(3R,4R)-4-(hydroxymethyl)oxolane-2,3,4-triol

• ChemBase ID: 125904
• Molecular Formular: C5H10O5
• Molecular Mass: 150.1299
• Monoisotopic Mass: 150.05282342
• SMILES: O[C@]1(CO)COC(O)[C@@H]1O
• Canonical SMILES: OC[C@@]1(O)COC([C@@H]1O)O
• InChI: InChI=1S/C5H10O5/c6-1-5(9)2-10-4(8)3(5)7/h3-4,6-9H,1-2H2/t3-,4?,5+/m0/s1
• InChIKey: ASNHGEVAWNWCRQ-LJJLCWGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4R)-4-(hydroxymethyl)oxolane-2,3,4-triol
• IUPAC Traditional name: apiose
• Synonyms: 3-C-Hydroxymethyl-D-glycero-tetrose; D-Apiose solution; D-apiose; 3-C-(hydroxymethyl)-D-glycerotetrose; apio-β-D-furanosyl; Apiose; D-Apiose

Database IDs

• CAS Number: 639-97-4
• MDL Number: MFCD08459679
• PubChem SID: 162220248
• PubChem CID: 12306753; 4658
• Chemspider ID: 16735670
• Wikipedia Title: Apiose

CALCULATED PROPERTIES

• Acid pKa: 11.235591
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -2.4382033
• LogD (pH = 7.4): -2.438266
• Log P: -2.4382026
• Molar Refractivity: 30.1803 cm^3
• Polarizability: 12.6405 Å^3
• Polar Surface Area: 90.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥99.0% (HPLC)
• Concentration: 100-1000 mM in H2O
• Empirical Formula (Hill Notation): C5H10O5

DETAILS

Sigma Aldrich - 41239

Packaging
Pack size based on mg solid
Application
D-Apiose, a plant-specific branched-chain monosaccharide found in rhamnogalacturonan II (RG-II), apiogalacturonan, and several apioglycosides, serves as a borate binding site for crosslinking of galacturonans within plant cell walls.