2-(7-hydroxy-2-oxo-2H-chromen-4-yl)acetic acid

• ChemBase ID: 10060
• Molecular Formular: C11H8O5
• Molecular Mass: 220.17822
• Monoisotopic Mass: 220.03717336
• SMILES: C(C(=O)O)c1c2c(oc(=O)c1)cc(cc2)O
• Canonical SMILES: OC(=O)Cc1cc(=O)oc2c1ccc(c2)O
• InChI: InChI=1S/C11H8O5/c12-7-1-2-8-6(3-10(13)14)4-11(15)16-9(8)5-7/h1-2,4-5,12H,3H2,(H,13,14)
• InChIKey: BNHPMQBVNXMPDU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(7-hydroxy-2-oxo-2H-chromen-4-yl)acetic acid
• IUPAC Traditional name: (7-hydroxy-2-oxochromen-4-yl)acetic acid
• Synonyms: (7-Hydroxycoumarin-4-yl)acetic acid; 7-Hydroxycoumarin-4-acetic acid; 4-(Carboxymethyl)umbelliferone; 7-Hydroxy-4-coumarinylacetic acid; 7-Hydroxycoumarin-4-acetic acid; 7-Hydroxy-2-oxo-2H-1-benzopyran-4-acetic Acid; NSC 642907; NSC 65625; Umbelliferone-4-acetic acid; 7-Hydroxycoumarinyl-4-acetic acid; 伞形酮-4-乙酸; 7-羟基香豆素-4-乙酸

Database IDs

• CAS Number: 6950-82-9
• MDL Number: MFCD00037563
• Beilstein Number: 204777
• PubChem SID: 24879227; 160973367; 24860338
• PubChem CID: 5338490

CALCULATED PROPERTIES

• Acid pKa: 3.431163
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.1564078
• LogD (pH = 7.4): -2.638008
• Log P: 0.9035158
• Molar Refractivity: 54.0779 cm^3
• Polarizability: 20.591148 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble; H2O: soluble (pH ≥ 6)
• Melting Point: >195°C(dec); >195(dec.)°C; 194-196 °C(lit.); 212 °C (dec.)(lit.)
• pKa: 7.8
• Fluorescence: λex 367 nm; λem 455 nm in 0.1 M Tris pH 9.0

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (TLC); 97%
• Grade: for fluorescence
• Empirical Formula (Hill Notation): C11H8O5
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 335665

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 55157

Application
suitable as pH indicator

Toronto Research Chemicals - H825135

Fluorogenic substrate

REFERENCES

• Manvar, A., et al.: Eur. J. Med. Chem., 43, 2395 (2008)
• Holmes, C., et al.: Bioorg. Med. Chem. Lett., 18, 3382 (2008)