(3R,4R)-3,4-dihydroxyoxolan-2-one

• ChemBase ID: 151201
• Molecular Formular: C4H6O4
• Molecular Mass: 118.08804
• Monoisotopic Mass: 118.02660867
• SMILES: C1[C@H]([C@H](C(=O)O1)O)O
• Canonical SMILES: O[C@@H]1[C@H](O)COC1=O
• InChI: InChI=1S/C4H6O4/c5-2-1-8-4(7)3(2)6/h2-3,5-6H,1H2/t2-,3-/m1/s1
• InChIKey: SGMJBNSHAZVGMC-PWNYCUMCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-3,4-dihydroxyoxolan-2-one
• IUPAC Traditional name: erythrono-1,4-lactone
• Synonyms: (3R-cis) (-)-Dihydro-3,4-dihydroxy-2(3H)-furanone; D-Erythronolactone; D-Erythronic acid γ-lactone; (3R,4R)-Dihydro-3,4-dihydroxy-2(3H)-furanone; D-Erythronolactone; (2R,3R)-Butane-2,3,4-triol-1,4 Lactone; D-Erythronic γ-Lactone; (3R-顺式) (-)-二氢-3,4-二羟基-2(3H)-呋喃酮; D-三羟丁酸 γ-内酯; D-赤酮酸内酯

Database IDs

• CAS Number: 15667-21-7
• MDL Number: MFCD00077763
• Beilstein Number: 81073
• PubChem SID: 162245358; 24863305
• PubChem CID: 5325915

CALCULATED PROPERTIES

• Acid pKa: 11.661598
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.4846036
• LogD (pH = 7.4): -1.484627
• Log P: -1.4846033
• Molar Refractivity: 22.8538 cm^3
• Polarizability: 9.602581 Å^3
• Polar Surface Area: 66.76 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Solid
• Melting Point: 100-102 °C(lit.); 97.5-99.5°C
• Optical Rotation: [α]20/D -71°, c = 1 in H2O; [α]20/D -72±3°, c = 4.5% in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (T); 95%
• Grade: purum
• Empirical Formula (Hill Notation): C4H6O4

DETAILS

Sigma Aldrich - 374385

Packaging
1 g in glass bottle

Sigma Aldrich - 45676

Other Notes
Chiral diol-lactone used as chiral building block1,2,3,4

Toronto Research Chemicals - E658500

A chiral synthon used for the synthesis of certain natural products such as the leukotrienes.

REFERENCES

• Yew, W., et al.: Biochem., 45, 14582 (2006)
• Ohta, T., et al.: Toxicol. Pathol., 37, 521 (2006)