2-{2-[(2,6-dichloro-4-hydroxyphenyl)amino]phenyl}acetic acid

• ChemBase ID: 155592
• Molecular Formular: C14H11Cl2NO3
• Molecular Mass: 312.14804
• Monoisotopic Mass: 311.01159858
• SMILES: c1ccc(c(c1)CC(=O)O)Nc1c(cc(cc1Cl)O)Cl
• Canonical SMILES: OC(=O)Cc1ccccc1Nc1c(Cl)cc(cc1Cl)O
• InChI: InChI=1S/C14H11Cl2NO3/c15-10-6-9(18)7-11(16)14(10)17-12-4-2-1-3-8(12)5-13(19)20/h1-4,6-7,17-18H,5H2,(H,19,20)
• InChIKey: KGVXVPRLBMWZLG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[(2,6-dichloro-4-hydroxyphenyl)amino]phenyl}acetic acid
• IUPAC Traditional name: 4'-hydroxydiclofenac
• Synonyms: 2-[(2,6-Dichloro-4-hydroxyphenyl)amino]benzeneacetic Acid; 4'-Hydroxydiclofenac; 4'-Hydroxy Diclofenac; 4′-Hydroxy Diclofenac; [2-(2,6-Dichloro-4-hydroxy-phenylamino)phenyl]acetic acid; 4′-Hydroxydiclofenac; 2-((2,6-二氯-4-羟基苯基)氨基)苯乙酸; 4′-羟基双氯灭痛; 4′-羟基双氯芬酸

Database IDs

• CAS Number: 64118-84-9
• MDL Number: MFCD01671980
• Beilstein Number: 4198042
• PubChem SID: 162249730; 24895589
• PubChem CID: 116545

CALCULATED PROPERTIES

• Acid pKa: 3.7610223
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.215171
• LogD (pH = 7.4): 0.64987373
• Log P: 3.9554439
• Molar Refractivity: 77.4423 cm^3
• Polarizability: 29.690742 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Light Violet Solid
• Melting Point: 178-185°C dec.

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under inert atmosphere
• RTECS: AG6542800
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25-37/38-41-50/53
• Safety Statements: 26-39-45-60-61
• GHS Pictograms: GHS05; GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H318-H335-H410
• GHS Precautionary statements: P261-P273-P280-P301 + P310-P305 + P351 + P338-P501
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Grade: VETRANAL™, analytical standard
• Packaging: vial of 5 mg
• Empirical Formula (Hill Notation): C14H11Cl2NO3

DETAILS

Sigma Aldrich - H3661

Application
Used for determining CYP2C9 activity, see Cytochrome P450 isozymes.
General description
CYP2C9 metabolite of diclofenac.

Sigma Aldrich - 32412

General description
CYP2C9 metabolite of diclofenac.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - H825225

Diclofenac-13C6 Sodium Salt13C Labelled Diclofenac Sodium Salt is a known nonsteroidal anti-inflammatory compound and cyclooxygenase (COX) inhibitor.

REFERENCES

• Kretz-Rommel, A., et al.: Toxicol. Appl. Pharmacol., 120, 155 (1993)
• Petronilli, V., et al.: J. Biol. Chem., 269, 16638 (1993)
• Bort, R., et al.: J. Pharmacol. Exp. Ther., 288, 65 (1993)
• Poon, G., et al.: Drug Metab. Dispos., 29, 1608 (1993)