2-(2,5-dihydroxyphenyl)acetic acid

• ChemBase ID: 5950
• Molecular Formular: C8H8O4
• Molecular Mass: 168.14672
• Monoisotopic Mass: 168.04225874
• SMILES: C(=O)(Cc1cc(O)ccc1O)O
• Canonical SMILES: OC(=O)Cc1cc(O)ccc1O
• InChI: InChI=1S/C8H8O4/c9-6-1-2-7(10)5(3-6)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
• InChIKey: IGMNYECMUMZDDF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(2,5-dihydroxyphenyl)acetic acid
• IUPAC Traditional name: homogentisic acid
• Synonyms: Homogentisic acid; 2,5-DIHYDROXYPHENYLACETIC ACID (LACTONE); 2,5-Dihydroxyphenylacetic acid; HOMOGENTISIC ACID FREE ACID; Homogentisic acid; 2,5-Dihydroxyphenylacetic acid; 2-(3,6-DIHYDROXYPHENYL)ACETIC ACID; Melanic acid; Homogentisic acid; 2,5-Dihydroxybenzeneacetic Acid; 2,5-Dihydroxy-α-toluic Acid; Alcapton; Homogentisinic Acid; NSC 88940; 2,5-二羟基苯乙酸; 尿黑酸

Database IDs

• CAS Number: 451-13-8
• EC Number: 207-192-7
• MDL Number: MFCD00004324
• Beilstein Number: 2692860
• PubChem SID: 24895411; 99444798; 24878091; 160969375
• PubChem CID: 780
• CHEBI ID: 44747
• Chemspider ID: 759
• DrugBank ID: DB08327
• KEGG ID: C00544
• MeSH Name: Homogentisic+acid
• Wikipedia Title: Homogentisic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.5738041
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.91679174
• LogD (pH = 7.4): -2.351075
• Log P: 1.0038635
• Molar Refractivity: 41.3274 cm^3
• Polarizability: 15.806307 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.81
• LOG S: -1.32
• Solubility (Water): 8.10e+00 g/l

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: off-white to tan crystalline; White Solid
• Melting Point: 150 - 152°C; 150-152 °C(lit.); 150-152°C; 150-152°C

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• RTECS: AH0589000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• TSCA Listed: 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-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (GC); 97%
• Grade: purum
• Linear Formula: (HO)2C6H3CH2CO2H

DETAILS

MP Biomedicals - 02101980

Free Acid
Off-white to tan crystals

MP Biomedicals - 05202023

MP Biomedicals Rare Chemical collection

DrugBank - DB08327

Drug information: experimental

Toronto Research Chemicals - H593400

An intermediate in the metabolism of tyrosine and phenylalanine. Occurs in plants and in the urine of alkaptonurics.

Sigma Aldrich - H0751

包装
100, 500 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. H0751.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Knox, W.E., et al.: Biochem. J., 49, 686 (1951)
• LaDu, B.N., et al.: J. Biol. Chem., 217, 777 (1955)