(2R)-3-hydroxy-2-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid

• ChemBase ID: 155960
• Molecular Formular: C9H16O9
• Molecular Mass: 268.21794
• Monoisotopic Mass: 268.07943209
• SMILES: C([C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)O[C@H](CO)C(=O)O)O)O)O)O
• Canonical SMILES: OC[C@H]1O[C@@H](O[C@@H](C(=O)O)CO)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C9H16O9/c10-1-3-5(12)6(13)7(14)9(17-3)18-4(2-11)8(15)16/h3-7,9-14H,1-2H2,(H,15,16)/t3-,4-,5-,6+,7+,9+/m1/s1
• InChIKey: DDXCFDOPXBPUJC-MTXRGOKVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-3-hydroxy-2-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid
• IUPAC Traditional name: (2R)-3-hydroxy-2-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid
• Synonyms: (2R)-O2-(β-D-mannopyranosyl)glyceric acid; Firoin from Rhodothermus marinus

Database IDs

• CAS Number: 164324-35-0
• PubChem SID: 162250098
• PubChem CID: 71312248

CALCULATED PROPERTIES

• Acid pKa: 3.3488944
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -5.425934
• LogD (pH = 7.4): -6.7048583
• Log P: -3.289575
• Molar Refractivity: 52.7968 cm^3
• Polarizability: 22.084507 Å^3
• Polar Surface Area: 156.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

Product Information

• Purity: ~80% (TLC)
• Impurities: ~10% potassium chloride
• Empirical Formula (Hill Notation): C9H16O9

DETAILS

Sigma Aldrich - 96647

Application
Firoin is the dominant and very effective protectant (hypersolute) against heat denaturation from Rhodothermus marinus