(3S)-1,3,4-trihydroxybutan-2-one

• ChemBase ID: 154022
• Molecular Formular: C4H8O4
• Molecular Mass: 120.10392
• Monoisotopic Mass: 120.04225874
• SMILES: C([C@@H](C(=O)CO)O)O
• Canonical SMILES: OCC(=O)[C@H](CO)O
• InChI: InChI=1S/C4H8O4/c5-1-3(7)4(8)2-6/h3,5-7H,1-2H2/t3-/m0/s1
• InChIKey: UQPHVQVXLPRNCX-VKHMYHEASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-1,3,4-trihydroxybutan-2-one
• IUPAC Traditional name: L-erythrulose
• Synonyms: S-1,3,4-Trihydroxy-2-butanone; L-Glycero-2-tetrulose; L-(+)-Erythrulose

Database IDs

• CAS Number: 533-50-6
• MDL Number: MFCD00004703
• PubChem SID: 162248161; 24880445
• PubChem CID: 5460032

CALCULATED PROPERTIES

• Acid pKa: 12.324061
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.006362
• LogD (pH = 7.4): -2.0063672
• Log P: -2.006362
• Molar Refractivity: 25.6368 cm^3
• Polarizability: 10.220809 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: 110 °C; 230 °F
• Optical Rotation: [α]/D 12.0±2.0°, c = 2 in H2O (24 h)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: ≥85% (HPLC)
• Impurities: ≤15% water
• Empirical Formula (Hill Notation): C4H8O4

DETAILS

Sigma Aldrich - 56845

Application
L-(+)-Erythrulose is used as a tanning agent in the cosmetics industry and a source of chiral ethyl ketones used in aldo reaction organic synthesis.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 56845.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.