3,4-dihydroxybenzoic acid

• ChemBase ID: 3581
• Molecular Formular: C7H6O4
• Molecular Mass: 154.12014
• Monoisotopic Mass: 154.02660867
• SMILES: OC(=O)c1ccc(O)c(O)c1
• Canonical SMILES: OC(=O)c1ccc(c(c1)O)O
• InChI: InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
• InChIKey: YQUVCSBJEUQKSH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4-dihydroxybenzoic acid
• IUPAC Traditional name: 3,4-dihydroxybenzoic acid
• Synonyms: PCA; 3,4-Dihydroxybenzoic acid; 3,4-Dihydroxybenzoic Acid; 1,2-Dihydroxybenzene-4-carboxylic Acid; 4,5-Dihydroxybenzoic Acid; 4-Carboxy-1,2-dihydroxybenzene; NSC 16631; Protocatechoic Acid; Protocatechuic acid; 3,4-Dihydroxybenzoic acid; PROTOCATECHUIC ACID; 原儿茶酸; 3,4-二羟基苯甲酸

Database IDs

• CAS Number: 99-50-3
• EC Number: 202-760-0
• MDL Number: MFCD00002509
• Beilstein Number: 1448841
• Merck Index: 147894
• PubChem SID: 24863405; 160967019; 46505638
• PubChem CID: 72
• CHEBI ID: 36062
• CHEMBL: 37537
• Chemspider ID: 71
• DrugBank ID: DB03946
• Wikipedia Title: Protocatechuic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.160229
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.3327449
• LogD (pH = 7.4): -2.0405138
• Log P: 1.0236981
• Molar Refractivity: 37.276 cm^3
• Polarizability: 13.965821 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.32
• LOG S: -1.1
• Solubility (Water): 1.24e+01 g/l

PROPERTIES

Physical Property

• Apperance: Powder
• Melting Point: 197-200 °C (dec.)(lit.); 197-202°C; ca 202°C dec.
• pKa: 4.48

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: Air Sensitive; IRRITANT
• RTECS: UL0560000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 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: ≥97.0% (HPLC); ≥97.0% (T); 95+%; 97%
• Grade: analytical standard
• Shelf Life: (limited shelf life, expiry date on the label)
• Linear Formula: (HO)2C6H3CO2H
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 05205667

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02156421

Crystalline

DrugBank - DB03946

Drug information: experimental

Sigma Aldrich - P5630

Biochem/physiol Actions
几个致癌作用的动物模型中的化学防癌剂。在后启动阶段阻断细胞增殖。

Sigma Aldrich - 37580

Biochem/physiol Actions
Chemopreventive in several animal models of carcinogenesis. Blocks cell proliferation in the post-initiation phase.
Packaging
25, 100 g in glass bottle

Sigma Aldrich - 08992

Biochem/physiol Actions
Chemopreventive in several animal models of carcinogenesis. Blocks cell proliferation in the post-initiation phase.

Sigma Aldrich - D109800

Biochem/physiol Actions
Chemopreventive in several animal models of carcinogenesis. Blocks cell proliferation in the post-initiation phase.

Toronto Research Chemicals - D451680

3,4-Dihydroxybenzoic Acid is a metabolite of polyphenols such as Phloretin (P339000) and Quercetin (Q509500).

REFERENCES

• Vaidyanathan, J., et al.: Drug Metab. Dispos., 30, 897 (2002)
• Wolfe, K., et al.: J. Agric. Food Chem., 51, 609 (2002)
• Marks, S., et al.: J. Agric Food. Chem., 55, 8723 (2002)