(3R)-3-hydroxy-4,4-dimethyloxolan-2-one

• ChemBase ID: 110070
• Molecular Formular: C6H10O3
• Molecular Mass: 130.1418
• Monoisotopic Mass: 130.06299418
• SMILES: CC1(C)COC(=O)[C@@H]1O
• Canonical SMILES: O[C@H]1C(=O)OCC1(C)C
• InChI: InChI=1S/C6H10O3/c1-6(2)3-9-5(8)4(6)7/h4,7H,3H2,1-2H3/t4-/m0/s1
• InChIKey: SERHXTVXHNVDKA-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-hydroxy-4,4-dimethyloxolan-2-one
• IUPAC Traditional name: pantolactone
• Synonyms: D-(-)-Pantolactone; D-α-HYDROXY-β,β-DIMETHYL-γ-BUTYROLACTONE; (R)-(-)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; (R)-(-)-β,β-Dimethyl-α-hydroxy-γ-butyrolactone; (R)-(-)-Pantolactone; Pantoic acid γ-lactone; (R)-(-)-4,5-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone; D-(-)-alpha-Hydroxy-beta,beta-dimethyl-gamma-butyrolactone; (3R)-Dihydro-3-hydroxy-4,4-dimethyl-2(3H)-furanone; (-)-(R)-Pantolactone; (-)-2-Hydroxy-3,3-dimethyl-γ-butyrolactone; (-)-Pantoyl Lactone; (3R)-Tetrahydro-3-hydroxy-4,4-dimethylfuran-2-one; Pantothenic Lactone; D-(-)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; (R)-α-Hydroxy-β,β-dimethyl-γ-butyrolactone; D-(-)-Pantolactone; (R)-(-)-α-羟基-β,β-二甲基-γ-丁内酯; (R)-(-)-β,β-二甲基-α-羟基-γ-丁内酯; (R)-(-)-泛内酯; 泛解酸γ-内酯; D-(-)-泛酰内酯

Database IDs

• CAS Number: 599-04-2
• EC Number: 209-963-3
• MDL Number: MFCD00005392
• Beilstein Number: 80957
• Merck Index: 147013
• PubChem SID: 24854272; 24879245; 162096418
• PubChem CID: 439368

CALCULATED PROPERTIES

• Acid pKa: 12.228233
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.17736644
• LogD (pH = 7.4): 0.17736007
• Log P: 0.17736652
• Molar Refractivity: 30.516 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

• Melting Point: 89-91°C; 89-92 °C; 91 °C(lit.)
• Boiling Point: 120-122 °C/15 mmHg(lit.); 120-122°C/15mm
• Optical Rotation: [α]20/D -51±2°, c = 3% in H2O; [α]25/D -49.8°, c = 2 in H2O; -51 (c=3 in water)

Safety Information

• Storage Warning: Hygroscopic
• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (T); 99%
• Grade: puriss.
• Empirical Formula (Hill Notation): C6H10O3

DETAILS

MP Biomedicals - 05213625

MP Biomedicals Rare Chemical collection

Sigma Aldrich - P2625

Other Notes
Degradation product of pantothenic acid.

Sigma Aldrich - 237817

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 55200

Other Notes
Use as chiral building block: reduction to the triol1; Amidation2; Convenient acces to two enantiomeric oxiranes: S(+)- and R(-)-2,2-dimethyl-3,4-epoxybutanol3

Toronto Research Chemicals - P182500

An important intermediate in the synthesis of pantothenic acid as well as a degradation product of pantothneic acid in the liver. Causes disorientation and hypothermia, and prevents phenamine-induced hyperthermia.

REFERENCES

• Williams, M.: Science, 91, 246 (1940)
• Glaser et al.: Monatsch. Chem., 25, 46 (1940)
• Stiller et al.: J. Am. Chem. Soc., 62, 1785 (1940)
• Dorofeev, B.F. et al.: Dep. Doc., 14 (1940)
• Chiral auxiliary for enantioselective Diels-Alder reactions. Esters with acrylic acids react with dienes to give adducts with exo-endo selectivity and high ee: Tetrahedron Lett., 26, 3095 (1985); 30, 5599 (1989); Tetrahedron: Asymmetry, 1, 537 (1990). Preferred chiral auxiliary for kinetic resolution of ɑ-amino esters: Tetrahedron Lett., 34, 4473 (1993); J. Org. Chem., 64, 7700 (1999).