4-acetamidobenzoic acid

• ChemBase ID: 4073
• Molecular Formular: C9H9NO3
• Molecular Mass: 179.17266
• Monoisotopic Mass: 179.05824315
• SMILES: CC(=O)Nc1ccc(cc1)C(=O)O
• Canonical SMILES: CC(=O)Nc1ccc(cc1)C(=O)O
• InChI: InChI=1S/C9H9NO3/c1-6(11)10-8-4-2-7(3-5-8)9(12)13/h2-5H,1H3,(H,10,11)(H,12,13)
• InChIKey: QCXJEYYXVJIFCE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-acetamidobenzoic acid
• IUPAC Traditional name: 4-acetamidobenzoic acid
• Synonyms: 4-Acetamidobenzoic acid; N-Acetyl-PABA; p-Acetamidobenzoic acidp-Acetaminobenzoic acid; p-Acetoaminobenzoic acid; Acedoben; NSC 4002; p-(Acetoamino)benzoic Acid; p-(Acetylamino)benzoic Acid; p-ACETAMINOBENZOIC ACID; Para acetamido benzoic acid; Acedoben; p-Acetamidobenzoic acid; 4-Carboxyacetanilide; PAAB; 4-Acetamidobenzoic acid; N-Acetyl-PABA; p-Acetaminobenzoic acid; p-Acetoaminobenzoic acid; 4'-Carboxyacetanilide; 4-Acetylaminobenzoic acid; p-Acetylaminobenzoic acid; Acedoben [INN-Spanish]; Acedobene [INN-French]; Acedobenum [INN-Latin]; 4-(Acetylamino)benzoic acid; N-Acetyl-p-aminobenzoic acid; PAcBA; 4-acetamidobenzoic acid; 对乙酰氨基苯甲酸; 4-乙酰氨基苯甲酸

Database IDs

• CAS Number: 556-08-1
• EC Number: 209-114-7
• MDL Number: MFCD00002534
• Beilstein Number: 390602
• PubChem SID: 46507151; 24848102; 24844993; 160967507
• PubChem CID: 19266
• CHEMBL: 112687
• Chemspider ID: 18177
• DrugBank ID: DB04500
• Wikipedia Title: Acedoben

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.161065
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.4870615
• LogD (pH = 7.4): -2.1910276
• Log P: 0.8685391
• Molar Refractivity: 48.1772 cm^3
• Polarizability: 17.573618 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.14
• LOG S: -2.12
• Solubility (Water): 1.36e+00 g/l

PROPERTIES

Physical Property

• Melting Point: 255-262(dec.)°C; 259-262 °C (dec.); 259-262 °C (dec.)(lit.); ca 261°C dec.
• Hydrophobicity(logP): 1.31 [HANSCH,C ET AL. (1995)]

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26-37; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (T); 95+%; 98%
• Grade: purum
• Linear Formula: CH3CONHC6H4CO2H

DETAILS

MP Biomedicals - 05207587

MP Biomedicals Rare Chemical collection

DrugBank - DB04500

Drug information: experimental

Sigma Aldrich - 133337

Packaging
25 g in poly bottle

Toronto Research Chemicals - A130500

Acedoben is the acetylated derivative of p-aminobenzoic acid (PABA). Acedoben is a metabolite of the anesthetic Benzocaine (B202970).

REFERENCES

• Song, D.-J. et al.: Biopharm. Drug Dispos., 20, 263 (1999)
• Hayton, W.L. et al.: Aquat. Toxicol., 36, 99 (1999)