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Merck
CN

358924

(+)-O,O′-Diacetyl-L-tartaric anhydride

97%

Synonym(s):

(+)-Diacetyl-L-tartaric anhydride

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About This Item

Empirical Formula (Hill Notation):
C8H8O7
CAS Number:
6283-74-5
Molecular Weight:
216.14
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24862037
EC Number:
228-502-7
Beilstein/REAXYS Number:
87315
MDL number:
MFCD00037918

Key Documents

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Product Name

(+)-O,O′-Diacetyl-L-tartaric anhydride, 97%

InChI key

XAKITKDHDMPGPW-PHDIDXHHSA-N

InChI

1S/C8H8O7/c1-3(9)13-5-6(14-4(2)10)8(12)15-7(5)11/h5-6H,1-2H3/t5-,6-/m1/s1

SMILES string

CC(=O)O[C@@H]1[C@@H](OC(C)=O)C(=O)OC1=O

assay

97%

optical activity

[α]20/D +59°, c = 6 in acetone

mp

130-135 °C (lit.)

functional group

anhydride
ester

storage temp.

2-8°C

Quality Level

100

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Application

(+)-O,O′-Diacetyl-L-tartaric anhydride may be used as a chiral derivatizating agent in the following:
  • determination of enantiomeric vigabatrin in mouse serum samples using ultra-high performance liquid chromatography-quadrupole-time-of-flight mass spectrometry (UHPLC-Q-TOF-M)        
  • determination of trantinterol in rat plasma by ultra performance liquid chromatography–electrospray ionization mass spectrometry (UPLC–MS/MS)

General description

(+)-O,O′-Diacetyl-L-tartaric anhydride is an HPLC derivatization reagent for UV/Vis detection. It is mainly employed as a reagent for the chiral derivatization of amino alcohols. It also reacts with alkanoamines in aprotic medium containing trichloroacetic acid and produces tartaric acid monoesters.

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCG2559
BCBV5535
BCBP0456V
1451758V
1451758

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Determination of enantiomeric vigabatrin by derivatization with diacetyl-l-tartaric anhydride followed by ultra-high performance liquid chromatography-quadrupole-time-of-flight mass spectrometry
Zhao J, et al.
Journal of Chromatography. B, Biomedical Sciences and Applications, 1040, 199-207 (2017)
Enantioselective determination of trantinterol in rat plasma by ultra performance liquid chromatography?electrospray ionization mass spectrometry after derivatization
Yang J, et al.
Talanta, 79(5), 1204-1208 (2009)
W Schützner et al.
Electrophoresis, 15(6), 769-773 (1994-06-01)
Diastereomeric analytes were separated using capillary zone electrophoresis with polyvinylpyrrolidone as polymeric additive to the buffer solution. As test substances derivatives of D- and L- alpha-amino and alpha-hydroxy acids formed by reaction with (+)-O,O'-diacetyl- and (+)-O,O'-dibenzoyl-L-tartaric anhydride, respectively, were used.
W Lindner et al.
Journal of chromatography, 487(2), 375-383 (1989-02-24)
A sensitive high-performance liquid chromatographic method was developed for the stereoselective assay of (R)- and (S)-propranolol in human plasma. The method involves diethyl ether extraction of the drugs and a racemic internal standard, N-tert.-butylpropranolol, followed by derivatization of the compounds
William M Oldham et al.
Bio-protocol, 6(16) (2017-06-03)
Two enantiomers of 2-hydroxyglutarate (2HG), L (L2HG) and D (D2HG), are metabolites of unknown function in mammalian cells that were initially associated with separate and rare inborn errors of metabolism resulting in increased urinary excretion of 2HG linked to neurological
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