5-hydroxy-2-methyl-4H-pyran-4-one

• ChemBase ID: 159657
• Molecular Formular: C6H6O3
• Molecular Mass: 126.11004
• Monoisotopic Mass: 126.03169405
• SMILES: c1c(c(=O)cc(o1)C)O
• Canonical SMILES: Cc1occ(c(=O)c1)O
• InChI: InChI=1S/C6H6O3/c1-4-2-5(7)6(8)3-9-4/h2-3,8H,1H3
• InChIKey: IQXWFHDFTAZGNB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-2-methyl-4H-pyran-4-one
• IUPAC Traditional name: 5-hydroxy-2-methylpyran-4-one
• Synonyms: 5-hydroxy-2-methyl-4H-pyran-4-one; 5-Hydroxy-2-methyl-4H-pyran-4-one; 2-Methyl-5-hydroxy-(4H)-pyran-4-one; 2-Methyl-5-hydroxy-1,4-pyrone; 3-Hydroxy-6-methyl-4-pyrone; 5-Hydroxy-2-methyl-γ-pyrone; α-Deoxykojic Acid; NSC 166902; Allo Maltol

Database IDs

• CAS Number: 644-46-2
• MDL Number: MFCD04125897
• PubChem SID: 162253792
• PubChem CID: 69521

CALCULATED PROPERTIES

• Acid pKa: 9.561099
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.5463902
• LogD (pH = 7.4): 0.54344213
• Log P: 0.5464279
• Molar Refractivity: 33.722 cm^3
• Polarizability: 12.004696 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: N/A

DETAILS

Toronto Research Chemicals - A546700

The esters of 5-hydroxy-2-methyl-4H-pyran-4-one are used as novel tyrosinase inhibitors for skin-lightening cosmetic compositions.

REFERENCES

• Ogino, H., et al.: J. Antibiot., 43, 174 (1990)
• Weinberg, G., et al.: Antimicrob. Agents Chemother., 38, 997 (1990)
• Skaar, E., et al.: J. Bacteriol., 188, 1071 (1990)