4-hydroxy-4-methyloxan-2-one

• ChemBase ID: 137926
• Molecular Formular: C6H10O3
• Molecular Mass: 130.1418
• Monoisotopic Mass: 130.06299418
• SMILES: CC1(CCOC(=O)C1)O
• Canonical SMILES: O=C1OCCC(C1)(C)O
• InChI: InChI=1S/C6H10O3/c1-6(8)2-3-9-5(7)4-6/h8H,2-4H2,1H3
• InChIKey: JYVXNLLUYHCIIH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-4-methyloxan-2-one
• IUPAC Traditional name: 4-hydroxy-4-methyloxan-2-one
• Synonyms: DL-Mevalolactone; DL-Mevalonic acid lactone; (±)-Mevalonolactone; (±)-Mevalonic acid lactone; β-Hydroxy-β-methyl-δ-valerolactone; (±)-β-Hydroxy-β-methyl-δ-valerolactone; (±)-Mevalolactone; (±)-Mevalonolactone; (±)-3-Hydroxy-3-methyl δ-valerolactone; Mevalonic lactone; Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-one; D,L-β-Hydroxy-β-methyl-δ-valerolactone; DL-Mevalonolactone; Mevalonic lactone; Mevalonolactone; NSC 90804; D,L-Mevalonic Acid Lactone; (±)-甲瓦龙酸内酯; β-羟基-β-甲基-δ-戊内酯; (±)-β-羟基-β-甲基-δ-戊内酯; (±)-3-羟基-3-甲基 δ-戊内酯; (±)-甲瓦龙酸内酯; (±)-甲羟戊酸内酯; 甲瓦龙酸内酯

Database IDs

• CAS Number: 674-26-0
• EC Number: 211-615-0
• MDL Number: MFCD00006648
• Beilstein Number: 80960
• PubChem SID: 24896934; 162232186
• PubChem CID: 10428

CALCULATED PROPERTIES

• Acid pKa: 14.71489
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.42890844
• LogD (pH = 7.4): -0.42890847
• Log P: -0.42890844
• Molar Refractivity: 31.0192 cm^3
• Polarizability: 12.506425 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethanol; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Oil
• Melting Point: 24-27 °C; 28 °C(lit.)
• Boiling Point: 145-150 °C/5 mmHg(lit.)
• Flash Point: 113 °C; 235.4 °F
• Refractive Index: n20/D 1.473(lit.)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Storage Warning: Hygroscopic
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ~97% (titration); ≥96.0% (T); 97%
• Grade: purum
• Impurities: salt, none detected
• Empirical Formula (Hill Notation): C6H10O3

DETAILS

Sigma Aldrich - M4667

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Other Notes
May also be liquid!
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M4667.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Packaging
1, 5, 10 g in glass bottle

Sigma Aldrich - 286702

Other Notes
Contains mevalonic acid

Sigma Aldrich - 69761

Caution
can form fused mass at low temperatures
Other Notes
Lactone of mevalonic acid which is a very important connecting link in the biosynthesis of isoprenoids1,2,3,4

Toronto Research Chemicals - M339025

A metabolite from endophytes of the medicinal plant Erythrina crista-galli.

REFERENCES

• Stadler, M., et al.: Planta Med., 60, 128 (1994)
• Kopcke, B., et al.: Phytochemistry, 60, 709 (1994)
• Chu, M., et al.: J. Nat. Prod., 66, 1527 (1994)
• Weber, D., et al.: J. Antibiot., 57, 559 (1994)