(2S)-2-(6-hydroxynaphthalen-2-yl)propanoic acid

• ChemBase ID: 154331
• Molecular Formular: C13H12O3
• Molecular Mass: 216.23258
• Monoisotopic Mass: 216.07864424
• SMILES: C[C@@H](c1ccc2cc(ccc2c1)O)C(=O)O
• Canonical SMILES: OC(=O)[C@H](c1ccc2c(c1)ccc(c2)O)C
• InChI: InChI=1S/C13H12O3/c1-8(13(15)16)9-2-3-11-7-12(14)5-4-10(11)6-9/h2-8,14H,1H3,(H,15,16)/t8-/m0/s1
• InChIKey: XWJUDDGELKXYNO-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(6-hydroxynaphthalen-2-yl)propanoic acid
• IUPAC Traditional name: (2S)-2-(6-hydroxynaphthalen-2-yl)propanoic acid
• Synonyms: (S)-6-Hydroxy-α-methyl-2-naphthaleneacetic acid; d-2-(6-Hydroxy-2-naphthyl)proprionic acid; O-Desmethylnaproxen; (αS)-6-Hydroxy-α-methyl-2-naphthaleneacetic Acid; (S)-2-(6-Hydroxy-2-naphthyl)propionic Acid; (S)-6-O-Desmethylnaproxen; (S)-6-Demethylnaproxen; (S)-O-Desmethyl Naproxen

Database IDs

• CAS Number: 52079-10-4
• MDL Number: MFCD00869765
• Beilstein Number: 8838512
• PubChem SID: 162248470
• PubChem CID: 13393711

CALCULATED PROPERTIES

• Acid pKa: 4.3397193
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.6524085
• LogD (pH = 7.4): -0.095613755
• Log P: 2.839892
• Molar Refractivity: 60.3712 cm^3
• Polarizability: 24.46766 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO; Ethyl Acetate; Methanol
• Apperance: Off-Whie to Pale Pink Solid; white
• Melting Point: 182-183 °C; 188-190°C

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Nature polluting (N); Harmful (Xn)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 22-43-50/53
• Safety Statements: 36/37-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H317-H400
• GHS Precautionary statements: P273-P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 3077 9/PG 3
• Storage Temperature: 2-8°C

Product Information

• Empirical Formula (Hill Notation): C13H12O3

DETAILS

Sigma Aldrich - UC305

Biochem/physiol Actions
CYP2C9 metabolite of naproxen

Toronto Research Chemicals - D292125

A metabolite of Naproxen.

REFERENCES

• Bonnabry, P., et al.: Eur. J. Clin. Pharmacol., 49, 305 (1992)
• Rao, S., et al.: J. Med. Chem., 43, 2789 (1992)
• Hutzler, J., et al.: Drug Meta
• Rettie, A., et al.: Chem. Res. Toxicol., 5, 54 (1992)
• Tracy, T., et al.: Biochem. Pharmacol., 52, 1305 (1992)