2-(3-hydroxy-4-methoxyphenyl)acetic acid

• ChemBase ID: 6713
• Molecular Formular: C9H10O4
• Molecular Mass: 182.1733
• Monoisotopic Mass: 182.0579088
• SMILES: c1c(c(cc(c1)CC(=O)O)O)OC
• Canonical SMILES: COc1ccc(cc1O)CC(=O)O
• InChI: InChI=1S/C9H10O4/c1-13-8-3-2-6(4-7(8)10)5-9(11)12/h2-4,10H,5H2,1H3,(H,11,12)
• InChIKey: BWXLCOBSWMQCGP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3-hydroxy-4-methoxyphenyl)acetic acid
• IUPAC Traditional name: isohomovanillic acid
• Synonyms: 3-Hydroxy-4-methoxyphenylacetic acid; 3-Hydroxy-4-methoxyphenylacetic acid; 3-Hydroxy-4-methoxybenzeneacetic Acid; 4-Methoxy-3-hydroxyphenylacetic Acid; Homoisovanillic Acid; Isohomovanillic Acid; 3-羟基-4-甲氧基苯乙酸

Database IDs

• CAS Number: 1131-94-8
• MDL Number: MFCD00016829
• PubChem SID: 160970020
• PubChem CID: 160562

CALCULATED PROPERTIES

• Acid pKa: 3.744853
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.6057299
• LogD (pH = 7.4): -2.1384158
• Log P: 1.1497575
• Molar Refractivity: 45.8097 cm^3
• Polarizability: 17.699709 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 127-132 °C; 128-130°C

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C9H10O4

DETAILS

Sigma Aldrich - 716391

Packaging
1 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 716391.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - H946410

3-Hydroxy-4-methoxyphenylacetic acid is a 4-O-methylated metabolite of catechol amines in man. 3-Hydroxy-4-methoxyphenylacetic acid is also a metabolite of 3,4-dihydroxyphenylalanine (DOPA) analogues as well as a metabolite of Hydroxytyrosol (H977000).

REFERENCES

• Mathieu, P. et al.: Bull. Soc. Chim. Biol., 52, 1039 (1970)
• Goodwin, B.L. et al.: Xenobiotica, 8, 629 (1970)
• Tuck, K.L. et al.: J. Agric. Food Chem., 50, 2404 (1970)