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

• ChemBase ID: 6688
• Molecular Formular: C9H10O4
• Molecular Mass: 182.1733
• Monoisotopic Mass: 182.0579088
• SMILES: c1c(c(cc(c1)CC(=O)O)OC)O
• Canonical SMILES: COc1cc(ccc1O)CC(=O)O
• InChI: InChI=1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
• InChIKey: QRMZSPFSDQBLIX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(4-hydroxy-3-methoxyphenyl)acetic acid
• IUPAC Traditional name: homovanillic acid
• Synonyms: 4-Hydroxy-3-methoxyphenylacetic acid; HVA; HOMOVANILLIC ACID; 4-Hydroxy-3-methoxyphenylacetic acid; 4-Hydroxy-3-(methoxy)benzeneacetic Acid; 4-Hydroxy-3-(methoxy)phenylacetic Acid; 3-(Methoxy)-4-hydroxyphenylacetic Acid; NSC 16682; Vanilacetic Acid; Homovanillic acid; Homovanillic acid; 高香草酸

Database IDs

• CAS Number: 306-08-1
• EC Number: 206-176-7
• MDL Number: MFCD00004350
• Beilstein Number: 2213447
• Merck Index: 144740
• PubChem SID: 24277895; 160969995
• PubChem CID: 1738
• CHEBI ID: 545959
• CHEMBL: 1562
• Chemspider ID: 1675
• KEGG ID: C05582
• MeSH Name: Homovanillic+acid
• Wikipedia Title: Homovanillic_acid

CALCULATED PROPERTIES

• Acid pKa: 3.744857
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.60572475
• LogD (pH = 7.4): -2.1383011
• 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

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 140-145°C; 141-142°C; 142-143 °C; 142-145 °C(lit.); 142-145°C; 143-145?C

Safety Information

• Storage Condition: -20°C, Desiccate, Protect from light; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: true; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥99.0% (HPLC); 97%; 98+%
• Impurities: ≤0.3% vanillic acid
• Linear Formula: HOC6H3(OCH3)CH2CO2H

DETAILS

MP Biomedicals - 02101984

Used in determination of enzymes (e.g. glucose oxidase). Also a metabolite of epinephrine and arterenol.

Sigma Aldrich - H1252

Biochem/physiol Actions
Metabolite of dihydroxyphenylacetic acid (DOPAC) by catechol O-methyltransferase; reagent for the fluorimetric determination of glucose oxidase and other oxidative enzymes
包装
1 g in poly bottle
100, 250 mg in poly bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H1252.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 53620

Other Notes
Metabolite of adrenalin and arterenol; reagent for the fluorometric determination of glucose oxidase, peroxidase and xanthine oxidase1; Determination of amino acids2

Toronto Research Chemicals - H669500

A neuroendocrine tumor marker. Dihydroxyphenylacetic Acid (DOPAC) metabolite.

REFERENCES

• Yamamoto, K., et al.: J. Clin. Oncol., 16, 1265 (1998)
• Meijer, W., et al.: Clin. Chem., 46, 1588 (1998)
• Ilias, I., et al.: Horm. Metab. Res., 37, 717 (1998)
• Boyle, J., et al.: J. Clin. Endocrinol. Metab., 92, 4602 (1998)
• Reagent for the determination of enzymes: Anal. Chem., 40, 190 (1968), and amino acids: Anal. Biochem., 26, 1 (1968).