(3S,4S)-1,3,4,5-tetrahydroxypentan-2-one

• ChemBase ID: 3582
• Molecular Formular: C5H10O5
• Molecular Mass: 150.1299
• Monoisotopic Mass: 150.05282342
• SMILES: OC[C@H](O)[C@H](O)C(=O)CO
• Canonical SMILES: OC[C@@H]([C@@H](C(=O)CO)O)O
• InChI: InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h3,5-8,10H,1-2H2/t3-,5-/m0/s1
• InChIKey: ZAQJHHRNXZUBTE-UCORVYFPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S)-1,3,4,5-tetrahydroxypentan-2-one
• IUPAC Traditional name: L-ribulose
• Synonyms: D-Xylulose; threo-2-Pentulose; L-threo-Pentulose; L-Xylulose; L-Adonose; L-erythro-2-Pentulose; L-Ribulose; L-苏式-戊酮糖; 苏式-2-戊酮糖; L-木酮糖

Database IDs

• CAS Number: 527-50-4; 2042-27-5; 551-84-8
• MDL Number: MFCD00075347
• PubChem SID: 24902124; 46505615; 160967020
• PubChem CID: 644111

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.569923
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.6367006
• LogD (pH = 7.4): -2.6369903
• Log P: -2.636697
• Molar Refractivity: 31.5993 cm^3
• Polarizability: 12.73608 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -2.16
• LOG S: 0.65
• Solubility (Water): 6.78e+02 g/l

PROPERTIES

Physical Property

• Apperance: light yellow syrup
• Flash Point: >113 °C; >235.4 °F; 113 °C; 235.4 °F
• Optical Rotation: [α]/D +16.5±1.5°, c = 0.1 in H2O; [α]20/D +26°, c = 1 in H2O

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: ~95%; ≥90% (HPLC)
• Empirical Formula (Hill Notation): C5H10O5

DETAILS

DrugBank - DB03947

Drug information: experimental

Sigma Aldrich - 75436

Biochem/physiol Actions
Important metabolite in pentose interconversions, for analyzing L-ribose isomerase1, engineering yeast for xylose metabolism2, interesting chiral pool compound3.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 75436.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.