442666
(+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid
97%
Synonym(s):
(2R,3R,11R,12R)-1,4,7,10,13,16-Hexaoxacyclooctadecane-2,3,11,12-tetracarboxylic acid
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About This Item
Empirical Formula (Hill Notation):
C16H24O14
CAS Number:
Molecular Weight:
440.35
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4240375
Assay:
97%
assay
97%
optical activity
[α]20/D +62°, c = 1 in methanol
mp
210-212 °C (lit.)
functional group
carboxylic acid, ether
SMILES string
OC(=O)[C@@H]1OCCOCCO[C@H]([C@@H](OCCOCCO[C@H]1C(O)=O)C(O)=O)C(O)=O
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
InChI key
FZERLKNAJSFDSQ-DDHJBXDOSA-N
Application
Derived tetracarboxylic acid chloride of this crown ether reacts with meta- and para-xylylene diamines to form chiral captands in high yields. Used as a chiral selector in capillary zone electrophoresis for the separation of a variety of optically active amines. Synthesis of monoamides.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Hee Jung Choi et al.
Journal of chromatography. A, 1164(1-2), 235-239 (2007-08-04)
Two types of secondary amino alcohols were successfully resolved on a liquid chromatographic chiral stationary phase based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. The secondary amino alcohols containing a secondary amino group connected directly to the stereogenic center were resolved much better than
Anna R M Hyyryläinen et al.
Journal of the American Society for Mass Spectrometry, 20(7), 1235-1241 (2009-03-20)
Chiral differentiation of four enantiomeric pairs of beta-amino acids, cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)-, and trans-(1S,2S)-2-aminocyclopentanecarboxylic acids (cyclopentane beta-amino acids), and cis-(1R,2S)-, cis-(1S,2R)-, trans-(1R,2R)-, and trans-(1S,2S)-2-aminocyclohexanecarboxylic acids (cyclohexane beta-amino acids) was performed successfully by using host-guest complexes and ion/molecule reactions. The experiments
Myung Ho Hyun et al.
Chirality, 20(3-4), 325-329 (2007-07-07)
A doubly tethered chiral stationary phase (CSP) prepared by bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid to doubly tethered primary aminoalkyl silica gel was used for the resolution of various beta-amino acids. All the beta-amino acids tested were resolved quite well, the separation (alpha)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 442666-100MG-A | 04061833280096 |
| 442666-25MG-A | 04061833280102 |