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393533

Sigma-Aldrich

3-(2-Hydroxyphenyl)propionic acid

99%

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About This Item

Fórmula lineal:
HOC6H4CH2CH2CO2H
Número de CAS:
495-78-3
Peso molecular:
166.17
MDL number:
MFCD00014026
UNSPSC Code:
12352100
PubChem Substance ID:
24864523
NACRES:
NA.22

assay

99%

mp

86-89 °C (lit.)

SMILES string

OC(=O)CCc1ccccc1O

InChI

1S/C9H10O3/c10-8-4-2-1-3-7(8)5-6-9(11)12/h1-4,10H,5-6H2,(H,11,12)

InChI key

CJBDUOMQLFKVQC-UHFFFAOYSA-N

General description

3-(2-Hydroxyphenyl) propionic acid is a phenyl propionic acid derivative. It was found to be one of the constituents of Justicia pectoralis Jacq. extract which was analyzed by gas chromatography/mass spectrometry (GC/MS). The antiulcerogenic effect of 3-(2-hydroxyphenyl) propionic acid in the prevention of serotonin-induced ulcerogenesis has been studied in rats. It has been reported to be one of the major microbial metabolite of both (+)-catechin and (-)-epicatechin by human faecal microbiota. Crystal structure study reveals that 3-(2-hydroxyphenyl)propionic acid crystals are monoclinic with space group P21/c.

Application

3-(2-Hydroxyphenyl)propionic acid is suitable as a growth substrate for various strains of E. coli and as a standard in the study of microbial metabolism of catechin stereoisomers.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Microbial metabolism of catechin stereoisomers by human faecal microbiota: comparison of targeted analysis and a non-targeted metabolomics method.
Aura AM, et al.
Phytochemistry Letters, 1(1), 18-22 (2008)
Structure of 3-(2-hydroxyphenyl) propionic acid.
Begum NS, et al.
Acta Crystallographica Section C, Crystal Structure Communications, 48(6), 1076-1078 (1992)
R Burlingame et al.
Journal of bacteriology, 155(1), 113-121 (1983-07-01)
A number of laboratory strains and clinical isolates of Escherichia coli utilized several aromatic acids as sole sources of carbon for growth. E. coli K-12 used separate reactions to convert 3-phenylpropionic and 3-(3-hydroxyphenyl)propionic acids into 3-(2,3-dihydroxyphenyl)propionic acid which, after meta-fission
S Tanaka et al.
Planta medica, 55(3), 245-248 (1989-06-01)
Two active compounds that prevent serotonin-induced ulcerogenesis in rats were isolated from Chinese cinnamon (the stem bark of Cinnamomum cassia) and identified as 3-(2-hydroxyphenyl)-propanoic acid and its O-glucoside. The former compound, administered orally or parenterally to rats at a remarkably
J X de Vries et al.
Biomedical & environmental mass spectrometry, 15(8), 413-417 (1988-04-15)
The analysis of extracts from the South American plant Justicia pectoralis Jacq. permitted the identification, among other compounds, of coumarin, dihydrocoumarin, umbelliferone and 3-(2-hydroxyphenyl)propionic acid by gas chromatography/mass spectrometry (GC/MS); the acids and phenolic compounds were derivatized with diazomethane. GC/MS

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