5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

• ChemBase ID: 1532
• Molecular Formular: C6H6O4
• Molecular Mass: 142.10944
• Monoisotopic Mass: 142.02660867
• SMILES: OCc1cc(=O)c(O)co1
• Canonical SMILES: OCc1occ(c(=O)c1)O
• InChI: InChI=1S/C6H6O4/c7-2-4-1-5(8)6(9)3-10-4/h1,3,7,9H,2H2
• InChIKey: BEJNERDRQOWKJM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one
• IUPAC Traditional name: kojic acid
• Synonyms: 5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one; 5-Hydroxy-2-hydroxymethyl-4H-pyran-4-one; 5-Hydroxy-2-hydroxymethyl-4-pyrone; 5-Hydroxy-2-(hydroxymethyl)-4H-pyranone; 2-(Hydroxymethyl)-5-hydroxy-4H-pyran-4-one; NSC 1942; 5-Hydroxy-2-hydroxymethyl-4H-4-pyranone; Kojic acid; Kojic acid; 5-Hydroxy-2-(hydroxymethyl)-4-pyrond; 2-Hydroxymethyl-5-hydroxy-γ-pyrone; 2-Hydroxymethyl-5-hydroxy-β-pyrone; KOJIC ACID; 5-Hydroxy-2-(Hydroxymethyl)-4h-Pyran-4-One; 曲酸

Database IDs

• CAS Number: 501-30-4
• EC Number: 207-922-4
• MDL Number: MFCD00006580
• Beilstein Number: 120895
• Merck Index: 145317
• PubChem SID: 24882002; 46506760; 160964989; 24896226
• PubChem CID: 3840
• CHEBI ID: 43572
• CHEMBL: 287556
• Chemspider ID: 3708
• DrugBank ID: DB01759
• KEGG ID: C14516
• Unique Ingredient Identifier: 6K23F1TT52
• Wikipedia Title: Kojic_acid

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.301323
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.5005506
• LogD (pH = 7.4): -0.50589734
• Log P: -0.500482
• Molar Refractivity: 35.2657 cm^3
• Polarizability: 12.693242 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.02
• LOG S: -0.19
• Solubility (Water): 9.23e+01 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Slight in water
• Apperance: Off-White to Tan Solid; white
• Melting Point: 140-142°C; 152 - 155 °C; 152-155 °C(lit.); 152-155°C; 152-155°C; 153-156 °C
• Hydrophobicity(logP): -0.64 [KONTOGHIORGHES,GJ (1988)]
• pKa: 9.40

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C)
• RTECS: UQ0875000
• European Hazard Symbols: X
• German water hazard class: 3
• Risk Statements: 40; R36/37/38
• Safety Statements: 36/37; S22, S24/25
• TSCA Listed: 否
• GHS Pictograms: GHS08
• GHS Hazard statements: H351
• GHS Precautionary statements: P281-P201-P202-P308+P313-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (HPLC); 97%; 98%; 99%
• Grade: purum
• Empirical Formula (Hill Notation): C6H6O4
• Classification: Genuine Natural Compounds

DETAILS

MP Biomedicals - 02155157

(2-Hydroxymethyl-5-hydroxy-γ-pyrone) Crystalline

DrugBank - DB01759

Drug information: experimental

Sigma Aldrich - K3125

Biochem/physiol Actions
Tyrosinase inhibitor.
包装
5, 10, 25 g in poly bottle

Sigma Aldrich - 60890

Biochem/physiol Actions
Tyrosinase inhibitor.

Toronto Research Chemicals - K655080

A naturally occurring chelation agent.

REFERENCES

• Boonme, P., et al.: J. Biomed. Nanotechnol., 5, 373 (2009)
• Noh, J., et al.: Bioorg. Med. Chem., Lett., 19, 5586 (2009)
• Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2009)