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358924

Sigma-Aldrich

(+)-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
Beilstein:
87315
EC Number:
228-502-7
MDL number:
MFCD00037918
UNSPSC Code:
12352005
PubChem Substance ID:
24862037
NACRES:
NA.22

Assay

97%

optical activity

[α]20/D +59°, c = 6 in acetone

mp

130-135 °C (lit.)

storage temp.

2-8°C

SMILES string

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

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

InChI key

XAKITKDHDMPGPW-PHDIDXHHSA-N

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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.

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)

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
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
D R Brocks et al.
Journal of pharmaceutical and biomedical analysis, 13(7), 911-918 (1995-06-01)
A stereospecific liquid chromatographic (LC) assay was developed for the quantification of the antimalarial drug, halofantrine, in human plasma. Following protein precipitation with acetonitrile, the enantiomers of halofantrine were extracted from human plasma using ammonium hydroxide and tert-butyl methyl ether-hexane.
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)
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