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

• ChemBase ID: 92030
• Molecular Formular: C16H24O14
• Molecular Mass: 440.35336
• Monoisotopic Mass: 440.11660545
• SMILES: O1CCO[C@@H]([C@@H](OCCOCCO[C@H](C(=O)O)[C@H](C(=O)O)OCC1)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-/m1/s1
• InChIKey: FZERLKNAJSFDSQ-DDHJBXDOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,11R,12R)-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid
• IUPAC Traditional name: (2R,3R,11R,12R)-1,4,7,10,13,16-hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid
• Synonyms: (+)-(Crown-6)-2,3,11,12-tetracarboxylic acid; (2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid; (2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid; (+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid; (2R,3R,11R,12R)-1,4,7,10,13,16-六氧环十八烷-2,3,11,12-四羧酸; (+)-(18-冠-6)-2,3,11,12-四羧酸

Database IDs

• CAS Number: 61696-54-6
• MDL Number: MFCD00040514
• Beilstein Number: 4240375
• PubChem SID: 162078728; 24867945
• PubChem CID: 3082976

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

• Melting Point: 210-212 °C; 210-212 °C(lit.); 210-212°C
• Optical Rotation: [α]20/D +62°, c = 1 in methanol; [α]20/D +70±2°, c = 1% in methanol

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (C); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C16H24O14

DETAILS

Apollo Scientific Ltd - OR8252T

A calcium & barium chelator.

Sigma Aldrich - 442666

Application
Derived tetracarboxylic acid chloride of this crown ether reacts with meta- and para-xylylene diamines to form chiral captands in high yields.1 Used as a chiral selector in capillary zone electrophoresis for the separation of a variety of optically active amines.2 Synthesis of monoamides.3
Packaging
25, 100 mg in glass bottle

Sigma Aldrich - 28127

Other Notes
Chiral crown ether1; Metal ion complexation2; Capping with diamines to captands3; Resolution by complexation with capillary zone electrophoresis4