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442666

Sigma-Aldrich

(+)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid

97%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C16H24O14
Número de CAS:
61696-54-6
Peso molecular:
440.35
Beilstein/REAXYS Number:
4240375
MDL number:
MFCD00040514
UNSPSC Code:
12352005
PubChem Substance ID:
24867945
NACRES:
NA.22

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

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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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
15815CO
14504LQ
12702TQ
11831MQ
07330LQ

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12-Crown-4 98%

Sigma-Aldrich

194905

12-Crown-4

Dibenzo-18-crown-6 98%

Sigma-Aldrich

158399

Dibenzo-18-crown-6

18-Crown-6 ≥99.0%

Sigma-Aldrich

274984

18-Crown-6

Suzanne Anouti et al.
Electrophoresis, 30(1), 2-10 (2008-12-25)
A new methodology based on heart-cutting 2-D CE in a single capillary was developed for the chiral separation of a mixture of 22 underivatized amino acids. The first dimension is performed in an achiral BGE (2.3 M acetic acid, pH
Suzanne Anouti et al.
Electrophoresis, 31(6), 1029-1035 (2010-03-24)
The use of transient moving chemical reaction boundary (tMCRB) was investigated for the on-line preconcentration of native amino acids in heart-cutting 2D-CE with multiple detection points using contactless conductivity detection. The tMCRB focusing was obtained by using ammonium formate (pH
Je Young Park et al.
Chirality, 24(5), 427-431 (2012-04-18)
3-Amino-5-phenyl (or 5-methyl)-1,4-benzodiazepin-2-ones, which are chiral precursors of anti-respiratory syncytial virus active agents, were resolved on three different chiral stationary phases (CSPs) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid or (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6. Among the three CSPs, the CSP that is based on (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6 and
Taeho Lee et al.
Journal of chromatography. A, 1217(8), 1425-1428 (2010-01-12)
(-)-(18-Crown-6)-2,3,11,12-tetracarboxylic acid-bonded silica was used as the chiral stationary phase in capillary electrochromatography (CEC) for enantioseparation of some alpha-amino acids. Separation data in CEC were measured in mobile phases of varying pH, and composition of methanol and buffer, and compared
István Ilisz et al.
Journal of chromatography. A, 1217(7), 1075-1082 (2009-07-21)
Reversed-phase high-performance liquid chromatographic methods were developed for the separation of enantiomers of eleven unnatural beta(2)-amino acids on a new chiral stationary phase, using the 11-methylene-unit spacer of aminoundecylsilica gel for the bonding of (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid as selector. The nature
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