2-(3,4-dihydroxyphenyl)acetic acid

• ChemBase ID: 1476
• Molecular Formular: C8H8O4
• Molecular Mass: 168.14672
• Monoisotopic Mass: 168.04225874
• SMILES: c1(cc(c(cc1)O)O)CC(=O)O
• Canonical SMILES: OC(=O)Cc1ccc(c(c1)O)O
• InChI: InChI=1S/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
• InChIKey: CFFZDZCDUFSOFZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(3,4-dihydroxyphenyl)acetic acid
• IUPAC Traditional name: 3,4 dihydroxyphenylacetic acid
• Synonyms: DOPAC; Homoprotocatechuic acid; 3,4-DIHYDROXYPHENYLACETIC ACID; 3,4-Dihydroxyphenylacetic acid; 3,4-Dihydroxybenzeneacetic Acid; (3,4-Dihydroxyphenyl)acetic Acid; Ba 2773; Dihydroxyphenylacetic Acid; Dopacetic Acid; 2-(3,4-Dihydroxyphenyl)Acetic Acid; 高原儿茶酸; 3,4-二羟基苯乙酸

Database IDs

• CAS Number: 102-32-9
• EC Number: 203-024-1
• MDL Number: MFCD00004338
• Beilstein Number: 2211017
• PubChem SID: 160964935; 46507886; 24888293
• PubChem CID: 547
• CHEBI ID: 41941
• CHEMBL: 1284
• Chemspider ID: 532
• DrugBank ID: DB01702
• MeSH Name: 3,4-Dihydroxyphenylacetic+Acid
• Wikipedia Title: 3,4-Dihydroxyphenylacetic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6084359
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.88342446
• LogD (pH = 7.4): -2.3416903
• Log P: 1.0038635
• Molar Refractivity: 41.3274 cm^3
• Polarizability: 15.808369 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.93
• LOG S: -1.37
• Solubility (Water): 7.23e+00 g/l

PROPERTIES

Physical Property

• Melting Point: 127- 130°C; 127-130 °C(lit.); 128-130°C; 128-132 °C
• Hydrophobicity(logP): 0.98 [SANGSTER (1994)]

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: AH0590000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• 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: ≥98.0% (T); 97%; 98%; 98+%
• Grade: purum
• Linear Formula: (HO)2C6H3CH2CO2H

DETAILS

MP Biomedicals - 02101568

Free Acid
Purity: 98% (NaOH Titration)
White to off-white crystals.

MP Biomedicals - 05214576

MP Biomedicals Rare Chemical collection

DrugBank - DB01702

• Drug Groups: experimental
• Description: A deaminated metabolite of levodopa. [PubChem]

Sigma Aldrich - 850217

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - D454250

3,4-Dihydroxyphenylacetic Acid is a metabolite of Dopamine (D533782).

REFERENCES

• Johnson, S. et al.: J. Physiol., 450, 455 (1992)
• Kolesnikov, Y. et al.: Eur. J. Pharmacol., 296, 17 (1992)
• Leshner, A. et al.: Science, 278, 45 (1992)
• Li, J. et al.: Acta Pharmacol. Sin., 20, 375 (1992)
• Gibson, D. et al.: Brain Res., 952, 71 (1992)
• V