(2R,3S,11R,12S)-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid

• ChemBase ID: 165042
• Molecular Formular: C16H24O14
• Molecular Mass: 440.35336
• Monoisotopic Mass: 440.11660545
• SMILES: [C@H]1(OCCOCCO[C@@H]([C@@H](OCCOCCO[C@@H]1C(=O)O)C(=O)O)C(=O)O)C(=O)O
• Canonical SMILES: OC(=O)[C@@H]1OCCOCCO[C@H](C(=O)O)[C@@H](OCCOCCO[C@@H]1C(=O)O)C(=O)O
• InChI: InChI=1S/C16H24O14/c17-13(18)9-10(14(19)20)29-7-3-26-4-8-30-12(16(23)24)11(15(21)22)28-6-2-25-1-5-27-9/h9-12H,1-8H2,(H,17,18)(H,19,20)(H,21,22)(H,23,24)/t9-,10+,11+,12-
• InChIKey: FZERLKNAJSFDSQ-IWDIQUIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,11R,12S)-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid
• IUPAC Traditional name: (2R,3S,11R,12S)-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid
• Synonyms: (2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic Acid; (+)-18-Crown-6 tetracarboxylic Acid; Bis(L-tartaric Acid) 18-Crown-6; (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic Acid

Database IDs

• CAS Number: 61696-54-6
• PubChem SID: 162259175
• PubChem CID: 71315010

CALCULATED PROPERTIES

• Acid pKa: 2.775193
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): -7.453624
• LogD (pH = 7.4): -13.088139
• Log P: -1.5220946
• Molar Refractivity: 89.5806 cm^3
• Polarizability: 36.451042 Å^3
• Polar Surface Area: 204.58 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 201-204°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - C825000

A calcium and barium chelator. A useful chiral NMR discriminating agent for underivatized amino acids.

REFERENCES

• Behr., J-P, et al.: Helvetica Chimica Acta., 65 (6)
• 182, 1853 (6)
• Dutton, P.J., et al.: Can. J. Chem., 66, 1097 (6)
• Wenzel, T.J., et al.: Tetrahedron Lett., 41, 3769 (2000)