(2S,3R)-2-methylbutane-1,2,3,4-tetrol

• ChemBase ID: 154549
• Molecular Formular: C5H12O4
• Molecular Mass: 136.14638
• Monoisotopic Mass: 136.07355886
• SMILES: CC(CO)([C@@H](CO)O)O
• Canonical SMILES: OC[C@H](C(CO)(O)C)O
• InChI: InChI=1S/C5H12O4/c1-5(9,3-7)4(8)2-6/h4,6-9H,2-3H2,1H3/t4-,5+/m1/s1
• InChIKey: HGVJFBSSLICXEM-UHNVWZDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-2-methylbutane-1,2,3,4-tetrol
• IUPAC Traditional name: (2S,3R)-2-methylbutane-1,2,3,4-tetrol
• Synonyms: (2S,3R)-2-Methyl-1,2,3,4-tetrahydroxybutane; (2S,3R)-2-Methylbutane-1,2,3,4-tetrol; 2-C-Methyl-D-erythritol

Database IDs

• MDL Number: MFCD17215928
• Beilstein Number: 5916602
• PubChem SID: 162248687
• PubChem CID: 11400799

CALCULATED PROPERTIES

• Acid pKa: 12.885995
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -2.1887722
• LogD (pH = 7.4): -2.1887736
• Log P: -2.1887722
• Molar Refractivity: 31.1168 cm^3
• Polarizability: 12.55117 Å^3
• Polar Surface Area: 80.92 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥90% (GC)
• Empirical Formula (Hill Notation): C5H12O4

DETAILS

Sigma Aldrich - 41707

Biochem/physiol Actions
Metabolite of the non-mevalonate MEP pathway, generally found in prokaryotes, as precursor to isoprenoids as well as non-isoprenoids like vitamins. As this pathway is not present in humans, it is of interest for the development of bacterium-specific drugs in the search for treatments of infectious diseases.
General description
(2S,3R)-2-methylbutane-1,2,3,4-tetrol was identified as a glucide in methanol extracts of Carum ajowan fruit.