4-hydroxy-6-methyl-2H-pyran-2-one

• ChemBase ID: 69459
• Molecular Formular: C6H6O3
• Molecular Mass: 126.11004
• Monoisotopic Mass: 126.03169405
• SMILES: c1(=O)cc(cc(o1)C)O
• Canonical SMILES: Oc1cc(C)oc(=O)c1
• InChI: InChI=1S/C6H6O3/c1-4-2-5(7)3-6(8)9-4/h2-3,7H,1H3
• InChIKey: NSYSSMYQPLSPOD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-6-methyl-2H-pyran-2-one
• IUPAC Traditional name: 4-hydroxy-6-methylpyran-2-one; triacetic acid lactone
• Synonyms: 3,5-Dihydroxysorbic acid δ-lactone; 4-Hydroxy-6-methyl-2-pyrone; 4-hydroxy-6-methyl-2H-pyran-2-one; 3,5-Dihydroxysorbic acid delta-lactone; 4-Hydroxy-6-methyl-2-oxo-2H-pyran; 4-Hydroxy-6-methyl-2-pyrone; 4-Hydroxy-6-methyl-2H-pyran-2-one 98%; 4-Hydroxy-6-methyl-2-pyrone; Triacetate lactone; 3,5-Dihydroxysorbic acid δ-lactone;4-Hydroxy-6-Methyl-2-Pyrone; 4-Hydroxy-6-Methyl-a-pyrone;; Triacetic acid lactone; 3,5-二羟基山梨酸 δ-内酯; 4-羟基-6-甲基-2-吡喃酮

Database IDs

• CAS Number: 675-10-5
• EC Number: 211-619-2
• MDL Number: MFCD00006641
• Beilstein Number: 113815
• PubChem SID: 162035185; 24879748; 24895638
• PubChem CID: 54675757
• Chemspider ID: 10229807
• Wikipedia Title: Triacetic_acid_lactone

CALCULATED PROPERTIES

• Acid pKa: 7.667549
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.5461397
• LogD (pH = 7.4): 0.36161023
• Log P: 0.5490816
• Molar Refractivity: 33.8069 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

• Solubility: 8.60 g L-1 at 20°C in H₂O
• Apperance: light yellow crystal powder
• Melting Point: 188-190 °C; 188-190 °C (dec.)(lit.); 188-190(dec.)°C; ca 186°C dec.
• Boiling Point: 285.9 °C
• Flash Point: 127.9 °C
• Density: 1.348 g cm^-3

Safety Information

• Storage Warning: IRRITANT; Irritant
• RTECS: UQ1000000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• Main Hazard: Moderately Toxic
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (CH); 95+%; 98%
• Grade: purum
• Empirical Formula (Hill Notation): C6H6O3
• Classification: Genuine Natural Compounds

DETAILS

Sigma Aldrich - H43415

Packaging
5, 25 g in glass bottle

REFERENCES

• Can participate in annulation reactions, due to the relatively high acidity of the C-H bond at the 3-position: a three-component reaction with isocyanides and dialkyl acetylene dicarboxylates affords annulated 4H-pyrans: Tetrahedron, 62, 3016 (2006). For reaction scheme, see: tert-Butyl isocyanide, L19747.