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Merck

358924

Sigma-Aldrich

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

97%

Sinónimos:

(+)-Diacetyl-L-tartaric anhydride

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About This Item

Fórmula empírica (notación de Hill):
C8H8O7
Número de CAS:
Peso molecular:
216.14
Beilstein/REAXYS Number:
87315
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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

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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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)
D R Brocks et al.
Journal of chromatography, 581(1), 83-92 (1992-10-02)
(+/-)-Hydroxychloroquine (HCQ) is an antimalarial and anti-arthritic drug which is administered as the racemate. An accurate, precise and sensitive high-performance liquid chromatographic assay was developed for the determination of HCQ enantiomers in samples from human plasma, serum, whole blood, and
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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