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442666

Sigma-Aldrich

(+)-(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:
61696-54-6
Molecular Weight:
440.35
Beilstein:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
07624JQ
07408DR
06812EN
05905BA
05623BS

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Su Jin Lee et al.
Journal of chromatography. A, 1188(2), 318-321 (2008-03-19)
Racemic vigabatrin, an anticonvulsant drug used for the treatment of epilepsy, and its analogue gamma-amino acids were resolved without derivatization on liquid chromatographic chiral stationary phases (CSPs) based on (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid. Between the two CSPs which contain 3 methylene-unit or
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
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
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
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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