(3R)-3-hydroxy-4,4-bis(2H3)methyloxolan-2-one

• ChemBase ID: 176220
• Molecular Formular: C6H10O3
• Molecular Mass: 130.1418
• Monoisotopic Mass: 130.06299418
• SMILES: [C@H]1(C(COC1=O)(C)C)O
• 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-bis(^2H₃)methyloxolan-2-one
• IUPAC Traditional name: (3R)-3-hydroxy-4,4-bis(^2H₃)methyloxolan-2-one
• Synonyms: (3R)-Dihydro-3-hydroxy-4,4-(dimethyl-d6)-2(3H)-furanone; (-)-(R)-Pantolactone-d6; (-)-2-Hydroxy-3,3-(dimethyl-d6)-γ-butyrolactone; (-)-Pantoyl Lactone-d6; (3R)-Tetrahydro-3-hydroxy-4,4-(dimethyl-d6)furan-2-one; Pantothenic Lactone-d6; D-(-)-α-Hydroxy-β,β-(dimethyl-d6)-γ-butyrolactone; (R)-α-Hydroxy-β,β-(dimethyl-d6)-γ-butyrolactone; D-(-)-Pantolactone-d6

Database IDs

• PubChem SID: 164232130
• PubChem CID: 71751460

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

DETAILS

Toronto Research Chemicals - P182502

A labelled 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)