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442666

Sigma-Aldrich

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

97%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C16H24O14
Numero CAS:
61696-54-6
Peso molecolare:
440.35
Beilstein:
4240375
Numero MDL:
MFCD00040514
Codice UNSPSC:
12352005
ID PubChem:
24867945
NACRES:
NA.22

Saggio

97%

Attività ottica

[α]20/D +62°, c = 1 in methanol

Punto di fusione

210-212 °C (lit.)

Gruppo funzionale

carboxylic acid
ether

Stringa SMILE

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
FZERLKNAJSFDSQ-DDHJBXDOSA-N

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Applicazioni

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]

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

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

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Sigma-Aldrich

8.11866

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Crown ether/Dibenzo-18-crown-6 for synthesis

Sigma-Aldrich

8.11731

Crown ether/Dibenzo-18-crown-6

1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane ≥96%

Sigma-Aldrich

295809

1,4,10,13-Tetraoxa-7,16-diazacyclooctadecane

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, 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
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
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
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