[5] Journal of the American Chemical Society, 2017, vol. 139, # 10, p. 3767 - 3773

3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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