| Identification | More | [Name]
3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID | [CAS]
1135-23-5 | [Synonyms]
3-(3-METHOXY-4-HYDROXYPHENYL)-PROPIONIC ACID
3-(4-HYDROXY-3-METHOXYPHENYL)PROPANOIC ACID
3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID
3-(4-HYDROXYMETHYL)PROPIONIC ACID
3-METHOXY-4-HYDROXYHYDROCINNAMIC ACID
4-HYDROXY-3-METHOXYHYDROCINNAMIC ACID
BETA-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID
HYDROFERULIC ACID
Benzenepropanoic acid, 4-hydroxy-3-methoxy-
3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC
HYDROFERULIC ACID(RG)
3-(4-HYDROXY-3-METHOXYPHENYL)PROPIONIC ACID 98%
3-Methoxy-4-hydroxybenzenepropanoic acid
3-Methoxy-4-hydroxybenzenepropionic acid
4-Hydroxy-3-methoxybenzenepropanoic acid | [EINECS(EC#)]
214-489-5 | [Molecular Formula]
C10H12O4 | [MDL Number]
MFCD00016558 | [Molecular Weight]
196.2 | [MOL File]
1135-23-5.mol |
| Chemical Properties | Back Directory | [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. | [form ]
powder to crystal | [pka]
4.73±0.10(Predicted) | [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 Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed.
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 .
S36:Wear suitable protective clothing . | [WGK Germany ]
2
| [HazardClass ]
IRRITANT | [HS Code ]
29189900 |
| Hazard Information | Back Directory | [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ChEBI: A monocarboxylic acid that is propanoic acid in which one of the hydrogens at position 3 has been replaced by a 4-hydroxy-3-methoxyphenyl group.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]
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 |
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